#------------------------------------------------------------------------------
#$Date: 2023-06-06 07:34:37 +0200 (Tue, 06 Jun 2023) $
#$Revision: 284385 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/27/2022735.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022735
loop_
_publ_author_name
'Prasad, Holehundi J Shankara'
'Devaraju, ?'
'Yathirajan, Hemmige S.'
'Akkurt, Mehmet'
'Foro, Sabine'
'Balerao, Rishik'
'Butcher, Ray J.'
_publ_section_title
;
Syntheses and crystal structures of three salts of
1-(4-nitro-phenyl)-piperazine.
;
_journal_issue 'Pt 5'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first 423
_journal_page_last 427
_journal_paper_doi 10.1107/S205698902300302X
_journal_volume 79
_journal_year 2023
_chemical_formula_iupac 'C10 H14 N3 O2 +, C7 H4 Br O2 - , 0.5H2 O'
_chemical_formula_moiety 'C10 H14 N3 O2 +, C7 H4 Br O2 -, 0.5(H2 O)'
_chemical_formula_sum 'C17 H19 Br N3 O4.5'
_chemical_formula_weight 417.26
_chemical_name_systematic
;
4-(4-Nitrophenyl)piperazin-1-ium 2-bromobenzoate hemihydrate
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_Hall '-P 1'
_space_group_name_H-M_alt 'P -1'
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-2018/3
_cell_angle_alpha 102.101(6)
_cell_angle_beta 99.534(6)
_cell_angle_gamma 110.981(6)
_cell_formula_units_Z 2
_cell_length_a 7.2570(5)
_cell_length_b 9.7772(6)
_cell_length_c 14.2020(10)
_cell_measurement_reflns_used 2832
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 27.92
_cell_measurement_theta_min 3.03
_cell_volume 887.41(12)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al., 2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015a)
;
_computing_structure_solution
;
SHELXL2018 (Sheldrick, 2015b)
;
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device_type 'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method \w
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0163
_diffrn_reflns_av_unetI/netI 0.0423
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_number 6177
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.980
_diffrn_reflns_theta_min 3.039
_exptl_absorpt_coefficient_mu 2.347
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.78116
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysalisRed; Oxford Diffraction, 2009)
;
_exptl_crystal_colour brown
_exptl_crystal_density_diffrn 1.562
_exptl_crystal_description prism
_exptl_crystal_F_000 426
_exptl_crystal_size_max 0.360
_exptl_crystal_size_mid 0.320
_exptl_crystal_size_min 0.200
_refine_diff_density_max 0.508
_refine_diff_density_min -0.326
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.944
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 244
_refine_ls_number_reflns 3856
_refine_ls_number_restraints 5
_refine_ls_restrained_S_all 1.234
_refine_ls_R_factor_all 0.0692
_refine_ls_R_factor_gt 0.0360
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0444P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0765
_refine_ls_wR_factor_ref 0.0843
_reflns_number_gt 2478
_reflns_number_total 3856
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file hb8051sup1.cif
_cod_data_source_block 2
_cod_depositor_comments
'Adding full bibliography for 2022734--2022736.cif.'
_cod_original_cell_volume 887.41(11)
_cod_original_formula_sum 'C17 H19 Br N3 O4.50'
_cod_database_code 2022735
_cod_database_fobs_code 2022735
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min 0.485
_shelx_estimated_absorpt_t_max 0.651
_shelx_hkl_file
;
0 0 2 5395.03 36.4547 0
0 0 3 1302.63 22.3304 1
0 0 3 1365.13 24.9417 0
0 0 4 608.009 19.8759 1
0 0 5 11103.8 77.1496 1
0 0 6 234.488 20.8436 1
0 0 6 254.926 18.2530 4
0 0 7 123.180 22.5295 1
0 0 7 146.773 18.7499 4
0 0 8 5965.82 65.7080 4
0 0 8 5774.47 75.0427 1
0 0 9 5438.77 78.4537 1
0 0 9 5757.23 68.7963 4
0 0 10 87.1182 25.7285 4
0 0 10 108.569 30.8379 1
0 0 11 757.464 56.0773 6
0 0 11 751.446 45.2826 1
0 0 12 43.7817 35.2183 1
0 0 12 34.5701 42.9320 6
0 0 13 257.276 56.1967 6
0 0 13 249.010 41.8327 1
0 0 14 458.011 61.6422 6
0 0 15 159.769 54.0746 6
0 0 16 35.6599 57.5454 6
0 -1 17 41.2849 57.0411 6
0 -1 16 83.6628 63.4368 6
0 -1 15 9.89064 53.7842 6
0 -1 14 1166.05 62.4543 1
0 -1 14 1153.95 70.8469 6
0 -1 13 613.038 50.1370 1
0 -1 13 575.413 57.5681 6
0 -1 12 833.442 47.4910 1
0 -1 12 858.590 60.9223 6
0 -1 12 812.886 42.2718 4
0 -1 11 2201.94 61.6168 1
0 -1 11 2167.67 54.9044 4
0 -1 10 561.948 38.0645 1
0 -1 9 2529.13 56.8182 1
0 -1 8 5024.42 69.9808 1
0 -1 7 826.440 31.3565 1
0 -1 6 617.889 25.6322 1
0 -1 5 27301.0 121.466 1
0 -1 4 13851.4 78.4496 1
0 -1 3 201.375 12.4854 1
0 -1 2 7506.81 44.9024 1
0 1 1 1297.65 20.6374 0
0 1 2 1516.54 26.3375 0
0 -1 -2 1556.67 21.9420 1
0 1 3 13683.1 72.3876 1
0 1 3 13905.5 81.1053 0
0 1 3 13736.3 57.3691 4
0 1 4 2458.03 36.2448 1
0 1 4 2451.20 29.0127 4
0 1 4 2381.59 41.2181 0
0 1 5 5995.54 60.8923 1
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0 1 5 6516.75 69.8299 0
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0 1 6 5549.93 71.6445 0
0 1 6 5342.99 63.4849 1
0 1 7 26.5240 16.3258 4
0 1 7 26.9110 28.7290 0
0 1 7 36.8378 21.9622 1
0 1 8 3684.03 50.7841 4
0 1 8 3504.57 61.6134 1
0 1 8 3461.10 69.1028 0
0 1 9 1959.68 53.1982 1
0 1 9 2100.77 68.0667 6
0 1 9 2013.85 42.6470 4
0 1 10 911.895 44.2742 1
0 1 10 906.152 55.6297 6
0 1 11 2502.62 65.4231 1
0 1 11 2489.77 82.0926 6
0 1 12 271.880 47.1781 6
0 1 12 257.876 41.6316 1
0 1 13 189.217 54.6143 6
0 1 14 340.498 59.1910 6
0 1 15-32.8734 58.1539 6
0 1 16 310.075 69.0957 6
0 -2 17 179.147 64.7642 6
0 -2 16 104.760 61.1040 6
0 -2 15 28.5291 54.0146 6
0 -2 15 31.2966 45.1795 1
0 -2 14 475.603 52.8214 1
0 -2 14 466.080 58.5500 6
0 -2 13 161.345 49.4732 6
0 -2 13 171.515 43.0978 1
0 -2 12 2493.39 81.5509 6
0 -2 12 2399.26 69.2861 1
0 -2 11 1473.96 54.6740 1
0 -2 10 634.344 39.3787 1
0 -2 9 955.936 41.0190 1
0 -2 8 7064.72 83.9180 1
0 -2 7 79.8517 22.1614 1
0 -2 6 3607.09 53.6565 1
0 -2 5 5802.85 61.9070 1
0 -2 4 37512.9 142.035 1
0 -2 3 111224. 909.600 1
0 -2 2 18839.1 90.8957 1
0 2 -2 18839.2 83.2422 3
0 2 -1 15869.5 84.5651 3
0 -2 1 15962.7 79.2745 1
0 2 0 205.765 16.6420 3
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0 -2 -3 8192.51 63.8966 1
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0 2 7 59.8554 15.8428 4
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0 2 10 439.438 40.0113 1
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0 -3 15 30.6716 47.0518 1
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0 -3 2 1081.35 30.7072 1
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0 -3 -4 316.701 22.7948 1
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-7 0 7-14.9226 45.1474 4
-7 0 6 374.067 55.2724 2
-7 0 5 12.9178 47.4969 2
-7 0 4 583.284 54.6737 2
-7 0 3 90.7038 46.2394 2
-7 0 3 105.707 43.0384 1
-7 0 2 155.434 52.3874 2
-7 0 2 167.397 45.6714 1
-7 0 1-11.5339 45.8349 2
7 0 -1-39.8496 48.7387 1
-7 0 1 56.2355 45.7550 1
-7 0 0 125.959 51.9236 2
7 0 0 105.964 52.2096 1
-7 0 -1-27.3487 52.4607 2
7 0 1 186.491 59.4164 1
-7 0 -2 43.8970 49.0748 2
7 0 2 54.4781 54.4755 1
-7 0 -3 41.3293 53.8637 2
7 0 3 92.1363 60.3368 1
7 0 4 3.36662 63.4182 1
7 0 5 32.9809 56.6718 1
-7 -1 13-23.2405 54.4394 4
-7 -1 12 58.9507 51.0330 4
-7 -1 11 188.204 63.4599 4
-7 -1 10 16.2835 45.8241 2
-7 -1 10-9.79260 48.4270 4
-7 -1 9 176.645 48.0229 2
-7 -1 9 145.243 48.3214 4
-7 -1 8 136.310 53.2894 2
-7 -1 8 163.507 50.1835 4
-7 -1 7-3.28784 49.6376 2
-7 -1 6 547.795 60.5363 2
-7 -1 5 620.807 59.6365 2
-7 -1 4 97.0876 52.9417 2
-7 -1 4 24.0514 45.3230 1
-7 -1 3 107.805 57.0416 2
-7 -1 3 149.910 47.9304 1
-7 -1 2-19.1430 48.3947 2
-7 -1 2 54.2155 49.3813 1
-7 -1 1 10.1653 55.7587 2
-7 -1 1 96.9074 50.5506 1
-7 -1 0-5.75299 57.5097 2
-7 -1 0 111.758 49.1308 1
-7 -1 -1-49.8211 57.5623 2
7 1 1 39.4960 58.7275 1
-7 -1 -2 10.3154 53.7015 2
7 1 2-7.77919 63.2874 1
-7 -1 -3 10.4160 57.0791 2
7 1 3-47.8613 57.9931 1
-7 -1 -4 121.801 52.8608 2
7 1 4 28.2590 63.9085 1
-7 -2 12 114.623 61.6353 4
-7 -2 11-0.12888 56.1812 2
-7 -2 11 30.9524 55.8836 4
-7 -2 10-31.8914 52.5348 2
-7 -2 10 109.654 55.5012 4
-7 -2 9 199.394 58.3489 2
-7 -2 8 58.5664 50.2417 2
-7 -2 7 44.8110 57.3772 2
-7 -2 6 209.874 57.3800 2
-7 -2 5 112.893 55.5477 2
-7 -2 5 144.167 52.6043 1
-7 -2 4 40.1622 58.4304 2
-7 -2 4 20.5552 47.9995 1
-7 -2 3 190.205 61.7364 2
-7 -2 3 183.288 55.9723 1
-7 -2 2 56.4825 57.4927 2
-7 -2 2 98.7369 56.2100 1
-7 -2 1 20.4237 52.7787 2
-7 -2 1 23.7293 54.1584 1
-7 -2 0 122.609 54.5157 1
7 2 1-61.0646 66.9914 1
-7 -2 -1 6.08675 58.5002 1
7 2 2 52.4874 72.6265 1
-7 -3 12 83.6876 54.5073 4
-7 -3 11 2.70763 54.7423 2
-7 -3 11 60.4622 56.3823 4
-7 -3 10 2.66250 56.5654 2
-7 -3 9 230.852 60.8380 2
-7 -3 8 96.3158 53.5842 2
-7 -3 7 36.4070 53.6418 2
-7 -3 6 57.9104 59.4312 2
-7 -3 6 158.932 57.2202 1
-7 -3 5 12.4814 59.9397 2
-7 -3 5 27.5461 51.9328 1
-7 -3 4-2.86097 55.2292 2
-7 -3 4-10.9162 56.5309 1
-7 -3 3 52.6026 64.7384 2
-7 -3 3-47.2250 58.3108 1
-7 -3 2-8.71970 56.7593 1
-7 -3 1 46.4715 56.6010 1
-7 -3 0 34.1566 64.9071 1
-7 -4 9 161.070 63.9248 2
-7 -4 8 62.2220 54.0083 2
-7 -4 7 59.8147 59.8646 2
-7 -4 7 7.33403 62.7775 1
-7 -4 6 252.261 62.4662 1
-7 -4 5 37.4756 61.6696 1
-7 -4 4-44.6244 58.9426 1
-7 -4 3 96.8890 64.7566 1
8 -9 -5-39.0319 74.1040 5
8 -9 -4-73.7399 73.6535 5
8 -9 -3 33.4743 70.9332 5
8 -9 -2 148.028 79.0644 5
8 -9 -1 18.6968 77.3729 5
8 -9 0-47.8709 78.3547 5
8 -9 1 31.0075 78.2617 5
8 -9 2-3.83976 74.9419 5
8 -8 -6 106.372 75.1346 5
8 -8 -5 193.183 74.7230 5
8 -8 -4 119.044 76.5754 5
8 -8 -3 127.321 74.5600 5
8 -8 -2 38.3378 74.6467 5
8 -8 -1-34.8980 73.4024 5
8 -8 0 49.8296 74.1318 5
8 -8 1 113.946 73.3034 5
8 -8 2-111.882 76.8455 5
8 -8 3 109.693 76.9040 5
8 -8 4 36.6694 72.2182 5
8 -8 5 86.8850 80.0729 5
-8 7 7 115.086 53.6904 4
8 -7 -6 106.129 67.5733 5
-8 7 6 12.6588 65.7382 4
8 -7 -5 21.7169 60.7073 5
-8 7 5 129.033 67.4886 4
8 -7 -4 30.0705 68.1723 5
8 -7 -3 176.922 74.6180 5
8 -7 -2 56.2982 70.6108 5
8 -7 -1-22.7915 72.1269 5
8 -7 0 245.556 73.7292 5
8 -7 1 10.9095 72.5523 5
8 -7 2 128.100 80.1001 5
8 -7 3 171.958 77.2843 5
8 -7 4-29.4309 76.1737 5
8 -7 5 9.38028 69.3057 5
8 -7 6 220.131 80.3669 5
-8 6 8 68.6854 63.3309 4
-8 6 7 201.131 56.1895 4
8 -6 -6 223.498 65.5115 5
-8 6 6 235.956 62.2682 4
8 -6 -5-12.2222 64.0977 5
-8 6 5 86.4251 56.1681 4
8 -6 -4 56.7021 65.5279 5
-8 6 4-26.7242 49.0474 4
8 -6 -3 198.513 69.1571 5
8 -6 -2-2.50143 66.5970 5
8 -6 -1-44.3403 68.3826 5
8 -6 0 36.9763 69.2021 5
8 -6 1-0.55005 68.3816 5
8 -6 2 202.791 76.0849 5
8 -6 3-2.43613 70.3606 5
8 -6 4-0.76377 73.9218 5
8 -6 5 20.8081 69.8777 5
8 -6 6 0.00000 74.7052 5
-8 5 9 62.8762 53.6514 4
-8 5 8 99.9718 63.9315 4
-8 5 7 78.3067 49.4163 4
8 -5 -6 313.482 66.1219 5
-8 5 6 313.131 56.7663 4
8 -5 -5 139.458 63.1322 5
-8 5 5 87.6312 50.7915 4
8 -5 -4 64.5045 64.8607 5
-8 5 4 6.84337 52.6990 4
8 -5 -3 162.455 66.3147 5
-8 5 3 136.963 53.9206 4
8 -5 -2-14.1230 60.3586 5
8 -5 -1 295.637 71.0714 5
8 -5 0 90.5789 67.3409 5
8 -5 1 85.6978 73.2845 5
8 -5 2 13.3957 69.2021 5
8 -5 3 82.3709 72.1981 5
8 -5 4-28.7002 70.8152 5
8 -5 5 321.645 80.2383 5
8 -5 6 7.02926 73.1405 5
8 -5 7-33.0331 58.8918 1
-8 4 10 39.7587 50.3424 4
-8 4 9 56.2186 56.5660 4
-8 4 8 14.0520 58.1459 4
-8 4 7 29.3722 51.8160 4
8 -4 -6 219.546 63.7099 5
-8 4 6 178.364 52.4291 4
8 -4 -5 6.51946 58.9294 5
-8 4 5 0.91506 52.1593 4
8 -4 -4 78.5388 62.2339 5
-8 4 4 84.5744 46.9761 4
8 -4 -3 18.6484 63.5851 5
-8 4 3 46.8304 47.4185 4
8 -4 -2-6.81426 61.6344 5
8 -4 -1 24.6862 65.7407 5
8 -4 0 140.943 69.6731 5
8 -4 1 11.5548 70.2369 5
8 -4 2 38.5774 68.5737 5
8 -4 3 57.4343 70.9000 5
8 -4 4-39.4689 66.6695 5
8 -4 5 20.0500 70.2700 5
8 -4 5 99.9566 53.1309 1
8 -4 6 79.8370 61.3593 1
-8 3 10 4.89350 58.5150 4
-8 3 9 311.217 65.3701 4
-8 3 8 304.407 57.5445 4
-8 3 7 34.2297 56.3259 4
8 -3 -6 133.943 59.1745 5
-8 3 6 95.0829 51.7495 4
8 -3 -5 0.62112 56.6871 5
-8 3 5-19.6944 45.1986 4
8 -3 -4 52.8847 61.7804 5
8 -3 -3 166.656 66.3242 5
8 -3 -2 33.2600 61.3469 5
8 -3 -1 100.456 66.5144 5
-8 3 0 156.512 48.8934 2
8 -3 0 175.936 67.0927 5
-8 3 -1 68.8088 48.0375 2
8 -3 1 94.6214 69.9601 5
-8 3 -2 348.396 58.9985 2
8 -3 2 342.189 75.1065 5
8 -3 3 25.4571 69.4108 5
8 -3 4 10.9450 57.0244 1
8 -3 5-20.0362 61.7949 1
8 -3 6-59.6872 56.6388 1
-8 2 11 29.0055 59.4145 4
-8 2 10-36.8291 57.0613 4
-8 2 9-18.1274 51.7496 4
-8 2 8 101.936 60.5762 4
-8 2 7 372.937 53.5989 4
8 -2 -6 3.00678 55.7258 5
-8 2 6 62.2026 50.4934 4
8 -2 -5 126.540 57.7844 5
-8 2 4-1.48350 53.7079 2
8 -2 -4-7.24440 60.9410 5
-8 2 3 227.340 56.4779 2
8 -2 -3 221.432 63.2155 5
-8 2 2-14.8763 55.3226 2
8 -2 -2-45.4852 62.7195 5
-8 2 1 114.249 58.3783 2
8 -2 -1 112.823 66.1108 5
-8 2 0 271.519 59.8046 2
-8 2 -1 2.68442 56.3637 2
-8 2 -2 110.388 49.4725 2
8 -2 2 187.218 58.1269 1
8 -2 3-6.14854 58.5568 1
8 -2 4 67.6049 63.5101 1
8 -2 5-62.4515 66.9192 1
-8 1 11 27.7902 63.8366 4
-8 1 10-96.0443 57.0224 4
-8 1 9 125.442 57.5147 4
-8 1 8 33.2667 49.3617 4
-8 1 7-41.7662 59.4010 2
-8 1 6 64.9971 59.7304 2
-8 1 5 327.029 64.8709 2
-8 1 4 254.005 61.1445 2
-8 1 3 108.103 54.4067 2
-8 1 2 215.712 60.3084 2
-8 1 1 228.083 62.6954 2
-8 1 0 51.3938 56.8432 2
-8 1 -1-8.57195 56.7783 2
8 -1 1-17.7716 56.3679 1
-8 1 -2 4.53747 51.8790 2
8 -1 2 86.1082 63.8628 1
8 -1 3-26.3693 61.3359 1
8 -1 4 41.6460 61.4814 1
-8 0 11 5.61462 60.2370 4
-8 0 10 33.8883 58.6218 4
-8 0 9 31.7513 60.5004 2
-8 0 9 185.841 55.5790 4
-8 0 8 66.9862 54.2003 2
-8 0 7 13.0405 56.1646 2
-8 0 6 170.109 59.0802 2
-8 0 5 9.76846 50.8184 2
-8 0 4 48.9989 56.2410 2
-8 0 3 73.3672 58.9590 2
-8 0 2 35.7585 60.5098 2
-8 0 1 141.160 57.5004 2
8 0 -1 32.4279 57.3727 1
-8 0 0 23.7628 58.3635 2
8 0 0 57.4402 59.5997 1
-8 0 -1-25.1806 64.3924 2
8 0 1 2.13965 57.0770 1
-8 0 -2-3.09463 52.6892 2
8 0 2 54.8417 66.6815 1
-8 0 -3-27.1012 63.1123 2
-8 -1 11 82.1571 52.6338 4
-8 -1 9 67.1383 55.9158 2
-8 -1 8 37.6795 55.1499 2
-8 -1 7-23.1070 54.5992 2
-8 -1 6 113.396 62.5331 2
-8 -1 5 34.4214 54.7151 2
-8 -1 4 66.6752 61.9797 2
-8 -1 3 15.6997 57.4012 2
-8 -1 2 31.4860 66.4950 2
-8 -1 2 115.434 58.3139 1
-8 -1 1 80.1986 67.0632 2
8 1 -1 76.8124 62.5276 1
-8 -1 0 77.7772 64.4240 2
8 1 0 5.87069 61.3565 1
-8 -2 3 47.1375 55.5875 1
-8 -2 2 45.3151 62.6111 1
9 -7 -6 67.1795 74.9039 5
9 -7 -5 24.7178 72.7432 5
9 -7 -4 9.69452 70.9659 5
9 -6 -6 3.56292 70.4881 5
9 -6 -5-36.3283 68.8189 5
-9 6 5-79.3554 50.9610 4
9 -6 -4-35.2098 70.5102 5
9 -6 -3 87.9597 69.4303 5
9 -6 -2-0.60774 74.4368 5
9 -6 -1 1.02390 75.3886 5
-9 5 7 120.630 60.4444 4
-9 5 6-20.2037 58.0171 4
9 -5 -5 96.4854 68.9545 5
-9 5 5 1.07609 49.4968 4
9 -5 -4 188.832 71.2309 5
-9 5 4-11.5362 56.8146 4
9 -5 -3 22.5358 69.4165 5
9 -5 -2-24.9917 73.5253 5
9 -5 -1 74.4821 71.5027 5
-9 4 7 164.691 64.0346 4
-9 4 6 24.1526 56.0078 4
9 -4 -5 13.0867 65.0114 5
9 -4 -4-55.3753 62.2160 5
9 -4 -3 22.5858 68.2415 5
9 -4 -2 97.3772 66.2203 5
9 -4 -1 34.5010 68.2994 5
-9 3 8 10.1771 58.0226 4
-9 3 7 129.042 59.3871 4
9 -3 -5 77.6935 66.1104 5
9 -3 -4 115.717 61.0371 5
9 -3 -3 46.4960 64.7550 5
9 -3 -2 52.9529 69.1261 5
-9 3 -1 4.18228 56.5157 2
;
_shelx_hkl_checksum 45756
_shelx_res_file
;
TITL TK9 P-1
shelx.res
created by SHELXL-2018/3 at 14:11:01 on 26-Mar-2023
CELL 0.71073 7.257 9.7772 14.202 102.101 99.534 110.981
ZERR 2 0.0005 0.0006 0.001 0.006 0.006 0.006
LATT 1
SFAC C H Br N O
UNIT 34 38 2 6 9
OMIT -2 3 4
OMIT 0 1 1
OMIT 1 0 0
OMIT 1 -2 2
OMIT 0 -4 2
OMIT 1 -3 1
OMIT 4 -9 9
OMIT 0 -3 2
LIST 4
SIZE 0.36 0.32 0.2
L.S. 25
acta
conf
bond $h
htab
HTAB N2 O3
EQIV $1 -x+1, -y, -z
HTAB N2 O4_$1
EQIV $2 -x, -y+1, -z+1
HTAB C2 O2_$2
EQIV $3 x-1, y, z
HTAB C7 Br1_$3
HTAB C10 O1W_$1
DFIX 0.86 N2 H2a N2 H2b
dfix 0.82 o1w h1w1 o1w h1w2
dfix 1.297 h1w1 h1w2
WGHT 0.044400
FVAR 2.31973
O1 5 0.447217 0.908840 0.577155 11.00000 0.09753 0.05867 =
0.08418 -0.00548 0.03684 0.01906
O2 5 0.146574 0.736009 0.538129 11.00000 0.07767 0.08704 =
0.11949 0.00091 0.05019 0.03327
N1 4 0.548986 0.380929 0.279231 11.00000 0.04150 0.03243 =
0.05680 0.00929 0.01462 0.01093
N2 4 0.625891 0.187253 0.123014 11.00000 0.04706 0.04232 =
0.04902 0.00802 0.00686 0.02364
H2A 2 0.686011 0.132240 0.101505 11.00000 -1.20000
H2B 2 0.555916 0.197628 0.070042 11.00000 -1.20000
N3 4 0.321790 0.781799 0.531256 11.00000 0.06993 0.05743 =
0.05110 0.01192 0.02222 0.02611
C1 1 0.379726 0.678802 0.465245 11.00000 0.05234 0.04533 =
0.03978 0.01427 0.01209 0.02277
C2 1 0.248689 0.527623 0.424459 11.00000 0.04454 0.05158 =
0.06659 0.01768 0.02287 0.01647
AFIX 43
H2 2 0.123215 0.491207 0.439437 11.00000 -1.20000
AFIX 0
C3 1 0.301523 0.430368 0.362003 11.00000 0.04351 0.03822 =
0.06698 0.01123 0.01590 0.01080
AFIX 43
H3 2 0.209824 0.328530 0.333702 11.00000 -1.20000
AFIX 0
C4 1 0.491018 0.480631 0.339575 11.00000 0.03840 0.03573 =
0.04521 0.01490 0.00675 0.01477
C5 1 0.620427 0.635714 0.382730 11.00000 0.04127 0.03722 =
0.06300 0.01051 0.01630 0.01002
AFIX 43
H5 2 0.746350 0.673689 0.368381 11.00000 -1.20000
AFIX 0
C6 1 0.567495 0.732636 0.445081 11.00000 0.05058 0.03783 =
0.05242 0.00660 0.00829 0.01208
AFIX 43
H6 2 0.657730 0.834750 0.473932 11.00000 -1.20000
AFIX 0
C7 1 0.393548 0.230574 0.220126 11.00000 0.05201 0.04035 =
0.07624 0.00391 0.02934 0.00407
AFIX 23
H7A 2 0.307731 0.241586 0.164666 11.00000 -1.20000
H7B 2 0.307496 0.187484 0.261102 11.00000 -1.20000
AFIX 0
C8 1 0.484679 0.123196 0.180647 11.00000 0.08836 0.03655 =
0.07350 0.01106 0.03815 0.01605
AFIX 23
H8A 2 0.557431 0.102503 0.235884 11.00000 -1.20000
H8B 2 0.376210 0.026977 0.138441 11.00000 -1.20000
AFIX 0
C9 1 0.785605 0.334873 0.185220 11.00000 0.05092 0.05485 =
0.10118 -0.01553 0.02618 0.00948
AFIX 23
H9A 2 0.874756 0.378980 0.145729 11.00000 -1.20000
H9B 2 0.867453 0.319121 0.239824 11.00000 -1.20000
AFIX 0
C10 1 0.699093 0.443801 0.226512 11.00000 0.07470 0.03698 =
0.12502 0.00782 0.06076 0.01025
AFIX 23
H10A 2 0.809491 0.536313 0.271886 11.00000 -1.20000
H10B 2 0.635383 0.471694 0.172320 11.00000 -1.20000
AFIX 0
BR1 3 0.926102 -0.008325 0.319669 11.00000 0.08551 0.05620 =
0.05928 0.01687 0.03290 0.02352
O3 5 0.848776 0.026279 0.092689 11.00000 0.10373 0.07592 =
0.09667 0.04215 0.04189 0.06720
O4 5 0.615611 -0.212484 0.033021 11.00000 0.06859 0.10808 =
0.08622 0.03224 -0.00210 0.04925
C11 1 0.937909 -0.168509 0.128925 11.00000 0.04352 0.03830 =
0.05008 0.01538 0.00890 0.01725
C12 1 1.013536 -0.130379 0.230868 11.00000 0.04788 0.03785 =
0.05379 0.01940 0.01353 0.01262
C13 1 1.153637 -0.182703 0.271516 11.00000 0.05691 0.05347 =
0.06246 0.02362 0.00092 0.01414
AFIX 43
H13 2 1.201561 -0.157757 0.340436 11.00000 -1.20000
AFIX 0
C14 1 1.220450 -0.270098 0.210717 11.00000 0.05300 0.05699 =
0.09417 0.03178 0.00375 0.02712
AFIX 43
H14 2 1.316352 -0.303199 0.238116 11.00000 -1.20000
AFIX 0
C15 1 1.147144 -0.310185 0.108579 11.00000 0.05835 0.05077 =
0.08784 0.01801 0.02015 0.03204
AFIX 43
H15 2 1.193664 -0.369875 0.067067 11.00000 -1.20000
AFIX 0
C16 1 1.004788 -0.261481 0.068298 11.00000 0.05641 0.05324 =
0.05542 0.01065 0.01082 0.02885
AFIX 43
H16 2 0.952495 -0.291267 -0.000611 11.00000 -1.20000
AFIX 0
C17 1 0.789515 -0.112092 0.081708 11.00000 0.06741 0.07551 =
0.05073 0.02576 0.02269 0.04936
PART -1
AFIX 6
O1W 5 0.550831 -0.520242 -0.066208 10.50000 0.11754 0.09626 =
0.19692 0.04587 0.04371 0.03644
H1W1 2 0.435882 -0.430124 -0.060307 10.50000 -1.50000
H1W2 2 0.458306 -0.629327 -0.042348 10.50000 -1.50000
PART 0
AFIX 0
HKLF 4
REM TK9 P-1
REM wR2 = 0.0843, GooF = S = 0.944, Restrained GooF = 1.234 for all data
REM R1 = 0.0360 for 2478 Fo > 4sig(Fo) and 0.0692 for all 3856 data
REM 244 parameters refined using 5 restraints
END
WGHT 0.0443 0.0000
REM Instructions for potential hydrogen bonds
HTAB N2 O3
HTAB N2 O4_$1
HTAB C2 O2_$2
HTAB C3 Br1_$3
HTAB C7 Br1_$3
HTAB C10 O1W_$1
REM Highest difference peak 0.508, deepest hole -0.326, 1-sigma level 0.047
Q1 1 1.0123 -0.0546 0.3158 11.00000 0.05 0.51
Q2 1 0.7933 -0.0592 0.2993 11.00000 0.05 0.26
Q3 1 0.7437 0.5432 0.2176 11.00000 0.05 0.22
Q4 1 0.6407 0.4015 0.2735 11.00000 0.05 0.21
Q5 1 0.9347 0.1078 0.2836 11.00000 0.05 0.21
Q6 1 0.8850 -0.1200 0.3131 11.00000 0.05 0.19
Q7 1 0.6995 -0.1959 0.0007 11.00000 0.05 0.19
Q8 1 1.0392 -0.1056 0.1755 11.00000 0.05 0.18
Q9 1 0.4561 0.7076 0.4462 11.00000 0.05 0.18
Q10 1 1.0882 -0.1397 0.2513 11.00000 0.05 0.18
Q11 1 0.7215 0.2590 0.1713 11.00000 0.05 0.17
Q12 1 0.9214 -0.1840 0.1732 11.00000 0.05 0.17
Q13 1 1.0231 -0.1691 0.1113 11.00000 0.05 0.17
Q14 1 0.3633 0.4964 0.3265 11.00000 0.05 0.17
Q15 1 0.3180 0.6161 0.4196 11.00000 0.05 0.17
Q16 1 0.5373 0.3120 0.2915 11.00000 0.05 0.17
Q17 1 0.4058 -0.4838 -0.0239 11.00000 0.05 0.16
Q18 1 0.4399 0.2024 0.1849 11.00000 0.05 0.16
Q19 1 0.2417 0.0147 0.0394 11.00000 0.05 0.16
Q20 1 0.9584 -0.0390 0.2535 11.00000 0.05 0.16
;
_shelx_res_checksum 64215
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.4472(3) 0.9088(2) 0.57716(16) 0.0866(7) Uani d 1 . .
O O2 0.1466(4) 0.7360(3) 0.53813(19) 0.0965(8) Uani d 1 . .
N N1 0.5490(3) 0.3809(2) 0.27923(14) 0.0452(5) Uani d 1 . .
N N2 0.6259(3) 0.1873(2) 0.12301(15) 0.0462(5) Uani d 1 . .
H H2A 0.686(3) 0.132(3) 0.1015(18) 0.055 Uiso d 1 . .
H H2B 0.556(3) 0.198(3) 0.0700(14) 0.055 Uiso d 1 . .
N N3 0.3218(4) 0.7818(3) 0.53126(16) 0.0593(6) Uani d 1 . .
C C1 0.3797(4) 0.6788(3) 0.46525(17) 0.0447(6) Uani d 1 . .
C C2 0.2487(4) 0.5276(3) 0.4245(2) 0.0540(7) Uani d 1 . .
H H2 0.123215 0.491207 0.439437 0.065 Uiso calc 1 . .
C C3 0.3015(4) 0.4304(3) 0.36200(19) 0.0518(6) Uani d 1 . .
H H3 0.209824 0.328530 0.333702 0.062 Uiso calc 1 . .
C C4 0.4910(3) 0.4806(2) 0.33958(16) 0.0399(5) Uani d 1 . .
C C5 0.6204(4) 0.6357(3) 0.38273(19) 0.0493(6) Uani d 1 . .
H H5 0.746350 0.673689 0.368381 0.059 Uiso calc 1 . .
C C6 0.5675(4) 0.7326(3) 0.44508(18) 0.0505(6) Uani d 1 . .
H H6 0.657730 0.834750 0.473932 0.061 Uiso calc 1 . .
C C7 0.3935(4) 0.2306(3) 0.2201(2) 0.0611(8) Uani d 1 . .
H H7A 0.307731 0.241586 0.164666 0.073 Uiso calc 1 . .
H H7B 0.307496 0.187484 0.261102 0.073 Uiso calc 1 . .
C C8 0.4847(5) 0.1232(3) 0.1806(2) 0.0676(8) Uani d 1 . .
H H8A 0.557431 0.102503 0.235884 0.081 Uiso calc 1 . .
H H8B 0.376210 0.026977 0.138441 0.081 Uiso calc 1 . .
C C9 0.7856(4) 0.3349(3) 0.1852(2) 0.0781(10) Uani d 1 . .
H H9A 0.874756 0.378980 0.145729 0.094 Uiso calc 1 . .
H H9B 0.867453 0.319121 0.239824 0.094 Uiso calc 1 . .
C C10 0.6991(5) 0.4438(3) 0.2265(3) 0.0808(10) Uani d 1 . .
H H10A 0.809491 0.536313 0.271886 0.097 Uiso calc 1 . .
H H10B 0.635383 0.471694 0.172320 0.097 Uiso calc 1 . .
Br Br1 0.92610(5) -0.00832(3) 0.31967(2) 0.06679(14) Uani d 1 . .
O O3 0.8488(3) 0.0263(3) 0.09269(16) 0.0782(6) Uani d 1 . .
O O4 0.6156(3) -0.2125(3) 0.03302(17) 0.0860(7) Uani d 1 . .
C C11 0.9379(3) -0.1685(3) 0.12893(18) 0.0438(6) Uani d 1 . .
C C12 1.0135(4) -0.1304(3) 0.23087(19) 0.0469(6) Uani d 1 . .
C C13 1.1536(4) -0.1827(3) 0.2715(2) 0.0609(7) Uani d 1 . .
H H13 1.201561 -0.157757 0.340436 0.073 Uiso calc 1 . .
C C14 1.2204(4) -0.2701(3) 0.2107(3) 0.0671(8) Uani d 1 . .
H H14 1.316352 -0.303199 0.238116 0.080 Uiso calc 1 . .
C C15 1.1471(4) -0.3102(3) 0.1086(2) 0.0630(8) Uani d 1 . .
H H15 1.193664 -0.369875 0.067067 0.076 Uiso calc 1 . .
C C16 1.0048(4) -0.2615(3) 0.0683(2) 0.0545(7) Uani d 1 . .
H H16 0.952495 -0.291267 -0.000611 0.065 Uiso calc 1 . .
C C17 0.7895(5) -0.1121(4) 0.0817(2) 0.0564(7) Uani d 1 . .
O O1W 0.5508(9) -0.5202(7) -0.0662(6) 0.138(2) Uani d 0.5 A -1
H H1W1 0.435882 -0.430124 -0.060307 0.207 Uiso d 0.5 A -1
H H1W2 0.458306 -0.629327 -0.042348 0.207 Uiso d 0.5 A -1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0975(16) 0.0587(13) 0.0842(15) 0.0191(13) 0.0368(13) -0.0055(11)
O2 0.0777(15) 0.0870(16) 0.1195(19) 0.0333(13) 0.0502(15) 0.0009(14)
N1 0.0415(11) 0.0324(10) 0.0568(12) 0.0109(9) 0.0146(10) 0.0093(9)
N2 0.0471(13) 0.0423(12) 0.0490(12) 0.0236(10) 0.0069(10) 0.0080(10)
N3 0.0699(17) 0.0574(15) 0.0511(13) 0.0261(14) 0.0222(13) 0.0119(11)
C1 0.0523(15) 0.0453(14) 0.0398(13) 0.0228(13) 0.0121(12) 0.0143(11)
C2 0.0445(14) 0.0516(15) 0.0666(17) 0.0165(13) 0.0229(13) 0.0177(13)
C3 0.0435(15) 0.0382(13) 0.0670(17) 0.0108(12) 0.0159(13) 0.0112(12)
C4 0.0384(13) 0.0357(12) 0.0452(13) 0.0148(11) 0.0067(11) 0.0149(10)
C5 0.0413(14) 0.0372(13) 0.0630(16) 0.0100(11) 0.0163(12) 0.0105(12)
C6 0.0506(15) 0.0378(13) 0.0524(15) 0.0121(12) 0.0083(13) 0.0066(11)
C7 0.0520(16) 0.0403(14) 0.0762(18) 0.0041(13) 0.0293(15) 0.0039(13)
C8 0.088(2) 0.0366(14) 0.0735(18) 0.0160(15) 0.0382(17) 0.0111(13)
C9 0.0509(17) 0.0548(17) 0.101(2) 0.0095(14) 0.0262(17) -0.0155(16)
C10 0.075(2) 0.0370(15) 0.125(3) 0.0103(14) 0.061(2) 0.0078(16)
Br1 0.0855(2) 0.05620(19) 0.05928(19) 0.02352(16) 0.03290(16) 0.01687(13)
O3 0.1037(16) 0.0759(15) 0.0967(15) 0.0672(14) 0.0419(13) 0.0421(12)
O4 0.0686(14) 0.1081(18) 0.0862(15) 0.0493(15) -0.0021(13) 0.0322(14)
C11 0.0435(13) 0.0383(13) 0.0501(14) 0.0172(11) 0.0089(12) 0.0154(11)
C12 0.0479(14) 0.0379(13) 0.0538(15) 0.0126(12) 0.0135(12) 0.0194(11)
C13 0.0569(17) 0.0535(16) 0.0625(17) 0.0141(15) 0.0009(15) 0.0236(14)
C14 0.0530(17) 0.0570(18) 0.094(2) 0.0271(15) 0.0038(17) 0.0318(17)
C15 0.0583(17) 0.0508(16) 0.088(2) 0.0320(15) 0.0202(16) 0.0180(15)
C16 0.0564(16) 0.0532(16) 0.0554(15) 0.0288(14) 0.0108(13) 0.0107(13)
C17 0.067(2) 0.076(2) 0.0507(15) 0.0494(18) 0.0227(15) 0.0258(15)
O1W 0.118(4) 0.096(4) 0.197(7) 0.036(4) 0.044(4) 0.046(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N1 C10 . . 118.22(18) ?
C4 N1 C7 . . 118.65(17) ?
C10 N1 C7 . . 112.0(2) ?
C9 N2 C8 . . 109.6(2) ?
C9 N2 H2A . . 106.7(16) ?
C8 N2 H2A . . 114.7(17) ?
C9 N2 H2B . . 110.9(17) ?
C8 N2 H2B . . 108.5(16) ?
H2A N2 H2B . . 106(2) ?
O1 N3 O2 . . 122.2(2) ?
O1 N3 C1 . . 119.5(2) ?
O2 N3 C1 . . 118.3(2) ?
C2 C1 C6 . . 120.1(2) ?
C2 C1 N3 . . 119.9(2) ?
C6 C1 N3 . . 120.0(2) ?
C3 C2 C1 . . 120.2(2) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C2 C3 C4 . . 121.4(2) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
N1 C4 C5 . . 121.73(19) ?
N1 C4 C3 . . 121.6(2) ?
C5 C4 C3 . . 116.6(2) ?
C6 C5 C4 . . 121.9(2) ?
C6 C5 H5 . . 119.0 ?
C4 C5 H5 . . 119.0 ?
C5 C6 C1 . . 119.7(2) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
N1 C7 C8 . . 112.2(2) ?
N1 C7 H7A . . 109.2 ?
C8 C7 H7A . . 109.2 ?
N1 C7 H7B . . 109.2 ?
C8 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
N2 C8 C7 . . 111.3(2) ?
N2 C8 H8A . . 109.4 ?
C7 C8 H8A . . 109.4 ?
N2 C8 H8B . . 109.4 ?
C7 C8 H8B . . 109.4 ?
H8A C8 H8B . . 108.0 ?
N2 C9 C10 . . 112.0(2) ?
N2 C9 H9A . . 109.2 ?
C10 C9 H9A . . 109.2 ?
N2 C9 H9B . . 109.2 ?
C10 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
N1 C10 C9 . . 112.8(2) ?
N1 C10 H10A . . 109.0 ?
C9 C10 H10A . . 109.0 ?
N1 C10 H10B . . 109.0 ?
C9 C10 H10B . . 109.0 ?
H10A C10 H10B . . 107.8 ?
C12 C11 C16 . . 118.0(2) ?
C12 C11 C17 . . 122.6(2) ?
C16 C11 C17 . . 119.3(2) ?
C11 C12 C13 . . 120.8(2) ?
C11 C12 Br1 . . 121.09(19) ?
C13 C12 Br1 . . 118.1(2) ?
C14 C13 C12 . . 120.0(3) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C13 C14 C15 . . 120.4(3) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C16 C15 C14 . . 119.7(3) ?
C16 C15 H15 . . 120.2 ?
C14 C15 H15 . . 120.2 ?
C15 C16 C11 . . 121.0(3) ?
C15 C16 H16 . . 119.5 ?
C11 C16 H16 . . 119.5 ?
O3 C17 O4 . . 126.0(3) ?
O3 C17 C11 . . 117.9(3) ?
O4 C17 C11 . . 116.2(3) ?
H1W1 O1W H1W2 . . 105.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N3 . 1.204(3) ?
O2 N3 . 1.216(3) ?
N1 C4 . 1.387(3) ?
N1 C10 . 1.452(3) ?
N1 C7 . 1.456(3) ?
N2 C9 . 1.461(3) ?
N2 C8 . 1.465(3) ?
N2 H2A . 0.846(16) ?
N2 H2B . 0.881(16) ?
N3 C1 . 1.452(3) ?
C1 C2 . 1.370(3) ?
C1 C6 . 1.376(3) ?
C2 C3 . 1.363(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.400(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.399(3) ?
C5 C6 . 1.361(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.492(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.487(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
Br1 C12 . 1.896(2) ?
O3 C17 . 1.230(3) ?
O4 C17 . 1.254(3) ?
C11 C12 . 1.378(3) ?
C11 C16 . 1.389(3) ?
C11 C17 . 1.502(4) ?
C12 C13 . 1.389(4) ?
C13 C14 . 1.355(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.377(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.375(4) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
O1W H1W1 . 1.4134 ?
O1W H1W2 . 1.1905 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2A O3 . 0.846(16) 1.832(18) 2.655(3) 164(2) yes
N2 H2B O4 2_655 0.881(16) 1.824(17) 2.701(3) 173(2) yes
C2 H2 O2 2_566 0.93 2.50 3.307(4) 145.1 yes
C7 H7B Br1 1_455 0.97 3.11 4.032(2) 160.1 yes
C10 H10B O1W 2_655 0.97 2.10 3.057(8) 169.1 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 N3 C1 C2 . . . . 170.2(3) ?
O2 N3 C1 C2 . . . . -9.8(4) ?
O1 N3 C1 C6 . . . . -8.7(4) ?
O2 N3 C1 C6 . . . . 171.2(3) ?
C6 C1 C2 C3 . . . . -1.4(4) ?
N3 C1 C2 C3 . . . . 179.7(2) ?
C1 C2 C3 C4 . . . . 1.4(4) ?
C10 N1 C4 C5 . . . . -26.0(3) ?
C7 N1 C4 C5 . . . . -167.1(2) ?
C10 N1 C4 C3 . . . . 155.3(3) ?
C7 N1 C4 C3 . . . . 14.2(3) ?
C2 C3 C4 N1 . . . . 177.4(2) ?
C2 C3 C4 C5 . . . . -1.3(4) ?
N1 C4 C5 C6 . . . . -177.4(2) ?
C3 C4 C5 C6 . . . . 1.4(4) ?
C4 C5 C6 C1 . . . . -1.4(4) ?
C2 C1 C6 C5 . . . . 1.4(4) ?
N3 C1 C6 C5 . . . . -179.6(2) ?
C4 N1 C7 C8 . . . . -165.1(2) ?
C10 N1 C7 C8 . . . . 51.5(3) ?
C9 N2 C8 C7 . . . . 57.1(3) ?
N1 C7 C8 N2 . . . . -55.5(3) ?
C8 N2 C9 C10 . . . . -56.2(3) ?
C4 N1 C10 C9 . . . . 165.9(2) ?
C7 N1 C10 C9 . . . . -50.6(4) ?
N2 C9 C10 N1 . . . . 53.6(4) ?
C16 C11 C12 C13 . . . . 0.5(4) ?
C17 C11 C12 C13 . . . . -178.8(2) ?
C16 C11 C12 Br1 . . . . -178.41(17) ?
C17 C11 C12 Br1 . . . . 2.4(3) ?
C11 C12 C13 C14 . . . . 1.2(4) ?
Br1 C12 C13 C14 . . . . -179.9(2) ?
C12 C13 C14 C15 . . . . -1.3(4) ?
C13 C14 C15 C16 . . . . -0.2(4) ?
C14 C15 C16 C11 . . . . 1.9(4) ?
C12 C11 C16 C15 . . . . -2.0(4) ?
C17 C11 C16 C15 . . . . 177.2(3) ?
C12 C11 C17 O3 . . . . 65.2(3) ?
C16 C11 C17 O3 . . . . -114.1(3) ?
C12 C11 C17 O4 . . . . -115.8(3) ?
C16 C11 C17 O4 . . . . 64.9(3) ?