#------------------------------------------------------------------------------
#$Date: 2022-11-08 20:40:13 +0100 (Tue, 08 Nov 2022) $
#$Revision: 279111 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/26/2022674.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_2022674
loop_
_publ_author_name
'W\'ojcicka, Anna'
'Becan, Lilianna'
'Rembia\/lkowska, Nina'
'Pyra, Anna'
'Bryndal, Iwona'
_publ_section_title
;
Structure and cytotoxic properties of
1-hydroxy-5-methyl-7-phenylpyrido[3,4-d]pyridazin-4(3H)-one
and its mono- and disubstituted ethyl acetates
;
_journal_coeditor_code QF3056
_journal_issue 10
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first 559
_journal_page_last 569
_journal_paper_doi 10.1107/S2053229622009202
_journal_volume 78
_journal_year 2022
_chemical_formula_iupac 'C22 H23 N3 O6'
_chemical_formula_moiety 'C22 H23 N3 O6'
_chemical_formula_sum 'C22 H23 N3 O6'
_chemical_formula_weight 425.43
_chemical_name_systematic
;Ethyl
[(5-methyl-4-oxo-7-phenyl-3,4-dihydropyrido[3,4-d]pyridazin-1-yl)oxy]acetate
;
_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 geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-2018/1
_cell_angle_alpha 92.24(2)
_cell_angle_beta 106.06(3)
_cell_angle_gamma 109.46(3)
_cell_formula_units_Z 2
_cell_length_a 8.679(2)
_cell_length_b 8.751(2)
_cell_length_c 15.137(4)
_cell_measurement_reflns_used 1514
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 72.4
_cell_measurement_theta_min 3.1
_cell_volume 1030.7(5)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2014)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature 100(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type 'Rigaku Xcalibur Onyx'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0681
_diffrn_reflns_av_unetI/netI 0.1079
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 7128
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 77.255
_diffrn_reflns_theta_min 3.070
_diffrn_source 'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu 0.841
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.83993
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.371
_exptl_crystal_description needle
_exptl_crystal_F_000 448
_exptl_crystal_size_max 0.090
_exptl_crystal_size_mid 0.030
_exptl_crystal_size_min 0.020
_refine_diff_density_max 0.345
_refine_diff_density_min -0.385
_refine_ls_extinction_coef 0.0037(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref 0.984
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 284
_refine_ls_number_reflns 4142
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.984
_refine_ls_R_factor_all 0.1030
_refine_ls_R_factor_gt 0.0627
_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^)+(0.0630P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1474
_refine_ls_wR_factor_ref 0.1650
_reflns_number_gt 2089
_reflns_number_total 4142
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file qf3056sup1.cif
_cod_data_source_block 4
_cod_depositor_comments
'Adding full bibliography for 2022672--2022674.cif.'
_cod_database_code 2022674
_cod_database_fobs_code 2022674
_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 0.928
_shelx_estimated_absorpt_t_max 0.983
_shelx_hkl_file
;
0 0 -1 4067.28 46.3594 4
0 0 -2 1399.68 61.9115 4
0 0 -3 5369.93 117.618 4
0 0 -4 346.882 89.3005 4
0 0 -5 2641.41 128.630 4
0 0 -6 2604.21 130.174 4
0 0 -7 1298.81 135.254 4
0 0 -8 0.59776 118.177 4
0 0 -9 3344.64 166.428 4
0 0 -10 134.146 122.532 4
0 0 -11 3007.09 145.142 17
0 0 -11 3239.33 154.490 14
0 0 11 3208.29 124.162 6
0 0 -11 2873.87 195.907 4
0 0 -12 34.0864 128.301 17
0 0 12 41.6211 101.142 6
0 0 -12 25.0250 150.842 4
0 0 -13 560.940 136.813 17
0 0 13 529.684 112.029 6
0 0 14 219.975 110.308 6
0 0 -14 182.813 128.683 17
0 0 15 592.645 112.379 6
0 0 16 175.652 94.8306 6
0 0 17 59.7477 72.8052 6
0 0 18 27.3782 38.8182 6
0 -1 18 49.5401 48.4680 6
0 -1 17 26.0031 82.4036 6
0 -1 16-17.0896 98.2518 6
0 -1 15 945.061 115.012 6
0 -1 14 26.1412 111.944 6
0 -1 13 1538.59 130.052 6
0 1 -13 1232.42 132.494 17
0 1 -12 192.753 116.893 17
0 -1 12 261.132 107.665 6
0 1 -12 332.462 189.409 4
0 1 -11 7.41649 92.2570 17
0 1 -11 26.4034 125.218 14
0 1 -11 32.3824 107.923 12
0 1 -11-6.38154 153.334 4
0 1 -10 1176.99 169.468 4
0 1 -9 641.277 155.696 4
0 1 -8 7169.05 218.721 4
0 1 -7 5335.68 192.498 4
0 1 -6 4630.27 162.153 4
0 1 -5 36.4897 112.293 4
0 1 -4 6723.15 156.515 4
0 1 -4 5920.36 80.2195 0
0 1 -3 1957.32 93.6675 4
0 1 -3 2091.54 65.6593 0
0 1 -2 12947.7 134.830 4
0 1 -2 13752.8 120.374 0
0 1 -2 12588.4 138.408 1
0 1 -1 4899.07 80.9756 1
0 1 -1 4551.95 51.6523 2
0 1 -1 4925.49 76.2814 0
0 1 -1 4530.98 66.0133 4
0 1 0 25387.9 422.628 2
0 1 0 25635.5 604.836 0
0 1 1 9212.57 100.453 0
0 1 1 8778.68 104.566 3
0 -1 -2 14.3790 38.5164 4
0 1 2 23.4000 46.1451 0
0 1 2 17.9061 54.8003 3
0 1 3 71.1942 46.7551 0
0 1 3 47.3662 60.5887 3
0 -1 -3 61.2426 64.3371 4
0 1 4 519.549 75.6339 3
0 -1 -4 500.967 76.7348 4
0 1 4 585.554 37.6983 0
0 -1 -5 4534.18 123.351 4
0 -1 -6 9.76186 84.1105 4
0 1 6 10.4729 67.1747 3
0 1 7 953.900 95.0913 3
0 -1 -7 978.679 102.747 4
0 -1 -8 9.49925 94.8281 4
0 1 8 25.6624 75.6196 3
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0 1 9 76.4897 79.4927 3
0 -1 -10 205.352 111.288 4
0 1 10 325.890 87.6767 3
0 1 11 6332.12 152.625 6
0 -1 -11 6592.83 177.458 17
0 -1 -11 6285.89 175.248 14
0 1 12 378.026 103.944 6
0 -1 -12 355.709 154.997 17
0 -1 -13 69.8149 139.856 17
0 1 13 131.216 102.577 6
0 1 14-8.35779 106.872 6
0 -1 -14 31.3012 141.000 17
0 1 15 122.668 97.8755 6
0 -1 -15 150.327 129.685 17
0 1 16 625.322 87.9691 6
0 1 17 146.391 54.4277 6
0 -2 18 419.585 50.3390 6
0 -2 17-43.0342 78.9315 6
0 -2 16 107.966 94.2774 6
0 -2 15 866.306 120.373 6
0 -2 14-13.1350 109.210 6
0 -2 13 44.9102 107.441 6
0 2 -12 2289.68 243.686 4
0 2 -12 2562.77 169.649 12
0 2 -12 2445.60 205.433 1
0 2 -11 1337.73 204.680 4
0 2 -11 1304.23 144.282 12
0 2 -11 1397.53 166.727 1
0 2 -10 1239.65 158.071 1
0 2 -10 1275.38 171.880 4
0 2 -9 142.311 112.561 1
0 2 -9 89.8642 158.024 4
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0 2 -8 256.626 115.435 1
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0 2 -7 712.558 117.809 1
0 2 -6 1578.85 126.030 1
0 2 -6 1284.55 71.9788 0
0 2 -6 1642.76 147.539 4
0 2 -5 208.883 61.3102 0
0 2 -5 261.466 98.0361 1
0 2 -5 247.663 105.516 4
0 2 -4 78361.3 1576.03 0
0 2 -4 77799.4 1881.88 1
0 2 -4 79122.0 1735.44 4
0 2 -3 115408. 1835.88 4
0 2 -3 119804. 2140.25 1
0 2 -3 120926. 1941.95 0
0 2 -2 54251.2 1067.03 4
0 2 -2 62676.4 1396.43 0
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0 2 -1 50382.3 750.773 2
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0 2 1 3078.35 80.7443 2
0 2 1 3281.98 115.992 0
0 2 2 13223.6 180.147 0
0 2 3 1955.31 91.0726 0
0 2 3 1997.20 101.135 3
0 -2 -3 1401.44 50.4685 4
0 2 4 1858.26 104.115 3
0 -2 -4 1386.76 63.0197 4
0 2 4 1867.47 83.1232 0
0 2 5 1483.48 101.678 3
0 2 5 1163.56 64.4121 0
0 -2 -5 1023.32 68.3954 4
0 -2 -6 2856.42 101.224 4
0 2 6 3813.47 143.206 3
0 -2 -7 2281.30 106.368 4
0 2 7 3274.68 142.928 3
0 2 8 31.7393 78.4097 3
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0 2 10 973.244 110.545 3
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0 2 11 1028.21 175.627 2
0 -2 -11 1060.64 166.144 17
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0 2 13 671.981 102.626 6
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0 6 -4-77.2307 138.434 9
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0 6 -3 392.574 135.752 9
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0 6 -2 464.916 166.173 0
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0 6 2 4548.93 231.181 0
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0 6 4 3277.90 187.934 0
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0 6 5 20649.2 266.677 7
0 6 6 563.722 134.227 7
0 6 7 18.2989 133.700 7
0 -6 -8 684.784 107.592 17
0 6 8 1031.92 139.215 7
0 -6 -9 521.900 106.231 17
0 6 9 649.702 126.941 7
0 6 10 455.058 109.717 7
0 -6 -10 423.577 99.5743 17
0 -6 -11 9.63366 86.0124 17
0 6 11 57.8356 81.9853 7
0 -6 -12 55.1904 64.5476 17
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0 7 -8 828.235 144.071 5
0 7 -7 346.069 155.132 9
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0 7 -7 224.747 129.376 20
0 7 -6 601.323 148.927 9
0 7 -6 676.093 163.202 5
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0 7 -4-11.1343 154.314 5
0 7 -4-49.0092 169.149 9
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;
_shelx_hkl_checksum 27511
_shelx_res_file
;
TITL PM13 in P-1
4.res
created by SHELXL-2018/1 at 09:27:57 on 21-Jun-2022
REM P-1 (#2 in standard setting)
CELL 1.54184 8.679 8.751 15.137 92.24 106.06 109.46
ZERR 2.00 0.002 0.002 0.004 0.02 0.03 0.03
LATT 1
SFAC C H N O
UNIT 44.00 46.00 6.00 12.00
temp -173
ACTA
size 0.09 0.03 0.02
L.S. 4
BOND $H
FMAP 2
htab 2.1
conf
EQIV $1 x-1, y, z
HTAB C11 O4_$1
EQIV $2 -x, -y+1, -z
HTAB C13 O32_$2
HTAB C14 O12
EQIV $3 -x+1, -y+1, -z
HTAB C33 O32_$3
HTAB C33 O12_$2
EQIV $4 -x+1, -y+2, -z+1
HTAB C73 O12_$4
PLAN 30
mpla 8 C1 O1 C11 C12 O12 O13 C13 C14
mpla 10 C1 N2 N3 C4 C10 C9 C8 C7 N6 C5 C51 O1 O4 C31
MPLA 6 C71 C72 C73 C74 C75 C76
mpla 10 C1 N2 N3 C4 C10 C9 C8 C7 N6 C5
mpla 7 N3 C31 C32 O32 O33 C33 C34
WGHT 0.063000
EXTI 0.003670
FVAR 2.51215
C1 1 0.261971 0.460547 0.341007 11.00000 0.02631 0.03016 =
0.02478 0.00754 0.01182 0.01264
O1 4 0.115351 0.454032 0.358411 11.00000 0.01883 0.03661 =
0.02845 0.00133 0.00853 0.00929
C11 1 -0.036176 0.325561 0.301371 11.00000 0.01840 0.02823 =
0.02962 -0.00132 0.00236 0.00401
AFIX 23
H111 2 -0.131455 0.312960 0.327715 11.00000 -1.20000
H112 2 -0.015212 0.221076 0.301129 11.00000 -1.20000
AFIX 0
C12 1 -0.087357 0.361883 0.202392 11.00000 0.01452 0.03093 =
0.03315 -0.00065 0.00438 0.00787
O12 4 -0.031715 0.489122 0.176692 11.00000 0.03067 0.02210 =
0.03938 0.00563 0.00835 0.00678
C13 1 -0.266653 0.238300 0.050078 11.00000 0.03545 0.04712 =
0.03525 -0.00074 0.00190 0.01293
AFIX 23
H131 2 -0.284006 0.343818 0.042431 11.00000 -1.20000
H132 2 -0.377843 0.148709 0.019592 11.00000 -1.20000
AFIX 0
O13 4 -0.209351 0.225890 0.148443 11.00000 0.03045 0.02993 =
0.03244 -0.00147 0.00708 0.00408
C14 1 -0.135951 0.227603 0.004619 11.00000 0.05180 0.07299 =
0.03643 -0.00152 0.01123 0.01959
AFIX 137
H141 2 -0.025470 0.315251 0.035544 11.00000 -1.50000
H142 2 -0.174650 0.239485 -0.061125 11.00000 -1.50000
H143 2 -0.122656 0.121111 0.009848 11.00000 -1.50000
AFIX 0
N2 3 0.256282 0.360126 0.274897 11.00000 0.02435 0.03244 =
0.02544 0.00695 0.01039 0.01498
N3 3 0.409583 0.372420 0.261498 11.00000 0.02290 0.02946 =
0.02504 0.00342 0.00910 0.01112
C31 1 0.387617 0.264936 0.180251 11.00000 0.03247 0.02962 =
0.03022 0.00642 0.01251 0.01497
AFIX 23
H311 2 0.294619 0.158906 0.175297 11.00000 -1.20000
H312 2 0.494912 0.243630 0.186311 11.00000 -1.20000
AFIX 0
C32 1 0.343358 0.342321 0.093686 11.00000 0.02571 0.02410 =
0.02660 0.00208 0.00835 0.00719
O32 4 0.348786 0.482362 0.093548 11.00000 0.03987 0.03069 =
0.03263 0.00569 0.01043 0.01393
C33 1 0.256617 0.299089 -0.070180 11.00000 0.03904 0.03685 =
0.02891 0.00642 0.01064 0.01666
AFIX 23
H331 2 0.355936 0.394237 -0.072688 11.00000 -1.20000
H332 2 0.157605 0.334695 -0.076461 11.00000 -1.20000
AFIX 0
O33 4 0.298422 0.234912 0.017990 11.00000 0.03807 0.02807 =
0.02719 0.00217 0.00939 0.01553
C34 1 0.213623 0.163969 -0.146404 11.00000 0.08926 0.06675 =
0.03037 0.00689 0.01026 0.04798
AFIX 137
H341 2 0.190424 0.204147 -0.206420 11.00000 -1.50000
H342 2 0.111686 0.072779 -0.145100 11.00000 -1.50000
H343 2 0.310542 0.126304 -0.137717 11.00000 -1.50000
AFIX 0
C4 1 0.569317 0.483591 0.310981 11.00000 0.02203 0.03109 =
0.02470 0.00576 0.00274 0.00993
O4 4 0.696916 0.486124 0.288657 11.00000 0.02547 0.04592 =
0.04568 -0.00002 0.01673 0.01407
C5 1 0.725974 0.709140 0.449715 11.00000 0.02948 0.03335 =
0.02773 0.01021 0.01075 0.01217
C51 1 0.901891 0.728698 0.444443 11.00000 0.02494 0.04868 =
0.03769 0.00200 0.01075 0.01049
AFIX 137
H511 2 0.909036 0.754376 0.382928 11.00000 -1.50000
H512 2 0.922899 0.626558 0.454786 11.00000 -1.50000
H513 2 0.988388 0.817905 0.492179 11.00000 -1.50000
AFIX 0
N6 3 0.722590 0.807797 0.517608 11.00000 0.02325 0.03395 =
0.02521 0.00505 0.00700 0.00955
C7 1 0.570685 0.801393 0.529225 11.00000 0.02563 0.02893 =
0.02408 0.00944 0.00819 0.01081
C71 1 0.580944 0.919415 0.604855 11.00000 0.02562 0.02747 =
0.02099 0.00762 0.00629 0.00945
C72 1 0.740491 1.031460 0.660741 11.00000 0.02311 0.03204 =
0.02700 0.00441 0.00169 0.00895
AFIX 43
H72 2 0.843074 1.028627 0.650965 11.00000 -1.20000
AFIX 0
C73 1 0.750148 1.146069 0.729952 11.00000 0.03636 0.02665 =
0.02995 0.00262 0.00420 0.00300
AFIX 43
H73 2 0.858905 1.221882 0.766524 11.00000 -1.20000
AFIX 0
C74 1 0.601916 1.150585 0.746049 11.00000 0.05276 0.02267 =
0.02700 0.00397 0.01120 0.01548
AFIX 43
H74 2 0.608836 1.229495 0.793324 11.00000 -1.20000
AFIX 0
C75 1 0.444140 1.039682 0.692946 11.00000 0.04603 0.02743 =
0.03038 0.00391 0.01560 0.01340
AFIX 43
H75 2 0.342569 1.041059 0.704692 11.00000 -1.20000
AFIX 0
C76 1 0.432986 0.926705 0.622832 11.00000 0.03296 0.02690 =
0.03205 0.00687 0.01162 0.01067
AFIX 43
H76 2 0.323325 0.852674 0.586150 11.00000 -1.20000
AFIX 0
C8 1 0.416182 0.688709 0.472900 11.00000 0.02309 0.02929 =
0.02501 0.00653 0.00707 0.00990
AFIX 43
H8 2 0.310806 0.683071 0.482375 11.00000 -1.20000
AFIX 0
C9 1 0.418523 0.584044 0.402221 11.00000 0.01923 0.02526 =
0.01974 0.00453 0.00212 0.00405
C10 1 0.572750 0.592089 0.387948 11.00000 0.02479 0.02740 =
0.02543 0.00452 0.00670 0.00940
HKLF 4
REM PM13 in P-1
REM R1 = 0.0627 for 2089 Fo > 4sig(Fo) and 0.1030 for all 4142 data
REM 284 parameters refined using 0 restraints
END
WGHT 0.1020 0.0000
REM Instructions for potential hydrogen bonds
HTAB C11 O4_$1
HTAB C13 O32_$2
HTAB C14 O12
HTAB C33 O32_$3
HTAB C33 O12_$2
REM Highest difference peak 0.345, deepest hole -0.385, 1-sigma level 0.077
Q1 1 0.5375 0.5772 0.3711 11.00000 0.05 0.35
Q2 1 0.4775 0.6246 0.4276 11.00000 0.05 0.31
Q3 1 0.2545 0.5161 0.2751 11.00000 0.05 0.27
Q4 1 0.7496 0.6743 0.5232 11.00000 0.05 0.27
Q5 1 0.8191 0.5669 0.3652 11.00000 0.05 0.27
Q6 1 0.0353 0.2023 0.2978 11.00000 0.05 0.26
Q7 1 0.3672 0.5381 0.0140 11.00000 0.05 0.25
Q8 1 0.4151 0.1223 0.1446 11.00000 0.05 0.25
Q9 1 0.3745 0.5660 0.3867 11.00000 0.05 0.25
Q10 1 -0.1491 0.5075 0.2050 11.00000 0.05 0.24
Q11 1 0.3732 0.7032 0.3991 11.00000 0.05 0.24
Q12 1 0.3935 0.8405 0.4734 11.00000 0.05 0.24
Q13 1 0.4548 0.2066 -0.1649 11.00000 0.05 0.24
Q14 1 0.5925 0.4640 0.3887 11.00000 0.05 0.23
Q15 1 0.1191 0.4337 0.4396 11.00000 0.05 0.23
Q16 1 0.6574 0.9632 0.6267 11.00000 0.05 0.23
Q17 1 0.4150 0.8874 0.6194 11.00000 0.05 0.22
Q18 1 0.3137 0.1073 0.0109 11.00000 0.05 0.22
Q19 1 -0.0775 0.6155 0.1792 11.00000 0.05 0.22
Q20 1 -0.1795 0.0786 0.1464 11.00000 0.05 0.22
Q21 1 0.1965 0.1171 0.2077 11.00000 0.05 0.22
Q22 1 0.2231 0.5913 0.2741 11.00000 0.05 0.22
Q23 1 0.6041 1.0977 0.7478 11.00000 0.05 0.22
Q24 1 0.2141 0.6292 0.5313 11.00000 0.05 0.21
Q25 1 0.6365 0.5376 0.3522 11.00000 0.05 0.21
Q26 1 0.6982 1.3342 0.8604 11.00000 0.05 0.21
Q27 1 0.9327 0.5179 0.4131 11.00000 0.05 0.21
Q28 1 1.0434 0.6038 0.4305 11.00000 0.05 0.21
Q29 1 0.6941 0.9822 0.7166 11.00000 0.05 0.21
Q30 1 0.2567 0.7365 0.5270 11.00000 0.05 0.21
;
_shelx_res_checksum 25932
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
C C1 0.2620(4) 0.4605(4) 0.3410(2) 0.0254(7) Uani d 1 . .
O O1 0.1154(3) 0.4540(3) 0.35841(16) 0.0280(5) Uani d 1 . .
C C11 -0.0362(4) 0.3256(4) 0.3014(2) 0.0278(7) Uani d 1 . .
H H111 -0.131455 0.312960 0.327715 0.033 Uiso calc 1 . .
H H112 -0.015212 0.221076 0.301129 0.033 Uiso calc 1 . .
C C12 -0.0874(4) 0.3619(4) 0.2024(2) 0.0271(7) Uani d 1 . .
O O12 -0.0317(3) 0.4891(3) 0.17669(17) 0.0319(6) Uani d 1 . .
C C13 -0.2667(5) 0.2383(5) 0.0501(3) 0.0419(10) Uani d 1 . .
H H131 -0.284006 0.343818 0.042431 0.050 Uiso calc 1 . .
H H132 -0.377843 0.148709 0.019592 0.050 Uiso calc 1 . .
O O13 -0.2094(3) 0.2259(3) 0.14844(17) 0.0335(6) Uani d 1 . .
C C14 -0.1360(6) 0.2276(6) 0.0046(3) 0.0553(12) Uani d 1 . .
H H141 -0.025470 0.315251 0.035544 0.083 Uiso calc 1 . .
H H142 -0.174650 0.239485 -0.061125 0.083 Uiso calc 1 . .
H H143 -0.122656 0.121111 0.009848 0.083 Uiso calc 1 . .
N N2 0.2563(3) 0.3601(3) 0.27490(19) 0.0255(6) Uani d 1 . .
N N3 0.4096(3) 0.3724(3) 0.26150(19) 0.0250(6) Uani d 1 . .
C C31 0.3876(5) 0.2649(4) 0.1803(2) 0.0291(7) Uani d 1 . .
H H311 0.294619 0.158906 0.175297 0.035 Uiso calc 1 . .
H H312 0.494912 0.243630 0.186311 0.035 Uiso calc 1 . .
C C32 0.3434(4) 0.3423(4) 0.0937(2) 0.0259(7) Uani d 1 . .
O O32 0.3488(3) 0.4824(3) 0.09355(17) 0.0342(6) Uani d 1 . .
C C33 0.2566(5) 0.2991(4) -0.0702(2) 0.0340(8) Uani d 1 . .
H H331 0.355936 0.394237 -0.072688 0.041 Uiso calc 1 . .
H H332 0.157605 0.334695 -0.076461 0.041 Uiso calc 1 . .
O O33 0.2984(3) 0.2349(3) 0.01799(16) 0.0303(6) Uani d 1 . .
C C34 0.2136(7) 0.1640(6) -0.1464(3) 0.0586(13) Uani d 1 . .
H H341 0.190424 0.204147 -0.206420 0.088 Uiso calc 1 . .
H H342 0.111686 0.072779 -0.145100 0.088 Uiso calc 1 . .
H H343 0.310542 0.126304 -0.137717 0.088 Uiso calc 1 . .
C C4 0.5693(4) 0.4836(4) 0.3110(2) 0.0267(7) Uani d 1 . .
O O4 0.6969(3) 0.4861(3) 0.28866(18) 0.0376(6) Uani d 1 . .
C C5 0.7260(4) 0.7091(4) 0.4497(2) 0.0294(8) Uani d 1 . .
C C51 0.9019(4) 0.7287(5) 0.4444(3) 0.0377(9) Uani d 1 . .
H H511 0.909036 0.754376 0.382928 0.057 Uiso calc 1 . .
H H512 0.922899 0.626558 0.454786 0.057 Uiso calc 1 . .
H H513 0.988388 0.817905 0.492179 0.057 Uiso calc 1 . .
N N6 0.7226(3) 0.8078(3) 0.51761(19) 0.0277(6) Uani d 1 . .
C C7 0.5707(4) 0.8014(4) 0.5292(2) 0.0257(7) Uani d 1 . .
C C71 0.5809(4) 0.9194(4) 0.6049(2) 0.0248(7) Uani d 1 . .
C C72 0.7405(4) 1.0315(4) 0.6607(2) 0.0289(8) Uani d 1 . .
H H72 0.843074 1.028627 0.650965 0.035 Uiso calc 1 . .
C C73 0.7501(5) 1.1461(4) 0.7300(2) 0.0345(8) Uani d 1 . .
H H73 0.858905 1.221882 0.766524 0.041 Uiso calc 1 . .
C C74 0.6019(5) 1.1506(4) 0.7460(2) 0.0338(8) Uani d 1 . .
H H74 0.608836 1.229495 0.793324 0.041 Uiso calc 1 . .
C C75 0.4441(5) 1.0397(4) 0.6929(2) 0.0337(8) Uani d 1 . .
H H75 0.342569 1.041059 0.704692 0.040 Uiso calc 1 . .
C C76 0.4330(5) 0.9267(4) 0.6228(2) 0.0302(8) Uani d 1 . .
H H76 0.323325 0.852674 0.586150 0.036 Uiso calc 1 . .
C C8 0.4162(4) 0.6887(4) 0.4729(2) 0.0257(7) Uani d 1 . .
H H8 0.310806 0.683071 0.482375 0.031 Uiso calc 1 . .
C C9 0.4185(4) 0.5840(4) 0.4022(2) 0.0232(7) Uani d 1 . .
C C10 0.5727(4) 0.5921(4) 0.3879(2) 0.0261(7) Uani d 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
C1 0.0263(17) 0.0302(18) 0.0248(17) 0.0126(14) 0.0118(14) 0.0075(14)
O1 0.0188(11) 0.0366(13) 0.0285(13) 0.0093(10) 0.0085(10) 0.0013(10)
C11 0.0184(16) 0.0282(17) 0.0296(18) 0.0040(13) 0.0024(14) -0.0013(14)
C12 0.0145(15) 0.0309(18) 0.0331(19) 0.0079(13) 0.0044(14) -0.0007(15)
O12 0.0307(13) 0.0221(12) 0.0394(15) 0.0068(10) 0.0083(11) 0.0056(10)
C13 0.035(2) 0.047(2) 0.035(2) 0.0129(18) 0.0019(17) -0.0007(18)
O13 0.0305(13) 0.0299(13) 0.0324(14) 0.0041(10) 0.0071(11) -0.0015(11)
C14 0.052(3) 0.073(3) 0.036(2) 0.020(2) 0.011(2) -0.002(2)
N2 0.0244(14) 0.0324(15) 0.0254(14) 0.0150(12) 0.0104(12) 0.0070(12)
N3 0.0229(14) 0.0295(15) 0.0250(15) 0.0111(11) 0.0091(12) 0.0034(12)
C31 0.0325(18) 0.0296(17) 0.0302(19) 0.0150(14) 0.0125(16) 0.0064(15)
C32 0.0257(17) 0.0241(16) 0.0266(18) 0.0072(13) 0.0084(14) 0.0021(14)
O32 0.0399(15) 0.0307(13) 0.0326(14) 0.0139(11) 0.0104(11) 0.0057(11)
C33 0.039(2) 0.037(2) 0.0289(19) 0.0167(16) 0.0106(16) 0.0064(16)
O33 0.0381(14) 0.0281(12) 0.0272(13) 0.0155(10) 0.0094(11) 0.0022(10)
C34 0.089(4) 0.067(3) 0.030(2) 0.048(3) 0.010(2) 0.007(2)
C4 0.0220(16) 0.0311(17) 0.0247(17) 0.0099(13) 0.0027(14) 0.0058(14)
O4 0.0255(13) 0.0459(15) 0.0457(16) 0.0141(11) 0.0167(12) 0.0000(12)
C5 0.0295(18) 0.0333(18) 0.0277(18) 0.0122(15) 0.0108(15) 0.0102(15)
C51 0.0249(19) 0.049(2) 0.038(2) 0.0105(16) 0.0107(16) 0.0020(18)
N6 0.0233(14) 0.0339(15) 0.0252(15) 0.0096(12) 0.0070(12) 0.0050(12)
C7 0.0256(17) 0.0289(17) 0.0241(17) 0.0108(14) 0.0082(14) 0.0094(14)
C71 0.0256(16) 0.0275(16) 0.0210(16) 0.0095(13) 0.0063(14) 0.0076(13)
C72 0.0231(17) 0.0320(18) 0.0270(18) 0.0089(14) 0.0017(14) 0.0044(15)
C73 0.036(2) 0.0266(18) 0.0299(19) 0.0030(15) 0.0042(16) 0.0026(15)
C74 0.053(2) 0.0227(17) 0.0270(19) 0.0155(16) 0.0112(18) 0.0040(14)
C75 0.046(2) 0.0274(18) 0.0304(19) 0.0134(16) 0.0156(17) 0.0039(15)
C76 0.0330(19) 0.0269(17) 0.0320(19) 0.0107(14) 0.0116(16) 0.0069(15)
C8 0.0231(16) 0.0293(17) 0.0250(17) 0.0099(13) 0.0071(14) 0.0065(14)
C9 0.0192(15) 0.0253(16) 0.0197(16) 0.0040(12) 0.0021(13) 0.0045(13)
C10 0.0248(17) 0.0274(17) 0.0254(17) 0.0094(14) 0.0067(14) 0.0045(14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N2 C1 O1 . . 119.9(3) ?
N2 C1 C9 . . 124.7(3) ?
O1 C1 C9 . . 115.4(3) ?
C1 O1 C11 . . 114.7(2) ?
O1 C11 C12 . . 111.2(3) ?
O1 C11 H111 . . 109.4 ?
C12 C11 H111 . . 109.4 ?
O1 C11 H112 . . 109.4 ?
C12 C11 H112 . . 109.4 ?
H111 C11 H112 . . 108.0 ?
O12 C12 O13 . . 125.3(3) ?
O12 C12 C11 . . 126.0(3) ?
O13 C12 C11 . . 108.6(3) ?
O13 C13 C14 . . 110.4(3) ?
O13 C13 H131 . . 109.6 ?
C14 C13 H131 . . 109.6 ?
O13 C13 H132 . . 109.6 ?
C14 C13 H132 . . 109.6 ?
H131 C13 H132 . . 108.1 ?
C12 O13 C13 . . 115.4(3) ?
C13 C14 H141 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H141 C14 H142 . . 109.5 ?
C13 C14 H143 . . 109.5 ?
H141 C14 H143 . . 109.5 ?
H142 C14 H143 . . 109.5 ?
C1 N2 N3 . . 116.9(3) ?
N2 N3 C4 . . 126.5(3) ?
N2 N3 C31 . . 112.5(3) ?
C4 N3 C31 . . 120.7(3) ?
N3 C31 C32 . . 110.2(3) ?
N3 C31 H311 . . 109.6 ?
C32 C31 H311 . . 109.6 ?
N3 C31 H312 . . 109.6 ?
C32 C31 H312 . . 109.6 ?
H311 C31 H312 . . 108.1 ?
O32 C32 O33 . . 125.0(3) ?
O32 C32 C31 . . 124.6(3) ?
O33 C32 C31 . . 110.4(3) ?
O33 C33 C34 . . 107.2(3) ?
O33 C33 H331 . . 110.3 ?
C34 C33 H331 . . 110.3 ?
O33 C33 H332 . . 110.3 ?
C34 C33 H332 . . 110.3 ?
H331 C33 H332 . . 108.5 ?
C32 O33 C33 . . 114.8(3) ?
C33 C34 H341 . . 109.5 ?
C33 C34 H342 . . 109.5 ?
H341 C34 H342 . . 109.5 ?
C33 C34 H343 . . 109.5 ?
H341 C34 H343 . . 109.5 ?
H342 C34 H343 . . 109.5 ?
O4 C4 N3 . . 119.8(3) ?
O4 C4 C10 . . 124.8(3) ?
N3 C4 C10 . . 115.4(3) ?
N6 C5 C10 . . 121.6(3) ?
N6 C5 C51 . . 115.3(3) ?
C10 C5 C51 . . 123.0(3) ?
C5 C51 H511 . . 109.5 ?
C5 C51 H512 . . 109.5 ?
H511 C51 H512 . . 109.5 ?
C5 C51 H513 . . 109.5 ?
H511 C51 H513 . . 109.5 ?
H512 C51 H513 . . 109.5 ?
C5 N6 C7 . . 120.7(3) ?
N6 C7 C8 . . 121.1(3) ?
N6 C7 C71 . . 116.3(3) ?
C8 C7 C71 . . 122.6(3) ?
C76 C71 C72 . . 117.5(3) ?
C76 C71 C7 . . 121.7(3) ?
C72 C71 C7 . . 120.8(3) ?
C73 C72 C71 . . 120.9(3) ?
C73 C72 H72 . . 119.6 ?
C71 C72 H72 . . 119.6 ?
C74 C73 C72 . . 120.4(3) ?
C74 C73 H73 . . 119.8 ?
C72 C73 H73 . . 119.8 ?
C75 C74 C73 . . 119.6(3) ?
C75 C74 H74 . . 120.2 ?
C73 C74 H74 . . 120.2 ?
C74 C75 C76 . . 120.5(4) ?
C74 C75 H75 . . 119.8 ?
C76 C75 H75 . . 119.8 ?
C75 C76 C71 . . 121.2(3) ?
C75 C76 H76 . . 119.4 ?
C71 C76 H76 . . 119.4 ?
C7 C8 C9 . . 118.6(3) ?
C7 C8 H8 . . 120.7 ?
C9 C8 H8 . . 120.7 ?
C8 C9 C10 . . 120.9(3) ?
C8 C9 C1 . . 122.0(3) ?
C10 C9 C1 . . 117.1(3) ?
C9 C10 C5 . . 117.1(3) ?
C9 C10 C4 . . 119.2(3) ?
C5 C10 C4 . . 123.7(3) ?
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
C1 N2 . 1.285(4) ?
C1 O1 . 1.353(4) ?
C1 C9 . 1.456(4) ?
O1 C11 . 1.432(4) ?
C11 C12 . 1.519(5) ?
C11 H111 . 0.9900 ?
C11 H112 . 0.9900 ?
C12 O12 . 1.185(4) ?
C12 O13 . 1.345(4) ?
C13 O13 . 1.454(4) ?
C13 C14 . 1.506(6) ?
C13 H131 . 0.9900 ?
C13 H132 . 0.9900 ?
C14 H141 . 0.9800 ?
C14 H142 . 0.9800 ?
C14 H143 . 0.9800 ?
N2 N3 . 1.371(4) ?
N3 C4 . 1.378(4) ?
N3 C31 . 1.447(4) ?
C31 C32 . 1.512(5) ?
C31 H311 . 0.9900 ?
C31 H312 . 0.9900 ?
C32 O32 . 1.211(4) ?
C32 O33 . 1.331(4) ?
C33 O33 . 1.468(4) ?
C33 C34 . 1.493(5) ?
C33 H331 . 0.9900 ?
C33 H332 . 0.9900 ?
C34 H341 . 0.9800 ?
C34 H342 . 0.9800 ?
C34 H343 . 0.9800 ?
C4 O4 . 1.238(4) ?
C4 C10 . 1.461(5) ?
C5 N6 . 1.329(4) ?
C5 C10 . 1.422(5) ?
C5 C51 . 1.504(5) ?
C51 H511 . 0.9800 ?
C51 H512 . 0.9800 ?
C51 H513 . 0.9800 ?
N6 C7 . 1.361(4) ?
C7 C8 . 1.385(5) ?
C7 C71 . 1.475(5) ?
C71 C76 . 1.405(5) ?
C71 C72 . 1.406(5) ?
C72 C73 . 1.387(5) ?
C72 H72 . 0.9500 ?
C73 C74 . 1.387(5) ?
C73 H73 . 0.9500 ?
C74 C75 . 1.381(5) ?
C74 H74 . 0.9500 ?
C75 C76 . 1.382(5) ?
C75 H75 . 0.9500 ?
C76 H76 . 0.9500 ?
C8 C9 . 1.390(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.393(4) ?
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
C11 H111 O4 1_455 0.99 2.44 3.053(4) 119.6 yes
C13 H131 O32 2_565 0.99 2.65 3.454(5) 138.1 yes
C14 H141 O12 . 0.98 2.60 3.113(5) 112.9 yes
C33 H331 O32 2_665 0.99 2.54 3.445(5) 151.6 yes
C33 H332 O12 2_565 0.99 2.50 3.278(4) 135.1 yes
C73 H73 O12 2_676 0.95 2.44 3.271(4) 145.4 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
N2 C1 O1 C11 . . . . 2.7(4) ?
C9 C1 O1 C11 . . . . -176.4(3) ?
C1 O1 C11 C12 . . . . -72.1(3) ?
O1 C11 C12 O12 . . . . -12.4(5) ?
O1 C11 C12 O13 . . . . 168.7(3) ?
O12 C12 O13 C13 . . . . 3.9(5) ?
C11 C12 O13 C13 . . . . -177.2(3) ?
C14 C13 O13 C12 . . . . 76.7(4) ?
O1 C1 N2 N3 . . . . -179.5(3) ?
C9 C1 N2 N3 . . . . -0.5(5) ?
C1 N2 N3 C4 . . . . -1.1(5) ?
C1 N2 N3 C31 . . . . -174.5(3) ?
N2 N3 C31 C32 . . . . 81.7(3) ?
C4 N3 C31 C32 . . . . -92.2(4) ?
N3 C31 C32 O32 . . . . 9.4(5) ?
N3 C31 C32 O33 . . . . -170.9(3) ?
O32 C32 O33 C33 . . . . 1.1(5) ?
C31 C32 O33 C33 . . . . -178.6(3) ?
C34 C33 O33 C32 . . . . 178.7(3) ?
N2 N3 C4 O4 . . . . -176.6(3) ?
C31 N3 C4 O4 . . . . -3.7(5) ?
N2 N3 C4 C10 . . . . 3.3(5) ?
C31 N3 C4 C10 . . . . 176.2(3) ?
C10 C5 N6 C7 . . . . -1.0(5) ?
C51 C5 N6 C7 . . . . 179.9(3) ?
C5 N6 C7 C8 . . . . 2.2(5) ?
C5 N6 C7 C71 . . . . -178.2(3) ?
N6 C7 C71 C76 . . . . 179.0(3) ?
C8 C7 C71 C76 . . . . -1.5(5) ?
N6 C7 C71 C72 . . . . 0.2(5) ?
C8 C7 C71 C72 . . . . 179.7(3) ?
C76 C71 C72 C73 . . . . -0.9(5) ?
C7 C71 C72 C73 . . . . 177.9(3) ?
C71 C72 C73 C74 . . . . 0.9(5) ?
C72 C73 C74 C75 . . . . 0.3(5) ?
C73 C74 C75 C76 . . . . -1.3(5) ?
C74 C75 C76 C71 . . . . 1.2(5) ?
C72 C71 C76 C75 . . . . -0.1(5) ?
C7 C71 C76 C75 . . . . -178.9(3) ?
N6 C7 C8 C9 . . . . -1.6(5) ?
C71 C7 C8 C9 . . . . 178.9(3) ?
C7 C8 C9 C10 . . . . -0.1(5) ?
C7 C8 C9 C1 . . . . 179.0(3) ?
N2 C1 C9 C8 . . . . -179.7(3) ?
O1 C1 C9 C8 . . . . -0.6(5) ?
N2 C1 C9 C10 . . . . -0.5(5) ?
O1 C1 C9 C10 . . . . 178.5(3) ?
C8 C9 C10 C5 . . . . 1.2(5) ?
C1 C9 C10 C5 . . . . -178.0(3) ?
C8 C9 C10 C4 . . . . -178.0(3) ?
C1 C9 C10 C4 . . . . 2.8(4) ?
N6 C5 C10 C9 . . . . -0.6(5) ?
C51 C5 C10 C9 . . . . 178.3(3) ?
N6 C5 C10 C4 . . . . 178.5(3) ?
C51 C5 C10 C4 . . . . -2.5(6) ?
O4 C4 C10 C9 . . . . 175.9(3) ?
N3 C4 C10 C9 . . . . -4.1(5) ?
O4 C4 C10 C5 . . . . -3.3(6) ?
N3 C4 C10 C5 . . . . 176.8(3) ?