#------------------------------------------------------------------------------
#$Date: 2023-04-07 04:12:40 +0200 (Fri, 07 Apr 2023) $
#$Revision: 282497 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/27/2022736.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_2022736
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-nitrophenyl)piperazine
;
_journal_issue 5
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi 10.1107/S205698902300302X
_journal_volume 79
_journal_year 2023
_chemical_formula_iupac 'C10 H14 N3 O2 +, C7 H4 I O2 - , 0.5H2 O'
_chemical_formula_moiety '2(C10 H14 N3 O2 +), 2(C7 H4 I O2 -), H2 O'
_chemical_formula_sum 'C34 H38 I2 N6 O9'
_chemical_formula_weight 928.50
_chemical_name_systematic
;
4-(4-Nitrophenyl)piperazin-1-ium 2-iodobenzoate 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 104.967(8)
_cell_angle_beta 94.707(7)
_cell_angle_gamma 107.430(8)
_cell_formula_units_Z 1
_cell_length_a 7.3949(6)
_cell_length_b 9.3440(8)
_cell_length_c 14.4980(10)
_cell_measurement_reflns_used 2991
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 27.97
_cell_measurement_theta_min 2.95
_cell_volume 909.44(14)
_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 0.995
_diffrn_measured_fraction_theta_max 0.887
_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 0.0236
_diffrn_reflns_av_unetI/netI 0.0362
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 6275
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 28.015
_diffrn_reflns_theta_min 2.953
_exptl_absorpt_coefficient_mu 1.791
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.69743
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysalisRed; Oxford Diffraction, 2009)
;
_exptl_crystal_colour orange
_exptl_crystal_density_diffrn 1.695
_exptl_crystal_description prism
_exptl_crystal_F_000 462
_exptl_crystal_size_max 0.500
_exptl_crystal_size_mid 0.440
_exptl_crystal_size_min 0.240
_refine_diff_density_max 0.607
_refine_diff_density_min -0.440
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.021
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 264
_refine_ls_number_reflns 3904
_refine_ls_number_restraints 13
_refine_ls_restrained_S_all 1.019
_refine_ls_R_factor_all 0.0856
_refine_ls_R_factor_gt 0.0464
_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^)+(0.0514P)^2^+0.5457P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0994
_refine_ls_wR_factor_ref 0.1169
_reflns_number_gt 2443
_reflns_number_total 3904
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file hb8051sup1.cif
_cod_data_source_block 3
_cod_original_cell_volume 909.44(13)
_cod_database_code 2022736
_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 0.468
_shelx_estimated_absorpt_t_max 0.673
_shelx_hkl_file
;
0 0 -2 27731.3 136.925 1
0 0 -3 22267.6 152.944 1
0 0 -3 20982.7 103.672 6
0 0 -3 20681.2 97.6238 4
0 0 -4 809.855 37.1980 4
0 0 -4 855.201 25.7982 5
0 0 -4 843.156 59.3593 1
0 0 -4 891.962 40.6050 6
0 0 -5 38337.6 176.904 6
0 0 -5 38547.0 135.534 5
0 0 -5 38902.5 173.653 4
0 0 -5 40937.5 263.893 1
0 0 -6 13188.2 114.867 4
0 0 -6 12635.6 87.8725 5
0 0 -6 13268.5 177.405 1
0 0 -6 13120.6 118.722 6
0 0 -7 194.451 46.3695 4
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0 0 -7 149.947 27.7218 5
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0 0 -8 25783.4 278.996 1
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0 0 -9 14276.0 150.127 4
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8 -6 0 142.974 123.386 0
8 -6 1 4.83176 101.201 5
8 -6 1-32.6127 125.247 0
-8 6 -1 80.8484 124.715 6
8 -6 2-14.6236 122.659 0
-8 6 -2 71.3327 129.364 6
8 -6 3 149.565 129.640 0
-8 6 -3 63.5912 127.764 6
8 -6 4-13.0143 130.215 0
-8 6 -4 160.392 140.341 6
-8 6 -5 94.5700 139.378 6
8 -6 5 147.224 131.379 0
-8 6 -6-37.5999 138.965 6
-8 6 -7 259.254 144.857 6
8 -5 -8 16.3244 96.6143 5
8 -5 -7-108.894 103.783 5
8 -5 -6 72.1040 101.793 5
8 -5 -5-30.4594 98.6366 5
8 -5 -4 67.3056 106.752 5
8 -5 -4 283.090 135.600 0
8 -5 -3 236.828 109.836 5
8 -5 -3 157.917 134.497 0
8 -5 -2 187.535 105.532 5
8 -5 -2 4.64875 136.903 0
8 -5 -1-8.08898 132.677 0
8 -5 -1 146.779 105.413 5
8 -5 0 251.553 96.1971 5
8 -5 0 72.9105 131.077 0
-8 5 0-38.2845 114.485 6
8 -5 1 102.731 125.915 0
-8 5 -1-26.5583 114.289 6
8 -5 2 33.8279 132.633 0
-8 5 -2 229.248 122.798 6
8 -5 3 36.4081 129.662 0
-8 5 -3-131.659 127.350 6
8 -5 4 19.7125 131.669 0
-8 5 -4 352.055 133.022 6
-8 5 -5 31.1026 134.155 6
8 -5 5 466.519 140.561 0
-8 5 -6-115.726 130.129 6
-8 5 -7 14.1791 127.395 6
8 -4 -9 72.0208 94.0148 5
8 -4 -8 148.675 95.5733 5
8 -4 -7 29.1443 93.1183 5
8 -4 -6 50.1601 100.784 5
8 -4 -5 48.6341 100.359 5
8 -4 -4 11.9589 100.419 5
8 -4 -4 52.9785 141.774 0
8 -4 -3-134.720 93.0148 5
8 -4 -3-15.6749 134.146 0
8 -4 -2 193.538 101.323 5
8 -4 -2 171.634 139.926 0
8 -4 -1-97.8498 126.916 0
8 -4 -1 81.8777 94.8235 5
8 -4 0 111.027 91.7897 5
8 -4 0 165.652 127.522 0
8 -4 1 153.206 129.789 0
-8 4 -1-37.8837 114.463 6
8 -4 2-68.6852 130.177 0
-8 4 -2 136.536 118.086 6
8 -4 3 228.560 137.069 0
-8 4 -3 91.8594 117.158 6
8 -4 4 157.884 135.301 0
-8 4 -4-9.02712 126.846 6
8 -4 5 220.305 138.100 0
-8 4 -7 198.284 121.508 6
8 -3 -9 59.6960 93.1951 5
8 -3 -8 211.486 96.4270 5
8 -3 -7 255.831 94.0857 5
8 -3 -6-32.4980 93.6954 5
8 -3 -5 9.60876 89.7025 5
8 -3 -4-71.4551 90.1742 5
8 -3 -4-126.426 131.543 0
8 -3 -3 157.295 88.9276 5
8 -3 -3 60.6117 137.185 0
8 -3 -2 5.13765 86.4867 5
8 -3 -2 65.4674 135.187 0
8 -3 -1-63.5827 128.441 0
8 -3 -1-0.70564 77.3774 5
8 -3 0 287.437 131.672 0
8 -3 1 331.732 131.936 0
8 -3 2 285.012 127.069 0
-8 3 -2 271.211 108.367 6
8 -3 3 212.753 134.621 0
-8 3 -3-167.722 112.773 6
8 -3 4-64.9810 136.357 0
-8 3 -4 232.850 118.187 6
-8 3 -5-16.2659 118.053 6
8 -3 5 191.783 131.821 0
8 -3 6 82.5780 138.421 0
-8 3 -6 17.8560 117.849 6
-8 3 -7 90.7672 127.309 6
8 -2 -10-82.2566 94.0385 5
8 -2 -9-75.4423 94.3300 5
8 -2 -8 121.081 98.5342 5
8 -2 -7 398.264 97.3648 5
8 -2 -6 468.100 105.231 5
8 -2 -5 62.7066 85.6778 5
8 -2 -4 229.351 92.8317 5
8 -2 -4 227.520 138.716 0
8 -2 -3 227.284 89.8161 5
8 -2 -3 290.055 138.801 0
8 -2 -2 47.9547 81.0550 5
8 -2 -2 13.4408 133.479 0
8 -2 -1 67.0802 133.577 0
8 -2 0 317.529 130.958 0
8 -2 1 29.3103 122.563 0
8 -2 2 299.504 107.532 3
8 -2 2 296.171 136.573 0
-8 2 -2 269.414 108.125 6
8 -2 3-46.0843 129.478 0
-8 2 -3 38.4346 107.329 6
8 -2 4 217.320 133.353 0
-8 2 -4 345.115 112.438 6
8 -2 5 204.065 130.258 0
-8 2 -5 70.5365 119.604 6
8 -2 6 162.035 130.032 0
-8 2 -6-184.760 119.260 6
8 -2 7 21.4610 135.101 0
-8 2 -7-206.273 117.041 6
8 -1 -10 54.1109 95.3014 5
8 -1 -9 74.4832 97.3801 5
8 -1 -8 162.279 100.930 5
8 -1 -7 137.220 94.8422 5
8 -1 -6-2.12489 93.4946 5
8 -1 -5 121.729 107.930 5
8 -1 -4 260.589 105.766 3
8 -1 -4 239.703 90.6028 5
8 -1 -4 223.577 137.238 0
8 -1 -3 161.415 102.916 3
8 -1 -3-5.07748 82.4058 5
8 -1 -3-16.6845 134.691 0
8 -1 -2 264.292 99.9454 3
8 -1 -2-57.1458 133.271 0
8 -1 -1-135.780 103.840 3
8 -1 -1 46.8522 126.257 0
8 -1 0-149.353 101.254 3
8 -1 0-121.255 126.498 0
8 -1 1 767.370 137.592 0
8 -1 1 844.082 115.504 3
8 -1 2-36.6351 110.498 3
8 -1 2 93.6141 123.067 0
8 -1 3-6.82185 110.596 3
8 -1 3-71.0841 121.657 0
-8 1 -3 70.0379 106.302 6
8 -1 4 139.395 128.543 0
-8 1 -4 350.102 117.793 6
8 -1 5 67.6498 125.919 0
-8 1 -5 189.813 112.071 6
8 -1 6 245.087 138.037 0
-8 1 -6-155.837 112.549 6
8 0 -8 176.321 112.253 3
8 0 -7 146.103 111.332 3
8 0 -6 153.117 109.820 3
8 0 -5 596.182 116.735 3
8 0 -4-220.354 102.246 3
8 0 -3 513.793 109.623 3
8 0 -3 476.327 133.471 0
8 0 -2 152.718 102.770 3
8 0 -2 29.9812 122.448 0
8 0 -1 13.9334 102.139 3
8 0 -1-38.1378 120.548 0
8 0 0 29.8627 116.944 0
8 0 0 0.22415 104.948 3
8 0 1 258.832 112.826 3
8 0 1 92.5357 117.644 0
8 0 2-121.573 111.908 3
8 0 2 20.0484 105.101 0
8 0 3 295.569 124.172 3
8 0 3 196.727 120.549 0
8 0 4 121.258 124.197 0
-8 0 -4 98.1477 112.044 6
8 0 5 333.556 131.249 0
-8 0 -5 593.127 124.187 6
8 0 6 137.081 132.102 0
8 1 -11 196.453 117.972 3
8 1 -10 167.560 125.260 3
8 1 -9-24.9529 126.732 3
8 1 -8 84.5989 115.607 3
8 1 -7 225.489 117.482 3
8 1 -6 174.067 114.667 3
8 1 -5-28.1109 112.786 3
8 1 -4-13.0727 107.674 3
8 1 -3 81.4498 114.443 3
8 1 -3 242.871 118.293 0
8 1 -2 132.635 108.100 3
8 1 -2-40.7332 107.138 0
8 1 -1 81.3904 116.832 3
8 1 -1-55.4708 116.323 0
8 1 0 11.3424 112.753 3
8 1 0 126.130 108.081 0
8 1 1-144.718 109.944 0
8 1 1 155.846 116.328 3
8 1 2 15.2131 122.639 3
8 1 2 388.457 121.619 0
8 1 3 335.826 125.806 3
8 2 -9 318.919 131.097 3
8 2 -8-134.041 123.670 3
8 2 -7-28.7502 112.449 3
8 2 -6 174.811 126.587 3
8 2 -5 177.781 127.288 3
8 2 -4 251.524 119.143 3
8 2 -3-195.904 121.813 3
8 2 -2 140.674 118.155 0
8 2 -2 278.811 120.291 3
8 2 -1 107.290 112.970 3
8 2 0 84.8200 112.210 3
9 -8 1 174.749 134.086 0
9 -7 -3 84.3200 134.838 0
9 -7 -2-55.9282 136.834 0
9 -7 -1-172.142 107.565 5
9 -7 -1-155.401 142.176 0
9 -7 0-188.528 128.097 0
9 -7 0-147.640 112.363 5
-9 7 -1 477.596 135.261 6
9 -7 1 96.9754 133.974 0
9 -7 2-139.539 135.875 0
-9 7 -2-206.871 130.751 6
9 -6 -3-26.1840 104.701 5
9 -6 -3-249.281 142.840 0
9 -6 -2 45.2026 130.633 0
9 -6 -2-121.339 108.269 5
9 -6 -1-178.081 100.690 5
9 -6 -1-32.2146 141.440 0
9 -6 0-69.8090 133.042 0
9 -6 0-125.418 102.410 5
9 -6 1 57.9957 134.113 0
9 -6 2 152.779 139.781 0
-9 6 -2-14.3491 127.532 6
-9 6 -3 85.2342 127.190 6
-9 6 -4-3.19536 135.592 6
9 -5 -4-119.033 143.028 0
9 -5 -4 62.0946 104.933 5
9 -5 -3-42.1878 99.2076 5
9 -5 -3-181.493 144.181 0
9 -5 -2-37.7094 90.8823 5
9 -5 -2-227.648 136.552 0
9 -5 -1-207.383 95.1392 5
9 -5 -1-36.3825 136.970 0
9 -5 0 73.5996 136.416 0
9 -5 1 3.29648 134.420 0
9 -5 2 48.3309 128.833 0
-9 5 -3-19.6555 123.236 6
-9 5 -4-73.7086 131.400 6
9 -4 -5 30.0254 91.4857 5
9 -4 -4 143.289 88.4054 5
9 -4 -4 26.0603 146.657 0
9 -4 -3-49.4149 84.9502 5
9 -4 -3-125.062 135.316 0
9 -4 -2-69.2175 88.2252 5
9 -4 -2 13.7257 137.167 0
9 -4 -1 289.749 136.330 0
9 -4 0 74.1497 144.549 0
9 -4 1-10.8657 129.018 0
9 -4 2-126.247 132.856 0
-9 4 -3 44.6373 123.051 6
-9 4 -4-194.024 117.323 6
9 -3 -6 10.3254 95.4484 5
9 -3 -5-28.3638 88.4052 5
9 -3 -4 70.2321 150.143 0
9 -3 -4-105.011 90.3801 5
9 -3 -3-15.8499 86.6131 5
9 -3 -3 104.597 139.175 0
9 -3 -2-102.861 141.083 0
9 -3 -1 143.842 136.827 0
9 -3 0 48.9943 130.909 0
9 -3 1 369.428 146.511 0
9 -3 2 129.395 131.954 0
9 -2 -6 128.340 93.2575 5
9 -2 -5 112.926 89.3620 5
9 -2 -4 9.03337 87.8315 5
9 -2 -4 104.634 142.836 0
9 -2 -3-83.1759 142.745 0
9 -2 -2 150.112 147.205 0
9 -2 -1 94.8038 131.835 0
9 -2 0 18.1738 134.089 0
9 -2 1 94.9010 139.283 0
9 -1 -6 123.292 82.9397 5
9 -1 -5 222.002 88.7576 5
9 -1 -4 211.057 81.6884 5
9 -1 -3-25.4744 134.444 0
9 -1 -2 214.549 131.740 0
9 -1 -1-247.270 138.727 0
9 -1 0 164.500 105.903 3
9 -1 0 249.401 122.741 0
9 -1 1-31.2386 106.649 3
9 -1 2 296.934 117.912 3
9 0 -5-20.8497 116.978 3
9 0 -4 63.1415 110.934 3
9 0 -3 164.248 114.696 3
9 0 -2 35.7461 121.374 3
9 0 -1-17.1262 109.813 3
9 0 0 32.8331 125.732 3
;
_shelx_hkl_checksum 86732
_shelx_res_file
;
TITL TK11 IN P-1
shelx.res
created by SHELXL-2018/3 at 14:09:51 on 26-Mar-2023
CELL 0.71073 7.3949 9.344 14.498 104.967 94.707 107.43
ZERR 1 0.0006 0.0008 0.001 0.008 0.007 0.008
LATT 1
SFAC C H I N O
UNIT 34 38 2 6 9
OMIT 0 -1 2
OMIT -1 -9 13
OMIT -1 -9 12
LIST 4
SIZE 0.5 0.44 0.24
L.S. 50
damp 50
acta
conf
bond $h
htab
EQIV $1 x-1, y, z
HTAB C2 I1_$1
EQIV $2 -x-1, -y+1, -z
HTAB C3 O1_$2
EQIV $3 x, y+1, z
HTAB C6 I1_$3
HTAB C7 O1WA
HTAB C7 O1WB
EQIV $4 -x+1, -y+1, -z+1
HTAB N2 O3_$4
HTAB N2 O4
HTAB O1WB O3_$4
simu .01 o1wa o1wb
delu .01 o1wa o1wb
sump .5 .001 1 2 1 3
dfix 0.82 o1wa h1w1 o1wa h1w2
dfix 1.297 h1w1 h1w2
dfix 0.82 o1wb h1w3 o1wb h1w4
dfix 1.297 h1w3 h1w4
WGHT 0.051400 0.545700
FVAR 3.36787 0.22412 0.27558
C1 1 0.137648 0.639331 0.158103 11.00000 0.06134 0.04341 =
0.05663 0.00612 0.02252 0.01449
C2 1 -0.063126 0.573021 0.144026 11.00000 0.06770 0.06241 =
0.07616 0.02716 0.02033 0.01446
AFIX 43
H2 2 -0.116914 0.503974 0.178262 11.00000 -1.20000
AFIX 0
C3 1 -0.182182 0.605884 0.082180 11.00000 0.06517 0.06491 =
0.07877 0.01721 0.01677 0.01226
AFIX 43
H3 2 -0.314731 0.558330 0.073932 11.00000 -1.20000
AFIX 0
C4 1 -0.106445 0.709563 0.031785 11.00000 0.07818 0.05735 =
0.04875 0.00465 0.01522 0.02142
C5 1 0.089666 0.776267 0.042905 11.00000 0.08258 0.07090 =
0.06326 0.02620 0.02627 0.01656
AFIX 43
H5 2 0.141500 0.845343 0.008346 11.00000 -1.20000
AFIX 0
C6 1 0.209252 0.741896 0.104385 11.00000 0.06188 0.06726 =
0.06746 0.02524 0.01821 0.01016
AFIX 43
H6 2 0.341659 0.787923 0.110643 11.00000 -1.20000
AFIX 0
C7 1 0.441810 0.723380 0.266739 11.00000 0.06746 0.08182 =
0.14011 0.06235 0.00503 0.00654
AFIX 23
H7A 2 0.418923 0.802683 0.317971 11.00000 -1.20000
H7B 2 0.499045 0.773784 0.220487 11.00000 -1.20000
AFIX 0
C8 1 0.580143 0.659317 0.309191 11.00000 0.06322 0.12418 =
0.11281 0.07276 0.02425 0.02852
AFIX 23
H8A 2 0.619508 0.592894 0.257190 11.00000 -1.20000
H8B 2 0.693988 0.745578 0.346016 11.00000 -1.20000
AFIX 0
C9 1 0.314474 0.445118 0.320676 11.00000 0.09811 0.08124 =
0.09136 0.04672 0.01306 0.01508
AFIX 23
H9A 2 0.256781 0.389355 0.364560 11.00000 -1.20000
H9B 2 0.340842 0.370385 0.267916 11.00000 -1.20000
AFIX 0
C10 1 0.176599 0.511063 0.281140 11.00000 0.06856 0.09046 =
0.09358 0.05091 0.01766 0.00851
AFIX 23
H10A 2 0.061412 0.425824 0.244767 11.00000 -1.20000
H10B 2 0.139797 0.577245 0.334373 11.00000 -1.20000
AFIX 0
C11 1 0.842355 0.208080 0.380463 11.00000 0.06601 0.05561 =
0.06340 0.01586 0.02351 0.02176
C12 1 0.820558 0.133976 0.282114 11.00000 0.07282 0.04191 =
0.06642 0.00889 0.02818 0.00751
C13 1 0.934366 0.041364 0.249878 11.00000 0.10957 0.05575 =
0.08457 0.00423 0.04845 0.02607
AFIX 43
H13 2 0.920205 -0.009287 0.184112 11.00000 -1.20000
AFIX 0
C14 1 1.066270 0.025369 0.315027 11.00000 0.09677 0.07348 =
0.12539 0.03475 0.05086 0.04429
AFIX 43
H14 2 1.143373 -0.034148 0.292932 11.00000 -1.20000
AFIX 0
C15 1 1.085723 0.095204 0.411233 11.00000 0.08192 0.08619 =
0.10986 0.04644 0.03293 0.03868
AFIX 43
H15 2 1.174200 0.082483 0.455149 11.00000 -1.20000
AFIX 0
C16 1 0.974333 0.184463 0.443225 11.00000 0.08474 0.08892 =
0.07236 0.03090 0.03064 0.04031
AFIX 43
H16 2 0.987579 0.231020 0.509488 11.00000 -1.20000
AFIX 0
C17 1 0.729526 0.314205 0.419450 11.00000 0.07323 0.07876 =
0.06367 -0.00002 0.01183 0.03189
I1 3 0.618643 0.154832 0.181274 11.00000 0.09178 0.07991 =
0.06964 0.01674 0.00710 0.00239
N1 4 0.258868 0.602700 0.218441 11.00000 0.06137 0.05721 =
0.07076 0.02755 0.01977 0.01427
N2 4 0.495444 0.568299 0.372417 11.00000 0.07313 0.08134 =
0.06480 0.02542 0.02565 0.03812
H2A 2 0.482262 0.634787 0.424300 11.00000 -1.20000
H2B 2 0.596118 0.539444 0.396392 11.00000 -1.20000
N3 4 -0.234004 0.747367 -0.031555 11.00000 0.09217 0.08228 =
0.06279 0.01943 0.00246 0.01906
O1 5 -0.406079 0.695927 -0.034185 11.00000 0.09088 0.15911 =
0.13845 0.07477 0.00546 0.03474
O2 5 -0.164134 0.827280 -0.081871 11.00000 0.11634 0.13375 =
0.10017 0.06376 0.00264 0.02227
O3 5 0.613881 0.267317 0.471483 11.00000 0.11871 0.12383 =
0.12975 0.01869 0.07495 0.05769
O4 5 0.764145 0.439530 0.400035 11.00000 0.10645 0.07700 =
0.11590 0.01987 0.01779 0.05071
PART -1
O1WA 5 0.425599 0.975947 0.448867 21.00000 0.20811 0.15513 =
0.16039 0.07010 0.06964 0.11883
H1W1 2 0.395764 1.048066 0.482508 21.00000 -1.50000
H1W2 2 0.469654 1.010860 0.405650 21.00000 -1.50000
part -2
O1WB 5 0.507114 0.934821 0.456879 31.00000 0.21029 0.14479 =
0.16086 0.06924 0.07935 0.12285
H1W3 2 0.426734 0.892414 0.486366 31.00000 -1.50000
H1W4 2 0.604029 0.916302 0.474971 31.00000 -1.50000
PART 0
HKLF 4
REM TK11 IN P-1
REM wR2 = 0.1169, GooF = S = 1.021, Restrained GooF = 1.019 for all data
REM R1 = 0.0464 for 2443 Fo > 4sig(Fo) and 0.0856 for all 3904 data
REM 264 parameters refined using 13 restraints
END
WGHT 0.0514 0.5457
REM Instructions for potential hydrogen bonds
HTAB C2 I1_$1
HTAB C3 O1_$2
HTAB C6 I1_$3
HTAB C7 O1WA
HTAB C7 O1WB
HTAB N2 O3_$4
HTAB N2 O4
HTAB O1WB O3_$4
REM Highest difference peak 0.607, deepest hole -0.440, 1-sigma level 0.070
Q1 1 0.5297 0.1782 0.1403 11.00000 0.05 0.61
Q2 1 0.5377 0.0722 0.2047 11.00000 0.05 0.60
Q3 1 0.6109 0.0418 0.1471 11.00000 0.05 0.53
Q4 1 0.6996 0.2821 0.1825 11.00000 0.05 0.41
Q5 1 0.7338 0.1353 0.2400 11.00000 0.05 0.35
Q6 1 0.1386 0.5219 0.4449 11.00000 0.05 0.27
Q7 1 0.6914 0.2774 0.2556 11.00000 0.05 0.25
Q8 1 0.1616 0.6891 0.1357 11.00000 0.05 0.25
Q9 1 0.8436 0.0792 0.2750 11.00000 0.05 0.25
Q10 1 0.4851 0.8065 0.2614 11.00000 0.05 0.24
Q11 1 0.3311 0.6158 0.2611 11.00000 0.05 0.23
Q12 1 -0.0111 0.7114 0.0599 11.00000 0.05 0.22
Q13 1 -0.1350 0.6949 0.0760 11.00000 0.05 0.22
Q14 1 0.2199 0.5389 0.2151 11.00000 0.05 0.21
Q15 1 -0.4135 0.8161 -0.0762 11.00000 0.05 0.20
Q16 1 0.7774 0.2823 0.5122 11.00000 0.05 0.20
Q17 1 -0.3137 0.7241 -0.1035 11.00000 0.05 0.20
Q18 1 0.9687 0.5747 0.4209 11.00000 0.05 0.20
Q19 1 0.2132 0.6023 0.2787 11.00000 0.05 0.20
Q20 1 0.6646 0.3859 0.4010 11.00000 0.05 0.20
;
_shelx_res_checksum 76167
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 0.1376(6) 0.6393(4) 0.1581(3) 0.0555(10) Uani d 1 . .
C C2 -0.0631(7) 0.5730(5) 0.1440(3) 0.0687(12) Uani d 1 . .
H H2 -0.116914 0.503974 0.178262 0.082 Uiso calc 1 . .
C C3 -0.1822(7) 0.6059(6) 0.0822(4) 0.0724(13) Uani d 1 . .
H H3 -0.314731 0.558330 0.073932 0.087 Uiso calc 1 . .
C C4 -0.1064(7) 0.7096(5) 0.0318(3) 0.0636(11) Uani d 1 . .
C C5 0.0897(7) 0.7763(6) 0.0429(3) 0.0723(13) Uani d 1 . .
H H5 0.141500 0.845343 0.008346 0.087 Uiso calc 1 . .
C C6 0.2093(7) 0.7419(5) 0.1044(3) 0.0667(12) Uani d 1 . .
H H6 0.341659 0.787923 0.110643 0.080 Uiso calc 1 . .
C C7 0.4418(7) 0.7234(7) 0.2667(5) 0.0957(18) Uani d 1 . .
H H7A 0.418923 0.802683 0.317971 0.115 Uiso calc 1 . .
H H7B 0.499045 0.773784 0.220487 0.115 Uiso calc 1 . .
C C8 0.5801(7) 0.6593(7) 0.3092(4) 0.0927(17) Uani d 1 . .
H H8A 0.619508 0.592894 0.257190 0.111 Uiso calc 1 . .
H H8B 0.693988 0.745578 0.346016 0.111 Uiso calc 1 . .
C C9 0.3145(8) 0.4451(6) 0.3207(4) 0.0897(16) Uani d 1 . .
H H9A 0.256781 0.389355 0.364560 0.108 Uiso calc 1 . .
H H9B 0.340842 0.370385 0.267916 0.108 Uiso calc 1 . .
C C10 0.1766(7) 0.5111(6) 0.2811(4) 0.0835(15) Uani d 1 . .
H H10A 0.061412 0.425824 0.244767 0.100 Uiso calc 1 . .
H H10B 0.139797 0.577245 0.334373 0.100 Uiso calc 1 . .
C C11 0.8424(6) 0.2081(5) 0.3805(3) 0.0609(11) Uani d 1 . .
C C12 0.8206(6) 0.1340(5) 0.2821(3) 0.0635(12) Uani d 1 . .
C C13 0.9344(9) 0.0414(6) 0.2499(4) 0.0850(16) Uani d 1 . .
H H13 0.920205 -0.009287 0.184112 0.102 Uiso calc 1 . .
C C14 1.0663(9) 0.0254(7) 0.3150(5) 0.0919(17) Uani d 1 . .
H H14 1.143373 -0.034148 0.292932 0.110 Uiso calc 1 . .
C C15 1.0857(8) 0.0952(7) 0.4112(5) 0.0857(15) Uani d 1 . .
H H15 1.174200 0.082483 0.455149 0.103 Uiso calc 1 . .
C C16 0.9743(7) 0.1845(6) 0.4432(4) 0.0769(13) Uani d 1 . .
H H16 0.987579 0.231020 0.509488 0.092 Uiso calc 1 . .
C C17 0.7295(7) 0.3142(7) 0.4194(3) 0.0746(13) Uani d 1 . .
I I1 0.61864(5) 0.15483(4) 0.18127(2) 0.08807(17) Uani d 1 . .
N N1 0.2589(5) 0.6027(4) 0.2184(3) 0.0622(9) Uani d 1 . .
N N2 0.4954(6) 0.5683(5) 0.3724(3) 0.0686(10) Uani d 1 . .
H H2A 0.482(7) 0.635(6) 0.424(4) 0.082 Uiso d 1 . .
H H2B 0.596(7) 0.539(6) 0.396(4) 0.082 Uiso d 1 . .
N N3 -0.2340(7) 0.7474(5) -0.0316(3) 0.0825(12) Uani d 1 . .
O O1 -0.4061(7) 0.6959(6) -0.0342(4) 0.1259(16) Uani d 1 . .
O O2 -0.1641(7) 0.8273(6) -0.0819(3) 0.1165(14) Uani d 1 . .
O O3 0.6139(6) 0.2673(6) 0.4715(3) 0.1206(15) Uani d 1 . .
O O4 0.7641(6) 0.4395(5) 0.4000(3) 0.0969(11) Uani d 1 . .
O O1WA 0.426(5) 0.976(3) 0.449(2) 0.154(7) Uani d 0.224(3) A -1
H H1W1 0.396(13) 1.048(8) 0.483(6) 0.231 Uiso d 0.224(3) A -1
H H1W2 0.470(14) 1.011(10) 0.406(4) 0.231 Uiso d 0.224(3) A -1
O O1WB 0.507(4) 0.935(3) 0.4569(19) 0.149(6) Uani d 0.276(3) B -2
H H1W3 0.427(8) 0.892(15) 0.486(6) 0.224 Uiso d 0.276(3) B -2
H H1W4 0.604(7) 0.916(12) 0.475(10) 0.224 Uiso d 0.276(3) B -2
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 0.061(2) 0.043(2) 0.057(2) 0.0145(19) 0.023(2) 0.0061(18)
C2 0.068(3) 0.062(3) 0.076(3) 0.014(2) 0.020(2) 0.027(2)
C3 0.065(3) 0.065(3) 0.079(3) 0.012(2) 0.017(2) 0.017(2)
C4 0.078(3) 0.057(3) 0.049(2) 0.021(2) 0.015(2) 0.0047(19)
C5 0.083(3) 0.071(3) 0.063(3) 0.017(2) 0.026(2) 0.026(2)
C6 0.062(3) 0.067(3) 0.067(3) 0.010(2) 0.018(2) 0.025(2)
C7 0.067(3) 0.082(3) 0.140(5) 0.007(3) 0.005(3) 0.062(3)
C8 0.063(3) 0.124(4) 0.113(4) 0.029(3) 0.024(3) 0.073(4)
C9 0.098(4) 0.081(3) 0.091(4) 0.015(3) 0.013(3) 0.047(3)
C10 0.069(3) 0.090(4) 0.094(3) 0.009(3) 0.018(3) 0.051(3)
C11 0.066(3) 0.056(2) 0.063(2) 0.022(2) 0.024(2) 0.016(2)
C12 0.073(3) 0.042(2) 0.066(3) 0.008(2) 0.028(2) 0.0089(19)
C13 0.110(4) 0.056(3) 0.085(3) 0.026(3) 0.048(3) 0.004(2)
C14 0.097(4) 0.073(3) 0.125(5) 0.044(3) 0.051(4) 0.035(3)
C15 0.082(3) 0.086(4) 0.110(4) 0.039(3) 0.033(3) 0.046(3)
C16 0.085(3) 0.089(3) 0.072(3) 0.040(3) 0.031(3) 0.031(3)
C17 0.073(3) 0.079(3) 0.064(3) 0.032(3) 0.012(2) 0.000(2)
I1 0.0918(3) 0.0799(2) 0.0696(2) 0.00239(18) 0.00710(17) 0.01674(16)
N1 0.061(2) 0.057(2) 0.071(2) 0.0143(17) 0.0198(18) 0.0276(17)
N2 0.073(2) 0.081(3) 0.065(2) 0.038(2) 0.0256(19) 0.025(2)
N3 0.092(3) 0.082(3) 0.063(2) 0.019(2) 0.002(2) 0.019(2)
O1 0.091(3) 0.159(4) 0.138(4) 0.035(3) 0.005(3) 0.075(3)
O2 0.116(3) 0.134(4) 0.100(3) 0.022(3) 0.003(2) 0.064(3)
O3 0.119(3) 0.124(3) 0.130(3) 0.058(3) 0.075(3) 0.019(3)
O4 0.106(3) 0.077(2) 0.116(3) 0.051(2) 0.018(2) 0.020(2)
O1WA 0.208(17) 0.155(15) 0.160(13) 0.119(12) 0.070(15) 0.070(12)
O1WB 0.210(16) 0.145(13) 0.161(12) 0.123(11) 0.079(14) 0.069(11)
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'
I I -0.4742 1.8119 '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
N1 C1 C6 . . 121.4(4) ?
N1 C1 C2 . . 122.6(4) ?
C6 C1 C2 . . 115.9(4) ?
C3 C2 C1 . . 122.4(4) ?
C3 C2 H2 . . 118.8 ?
C1 C2 H2 . . 118.8 ?
C2 C3 C4 . . 120.0(4) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C5 C4 C3 . . 119.5(5) ?
C5 C4 N3 . . 120.9(4) ?
C3 C4 N3 . . 119.6(4) ?
C6 C5 C4 . . 120.5(4) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C1 . . 121.7(4) ?
C5 C6 H6 . . 119.2 ?
C1 C6 H6 . . 119.2 ?
N1 C7 C8 . . 112.7(4) ?
N1 C7 H7A . . 109.1 ?
C8 C7 H7A . . 109.1 ?
N1 C7 H7B . . 109.1 ?
C8 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
N2 C8 C7 . . 111.8(4) ?
N2 C8 H8A . . 109.3 ?
C7 C8 H8A . . 109.3 ?
N2 C8 H8B . . 109.3 ?
C7 C8 H8B . . 109.3 ?
H8A C8 H8B . . 107.9 ?
N2 C9 C10 . . 111.7(4) ?
N2 C9 H9A . . 109.3 ?
C10 C9 H9A . . 109.3 ?
N2 C9 H9B . . 109.3 ?
C10 C9 H9B . . 109.3 ?
H9A C9 H9B . . 107.9 ?
N1 C10 C9 . . 111.8(4) ?
N1 C10 H10A . . 109.3 ?
C9 C10 H10A . . 109.3 ?
N1 C10 H10B . . 109.3 ?
C9 C10 H10B . . 109.3 ?
H10A C10 H10B . . 107.9 ?
C16 C11 C12 . . 118.0(4) ?
C16 C11 C17 . . 120.1(4) ?
C12 C11 C17 . . 121.9(4) ?
C11 C12 C13 . . 119.3(5) ?
C11 C12 I1 . . 121.3(3) ?
C13 C12 I1 . . 119.4(4) ?
C14 C13 C12 . . 120.1(5) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C15 C14 C13 . . 120.8(5) ?
C15 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
C14 C15 C16 . . 119.4(6) ?
C14 C15 H15 . . 120.3 ?
C16 C15 H15 . . 120.3 ?
C15 C16 C11 . . 122.3(5) ?
C15 C16 H16 . . 118.9 ?
C11 C16 H16 . . 118.9 ?
O4 C17 O3 . . 126.3(5) ?
O4 C17 C11 . . 118.0(5) ?
O3 C17 C11 . . 115.6(5) ?
C1 N1 C10 . . 118.7(4) ?
C1 N1 C7 . . 117.8(3) ?
C10 N1 C7 . . 111.5(4) ?
C8 N2 C9 . . 110.3(4) ?
C8 N2 H2A . . 107(3) ?
C9 N2 H2A . . 114(3) ?
C8 N2 H2B . . 104(3) ?
C9 N2 H2B . . 119(3) ?
H2A N2 H2B . . 102(5) ?
O1 N3 O2 . . 122.4(5) ?
O1 N3 C4 . . 119.3(5) ?
O2 N3 C4 . . 118.3(5) ?
H1W1 O1WA H1W2 . . 103(3) ?
H1W3 O1WB H1W4 . . 103(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 N1 . 1.377(5) ?
C1 C6 . 1.398(6) ?
C1 C2 . 1.401(6) ?
C2 C3 . 1.359(7) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.376(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(6) ?
C4 N3 . 1.443(7) ?
C5 C6 . 1.367(7) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.454(6) ?
C7 C8 . 1.496(7) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 N2 . 1.461(6) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N2 . 1.465(7) ?
C9 C10 . 1.487(7) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 N1 . 1.453(5) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C16 . 1.384(7) ?
C11 C12 . 1.387(6) ?
C11 C17 . 1.511(7) ?
C12 C13 . 1.403(7) ?
C12 I1 . 2.090(5) ?
C13 C14 . 1.369(8) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.354(8) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.365(7) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 O4 . 1.232(6) ?
C17 O3 . 1.243(6) ?
N2 H2A . 0.88(5) ?
N2 H2B . 0.93(5) ?
N3 O1 . 1.212(6) ?
N3 O2 . 1.212(6) ?
O1WA H1W1 . 0.82(2) ?
O1WA H1W2 . 0.82(2) ?
O1WB H1W3 . 0.83(2) ?
O1WB H1W4 . 0.82(2) ?
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
C2 H2 I1 1_455 0.93 3.28 4.110(4) 150.2 yes
C3 H3 O1 2_465 0.93 2.53 3.347(7) 146.9 yes
C6 H6 I1 1_565 0.93 3.26 3.940(4) 131.6 yes
C7 H7A O1WA . 0.97 2.14 3.09(3) 167.0 yes
C7 H7A O1WB . 0.97 2.01 2.85(3) 144.5 yes
N2 H2A O3 2_666 0.88(5) 1.86(5) 2.717(5) 164(5) yes
N2 H2B O4 . 0.93(5) 1.77(5) 2.666(6) 160(5) yes
O1WB H1W3 O3 2_666 0.83(2) 1.71(10) 2.37(2) 135(12) 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
N1 C1 C2 C3 . . . . -178.0(4) ?
C6 C1 C2 C3 . . . . -0.1(6) ?
C1 C2 C3 C4 . . . . -1.0(7) ?
C2 C3 C4 C5 . . . . 1.5(7) ?
C2 C3 C4 N3 . . . . -178.2(4) ?
C3 C4 C5 C6 . . . . -0.8(7) ?
N3 C4 C5 C6 . . . . 178.8(4) ?
C4 C5 C6 C1 . . . . -0.3(7) ?
N1 C1 C6 C5 . . . . 178.7(4) ?
C2 C1 C6 C5 . . . . 0.8(6) ?
N1 C7 C8 N2 . . . . -53.1(7) ?
N2 C9 C10 N1 . . . . 56.1(6) ?
C16 C11 C12 C13 . . . . -1.3(6) ?
C17 C11 C12 C13 . . . . 177.7(4) ?
C16 C11 C12 I1 . . . . 177.8(3) ?
C17 C11 C12 I1 . . . . -3.3(6) ?
C11 C12 C13 C14 . . . . -0.4(7) ?
I1 C12 C13 C14 . . . . -179.5(4) ?
C12 C13 C14 C15 . . . . 1.6(8) ?
C13 C14 C15 C16 . . . . -1.0(8) ?
C14 C15 C16 C11 . . . . -0.7(8) ?
C12 C11 C16 C15 . . . . 1.9(7) ?
C17 C11 C16 C15 . . . . -177.1(5) ?
C16 C11 C17 O4 . . . . 111.4(5) ?
C12 C11 C17 O4 . . . . -67.5(6) ?
C16 C11 C17 O3 . . . . -66.2(6) ?
C12 C11 C17 O3 . . . . 114.9(5) ?
C6 C1 N1 C10 . . . . 172.5(4) ?
C2 C1 N1 C10 . . . . -9.7(6) ?
C6 C1 N1 C7 . . . . 32.9(6) ?
C2 C1 N1 C7 . . . . -149.3(5) ?
C9 C10 N1 C1 . . . . 164.4(4) ?
C9 C10 N1 C7 . . . . -53.6(6) ?
C8 C7 N1 C1 . . . . -165.4(4) ?
C8 C7 N1 C10 . . . . 52.3(7) ?
C7 C8 N2 C9 . . . . 54.3(7) ?
C10 C9 N2 C8 . . . . -56.0(6) ?
C5 C4 N3 O1 . . . . -174.4(5) ?
C3 C4 N3 O1 . . . . 5.2(7) ?
C5 C4 N3 O2 . . . . 7.1(7) ?
C3 C4 N3 O2 . . . . -173.3(5) ?
_cod_database_fobs_code 2022736