#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:42:46 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298867 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/99/7249959.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249959
loop_
_publ_author_name
'Havl°ujová, Tereza'
'Hriňová, Erika'
'Zmeškalová, Eliška'
'Kučeráková, Monika'
'Ridvan, Luděk'
'Šoóš, Miroslav'
_publ_section_title
;
 Pharmaceutical salts of venetoclax with dicarboxylic and sulfonic acids:
 solid-state characterization and dissolution performance
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              1816
_journal_page_last               1829
_journal_paper_doi               10.1039/D4CE01121J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C59 H66 Cl1 N7 O13 S3'
_chemical_formula_sum            'C59 H66 Cl N7 O13 S3'
_chemical_formula_weight         1212.86
_chemical_name_systematic        Venetoclax
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_update_record
;
2024-10-25 deposited with the CCDC.	2025-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                109.4801(9)
_cell_angle_beta                 95.9264(8)
_cell_angle_gamma                109.2612(9)
_cell_formula_units_Z            2
_cell_length_a                   12.19350(10)
_cell_length_b                   15.73850(10)
_cell_length_c                   17.4811(2)
_cell_measurement_reflns_used    58145
_cell_measurement_temperature    95
_cell_measurement_theta_max      73
_cell_measurement_theta_min      3
_cell_volume                     2898.70(5)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      95
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            100705
_diffrn_reflns_theta_full        69.792
_diffrn_reflns_theta_max         73.465
_diffrn_reflns_theta_min         2.762
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.184
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1276
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.71
_refine_diff_density_min         -0.75
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     768
_refine_ls_number_reflns         11458
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.0006019
_refine_ls_shift/su_mean         0.0000321
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.00P)² +18.96P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1379
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1374
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              18
_reflns_limit_k_min              -19
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                10350
_reflns_number_total             11510
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   1.45
_oxford_diffrn_Wilson_scale      0.05
_oxford_refine_ls_r_factor_ref   0.0510
_oxford_refine_ls_scale          4.13(4)
_oxford_reflns_number_all        11466
_cod_data_source_file            d4ce01121j2.cif
_cod_data_source_block           I_CCDC4
_cod_depositor_comments
'Adding full bibliography for 7249955--7249959.cif.'
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C59 H66 Cl1 N7 O13 S3'
_cod_database_code               7249959
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 1.35801(8) 0.92899(7) 0.79687(6) 0.0330 1.0000 Uani . . . . . .
C2 C 1.2315(3) 0.8538(2) 0.7145(2) 0.0237 1.0000 Uani . . . . . .
C3 C 1.1253(3) 0.8657(3) 0.7183(2) 0.0252 1.0000 Uani . . . . . .
C4 C 1.0247(3) 0.8044(3) 0.6530(2) 0.0239 1.0000 Uani . . . . . .
C5 C 1.0309(3) 0.7320(2) 0.5840(2) 0.0201 1.0000 Uani . . . . . .
C6 C 1.1415(3) 0.7242(3) 0.5810(2) 0.0317 1.0000 Uani . . . . . .
C7 C 1.2419(3) 0.7838(3) 0.6463(2) 0.0339 1.0000 Uani . . . . . .
C8 C 0.9256(3) 0.6681(2) 0.5113(2) 0.0205 1.0000 Uani . . . . . .
C9 C 0.8344(3) 0.5909(2) 0.5096(2) 0.0194 1.0000 Uani . . . . . .
C10 C 0.8379(3) 0.5533(2) 0.57802(19) 0.0183 1.0000 Uani D . . . . .
N11 N 0.7286(2) 0.53902(19) 0.61322(16) 0.0163 1.0000 Uani D . . . . .
C12 C 0.7065(3) 0.6313(2) 0.64753(19) 0.0166 1.0000 Uani D . . . . .
C13 C 0.5977(3) 0.6135(2) 0.68402(19) 0.0165 1.0000 Uani . . . . . .
N14 N 0.6104(2) 0.57406(19) 0.74788(16) 0.0154 1.0000 Uani . . . . . .
C15 C 0.5478(3) 0.5856(2) 0.80926(19) 0.0158 1.0000 Uani . . . . . .
C16 C 0.5333(3) 0.6748(2) 0.84702(19) 0.0162 1.0000 Uani . . . . . .
C17 C 0.4866(3) 0.6910(2) 0.91681(19) 0.0143 1.0000 Uani . . . . . .
O18 O 0.49351(18) 0.78619(15) 0.95845(13) 0.0159 1.0000 Uani . . . . . .
C19 C 0.3909(3) 0.8047(2) 0.95067(19) 0.0147 1.0000 Uani . . . . . .
C20 C 0.2855(3) 0.7428(2) 0.89044(19) 0.0166 1.0000 Uani . . . . . .
C21 C 0.1908(3) 0.7726(2) 0.8890(2) 0.0169 1.0000 Uani . . . . . .
C22 C 0.2059(3) 0.8642(2) 0.9503(2) 0.0176 1.0000 Uani D . . . . .
N23 N 0.1038(2) 0.8799(2) 0.93968(18) 0.0199 1.0000 Uani D . . . . .
C24 C 0.0223(3) 0.8000(2) 0.8719(2) 0.0220 1.0000 Uani D . . . . .
C25 C 0.0716(3) 0.7338(2) 0.8395(2) 0.0207 1.0000 Uani . . . . . .
N26 N 0.3086(2) 0.92278(19) 1.00765(17) 0.0167 1.0000 Uani D . . . . .
C27 C 0.4015(3) 0.8938(2) 1.0086(2) 0.0180 1.0000 Uani D . . . . .
C28 C 0.4468(3) 0.6203(2) 0.95038(19) 0.0146 1.0000 Uani . . . . . .
C29 C 0.4035(3) 0.6314(2) 1.02777(19) 0.0150 1.0000 Uani D . . . . .
O30 O 0.33500(19) 0.56250(16) 1.03875(14) 0.0180 1.0000 Uani . . . . . .
N31 N 0.4483(2) 0.72490(19) 1.08944(16) 0.0170 1.0000 Uani D . . . . .
S32 S 0.40707(6) 0.75095(5) 1.17941(5) 0.0153 1.0000 Uani D . . . . .
O33 O 0.4299(2) 0.69292(17) 1.22195(14) 0.0208 1.0000 Uani . . . . . .
O34 O 0.4638(2) 0.85520(17) 1.21878(14) 0.0212 1.0000 Uani . . . . . .
C35 C 0.2527(3) 0.7132(2) 1.14567(19) 0.0161 1.0000 Uani . . . . . .
C36 C 0.1766(3) 0.6283(2) 1.14794(19) 0.0163 1.0000 Uani . . . . . .
C37 C 0.0547(3) 0.5932(2) 1.11274(19) 0.0160 1.0000 Uani . . . . . .
N38 N -0.0189(2) 0.5052(2) 1.12066(17) 0.0194 1.0000 Uani . . . . . .
O39 O -0.1278(2) 0.46850(18) 1.08896(16) 0.0260 1.0000 Uani . . . . . .
O40 O 0.0290(2) 0.46897(19) 1.15933(17) 0.0300 1.0000 Uani . . . . . .
C41 C 0.0060(3) 0.6411(2) 1.0706(2) 0.0168 1.0000 Uani D . . . . .
N42 N -0.1095(2) 0.6078(2) 1.03171(17) 0.0183 1.0000 Uani D . . . . .
C43 C -0.1580(3) 0.6609(2) 0.9932(2) 0.0187 1.0000 Uani D . . . . .
C44 C -0.1656(3) 0.7519(2) 1.05839(19) 0.0166 1.0000 Uani . . . . . .
C45 C -0.2054(3) 0.8100(2) 1.0150(2) 0.0194 1.0000 Uani . . . . . .
C46 C -0.2307(3) 0.8917(2) 1.0760(2) 0.0211 1.0000 Uani . . . . . .
O47 O -0.3119(2) 0.85759(17) 1.12320(15) 0.0217 1.0000 Uani . . . . . .
C48 C -0.2649(3) 0.8132(3) 1.1704(2) 0.0238 1.0000 Uani . . . . . .
C49 C -0.2502(3) 0.7240(3) 1.1123(2) 0.0216 1.0000 Uani . . . . . .
C50 C 0.0897(3) 0.7299(2) 1.0715(2) 0.0185 1.0000 Uani . . . . . .
C51 C 0.2082(3) 0.7655(2) 1.1085(2) 0.0175 1.0000 Uani . . . . . .
C52 C 0.4529(3) 0.5302(2) 0.9083(2) 0.0171 1.0000 Uani . . . . . .
C53 C 0.5026(3) 0.5125(2) 0.84032(19) 0.0168 1.0000 Uani . . . . . .
C54 C 0.6317(3) 0.4840(2) 0.7160(2) 0.0189 1.0000 Uani . . . . . .
C55 C 0.7416(3) 0.5012(2) 0.68015(19) 0.0178 1.0000 Uani D . . . . .
C56 C 0.7289(3) 0.5291(3) 0.4355(2) 0.0266 1.0000 Uani . . . . . .
C57 C 0.7272(3) 0.5722(3) 0.3693(2) 0.0319 1.0000 Uani . . . . . .
C58 C 0.8512(3) 0.6139(3) 0.3538(2) 0.0292 1.0000 Uani . . . . . .
C59 C 0.9324(3) 0.6958(3) 0.4361(2) 0.0252 1.0000 Uani . . . . . .
C60 C 0.8428(4) 0.6555(4) 0.2869(3) 0.0458 1.0000 Uani . . . . . .
C61 C 0.9026(4) 0.5353(3) 0.3248(2) 0.0403 1.0000 Uani . . . . . .
S62 S 0.53186(7) 0.30218(6) 0.47394(5) 0.0176 1.0000 Uani . . . . . .
O63 O 0.5153(2) 0.39522(16) 0.50577(14) 0.0209 1.0000 Uani . . . . . .
O64 O 0.5050(2) 0.25958(17) 0.38382(14) 0.0219 1.0000 Uani . . . . . .
O65 O 0.6485(2) 0.31341(18) 0.51562(15) 0.0238 1.0000 Uani . . . . . .
C66 C 0.4223(3) 0.2211(2) 0.5042(2) 0.0202 1.0000 Uani . . . . . .
C67 C 0.3035(3) 0.1787(2) 0.4591(2) 0.0232 1.0000 Uani . . . . . .
C68 C 0.2175(3) 0.1177(3) 0.4840(2) 0.0285 1.0000 Uani . . . . . .
C69 C 0.2481(4) 0.0962(3) 0.5523(2) 0.0334 1.0000 Uani . . . . . .
C70 C 0.3667(4) 0.1386(3) 0.5960(2) 0.0364 1.0000 Uani . . . . . .
C71 C 0.4538(3) 0.2013(3) 0.5726(2) 0.0283 1.0000 Uani . . . . . .
C72 C 0.1537(4) 0.0282(4) 0.5784(3) 0.0489 1.0000 Uani . . . . . .
S73 S 0.79609(7) 0.92161(6) 0.84698(5) 0.0205 1.0000 Uani . . . . . .
O74 O 0.7898(2) 0.82556(18) 0.79653(16) 0.0275 1.0000 Uani . . . . . .
O75 O 0.6919(2) 0.91570(17) 0.88405(15) 0.0232 1.0000 Uani . . . . . .
O76 O 0.9090(2) 0.98236(18) 0.91012(15) 0.0274 1.0000 Uani . . . . . .
C77 C 0.7858(3) 0.9826(2) 0.7795(2) 0.0207 1.0000 Uani . . . . . .
C78 C 0.6740(3) 0.9709(3) 0.7393(2) 0.0251 1.0000 Uani . . . . . .
C79 C 0.6673(4) 1.0196(3) 0.6871(2) 0.0303 1.0000 Uani . . . . . .
C80 C 0.7699(4) 1.0797(3) 0.6739(2) 0.0338 1.0000 Uani . . . . . .
C81 C 0.7597(5) 1.1345(4) 0.6189(3) 0.0537 1.0000 Uani . . . . . .
C82 C 0.8803(4) 1.0891(3) 0.7138(3) 0.0362 1.0000 Uani . . . . . .
C83 C 0.8893(3) 1.0407(3) 0.7657(2) 0.0291 1.0000 Uani . . . . . .
H31 H 1.1208 0.9147 0.7648 0.0311 1.0000 Uiso R . . . . .
H41 H 0.9508 0.8114 0.6547 0.0304 1.0000 Uiso R . . . . .
H61 H 1.1469 0.6765 0.5329 0.0394 1.0000 Uiso R . . . . .
H71 H 1.3158 0.7768 0.6443 0.0415 1.0000 Uiso R . . . . .
H101 H 0.9076 0.5997 0.6244 0.0237 1.0000 Uiso R . . . . .
H102 H 0.8440 0.4893 0.5559 0.0238 1.0000 Uiso R . . . . .
H122 H 0.7775 0.6817 0.6910 0.0210 1.0000 Uiso R . . . . .
H121 H 0.6928 0.6525 0.6020 0.0211 1.0000 Uiso R . . . . .
H132 H 0.5900 0.6757 0.7090 0.0219 1.0000 Uiso R . . . . .
H131 H 0.5265 0.5676 0.6394 0.0219 1.0000 Uiso R . . . . .
H161 H 0.5574 0.7239 0.8264 0.0206 1.0000 Uiso R . . . . .
H201 H 0.2790 0.6825 0.8515 0.0212 1.0000 Uiso R . . . . .
H241 H -0.0555 0.7942 0.8516 0.0270 1.0000 Uiso R . . . . .
H251 H 0.0347 0.6742 0.7931 0.0261 1.0000 Uiso R . . . . .
H271 H 0.4731 0.9351 1.0494 0.0230 1.0000 Uiso R . . . . .
H361 H 0.2067 0.5927 1.1723 0.0208 1.0000 Uiso R . . . . .
H432 H -0.2393 0.6169 0.9606 0.0239 1.0000 Uiso R . . . . .
H431 H -0.1100 0.6805 0.9556 0.0241 1.0000 Uiso R . . . . .
H441 H -0.0839 0.7941 1.0948 0.0220 1.0000 Uiso R . . . . .
H451 H -0.2784 0.7661 0.9710 0.0240 1.0000 Uiso R . . . . .
H452 H -0.1428 0.8388 0.9899 0.0239 1.0000 Uiso R . . . . .
H461 H -0.1551 0.9420 1.1148 0.0270 1.0000 Uiso R . . . . .
H462 H -0.2676 0.9205 1.0443 0.0271 1.0000 Uiso R . . . . .
H481 H -0.3220 0.7939 1.2030 0.0290 1.0000 Uiso R . . . . .
H482 H -0.1872 0.8603 1.2074 0.0291 1.0000 Uiso R . . . . .
H491 H -0.2192 0.6937 1.1447 0.0272 1.0000 Uiso R . . . . .
H492 H -0.3287 0.6773 1.0753 0.0269 1.0000 Uiso R . . . . .
H501 H 0.0619 0.7651 1.0455 0.0231 1.0000 Uiso R . . . . .
H511 H 0.2610 0.8259 1.1094 0.0218 1.0000 Uiso R . . . . .
H521 H 0.4226 0.4796 0.9280 0.0210 1.0000 Uiso R . . . . .
H531 H 0.5060 0.4510 0.8148 0.0211 1.0000 Uiso R . . . . .
H541 H 0.6467 0.4637 0.7617 0.0231 1.0000 Uiso R . . . . .
H542 H 0.5614 0.4323 0.6729 0.0227 1.0000 Uiso R . . . . .
H552 H 0.8119 0.5502 0.7243 0.0230 1.0000 Uiso R . . . . .
H551 H 0.7522 0.4392 0.6552 0.0230 1.0000 Uiso R . . . . .
H562 H 0.6553 0.5213 0.4548 0.0331 1.0000 Uiso R . . . . .
H561 H 0.7319 0.4647 0.4100 0.0331 1.0000 Uiso R . . . . .
H572 H 0.6981 0.6252 0.3885 0.0393 1.0000 Uiso R . . . . .
H571 H 0.6729 0.5210 0.3172 0.0392 1.0000 Uiso R . . . . .
H592 H 1.0155 0.7142 0.4308 0.0323 1.0000 Uiso R . . . . .
H591 H 0.9101 0.7526 0.4470 0.0324 1.0000 Uiso R . . . . .
H603 H 0.9226 0.6860 0.2802 0.0698 1.0000 Uiso R . . . . .
H601 H 0.8077 0.7041 0.3046 0.0696 1.0000 Uiso R . . . . .
H602 H 0.7931 0.6030 0.2346 0.0700 1.0000 Uiso R . . . . .
H611 H 0.9799 0.5628 0.3131 0.0601 1.0000 Uiso R . . . . .
H613 H 0.9113 0.5094 0.3677 0.0600 1.0000 Uiso R . . . . .
H612 H 0.8476 0.4830 0.2742 0.0601 1.0000 Uiso R . . . . .
H671 H 0.2821 0.1916 0.4115 0.0290 1.0000 Uiso R . . . . .
H681 H 0.1362 0.0894 0.4538 0.0353 1.0000 Uiso R . . . . .
H701 H 0.3888 0.1239 0.6420 0.0443 1.0000 Uiso R . . . . .
H711 H 0.5348 0.2301 0.6031 0.0350 1.0000 Uiso R . . . . .
H722 H 0.1917 0.0093 0.6175 0.0752 1.0000 Uiso R . . . . .
H721 H 0.1029 0.0602 0.6036 0.0753 1.0000 Uiso R . . . . .
H723 H 0.1047 -0.0299 0.5296 0.0750 1.0000 Uiso R . . . . .
H781 H 0.6038 0.9304 0.7478 0.0311 1.0000 Uiso R . . . . .
H791 H 0.5914 1.0123 0.6602 0.0363 1.0000 Uiso R . . . . .
H811 H 0.8281 1.1465 0.5951 0.0824 1.0000 Uiso R . . . . .
H813 H 0.7562 1.1963 0.6507 0.0826 1.0000 Uiso R . . . . .
H812 H 0.6882 1.0964 0.5743 0.0825 1.0000 Uiso R . . . . .
H821 H 0.9505 1.1296 0.7051 0.0434 1.0000 Uiso R . . . . .
H831 H 0.9654 1.0472 0.7921 0.0360 1.0000 Uiso R . . . . .
H421 H -0.1576(17) 0.5535(18) 1.031(2) 0.022(2) 1.0000 Uiso D . . . . .
H311 H 0.509(2) 0.7686(15) 1.0856(14) 0.020(2) 1.0000 Uiso D . . . . .
H261 H 0.3140(19) 0.9767(18) 1.0463(16) 0.020(2) 1.0000 Uiso D . . . . .
H231 H 0.0894(19) 0.9267(19) 0.9734(16) 0.024(2) 1.0000 Uiso D . . . . .
H111 H 0.6644(17) 0.4943(15) 0.5724(12) 0.024(2) 1.0000 Uiso D . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 . C2 . C3 . 120.2(3) yes
Cl1 . C2 . C7 . 118.3(3) yes
C3 . C2 . C7 . 121.5(3) yes
C2 . C3 . C4 . 119.7(3) yes
C2 . C3 . H31 . 120.0 no
C4 . C3 . H31 . 120.3 no
C3 . C4 . C5 . 120.6(3) yes
C3 . C4 . H41 . 120.8 no
C5 . C4 . H41 . 118.6 no
C4 . C5 . C6 . 118.2(3) yes
C4 . C5 . C8 . 121.7(3) yes
C6 . C5 . C8 . 120.0(3) yes
C5 . C6 . C7 . 121.7(3) yes
C5 . C6 . H61 . 118.5 no
C7 . C6 . H61 . 119.8 no
C6 . C7 . C2 . 118.3(3) yes
C6 . C7 . H71 . 121.1 no
C2 . C7 . H71 . 120.6 no
C5 . C8 . C9 . 124.3(3) yes
C5 . C8 . C59 . 113.9(3) yes
C9 . C8 . C59 . 121.7(3) yes
C8 . C9 . C10 . 121.6(3) yes
C8 . C9 . C56 . 122.8(3) yes
C10 . C9 . C56 . 115.3(3) yes
C9 . C10 . N11 . 114.2(3) yes
C9 . C10 . H101 . 109.4 no
N11 . C10 . H101 . 107.5 no
C9 . C10 . H102 . 109.1 no
N11 . C10 . H102 . 106.8 no
H101 . C10 . H102 . 109.8 no
C10 . N11 . C12 . 112.6(2) yes
C10 . N11 . C55 . 109.5(2) yes
C12 . N11 . C55 . 109.8(2) yes
C10 . N11 . H111 . 108.9(14) no
C12 . N11 . H111 . 107.9(14) no
C55 . N11 . H111 . 108.1(14) no
N11 . C12 . C13 . 110.4(2) yes
N11 . C12 . H122 . 108.7 no
C13 . C12 . H122 . 110.0 no
N11 . C12 . H121 . 108.6 no
C13 . C12 . H121 . 109.4 no
H122 . C12 . H121 . 109.8 no
C12 . C13 . N14 . 111.2(2) yes
C12 . C13 . H132 . 107.7 no
N14 . C13 . H132 . 109.5 no
C12 . C13 . H131 . 109.4 no
N14 . C13 . H131 . 109.5 no
H132 . C13 . H131 . 109.6 no
C13 . N14 . C15 . 120.6(2) yes
C13 . N14 . C54 . 112.4(2) yes
C15 . N14 . C54 . 118.5(3) yes
N14 . C15 . C16 . 120.6(3) yes
N14 . C15 . C53 . 121.7(3) yes
C16 . C15 . C53 . 117.6(3) yes
C15 . C16 . C17 . 120.0(3) yes
C15 . C16 . H161 . 120.7 no
C17 . C16 . H161 . 119.3 no
C16 . C17 . O18 . 116.3(3) yes
C16 . C17 . C28 . 122.5(3) yes
O18 . C17 . C28 . 120.8(3) yes
C17 . O18 . C19 . 119.0(2) yes
O18 . C19 . C20 . 124.9(3) yes
O18 . C19 . C27 . 113.9(3) yes
C20 . C19 . C27 . 121.2(3) yes
C19 . C20 . C21 . 118.3(3) yes
C19 . C20 . H201 . 120.7 no
C21 . C20 . H201 . 121.0 no
C20 . C21 . C22 . 118.3(3) yes
C20 . C21 . C25 . 136.4(3) yes
C22 . C21 . C25 . 105.3(3) yes
C21 . C22 . N23 . 109.7(3) yes
C21 . C22 . N26 . 122.3(3) yes
N23 . C22 . N26 . 128.0(3) yes
C22 . N23 . C24 . 107.4(3) yes
C22 . N23 . H231 . 125.6(13) no
C24 . N23 . H231 . 126.4(13) no
N23 . C24 . C25 . 110.4(3) yes
N23 . C24 . H241 . 123.4 no
C25 . C24 . H241 . 126.1 no
C21 . C25 . C24 . 107.2(3) yes
C21 . C25 . H251 . 126.2 no
C24 . C25 . H251 . 126.6 no
C22 . N26 . C27 . 119.3(3) yes
C22 . N26 . H261 . 120.3(12) no
C27 . N26 . H261 . 120.1(12) no
C19 . C27 . N26 . 120.6(3) yes
C19 . C27 . H271 . 120.6 no
N26 . C27 . H271 . 118.8 no
C17 . C28 . C29 . 127.4(3) yes
C17 . C28 . C52 . 116.7(3) yes
C29 . C28 . C52 . 115.9(3) yes
C28 . C29 . O30 . 122.8(3) yes
C28 . C29 . N31 . 116.3(3) yes
O30 . C29 . N31 . 120.9(3) yes
C29 . N31 . S32 . 122.7(2) yes
C29 . N31 . H311 . 118.7(13) no
S32 . N31 . H311 . 117.5(13) no
N31 . S32 . O33 . 110.62(14) yes
N31 . S32 . O34 . 103.48(14) yes
O33 . S32 . O34 . 119.51(14) yes
N31 . S32 . C35 . 101.91(14) yes
O33 . S32 . C35 . 108.81(14) yes
O34 . S32 . C35 . 111.01(14) yes
S32 . C35 . C36 . 120.2(2) yes
S32 . C35 . C51 . 119.2(2) yes
C36 . C35 . C51 . 120.3(3) yes
C35 . C36 . C37 . 119.9(3) yes
C35 . C36 . H361 . 120.3 no
C37 . C36 . H361 . 119.8 no
C36 . C37 . N38 . 115.9(3) yes
C36 . C37 . C41 . 121.9(3) yes
N38 . C37 . C41 . 122.2(3) yes
C37 . N38 . O39 . 119.4(3) yes
C37 . N38 . O40 . 118.6(3) yes
O39 . N38 . O40 . 122.0(3) yes
C37 . C41 . N42 . 124.5(3) yes
C37 . C41 . C50 . 115.4(3) yes
N42 . C41 . C50 . 120.1(3) yes
C41 . N42 . C43 . 123.3(3) yes
C41 . N42 . H421 . 118.2(12) no
C43 . N42 . H421 . 118.5(12) no
N42 . C43 . C44 . 112.4(3) yes
N42 . C43 . H432 . 107.5 no
C44 . C43 . H432 . 107.7 no
N42 . C43 . H431 . 110.7 no
C44 . C43 . H431 . 109.6 no
H432 . C43 . H431 . 108.9 no
C43 . C44 . C45 . 110.2(3) yes
C43 . C44 . C49 . 111.6(3) yes
C45 . C44 . C49 . 110.3(3) yes
C43 . C44 . H441 . 107.7 no
C45 . C44 . H441 . 108.0 no
C49 . C44 . H441 . 109.0 no
C44 . C45 . C46 . 111.5(3) yes
C44 . C45 . H451 . 109.3 no
C46 . C45 . H451 . 108.7 no
C44 . C45 . H452 . 109.9 no
C46 . C45 . H452 . 108.4 no
H451 . C45 . H452 . 109.0 no
C45 . C46 . O47 . 112.5(3) yes
C45 . C46 . H461 . 109.3 no
O47 . C46 . H461 . 109.0 no
C45 . C46 . H462 . 108.7 no
O47 . C46 . H462 . 107.7 no
H461 . C46 . H462 . 109.6 no
C46 . O47 . C48 . 111.0(2) yes
O47 . C48 . C49 . 110.2(3) yes
O47 . C48 . H481 . 107.5 no
C49 . C48 . H481 . 109.8 no
O47 . C48 . H482 . 109.4 no
C49 . C48 . H482 . 109.4 no
H481 . C48 . H482 . 110.5 no
C44 . C49 . C48 . 110.6(3) yes
C44 . C49 . H491 . 109.7 no
C48 . C49 . H491 . 109.8 no
C44 . C49 . H492 . 108.4 no
C48 . C49 . H492 . 108.8 no
H491 . C49 . H492 . 109.5 no
C41 . C50 . C51 . 122.3(3) yes
C41 . C50 . H501 . 118.8 no
C51 . C50 . H501 . 118.8 no
C35 . C51 . C50 . 120.1(3) yes
C35 . C51 . H511 . 119.8 no
C50 . C51 . H511 . 120.1 no
C28 . C52 . C53 . 122.4(3) yes
C28 . C52 . H521 . 118.5 no
C53 . C52 . H521 . 119.1 no
C15 . C53 . C52 . 120.6(3) yes
C15 . C53 . H531 . 120.2 no
C52 . C53 . H531 . 119.1 no
N14 . C54 . C55 . 110.1(3) yes
N14 . C54 . H541 . 109.4 no
C55 . C54 . H541 . 107.9 no
N14 . C54 . H542 . 109.8 no
C55 . C54 . H542 . 110.2 no
H541 . C54 . H542 . 109.4 no
C54 . C55 . N11 . 111.0(2) yes
C54 . C55 . H552 . 109.6 no
N11 . C55 . H552 . 107.7 no
C54 . C55 . H551 . 109.7 no
N11 . C55 . H551 . 108.0 no
H552 . C55 . H551 . 110.8 no
C9 . C56 . C57 . 113.3(3) yes
C9 . C56 . H562 . 109.0 no
C57 . C56 . H562 . 109.0 no
C9 . C56 . H561 . 108.3 no
C57 . C56 . H561 . 108.6 no
H562 . C56 . H561 . 108.7 no
C56 . C57 . C58 . 112.4(3) yes
C56 . C57 . H572 . 108.4 no
C58 . C57 . H572 . 108.6 no
C56 . C57 . H571 . 108.7 no
C58 . C57 . H571 . 109.0 no
H572 . C57 . H571 . 109.7 no
C57 . C58 . C59 . 107.4(3) yes
C57 . C58 . C60 . 109.5(3) yes
C59 . C58 . C60 . 109.7(3) yes
C57 . C58 . C61 . 111.3(3) yes
C59 . C58 . C61 . 109.9(3) yes
C60 . C58 . C61 . 109.0(3) yes
C58 . C59 . C8 . 114.1(3) yes
C58 . C59 . H592 . 108.5 no
C8 . C59 . H592 . 107.9 no
C58 . C59 . H591 . 109.0 no
C8 . C59 . H591 . 107.8 no
H592 . C59 . H591 . 109.3 no
C58 . C60 . H603 . 109.1 no
C58 . C60 . H601 . 109.0 no
H603 . C60 . H601 . 109.7 no
C58 . C60 . H602 . 109.2 no
H603 . C60 . H602 . 109.8 no
H601 . C60 . H602 . 110.0 no
C58 . C61 . H611 . 109.9 no
C58 . C61 . H613 . 110.2 no
H611 . C61 . H613 . 109.9 no
C58 . C61 . H612 . 108.2 no
H611 . C61 . H612 . 109.3 no
H613 . C61 . H612 . 109.3 no
O63 . S62 . O64 . 112.07(14) yes
O63 . S62 . O65 . 110.58(14) yes
O64 . S62 . O65 . 114.98(14) yes
O63 . S62 . C66 . 104.97(14) yes
O64 . S62 . C66 . 106.42(15) yes
O65 . S62 . C66 . 107.10(15) yes
S62 . C66 . C67 . 119.4(3) yes
S62 . C66 . C71 . 120.6(3) yes
C67 . C66 . C71 . 120.0(3) yes
C66 . C67 . C68 . 119.5(3) yes
C66 . C67 . H671 . 119.9 no
C68 . C67 . H671 . 120.6 no
C67 . C68 . C69 . 121.1(3) yes
C67 . C68 . H681 . 119.6 no
C69 . C68 . H681 . 119.3 no
C68 . C69 . C70 . 118.5(3) yes
C68 . C69 . C72 . 120.8(4) yes
C70 . C69 . C72 . 120.7(4) yes
C69 . C70 . C71 . 121.0(4) yes
C69 . C70 . H701 . 119.3 no
C71 . C70 . H701 . 119.6 no
C70 . C71 . C66 . 119.8(3) yes
C70 . C71 . H711 . 120.4 no
C66 . C71 . H711 . 119.8 no
C69 . C72 . H722 . 109.8 no
C69 . C72 . H721 . 110.3 no
H722 . C72 . H721 . 109.9 no
C69 . C72 . H723 . 109.2 no
H722 . C72 . H723 . 108.6 no
H721 . C72 . H723 . 109.0 no
O74 . S73 . O75 . 111.47(15) yes
O74 . S73 . O76 . 113.47(14) yes
O75 . S73 . O76 . 111.73(14) yes
O74 . S73 . C77 . 107.61(15) yes
O75 . S73 . C77 . 105.21(15) yes
O76 . S73 . C77 . 106.80(16) yes
S73 . C77 . C78 . 119.8(3) yes
S73 . C77 . C83 . 120.0(3) yes
C78 . C77 . C83 . 120.2(3) yes
C77 . C78 . C79 . 119.2(3) yes
C77 . C78 . H781 . 120.1 no
C79 . C78 . H781 . 120.6 no
C78 . C79 . C80 . 121.4(4) yes
C78 . C79 . H791 . 119.4 no
C80 . C79 . H791 . 119.2 no
C79 . C80 . C81 . 120.1(4) yes
C79 . C80 . C82 . 118.2(4) yes
C81 . C80 . C82 . 121.6(4) yes
C80 . C81 . H811 . 109.6 no
C80 . C81 . H813 . 110.9 no
H811 . C81 . H813 . 108.7 no
C80 . C81 . H812 . 110.1 no
H811 . C81 . H812 . 108.9 no
H813 . C81 . H812 . 108.7 no
C80 . C82 . C83 . 121.4(4) yes
C80 . C82 . H821 . 118.8 no
C83 . C82 . H821 . 119.8 no
C77 . C83 . C82 . 119.5(4) yes
C77 . C83 . H831 . 120.0 no
C82 . C83 . H831 . 120.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C2 . 1.747(3) yes
C2 . C3 . 1.372(5) yes
C2 . C7 . 1.379(5) yes
C3 . C4 . 1.391(5) yes
C3 . H31 . 0.937 no
C4 . C5 . 1.385(5) yes
C4 . H41 . 0.945 no
C5 . C6 . 1.398(5) yes
C5 . C8 . 1.496(4) yes
C6 . C7 . 1.386(5) yes
C6 . H61 . 0.948 no
C7 . H71 . 0.945 no
C8 . C9 . 1.339(5) yes
C8 . C59 . 1.517(5) yes
C9 . C10 . 1.504(4) yes
C9 . C56 . 1.506(4) yes
C10 . N11 . 1.506(4) yes
C10 . H101 . 0.983 no
C10 . H102 . 0.981 no
N11 . C12 . 1.500(4) yes
N11 . C55 . 1.495(4) yes
N11 . H111 . 0.896(18) no
C12 . C13 . 1.515(4) yes
C12 . H122 . 0.983 no
C12 . H121 . 0.979 no
C13 . N14 . 1.464(4) yes
C13 . H132 . 0.971 no
C13 . H131 . 0.977 no
N14 . C15 . 1.378(4) yes
N14 . C54 . 1.461(4) yes
C15 . C16 . 1.416(4) yes
C15 . C53 . 1.408(4) yes
C16 . C17 . 1.382(4) yes
C16 . H161 . 0.934 no
C17 . O18 . 1.399(4) yes
C17 . C28 . 1.398(4) yes
O18 . C19 . 1.378(3) yes
C19 . C20 . 1.386(4) yes
C19 . C27 . 1.384(4) yes
C20 . C21 . 1.384(4) yes
C20 . H201 . 0.937 no
C21 . C22 . 1.419(4) yes
C21 . C25 . 1.427(4) yes
C22 . N23 . 1.354(4) yes
C22 . N26 . 1.336(4) yes
N23 . C24 . 1.382(4) yes
N23 . H231 . 0.859(18) no
C24 . C25 . 1.362(5) yes
C24 . H241 . 0.941 no
C25 . H251 . 0.938 no
N26 . C27 . 1.355(4) yes
N26 . H261 . 0.867(18) no
C27 . H271 . 0.939 no
C28 . C29 . 1.480(4) yes
C28 . C52 . 1.394(4) yes
C29 . O30 . 1.219(4) yes
C29 . N31 . 1.384(4) yes
N31 . S32 . 1.663(3) yes
N31 . H311 . 0.852(18) no
S32 . O33 . 1.429(2) yes
S32 . O34 . 1.430(2) yes
S32 . C35 . 1.744(3) yes
C35 . C36 . 1.369(4) yes
C35 . C51 . 1.404(4) yes
C36 . C37 . 1.391(4) yes
C36 . H361 . 0.946 no
C37 . N38 . 1.441(4) yes
C37 . C41 . 1.427(4) yes
N38 . O39 . 1.238(4) yes
N38 . O40 . 1.232(4) yes
C41 . N42 . 1.342(4) yes
C41 . C50 . 1.427(4) yes
N42 . C43 . 1.456(4) yes
N42 . H421 . 0.859(18) no
C43 . C44 . 1.542(4) yes
C43 . H432 . 0.977 no
C43 . H431 . 0.982 no
C44 . C45 . 1.525(4) yes
C44 . C49 . 1.525(4) yes
C44 . H441 . 0.995 no
C45 . C46 . 1.517(5) yes
C45 . H451 . 0.980 no
C45 . H452 . 0.977 no
C46 . O47 . 1.437(4) yes
C46 . H461 . 0.984 no
C46 . H462 . 0.983 no
O47 . C48 . 1.431(4) yes
C48 . C49 . 1.512(5) yes
C48 . H481 . 0.980 no
C48 . H482 . 0.978 no
C49 . H491 . 0.974 no
C49 . H492 . 0.983 no
C50 . C51 . 1.361(4) yes
C50 . H501 . 0.942 no
C51 . H511 . 0.950 no
C52 . C53 . 1.377(4) yes
C52 . H521 . 0.951 no
C53 . H531 . 0.938 no
C54 . C55 . 1.519(4) yes
C54 . H541 . 0.977 no
C54 . H542 . 0.980 no
C55 . H552 . 0.977 no
C55 . H551 . 0.985 no
C56 . C57 . 1.526(5) yes
C56 . H562 . 0.976 no
C56 . H561 . 0.976 no
C57 . C58 . 1.530(5) yes
C57 . H572 . 0.983 no
C57 . H571 . 0.976 no
C58 . C59 . 1.529(5) yes
C58 . C60 . 1.528(5) yes
C58 . C61 . 1.529(6) yes
C59 . H592 . 0.982 no
C59 . H591 . 0.984 no
C60 . H603 . 0.972 no
C60 . H601 . 0.974 no
C60 . H602 . 0.968 no
C61 . H611 . 0.974 no
C61 . H613 . 0.978 no
C61 . H612 . 0.968 no
S62 . O63 . 1.473(2) yes
S62 . O64 . 1.443(2) yes
S62 . O65 . 1.455(2) yes
S62 . C66 . 1.780(3) yes
C66 . C67 . 1.393(5) yes
C66 . C71 . 1.381(5) yes
C67 . C68 . 1.386(5) yes
C67 . H671 . 0.951 no
C68 . C69 . 1.392(6) yes
C68 . H681 . 0.950 no
C69 . C70 . 1.384(6) yes
C69 . C72 . 1.517(5) yes
C70 . C71 . 1.391(5) yes
C70 . H701 . 0.944 no
C71 . H711 . 0.948 no
C72 . H722 . 0.966 no
C72 . H721 . 0.972 no
C72 . H723 . 0.967 no
S73 . O74 . 1.445(2) yes
S73 . O75 . 1.475(2) yes
S73 . O76 . 1.463(2) yes
S73 . C77 . 1.770(4) yes
C77 . C78 . 1.391(5) yes
C77 . C83 . 1.392(5) yes
C78 . C79 . 1.385(5) yes
C78 . H781 . 0.945 no
C79 . C80 . 1.392(6) yes
C79 . H791 . 0.947 no
C80 . C81 . 1.510(6) yes
C80 . C82 . 1.389(6) yes
C81 . H811 . 0.963 no
C81 . H813 . 0.964 no
C81 . H812 . 0.964 no
C82 . C83 . 1.381(6) yes
C82 . H821 . 0.945 no
C83 . H831 . 0.951 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C7 . H71 . O64 2_766 171 0.95 2.49 3.428(5) yes
C12 . H122 . O74 . 128 0.98 2.34 3.043(5) yes
C24 . H241 . O74 1_455 161 0.94 2.30 3.205(5) yes
C45 . H451 . C16 1_455 170 0.98 2.60 3.569(5) yes
C53 . H531 . O33 2_667 164 0.94 2.54 3.451(5) yes
C54 . H541 . O33 2_667 134 0.98 2.46 3.209(5) yes
C55 . H551 . O65 . 126 0.99 2.44 3.121(5) yes
N42 . H421 . O30 2_567 139.9(19) 0.859 2.205 2.915(5) yes
N42 . H421 . O39 . 129.7(17) 0.859 2.023 2.655(5) yes
N31 . H311 . O47 1_655 151(3) 0.852 2.061 2.837(5) yes
N26 . H261 . O75 2_677 173(2) 0.867 1.755 2.617(5) yes
N23 . H231 . O76 2_677 154(3) 0.859 2.055 2.851(5) yes
N11 . H111 . O63 . 168(2) 0.896 1.891 2.772(5) yes
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-7 11 11 x .
-11 6 13 x .
-11 8 11 x .
-10 12 10 x .
-9 13 9 x .
-8 13 9 x .
-14 10 5 x .
-9 6 12 x .
-8 10 11 x .
-11 11 9 x .
-10 10 10 x .
-11 10 7 x .
-7 11 11 x .
-7 11 11 x .
-7 11 11 x .
-11 10 9 x .
-13 10 7 x .
-9 12 10 x .
-6 10 10 x .
-12 11 8 x .
-9 6 12 x .
-8 14 6 x .
-7 15 4 x .
8 -19 6 x .
-9 8 11 x .
-8 10 13 x .
-5 6 17 x .
-7 5 16 x .
-9 5 15 x .
-8 6 15 x .
-7 10 10 x .
-13 10 6 x .
-14 9 7 x .
-13 9 8 x .
-13 9 9 x .
-12 9 10 x .
-11 9 10 x .
-10 11 10 x .
-12 8 11 x .
-10 8 11 x .
-12 7 12 x .
-9 9 10 x .
-7 9 12 x .
-9 7 14 x .
-12 10 8 x .
-10 8 12 x .
-9 9 12 x .
