# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 2377711'
loop_
_audit_author_name
_audit_author_address
'Eliska Zmeskalova'
;Institute of Physics of the Czech Academy of Sciences
Czech Republic
;
_audit_update_record             
;
2024-08-15 deposited with the CCDC.	2025-02-12 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   12.2261(5)
_cell_length_b                   14.0822(6)
_cell_length_c                   15.1150(5)
_cell_angle_alpha                67.388(4)
_cell_angle_beta                 72.278(3)
_cell_angle_gamma                74.731(3)
_cell_volume                     2256.41(17)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

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'
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'
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'
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'


_cell_formula_units_Z            2

# Given Formula = C45 H50 Cl1 N7 O7 S1 
# Dc =      1.28 Fooo =    916.00 Mu =     16.51 M =    868.45
# Found Formula = C47 H53.00 Cl1 N8 O7 S1 
# Dc =      1.34 FOOO =    959.99 Mu =     16.83 M =    909.50

_chemical_formula_sum            'C47 H53.00 Cl1 N8 O7 S1'
_chemical_formula_moiety         'C47 H53.00 Cl1 N8 O7 S1'
_chemical_compound_source        ?
_chemical_formula_weight         909.50


_cell_measurement_reflns_used    5652
_cell_measurement_theta_min      4
_cell_measurement_theta_max      73
_cell_measurement_temperature    95

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.024
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_max          0.080

_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             959.994
_exptl_absorpt_coefficient_mu    1.683

# Sheldrick geometric approximatio 0.90 0.96 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_T_max  0.96
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      95
_diffrn_reflns_number            16343
_reflns_number_total             8774
_diffrn_reflns_av_R_equivalents  0.035
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 8774 
# Theoretical number of reflections is about 18111 


_diffrn_reflns_theta_min         3.253
_diffrn_reflns_theta_max         73.242
_diffrn_measured_fraction_theta_max 0.969

_diffrn_reflns_theta_full        67.150
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -14
_reflns_limit_h_max              15
_reflns_limit_k_min              -15
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   1.51
_oxford_diffrn_Wilson_scale      0.05

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.54
_refine_diff_density_max         0.45


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     12
_refine_ls_number_parameters     589
_refine_ls_number_reflns         8773
_oxford_refine_ls_R_factor_ref   0.0535
_refine_ls_wR_factor_ref         0.0978
_refine_ls_goodness_of_fit_ref   0.9919
_refine_ls_shift/su_max          0.0054282
_refine_ls_shift/su_mean         0.0008775


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        8773
_refine_ls_R_factor_all          0.0535
_refine_ls_wR_factor_all         0.0978

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7093
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_gt          0.0895


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 1.09P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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 0.21951(4) 0.02090(4) 1.05734(4) 0.0261 1.0000 Uani . . . . . .
C2 C 0.07254(17) 0.07687(14) 1.06850(15) 0.0192 1.0000 Uani . . . . . .
C3 C 0.00779(18) 0.08337(15) 1.15903(14) 0.0202 1.0000 Uani . . . . . .
C4 C -0.10913(17) 0.13041(15) 1.16836(14) 0.0197 1.0000 Uani . . . . . .
C5 C -0.16040(17) 0.16908(14) 1.08796(14) 0.0181 1.0000 Uani . . . . . .
C6 C -0.28394(16) 0.22349(15) 1.09307(13) 0.0177 1.0000 Uani . . . . . .
C7 C -0.31946(16) 0.31959(14) 1.09831(13) 0.0172 1.0000 Uani . . . . . .
C8 C -0.24183(17) 0.38525(15) 1.10147(14) 0.0186 1.0000 Uani . . . . . .
N9 N -0.21682(14) 0.46923(12) 1.00623(12) 0.0172 1.0000 Uani . . . . . .
C10 C -0.12991(17) 0.42580(15) 0.93489(14) 0.0203 1.0000 Uani . . . . . .
C11 C -0.10047(18) 0.51033(15) 0.83622(14) 0.0200 1.0000 Uani . . . . . .
N12 N -0.05990(14) 0.59301(12) 0.84779(11) 0.0164 1.0000 Uani . . . . . .
C13 C -0.00680(16) 0.66319(14) 0.76001(13) 0.0158 1.0000 Uani . . . . . .
C14 C -0.04954(16) 0.77077(14) 0.73020(14) 0.0167 1.0000 Uani . . . . . .
C15 C 0.00890(16) 0.83714(14) 0.64519(14) 0.0171 1.0000 Uani . . . . . .
C16 C 0.10940(15) 0.79983(14) 0.58533(13) 0.0147 1.0000 Uani . . . . . .
C17 C 0.16783(15) 0.87804(14) 0.49743(13) 0.0147 1.0000 Uani D . . . . .
O18 O 0.17003(12) 0.96469(10) 0.49573(10) 0.0177 1.0000 Uani . . . . . .
N19 N 0.21865(14) 0.84663(12) 0.41567(11) 0.0153 1.0000 Uani D . . . . .
S20 S 0.30625(4) 0.91119(3) 0.31569(3) 0.0134 1.0000 Uani D . . . . .
O21 O 0.24992(11) 1.01535(10) 0.27491(9) 0.0170 1.0000 Uani . . . . . .
O22 O 0.34457(11) 0.84160(10) 0.25890(9) 0.0166 1.0000 Uani . . . . . .
C23 C 0.42310(15) 0.91475(14) 0.35724(13) 0.0139 1.0000 Uani . . . . . .
C24 C 0.49350(16) 0.82030(14) 0.39936(13) 0.0162 1.0000 Uani . . . . . .
C25 C 0.58643(16) 0.82163(13) 0.43054(13) 0.0149 1.0000 Uani . . . . . .
C26 C 0.61673(15) 0.91625(13) 0.42263(13) 0.0136 1.0000 Uani D . . . . .
N27 N 0.70639(13) 0.91403(11) 0.45682(11) 0.0152 1.0000 Uani D . . . . .
C28 C 0.77778(16) 0.81912(13) 0.50675(14) 0.0156 1.0000 Uani D . . . . .
C29 C 0.87240(15) 0.76934(13) 0.43695(13) 0.0150 1.0000 Uani . . . . . .
C30 C 0.95079(16) 0.84723(14) 0.36182(14) 0.0184 1.0000 Uani . . . . . .
C31 C 1.05494(17) 0.79259(15) 0.30320(15) 0.0208 1.0000 Uani . . . . . .
O32 O 1.12095(11) 0.70956(10) 0.36733(10) 0.0202 1.0000 Uani . . . . . .
C33 C 1.05172(17) 0.63100(15) 0.43146(16) 0.0229 1.0000 Uani . . . . . .
C34 C 0.94515(16) 0.67433(14) 0.49742(14) 0.0184 1.0000 Uani . . . . . .
H341 H 0.9719 0.6950 0.5426 0.0228 1.0000 Uiso R . . . . .
H342 H 0.8975 0.6196 0.5381 0.0233 1.0000 Uiso R . . . . .
H331 H 1.1017 0.5739 0.4717 0.0285 1.0000 Uiso R . . . . .
H332 H 1.0270 0.6033 0.3904 0.0277 1.0000 Uiso R . . . . .
H311 H 1.1079 0.8420 0.2602 0.0249 1.0000 Uiso R . . . . .
H312 H 1.0291 0.7652 0.2628 0.0253 1.0000 Uiso R . . . . .
H302 H 0.9781 0.8784 0.3978 0.0212 1.0000 Uiso R . . . . .
H301 H 0.9073 0.9021 0.3159 0.0229 1.0000 Uiso R . . . . .
H291 H 0.8332 0.7475 0.4002 0.0175 1.0000 Uiso R . . . . .
H282 H 0.8179 0.8399 0.5434 0.0186 1.0000 Uiso R . . . . .
H281 H 0.7275 0.7678 0.5536 0.0198 1.0000 Uiso R . . . . .
H271 H 0.7229(17) 0.9722(12) 0.4500(16) 0.0183(19) 1.0000 Uiso D . . . . .
C35 C 0.54299(15) 1.00986(13) 0.37887(13) 0.0137 1.0000 Uani . . . . . .
C36 C 0.44700(15) 1.00816(14) 0.34847(13) 0.0145 1.0000 Uani . . . . . .
H361 H 0.3988 1.0740 0.3215 0.0175 1.0000 Uiso R . . . . .
N37 N 0.56290(13) 1.11134(11) 0.36609(11) 0.0143 1.0000 Uani . . . . . .
O38 O 0.48983(12) 1.18858(10) 0.33782(10) 0.0193 1.0000 Uani . . . . . .
O39 O 0.65255(12) 1.11868(10) 0.38379(10) 0.0204 1.0000 Uani . . . . . .
H251 H 0.6325 0.7569 0.4587 0.0183 1.0000 Uiso R . . . . .
H241 H 0.4765 0.7559 0.4057 0.0199 1.0000 Uiso R . . . . .
H191 H 0.2048(19) 0.7905(14) 0.4164(13) 0.0190(19) 1.0000 Uiso D . . . . .
C40 C 0.14916(16) 0.69174(14) 0.61433(13) 0.0150 1.0000 Uani . . . . . .
C41 C 0.09384(16) 0.62467(14) 0.70053(14) 0.0164 1.0000 Uani . . . . . .
H411 H 0.1239 0.5515 0.7204 0.0200 1.0000 Uiso R . . . . .
O42 O 0.24428(12) 0.65273(10) 0.55213(9) 0.0186 1.0000 Uani . . . . . .
C43 C 0.33742(16) 0.58646(14) 0.59285(13) 0.0160 1.0000 Uani . . . . . .
C44 C 0.40827(16) 0.62524(14) 0.62140(13) 0.0172 1.0000 Uani . . . . . .
C45 C 0.50668(16) 0.55648(14) 0.65039(13) 0.0166 1.0000 Uani . . . . . .
C46 C 0.52229(16) 0.45350(14) 0.64871(13) 0.0171 1.0000 Uani D . . . . .
N47 N 0.62407(15) 0.39991(13) 0.67732(12) 0.0203 1.0000 Uani D . . . . .
C48 C 0.67263(17) 0.46552(15) 0.69581(14) 0.0213 1.0000 Uani D . . . . .
C49 C 0.60432(17) 0.56167(15) 0.68049(15) 0.0211 1.0000 Uani . . . . . .
H491 H 0.6193 0.6190 0.6881 0.0256 1.0000 Uiso R . . . . .
H481 H 0.7448 0.4440 0.7162 0.0264 1.0000 Uiso R . . . . .
H471 H 0.6503(17) 0.3339(13) 0.6873(18) 0.0256(19) 1.0000 Uiso D . . . . .
N50 N 0.45315(15) 0.41500(12) 0.62253(12) 0.0196 1.0000 Uani . . . . . .
C51 C 0.36092(17) 0.48350(14) 0.59377(14) 0.0189 1.0000 Uani . . . . . .
H511 H 0.3082 0.4596 0.5730 0.0226 1.0000 Uiso R . . . . .
H441 H 0.3913 0.6957 0.6207 0.0207 1.0000 Uiso R . . . . .
H151 H -0.0190 0.9108 0.6242 0.0205 1.0000 Uiso R . . . . .
H141 H -0.1184 0.7982 0.7692 0.0207 1.0000 Uiso R . . . . .
C52 C -0.14770(16) 0.63744(14) 0.91872(14) 0.0183 1.0000 Uani . . . . . .
C53 C -0.17522(17) 0.55165(14) 1.01700(14) 0.0190 1.0000 Uani . . . . . .
H531 H -0.2374 0.5812 1.0635 0.0235 1.0000 Uiso R . . . . .
H532 H -0.1048 0.5227 1.0442 0.0235 1.0000 Uiso R . . . . .
H521 H -0.1141 0.6902 0.9262 0.0214 1.0000 Uiso R . . . . .
H522 H -0.2193 0.6711 0.8931 0.0219 1.0000 Uiso R . . . . .
H111 H -0.1712 0.5410 0.8082 0.0245 1.0000 Uiso R . . . . .
H112 H -0.0384 0.4795 0.7898 0.0246 1.0000 Uiso R . . . . .
H102 H -0.0569 0.3913 0.9587 0.0239 1.0000 Uiso R . . . . .
H101 H -0.1621 0.3747 0.9241 0.0240 1.0000 Uiso R . . . . .
H82 H -0.2820 0.4172 1.1528 0.0228 1.0000 Uiso R . . . . .
H81 H -0.1699 0.3420 1.1197 0.0223 1.0000 Uiso R . . . . .
C54 C -0.44093(17) 0.37771(15) 1.09137(15) 0.0210 1.0000 Uani . . . . . .
C55 C -0.52573(17) 0.31204(16) 1.09704(15) 0.0212 1.0000 Uani . . . . . .
C56 C -0.46888(17) 0.23465(16) 1.04080(14) 0.0211 1.0000 Uani . . . . . .
C57 C -0.36474(17) 0.16442(15) 1.08361(15) 0.0204 1.0000 Uani . . . . . .
H571 H -0.3952 0.1171 1.1499 0.0256 1.0000 Uiso R . . . . .
H572 H -0.3192 0.1211 1.0424 0.0255 1.0000 Uiso R . . . . .
C58 C -0.55573(19) 0.16689(18) 1.05387(17) 0.0282 1.0000 Uani . . . . . .
H582 H -0.5203 0.1157 1.0214 0.0428 1.0000 Uiso R . . . . .
H583 H -0.5847 0.1300 1.1241 0.0425 1.0000 Uiso R . . . . .
H581 H -0.6216 0.2091 1.0261 0.0427 1.0000 Uiso R . . . . .
C59 C -0.4263(2) 0.29224(18) 0.93073(15) 0.0293 1.0000 Uani . . . . . .
H592 H -0.3940 0.2431 0.8947 0.0454 1.0000 Uiso R . . . . .
H593 H -0.3660 0.3321 0.9217 0.0448 1.0000 Uiso R . . . . .
H591 H -0.4900 0.3405 0.9033 0.0448 1.0000 Uiso R . . . . .
H552 H -0.5535 0.2712 1.1660 0.0256 1.0000 Uiso R . . . . .
H551 H -0.5932 0.3588 1.0704 0.0263 1.0000 Uiso R . . . . .
H542 H -0.4700 0.4106 1.1434 0.0251 1.0000 Uiso R . . . . .
H541 H -0.4341 0.4358 1.0277 0.0247 1.0000 Uiso R . . . . .
C60 C -0.09287(17) 0.15724(15) 0.99848(14) 0.0202 1.0000 Uani . . . . . .
C61 C 0.02373(18) 0.11248(15) 0.98777(14) 0.0209 1.0000 Uani . . . . . .
H611 H 0.0699 0.1076 0.9263 0.0256 1.0000 Uiso R . . . . .
H601 H -0.1284 0.1803 0.9442 0.0243 1.0000 Uiso R . . . . .
H41 H -0.1541 0.1356 1.2312 0.0250 1.0000 Uiso R . . . . .
H31 H 0.0429 0.0562 1.2146 0.0252 1.0000 Uiso R . . . . .
N62 N 0.1488(2) 0.33107(19) 0.75288(19) 0.0460 1.0000 Uani . . . . . .
C63 C 0.2283(2) 0.2828(2) 0.78368(18) 0.0369 1.0000 Uani . . . . . .
C64 C 0.3297(3) 0.2206(3) 0.8221(2) 0.0519 1.0000 Uani . . . . . .
H642 H 0.3119 0.2052 0.8932 0.0795 1.0000 Uiso R . . . . .
H641 H 0.3941 0.2578 0.7889 0.0795 1.0000 Uiso R . . . . .
H643 H 0.3455 0.1552 0.8088 0.0800 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.26(4)
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(2) yes
C2 . C3 . 1.381(3) yes
C2 . C61 . 1.383(3) yes
C3 . C4 . 1.397(3) yes
C3 . H31 . 0.961 no
C4 . C5 . 1.393(3) yes
C4 . H41 . 0.961 no
C5 . C6 . 1.496(3) yes
C5 . C60 . 1.400(3) yes
C6 . C7 . 1.334(3) yes
C6 . C57 . 1.516(3) yes
C7 . C8 . 1.511(3) yes
C7 . C54 . 1.508(3) yes
C8 . N9 . 1.476(2) yes
C8 . H82 . 0.983 no
C8 . H81 . 0.977 no
N9 . C10 . 1.461(2) yes
N9 . C53 . 1.463(2) yes
C10 . C11 . 1.518(3) yes
C10 . H102 . 0.998 no
C10 . H101 . 0.988 no
C11 . N12 . 1.465(2) yes
C11 . H111 . 0.999 no
C11 . H112 . 0.997 no
N12 . C13 . 1.401(2) yes
N12 . C52 . 1.468(2) yes
C13 . C14 . 1.405(3) yes
C13 . C41 . 1.402(3) yes
C14 . C15 . 1.380(3) yes
C14 . H141 . 0.952 no
C15 . C16 . 1.398(3) yes
C15 . H151 . 0.958 no
C16 . C17 . 1.483(2) yes
C16 . C40 . 1.404(2) yes
C17 . O18 . 1.218(2) yes
C17 . N19 . 1.385(2) yes
N19 . S20 . 1.6518(15) yes
N19 . H191 . 0.846(16) no
S20 . O21 . 1.4271(13) yes
S20 . O22 . 1.4412(14) yes
S20 . C23 . 1.7453(18) yes
C23 . C24 . 1.412(2) yes
C23 . C36 . 1.370(3) yes
C24 . C25 . 1.363(3) yes
C24 . H241 . 0.946 no
C25 . C26 . 1.427(2) yes
C25 . H251 . 0.952 no
C26 . N27 . 1.336(2) yes
C26 . C35 . 1.433(2) yes
N27 . C28 . 1.459(2) yes
N27 . H271 . 0.855(16) no
C28 . C29 . 1.530(3) yes
C28 . H282 . 0.999 no
C28 . H281 . 0.988 no
C29 . C30 . 1.531(2) yes
C29 . C34 . 1.531(2) yes
C29 . H291 . 1.001 no
C30 . C31 . 1.523(3) yes
C30 . H302 . 0.986 no
C30 . H301 . 0.978 no
C31 . O32 . 1.437(2) yes
C31 . H311 . 0.980 no
C31 . H312 . 0.992 no
O32 . C33 . 1.431(2) yes
C33 . C34 . 1.524(3) yes
C33 . H331 . 0.991 no
C33 . H332 . 0.995 no
C34 . H341 . 0.997 no
C34 . H342 . 0.982 no
C35 . C36 . 1.393(3) yes
C35 . N37 . 1.443(2) yes
C36 . H361 . 0.970 no
N37 . O38 . 1.236(2) yes
N37 . O39 . 1.242(2) yes
C40 . C41 . 1.379(3) yes
C40 . O42 . 1.390(2) yes
C41 . H411 . 0.957 no
O42 . C43 . 1.404(2) yes
C43 . C44 . 1.376(3) yes
C43 . C51 . 1.397(3) yes
C44 . C45 . 1.399(3) yes
C44 . H441 . 0.955 no
C45 . C46 . 1.421(3) yes
C45 . C49 . 1.428(3) yes
C46 . N47 . 1.374(2) yes
C46 . N50 . 1.332(3) yes
N47 . C48 . 1.368(3) yes
N47 . H471 . 0.869(16) no
C48 . C49 . 1.366(3) yes
C48 . H481 . 0.958 no
C49 . H491 . 0.928 no
N50 . C51 . 1.339(3) yes
C51 . H511 . 0.972 no
C52 . C53 . 1.520(3) yes
C52 . H521 . 0.995 no
C52 . H522 . 0.994 no
C53 . H531 . 0.989 no
C53 . H532 . 0.990 no
C54 . C55 . 1.526(3) yes
C54 . H542 . 0.991 no
C54 . H541 . 0.992 no
C55 . C56 . 1.532(3) yes
C55 . H552 . 0.980 no
C55 . H551 . 0.994 no
C56 . C57 . 1.538(3) yes
C56 . C58 . 1.529(3) yes
C56 . C59 . 1.534(3) yes
C57 . H571 . 0.988 no
C57 . H572 . 0.986 no
C58 . H582 . 0.962 no
C58 . H583 . 0.983 no
C58 . H581 . 0.970 no
C59 . H592 . 0.973 no
C59 . H593 . 0.987 no
C59 . H591 . 0.970 no
C60 . C61 . 1.386(3) yes
C60 . H601 . 0.952 no
C61 . H611 . 0.946 no
N62 . C63 . 1.143(4) yes
C63 . C64 . 1.454(4) yes
C64 . H642 . 0.976 no
C64 . H641 . 0.959 no
C64 . H643 . 0.975 no
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 . 118.47(15) yes
Cl1 . C2 . C61 . 119.79(16) yes
C3 . C2 . C61 . 121.74(18) yes
C2 . C3 . C4 . 119.05(18) yes
C2 . C3 . H31 . 120.3 no
C4 . C3 . H31 . 120.6 no
C3 . C4 . C5 . 120.66(19) yes
C3 . C4 . H41 . 119.1 no
C5 . C4 . H41 . 120.2 no
C4 . C5 . C6 . 122.79(18) yes
C4 . C5 . C60 . 118.43(18) yes
C6 . C5 . C60 . 118.77(17) yes
C5 . C6 . C7 . 123.11(17) yes
C5 . C6 . C57 . 114.78(17) yes
C7 . C6 . C57 . 121.94(17) yes
C6 . C7 . C8 . 124.64(17) yes
C6 . C7 . C54 . 122.13(18) yes
C8 . C7 . C54 . 112.96(16) yes
C7 . C8 . N9 . 110.58(15) yes
C7 . C8 . H82 . 108.9 no
N9 . C8 . H82 . 108.5 no
C7 . C8 . H81 . 110.8 no
N9 . C8 . H81 . 111.1 no
H82 . C8 . H81 . 106.7 no
C8 . N9 . C10 . 109.46(15) yes
C8 . N9 . C53 . 110.89(15) yes
C10 . N9 . C53 . 110.15(15) yes
N9 . C10 . C11 . 111.00(16) yes
N9 . C10 . H102 . 110.8 no
C11 . C10 . H102 . 108.6 no
N9 . C10 . H101 . 109.1 no
C11 . C10 . H101 . 107.4 no
H102 . C10 . H101 . 109.9 no
C10 . C11 . N12 . 110.43(16) yes
C10 . C11 . H111 . 109.6 no
N12 . C11 . H111 . 109.1 no
C10 . C11 . H112 . 109.6 no
N12 . C11 . H112 . 109.4 no
H111 . C11 . H112 . 108.8 no
C11 . N12 . C13 . 115.25(15) yes
C11 . N12 . C52 . 110.78(15) yes
C13 . N12 . C52 . 117.18(15) yes
N12 . C13 . C14 . 122.47(17) yes
N12 . C13 . C41 . 118.70(16) yes
C14 . C13 . C41 . 118.82(16) yes
C13 . C14 . C15 . 120.16(17) yes
C13 . C14 . H141 . 120.0 no
C15 . C14 . H141 . 119.9 no
C14 . C15 . C16 . 121.58(17) yes
C14 . C15 . H151 . 121.0 no
C16 . C15 . H151 . 117.4 no
C15 . C16 . C17 . 117.28(16) yes
C15 . C16 . C40 . 117.69(16) yes
C17 . C16 . C40 . 125.00(17) yes
C16 . C17 . O18 . 123.01(17) yes
C16 . C17 . N19 . 115.32(16) yes
O18 . C17 . N19 . 121.66(16) yes
C17 . N19 . S20 . 124.37(13) yes
C17 . N19 . H191 . 118.6(11) no
S20 . N19 . H191 . 117.0(11) no
N19 . S20 . O21 . 110.47(8) yes
N19 . S20 . O22 . 102.56(8) yes
O21 . S20 . O22 . 120.12(8) yes
N19 . S20 . C23 . 104.48(8) yes
O21 . S20 . C23 . 109.03(8) yes
O22 . S20 . C23 . 108.98(8) yes
S20 . C23 . C24 . 119.29(14) yes
S20 . C23 . C36 . 120.45(14) yes
C24 . C23 . C36 . 120.25(17) yes
C23 . C24 . C25 . 120.14(17) yes
C23 . C24 . H241 . 120.1 no
C25 . C24 . H241 . 119.8 no
C24 . C25 . C26 . 122.40(16) yes
C24 . C25 . H251 . 118.5 no
C26 . C25 . H251 . 119.1 no
C25 . C26 . N27 . 120.53(16) yes
C25 . C26 . C35 . 115.25(16) yes
N27 . C26 . C35 . 124.20(16) yes
C26 . N27 . C28 . 124.73(15) yes
C26 . N27 . H271 . 118.1(11) no
C28 . N27 . H271 . 117.1(11) no
N27 . C28 . C29 . 113.95(15) yes
N27 . C28 . H282 . 106.3 no
C29 . C28 . H282 . 107.3 no
N27 . C28 . H281 . 109.7 no
C29 . C28 . H281 . 109.7 no
H282 . C28 . H281 . 109.8 no
C28 . C29 . C30 . 111.23(15) yes
C28 . C29 . C34 . 109.01(15) yes
C30 . C29 . C34 . 110.08(15) yes
C28 . C29 . H291 . 108.0 no
C30 . C29 . H291 . 108.2 no
C34 . C29 . H291 . 110.3 no
C29 . C30 . C31 . 110.58(15) yes
C29 . C30 . H302 . 108.2 no
C31 . C30 . H302 . 109.7 no
C29 . C30 . H301 . 110.3 no
C31 . C30 . H301 . 108.5 no
H302 . C30 . H301 . 109.5 no
C30 . C31 . O32 . 110.94(16) yes
C30 . C31 . H311 . 109.4 no
O32 . C31 . H311 . 106.0 no
C30 . C31 . H312 . 110.5 no
O32 . C31 . H312 . 110.2 no
H311 . C31 . H312 . 109.6 no
C31 . O32 . C33 . 110.36(14) yes
O32 . C33 . C34 . 111.51(15) yes
O32 . C33 . H331 . 107.6 no
C34 . C33 . H331 . 110.4 no
O32 . C33 . H332 . 108.4 no
C34 . C33 . H332 . 110.0 no
H331 . C33 . H332 . 108.8 no
C29 . C34 . C33 . 111.44(16) yes
C29 . C34 . H341 . 109.3 no
C33 . C34 . H341 . 108.6 no
C29 . C34 . H342 . 110.1 no
C33 . C34 . H342 . 109.5 no
H341 . C34 . H342 . 107.7 no
C26 . C35 . C36 . 122.21(16) yes
C26 . C35 . N37 . 121.49(16) yes
C36 . C35 . N37 . 116.29(15) yes
C35 . C36 . C23 . 119.73(16) yes
C35 . C36 . H361 . 118.4 no
C23 . C36 . H361 . 121.9 no
C35 . N37 . O38 . 118.79(15) yes
C35 . N37 . O39 . 119.29(14) yes
O38 . N37 . O39 . 121.93(15) yes
C16 . C40 . C41 . 121.47(17) yes
C16 . C40 . O42 . 118.34(16) yes
C41 . C40 . O42 . 120.16(16) yes
C13 . C41 . C40 . 120.22(17) yes
C13 . C41 . H411 . 119.4 no
C40 . C41 . H411 . 120.3 no
C40 . O42 . C43 . 117.68(14) yes
O42 . C43 . C44 . 120.47(16) yes
O42 . C43 . C51 . 117.10(17) yes
C44 . C43 . C51 . 122.14(17) yes
C43 . C44 . C45 . 116.52(17) yes
C43 . C44 . H441 . 121.5 no
C45 . C44 . H441 . 122.0 no
C44 . C45 . C46 . 116.77(18) yes
C44 . C45 . C49 . 136.61(18) yes
C46 . C45 . C49 . 106.58(16) yes
C45 . C46 . N47 . 107.58(17) yes
C45 . C46 . N50 . 127.02(17) yes
N47 . C46 . N50 . 125.39(17) yes
C46 . N47 . C48 . 108.73(16) yes
C46 . N47 . H471 . 125.8(11) no
C48 . N47 . H471 . 125.2(11) no
N47 . C48 . C49 . 110.32(18) yes
N47 . C48 . H481 . 122.5 no
C49 . C48 . H481 . 127.1 no
C45 . C49 . C48 . 106.78(18) yes
C45 . C49 . H491 . 127.1 no
C48 . C49 . H491 . 126.1 no
C46 . N50 . C51 . 114.50(16) yes
C43 . C51 . N50 . 123.03(19) yes
C43 . C51 . H511 . 119.1 no
N50 . C51 . H511 . 117.8 no
N12 . C52 . C53 . 109.60(15) yes
N12 . C52 . H521 . 107.3 no
C53 . C52 . H521 . 110.1 no
N12 . C52 . H522 . 109.4 no
C53 . C52 . H522 . 110.2 no
H521 . C52 . H522 . 110.2 no
C52 . C53 . N9 . 110.97(16) yes
C52 . C53 . H531 . 109.3 no
N9 . C53 . H531 . 107.9 no
C52 . C53 . H532 . 109.4 no
N9 . C53 . H532 . 110.4 no
H531 . C53 . H532 . 108.7 no
C7 . C54 . C55 . 114.95(16) yes
C7 . C54 . H542 . 107.6 no
C55 . C54 . H542 . 111.5 no
C7 . C54 . H541 . 107.1 no
C55 . C54 . H541 . 109.0 no
H542 . C54 . H541 . 106.2 no
C54 . C55 . C56 . 112.53(16) yes
C54 . C55 . H552 . 108.9 no
C56 . C55 . H552 . 107.3 no
C54 . C55 . H551 . 109.4 no
C56 . C55 . H551 . 109.6 no
H552 . C55 . H551 . 109.1 no
C55 . C56 . C57 . 107.95(16) yes
C55 . C56 . C58 . 110.22(17) yes
C57 . C56 . C58 . 109.09(17) yes
C55 . C56 . C59 . 110.85(17) yes
C57 . C56 . C59 . 109.50(16) yes
C58 . C56 . C59 . 109.20(18) yes
C56 . C57 . C6 . 114.09(16) yes
C56 . C57 . H571 . 108.2 no
C6 . C57 . H571 . 108.1 no
C56 . C57 . H572 . 109.8 no
C6 . C57 . H572 . 108.7 no
H571 . C57 . H572 . 107.8 no
C56 . C58 . H582 . 111.2 no
C56 . C58 . H583 . 110.3 no
H582 . C58 . H583 . 108.2 no
C56 . C58 . H581 . 110.8 no
H582 . C58 . H581 . 107.5 no
H583 . C58 . H581 . 108.6 no
C56 . C59 . H592 . 110.6 no
C56 . C59 . H593 . 109.4 no
H592 . C59 . H593 . 109.3 no
C56 . C59 . H591 . 110.8 no
H592 . C59 . H591 . 108.1 no
H593 . C59 . H591 . 108.5 no
C5 . C60 . C61 . 121.44(18) yes
C5 . C60 . H601 . 118.9 no
C61 . C60 . H601 . 119.7 no
C60 . C61 . C2 . 118.61(19) yes
C60 . C61 . H611 . 121.1 no
C2 . C61 . H611 . 120.3 no
N62 . C63 . C64 . 179.3(3) yes
C63 . C64 . H642 . 109.8 no
C63 . C64 . H641 . 108.9 no
H642 . C64 . H641 . 111.9 no
C63 . C64 . H643 . 106.6 no
H642 . C64 . H643 . 108.5 no
H641 . C64 . H643 . 111.0 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
N27 . H271 . O18 2_676 140.2(14) 0.855 2.237 2.945(3) yes
N27 . H271 . O39 . 130.5(14) 0.855 2.000 2.637(3) yes
C24 . H241 . N50 2_666 148 0.95 2.49 3.330(3) yes
N19 . H191 . O32 1_455 151(2) 0.846 2.151 2.918(3) yes
N47 . H471 . O22 2_666 160.7(20) 0.869 2.275 3.108(3) yes
C44 . H441 . O39 2_676 179 0.96 2.50 3.460(3) yes
C55 . H552 . O38 1_446 146 0.98 2.56 3.418(3) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
12 0 3 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_systematic        Venetoclax
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2377714'
loop_
_audit_author_name
_audit_author_address
'Eliska Zmeskalova'
;Institute of Physics of the Czech Academy of Sciences
Czech Republic
;
_audit_update_record             
;
2024-08-15 deposited with the CCDC.	2025-02-12 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
 ? 
;

#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   12.6958(5)
_cell_length_b                   43.0206(12)
_cell_length_c                   10.8969(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.267(5)
_cell_angle_gamma                90
_cell_volume                     5583.2(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

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'
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'
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'
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'


_cell_formula_units_Z            4

# Given Formula = C45 H55 Cl1 N7 O7 S1 
# Dc =      1.04 Fooo =   1852.00 Mu =     13.35 M =    873.49
# Found Formula = C55 H63 Cl1 N10 O11 S1 
# Dc =      1.32 FOOO =   2336.00 Mu =     15.24 M =   1107.68

_chemical_formula_sum            'C55 H63 Cl1 N10 O11 S1'
_chemical_formula_moiety         'C55 H63 Cl1 N10 O11 S1'
_chemical_compound_source        .
_chemical_formula_weight         1107.68


_cell_measurement_reflns_used    8139
_cell_measurement_theta_min      3.80
_cell_measurement_theta_max      73.19
_cell_measurement_temperature    95

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.037
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_max          0.125

_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2336
_exptl_absorpt_coefficient_mu    1.524

# Sheldrick geometric approximatio 0.89 0.95 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.95
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      95
_diffrn_reflns_number            34290
_diffrn_reflns_av_unetI/netI     0.105
_reflns_number_total             11044
_diffrn_reflns_av_R_equivalents  0.065
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 11044 
# Theoretical number of reflections is about 22519 


_diffrn_reflns_theta_min         3.711
_diffrn_reflns_theta_max         73.563
_diffrn_measured_fraction_theta_max 0.981

_diffrn_reflns_theta_full        69.149
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -53
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -15
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              53
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.16
_oxford_diffrn_Wilson_scale      0.19

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.69
_refine_diff_density_max         0.62


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     703
_refine_ls_number_reflns         11040
_oxford_refine_ls_R_factor_ref   0.0749
_refine_ls_R_factor_all          0.0749
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_all         0.1381
_refine_ls_goodness_of_fit_ref   0.9807
_refine_ls_shift/su_max          0.0006294
_refine_ls_shift/su_mean         0.0000566


# Computed with I/sigma = -10 
_oxford_reflns_number_all        11041
_oxford_refine_ls_R_factor_all   0.0750
_oxford_refine_ls_wR_factor_all  0.1382

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                8249
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_gt          0.1237


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 2.94P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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 1.59092(6) 0.388330(17) 1.67153(7) 0.0388 1.0000 Uani . . . . . .
C2 C 1.5910(2) 0.36984(6) 1.5289(3) 0.0307 1.0000 Uani . . . . . .
C3 C 1.5374(2) 0.34153(6) 1.4952(3) 0.0307 1.0000 Uani . . . . . .
C4 C 1.5412(2) 0.32643(6) 1.3849(3) 0.0277 1.0000 Uani . . . . . .
C5 C 1.5973(2) 0.33934(5) 1.3066(3) 0.0246 1.0000 Uani . . . . . .
C6 C 1.6084(2) 0.32141(5) 1.1948(3) 0.0244 1.0000 Uani . . . . . .
C7 C 1.5643(2) 0.32981(5) 1.0692(3) 0.0244 1.0000 Uani . . . . . .
C8 C 1.4907(2) 0.35817(5) 1.0242(3) 0.0231 1.0000 Uani . . . . . .
N9 N 1.36702(16) 0.35016(4) 0.9643(2) 0.0207 1.0000 Uani . . . . . .
C10 C 1.3034(2) 0.37810(5) 0.8953(3) 0.0214 1.0000 Uani . . . . . .
C11 C 1.1789(2) 0.37157(5) 0.8425(3) 0.0228 1.0000 Uani . . . . . .
N12 N 1.13930(17) 0.36271(4) 0.9490(2) 0.0241 1.0000 Uani . . . . . .
C13 C 1.04169(19) 0.37372(5) 0.9601(3) 0.0219 1.0000 Uani . . . . . .
C14 C 0.9858(2) 0.39959(5) 0.8868(3) 0.0221 1.0000 Uani . . . . . .
C15 C 0.8867(2) 0.41041(5) 0.8968(2) 0.0204 1.0000 Uani . . . . . .
O16 O 0.82928(14) 0.43498(4) 0.81939(19) 0.0257 1.0000 Uani . . . . . .
C17 C 0.8873(2) 0.45811(5) 0.7780(3) 0.0237 1.0000 Uani . . . . . .
C18 C 0.9147(2) 0.48537(5) 0.8486(3) 0.0245 1.0000 Uani . . . . . .
C19 C 0.9633(2) 0.50890(5) 0.7974(3) 0.0248 1.0000 Uani . . . . . .
C20 C 1.0033(2) 0.53980(6) 0.8323(3) 0.0280 1.0000 Uani . . . . . .
C21 C 1.0393(2) 0.55040(6) 0.7359(3) 0.0273 1.0000 Uani . . . . . .
N22 N 1.02308(18) 0.52815(5) 0.6405(2) 0.0263 1.0000 Uani . . . . . .
C23 C 0.9770(2) 0.50249(5) 0.6764(3) 0.0224 1.0000 Uani . . . . . .
N24 N 0.94836(17) 0.47631(4) 0.6066(2) 0.0232 1.0000 Uani . . . . . .
C25 C 0.9037(2) 0.45417(5) 0.6599(3) 0.0237 1.0000 Uani . . . . . .
C26 C 0.8381(2) 0.39723(5) 0.9829(2) 0.0211 1.0000 Uani . . . . . .
C27 C 0.73759(19) 0.40865(5) 1.0091(2) 0.0203 1.0000 Uani . . . . . .
O28 O 0.71209(15) 0.39961(4) 1.10087(18) 0.0267 1.0000 Uani . . . . . .
N29 N 0.67303(17) 0.43071(4) 0.9226(2) 0.0226 1.0000 Uani . . . . . .
S30 S 0.57072(5) 0.451268(12) 0.94344(6) 0.0215 1.0000 Uani . . . . . .
O31 O 0.48359(14) 0.43112(4) 0.95061(18) 0.0263 1.0000 Uani . . . . . .
O32 O 0.54726(14) 0.47385(4) 0.84115(18) 0.0255 1.0000 Uani . . . . . .
C33 C 0.6292(2) 0.46987(5) 1.0941(3) 0.0233 1.0000 Uani . . . . . .
C34 C 0.6106(2) 0.45878(5) 1.2063(3) 0.0233 1.0000 Uani . . . . . .
C35 C 0.6468(2) 0.47578(5) 1.3193(3) 0.0243 1.0000 Uani . . . . . .
C36 C 0.7024(2) 0.50486(5) 1.3278(3) 0.0237 1.0000 Uani . . . . . .
N37 N 0.72698(18) 0.52248(5) 1.4354(2) 0.0270 1.0000 Uani . . . . . .
C38 C 0.6835(2) 0.51680(6) 1.5406(3) 0.0271 1.0000 Uani . . . . . .
C39 C 0.7075(2) 0.54436(6) 1.6334(3) 0.0279 1.0000 Uani . . . . . .
C40 C 0.6502(3) 0.57431(6) 1.5682(3) 0.0396 1.0000 Uani . . . . . .
C41 C 0.6690(3) 0.59972(6) 1.6716(3) 0.0483 1.0000 Uani . . . . . .
O42 O 0.62611(19) 0.59119(5) 1.7705(2) 0.0458 1.0000 Uani . . . . . .
C43 C 0.6840(3) 0.56473(7) 1.8394(3) 0.0379 1.0000 Uani . . . . . .
C44 C 0.6699(2) 0.53686(6) 1.7491(3) 0.0322 1.0000 Uani . . . . . .
C45 C 0.7292(2) 0.51351(5) 1.2159(3) 0.0241 1.0000 Uani . . . . . .
C46 C 0.6913(2) 0.49663(5) 1.1011(3) 0.0226 1.0000 Uani . . . . . .
N47 N 0.79155(18) 0.54156(5) 1.2141(2) 0.0279 1.0000 Uani . . . . . .
O48 O 0.81278(17) 0.56026(4) 1.3061(2) 0.0345 1.0000 Uani . . . . . .
O49 O 0.82358(16) 0.54596(4) 1.1211(2) 0.0353 1.0000 Uani . . . . . .
C50 C 0.8960(2) 0.37180(5) 1.0563(3) 0.0252 1.0000 Uani . . . . . .
C51 C 0.9932(2) 0.36002(5) 1.0460(3) 0.0267 1.0000 Uani . . . . . .
C52 C 1.1956(2) 0.33421(5) 1.0121(3) 0.0241 1.0000 Uani . . . . . .
C53 C 1.3218(2) 0.33908(5) 1.0672(3) 0.0222 1.0000 Uani . . . . . .
C54 C 1.5845(2) 0.31173(6) 0.9604(3) 0.0334 1.0000 Uani . . . . . .
C55 C 1.6774(2) 0.28741(7) 1.0107(3) 0.0358 1.0000 Uani . . . . . .
C56 C 1.6671(2) 0.26903(6) 1.1262(3) 0.0329 1.0000 Uani . . . . . .
C57 C 1.6796(2) 0.29224(6) 1.2368(3) 0.0290 1.0000 Uani . . . . . .
C58 C 1.5537(3) 0.25252(7) 1.0892(4) 0.0435 1.0000 Uani . . . . . .
C59 C 1.7609(3) 0.24480(7) 1.1707(4) 0.0434 1.0000 Uani . . . . . .
C60 C 1.6499(2) 0.36818(6) 1.3432(3) 0.0289 1.0000 Uani . . . . . .
C61 C 1.6458(2) 0.38344(6) 1.4533(3) 0.0317 1.0000 Uani . . . . . .
O62 O 1.26743(16) 0.25714(4) 0.88328(18) 0.0284 1.0000 Uani . . . . . .
C63 C 1.2868(2) 0.22903(6) 0.8468(3) 0.0256 1.0000 Uani . . . . . .
O64 O 1.30329(17) 0.22339(4) 0.74585(19) 0.0329 1.0000 Uani . . . . . .
C65 C 1.2904(2) 0.20447(5) 0.9444(3) 0.0252 1.0000 Uani . . . . . .
C66 C 1.3017(2) 0.21025(5) 1.0672(3) 0.0235 1.0000 Uani . . . . . .
C67 C 1.3140(2) 0.18486(5) 1.1667(3) 0.0242 1.0000 Uani . . . . . .
O68 O 1.31209(15) 0.19400(4) 1.27792(18) 0.0259 1.0000 Uani . . . . . .
O69 O 1.32640(18) 0.15761(4) 1.1388(2) 0.0353 1.0000 Uani . . . . . .
N70 N 1.0158(3) 0.29022(7) 1.1987(4) 0.0614 1.0000 Uani . . . . . .
C71 C 1.0295(3) 0.27371(8) 1.1229(4) 0.0495 1.0000 Uani . . . . . .
C72 C 1.0452(3) 0.25295(9) 1.0241(5) 0.0646 1.0000 Uani . . . . . .
N73 N 0.9378(3) 0.39070(7) 0.4950(4) 0.0602 1.0000 Uani . . . . . .
C74 C 0.9948(3) 0.37454(8) 0.4684(3) 0.0487 1.0000 Uani . . . . . .
C75 C 1.0671(5) 0.35240(15) 0.4345(6) 0.1180 1.0000 Uani . . . . . .
N76 N 1.0075(3) 0.30517(8) 0.7185(4) 0.0781 1.0000 Uani . . . . . .
C77 C 0.9316(3) 0.31898(7) 0.7108(4) 0.0544 1.0000 Uani . . . . . .
C78 C 0.8324(3) 0.33700(8) 0.6974(5) 0.0757 1.0000 Uani . . . . . .
H31 H 1.4982 0.3331 1.5457 0.0368 1.0000 Uiso R . . . . .
H41 H 1.5045 0.3072 1.3607 0.0342 1.0000 Uiso R . . . . .
H82 H 1.4998 0.3720 1.0998 0.0283 1.0000 Uiso R . . . . .
H81 H 1.5119 0.3690 0.9569 0.0276 1.0000 Uiso R . . . . .
H101 H 1.3205 0.3950 0.9572 0.0252 1.0000 Uiso R . . . . .
H102 H 1.3296 0.3830 0.8240 0.0253 1.0000 Uiso R . . . . .
H111 H 1.1399 0.3901 0.7976 0.0267 1.0000 Uiso R . . . . .
H112 H 1.1640 0.3545 0.7788 0.0270 1.0000 Uiso R . . . . .
H141 H 1.0178 0.4096 0.8307 0.0278 1.0000 Uiso R . . . . .
H181 H 0.9020 0.4877 0.9275 0.0301 1.0000 Uiso R . . . . .
H201 H 1.0053 0.5506 0.9071 0.0336 1.0000 Uiso R . . . . .
H211 H 1.0712 0.5701 0.7323 0.0321 1.0000 Uiso R . . . . .
H251 H 0.8819 0.4351 0.6125 0.0290 1.0000 Uiso R . . . . .
H341 H 0.5724 0.4399 1.2028 0.0275 1.0000 Uiso R . . . . .
H351 H 0.6342 0.4678 1.3935 0.0295 1.0000 Uiso R . . . . .
H382 H 0.7181 0.4983 1.5912 0.0325 1.0000 Uiso R . . . . .
H381 H 0.6018 0.5137 1.5008 0.0325 1.0000 Uiso R . . . . .
H391 H 0.7879 0.5479 1.6641 0.0328 1.0000 Uiso R . . . . .
H402 H 0.6817 0.5808 1.5048 0.0469 1.0000 Uiso R . . . . .
H401 H 0.5691 0.5708 1.5245 0.0478 1.0000 Uiso R . . . . .
H411 H 0.6308 0.6179 1.6290 0.0577 1.0000 Uiso R . . . . .
H412 H 0.7500 0.6047 1.7092 0.0567 1.0000 Uiso R . . . . .
H432 H 0.7651 0.5702 1.8785 0.0452 1.0000 Uiso R . . . . .
H431 H 0.6556 0.5600 1.9112 0.0464 1.0000 Uiso R . . . . .
H441 H 0.7141 0.5191 1.7984 0.0392 1.0000 Uiso R . . . . .
H442 H 0.5892 0.5312 1.7163 0.0393 1.0000 Uiso R . . . . .
H461 H 0.7054 0.5031 1.0268 0.0269 1.0000 Uiso R . . . . .
H501 H 0.8662 0.3626 1.1144 0.0297 1.0000 Uiso R . . . . .
H511 H 1.0265 0.3426 1.0965 0.0320 1.0000 Uiso R . . . . .
H522 H 1.1713 0.3288 1.0857 0.0296 1.0000 Uiso R . . . . .
H521 H 1.1773 0.3172 0.9504 0.0286 1.0000 Uiso R . . . . .
H532 H 1.3425 0.3546 1.1374 0.0262 1.0000 Uiso R . . . . .
H531 H 1.3570 0.3199 1.1003 0.0262 1.0000 Uiso R . . . . .
H541 H 1.6058 0.3268 0.9036 0.0402 1.0000 Uiso R . . . . .
H542 H 1.5143 0.3018 0.9070 0.0402 1.0000 Uiso R . . . . .
H552 H 1.7502 0.2981 1.0383 0.0431 1.0000 Uiso R . . . . .
H551 H 1.6745 0.2734 0.9391 0.0429 1.0000 Uiso R . . . . .
H571 H 1.7576 0.2985 1.2724 0.0350 1.0000 Uiso R . . . . .
H572 H 1.6597 0.2817 1.3057 0.0349 1.0000 Uiso R . . . . .
H582 H 1.5520 0.2393 1.1620 0.0649 1.0000 Uiso R . . . . .
H581 H 1.4926 0.2677 1.0680 0.0645 1.0000 Uiso R . . . . .
H583 H 1.5445 0.2395 1.0137 0.0645 1.0000 Uiso R . . . . .
H592 H 1.7552 0.2330 1.2445 0.0648 1.0000 Uiso R . . . . .
H591 H 1.8341 0.2549 1.1940 0.0642 1.0000 Uiso R . . . . .
H593 H 1.7513 0.2304 1.0989 0.0649 1.0000 Uiso R . . . . .
H601 H 1.6886 0.3769 1.2918 0.0344 1.0000 Uiso R . . . . .
H611 H 1.6816 0.4027 1.4773 0.0386 1.0000 Uiso R . . . . .
H651 H 1.2884 0.1837 0.9171 0.0304 1.0000 Uiso R . . . . .
H661 H 1.3028 0.2307 1.0940 0.0277 1.0000 Uiso R . . . . .
H722 H 1.0618 0.2325 1.0594 0.0978 1.0000 Uiso R . . . . .
H721 H 1.1054 0.2601 0.9972 0.0978 1.0000 Uiso R . . . . .
H723 H 0.9795 0.2521 0.9478 0.0980 1.0000 Uiso R . . . . .
H751 H 1.0856 0.3603 0.3631 0.1772 1.0000 Uiso R . . . . .
H753 H 1.1358 0.3495 0.5056 0.1767 1.0000 Uiso R . . . . .
H752 H 1.0293 0.3330 0.4088 0.1770 1.0000 Uiso R . . . . .
H781 H 0.8124 0.3342 0.7762 0.1122 1.0000 Uiso R . . . . .
H783 H 0.8460 0.3587 0.6865 0.1132 1.0000 Uiso R . . . . .
H782 H 0.7694 0.3297 0.6236 0.1130 1.0000 Uiso R . . . . .
H621 H 1.2809 0.2711 0.8367 0.0426 1.0000 Uiso R . . . . .
H291 H 0.6984 0.4373 0.8644 0.0277 1.0000 Uiso R . . . . .
H221 H 1.0434 0.5297 0.5732 0.0320 1.0000 Uiso R . . . . .
H371 H 0.7602 0.5398 1.4342 0.0336 1.0000 Uiso R . . . . .
H91 H 1.3558 0.3350 0.9005 0.0331 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.104(12)
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 . 1.746(3) yes
C2 . C3 . 1.382(4) yes
C2 . C61 . 1.379(4) yes
C3 . C4 . 1.382(4) yes
C3 . H31 . 0.933 no
C4 . C5 . 1.402(3) yes
C4 . H41 . 0.939 no
C5 . C6 . 1.489(4) yes
C5 . C60 . 1.400(3) yes
C6 . C7 . 1.337(4) yes
C6 . C57 . 1.522(3) yes
C7 . C8 . 1.512(3) yes
C7 . C54 . 1.512(4) yes
C8 . N9 . 1.516(3) yes
C8 . H82 . 0.991 no
C8 . H81 . 0.981 no
N9 . C10 . 1.497(3) yes
N9 . C53 . 1.502(3) yes
N9 . H91 . 0.929 no
C10 . C11 . 1.509(3) yes
C10 . H101 . 0.965 no
C10 . H102 . 0.969 no
C11 . N12 . 1.466(3) yes
C11 . H111 . 0.974 no
C11 . H112 . 0.981 no
N12 . C13 . 1.371(3) yes
N12 . C52 . 1.465(3) yes
C13 . C14 . 1.409(3) yes
C13 . C51 . 1.415(3) yes
C14 . C15 . 1.381(3) yes
C14 . H141 . 0.946 no
C15 . O16 . 1.391(3) yes
C15 . C26 . 1.408(3) yes
O16 . C17 . 1.402(3) yes
C17 . C18 . 1.379(4) yes
C17 . C25 . 1.383(4) yes
C18 . C19 . 1.398(3) yes
C18 . H181 . 0.933 no
C19 . C20 . 1.427(3) yes
C19 . C23 . 1.415(4) yes
C20 . C21 . 1.361(4) yes
C20 . H201 . 0.931 no
C21 . N22 . 1.375(3) yes
C21 . H211 . 0.946 no
N22 . C23 . 1.368(3) yes
N22 . H221 . 0.860 no
C23 . N24 . 1.337(3) yes
N24 . C25 . 1.340(3) yes
C25 . H251 . 0.959 no
C26 . C27 . 1.485(3) yes
C26 . C50 . 1.403(3) yes
C27 . O28 . 1.217(3) yes
C27 . N29 . 1.387(3) yes
N29 . S30 . 1.6506(19) yes
N29 . H291 . 0.854 no
S30 . O31 . 1.4287(17) yes
S30 . O32 . 1.4299(18) yes
S30 . C33 . 1.744(3) yes
C33 . C34 . 1.407(3) yes
C33 . C46 . 1.382(3) yes
C34 . C35 . 1.367(4) yes
C34 . H341 . 0.939 no
C35 . C36 . 1.424(3) yes
C35 . H351 . 0.943 no
C36 . N37 . 1.339(3) yes
C36 . C45 . 1.424(4) yes
N37 . C38 . 1.456(3) yes
N37 . H371 . 0.860 no
C38 . C39 . 1.519(3) yes
C38 . H382 . 0.982 no
C38 . H381 . 0.985 no
C39 . C40 . 1.529(4) yes
C39 . C44 . 1.530(4) yes
C39 . H391 . 0.970 no
C40 . C41 . 1.528(4) yes
C40 . H402 . 0.952 no
C40 . H401 . 0.985 no
C41 . O42 . 1.414(4) yes
C41 . H411 . 0.953 no
C41 . H412 . 0.989 no
O42 . C43 . 1.420(4) yes
C43 . C44 . 1.522(4) yes
C43 . H432 . 0.996 no
C43 . H431 . 0.989 no
C44 . H441 . 0.988 no
C44 . H442 . 0.991 no
C45 . C46 . 1.380(4) yes
C45 . N47 . 1.447(3) yes
C46 . H461 . 0.931 no
N47 . O48 . 1.240(3) yes
N47 . O49 . 1.231(3) yes
C50 . C51 . 1.373(3) yes
C50 . H501 . 0.932 no
C51 . H511 . 0.940 no
C52 . C53 . 1.518(3) yes
C52 . H522 . 0.981 no
C52 . H521 . 0.967 no
C53 . H532 . 0.981 no
C53 . H531 . 0.947 no
C54 . C55 . 1.530(4) yes
C54 . H541 . 0.996 no
C54 . H542 . 0.976 no
C55 . C56 . 1.530(4) yes
C55 . H552 . 0.980 no
C55 . H551 . 0.977 no
C56 . C57 . 1.531(4) yes
C56 . C58 . 1.530(4) yes
C56 . C59 . 1.530(4) yes
C57 . H571 . 0.968 no
C57 . H572 . 0.982 no
C58 . H582 . 0.982 no
C58 . H581 . 0.979 no
C58 . H583 . 0.970 no
C59 . H592 . 0.974 no
C59 . H591 . 0.976 no
C59 . H593 . 0.972 no
C60 . C61 . 1.384(4) yes
C60 . H601 . 0.943 no
C61 . H611 . 0.936 no
O62 . C63 . 1.323(3) yes
O62 . H621 . 0.842 no
C63 . O64 . 1.213(3) yes
C63 . C65 . 1.488(3) yes
C65 . C66 . 1.320(4) yes
C65 . H651 . 0.939 no
C66 . C67 . 1.508(3) yes
C66 . H661 . 0.926 no
C67 . O68 . 1.282(3) yes
C67 . O69 . 1.235(3) yes
N70 . C71 . 1.148(5) yes
C71 . C72 . 1.465(6) yes
C72 . H722 . 0.956 no
C72 . H721 . 0.960 no
C72 . H723 . 0.952 no
N73 . C74 . 1.112(4) yes
C74 . C75 . 1.456(5) yes
C75 . H751 . 0.950 no
C75 . H753 . 0.953 no
C75 . H752 . 0.955 no
N76 . C77 . 1.110(5) yes
C77 . C78 . 1.442(5) yes
C78 . H781 . 0.984 no
C78 . H783 . 0.963 no
C78 . H782 . 0.970 no
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 . 119.1(2) yes
Cl1 . C2 . C61 . 119.6(2) yes
C3 . C2 . C61 . 121.3(3) yes
C2 . C3 . C4 . 118.9(2) yes
C2 . C3 . H31 . 119.9 no
C4 . C3 . H31 . 121.2 no
C3 . C4 . C5 . 121.4(2) yes
C3 . C4 . H41 . 119.6 no
C5 . C4 . H41 . 119.0 no
C4 . C5 . C6 . 120.3(2) yes
C4 . C5 . C60 . 118.0(2) yes
C6 . C5 . C60 . 121.4(2) yes
C5 . C6 . C7 . 125.0(2) yes
C5 . C6 . C57 . 113.3(2) yes
C7 . C6 . C57 . 121.7(2) yes
C6 . C7 . C8 . 122.9(2) yes
C6 . C7 . C54 . 122.6(2) yes
C8 . C7 . C54 . 114.5(2) yes
C7 . C8 . N9 . 112.81(19) yes
C7 . C8 . H82 . 109.6 no
N9 . C8 . H82 . 107.4 no
C7 . C8 . H81 . 109.0 no
N9 . C8 . H81 . 107.3 no
H82 . C8 . H81 . 110.7 no
C8 . N9 . C10 . 109.35(17) yes
C8 . N9 . C53 . 110.94(19) yes
C10 . N9 . C53 . 110.51(17) yes
C8 . N9 . H91 . 110.4 no
C10 . N9 . H91 . 105.8 no
C53 . N9 . H91 . 109.7 no
N9 . C10 . C11 . 110.70(18) yes
N9 . C10 . H101 . 107.7 no
C11 . C10 . H101 . 111.0 no
N9 . C10 . H102 . 107.7 no
C11 . C10 . H102 . 109.9 no
H101 . C10 . H102 . 109.8 no
C10 . C11 . N12 . 110.3(2) yes
C10 . C11 . H111 . 108.8 no
N12 . C11 . H111 . 110.9 no
C10 . C11 . H112 . 109.2 no
N12 . C11 . H112 . 109.3 no
H111 . C11 . H112 . 108.3 no
C11 . N12 . C13 . 123.3(2) yes
C11 . N12 . C52 . 110.11(18) yes
C13 . N12 . C52 . 123.83(19) yes
N12 . C13 . C14 . 121.0(2) yes
N12 . C13 . C51 . 121.9(2) yes
C14 . C13 . C51 . 117.1(2) yes
C13 . C14 . C15 . 121.0(2) yes
C13 . C14 . H141 . 118.7 no
C15 . C14 . H141 . 120.3 no
C14 . C15 . O16 . 120.6(2) yes
C14 . C15 . C26 . 122.6(2) yes
O16 . C15 . C26 . 116.8(2) yes
C15 . O16 . C17 . 120.74(18) yes
O16 . C17 . C18 . 118.9(2) yes
O16 . C17 . C25 . 118.5(2) yes
C18 . C17 . C25 . 122.2(2) yes
C17 . C18 . C19 . 117.0(2) yes
C17 . C18 . H181 . 121.0 no
C19 . C18 . H181 . 122.0 no
C18 . C19 . C20 . 137.2(3) yes
C18 . C19 . C23 . 116.4(2) yes
C20 . C19 . C23 . 106.4(2) yes
C19 . C20 . C21 . 106.8(2) yes
C19 . C20 . H201 . 126.7 no
C21 . C20 . H201 . 126.5 no
C20 . C21 . N22 . 110.4(2) yes
C20 . C21 . H211 . 126.5 no
N22 . C21 . H211 . 123.1 no
C21 . N22 . C23 . 108.2(2) yes
C21 . N22 . H221 . 125.5 no
C23 . N22 . H221 . 126.1 no
C19 . C23 . N22 . 108.2(2) yes
C19 . C23 . N24 . 126.7(2) yes
N22 . C23 . N24 . 125.2(2) yes
C23 . N24 . C25 . 115.1(2) yes
C17 . C25 . N24 . 122.6(2) yes
C17 . C25 . H251 . 119.9 no
N24 . C25 . H251 . 117.5 no
C15 . C26 . C27 . 126.8(2) yes
C15 . C26 . C50 . 115.4(2) yes
C27 . C26 . C50 . 117.6(2) yes
C26 . C27 . O28 . 122.9(2) yes
C26 . C27 . N29 . 116.2(2) yes
O28 . C27 . N29 . 120.9(2) yes
C27 . N29 . S30 . 125.54(17) yes
C27 . N29 . H291 . 116.4 no
S30 . N29 . H291 . 116.3 no
N29 . S30 . O31 . 110.09(10) yes
N29 . S30 . O32 . 102.61(10) yes
O31 . S30 . O32 . 119.91(11) yes
N29 . S30 . C33 . 106.04(11) yes
O31 . S30 . C33 . 108.19(11) yes
O32 . S30 . C33 . 109.14(11) yes
S30 . C33 . C34 . 121.17(18) yes
S30 . C33 . C46 . 118.9(2) yes
C34 . C33 . C46 . 119.9(2) yes
C33 . C34 . C35 . 119.7(2) yes
C33 . C34 . H341 . 119.8 no
C35 . C34 . H341 . 120.4 no
C34 . C35 . C36 . 122.2(2) yes
C34 . C35 . H351 . 118.2 no
C36 . C35 . H351 . 119.6 no
C35 . C36 . N37 . 121.0(2) yes
C35 . C36 . C45 . 115.7(2) yes
N37 . C36 . C45 . 123.3(2) yes
C36 . N37 . C38 . 123.9(2) yes
C36 . N37 . H371 . 116.5 no
C38 . N37 . H371 . 118.6 no
N37 . C38 . C39 . 110.5(2) yes
N37 . C38 . H382 . 111.2 no
C39 . C38 . H382 . 108.2 no
N37 . C38 . H381 . 107.7 no
C39 . C38 . H381 . 109.7 no
H382 . C38 . H381 . 109.7 no
C38 . C39 . C40 . 113.3(2) yes
C38 . C39 . C44 . 109.6(2) yes
C40 . C39 . C44 . 109.0(2) yes
C38 . C39 . H391 . 107.3 no
C40 . C39 . H391 . 107.7 no
C44 . C39 . H391 . 109.9 no
C39 . C40 . C41 . 109.5(2) yes
C39 . C40 . H402 . 109.3 no
C41 . C40 . H402 . 109.1 no
C39 . C40 . H401 . 110.2 no
C41 . C40 . H401 . 109.7 no
H402 . C40 . H401 . 109.0 no
C40 . C41 . O42 . 111.9(3) yes
C40 . C41 . H411 . 107.8 no
O42 . C41 . H411 . 108.6 no
C40 . C41 . H412 . 109.5 no
O42 . C41 . H412 . 111.1 no
H411 . C41 . H412 . 107.8 no
C41 . O42 . C43 . 110.2(2) yes
O42 . C43 . C44 . 111.5(3) yes
O42 . C43 . H432 . 107.9 no
C44 . C43 . H432 . 109.5 no
O42 . C43 . H431 . 108.7 no
C44 . C43 . H431 . 110.8 no
H432 . C43 . H431 . 108.4 no
C39 . C44 . C43 . 111.5(2) yes
C39 . C44 . H441 . 109.3 no
C43 . C44 . H441 . 109.8 no
C39 . C44 . H442 . 109.5 no
C43 . C44 . H442 . 107.5 no
H441 . C44 . H442 . 109.2 no
C36 . C45 . C46 . 121.8(2) yes
C36 . C45 . N47 . 121.5(2) yes
C46 . C45 . N47 . 116.6(2) yes
C33 . C46 . C45 . 120.1(2) yes
C33 . C46 . H461 . 118.6 no
C45 . C46 . H461 . 121.2 no
C45 . N47 . O48 . 119.8(2) yes
C45 . N47 . O49 . 118.5(2) yes
O48 . N47 . O49 . 121.7(2) yes
C26 . C50 . C51 . 123.3(2) yes
C26 . C50 . H501 . 117.6 no
C51 . C50 . H501 . 119.0 no
C13 . C51 . C50 . 120.6(2) yes
C13 . C51 . H511 . 120.6 no
C50 . C51 . H511 . 118.8 no
N12 . C52 . C53 . 110.28(19) yes
N12 . C52 . H522 . 109.9 no
C53 . C52 . H522 . 107.3 no
N12 . C52 . H521 . 110.3 no
C53 . C52 . H521 . 110.2 no
H522 . C52 . H521 . 108.8 no
C52 . C53 . N9 . 111.9(2) yes
C52 . C53 . H532 . 111.3 no
N9 . C53 . H532 . 107.3 no
C52 . C53 . H531 . 108.9 no
N9 . C53 . H531 . 108.0 no
H532 . C53 . H531 . 109.4 no
C7 . C54 . C55 . 113.0(2) yes
C7 . C54 . H541 . 108.0 no
C55 . C54 . H541 . 109.0 no
C7 . C54 . H542 . 108.9 no
C55 . C54 . H542 . 110.3 no
H541 . C54 . H542 . 107.6 no
C54 . C55 . C56 . 111.9(2) yes
C54 . C55 . H552 . 108.6 no
C56 . C55 . H552 . 109.2 no
C54 . C55 . H551 . 109.0 no
C56 . C55 . H551 . 110.3 no
H552 . C55 . H551 . 107.8 no
C55 . C56 . C57 . 107.2(2) yes
C55 . C56 . C58 . 111.4(3) yes
C57 . C56 . C58 . 110.0(2) yes
C55 . C56 . C59 . 109.5(2) yes
C57 . C56 . C59 . 109.7(3) yes
C58 . C56 . C59 . 109.0(2) yes
C56 . C57 . C6 . 114.3(2) yes
C56 . C57 . H571 . 107.9 no
C6 . C57 . H571 . 108.1 no
C56 . C57 . H572 . 108.5 no
C6 . C57 . H572 . 109.2 no
H571 . C57 . H572 . 108.7 no
C56 . C58 . H582 . 109.7 no
C56 . C58 . H581 . 110.4 no
H582 . C58 . H581 . 109.9 no
C56 . C58 . H583 . 108.5 no
H582 . C58 . H583 . 108.7 no
H581 . C58 . H583 . 109.5 no
C56 . C59 . H592 . 110.1 no
C56 . C59 . H591 . 110.2 no
H592 . C59 . H591 . 110.7 no
C56 . C59 . H593 . 108.2 no
H592 . C59 . H593 . 107.9 no
H591 . C59 . H593 . 109.6 no
C5 . C60 . C61 . 120.7(2) yes
C5 . C60 . H601 . 118.7 no
C61 . C60 . H601 . 120.6 no
C60 . C61 . C2 . 119.7(2) yes
C60 . C61 . H611 . 120.0 no
C2 . C61 . H611 . 120.3 no
C63 . O62 . H621 . 112.0 no
O62 . C63 . O64 . 124.3(2) yes
O62 . C63 . C65 . 113.4(2) yes
O64 . C63 . C65 . 122.2(2) yes
C63 . C65 . C66 . 123.8(2) yes
C63 . C65 . H651 . 117.3 no
C66 . C65 . H651 . 118.8 no
C65 . C66 . C67 . 122.7(2) yes
C65 . C66 . H661 . 118.9 no
C67 . C66 . H661 . 118.4 no
C66 . C67 . O68 . 115.2(2) yes
C66 . C67 . O69 . 120.0(2) yes
O68 . C67 . O69 . 124.7(2) yes
N70 . C71 . C72 . 178.8(4) yes
C71 . C72 . H722 . 109.5 no
C71 . C72 . H721 . 110.7 no
H722 . C72 . H721 . 109.3 no
C71 . C72 . H723 . 111.4 no
H722 . C72 . H723 . 108.6 no
H721 . C72 . H723 . 107.2 no
N73 . C74 . C75 . 177.9(5) yes
C74 . C75 . H751 . 109.4 no
C74 . C75 . H753 . 111.1 no
H751 . C75 . H753 . 107.3 no
C74 . C75 . H752 . 110.4 no
H751 . C75 . H752 . 108.2 no
H753 . C75 . H752 . 110.4 no
N76 . C77 . C78 . 178.6(5) yes
C77 . C78 . H781 . 109.1 no
C77 . C78 . H783 . 110.3 no
H781 . C78 . H783 . 109.7 no
C77 . C78 . H782 . 110.5 no
H781 . C78 . H782 . 107.2 no
H783 . C78 . H782 . 110.1 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
C11 . H111 . O48 2_767 138 0.97 2.58 3.370(4) yes
C25 . H251 . N73 . 147 0.96 2.53 3.378(4) yes
C51 . H511 . N70 . 152 0.94 2.54 3.397(4) yes
C53 . H532 . O42 2_768 155 0.98 2.51 3.429(4) yes
C54 . H542 . O68 3_554 149 0.98 2.47 3.348(4) yes
C60 . H601 . O28 1_655 157 0.94 2.41 3.297(4) yes
C66 . H661 . O64 3_555 158 0.93 2.57 3.451(4) yes
C75 . H753 . O69 3_554 165 0.95 2.37 3.302(4) yes
O62 . H621 . O68 3_554 164 0.84 1.73 2.551(4) yes
N29 . H291 . O16 . 140 0.85 1.89 2.604(4) yes
N22 . H221 . N24 2_766 162 0.86 2.01 2.845(4) yes
N37 . H371 . O48 . 134 0.86 1.95 2.622(4) yes
N9 . H91 . C67 3_554 155 0.93 2.56 3.425(4) yes
N9 . H91 . O68 3_554 171 0.93 1.77 2.691(4) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-3 6 13 x .
3 1 10 x .
0 10 3 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_systematic        Venetoclax
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2377712'
loop_
_audit_author_name
_audit_author_address
'Eliska Zmeskalova'
;Institute of Physics of the Czech Academy of Sciences
Czech Republic
;
_audit_update_record             
;
2024-08-15 deposited with the CCDC.	2025-02-12 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
 ? 
;

#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   11.1533(4)
_cell_length_b                   12.6185(5)
_cell_length_c                   19.2633(7)
_cell_angle_alpha                71.723(3)
_cell_angle_beta                 85.508(3)
_cell_angle_gamma                73.590(3)
_cell_volume                     2469.28(17)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

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 0.0033 0.0016 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 0.0106 0.0060 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'
N 0.0061 0.0033 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'
S 0.1246 0.1234 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'
Cl 0.1484 0.1585 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'


_cell_formula_units_Z            2

# Given Formula = C0.50 H0.50 Cl0.50 N0.50 O0.50 S0.50 
# Dc =      0.07 Fooo =     55.00 Mu =      0.52 M =     55.27
# Found Formula = C49 H55 Cl1 N8 O11 S1 
# Dc =      1.34 FOOO =   1052.00 Mu =      1.88 M =    999.54

_chemical_formula_sum            'C49 H55 Cl1 N8 O11 S1'
_chemical_formula_moiety         'C49 H55 Cl1 N8 O11 S1'
_chemical_compound_source        .
_chemical_formula_weight         999.54


_cell_measurement_reflns_used    8218
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      28.62
_cell_measurement_temperature    120

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.143
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_max          0.485

_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1052
_exptl_absorpt_coefficient_mu    0.188

# Sheldrick geometric approximatio 0.96 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      120
_diffrn_reflns_number            18873
_diffrn_reflns_av_unetI/netI     0.052
_reflns_number_total             11173
_diffrn_reflns_av_R_equivalents  0.029
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 11173 
# Theoretical number of reflections is about 25635 


_diffrn_reflns_theta_min         2.358
_diffrn_reflns_theta_max         28.745
_diffrn_measured_fraction_theta_max 0.872

_diffrn_reflns_theta_full        26.167
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -14
_reflns_limit_h_max              15
_reflns_limit_k_min              -15
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_oxford_diffrn_Wilson_B_factor   2.25
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.73
_refine_diff_density_max         1.56


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     19
_refine_ls_number_parameters     651
_refine_ls_number_reflns         11173
_oxford_refine_ls_R_factor_ref   0.0840
_refine_ls_R_factor_all          0.0840
_refine_ls_wR_factor_ref         0.1648
_refine_ls_wR_factor_all         0.1648
_refine_ls_goodness_of_fit_ref   0.9906
_refine_ls_shift/su_max          0.0004229
_refine_ls_shift/su_mean         0.0000391


# Computed with I/sigma = -10 
_oxford_reflns_number_all        11173
_oxford_refine_ls_R_factor_all   0.0840
_oxford_refine_ls_wR_factor_all  0.1648

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7533
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_gt          0.1449


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.10P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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 1.07795(6) 0.46542(6) 0.34353(3) 0.0290 1.0000 Uani . . . . . .
C2 C 0.9892(2) 0.5034(2) 0.26399(13) 0.0219 1.0000 Uani . . . . . .
C3 C 1.0011(2) 0.5963(2) 0.20544(13) 0.0216 1.0000 Uani . . . . . .
C4 C 0.9246(2) 0.6296(2) 0.14491(13) 0.0217 1.0000 Uani . . . . . .
C5 C 0.8384(2) 0.5708(2) 0.14177(13) 0.0207 1.0000 Uani . . . . . .
C6 C 0.7575(2) 0.6073(2) 0.07513(13) 0.0216 1.0000 Uani . . . . . .
C7 C 0.6332(2) 0.6507(2) 0.07528(13) 0.0207 1.0000 Uani . . . . . .
C8 C 0.5633(2) 0.6677(2) 0.14221(13) 0.0217 1.0000 Uani D . . . . .
N9 N 0.51445(17) 0.79540(16) 0.13762(10) 0.0170 1.0000 Uani D . . . . .
C10 C 0.4563(2) 0.8043(2) 0.20905(12) 0.0203 1.0000 Uani D . . . . .
C11 C 0.4095(2) 0.9293(2) 0.20878(13) 0.0209 1.0000 Uani . . . . . .
N12 N 0.51155(18) 0.98422(17) 0.19285(11) 0.0201 1.0000 Uani . . . . . .
C13 C 0.5075(2) 1.0768(2) 0.21769(12) 0.0177 1.0000 Uani . . . . . .
C14 C 0.4117(2) 1.1145(2) 0.26338(12) 0.0180 1.0000 Uani . . . . . .
C15 C 0.4072(2) 1.2087(2) 0.28588(12) 0.0168 1.0000 Uani . . . . . .
O16 O 0.30637(15) 1.24888(14) 0.32656(9) 0.0227 1.0000 Uani . . . . . .
C17 C 0.2687(2) 1.1673(2) 0.38587(13) 0.0206 1.0000 Uani . . . . . .
C18 C 0.1523(2) 1.1499(2) 0.38012(13) 0.0214 1.0000 Uani . . . . . .
N19 N 0.10284(18) 1.08086(18) 0.43511(11) 0.0209 1.0000 Uani . . . . . .
C20 C 0.1740(2) 1.0271(2) 0.49512(13) 0.0195 1.0000 Uani D . . . . .
N21 N 0.14310(19) 0.95131(19) 0.55733(11) 0.0234 1.0000 Uani D . . . . .
C22 C 0.2379(2) 0.9162(2) 0.60727(13) 0.0257 1.0000 Uani D . . . . .
C23 C 0.3313(2) 0.9672(2) 0.57938(14) 0.0258 1.0000 Uani . . . . . .
C24 C 0.2927(2) 1.0394(2) 0.50667(13) 0.0214 1.0000 Uani . . . . . .
C25 C 0.3400(2) 1.1153(2) 0.44887(13) 0.0221 1.0000 Uani . . . . . .
C26 C 0.4959(2) 1.2728(2) 0.26426(12) 0.0177 1.0000 Uani . . . . . .
C27 C 0.5930(2) 1.2313(2) 0.22089(13) 0.0211 1.0000 Uani . . . . . .
C28 C 0.6003(2) 1.1369(2) 0.19836(12) 0.0198 1.0000 Uani . . . . . .
C29 C 0.5025(2) 1.3724(2) 0.28734(13) 0.0215 1.0000 Uani D . . . . .
O30 O 0.59065(16) 1.41421(16) 0.27273(10) 0.0284 1.0000 Uani . . . . . .
N31 N 0.40420(19) 1.41600(18) 0.32810(11) 0.0219 1.0000 Uani D . . . . .
S32 S 0.41611(6) 1.49398(5) 0.38109(3) 0.0209 1.0000 Uani D . . . . .
O33 O 0.42822(17) 1.60502(15) 0.33756(10) 0.0294 1.0000 Uani . . . . . .
O34 O 0.31212(16) 1.48566(15) 0.42929(10) 0.0268 1.0000 Uani . . . . . .
C35 C 0.5558(2) 1.4171(2) 0.42990(13) 0.0209 1.0000 Uani . . . . . .
C36 C 0.6663(2) 1.4500(2) 0.40850(13) 0.0222 1.0000 Uani . . . . . .
C37 C 0.7735(2) 1.3900(2) 0.44853(13) 0.0228 1.0000 Uani . . . . . .
C38 C 0.7780(2) 1.2940(2) 0.51190(12) 0.0206 1.0000 Uani D . . . . .
N39 N 0.88380(19) 1.24110(19) 0.55137(11) 0.0251 1.0000 Uani D . . . . .
C40 C 0.9899(2) 1.2902(2) 0.54269(14) 0.0273 1.0000 Uani D . . . . .
C41 C 1.0863(2) 1.2229(2) 0.60388(14) 0.0273 1.0000 Uani . . . . . .
C42 C 1.0309(3) 1.2120(3) 0.68015(14) 0.0330 1.0000 Uani . . . . . .
C43 C 1.1352(3) 1.1600(3) 0.73801(16) 0.0464 1.0000 Uani . . . . . .
O44 O 1.2239(2) 1.2258(2) 0.72445(12) 0.0499 1.0000 Uani . . . . . .
C45 C 1.2837(3) 1.2258(3) 0.65626(18) 0.0443 1.0000 Uani . . . . . .
C46 C 1.1907(3) 1.2832(3) 0.59350(16) 0.0360 1.0000 Uani . . . . . .
C47 C 0.6648(2) 1.2606(2) 0.52949(13) 0.0215 1.0000 Uani . . . . . .
C48 C 0.5556(2) 1.3226(2) 0.48947(13) 0.0217 1.0000 Uani . . . . . .
N49 N 0.6554(2) 1.16440(18) 0.59219(12) 0.0269 1.0000 Uani . . . . . .
O50 O 0.55688(18) 1.13726(17) 0.60321(11) 0.0403 1.0000 Uani . . . . . .
O51 O 0.74684(17) 1.11120(16) 0.63390(10) 0.0330 1.0000 Uani . . . . . .
C52 C 0.5680(2) 0.9789(2) 0.12240(13) 0.0216 1.0000 Uani . . . . . .
C53 C 0.6160(2) 0.8551(2) 0.12054(13) 0.0184 1.0000 Uani D . . . . .
C54 C 0.5548(2) 0.6873(2) 0.00652(14) 0.0296 1.0000 Uani . . . . . .
C55 C 0.6346(3) 0.7068(3) -0.06427(17) 0.0479 1.0000 Uani . . . . . .
C56 C 0.7522(2) 0.6117(3) -0.05855(14) 0.0326 1.0000 Uani . . . . . .
C57 C 0.8295(2) 0.5939(3) 0.00719(15) 0.0333 1.0000 Uani . . . . . .
C58 C 0.8248(3) 0.6322(4) -0.12886(18) 0.0619 1.0000 Uani . . . . . .
C59 C 0.7202(4) 0.4937(3) -0.0483(2) 0.0626 1.0000 Uani . . . . . .
C60 C 0.8319(2) 0.4747(2) 0.20072(14) 0.0233 1.0000 Uani . . . . . .
C61 C 0.9062(2) 0.4403(2) 0.26249(14) 0.0235 1.0000 Uani . . . . . .
O62 O 0.66948(15) 1.05644(16) -0.03541(9) 0.0262 1.0000 Uani . . . . . .
C63 C 0.7782(2) 1.0601(2) -0.02938(14) 0.0274 1.0000 Uani . . . . . .
O64 O 0.86124(18) 0.9888(2) 0.01376(13) 0.0536 1.0000 Uani . . . . . .
C65 C 0.8143(2) 1.1670(2) -0.08208(15) 0.0286 1.0000 Uani . . . . . .
O66 O 0.73993(17) 1.24744(17) -0.12151(12) 0.0412 1.0000 Uani . . . . . .
O67 O 0.93371(18) 1.16529(18) -0.08114(12) 0.0435 1.0000 Uani D . . . . .
N68 N 0.9521(4) 1.1462(4) 0.2435(2) 0.0799 1.0000 Uani . . . . . .
C69 C 0.9570(4) 1.1440(4) 0.1867(3) 0.0666 1.0000 Uani . . . . . .
C70 C 0.9550(7) 1.1529(8) 0.1093(3) 0.1617 1.0000 Uani . . . . . .
H31 H 1.0604 0.6367 0.2072 0.0275 1.0000 Uiso R . . . . .
H41 H 0.9285 0.6942 0.1057 0.0269 1.0000 Uiso R . . . . .
H82 H 0.6191 0.6285 0.1867 0.0269 1.0000 Uiso R . . . . .
H81 H 0.4916 0.6341 0.1465 0.0264 1.0000 Uiso R . . . . .
H101 H 0.5194 0.7612 0.2472 0.0249 1.0000 Uiso R . . . . .
H102 H 0.3869 0.7691 0.2170 0.0254 1.0000 Uiso R . . . . .
H111 H 0.3754 0.9306 0.2575 0.0255 1.0000 Uiso R . . . . .
H112 H 0.3400 0.9724 0.1711 0.0242 1.0000 Uiso R . . . . .
H141 H 0.3487 1.0773 0.2787 0.0221 1.0000 Uiso R . . . . .
H181 H 0.1059 1.1887 0.3354 0.0261 1.0000 Uiso R . . . . .
H221 H 0.2347 0.8635 0.6552 0.0316 1.0000 Uiso R . . . . .
H231 H 0.4085 0.9572 0.6032 0.0297 1.0000 Uiso R . . . . .
H251 H 0.4201 1.1302 0.4538 0.0289 1.0000 Uiso R . . . . .
H271 H 0.6603 1.2704 0.2057 0.0261 1.0000 Uiso R . . . . .
H281 H 0.6680 1.1123 0.1692 0.0242 1.0000 Uiso R . . . . .
H361 H 0.6657 1.5132 0.3659 0.0264 1.0000 Uiso R . . . . .
H371 H 0.8449 1.4134 0.4324 0.0289 1.0000 Uiso R . . . . .
H402 H 0.9573 1.3727 0.5423 0.0330 1.0000 Uiso R . . . . .
H401 H 1.0290 1.2854 0.4949 0.0338 1.0000 Uiso R . . . . .
H411 H 1.1251 1.1450 0.6003 0.0331 1.0000 Uiso R . . . . .
H422 H 0.9833 1.2916 0.6826 0.0415 1.0000 Uiso R . . . . .
H421 H 0.9746 1.1615 0.6932 0.0411 1.0000 Uiso R . . . . .
H431 H 1.0996 1.1583 0.7857 0.0561 1.0000 Uiso R . . . . .
H432 H 1.1770 1.0813 0.7374 0.0552 1.0000 Uiso R . . . . .
H451 H 1.3464 1.2680 0.6504 0.0547 1.0000 Uiso R . . . . .
H452 H 1.3226 1.1434 0.6593 0.0545 1.0000 Uiso R . . . . .
H461 H 1.1526 1.3640 0.5922 0.0430 1.0000 Uiso R . . . . .
H462 H 1.2352 1.2799 0.5479 0.0429 1.0000 Uiso R . . . . .
H481 H 0.4803 1.2982 0.5046 0.0271 1.0000 Uiso R . . . . .
H522 H 0.6397 1.0118 0.1158 0.0274 1.0000 Uiso R . . . . .
H521 H 0.5063 1.0262 0.0812 0.0272 1.0000 Uiso R . . . . .
H532 H 0.6807 0.8112 0.1558 0.0224 1.0000 Uiso R . . . . .
H531 H 0.6499 0.8519 0.0729 0.0230 1.0000 Uiso R . . . . .
H541 H 0.5144 0.6284 0.0104 0.0373 1.0000 Uiso R . . . . .
H542 H 0.4916 0.7609 0.0038 0.0367 1.0000 Uiso R . . . . .
H552 H 0.6819 0.7769 -0.0739 0.0601 1.0000 Uiso R . . . . .
H551 H 0.5833 0.7079 -0.1049 0.0604 1.0000 Uiso R . . . . .
H571 H 0.8843 0.5141 0.0187 0.0432 1.0000 Uiso R . . . . .
H572 H 0.8780 0.6529 -0.0070 0.0428 1.0000 Uiso R . . . . .
H581 H 0.8982 0.5673 -0.1203 0.0964 1.0000 Uiso R . . . . .
H582 H 0.8424 0.7098 -0.1368 0.0975 1.0000 Uiso R . . . . .
H583 H 0.7751 0.6331 -0.1698 0.0952 1.0000 Uiso R . . . . .
H592 H 0.7996 0.4339 -0.0519 0.0935 1.0000 Uiso R . . . . .
H591 H 0.6567 0.5074 -0.0902 0.0939 1.0000 Uiso R . . . . .
H593 H 0.6754 0.4695 0.0026 0.0938 1.0000 Uiso R . . . . .
H601 H 0.7763 0.4324 0.1997 0.0293 1.0000 Uiso R . . . . .
H611 H 0.8988 0.3758 0.3037 0.0290 1.0000 Uiso R . . . . .
H702 H 0.9860 1.0747 0.1080 0.2232 1.0000 Uiso R . . . . .
H701 H 1.0062 1.2010 0.0816 0.2231 1.0000 Uiso R . . . . .
H703 H 0.8708 1.1823 0.0929 0.2237 1.0000 Uiso R . . . . .
H311 H 0.3407(18) 1.384(2) 0.3366(13) 0.0259(19) 1.0000 Uiso D . . . . .
H91 H 0.4545(16) 0.8309(16) 0.1027(10) 0.0259(19) 1.0000 Uiso D . . . . .
H211 H 0.0741(18) 0.930(2) 0.5637(10) 0.0273(19) 1.0000 Uiso D . . . . .
H671 H 0.974(3) 1.102(2) -0.0506(17) 0.063(2) 1.0000 Uiso D . . . . .
H391 H 0.8838(18) 1.1831(19) 0.5900(11) 0.0299(19) 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.19(3)
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 . 1.751(2) yes
C2 . C3 . 1.378(3) yes
C2 . C61 . 1.388(3) yes
C3 . C4 . 1.382(3) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.386(3) yes
C4 . H41 . 0.931 no
C5 . C6 . 1.499(3) yes
C5 . C60 . 1.392(3) yes
C6 . C7 . 1.339(3) yes
C6 . C57 . 1.511(3) yes
C7 . C8 . 1.496(3) yes
C7 . C54 . 1.518(3) yes
C8 . N9 . 1.524(3) yes
C8 . H82 . 1.006 no
C8 . H81 . 0.992 no
N9 . C10 . 1.498(3) yes
N9 . C53 . 1.493(3) yes
N9 . H91 . 0.901(16) no
C10 . C11 . 1.514(3) yes
C10 . H101 . 0.972 no
C10 . H102 . 0.976 no
C11 . N12 . 1.458(3) yes
C11 . H111 . 0.988 no
C11 . H112 . 1.013 no
N12 . C13 . 1.383(3) yes
N12 . C52 . 1.463(3) yes
C13 . C14 . 1.404(3) yes
C13 . C28 . 1.411(3) yes
C14 . C15 . 1.375(3) yes
C14 . H141 . 0.933 no
C15 . O16 . 1.388(3) yes
C15 . C26 . 1.407(3) yes
O16 . C17 . 1.405(3) yes
C17 . C18 . 1.395(3) yes
C17 . C25 . 1.376(3) yes
C18 . N19 . 1.336(3) yes
C18 . H181 . 0.954 no
N19 . C20 . 1.332(3) yes
C20 . N21 . 1.368(3) yes
C20 . C24 . 1.418(3) yes
N21 . C22 . 1.366(3) yes
N21 . H211 . 0.871(16) no
C22 . C23 . 1.364(4) yes
C22 . H221 . 0.959 no
C23 . C24 . 1.432(3) yes
C23 . H231 . 0.966 no
C24 . C25 . 1.400(3) yes
C25 . H251 . 0.981 no
C26 . C27 . 1.398(3) yes
C26 . C29 . 1.481(3) yes
C27 . C28 . 1.371(3) yes
C27 . H271 . 0.988 no
C28 . H281 . 0.944 no
C29 . O30 . 1.216(3) yes
C29 . N31 . 1.384(3) yes
N31 . S32 . 1.659(2) yes
N31 . H311 . 0.888(16) no
S32 . O33 . 1.4272(18) yes
S32 . O34 . 1.4344(18) yes
S32 . C35 . 1.748(2) yes
C35 . C36 . 1.401(3) yes
C35 . C48 . 1.372(3) yes
C36 . C37 . 1.365(3) yes
C36 . H361 . 0.947 no
C37 . C38 . 1.417(3) yes
C37 . H371 . 0.924 no
C38 . N39 . 1.339(3) yes
C38 . C47 . 1.424(3) yes
N39 . C40 . 1.460(3) yes
N39 . H391 . 0.865(16) no
C40 . C41 . 1.524(3) yes
C40 . H402 . 0.998 no
C40 . H401 . 0.999 no
C41 . C42 . 1.529(4) yes
C41 . C46 . 1.532(4) yes
C41 . H411 . 0.978 no
C42 . C43 . 1.530(4) yes
C42 . H422 . 1.009 no
C42 . H421 . 0.982 no
C43 . O44 . 1.422(4) yes
C43 . H431 . 0.969 no
C43 . H432 . 0.974 no
O44 . C45 . 1.426(4) yes
C45 . C46 . 1.511(4) yes
C45 . H451 . 0.971 no
C45 . H452 . 0.992 no
C46 . H461 . 0.981 no
C46 . H462 . 0.981 no
C47 . C48 . 1.386(3) yes
C47 . N49 . 1.441(3) yes
C48 . H481 . 0.968 no
N49 . O50 . 1.225(3) yes
N49 . O51 . 1.241(3) yes
C52 . C53 . 1.512(3) yes
C52 . H522 . 0.984 no
C52 . H521 . 1.008 no
C53 . H532 . 0.951 no
C53 . H531 . 0.973 no
C54 . C55 . 1.561(4) yes
C54 . H541 . 0.954 no
C54 . H542 . 0.984 no
C55 . C56 . 1.492(4) yes
C55 . H552 . 1.114 no
C55 . H551 . 0.999 no
C56 . C57 . 1.510(4) yes
C56 . C58 . 1.511(4) yes
C56 . C59 . 1.577(5) yes
C57 . H571 . 0.984 no
C57 . H572 . 1.000 no
C58 . H581 . 0.961 no
C58 . H582 . 1.015 no
C58 . H583 . 0.995 no
C59 . H592 . 1.002 no
C59 . H591 . 1.056 no
C59 . H593 . 1.061 no
C60 . C61 . 1.385(3) yes
C60 . H601 . 0.930 no
C61 . H611 . 0.960 no
O62 . C63 . 1.242(3) yes
C63 . O64 . 1.240(3) yes
C63 . C65 . 1.548(4) yes
C65 . O66 . 1.198(3) yes
C65 . O67 . 1.328(3) yes
O67 . H671 . 0.853(18) no
N68 . C69 . 1.100(5) yes
C69 . C70 . 1.460(7) yes
C70 . H702 . 0.958 no
C70 . H701 . 0.961 no
C70 . H703 . 0.946 no
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 . 119.45(19) yes
Cl1 . C2 . C61 . 118.71(19) yes
C3 . C2 . C61 . 121.8(2) yes
C2 . C3 . C4 . 118.6(2) yes
C2 . C3 . H31 . 120.3 no
C4 . C3 . H31 . 121.1 no
C3 . C4 . C5 . 121.5(2) yes
C3 . C4 . H41 . 120.1 no
C5 . C4 . H41 . 118.4 no
C4 . C5 . C6 . 120.6(2) yes
C4 . C5 . C60 . 118.4(2) yes
C6 . C5 . C60 . 120.9(2) yes
C5 . C6 . C7 . 123.1(2) yes
C5 . C6 . C57 . 113.87(19) yes
C7 . C6 . C57 . 123.0(2) yes
C6 . C7 . C8 . 122.6(2) yes
C6 . C7 . C54 . 121.5(2) yes
C8 . C7 . C54 . 115.9(2) yes
C7 . C8 . N9 . 112.27(19) yes
C7 . C8 . H82 . 110.5 no
N9 . C8 . H82 . 106.9 no
C7 . C8 . H81 . 107.0 no
N9 . C8 . H81 . 109.2 no
H82 . C8 . H81 . 111.0 no
C8 . N9 . C10 . 108.86(17) yes
C8 . N9 . C53 . 111.82(17) yes
C10 . N9 . C53 . 109.67(18) yes
C8 . N9 . H91 . 109.2(12) no
C10 . N9 . H91 . 107.8(12) no
C53 . N9 . H91 . 109.4(12) no
N9 . C10 . C11 . 111.40(18) yes
N9 . C10 . H101 . 107.8 no
C11 . C10 . H101 . 109.9 no
N9 . C10 . H102 . 107.6 no
C11 . C10 . H102 . 110.1 no
H101 . C10 . H102 . 110.0 no
C10 . C11 . N12 . 110.28(19) yes
C10 . C11 . H111 . 108.4 no
N12 . C11 . H111 . 109.7 no
C10 . C11 . H112 . 109.4 no
N12 . C11 . H112 . 110.5 no
H111 . C11 . H112 . 108.6 no
C11 . N12 . C13 . 120.16(19) yes
C11 . N12 . C52 . 110.95(18) yes
C13 . N12 . C52 . 120.47(19) yes
N12 . C13 . C14 . 121.6(2) yes
N12 . C13 . C28 . 121.2(2) yes
C14 . C13 . C28 . 117.2(2) yes
C13 . C14 . C15 . 120.8(2) yes
C13 . C14 . H141 . 121.1 no
C15 . C14 . H141 . 118.1 no
C14 . C15 . O16 . 119.3(2) yes
C14 . C15 . C26 . 122.6(2) yes
O16 . C15 . C26 . 117.9(2) yes
C15 . O16 . C17 . 118.00(18) yes
O16 . C17 . C18 . 117.1(2) yes
O16 . C17 . C25 . 120.4(2) yes
C18 . C17 . C25 . 122.2(2) yes
C17 . C18 . N19 . 122.4(2) yes
C17 . C18 . H181 . 119.1 no
N19 . C18 . H181 . 118.6 no
C18 . N19 . C20 . 115.39(19) yes
N19 . C20 . N21 . 125.4(2) yes
N19 . C20 . C24 . 126.6(2) yes
N21 . C20 . C24 . 108.0(2) yes
C20 . N21 . C22 . 108.3(2) yes
C20 . N21 . H211 . 125.3(11) no
C22 . N21 . H211 . 126.4(11) no
N21 . C22 . C23 . 110.9(2) yes
N21 . C22 . H221 . 122.1 no
C23 . C22 . H221 . 127.1 no
C22 . C23 . C24 . 106.3(2) yes
C22 . C23 . H231 . 127.6 no
C24 . C23 . H231 . 126.1 no
C23 . C24 . C20 . 106.5(2) yes
C23 . C24 . C25 . 137.0(2) yes
C20 . C24 . C25 . 116.5(2) yes
C24 . C25 . C17 . 116.8(2) yes
C24 . C25 . H251 . 120.8 no
C17 . C25 . H251 . 122.4 no
C15 . C26 . C27 . 115.7(2) yes
C15 . C26 . C29 . 127.0(2) yes
C27 . C26 . C29 . 117.1(2) yes
C26 . C27 . C28 . 122.8(2) yes
C26 . C27 . H271 . 119.8 no
C28 . C27 . H271 . 117.4 no
C13 . C28 . C27 . 120.8(2) yes
C13 . C28 . H281 . 119.8 no
C27 . C28 . H281 . 119.4 no
C26 . C29 . O30 . 122.4(2) yes
C26 . C29 . N31 . 117.1(2) yes
O30 . C29 . N31 . 120.5(2) yes
C29 . N31 . S32 . 123.01(17) yes
C29 . N31 . H311 . 117.7(11) no
S32 . N31 . H311 . 116.8(11) no
N31 . S32 . O33 . 110.33(11) yes
N31 . S32 . O34 . 102.97(10) yes
O33 . S32 . O34 . 120.00(11) yes
N31 . S32 . C35 . 104.45(11) yes
O33 . S32 . C35 . 108.24(11) yes
O34 . S32 . C35 . 109.72(11) yes
S32 . C35 . C36 . 121.06(18) yes
S32 . C35 . C48 . 118.58(18) yes
C36 . C35 . C48 . 120.4(2) yes
C35 . C36 . C37 . 119.9(2) yes
C35 . C36 . H361 . 119.3 no
C37 . C36 . H361 . 120.8 no
C36 . C37 . C38 . 122.2(2) yes
C36 . C37 . H371 . 117.5 no
C38 . C37 . H371 . 120.3 no
C37 . C38 . N39 . 120.2(2) yes
C37 . C38 . C47 . 115.8(2) yes
N39 . C38 . C47 . 124.1(2) yes
C38 . N39 . C40 . 123.4(2) yes
C38 . N39 . H391 . 118.2(11) no
C40 . N39 . H391 . 116.9(11) no
N39 . C40 . C41 . 111.7(2) yes
N39 . C40 . H402 . 107.9 no
C41 . C40 . H402 . 110.3 no
N39 . C40 . H401 . 106.8 no
C41 . C40 . H401 . 109.2 no
H402 . C40 . H401 . 110.8 no
C40 . C41 . C42 . 113.1(2) yes
C40 . C41 . C46 . 108.7(2) yes
C42 . C41 . C46 . 109.8(2) yes
C40 . C41 . H411 . 109.9 no
C42 . C41 . H411 . 108.6 no
C46 . C41 . H411 . 106.6 no
C41 . C42 . C43 . 110.2(2) yes
C41 . C42 . H422 . 109.0 no
C43 . C42 . H422 . 108.8 no
C41 . C42 . H421 . 113.1 no
C43 . C42 . H421 . 106.7 no
H422 . C42 . H421 . 108.9 no
C42 . C43 . O44 . 111.9(3) yes
C42 . C43 . H431 . 109.5 no
O44 . C43 . H431 . 108.2 no
C42 . C43 . H432 . 108.1 no
O44 . C43 . H432 . 109.4 no
H431 . C43 . H432 . 109.8 no
C43 . O44 . C45 . 110.2(2) yes
O44 . C45 . C46 . 111.2(2) yes
O44 . C45 . H451 . 107.6 no
C46 . C45 . H451 . 109.9 no
O44 . C45 . H452 . 106.6 no
C46 . C45 . H452 . 110.2 no
H451 . C45 . H452 . 111.4 no
C41 . C46 . C45 . 111.0(3) yes
C41 . C46 . H461 . 108.0 no
C45 . C46 . H461 . 108.6 no
C41 . C46 . H462 . 110.2 no
C45 . C46 . H462 . 108.6 no
H461 . C46 . H462 . 110.5 no
C38 . C47 . C48 . 121.9(2) yes
C38 . C47 . N49 . 122.0(2) yes
C48 . C47 . N49 . 116.0(2) yes
C47 . C48 . C35 . 119.8(2) yes
C47 . C48 . H481 . 118.8 no
C35 . C48 . H481 . 121.4 no
C47 . N49 . O50 . 119.1(2) yes
C47 . N49 . O51 . 119.4(2) yes
O50 . N49 . O51 . 121.5(2) yes
N12 . C52 . C53 . 111.46(19) yes
N12 . C52 . H522 . 107.8 no
C53 . C52 . H522 . 107.8 no
N12 . C52 . H521 . 110.7 no
C53 . C52 . H521 . 110.3 no
H522 . C52 . H521 . 108.6 no
C52 . C53 . N9 . 110.97(18) yes
C52 . C53 . H532 . 111.5 no
N9 . C53 . H532 . 106.8 no
C52 . C53 . H531 . 111.4 no
N9 . C53 . H531 . 108.6 no
H532 . C53 . H531 . 107.4 no
C7 . C54 . C55 . 112.3(2) yes
C7 . C54 . H541 . 107.6 no
C55 . C54 . H541 . 110.8 no
C7 . C54 . H542 . 108.6 no
C55 . C54 . H542 . 107.9 no
H541 . C54 . H542 . 109.6 no
C54 . C55 . C56 . 112.8(3) yes
C54 . C55 . H552 . 115.1 no
C56 . C55 . H552 . 95.3 no
C54 . C55 . H551 . 107.3 no
C56 . C55 . H551 . 107.4 no
H552 . C55 . H551 . 118.3 no
C55 . C56 . C57 . 111.3(2) yes
C55 . C56 . C58 . 111.1(2) yes
C57 . C56 . C58 . 112.6(2) yes
C55 . C56 . C59 . 109.9(3) yes
C57 . C56 . C59 . 106.8(3) yes
C58 . C56 . C59 . 104.9(3) yes
C6 . C57 . C56 . 116.1(2) yes
C6 . C57 . H571 . 108.2 no
C56 . C57 . H571 . 106.1 no
C6 . C57 . H572 . 107.1 no
C56 . C57 . H572 . 107.4 no
H571 . C57 . H572 . 112.1 no
C56 . C58 . H581 . 105.4 no
C56 . C58 . H582 . 105.1 no
H581 . C58 . H582 . 114.4 no
C56 . C58 . H583 . 110.4 no
H581 . C58 . H583 . 109.3 no
H582 . C58 . H583 . 111.9 no
C56 . C59 . H592 . 108.4 no
C56 . C59 . H591 . 108.0 no
H592 . C59 . H591 . 110.6 no
C56 . C59 . H593 . 109.4 no
H592 . C59 . H593 . 112.4 no
H591 . C59 . H593 . 108.0 no
C5 . C60 . C61 . 121.3(2) yes
C5 . C60 . H601 . 120.5 no
C61 . C60 . H601 . 118.2 no
C2 . C61 . C60 . 118.3(2) yes
C2 . C61 . H611 . 120.9 no
C60 . C61 . H611 . 120.8 no
O62 . C63 . O64 . 128.0(3) yes
O62 . C63 . C65 . 115.9(2) yes
O64 . C63 . C65 . 116.1(2) yes
C63 . C65 . O66 . 122.8(2) yes
C63 . C65 . O67 . 116.1(2) yes
O66 . C65 . O67 . 121.1(2) yes
C65 . O67 . H671 . 109(2) no
N68 . C69 . C70 . 174.2(7) yes
C69 . C70 . H702 . 104.8 no
C69 . C70 . H701 . 110.8 no
H702 . C70 . H701 . 111.8 no
C69 . C70 . H703 . 108.0 no
H702 . C70 . H703 . 109.1 no
H701 . C70 . H703 . 112.0 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
C4 . H41 . O67 2_775 132 0.93 2.57 3.274(4) yes
C8 . H82 . C60 . 128 1.01 2.58 3.296(4) yes
C8 . H81 . O66 2_675 125 0.99 2.59 3.262(4) yes
C10 . H102 . O66 2_675 127 0.98 2.50 3.184(4) yes
C11 . H111 . O51 2_676 159 0.99 2.40 3.345(4) yes
C53 . H532 . O44 2_776 149 0.95 2.47 3.322(4) yes
C60 . H601 . O30 1_545 129 0.93 2.43 3.108(4) yes
N31 . H311 . O16 . 137.0(16) 0.888(16) 1.923(18) 2.643(4) yes
N9 . H91 . O62 2_675 163.8(17) 0.901(16) 1.905(17) 2.782(4) yes
N21 . H211 . N19 2_576 167(2) 0.871(16) 2.015(17) 2.871(4) yes
O67 . H671 . O64 2_775 143(3) 0.853(18) 1.93(3) 2.658(4) yes
N39 . H391 . O51 . 130.3(15) 0.865(16) 1.992(17) 2.636(4) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_systematic        Venetoclax
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2393684'
loop_
_audit_author_name
_audit_author_address
'Eliska Zmeskalova'
;Institute of Physics of the Czech Academy of Sciences
Czech Republic
;
_audit_update_record             
;
2024-10-25 deposited with the CCDC.	2025-02-12 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
 ? 
;

#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   10.80160(10)
_cell_length_b                   10.82230(10)
_cell_length_c                   14.07950(10)
_cell_angle_alpha                84.7041(9)
_cell_angle_beta                 83.8240(9)
_cell_angle_gamma                76.7040(10)
_cell_volume                     1588.57(2)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z

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'
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'
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'
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'


_cell_formula_units_Z            1

# Given Formula = C65 H66 Cl1 N7 O13 S3 
# Dc =      1.34 Fooo =    674.00 Mu =     20.27 M =   1284.93
# Found Formula = C66 H66 Cl1 N7.50 O13 S3 
# Dc =      1.36 FOOO =    683.50 Mu =     20.38 M =   1303.94

_chemical_formula_sum            'C66 H66 Cl1 N7.50 O13 S3'
_chemical_formula_moiety         'C66 H66 Cl1 N7.50 O13 S3'
_chemical_compound_source        .
_chemical_formula_weight         1303.94


_cell_measurement_reflns_used    45301
_cell_measurement_theta_min      4.17
_cell_measurement_theta_max      73.11
_cell_measurement_temperature    95

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.094
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_max          0.212

_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             683.500
_exptl_absorpt_coefficient_mu    2.038

# Sheldrick geometric approximatio 0.79 0.83 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_T_max  0.83
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      95
_diffrn_reflns_number            54398
_diffrn_reflns_av_unetI/netI     0.041
_reflns_number_total             11525
_diffrn_reflns_av_R_equivalents  0.036
# Number of reflections without Friedels Law is 11525 
# Number of reflections with Friedels Law is 6307 
# Theoretical number of reflections is about 6381 


_diffrn_reflns_theta_min         3.165
_diffrn_reflns_theta_max         73.299
_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        69.634
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -12
_reflns_limit_h_max              13
_reflns_limit_k_min              -13
_reflns_limit_k_max              13
_reflns_limit_l_min              -17
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   1.65
_oxford_diffrn_Wilson_scale      0.03

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.70


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     1122
_refine_ls_number_parameters     830
_refine_ls_number_reflns         11525
_oxford_refine_ls_R_factor_ref   0.0555
_refine_ls_R_factor_all          0.0555
_refine_ls_wR_factor_ref         0.1501
_refine_ls_wR_factor_all         0.1501
_refine_ls_goodness_of_fit_ref   1.0468
_refine_ls_shift/su_max          0.0003361
_refine_ls_shift/su_mean         0.0000262


# Computed with I/sigma = -10 
_oxford_reflns_number_all        11525
_oxford_refine_ls_R_factor_all   0.0555
_oxford_refine_ls_wR_factor_all  0.1501

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                11444
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_gt          0.1495

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  0. # for 0 Friedel pairs 
_oxford_Bijvoet_difference       0. # for 0 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.008(9) # for 5218 Friedel pairs 
_refine_ls_abs_structure_Flack   0.
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 0 Friedel Pairs 
;

# choose from: 
# rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.13P)² + 0.41P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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 0.50000(8) 0.50000(9) 0.50000(6) 0.0356 1.0000 Uani . . . . . .
C2 C 0.5928(3) 0.5554(3) 0.4027(2) 0.0250 1.0000 Uani . . . . . .
C3 C 0.6340(3) 0.4819(3) 0.3256(2) 0.0275 1.0000 Uani . . . . . .
C4 C 0.7065(3) 0.5274(3) 0.2488(2) 0.0235 1.0000 Uani . . . . . .
C5 C 0.7347(3) 0.6476(3) 0.24782(18) 0.0178 1.0000 Uani . . . . . .
C6 C 0.6915(3) 0.7198(3) 0.32639(19) 0.0191 1.0000 Uani . . . . . .
C7 C 0.6203(3) 0.6737(3) 0.4052(2) 0.0228 1.0000 Uani . . . . . .
H71 H 0.5940 0.7179 0.4593 0.0241 1.0000 Uiso R . . . . .
H61 H 0.7076 0.8001 0.3251 0.0211 1.0000 Uiso R . . . . .
C8 C 0.8163(3) 0.6941(2) 0.16616(17) 0.0173 1.0000 Uani . . . . . .
C9 C 0.7713(3) 0.7898(3) 0.10323(18) 0.0192 1.0000 Uani . . . . . .
C10 C 0.8586(3) 0.8391(3) 0.02376(19) 0.0220 1.0000 Uani . . . . . .
C11 C 0.9989(3) 0.7956(3) 0.0403(2) 0.0232 1.0000 Uani . . . . . .
C12 C 1.0357(3) 0.6528(3) 0.06919(19) 0.0227 1.0000 Uani . . . . . .
C13 C 0.9553(3) 0.6278(3) 0.16335(19) 0.0222 1.0000 Uani . . . . . .
H131 H 0.9905 0.6561 0.2174 0.0222 1.0000 Uiso R . . . . .
H132 H 0.9587 0.5365 0.1734 0.0236 1.0000 Uiso R . . . . .
C14 C 1.1772(3) 0.6138(3) 0.0853(2) 0.0309 1.0000 Uani . . . . . .
H141 H 1.2015 0.5312 0.1203 0.0443 1.0000 Uiso R . . . . .
H142 H 1.1948 0.6732 0.1271 0.0437 1.0000 Uiso R . . . . .
H143 H 1.2325 0.6177 0.0285 0.0434 1.0000 Uiso R . . . . .
C15 C 1.0106(3) 0.5750(3) -0.0090(2) 0.0289 1.0000 Uani . . . . . .
H151 H 1.0330 0.4865 0.0117 0.0400 1.0000 Uiso R . . . . .
H152 H 1.0610 0.5928 -0.0684 0.0396 1.0000 Uiso R . . . . .
H153 H 0.9218 0.6021 -0.0187 0.0401 1.0000 Uiso R . . . . .
H111 H 1.0155 0.8416 0.0925 0.0246 1.0000 Uiso R . . . . .
H112 H 1.0511 0.8173 -0.0173 0.0253 1.0000 Uiso R . . . . .
H101 H 0.8356 0.9329 0.0235 0.0230 1.0000 Uiso R . . . . .
H102 H 0.8446 0.8151 -0.0391 0.0234 1.0000 Uiso R . . . . .
C16 C 0.6335(3) 0.8592(3) 0.10795(18) 0.0185 1.0000 Uani D . . . . .
N17 N 0.5665(2) 0.8352(2) 0.02425(15) 0.0177 1.0000 Uani D . . . . .
C18 C 0.5551(3) 0.6995(3) 0.0263(2) 0.0206 1.0000 Uani D . . . . .
C19 C 0.4950(3) 0.6782(3) -0.0622(2) 0.0217 1.0000 Uani . . . . . .
N20 N 0.3744(2) 0.7697(2) -0.07668(16) 0.0173 1.0000 Uani . . . . . .
C21 C 0.3701(3) 0.9031(2) -0.06239(19) 0.0185 1.0000 Uani . . . . . .
C22 C 0.4359(3) 0.9175(3) 0.02520(19) 0.0205 1.0000 Uani D . . . . .
H221 H 0.4392 1.0053 0.0254 0.0213 1.0000 Uiso R . . . . .
H222 H 0.3841 0.8939 0.0832 0.0207 1.0000 Uiso R . . . . .
H211 H 0.4093 0.9424 -0.1206 0.0215 1.0000 Uiso R . . . . .
H212 H 0.2785 0.9449 -0.0513 0.0206 1.0000 Uiso R . . . . .
C23 C 0.3085(3) 0.7479(2) -0.15141(18) 0.0169 1.0000 Uani . . . . . .
C24 C 0.2161(3) 0.8463(2) -0.19191(18) 0.0171 1.0000 Uani . . . . . .
C25 C 0.1493(3) 0.8242(2) -0.26464(18) 0.0160 1.0000 Uani . . . . . .
O26 O 0.06346(19) 0.92224(17) -0.30881(13) 0.0175 1.0000 Uani . . . . . .
C27 C 0.0238(3) 1.0368(2) -0.26558(18) 0.0163 1.0000 Uani . . . . . .
C28 C 0.0750(3) 1.1390(2) -0.30316(18) 0.0169 1.0000 Uani . . . . . .
C29 C 0.0246(3) 1.2565(3) -0.26451(17) 0.0167 1.0000 Uani . . . . . .
C30 C -0.0775(3) 1.2637(2) -0.19182(18) 0.0164 1.0000 Uani D . . . . .
N31 N -0.1168(2) 1.3840(2) -0.16500(16) 0.0199 1.0000 Uani D . . . . .
C32 C -0.0405(3) 1.4562(3) -0.21981(19) 0.0217 1.0000 Uani D . . . . .
C33 C 0.0464(3) 1.3827(2) -0.28004(19) 0.0197 1.0000 Uani . . . . . .
H331 H 0.1089 1.4093 -0.3242 0.0208 1.0000 Uiso R . . . . .
H321 H -0.0482 1.5425 -0.2157 0.0223 1.0000 Uiso R . . . . .
H311 H -0.174(3) 1.4088(18) -0.1195(19) 0.0222 1.0000 Uiso D . . . . .
N34 N -0.1213(2) 1.1612(2) -0.15486(16) 0.0168 1.0000 Uani D . . . . .
C35 C -0.0711(3) 1.0474(2) -0.19106(18) 0.0175 1.0000 Uani D . . . . .
H351 H -0.0982 0.9762 -0.1649 0.0192 1.0000 Uiso R . . . . .
H341 H -0.181(3) 1.1667(17) -0.1086(19) 0.0192 1.0000 Uiso D . . . . .
H281 H 0.1394 1.1282 -0.3522 0.0189 1.0000 Uiso R . . . . .
C36 C 0.1714(3) 0.7043(2) -0.30221(18) 0.0171 1.0000 Uani . . . . . .
C37 C 0.1104(3) 0.6715(2) -0.38414(17) 0.0168 1.0000 Uani D . . . . .
O38 O 0.1643(2) 0.58244(18) -0.43186(13) 0.0194 1.0000 Uani . . . . . .
N39 N -0.0093(2) 0.7395(2) -0.40150(16) 0.0187 1.0000 Uani D . . . . .
S40 S -0.08427(7) 0.71402(6) -0.49265(5) 0.0168 1.0000 Uani D . . . . .
O41 O -0.2041(2) 0.80258(18) -0.48225(14) 0.0215 1.0000 Uani . . . . . .
O42 O -0.0023(2) 0.71854(18) -0.57903(14) 0.0218 1.0000 Uani . . . . . .
C43 C -0.1110(3) 0.5596(2) -0.47252(19) 0.0179 1.0000 Uani . . . . . .
C44 C -0.0482(3) 0.4654(3) -0.53394(18) 0.0192 1.0000 Uani . . . . . .
C45 C -0.0758(3) 0.3467(3) -0.52280(19) 0.0194 1.0000 Uani . . . . . .
C46 C -0.1664(3) 0.3145(3) -0.44922(18) 0.0182 1.0000 Uani D . . . . .
N47 N -0.1879(3) 0.1962(2) -0.43894(16) 0.0211 1.0000 Uani D . . . . .
C48 C -0.1333(3) 0.0978(3) -0.5051(2) 0.0222 1.0000 Uani D . . . . .
C49 C -0.1965(3) 0.1201(2) -0.59916(18) 0.0190 1.0000 Uani . . . . . .
C50 C -0.1222(3) 0.0289(3) -0.6724(2) 0.0224 1.0000 Uani . . . . . .
C51 C -0.1906(3) 0.0477(3) -0.7629(2) 0.0249 1.0000 Uani . . . . . .
O52 O -0.3174(2) 0.0248(2) -0.74231(15) 0.0265 1.0000 Uani . . . . . .
C53 C -0.3927(3) 0.1123(3) -0.6777(2) 0.0245 1.0000 Uani . . . . . .
C54 C -0.3344(3) 0.1041(3) -0.58293(19) 0.0213 1.0000 Uani . . . . . .
H541 H -0.3348 0.0237 -0.5466 0.0240 1.0000 Uiso R . . . . .
H542 H -0.3825 0.1742 -0.5458 0.0233 1.0000 Uiso R . . . . .
H531 H -0.3974 0.2011 -0.7062 0.0272 1.0000 Uiso R . . . . .
H532 H -0.4762 0.0932 -0.6676 0.0275 1.0000 Uiso R . . . . .
H511 H -0.1406 -0.0124 -0.8077 0.0279 1.0000 Uiso R . . . . .
H512 H -0.1966 0.1357 -0.7901 0.0279 1.0000 Uiso R . . . . .
H501 H -0.0341 0.0405 -0.6883 0.0253 1.0000 Uiso R . . . . .
H502 H -0.1166 -0.0564 -0.6458 0.0257 1.0000 Uiso R . . . . .
H491 H -0.1983 0.2078 -0.6245 0.0201 1.0000 Uiso R . . . . .
H482 H -0.0444 0.0973 -0.5185 0.0246 1.0000 Uiso R . . . . .
H481 H -0.1404 0.0158 -0.4759 0.0247 1.0000 Uiso R . . . . .
H471 H -0.234(3) 0.1775(19) -0.3897(17) 0.0229 1.0000 Uiso D . . . . .
C55 C -0.2287(3) 0.4141(3) -0.38996(18) 0.0182 1.0000 Uani . . . . . .
C56 C -0.2022(3) 0.5354(2) -0.40182(18) 0.0175 1.0000 Uani . . . . . .
H561 H -0.2451 0.5975 -0.3617 0.0187 1.0000 Uiso R . . . . .
N57 N -0.3276(2) 0.3969(2) -0.31478(16) 0.0201 1.0000 Uani . . . . . .
O58 O -0.3889(2) 0.4890(2) -0.27335(16) 0.0288 1.0000 Uani . . . . . .
O59 O -0.3470(2) 0.2885(2) -0.29414(15) 0.0298 1.0000 Uani . . . . . .
H451 H -0.0340 0.2866 -0.5637 0.0206 1.0000 Uiso R . . . . .
H441 H 0.0113 0.4821 -0.5853 0.0208 1.0000 Uiso R . . . . .
H391 H -0.051(2) 0.795(3) -0.3638(17) 0.0209 1.0000 Uiso D . . . . .
C60 C 0.2649(3) 0.6088(2) -0.26214(19) 0.0196 1.0000 Uani . . . . . .
C61 C 0.3313(3) 0.6273(2) -0.18776(19) 0.0183 1.0000 Uani . . . . . .
H611 H 0.3906 0.5596 -0.1613 0.0209 1.0000 Uiso R . . . . .
H601 H 0.2879 0.5282 -0.2876 0.0227 1.0000 Uiso R . . . . .
H241 H 0.2003 0.9291 -0.1692 0.0177 1.0000 Uiso R . . . . .
H191 H 0.5537 0.6839 -0.1184 0.0240 1.0000 Uiso R . . . . .
H192 H 0.4779 0.5921 -0.0539 0.0240 1.0000 Uiso R . . . . .
H181 H 0.6382 0.6458 0.0285 0.0217 1.0000 Uiso R . . . . .
H182 H 0.5032 0.6821 0.0843 0.0212 1.0000 Uiso R . . . . .
H171 H 0.6122(19) 0.8527(19) -0.0303(13) 0.0245 1.0000 Uiso D . . . . .
H162 H 0.6262 0.9497 0.1104 0.0189 1.0000 Uiso R . . . . .
H161 H 0.5894 0.8275 0.1641 0.0192 1.0000 Uiso R . . . . .
H41 H 0.7335 0.4790 0.1967 0.0246 1.0000 Uiso R . . . . .
H31 H 0.6154 0.4026 0.3248 0.0314 1.0000 Uiso R . . . . .
S62 S 0.64410(7) 0.29943(6) 0.03109(5) 0.0186 1.0000 Uani . . . . . .
O63 O 0.6439(2) 0.3239(2) 0.12937(16) 0.0258 1.0000 Uani . . . . . .
O64 O 0.7293(2) 0.17739(18) 0.00576(14) 0.0216 1.0000 Uani . . . . . .
O65 O 0.6666(2) 0.40346(19) -0.03803(16) 0.0274 1.0000 Uani . . . . . .
C66 C 0.4891(3) 0.2796(2) 0.01608(19) 0.0200 1.0000 Uani . . . . . .
C67 C 0.4576(3) 0.2668(3) -0.0774(2) 0.0262 1.0000 Uani . . . . . .
C68 C 0.3401(3) 0.2448(3) -0.0888(2) 0.0274 1.0000 Uani . . . . . .
C69 C 0.2501(3) 0.2357(3) -0.0092(2) 0.0249 1.0000 Uani . . . . . .
C70 C 0.2812(3) 0.2517(3) 0.0839(2) 0.0252 1.0000 Uani . . . . . .
C71 C 0.4043(3) 0.2729(3) 0.0942(2) 0.0225 1.0000 Uani . . . . . .
H711 H 0.4276 0.2823 0.1538 0.0255 1.0000 Uiso R . . . . .
C72 C 0.1898(4) 0.2455(4) 0.1631(2) 0.0359 1.0000 Uani . . . . . .
C73 C 0.0720(4) 0.2237(4) 0.1501(3) 0.0425 1.0000 Uani . . . . . .
C74 C 0.0436(4) 0.2036(3) 0.0585(3) 0.0378 1.0000 Uani . . . . . .
C75 C 0.1295(3) 0.2096(3) -0.0187(3) 0.0317 1.0000 Uani . . . . . .
H751 H 0.1076 0.1966 -0.0808 0.0360 1.0000 Uiso R . . . . .
H741 H -0.0353 0.1826 0.0495 0.0447 1.0000 Uiso R . . . . .
H731 H 0.0113 0.2207 0.2023 0.0474 1.0000 Uiso R . . . . .
H721 H 0.2078 0.2564 0.2249 0.0415 1.0000 Uiso R . . . . .
H681 H 0.3198 0.2363 -0.1499 0.0301 1.0000 Uiso R . . . . .
H671 H 0.5149 0.2705 -0.1303 0.0292 1.0000 Uiso R . . . . .
S76 S 0.69641(7) 0.86860(7) -0.24152(5) 0.0211 1.0000 Uani . . . . . .
O77 O 0.6578(2) 0.9299(2) -0.15105(14) 0.0253 1.0000 Uani . . . . . .
O78 O 0.7258(2) 0.7311(2) -0.22885(16) 0.0313 1.0000 Uani . . . . . .
O79 O 0.7977(2) 0.9192(2) -0.29726(15) 0.0296 1.0000 Uani . . . . . .
C80 C 0.5622(3) 0.9156(3) -0.31005(19) 0.0206 1.0000 Uani . . . . . .
C81 C 0.5136(3) 0.8235(3) -0.3494(2) 0.0238 1.0000 Uani . . . . . .
C82 C 0.4218(3) 0.8612(3) -0.4129(2) 0.0296 1.0000 Uani . . . . . .
C83 C 0.3765(3) 0.9903(4) -0.4389(2) 0.0322 1.0000 Uani . . . . . .
C84 C 0.4196(3) 1.0843(3) -0.3945(2) 0.0303 1.0000 Uani . . . . . .
C85 C 0.5145(3) 1.0433(3) -0.3290(2) 0.0264 1.0000 Uani . . . . . .
H851 H 0.5430 1.1054 -0.2988 0.0308 1.0000 Uiso R . . . . .
C86 C 0.3732(4) 1.2150(4) -0.4205(3) 0.0424 1.0000 Uani . . . . . .
C87 C 0.2915(4) 1.2520(4) -0.4905(3) 0.0513 1.0000 Uani . . . . . .
C88 C 0.2527(4) 1.1598(5) -0.5370(3) 0.0524 1.0000 Uani . . . . . .
C89 C 0.2912(4) 1.0329(5) -0.5124(2) 0.0432 1.0000 Uani . . . . . .
H891 H 0.2635 0.9691 -0.5436 0.0489 1.0000 Uiso R . . . . .
H881 H 0.1965 1.1861 -0.5851 0.0603 1.0000 Uiso R . . . . .
H871 H 0.2634 1.3407 -0.5081 0.0609 1.0000 Uiso R . . . . .
H861 H 0.3998 1.2764 -0.3899 0.0496 1.0000 Uiso R . . . . .
H821 H 0.3885 0.7971 -0.4390 0.0328 1.0000 Uiso R . . . . .
H811 H 0.5447 0.7345 -0.3322 0.0273 1.0000 Uiso R . . . . .
N90 N 0.3391(9) 0.7965(8) 0.2608(6) 0.0582(18) 0.5000 Uiso . . . . . .
C91 C 0.3104(8) 0.7075(7) 0.2924(5) 0.0395(15) 0.5000 Uiso . . . . . .
C92 C 0.2753(7) 0.5912(6) 0.3313(4) 0.0294(12) 0.5000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.93(12)
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 . 1.753(3) yes
C2 . C3 . 1.379(5) yes
C2 . C7 . 1.383(4) yes
C3 . C4 . 1.386(4) yes
C3 . H31 . 0.927 no
C4 . C5 . 1.401(4) yes
C4 . H41 . 0.924 no
C5 . C6 . 1.391(4) yes
C5 . C8 . 1.494(4) yes
C6 . C7 . 1.402(4) yes
C6 . H61 . 0.922 no
C7 . H71 . 0.920 no
C8 . C9 . 1.336(4) yes
C8 . C13 . 1.506(4) yes
C9 . C10 . 1.523(4) yes
C9 . C16 . 1.503(4) yes
C10 . C11 . 1.517(4) yes
C10 . H101 . 0.988 no
C10 . H102 . 0.981 no
C11 . C12 . 1.532(4) yes
C11 . H111 . 0.978 no
C11 . H112 . 0.978 no
C12 . C13 . 1.542(4) yes
C12 . C14 . 1.525(4) yes
C12 . C15 . 1.528(4) yes
C13 . H131 . 0.988 no
C13 . H132 . 0.978 no
C14 . H141 . 0.975 no
C14 . H142 . 0.972 no
C14 . H143 . 0.950 no
C15 . H151 . 0.958 no
C15 . H152 . 0.976 no
C15 . H153 . 0.957 no
C16 . N17 . 1.519(3) yes
C16 . H162 . 0.967 no
C16 . H161 . 0.956 no
N17 . C18 . 1.499(3) yes
N17 . C22 . 1.484(4) yes
N17 . H171 . 0.898(17) no
C18 . C19 . 1.523(4) yes
C18 . H181 . 0.952 no
C18 . H182 . 0.968 no
C19 . N20 . 1.465(4) yes
C19 . H191 . 0.967 no
C19 . H192 . 0.985 no
N20 . C21 . 1.466(3) yes
N20 . C23 . 1.398(3) yes
C21 . C22 . 1.525(3) yes
C21 . H211 . 0.987 no
C21 . H212 . 0.991 no
C22 . H221 . 0.959 no
C22 . H222 . 0.987 no
C23 . C24 . 1.406(4) yes
C23 . C61 . 1.405(4) yes
C24 . C25 . 1.382(4) yes
C24 . H241 . 0.951 no
C25 . O26 . 1.386(3) yes
C25 . C36 . 1.407(3) yes
O26 . C27 . 1.389(3) yes
C27 . C28 . 1.386(4) yes
C27 . C35 . 1.379(4) yes
C28 . C29 . 1.398(4) yes
C28 . H281 . 0.922 no
C29 . C30 . 1.415(4) yes
C29 . C33 . 1.432(3) yes
C30 . N31 . 1.349(3) yes
C30 . N34 . 1.344(3) yes
N31 . C32 . 1.390(4) yes
N31 . H311 . 0.857(17) no
C32 . C33 . 1.357(4) yes
C32 . H321 . 0.926 no
C33 . H331 . 0.945 no
N34 . C35 . 1.350(3) yes
N34 . H341 . 0.861(17) no
C35 . H351 . 0.918 no
C36 . C37 . 1.496(3) yes
C36 . C60 . 1.393(4) yes
C37 . O38 . 1.224(3) yes
C37 . N39 . 1.367(4) yes
N39 . S40 . 1.664(2) yes
N39 . H391 . 0.852(17) no
S40 . O41 . 1.425(2) yes
S40 . O42 . 1.429(2) yes
S40 . C43 . 1.753(3) yes
C43 . C44 . 1.402(4) yes
C43 . C56 . 1.375(4) yes
C44 . C45 . 1.376(4) yes
C44 . H441 . 0.947 no
C45 . C46 . 1.423(4) yes
C45 . H451 . 0.915 no
C46 . N47 . 1.345(3) yes
C46 . C55 . 1.422(4) yes
N47 . C48 . 1.458(4) yes
N47 . H471 . 0.848(17) no
C48 . C49 . 1.530(4) yes
C48 . H482 . 0.957 no
C48 . H481 . 0.959 no
C49 . C50 . 1.525(4) yes
C49 . C54 . 1.528(4) yes
C49 . H491 . 0.979 no
C50 . C51 . 1.516(4) yes
C50 . H501 . 0.987 no
C50 . H502 . 0.956 no
C51 . O52 . 1.442(4) yes
C51 . H511 . 0.976 no
C51 . H512 . 0.984 no
O52 . C53 . 1.425(4) yes
C53 . C54 . 1.522(4) yes
C53 . H531 . 0.999 no
C53 . H532 . 0.964 no
C54 . H541 . 0.969 no
C54 . H542 . 0.976 no
C55 . C56 . 1.399(4) yes
C55 . N57 . 1.451(3) yes
C56 . H561 . 0.924 no
N57 . O58 . 1.222(3) yes
N57 . O59 . 1.242(3) yes
C60 . C61 . 1.385(4) yes
C60 . H601 . 0.943 no
C61 . H611 . 0.933 no
S62 . O63 . 1.432(2) yes
S62 . O64 . 1.475(2) yes
S62 . O65 . 1.465(2) yes
S62 . C66 . 1.773(3) yes
C66 . C67 . 1.421(4) yes
C66 . C71 . 1.361(4) yes
C67 . C68 . 1.372(5) yes
C67 . H671 . 0.920 no
C68 . C69 . 1.415(4) yes
C68 . H681 . 0.927 no
C69 . C70 . 1.424(4) yes
C69 . C75 . 1.417(4) yes
C70 . C71 . 1.424(4) yes
C70 . C72 . 1.414(5) yes
C71 . H711 . 0.922 no
C72 . C73 . 1.380(5) yes
C72 . H721 . 0.935 no
C73 . C74 . 1.404(6) yes
C73 . H731 . 0.935 no
C74 . C75 . 1.358(5) yes
C74 . H741 . 0.955 no
C75 . H751 . 0.961 no
S76 . O77 . 1.467(2) yes
S76 . O78 . 1.447(2) yes
S76 . O79 . 1.457(2) yes
S76 . C80 . 1.778(3) yes
C80 . C81 . 1.409(4) yes
C80 . C85 . 1.370(4) yes
C81 . C82 . 1.373(4) yes
C81 . H811 . 0.962 no
C82 . C83 . 1.398(5) yes
C82 . H821 . 0.967 no
C83 . C84 . 1.428(5) yes
C83 . C89 . 1.434(5) yes
C84 . C85 . 1.421(5) yes
C84 . C86 . 1.416(5) yes
C85 . H851 . 0.950 no
C86 . C87 . 1.365(6) yes
C86 . H861 . 0.937 no
C87 . C88 . 1.405(8) yes
C87 . H871 . 0.956 no
C88 . C89 . 1.363(7) yes
C88 . H881 . 0.938 no
C89 . H891 . 0.970 no
N90 . C91 . 1.120(12) yes
C91 . C92 . 1.439(10) yes
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 . 119.5(2) yes
Cl1 . C2 . C7 . 118.3(2) yes
C3 . C2 . C7 . 122.1(3) yes
C2 . C3 . C4 . 118.9(3) yes
C2 . C3 . H31 . 121.4 no
C4 . C3 . H31 . 119.8 no
C3 . C4 . C5 . 120.9(3) yes
C3 . C4 . H41 . 119.2 no
C5 . C4 . H41 . 119.8 no
C4 . C5 . C6 . 118.9(2) yes
C4 . C5 . C8 . 120.5(2) yes
C6 . C5 . C8 . 120.5(2) yes
C5 . C6 . C7 . 120.7(2) yes
C5 . C6 . H61 . 119.1 no
C7 . C6 . H61 . 120.2 no
C6 . C7 . C2 . 118.5(3) yes
C6 . C7 . H71 . 122.3 no
C2 . C7 . H71 . 119.2 no
C5 . C8 . C9 . 123.1(3) yes
C5 . C8 . C13 . 114.2(2) yes
C9 . C8 . C13 . 122.7(2) yes
C8 . C9 . C10 . 121.7(3) yes
C8 . C9 . C16 . 122.8(2) yes
C10 . C9 . C16 . 115.5(2) yes
C9 . C10 . C11 . 113.0(2) yes
C9 . C10 . H101 . 106.5 no
C11 . C10 . H101 . 107.8 no
C9 . C10 . H102 . 111.5 no
C11 . C10 . H102 . 109.7 no
H101 . C10 . H102 . 108.1 no
C10 . C11 . C12 . 111.9(2) yes
C10 . C11 . H111 . 108.3 no
C12 . C11 . H111 . 108.1 no
C10 . C11 . H112 . 109.6 no
C12 . C11 . H112 . 110.8 no
H111 . C11 . H112 . 108.0 no
C11 . C12 . C13 . 107.6(2) yes
C11 . C12 . C14 . 110.0(2) yes
C13 . C12 . C14 . 109.5(2) yes
C11 . C12 . C15 . 110.8(2) yes
C13 . C12 . C15 . 110.4(2) yes
C14 . C12 . C15 . 108.5(3) yes
C12 . C13 . C8 . 115.0(2) yes
C12 . C13 . H131 . 109.6 no
C8 . C13 . H131 . 106.9 no
C12 . C13 . H132 . 108.8 no
C8 . C13 . H132 . 106.9 no
H131 . C13 . H132 . 109.4 no
C12 . C14 . H141 . 113.8 no
C12 . C14 . H142 . 107.8 no
H141 . C14 . H142 . 103.9 no
C12 . C14 . H143 . 113.9 no
H141 . C14 . H143 . 110.1 no
H142 . C14 . H143 . 106.6 no
C12 . C15 . H151 . 108.7 no
C12 . C15 . H152 . 109.5 no
H151 . C15 . H152 . 110.8 no
C12 . C15 . H153 . 107.0 no
H151 . C15 . H153 . 111.7 no
H152 . C15 . H153 . 109.0 no
C9 . C16 . N17 . 112.3(2) yes
C9 . C16 . H162 . 110.5 no
N17 . C16 . H162 . 109.8 no
C9 . C16 . H161 . 108.7 no
N17 . C16 . H161 . 105.7 no
H162 . C16 . H161 . 109.6 no
C16 . N17 . C18 . 112.25(19) yes
C16 . N17 . C22 . 110.5(2) yes
C18 . N17 . C22 . 108.0(2) yes
C16 . N17 . H171 . 108.5(13) no
C18 . N17 . H171 . 108.1(13) no
C22 . N17 . H171 . 109.5(13) no
N17 . C18 . C19 . 110.3(2) yes
N17 . C18 . H181 . 108.5 no
C19 . C18 . H181 . 110.4 no
N17 . C18 . H182 . 107.6 no
C19 . C18 . H182 . 111.1 no
H181 . C18 . H182 . 108.9 no
C18 . C19 . N20 . 113.0(2) yes
C18 . C19 . H191 . 109.8 no
N20 . C19 . H191 . 108.6 no
C18 . C19 . H192 . 107.9 no
N20 . C19 . H192 . 108.3 no
H191 . C19 . H192 . 109.2 no
C19 . N20 . C21 . 116.9(2) yes
C19 . N20 . C23 . 115.7(2) yes
C21 . N20 . C23 . 116.3(2) yes
N20 . C21 . C22 . 112.4(2) yes
N20 . C21 . H211 . 109.2 no
C22 . C21 . H211 . 110.6 no
N20 . C21 . H212 . 106.1 no
C22 . C21 . H212 . 108.0 no
H211 . C21 . H212 . 110.3 no
C21 . C22 . N17 . 111.7(2) yes
C21 . C22 . H221 . 107.8 no
N17 . C22 . H221 . 110.4 no
C21 . C22 . H222 . 108.5 no
N17 . C22 . H222 . 109.3 no
H221 . C22 . H222 . 109.1 no
N20 . C23 . C24 . 120.7(2) yes
N20 . C23 . C61 . 121.3(2) yes
C24 . C23 . C61 . 118.0(2) yes
C23 . C24 . C25 . 120.7(2) yes
C23 . C24 . H241 . 119.4 no
C25 . C24 . H241 . 119.9 no
C24 . C25 . O26 . 121.1(2) yes
C24 . C25 . C36 . 122.1(3) yes
O26 . C25 . C36 . 116.6(2) yes
C25 . O26 . C27 . 118.6(2) yes
O26 . C27 . C28 . 118.7(2) yes
O26 . C27 . C35 . 119.0(2) yes
C28 . C27 . C35 . 122.2(2) yes
C27 . C28 . C29 . 117.6(2) yes
C27 . C28 . H281 . 119.9 no
C29 . C28 . H281 . 122.4 no
C28 . C29 . C30 . 117.9(2) yes
C28 . C29 . C33 . 136.7(3) yes
C30 . C29 . C33 . 105.4(2) yes
C29 . C30 . N31 . 110.0(2) yes
C29 . C30 . N34 . 122.6(2) yes
N31 . C30 . N34 . 127.3(3) yes
C30 . N31 . C32 . 107.0(2) yes
C30 . N31 . H311 . 125.7(12) no
C32 . N31 . H311 . 127.2(12) no
N31 . C32 . C33 . 110.7(2) yes
N31 . C32 . H321 . 124.5 no
C33 . C32 . H321 . 124.8 no
C29 . C33 . C32 . 106.8(2) yes
C29 . C33 . H331 . 126.3 no
C32 . C33 . H331 . 126.9 no
C30 . N34 . C35 . 119.4(2) yes
C30 . N34 . H341 . 121.3(12) no
C35 . N34 . H341 . 119.3(12) no
C27 . C35 . N34 . 120.1(2) yes
C27 . C35 . H351 . 119.7 no
N34 . C35 . H351 . 120.2 no
C25 . C36 . C37 . 126.6(3) yes
C25 . C36 . C60 . 116.2(2) yes
C37 . C36 . C60 . 117.1(2) yes
C36 . C37 . O38 . 120.6(3) yes
C36 . C37 . N39 . 118.5(2) yes
O38 . C37 . N39 . 120.9(2) yes
C37 . N39 . S40 . 122.45(19) yes
C37 . N39 . H391 . 121.0(12) no
S40 . N39 . H391 . 116.4(12) no
N39 . S40 . O41 . 103.36(12) yes
N39 . S40 . O42 . 108.99(12) yes
O41 . S40 . O42 . 120.06(12) yes
N39 . S40 . C43 . 107.27(12) yes
O41 . S40 . C43 . 108.56(13) yes
O42 . S40 . C43 . 107.94(12) yes
S40 . C43 . C44 . 119.9(2) yes
S40 . C43 . C56 . 119.3(2) yes
C44 . C43 . C56 . 120.6(2) yes
C43 . C44 . C45 . 120.1(3) yes
C43 . C44 . H441 . 121.6 no
C45 . C44 . H441 . 118.2 no
C44 . C45 . C46 . 122.0(3) yes
C44 . C45 . H451 . 118.9 no
C46 . C45 . H451 . 119.1 no
C45 . C46 . N47 . 120.2(2) yes
C45 . C46 . C55 . 115.5(2) yes
N47 . C46 . C55 . 124.3(3) yes
C46 . N47 . C48 . 124.2(2) yes
C46 . N47 . H471 . 117.5(12) no
C48 . N47 . H471 . 118.3(12) no
N47 . C48 . C49 . 112.9(2) yes
N47 . C48 . H482 . 107.7 no
C49 . C48 . H482 . 109.1 no
N47 . C48 . H481 . 110.3 no
C49 . C48 . H481 . 108.7 no
H482 . C48 . H481 . 108.0 no
C48 . C49 . C50 . 111.1(2) yes
C48 . C49 . C54 . 111.0(2) yes
C50 . C49 . C54 . 109.4(2) yes
C48 . C49 . H491 . 108.2 no
C50 . C49 . H491 . 109.2 no
C54 . C49 . H491 . 107.9 no
C49 . C50 . C51 . 110.1(2) yes
C49 . C50 . H501 . 111.9 no
C51 . C50 . H501 . 109.6 no
C49 . C50 . H502 . 108.7 no
C51 . C50 . H502 . 109.0 no
H501 . C50 . H502 . 107.4 no
C50 . C51 . O52 . 110.6(2) yes
C50 . C51 . H511 . 107.7 no
O52 . C51 . H511 . 110.0 no
C50 . C51 . H512 . 109.0 no
O52 . C51 . H512 . 109.2 no
H511 . C51 . H512 . 110.4 no
C51 . O52 . C53 . 111.0(2) yes
O52 . C53 . C54 . 112.4(3) yes
O52 . C53 . H531 . 109.3 no
C54 . C53 . H531 . 106.3 no
O52 . C53 . H532 . 107.0 no
C54 . C53 . H532 . 110.7 no
H531 . C53 . H532 . 111.2 no
C49 . C54 . C53 . 111.0(2) yes
C49 . C54 . H541 . 108.3 no
C53 . C54 . H541 . 112.1 no
C49 . C54 . H542 . 106.9 no
C53 . C54 . H542 . 108.5 no
H541 . C54 . H542 . 109.9 no
C46 . C55 . C56 . 122.6(2) yes
C46 . C55 . N57 . 121.7(2) yes
C56 . C55 . N57 . 115.6(2) yes
C55 . C56 . C43 . 119.0(2) yes
C55 . C56 . H561 . 119.8 no
C43 . C56 . H561 . 121.1 no
C55 . N57 . O58 . 119.3(2) yes
C55 . N57 . O59 . 118.9(2) yes
O58 . N57 . O59 . 121.8(2) yes
C36 . C60 . C61 . 123.0(2) yes
C36 . C60 . H601 . 119.9 no
C61 . C60 . H601 . 117.1 no
C23 . C61 . C60 . 120.0(2) yes
C23 . C61 . H611 . 119.9 no
C60 . C61 . H611 . 120.1 no
O63 . S62 . O64 . 113.09(13) yes
O63 . S62 . O65 . 114.75(12) yes
O64 . S62 . O65 . 111.04(12) yes
O63 . S62 . C66 . 106.68(13) yes
O64 . S62 . C66 . 104.22(12) yes
O65 . S62 . C66 . 106.14(13) yes
S62 . C66 . C67 . 119.0(2) yes
S62 . C66 . C71 . 119.6(2) yes
C67 . C66 . C71 . 121.3(3) yes
C66 . C67 . C68 . 119.3(3) yes
C66 . C67 . H671 . 121.6 no
C68 . C67 . H671 . 119.1 no
C67 . C68 . C69 . 121.0(3) yes
C67 . C68 . H681 . 119.1 no
C69 . C68 . H681 . 119.9 no
C68 . C69 . C70 . 119.4(3) yes
C68 . C69 . C75 . 122.2(3) yes
C70 . C69 . C75 . 118.4(3) yes
C69 . C70 . C71 . 118.5(3) yes
C69 . C70 . C72 . 119.3(3) yes
C71 . C70 . C72 . 122.2(3) yes
C70 . C71 . C66 . 120.4(3) yes
C70 . C71 . H711 . 120.5 no
C66 . C71 . H711 . 119.1 no
C70 . C72 . C73 . 120.3(3) yes
C70 . C72 . H721 . 120.9 no
C73 . C72 . H721 . 118.8 no
C72 . C73 . C74 . 120.1(4) yes
C72 . C73 . H731 . 120.3 no
C74 . C73 . H731 . 119.6 no
C73 . C74 . C75 . 120.7(3) yes
C73 . C74 . H741 . 120.7 no
C75 . C74 . H741 . 118.6 no
C69 . C75 . C74 . 121.1(3) yes
C69 . C75 . H751 . 119.6 no
C74 . C75 . H751 . 119.3 no
O77 . S76 . O78 . 113.04(13) yes
O77 . S76 . O79 . 111.31(12) yes
O78 . S76 . O79 . 113.22(15) yes
O77 . S76 . C80 . 105.81(13) yes
O78 . S76 . C80 . 107.57(14) yes
O79 . S76 . C80 . 105.23(13) yes
S76 . C80 . C81 . 120.3(2) yes
S76 . C80 . C85 . 118.0(2) yes
C81 . C80 . C85 . 121.5(3) yes
C80 . C81 . C82 . 119.7(3) yes
C80 . C81 . H811 . 120.2 no
C82 . C81 . H811 . 120.1 no
C81 . C82 . C83 . 120.5(3) yes
C81 . C82 . H821 . 119.0 no
C83 . C82 . H821 . 120.5 no
C82 . C83 . C84 . 119.9(3) yes
C82 . C83 . C89 . 122.2(3) yes
C84 . C83 . C89 . 117.9(4) yes
C83 . C84 . C85 . 118.6(3) yes
C83 . C84 . C86 . 119.8(3) yes
C85 . C84 . C86 . 121.4(3) yes
C84 . C85 . C80 . 119.6(3) yes
C84 . C85 . H851 . 119.0 no
C80 . C85 . H851 . 121.5 no
C84 . C86 . C87 . 120.6(4) yes
C84 . C86 . H861 . 119.6 no
C87 . C86 . H861 . 119.8 no
C86 . C87 . C88 . 119.8(4) yes
C86 . C87 . H871 . 119.0 no
C88 . C87 . H871 . 121.2 no
C87 . C88 . C89 . 121.9(4) yes
C87 . C88 . H881 . 119.2 no
C89 . C88 . H881 . 118.9 no
C83 . C89 . C88 . 119.9(4) yes
C83 . C89 . H891 . 117.9 no
C88 . C89 . H891 . 122.1 no
N90 . C91 . C92 . 178.6(9) yes
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
C6 . H61 . O52 1_666 152 0.92 2.49 3.335(5) yes
C33 . H331 . O38 1_565 146 0.94 2.44 3.270(5) yes
N31 . H311 . O65 1_465 154(2) 0.857(17) 1.973(19) 2.767(5) yes
N34 . H341 . O64 1_465 165(3) 0.861(17) 1.787(19) 2.628(5) yes
C48 . H481 . O41 1_545 150 0.96 2.57 3.432(5) yes
N47 . H471 . O59 . 130.6(16) 0.848(17) 2.002(18) 2.634(5) yes
C56 . H561 . O78 1_455 156 0.92 2.42 3.287(5) yes
N39 . H391 . O79 1_455 160.4(18) 0.852(17) 2.062(18) 2.879(5) yes
C19 . H191 . O78 . 164 0.97 2.41 3.347(5) yes
N17 . H171 . O77 . 160.9(19) 0.898(17) 1.891(18) 2.755(5) yes
C4 . H41 . O63 . 132 0.92 2.43 3.123(5) yes
C85 . H851 . O59 1_665 155 0.95 2.54 3.428(5) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_systematic        Venetoclax
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2393682'
loop_
_audit_author_name
_audit_author_address
'Eliska Zmeskalova'
;Institute of Physics of the Czech Academy of Sciences
Czech Republic
;
_audit_update_record             
;
2024-10-25 deposited with the CCDC.	2025-02-12 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   12.19350(10)
_cell_length_b                   15.73850(10)
_cell_length_c                   17.4811(2)
_cell_angle_alpha                109.4801(9)
_cell_angle_beta                 95.9264(8)
_cell_angle_gamma                109.2612(9)
_cell_volume                     2898.70(5)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

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'


_cell_formula_units_Z            2

# Given Formula = C52 H58 Cl1 N7 O10 S2 
# Dc =      1.19 Fooo =   1096.00 Mu =     17.35 M =   1040.66
# Found Formula = C59 H66 Cl1 N7 O13 S3 
# Dc =      1.39 FOOO =   1276.00 Mu =     21.84 M =   1212.86

_chemical_formula_sum            'C59 H66 Cl1 N7 O13 S3'
_chemical_formula_moiety         'C59 H66 Cl1 N7 O13 S3'
_chemical_compound_source        ?
_chemical_formula_weight         1212.86


_cell_measurement_reflns_used    58145
_cell_measurement_theta_min      3
_cell_measurement_theta_max      73
_cell_measurement_temperature    95

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.099
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_max          0.156

_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1276
_exptl_absorpt_coefficient_mu    2.184

# Sheldrick geometric approximatio 0.74 0.81 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.81
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      95
_diffrn_reflns_number            100705
_reflns_number_total             11510
_diffrn_reflns_av_R_equivalents  0.045
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 11510 
# Theoretical number of reflections is about 23347 


_diffrn_reflns_theta_min         2.762
_diffrn_reflns_theta_max         73.465
_diffrn_measured_fraction_theta_max 0.986

_diffrn_reflns_theta_full        69.792
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -15
_reflns_limit_h_max              14
_reflns_limit_k_min              -19
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   1.45
_oxford_diffrn_Wilson_scale      0.05

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.75
_refine_diff_density_max         0.71


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     21
_refine_ls_number_parameters     768
_refine_ls_number_reflns         11458
_oxford_refine_ls_R_factor_ref   0.0510
_refine_ls_wR_factor_ref         0.1374
_refine_ls_goodness_of_fit_ref   0.9078
_refine_ls_shift/su_max          0.0006019
_refine_ls_shift/su_mean         0.0000321


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        11466
_refine_ls_R_factor_all          0.0511
_refine_ls_wR_factor_all         0.1379

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                10350
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_gt          0.1351


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.00P)² +18.96P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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 . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.13(4)
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_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_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



# Manually omitted reflections

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 .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_systematic        Venetoclax
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
