# 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_APR_2ClBA
_database_code_depnum_ccdc_archive 'CCDC 2477189'
loop_
_audit_author_name
_audit_author_address
'Yelizaveta Naumkina'
;University of Chemistry and Technology Prague
Czech Republic
;
_audit_update_record             
;
2025-07-30 deposited with the CCDC.	2025-10-13 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. 
;


#--------------------------------------------------------------- 
# _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                   13.0114(3)
_cell_length_b                   13.0114(3)
_cell_length_c                   29.2398(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4950.2(3)

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 41 21 2 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-y+1/2,x+1/2,z+1/4
-x,-y,z+1/2
y+1/2,-x+1/2,z+3/4
-x+1/2,y+1/2,-z+1/4
y,x,-z
x+1/2,-y+1/2,-z+3/4
-y,-x,-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'
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            8

# Given Formula = C25.50 H26.50 Cl0.50 N2 O8 S1 
# Dc =      1.45 Fooo =   2256.00 Mu =     21.30 M =    538.79
# Found Formula = C25.50 H26.50 Cl0.50 N2 O8 S1 
# Dc =      1.45 FOOO =   2256.00 Mu =     21.30 M =    538.79

_chemical_formula_sum            'C25.50 H26.50 Cl0.50 N2 O8 S'
_chemical_formula_moiety         'C22 H24 N2 O7 S, 1/2(C7 H5 Cl O2)'
_chemical_compound_source        .
_chemical_formula_weight         538.79


_cell_measurement_reflns_used    9514
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      72.17
_cell_measurement_temperature    180

_exptl_crystal_description       bipyramidal
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.192
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_max          0.218

_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2256
_exptl_absorpt_coefficient_mu    2.130

# Sheldrick geometric approximatio 0.63 0.66 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.66
_diffrn_measurement_device_type  'Bruker Venture D8'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  polycapillary
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_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      180
_diffrn_reflns_number            4882
_diffrn_reflns_av_unetI/netI     0.017
_reflns_number_total             4882
_diffrn_reflns_av_R_equivalents  0.0492
# Number of reflections without Friedels Law is 4882 
# Number of reflections with Friedels Law is 2863 
# Theoretical number of reflections is about 2440 


_diffrn_reflns_theta_min         3.718
_diffrn_reflns_theta_max         72.167
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        72.167
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       36
_reflns_limit_h_min              -10
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              36

_oxford_diffrn_Wilson_B_factor   3.04
_oxford_diffrn_Wilson_scale      150.65

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

_refine_diff_density_min         -0.43
_refine_diff_density_max         0.84


# 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     150
_refine_ls_number_parameters     388
_refine_ls_number_reflns         4882
_refine_ls_R_factor_ref          0.0460
_refine_ls_wR_factor_ref         0.1304
_refine_ls_goodness_of_fit_ref   0.9999
_refine_ls_shift/su_max          0.0010984
_refine_ls_shift/su_mean         0.0000721


# Computed with I/sigma = -10 
_reflns_number_all               4882
_refine_ls_R_factor_all          0.0460
_refine_ls_wR_factor_all         0.1304

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4812
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_gt          0.1300

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  -0.0002(17) # for 1782 Friedel pairs 
_oxford_Bijvoet_difference       -0.002(4) # for 1782 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          -0.00(2) # for 2019 Friedel pairs 
_refine_ls_abs_structure_Flack   -0.002(4)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 1782 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) + ( 0.09P)² + 4.15P] 
 ,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
S1 S 0.59477(5) 0.16493(5) 0.28440(2) 0.0321 1.0000 Uani . . . . . .
N1 N 0.53674(16) 0.34400(16) 0.35425(7) 0.0283 1.0000 Uani . . . . . .
N2 N 0.68225(18) 0.29009(18) 0.48524(7) 0.0340 1.0000 Uani D . . . . .
C1 C 0.7113(2) 0.3616(2) 0.45219(8) 0.0308 1.0000 Uani D . . . . .
C2 C 0.7923(2) 0.4318(2) 0.45670(10) 0.0395 1.0000 Uani . . . . . .
C3 C 0.8136(2) 0.5024(2) 0.42207(12) 0.0465 1.0000 Uani . . . . . .
C4 C 0.7562(2) 0.5086(2) 0.38229(10) 0.0399 1.0000 Uani . . . . . .
C5 C 0.6769(2) 0.43903(19) 0.37813(8) 0.0313 1.0000 Uani . . . . . .
C6 C 0.6005(2) 0.42487(19) 0.34090(8) 0.0304 1.0000 Uani . . . . . .
C7 C 0.56570(19) 0.30540(19) 0.39702(8) 0.0287 1.0000 Uani . . . . . .
C8 C 0.65531(19) 0.36676(19) 0.41198(8) 0.0278 1.0000 Uani . . . . . .
C9 C 0.7242(2) 0.2732(2) 0.52770(9) 0.0364 1.0000 Uani D . . . . .
C10 C 0.6641(3) 0.1987(3) 0.55641(10) 0.0464 1.0000 Uani . . . . . .
C11 C 0.45663(19) 0.29694(19) 0.32568(8) 0.0286 1.0000 Uani . . . . . .
C12 C 0.49940(19) 0.2613(2) 0.27948(8) 0.0305 1.0000 Uani . . . . . .
C13 C 0.6175(3) 0.1319(3) 0.22703(11) 0.0491 1.0000 Uani . . . . . .
C14 C 0.36446(19) 0.36814(19) 0.31906(9) 0.0300 1.0000 Uani . . . . . .
C15 C 0.2932(2) 0.3749(2) 0.35387(9) 0.0342 1.0000 Uani . . . . . .
C16 C 0.2071(2) 0.4385(2) 0.34978(9) 0.0348 1.0000 Uani . . . . . .
C17 C 0.1913(2) 0.4938(2) 0.30993(10) 0.0364 1.0000 Uani . . . . . .
C18 C 0.2631(2) 0.4876(2) 0.27424(9) 0.0369 1.0000 Uani . . . . . .
C19 C 0.3492(2) 0.4247(2) 0.27889(9) 0.0343 1.0000 Uani . . . . . .
C20 C 0.0359(2) 0.5658(3) 0.33833(11) 0.0460 1.0000 Uani . . . . . .
C21 C 0.3172(2) 0.5455(3) 0.20027(11) 0.0465 1.0000 Uani . . . . . .
C22 C 0.2856(3) 0.6262(4) 0.16586(14) 0.0715 1.0000 Uani . . . . . .
O1 O 0.59224(16) 0.47175(14) 0.30529(6) 0.0373 1.0000 Uani . . . . . .
O2 O 0.52294(15) 0.23467(15) 0.41669(6) 0.0358 1.0000 Uani . . . . . .
O3 O 0.80173(17) 0.31611(18) 0.54099(7) 0.0460 1.0000 Uani . . . . . .
O4 O 0.68715(15) 0.20993(17) 0.30268(7) 0.0421 1.0000 Uani . . . . . .
O5 O 0.55255(17) 0.07776(16) 0.30802(8) 0.0452 1.0000 Uani . . . . . .
O6 O 0.10917(16) 0.55698(17) 0.30218(8) 0.0481 1.0000 Uani . . . . . .
O7 O 0.24231(16) 0.54595(18) 0.23625(7) 0.0497 1.0000 Uani . . . . . .
H21 H 0.8333 0.4316 0.4821 0.0477 1.0000 Uiso R . . . . .
H22 H 0.637(2) 0.2487(19) 0.4763(7) 0.041(2) 1.0000 Uiso D . . . . .
H31 H 0.8687 0.5497 0.4268 0.0555 1.0000 Uiso R . . . . .
H41 H 0.7677 0.5555 0.3608 0.0483 1.0000 Uiso R . . . . .
H101 H 0.6027 0.2362 0.5658 0.0680 1.0000 Uiso R . . . . .
H102 H 0.7101 0.1822 0.5823 0.0689 1.0000 Uiso R . . . . .
H103 H 0.6462 0.1403 0.5375 0.0677 1.0000 Uiso R . . . . .
H111 H 0.4354 0.2396 0.3433 0.0333 1.0000 Uiso R . . . . .
H121 H 0.5292 0.3167 0.2612 0.0383 1.0000 Uiso R . . . . .
H122 H 0.4431 0.2280 0.2629 0.0381 1.0000 Uiso R . . . . .
H131 H 0.6636 0.0779 0.2232 0.0725 1.0000 Uiso R . . . . .
H132 H 0.6394 0.1913 0.2103 0.0725 1.0000 Uiso R . . . . .
H133 H 0.5530 0.1078 0.2151 0.0710 1.0000 Uiso R . . . . .
H151 H 0.3053 0.3371 0.3812 0.0408 1.0000 Uiso R . . . . .
H161 H 0.1608 0.4437 0.3733 0.0400 1.0000 Uiso R . . . . .
H191 H 0.3970 0.4197 0.2566 0.0399 1.0000 Uiso R . . . . .
H201 H -0.0157 0.6133 0.3275 0.0687 1.0000 Uiso R . . . . .
H202 H 0.0051 0.4981 0.3435 0.0687 1.0000 Uiso R . . . . .
H203 H 0.0689 0.5935 0.3661 0.0683 1.0000 Uiso R . . . . .
H211 H 0.3206 0.4780 0.1849 0.0548 1.0000 Uiso R . . . . .
H212 H 0.3812 0.5645 0.2138 0.0538 1.0000 Uiso R . . . . .
H221 H 0.3335 0.6311 0.1402 0.1059 1.0000 Uiso R . . . . .
H222 H 0.2188 0.6090 0.1536 0.1062 1.0000 Uiso R . . . . .
H223 H 0.2814 0.6938 0.1807 0.1055 1.0000 Uiso R . . . . .
C61 C 0.5448(12) 0.5800(9) 0.4771(8) 0.0682 0.5000 Uani D . . . . .
C66 C 0.5372(12) 0.5692(10) 0.4790(8) 0.0703 0.5000 Uani D . . . . .
C62 C 0.4654(12) 0.5346(9) 0.4531(6) 0.0840 0.5000 Uani D . . . . .
C64 C 0.4153(10) 0.4353(9) 0.4858(5) 0.0772 0.5000 Uani D . . . . .
C63 C 0.4113(11) 0.4518(9) 0.4730(5) 0.0805 0.5000 Uani D . . . . .
C65 C 0.4559(12) 0.5153(8) 0.4593(6) 0.0770 0.5000 Uani D . . . . .
C67 C 0.6017(9) 0.6701(8) 0.4576(3) 0.0923 0.5000 Uani D U . . . .
O68 O 0.5803(7) 0.6883(6) 0.4166(3) 0.1026 0.5000 Uani D . . . . .
O69 O 0.6248(5) 0.7429(5) 0.4866(2) 0.0790 0.5000 Uani D . . . . .
Cl1 Cl 0.5857(2) 0.6694(2) 0.44687(12) 0.0831 0.5000 Uani D U . . . .
H691 H 0.629(9) 0.827(10) 0.470(4) 0.119(2) 0.5000 Uiso . . . . . .
H621 H 0.4469 0.5590 0.4237 0.0991 0.5000 Uiso R . . . . .
H631 H 0.3586 0.4204 0.4587 0.0957 0.5000 Uiso R . . . . .
H641 H 0.3592 0.3972 0.4738 0.0885 0.5000 Uiso R . . . . .
H651 H 0.4297 0.5319 0.4293 0.0901 0.5000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2903(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
S1 . C12 . 1.770(2) yes
S1 . C13 . 1.756(3) yes
S1 . O4 . 1.440(2) yes
S1 . O5 . 1.437(2) yes
N1 . C6 . 1.395(3) yes
N1 . C7 . 1.399(3) yes
N1 . C11 . 1.469(3) yes
N2 . C1 . 1.394(3) yes
N2 . C9 . 1.374(3) yes
N2 . H22 . 0.837(18) no
C1 . C2 . 1.401(4) yes
C1 . C8 . 1.385(4) yes
C2 . C3 . 1.396(4) yes
C2 . H21 . 0.915 no
C3 . C4 . 1.385(4) yes
C3 . H31 . 0.954 no
C4 . C5 . 1.377(4) yes
C4 . H41 . 0.889 no
C5 . C6 . 1.486(4) yes
C5 . C8 . 1.394(3) yes
C6 . O1 . 1.212(3) yes
C7 . C8 . 1.479(4) yes
C7 . O2 . 1.220(3) yes
C9 . C10 . 1.503(4) yes
C9 . O3 . 1.216(4) yes
C10 . H101 . 0.975 no
C10 . H102 . 0.990 no
C10 . H103 . 0.967 no
C11 . C12 . 1.533(3) yes
C11 . C14 . 1.528(3) yes
C11 . H111 . 0.949 no
C12 . H121 . 0.977 no
C12 . H122 . 0.979 no
C13 . H131 . 0.931 no
C13 . H132 . 0.957 no
C13 . H133 . 0.963 no
C14 . C15 . 1.379(4) yes
C14 . C19 . 1.400(4) yes
C15 . C16 . 1.398(4) yes
C15 . H151 . 0.952 no
C16 . C17 . 1.385(4) yes
C16 . H161 . 0.916 no
C17 . C18 . 1.403(4) yes
C17 . O6 . 1.367(3) yes
C18 . C19 . 1.394(4) yes
C18 . O7 . 1.373(3) yes
C19 . H191 . 0.903 no
C20 . O6 . 1.428(3) yes
C20 . H201 . 0.966 no
C20 . H202 . 0.981 no
C20 . H203 . 0.987 no
C21 . C22 . 1.512(4) yes
C21 . O7 . 1.434(3) yes
C21 . H211 . 0.988 no
C21 . H212 . 0.955 no
C22 . H221 . 0.978 no
C22 . H222 . 0.967 no
C22 . H223 . 0.982 no
C61 . C61 6_556 1.49(5) yes
C61 . C66 6_556 1.435(10) yes
C61 . C62 . 1.382(9) yes
C61 . C65 . 1.52(4) yes
C61 . C67 . 1.499(9) yes
C61 . Cl1 . 1.554(17) yes
C66 . C66 6_556 1.36(5) yes
C66 . C62 . 1.28(4) yes
C66 . C65 . 1.393(9) yes
C66 . C67 . 1.68(2) yes
C66 . Cl1 . 1.726(17) yes
C62 . C64 . 1.73(2) yes
C62 . C63 . 1.412(9) yes
C62 . H621 . 0.947 no
C62 . H651 . 0.838 no
C64 . C63 6_556 1.332(14) yes
C64 . C64 6_556 0.91(3) yes
C64 . C65 . 1.402(8) yes
C64 . H631 . 1.100 no
C64 . H641 . 0.950 no
C63 . C63 6_556 1.75(4) yes
C63 . C65 . 1.09(2) yes
C63 . H631 . 0.899 no
C63 . H641 . 0.981 no
C65 . H621 . 1.190 no
C65 . H651 . 0.965 no
C67 . O68 . 1.253(7) yes
C67 . O69 . 1.307(6) yes
O69 . Cl1 . 1.589(7) yes
O69 . H691 . 1.19(13) no
H621 . H651 . 0.449 no
H631 . H641 . 0.533 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
C12 . S1 . C13 . 102.34(14) yes
C12 . S1 . O4 . 109.11(13) yes
C13 . S1 . O4 . 108.25(15) yes
C12 . S1 . O5 . 109.27(13) yes
C13 . S1 . O5 . 109.30(16) yes
O4 . S1 . O5 . 117.49(13) yes
C6 . N1 . C7 . 111.1(2) yes
C6 . N1 . C11 . 125.2(2) yes
C7 . N1 . C11 . 123.3(2) yes
C1 . N2 . C9 . 128.7(2) yes
C1 . N2 . H22 . 113.7(12) no
C9 . N2 . H22 . 117.3(12) no
N2 . C1 . C2 . 125.0(2) yes
N2 . C1 . C8 . 118.6(2) yes
C2 . C1 . C8 . 116.4(2) yes
C1 . C2 . C3 . 120.7(3) yes
C1 . C2 . H21 . 120.9 no
C3 . C2 . H21 . 118.4 no
C2 . C3 . C4 . 122.7(3) yes
C2 . C3 . H31 . 118.0 no
C4 . C3 . H31 . 119.3 no
C3 . C4 . C5 . 116.2(3) yes
C3 . C4 . H41 . 122.8 no
C5 . C4 . H41 . 121.0 no
C4 . C5 . C6 . 130.3(2) yes
C4 . C5 . C8 . 122.1(3) yes
C6 . C5 . C8 . 107.6(2) yes
C5 . C6 . N1 . 106.6(2) yes
C5 . C6 . O1 . 128.8(2) yes
N1 . C6 . O1 . 124.6(2) yes
N1 . C7 . C8 . 106.4(2) yes
N1 . C7 . O2 . 124.7(2) yes
C8 . C7 . O2 . 128.9(2) yes
C7 . C8 . C5 . 108.2(2) yes
C7 . C8 . C1 . 129.8(2) yes
C5 . C8 . C1 . 122.0(2) yes
N2 . C9 . C10 . 113.6(2) yes
N2 . C9 . O3 . 123.0(3) yes
C10 . C9 . O3 . 123.3(3) yes
C9 . C10 . H101 . 105.1 no
C9 . C10 . H102 . 104.6 no
H101 . C10 . H102 . 112.8 no
C9 . C10 . H103 . 108.3 no
H101 . C10 . H103 . 110.9 no
H102 . C10 . H103 . 114.3 no
N1 . C11 . C12 . 111.7(2) yes
N1 . C11 . C14 . 112.1(2) yes
C12 . C11 . C14 . 110.90(19) yes
N1 . C11 . H111 . 103.0 no
C12 . C11 . H111 . 110.3 no
C14 . C11 . H111 . 108.5 no
C11 . C12 . S1 . 113.42(17) yes
C11 . C12 . H121 . 113.7 no
S1 . C12 . H121 . 106.8 no
C11 . C12 . H122 . 107.4 no
S1 . C12 . H122 . 104.6 no
H121 . C12 . H122 . 110.6 no
S1 . C13 . H131 . 114.0 no
S1 . C13 . H132 . 109.9 no
H131 . C13 . H132 . 110.9 no
S1 . C13 . H133 . 106.2 no
H131 . C13 . H133 . 105.8 no
H132 . C13 . H133 . 109.8 no
C11 . C14 . C15 . 118.2(2) yes
C11 . C14 . C19 . 122.4(2) yes
C15 . C14 . C19 . 119.4(2) yes
C14 . C15 . C16 . 120.9(2) yes
C14 . C15 . H151 . 118.4 no
C16 . C15 . H151 . 120.7 no
C15 . C16 . C17 . 119.9(2) yes
C15 . C16 . H161 . 120.5 no
C17 . C16 . H161 . 119.6 no
C16 . C17 . C18 . 119.8(2) yes
C16 . C17 . O6 . 124.6(2) yes
C18 . C17 . O6 . 115.6(2) yes
C17 . C18 . C19 . 119.8(2) yes
C17 . C18 . O7 . 116.0(2) yes
C19 . C18 . O7 . 124.2(2) yes
C14 . C19 . C18 . 120.3(2) yes
C14 . C19 . H191 . 118.0 no
C18 . C19 . H191 . 121.7 no
O6 . C20 . H201 . 105.8 no
O6 . C20 . H202 . 108.3 no
H201 . C20 . H202 . 109.9 no
O6 . C20 . H203 . 110.4 no
H201 . C20 . H203 . 109.9 no
H202 . C20 . H203 . 112.3 no
C22 . C21 . O7 . 107.5(3) yes
C22 . C21 . H211 . 109.1 no
O7 . C21 . H211 . 111.6 no
C22 . C21 . H212 . 109.5 no
O7 . C21 . H212 . 106.7 no
H211 . C21 . H212 . 112.3 no
C21 . C22 . H221 . 112.5 no
C21 . C22 . H222 . 109.3 no
H221 . C22 . H222 . 107.6 no
C21 . C22 . H223 . 110.1 no
H221 . C22 . H223 . 108.5 no
H222 . C22 . H223 . 108.8 no
C20 . O6 . C17 . 116.6(2) yes
C21 . O7 . C18 . 117.2(2) yes
C61 6_556 C61 . C66 6_556 6.8(11) yes
C61 6_556 C61 . C62 . 123.7(7) yes
C66 6_556 C61 . C62 . 116.9(13) yes
C61 6_556 C61 . C65 . 111.8(13) yes
C66 6_556 C61 . C65 . 105.0(15) yes
C62 . C61 . C65 . 11.9(11) yes
C61 6_556 C61 . C67 . 115.6(11) yes
C66 6_556 C61 . C67 . 122.4(19) yes
C62 . C61 . C67 . 120.7(15) yes
C65 . C61 . C67 . 133(2) yes
C61 6_556 C61 . Cl1 . 129.6(9) yes
C66 6_556 C61 . Cl1 . 136.4(19) yes
C62 . C61 . Cl1 . 106.7(14) yes
C65 . C61 . Cl1 . 119(2) yes
C67 . C61 . Cl1 . 14.0(4) yes
C61 6_556 C66 . C66 6_556 6.8(11) yes
C61 6_556 C66 . C62 . 137.1(19) yes
C66 6_556 C66 . C62 . 130.3(13) yes
C61 6_556 C66 . C65 . 123.6(15) yes
C66 6_556 C66 . C65 . 116.8(8) yes
C62 . C66 . C65 . 13.5(10) yes
C61 6_556 C66 . C67 . 108.2(18) yes
C66 6_556 C66 . C67 . 115.0(9) yes
C62 . C66 . C67 . 114.8(20) yes
C65 . C66 . C67 . 128.2(15) yes
C61 6_556 C66 . Cl1 . 120.8(18) yes
C66 6_556 C66 . Cl1 . 127.6(8) yes
C62 . C66 . Cl1 . 102.2(18) yes
C65 . C66 . Cl1 . 115.6(14) yes
C67 . C66 . Cl1 . 12.6(4) yes
C61 . C62 . C66 . 6.5(16) yes
C61 . C62 . C64 . 108.7(12) yes
C66 . C62 . C64 . 102.1(20) yes
C61 . C62 . C63 . 119.4(5) yes
C66 . C62 . C63 . 112.9(16) yes
C64 . C62 . C63 . 10.8(12) yes
C61 . C62 . H621 . 120.5 no
C66 . C62 . H621 . 127.0 no
C64 . C62 . H621 . 130.9 no
C63 . C62 . H621 . 120.1 no
C61 . C62 . H651 . 148.7 no
C66 . C62 . H651 . 155.3 no
C64 . C62 . H651 . 102.6 no
C63 . C62 . H651 . 91.8 no
H621 . C62 . H651 . 28.3 no
C62 . C64 . C63 6_556 123(2) yes
C62 . C64 . C64 6_556 127.6(11) yes
C63 6_556 C64 . C64 6_556 5.0(12) yes
C62 . C64 . C65 . 0.2(7) yes
C63 6_556 C64 . C65 . 122.7(15) yes
C64 6_556 C64 . C65 . 127.7(8) yes
C62 . C64 . H631 . 89.2 no
C63 6_556 C64 . H631 . 148.1 no
C64 6_556 C64 . H631 . 143.1 no
C65 . C64 . H631 . 89.2 no
C62 . C64 . H641 . 118.2 no
C63 6_556 C64 . H641 . 119.1 no
C64 6_556 C64 . H641 . 114.2 no
C65 . C64 . H641 . 118.1 no
H631 . C64 . H641 . 29.0 no
C62 . C63 . C63 6_556 116.8(7) yes
C62 . C63 . C64 6_556 121.7(14) yes
C63 6_556 C63 . C64 6_556 4.9(12) yes
C62 . C63 . C65 . 3(2) yes
C63 6_556 C63 . C65 . 113.6(19) yes
C64 6_556 C63 . C65 . 119(3) yes
C62 . C63 . H631 . 122.5 no
C63 6_556 C63 . H631 . 120.7 no
C64 6_556 C63 . H631 . 115.8 no
C65 . C63 . H631 . 125.6 no
C62 . C63 . H641 . 155.0 no
C63 6_556 C63 . H641 . 88.2 no
C64 6_556 C63 . H641 . 83.2 no
C65 . C63 . H641 . 158.2 no
H631 . C63 . H641 . 32.6 no
C61 . C65 . C64 . 120.5(19) yes
C61 . C65 . C66 . 5.0(17) yes
C64 . C65 . C66 . 115.5(11) yes
C61 . C65 . C63 . 134(3) yes
C64 . C65 . C63 . 14.0(17) yes
C66 . C65 . C63 . 130(2) yes
C61 . C65 . H621 . 96.3 no
C64 . C65 . H621 . 143.2 no
C66 . C65 . H621 . 101.3 no
C63 . C65 . H621 . 129.2 no
C61 . C65 . H651 . 117.2 no
C64 . C65 . H651 . 122.3 no
C66 . C65 . H651 . 122.1 no
C63 . C65 . H651 . 108.3 no
H621 . C65 . H651 . 20.9 no
C61 . C67 . C66 . 0.6(18) yes
C61 . C67 . O68 . 113.7(14) yes
C66 . C67 . O68 . 113.1(11) yes
C61 . C67 . O69 . 115.6(10) yes
C66 . C67 . O69 . 116.1(11) yes
O68 . C67 . O69 . 122.4(10) yes
C67 . O69 . Cl1 . 9.9(5) yes
C67 . O69 . H691 . 114(6) no
Cl1 . O69 . H691 . 106(6) no
C66 . Cl1 . O69 . 100.0(8) yes
C66 . Cl1 . C61 . 2.0(17) yes
O69 . Cl1 . C61 . 98.3(9) yes
C65 . H621 . C62 . 12.3 no
C65 . H621 . H651 . 50.0 no
C62 . H621 . H651 . 62.2 no
C64 . H631 . C63 . 22.5 no
C64 . H631 . H641 . 59.7 no
C63 . H631 . H641 . 82.2 no
H631 . H641 . C63 . 65.2 no
H631 . H641 . C64 . 91.3 no
C63 . H641 . C64 . 26.0 no
C65 . H651 . H621 . 109.2 no
C65 . H651 . C62 . 19.7 no
H621 . H651 . C62 . 89.5 no



_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SQRTW        is   0.00
  Minimum value of RATIO        is  -3.00
;
_chemical_name_systematic        
'N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide hemikis(2-chlorobenzoic acid)'
_chemical_name_common            'apremilast hemikis(2-chlorobenzoic acid)'
_chemical_melting_point          177
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methyl Ethyl Ketone'
####################################################################### 
# 
# 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_APR_3ClBA
_database_code_depnum_ccdc_archive 'CCDC 2477191'
loop_
_audit_author_name
_audit_author_address
'Yelizaveta Naumkina'
;University of Chemistry and Technology Prague
Czech Republic
;
_audit_update_record             
;
2025-07-30 deposited with the CCDC.	2025-10-13 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. 
;


#--------------------------------------------------------------- 
# _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                   13.01710(10)
_cell_length_b                   13.01710(10)
_cell_length_c                   29.3731(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4977.12(11)

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 41 21 2 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-y+1/2,x+1/2,z+1/4
-x,-y,z+1/2
y+1/2,-x+1/2,z-1/4
x+1/2,-y+1/2,-z-1/4
-x+1/2,y+1/2,-z+1/4
y,x,-z
-y,-x,-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'
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            8

# Given Formula = C25.50 H26.50 Cl0.50 N2 O8 S1 
# Dc =      1.44 Fooo =   2256.00 Mu =     21.18 M =    538.79
# Found Formula = C25.50 H26.50 Cl0.50 N2 O8 S1 
# Dc =      1.44 FOOO =   2256.00 Mu =     21.18 M =    538.79

_chemical_formula_sum            'C25.50 H26.50 Cl0.50 N2 O8 S'
_chemical_formula_moiety         'C22 H24 N2 O7 S, 1/2(C7 H5 Cl O2)'
_chemical_compound_source        .
_chemical_formula_weight         538.79


_cell_measurement_reflns_used    9292
_cell_measurement_theta_min      4.54
_cell_measurement_theta_max      62.40
_cell_measurement_temperature    180

_exptl_crystal_description       bipyramidal
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.055
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_max          0.142

_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2256
_exptl_absorpt_coefficient_mu    2.118

# Sheldrick geometric approximatio 0.86 0.89 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.89
_diffrn_measurement_device_type  'Bruker Venture D8'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  polycapillary
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_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      180
_diffrn_reflns_number            43140
_diffrn_reflns_av_unetI/netI     0.048
_reflns_number_total             4494
_diffrn_reflns_av_R_equivalents  0.039
# Number of reflections without Friedels Law is 4494 
# Number of reflections with Friedels Law is 2348 
# Theoretical number of reflections is about 2264 


_diffrn_reflns_theta_min         3.714
_diffrn_reflns_theta_max         67.941
_diffrn_measured_fraction_theta_max 0.993

_diffrn_reflns_theta_full        66.582
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       34
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              35

_oxford_diffrn_Wilson_B_factor   3.53
_oxford_diffrn_Wilson_scale      14.94

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

_refine_diff_density_min         -0.21
_refine_diff_density_max         0.23


# 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     137
_refine_ls_number_parameters     389
_refine_ls_number_reflns         4494
_refine_ls_R_factor_ref          0.0445
_refine_ls_wR_factor_ref         0.0979
_refine_ls_goodness_of_fit_ref   1.0001
_refine_ls_shift/su_max          0.0004264
_refine_ls_shift/su_mean         0.0000256


# Computed with I/sigma = -10 
_reflns_number_all               4494
_refine_ls_R_factor_all          0.0445
_refine_ls_wR_factor_all         0.0979

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4125
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_gt          0.0882

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  0.006(6) # for 1423 Friedel pairs 
_oxford_Bijvoet_difference       0.006(4) # for 1423 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          -0.00(2) # for 2146 Friedel pairs 
_refine_ls_abs_structure_Flack   0.006(4)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 1423 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) + ( 0.03P)² + 3.96P] 
 ,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
S1 S 0.40723(5) 0.83338(5) 0.28303(2) 0.0426 1.0000 Uani . . . . . .
O1 O 0.41098(17) 0.52600(15) 0.30585(7) 0.0517 1.0000 Uani . . . . . .
O2 O 0.48042(15) 0.76540(14) 0.41533(6) 0.0431 1.0000 Uani . . . . . .
O3 O 0.20186(18) 0.6865(2) 0.53964(7) 0.0620 1.0000 Uani . . . . . .
O4 O 0.31500(16) 0.78946(17) 0.30167(7) 0.0525 1.0000 Uani . . . . . .
O5 O 0.45056(17) 0.92090(16) 0.30612(8) 0.0558 1.0000 Uani . . . . . .
O6 O 0.76210(18) 0.4498(2) 0.23962(10) 0.0809 1.0000 Uani . . . . . .
O7 O 0.89415(17) 0.44378(18) 0.30555(10) 0.0740 1.0000 Uani D . . . . .
N1 N 0.46524(18) 0.65663(17) 0.35356(7) 0.0379 1.0000 Uani . . . . . .
N2 N 0.32208(19) 0.71150(19) 0.48424(8) 0.0441 1.0000 Uani . . . . . .
C1 C 0.2934(2) 0.6385(2) 0.45170(9) 0.0405 1.0000 Uani . . . . . .
C2 C 0.2123(2) 0.5690(2) 0.45677(12) 0.0517 1.0000 Uani . . . . . .
C3 C 0.1915(3) 0.4976(3) 0.42271(13) 0.0603 1.0000 Uani . . . . . .
C4 C 0.2492(2) 0.4901(2) 0.38316(11) 0.0527 1.0000 Uani . . . . . .
C5 C 0.3275(2) 0.5602(2) 0.37855(9) 0.0420 1.0000 Uani . . . . . .
C6 C 0.4022(2) 0.5739(2) 0.34107(9) 0.0408 1.0000 Uani . . . . . .
C7 C 0.4372(2) 0.6947(2) 0.39632(8) 0.0362 1.0000 Uani . . . . . .
C8 C 0.3489(2) 0.6332(2) 0.41180(9) 0.0378 1.0000 Uani . . . . . .
C9 C 0.2793(2) 0.7297(2) 0.52645(10) 0.0492 1.0000 Uani . . . . . .
C10 C 0.3368(3) 0.8061(3) 0.55443(11) 0.0609 1.0000 Uani . . . . . .
C11 C 0.5455(2) 0.7023(2) 0.32468(9) 0.0389 1.0000 Uani . . . . . .
C12 C 0.5026(2) 0.7364(2) 0.27871(9) 0.0404 1.0000 Uani . . . . . .
C13 C 0.3837(3) 0.8648(3) 0.22602(11) 0.0626 1.0000 Uani . . . . . .
C14 C 0.6382(2) 0.6330(2) 0.31914(9) 0.0411 1.0000 Uani . . . . . .
C15 C 0.6542(2) 0.5739(2) 0.28012(11) 0.0502 1.0000 Uani . . . . . .
C16 C 0.7403(2) 0.5113(2) 0.27637(12) 0.0571 1.0000 Uani . . . . . .
C17 C 0.8111(2) 0.5079(2) 0.31236(13) 0.0551 1.0000 Uani . . . . . .
C18 C 0.7956(2) 0.5660(2) 0.35059(11) 0.0506 1.0000 Uani . . . . . .
C19 C 0.7094(2) 0.6293(2) 0.35368(10) 0.0441 1.0000 Uani . . . . . .
C20 C 0.6879(3) 0.4452(3) 0.20327(13) 0.0749 1.0000 Uani . . . . . .
C21 C 0.7193(3) 0.3579(4) 0.17246(19) 0.1194 1.0000 Uani . . . . . .
C22 C 0.9674(3) 0.4398(3) 0.34195(13) 0.0752 1.0000 Uani . . . . . .
H21 H 0.1721 0.5678 0.4825 0.0638 1.0000 Uiso R . . . . .
H22 H 0.373(3) 0.748(3) 0.4763(11) 0.052(2) 1.0000 Uiso . . . . . .
H31 H 0.1338 0.4570 0.4262 0.0727 1.0000 Uiso R . . . . .
H41 H 0.2365 0.4377 0.3609 0.0635 1.0000 Uiso R . . . . .
H101 H 0.3493 0.8684 0.5370 0.0945 1.0000 Uiso R . . . . .
H102 H 0.4020 0.7755 0.5619 0.0955 1.0000 Uiso R . . . . .
H103 H 0.2928 0.8212 0.5812 0.0960 1.0000 Uiso R . . . . .
H111 H 0.5653 0.7602 0.3422 0.0501 1.0000 Uiso R . . . . .
H121 H 0.5579 0.7654 0.2600 0.0508 1.0000 Uiso R . . . . .
H122 H 0.4664 0.6807 0.2613 0.0508 1.0000 Uiso R . . . . .
H131 H 0.3360 0.9240 0.2254 0.0958 1.0000 Uiso R . . . . .
H132 H 0.4514 0.8824 0.2126 0.0952 1.0000 Uiso R . . . . .
H133 H 0.3542 0.8051 0.2101 0.0956 1.0000 Uiso R . . . . .
H151 H 0.6072 0.5770 0.2560 0.0661 1.0000 Uiso R . . . . .
H181 H 0.8430 0.5599 0.3738 0.0616 1.0000 Uiso R . . . . .
H191 H 0.6995 0.6703 0.3802 0.0538 1.0000 Uiso R . . . . .
H201 H 0.6894 0.5114 0.1842 0.0882 1.0000 Uiso R . . . . .
H202 H 0.6187 0.4229 0.2148 0.0875 1.0000 Uiso R . . . . .
H211 H 0.7271 0.2977 0.1918 0.1597 1.0000 Uiso R . . . . .
H212 H 0.7826 0.3796 0.1577 0.1603 1.0000 Uiso R . . . . .
H213 H 0.6654 0.3467 0.1495 0.1598 1.0000 Uiso R . . . . .
H221 H 1.0231 0.3949 0.3317 0.1120 1.0000 Uiso R . . . . .
H222 H 0.9941 0.5099 0.3494 0.1138 1.0000 Uiso R . . . . .
H223 H 0.9362 0.4086 0.3682 0.1116 1.0000 Uiso R . . . . .
Cl1 Cl 0.9356(2) -0.05527(17) 0.16236(8) 0.0939 0.5000 Uani D . . . . .
O68 O 0.9417(5) 0.2011(4) 0.34314(17) 0.0778 0.5000 Uani D . . . . .
O69 O 0.8831(4) 0.2468(4) 0.27475(16) 0.0642 0.5000 Uani D . . . . .
C61 C 0.9702(5) 0.0891(5) 0.2809(2) 0.0609 0.5000 Uani D . . . . .
C62 C 0.9369(6) 0.0623(6) 0.2373(2) 0.0583 0.5000 Uani D . . . . .
C63 C 0.9785(8) -0.0226(7) 0.2164(3) 0.0653 0.5000 Uani D . . . . .
C64 C 1.0554(9) -0.0790(8) 0.2380(2) 0.0668 0.5000 Uani D . . . . .
C65 C 1.0866(8) -0.0523(9) 0.2813(3) 0.0707 0.5000 Uani D . . . . .
C66 C 1.0420(8) 0.0302(8) 0.3026(3) 0.0729 0.5000 Uani D . . . . .
C67 C 0.9320(5) 0.1822(5) 0.3040(2) 0.0587 0.5000 Uani D . . . . .
H621 H 0.8872 0.1019 0.2230 0.0680 0.5000 Uiso R . . . . .
H641 H 1.0875 -0.1347 0.2227 0.0779 0.5000 Uiso R . . . . .
H651 H 1.1389 -0.0909 0.2960 0.0847 0.5000 Uiso R . . . . .
H661 H 1.0610 0.0467 0.3330 0.0876 0.5000 Uiso R . . . . .
H691 H 0.878(6) 0.304(2) 0.288(2) 0.094(2) 0.5000 Uiso D . . . . .

_refine_ls_extinction_coef       75(9)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.09735(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
S1 . O4 . 1.438(2) yes
S1 . O5 . 1.441(2) yes
S1 . C12 . 1.775(3) yes
S1 . C13 . 1.750(3) yes
O1 . C6 . 1.213(3) yes
O2 . C7 . 1.215(3) yes
O3 . C9 . 1.217(4) yes
O6 . C16 . 1.374(4) yes
O6 . C20 . 1.441(4) yes
O7 . C17 . 1.380(4) yes
O7 . C22 . 1.433(4) yes
N1 . C6 . 1.403(4) yes
N1 . C7 . 1.399(3) yes
N1 . C11 . 1.471(4) yes
N2 . C1 . 1.399(4) yes
N2 . C9 . 1.380(4) yes
N2 . H22 . 0.84(3) no
C1 . C2 . 1.398(4) yes
C1 . C8 . 1.379(4) yes
C2 . C3 . 1.392(5) yes
C2 . H21 . 0.919 no
C3 . C4 . 1.387(5) yes
C3 . H31 . 0.924 no
C4 . C5 . 1.375(4) yes
C4 . H41 . 0.959 no
C5 . C6 . 1.480(4) yes
C5 . C8 . 1.391(4) yes
C7 . C8 . 1.473(4) yes
C9 . C10 . 1.492(4) yes
C10 . H101 . 0.973 no
C10 . H102 . 0.963 no
C10 . H103 . 0.993 no
C11 . C12 . 1.527(4) yes
C11 . C14 . 1.515(4) yes
C11 . H111 . 0.949 no
C12 . H121 . 0.981 no
C12 . H122 . 1.003 no
C13 . H131 . 0.990 no
C13 . H132 . 0.993 no
C13 . H133 . 0.985 no
C14 . C15 . 1.396(4) yes
C14 . C19 . 1.375(4) yes
C15 . C16 . 1.389(4) yes
C15 . H151 . 0.937 no
C16 . C17 . 1.403(4) yes
C17 . C18 . 1.369(5) yes
C18 . C19 . 1.395(4) yes
C18 . H181 . 0.923 no
C19 . H191 . 0.953 no
C20 . C21 . 1.509(5) yes
C20 . H201 . 1.028 no
C20 . H202 . 1.006 no
C21 . H211 . 0.973 no
C21 . H212 . 0.974 no
C21 . H213 . 0.985 no
C22 . H221 . 0.979 no
C22 . H222 . 1.001 no
C22 . H223 . 0.961 no
Cl1 . C61 8_665 2.026(7) yes
Cl1 . C66 8_665 1.134(9) yes
Cl1 . C63 . 1.734(9) yes
O68 . C67 . 1.182(8) yes
O69 . C67 . 1.361(7) yes
O69 . H691 . 0.848(17) no
C61 . H621 8_665 0.994 no
C61 . C63 8_665 1.116(12) yes
C61 . C62 . 1.397(8) yes
C61 . C66 . 1.368(11) yes
C61 . C67 . 1.475(8) yes
C62 . C63 8_665 1.838(10) yes
C62 . C66 8_665 1.844(11) yes
C62 . C63 . 1.375(10) yes
C62 . H621 . 0.928 no
C63 . C65 8_665 1.274(12) yes
C63 . C64 . 1.396(10) yes
C64 . C66 8_665 1.703(14) yes
C64 . C64 8_665 0.826(19) yes
C64 . C65 . 1.380(7) yes
C64 . H641 . 0.950 no
C65 . H641 8_665 0.784 no
C65 . C66 . 1.371(8) yes
C65 . H651 . 0.950 no
C66 . H661 . 0.950 no
C67 . H621 8_665 1.282 no
H641 . H651 8_665 0.554 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
O4 . S1 . O5 . 117.51(13) yes
O4 . S1 . C12 . 109.16(14) yes
O5 . S1 . C12 . 108.80(14) yes
O4 . S1 . C13 . 108.12(16) yes
O5 . S1 . C13 . 109.52(16) yes
C12 . S1 . C13 . 102.71(15) yes
C16 . O6 . C20 . 117.9(2) yes
C17 . O7 . C22 . 115.8(3) yes
C6 . N1 . C7 . 110.7(2) yes
C6 . N1 . C11 . 125.1(2) yes
C7 . N1 . C11 . 124.1(2) yes
C1 . N2 . C9 . 128.5(3) yes
C1 . N2 . H22 . 113(2) no
C9 . N2 . H22 . 118(2) no
N2 . C1 . C2 . 124.7(3) yes
N2 . C1 . C8 . 118.4(2) yes
C2 . C1 . C8 . 117.0(3) yes
C1 . C2 . C3 . 120.2(3) yes
C1 . C2 . H21 . 121.9 no
C3 . C2 . H21 . 118.0 no
C2 . C3 . C4 . 123.0(3) yes
C2 . C3 . H31 . 117.3 no
C4 . C3 . H31 . 119.6 no
C3 . C4 . C5 . 115.9(3) yes
C3 . C4 . H41 . 121.9 no
C5 . C4 . H41 . 122.1 no
C4 . C5 . C6 . 129.8(3) yes
C4 . C5 . C8 . 122.2(3) yes
C6 . C5 . C8 . 108.0(2) yes
C5 . C6 . N1 . 106.4(2) yes
C5 . C6 . O1 . 129.4(3) yes
N1 . C6 . O1 . 124.2(3) yes
N1 . C7 . O2 . 124.1(3) yes
N1 . C7 . C8 . 106.7(2) yes
O2 . C7 . C8 . 129.2(2) yes
C7 . C8 . C5 . 108.1(2) yes
C7 . C8 . C1 . 130.1(2) yes
C5 . C8 . C1 . 121.8(3) yes
N2 . C9 . O3 . 122.8(3) yes
N2 . C9 . C10 . 114.0(3) yes
O3 . C9 . C10 . 123.2(3) yes
C9 . C10 . H101 . 110.5 no
C9 . C10 . H102 . 107.0 no
H101 . C10 . H102 . 108.4 no
C9 . C10 . H103 . 106.2 no
H101 . C10 . H103 . 110.4 no
H102 . C10 . H103 . 114.2 no
N1 . C11 . C12 . 111.5(2) yes
N1 . C11 . C14 . 112.8(2) yes
C12 . C11 . C14 . 111.7(2) yes
N1 . C11 . H111 . 101.6 no
C12 . C11 . H111 . 110.4 no
C14 . C11 . H111 . 108.4 no
C11 . C12 . S1 . 113.55(18) yes
C11 . C12 . H121 . 109.7 no
S1 . C12 . H121 . 106.3 no
C11 . C12 . H122 . 114.3 no
S1 . C12 . H122 . 102.8 no
H121 . C12 . H122 . 109.7 no
S1 . C13 . H131 . 108.0 no
S1 . C13 . H132 . 106.3 no
H131 . C13 . H132 . 111.7 no
S1 . C13 . H133 . 109.7 no
H131 . C13 . H133 . 111.2 no
H132 . C13 . H133 . 109.8 no
C11 . C14 . C15 . 122.3(2) yes
C11 . C14 . C19 . 118.6(3) yes
C15 . C14 . C19 . 119.1(3) yes
C14 . C15 . C16 . 120.6(3) yes
C14 . C15 . H151 . 119.9 no
C16 . C15 . H151 . 119.5 no
C15 . C16 . O6 . 124.8(3) yes
C15 . C16 . C17 . 119.3(3) yes
O6 . C16 . C17 . 115.9(3) yes
C16 . C17 . O7 . 115.2(3) yes
C16 . C17 . C18 . 120.2(3) yes
O7 . C17 . C18 . 124.7(3) yes
C17 . C18 . C19 . 119.9(3) yes
C17 . C18 . H181 . 117.3 no
C19 . C18 . H181 . 122.8 no
C18 . C19 . C14 . 121.0(3) yes
C18 . C19 . H191 . 119.5 no
C14 . C19 . H191 . 119.5 no
O6 . C20 . C21 . 107.1(3) yes
O6 . C20 . H201 . 110.9 no
C21 . C20 . H201 . 107.4 no
O6 . C20 . H202 . 111.2 no
C21 . C20 . H202 . 103.2 no
H201 . C20 . H202 . 116.3 no
C20 . C21 . H211 . 106.5 no
C20 . C21 . H212 . 106.2 no
H211 . C21 . H212 . 113.9 no
C20 . C21 . H213 . 109.3 no
H211 . C21 . H213 . 110.8 no
H212 . C21 . H213 . 109.9 no
O7 . C22 . H221 . 106.5 no
O7 . C22 . H222 . 111.3 no
H221 . C22 . H222 . 110.8 no
O7 . C22 . H223 . 109.4 no
H221 . C22 . H223 . 107.9 no
H222 . C22 . H223 . 110.8 no
C61 8_665 Cl1 . C66 8_665 40.0(5) yes
C61 8_665 Cl1 . C63 . 33.4(4) yes
C66 8_665 Cl1 . C63 . 6.8(7) yes
C67 . O69 . H691 . 106(6) no
H621 8_665 C61 . Cl1 8_665 131.4 no
H621 8_665 C61 . C63 8_665 146.0 no
Cl1 8_665 C61 . C63 8_665 58.8(5) yes
H621 8_665 C61 . C62 . 71.2 no
Cl1 8_665 C61 . C62 . 152.1(5) yes
C63 8_665 C61 . C62 . 93.3(7) yes
H621 8_665 C61 . C66 . 150.9 no
Cl1 8_665 C61 . C66 . 32.2(4) yes
C63 8_665 C61 . C66 . 26.6(6) yes
C62 . C61 . C66 . 119.9(5) yes
H621 8_665 C61 . C67 . 58.8 no
Cl1 8_665 C61 . C67 . 86.3(4) yes
C63 8_665 C61 . C67 . 145.1(8) yes
C62 . C61 . C67 . 121.6(6) yes
C66 . C61 . C67 . 118.5(6) yes
C61 . C62 . C63 8_665 37.3(5) yes
C61 . C62 . C66 8_665 134.1(5) yes
C63 8_665 C62 . C66 8_665 96.8(3) yes
C61 . C62 . C63 . 119.3(3) yes
C63 8_665 C62 . C63 . 82.0(5) yes
C66 8_665 C62 . C63 . 14.7(5) yes
C61 . C62 . H621 . 119.4 no
C63 8_665 C62 . H621 . 156.7 no
C66 8_665 C62 . H621 . 106.5 no
C63 . C62 . H621 . 121.3 no
Cl1 . C63 . C62 . 118.7(5) yes
Cl1 . C63 . C65 8_665 97.5(6) yes
C62 . C63 . C65 8_665 143.0(9) yes
Cl1 . C63 . C62 8_665 137.2(6) yes
C62 . C63 . C62 8_665 21.2(4) yes
C65 8_665 C63 . C62 8_665 125.1(7) yes
Cl1 . C63 . C61 8_665 87.8(7) yes
C62 . C63 . C61 8_665 33.6(5) yes
C65 8_665 C63 . C61 8_665 172.2(12) yes
C62 8_665 C63 . C61 8_665 49.4(5) yes
Cl1 . C63 . C64 . 121.3(7) yes
C62 . C63 . C64 . 120.0(6) yes
C65 8_665 C63 . C64 . 24.5(6) yes
C62 8_665 C63 . C64 . 100.9(5) yes
C61 8_665 C63 . C64 . 148.7(9) yes
C63 . C64 . C66 8_665 20.2(5) yes
C63 . C64 . C64 8_665 117.3(6) yes
C66 8_665 C64 . C64 8_665 137.3(7) yes
C63 . C64 . C65 . 119.9(6) yes
C66 8_665 C64 . C65 . 140.2(7) yes
C64 8_665 C64 . C65 . 9.1(16) yes
C63 . C64 . H641 . 120.0 no
C66 8_665 C64 . H641 . 99.8 no
C64 8_665 C64 . H641 . 121.6 no
C65 . C64 . H641 . 120.1 no
C64 . C65 . C63 8_665 92.7(6) yes
C64 . C65 . H641 8_665 87.0 no
C63 8_665 C65 . H641 8_665 166.1 no
C64 . C65 . C66 . 119.5(3) yes
C63 8_665 C65 . C66 . 26.9(5) yes
H641 8_665 C65 . C66 . 149.8 no
C64 . C65 . H651 . 119.8 no
C63 8_665 C65 . H651 . 147.6 no
H641 8_665 C65 . H651 . 35.7 no
C66 . C65 . H651 . 120.7 no
C64 8_665 C66 . C65 . 17.9(3) yes
C64 8_665 C66 . C61 . 103.5(7) yes
C65 . C66 . C61 . 121.1(6) yes
C64 8_665 C66 . C62 8_665 85.1(6) yes
C65 . C66 . C62 8_665 101.8(5) yes
C61 . C66 . C62 8_665 21.5(4) yes
C64 8_665 C66 . Cl1 8_665 148.2(9) yes
C65 . C66 . Cl1 8_665 131.0(8) yes
C61 . C66 . Cl1 8_665 107.8(7) yes
C62 8_665 C66 . Cl1 8_665 126.7(8) yes
C64 8_665 C66 . H661 . 137.2 no
C65 . C66 . H661 . 119.7 no
C61 . C66 . H661 . 119.2 no
C62 8_665 C66 . H661 . 137.3 no
Cl1 8_665 C66 . H661 . 11.5 no
C61 . C67 . O69 . 112.0(6) yes
C61 . C67 . H621 8_665 41.6 no
O69 . C67 . H621 8_665 83.3 no
C61 . C67 . O68 . 125.6(6) yes
O69 . C67 . O68 . 122.4(6) yes
H621 8_665 C67 . O68 . 141.8 no
C61 8_665 H621 . C62 . 46.5 no
C61 8_665 H621 . C67 8_665 79.7 no
C62 . H621 . C67 8_665 125.4 no
H651 8_665 H641 . C64 . 125.6 no
H651 8_665 H641 . C65 8_665 88.7 no
C64 . H641 . C65 8_665 37.5 no
H641 8_665 H651 . C65 . 55.6 no



_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of RATIO        is  -3.00
;
_chemical_name_systematic        
'N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide hemikis(3-chlorobenzoic acid)'
_chemical_name_common            'apremilast hemikis(3-chlorobenzoic acid)'
_chemical_melting_point          170
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methyl Ethyl Ketone'
####################################################################### 
# 
# 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_APR_3BrBA
_database_code_depnum_ccdc_archive 'CCDC 2477190'
loop_
_audit_author_name
_audit_author_address
'Yelizaveta Naumkina'
;University of Chemistry and Technology Prague
Czech Republic
;
_audit_update_record             
;
2025-07-30 deposited with the CCDC.	2025-10-13 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. 
;


#--------------------------------------------------------------- 
# _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                   13.0239(2)
_cell_length_b                   13.0239(2)
_cell_length_c                   29.5351(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5009.80(19)

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 41 21 2 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-y+1/2,x+1/2,z+1/4
-x,-y,z+1/2
y+1/2,-x+1/2,z-1/4
x+1/2,-y+1/2,-z-1/4
-x+1/2,y+1/2,-z+1/4
y,x,-z
-y,-x,-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'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 '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            8

# Given Formula = C25.50 H26.50 Br0.50 N2 O8 S1 
# Dc =      1.49 Fooo =   2328.00 Mu =     25.48 M =    561.02
# Found Formula = C25.50 H26.50 Br0.50 N2 O8 S1 
# Dc =      1.49 FOOO =   2328.00 Mu =     25.48 M =    561.02

_chemical_formula_sum            'C25.50 H26.50 Br0.50 N2 O8 S1'
_chemical_formula_moiety         'C22 H24 N2 O7 S, 1/2(C7 H5 Br O2)'
_chemical_compound_source        .
_chemical_formula_weight         561.02


_cell_measurement_reflns_used    9867
_cell_measurement_theta_min      3.71
_cell_measurement_theta_max      72.20
_cell_measurement_temperature    180

_exptl_crystal_description       bipyramidal
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.085
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_max          0.182

_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2328
_exptl_absorpt_coefficient_mu    2.548

# Sheldrick geometric approximatio 0.75 0.81 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.81
_diffrn_measurement_device_type  'Bruker Venture D8'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  polycapillary
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_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      180
_diffrn_reflns_number            4949
_diffrn_reflns_av_unetI/netI     0.020
_reflns_number_total             4949
_diffrn_reflns_av_R_equivalents  0.0644
# Number of reflections without Friedels Law is 4949 
# Number of reflections with Friedels Law is 2904 
# Theoretical number of reflections is about 2476 


_diffrn_reflns_theta_min         3.709
_diffrn_reflns_theta_max         72.326
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        72.326
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       36
_reflns_limit_h_min              -10
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              36

_oxford_diffrn_Wilson_B_factor   3.84
_oxford_diffrn_Wilson_scale      252.01

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

_refine_diff_density_min         -0.50
_refine_diff_density_max         0.50


# 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     152
_refine_ls_number_parameters     388
_refine_ls_number_reflns         4949
_refine_ls_R_factor_ref          0.0842
_refine_ls_wR_factor_ref         0.1981
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_shift/su_max          0.0006460
_refine_ls_shift/su_mean         0.0000431


# Computed with I/sigma = -10 
_reflns_number_all               4949
_refine_ls_R_factor_all          0.0842
_refine_ls_wR_factor_all         0.1981

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4846
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_gt          0.1975

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  0.015(5) # for 1650 Friedel pairs 
_oxford_Bijvoet_difference       0.052(6) # for 1650 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.06(4) # for 2045 Friedel pairs 
_refine_ls_abs_structure_Flack   0.052(6)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 1650 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) + ( 0.04P)² +26.53P] 
 ,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
S1 S 0.16589(12) 0.40609(12) 0.53335(5) 0.0389 1.0000 Uani . . . . . .
O1 O 0.4729(3) 0.4095(4) 0.55559(15) 0.0514 1.0000 Uani . . . . . .
O2 O 0.2352(3) 0.4788(3) 0.66491(13) 0.0375 1.0000 Uani . . . . . .
O3 O 0.3132(5) 0.2003(4) 0.78844(16) 0.0680 1.0000 Uani . . . . . .
O4 O 0.2098(4) 0.3131(4) 0.55170(15) 0.0505 1.0000 Uani . . . . . .
O5 O 0.0793(3) 0.4492(4) 0.55613(16) 0.0528 1.0000 Uani . . . . . .
O6 O 0.5498(5) 0.7614(4) 0.4906(2) 0.0895 1.0000 Uani . . . . . .
O7 O 0.5552(4) 0.8933(4) 0.5564(2) 0.0817 1.0000 Uani . . . . . .
N1 N 0.3426(3) 0.4636(4) 0.60311(15) 0.0346 1.0000 Uani . . . . . .
N2 N 0.2900(4) 0.3220(4) 0.73342(16) 0.0406 1.0000 Uani D . . . . .
C1 C 0.3621(4) 0.2934(5) 0.7006(2) 0.0383 1.0000 Uani D . . . . .
C2 C 0.4315(5) 0.2117(5) 0.7064(2) 0.0476 1.0000 Uani . . . . . .
C3 C 0.5026(5) 0.1902(5) 0.6719(3) 0.0566 1.0000 Uani . . . . . .
C4 C 0.5090(5) 0.2474(6) 0.6324(3) 0.0527 1.0000 Uani . . . . . .
C5 C 0.4398(5) 0.3253(5) 0.6282(2) 0.0409 1.0000 Uani . . . . . .
C6 C 0.4250(5) 0.4010(5) 0.5906(2) 0.0431 1.0000 Uani . . . . . .
C7 C 0.3046(4) 0.4373(5) 0.64585(18) 0.0346 1.0000 Uani . . . . . .
C8 C 0.3669(4) 0.3477(5) 0.6617(2) 0.0375 1.0000 Uani . . . . . .
C9 C 0.2690(6) 0.2778(5) 0.7755(2) 0.0491 1.0000 Uani D . . . . .
C10 C 0.1950(7) 0.3359(6) 0.8036(3) 0.0691 1.0000 Uani . . . . . .
C11 C 0.1338(6) 0.3841(6) 0.4766(2) 0.0602 1.0000 Uani . . . . . .
C12 C 0.2628(5) 0.5021(5) 0.52897(19) 0.0396 1.0000 Uani . . . . . .
C13 C 0.2957(4) 0.5449(5) 0.57472(18) 0.0347 1.0000 Uani . . . . . .
C14 C 0.3662(4) 0.6373(5) 0.5692(2) 0.0383 1.0000 Uani . . . . . .
C15 C 0.4249(5) 0.6525(5) 0.5305(2) 0.0517 1.0000 Uani . . . . . .
C16 C 0.4874(6) 0.7383(5) 0.5264(3) 0.0664 1.0000 Uani . . . . . .
C17 C 0.4901(5) 0.8112(6) 0.5625(3) 0.0608 1.0000 Uani . . . . . .
C18 C 0.4322(5) 0.7939(5) 0.6001(2) 0.0497 1.0000 Uani . . . . . .
C19 C 0.3695(5) 0.7087(5) 0.6040(2) 0.0438 1.0000 Uani . . . . . .
C20 C 0.5534(8) 0.6887(6) 0.4541(3) 0.0946 1.0000 Uani . . . . . .
C21 C 0.6460(11) 0.7182(7) 0.4255(4) 0.1480 1.0000 Uani . . . . . .
C22 C 0.5618(8) 0.9653(5) 0.5918(3) 0.0786 1.0000 Uani . . . . . .
H21 H 0.4328 0.1763 0.7334 0.0573 1.0000 Uiso R . . . . .
H22 H 0.241(3) 0.360(4) 0.7230(10) 0.049(2) 1.0000 Uiso D . . . . .
H31 H 0.5455 0.1343 0.6760 0.0720 1.0000 Uiso R . . . . .
H41 H 0.5575 0.2333 0.6108 0.0650 1.0000 Uiso R . . . . .
H101 H 0.1313 0.3396 0.7889 0.1102 1.0000 Uiso R . . . . .
H102 H 0.2241 0.4050 0.8059 0.1100 1.0000 Uiso R . . . . .
H103 H 0.1916 0.3066 0.8330 0.1097 1.0000 Uiso R . . . . .
H111 H 0.1882 0.3565 0.4588 0.0960 1.0000 Uiso R . . . . .
H112 H 0.1054 0.4461 0.4623 0.0960 1.0000 Uiso R . . . . .
H113 H 0.0782 0.3321 0.4764 0.0961 1.0000 Uiso R . . . . .
H121 H 0.2318 0.5601 0.5122 0.0566 1.0000 Uiso R . . . . .
H122 H 0.3166 0.4719 0.5128 0.0568 1.0000 Uiso R . . . . .
H131 H 0.2343 0.5707 0.5910 0.0446 1.0000 Uiso R . . . . .
H151 H 0.4205 0.6081 0.5069 0.0719 1.0000 Uiso R . . . . .
H181 H 0.4349 0.8420 0.6237 0.0673 1.0000 Uiso R . . . . .
H191 H 0.3302 0.6998 0.6305 0.0554 1.0000 Uiso R . . . . .
H201 H 0.5565 0.6194 0.4621 0.1152 1.0000 Uiso R . . . . .
H202 H 0.4913 0.7016 0.4341 0.1151 1.0000 Uiso R . . . . .
H211 H 0.6435 0.7895 0.4160 0.2400 1.0000 Uiso R . . . . .
H212 H 0.7142 0.7147 0.4424 0.2400 1.0000 Uiso R . . . . .
H213 H 0.6526 0.6766 0.3990 0.2400 1.0000 Uiso R . . . . .
H221 H 0.6164 1.0139 0.5832 0.1148 1.0000 Uiso R . . . . .
H222 H 0.5807 0.9332 0.6192 0.1149 1.0000 Uiso R . . . . .
H223 H 0.4990 1.0018 0.5944 0.1151 1.0000 Uiso R . . . . .
O69 O 0.8834(9) 0.7517(8) 0.4739(4) 0.0648 0.5000 Uani D . . . . .
O68 O 0.9397(10) 0.7961(9) 0.4054(4) 0.0753 0.5000 Uani D . . . . .
C61 C 0.9684(8) 0.9117(9) 0.4679(4) 0.0639 0.5000 Uani D . . . . .
C63 C 0.9705(10) 1.0209(11) 0.5338(4) 0.0672 0.5000 Uani D . . . . .
C62 C 0.9315(7) 0.9363(9) 0.5118(3) 0.0596 0.5000 Uani D . . . . .
C65 C 1.0807(8) 1.0575(11) 0.4696(5) 0.0717 0.5000 Uani D . . . . .
C64 C 1.0447(9) 1.0827(8) 0.5133(4) 0.0680 0.5000 Uani D . . . . .
C66 C 1.0419(10) 0.9738(13) 0.4478(4) 0.0713 0.5000 Uani D . . . . .
C67 C 0.9252(9) 0.8181(7) 0.4456(5) 0.0609 0.5000 Uani D . . . . .
Br1 Br 0.92338(19) 1.05703(15) 0.59075(7) 0.0833 0.5000 Uani D . . . . .
H621 H 0.8816 0.8932 0.5251 0.0721 0.5000 Uiso R . . . . .
H641 H 1.0728 1.1432 0.5284 0.0819 0.5000 Uiso R . . . . .
H651 H 1.1327 1.1013 0.4567 0.0852 0.5000 Uiso R . . . . .
H661 H 1.0662 0.9580 0.4186 0.0855 0.5000 Uiso R . . . . .
H691 H 0.908(15) 0.694(6) 0.474(7) 0.096(2) 0.5000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2926(5)
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
S1 . O4 . 1.445(5) yes
S1 . O5 . 1.428(5) yes
S1 . C11 . 1.752(6) yes
S1 . C12 . 1.782(6) yes
O1 . C6 . 1.214(7) yes
O2 . C7 . 1.194(7) yes
O3 . C9 . 1.224(8) yes
O6 . C16 . 1.367(9) yes
O6 . C20 . 1.437(10) yes
O7 . C17 . 1.377(9) yes
O7 . C22 . 1.406(9) yes
N1 . C6 . 1.397(8) yes
N1 . C7 . 1.398(7) yes
N1 . C13 . 1.482(8) yes
N2 . C1 . 1.402(7) yes
N2 . C9 . 1.397(8) yes
N2 . H22 . 0.867(19) no
C1 . C2 . 1.406(9) yes
C1 . C8 . 1.348(9) yes
C2 . C3 . 1.404(10) yes
C2 . H21 . 0.923 no
C3 . C4 . 1.389(11) yes
C3 . H31 . 0.926 no
C4 . C5 . 1.363(9) yes
C4 . H41 . 0.915 no
C5 . C6 . 1.497(9) yes
C5 . C8 . 1.402(8) yes
C7 . C8 . 1.497(9) yes
C9 . C10 . 1.479(10) yes
C10 . H101 . 0.937 no
C10 . H102 . 0.979 no
C10 . H103 . 0.950 no
C11 . H111 . 0.951 no
C11 . H112 . 0.983 no
C11 . H113 . 0.991 no
C12 . C13 . 1.523(7) yes
C12 . H121 . 0.990 no
C12 . H122 . 0.936 no
C13 . C14 . 1.523(8) yes
C13 . H131 . 0.992 no
C14 . C15 . 1.388(9) yes
C14 . C19 . 1.388(8) yes
C15 . C16 . 1.387(9) yes
C15 . H151 . 0.908 no
C16 . C17 . 1.428(10) yes
C17 . C18 . 1.361(11) yes
C18 . C19 . 1.382(10) yes
C18 . H181 . 0.938 no
C19 . H191 . 0.942 no
C20 . C21 . 1.522(11) yes
C20 . H201 . 0.935 no
C20 . H202 . 1.016 no
C21 . H211 . 0.970 no
C21 . H212 . 1.020 no
C21 . H213 . 0.956 no
C22 . H221 . 0.985 no
C22 . H222 . 0.944 no
C22 . H223 . 0.949 no
O69 . C67 . 1.320(18) yes
O69 . H691 . 0.82(2) no
O68 . Br1 7_556 2.258(12) yes
O68 . C67 . 1.235(18) yes
C61 . H621 7_556 1.075 no
C61 . Br1 7_556 2.086(12) yes
C61 . C63 7_556 1.03(2) yes
C61 . C62 7_556 0.78(2) yes
C61 . C62 . 1.421(9) yes
C61 . C66 . 1.39(2) yes
C61 . C67 . 1.495(16) yes
C63 . C65 7_556 1.38(2) yes
C63 . C62 7_556 1.835(18) yes
C63 . C62 . 1.377(18) yes
C63 . C64 . 1.395(17) yes
C63 . Br1 . 1.852(13) yes
C62 . H621 . 0.943 no
C65 . H641 7_556 0.840 no
C65 . C65 7_556 1.85(3) yes
C65 . C64 . 1.412(9) yes
C65 . C66 . 1.36(2) yes
C65 . H651 . 0.963 no
C64 . C66 7_556 1.57(3) yes
C64 . C64 7_556 1.05(3) yes
C64 . H641 . 0.976 no
C66 . Br1 7_556 1.328(14) yes
C66 . H661 . 0.939 no
C67 . H621 7_556 1.268 no
H641 . H651 7_556 0.592 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
O4 . S1 . O5 . 117.7(3) yes
O4 . S1 . C11 . 108.4(4) yes
O5 . S1 . C11 . 109.1(4) yes
O4 . S1 . C12 . 109.6(3) yes
O5 . S1 . C12 . 108.5(3) yes
C11 . S1 . C12 . 102.4(3) yes
C16 . O6 . C20 . 117.2(5) yes
C17 . O7 . C22 . 117.3(7) yes
C6 . N1 . C7 . 111.5(5) yes
C6 . N1 . C13 . 125.8(5) yes
C7 . N1 . C13 . 122.7(4) yes
C1 . N2 . C9 . 129.7(6) yes
C1 . N2 . H22 . 113.6(15) no
C9 . N2 . H22 . 114.2(15) no
N2 . C1 . C2 . 123.2(6) yes
N2 . C1 . C8 . 118.7(5) yes
C2 . C1 . C8 . 118.1(6) yes
C1 . C2 . C3 . 119.1(7) yes
C1 . C2 . H21 . 119.8 no
C3 . C2 . H21 . 121.0 no
C2 . C3 . C4 . 122.9(6) yes
C2 . C3 . H31 . 117.4 no
C4 . C3 . H31 . 119.7 no
C3 . C4 . C5 . 115.8(6) yes
C3 . C4 . H41 . 121.3 no
C5 . C4 . H41 . 122.9 no
C4 . C5 . C6 . 130.0(6) yes
C4 . C5 . C8 . 122.6(6) yes
C6 . C5 . C8 . 107.4(5) yes
C5 . C6 . N1 . 106.7(5) yes
C5 . C6 . O1 . 128.8(6) yes
N1 . C6 . O1 . 124.5(7) yes
N1 . C7 . O2 . 125.6(6) yes
N1 . C7 . C8 . 106.4(5) yes
O2 . C7 . C8 . 128.0(5) yes
C7 . C8 . C5 . 107.9(5) yes
C7 . C8 . C1 . 130.6(5) yes
C5 . C8 . C1 . 121.5(6) yes
N2 . C9 . O3 . 121.7(6) yes
N2 . C9 . C10 . 114.6(6) yes
O3 . C9 . C10 . 123.7(7) yes
C9 . C10 . H101 . 110.1 no
C9 . C10 . H102 . 104.8 no
H101 . C10 . H102 . 109.1 no
C9 . C10 . H103 . 109.7 no
H101 . C10 . H103 . 113.8 no
H102 . C10 . H103 . 109.0 no
S1 . C11 . H111 . 114.3 no
S1 . C11 . H112 . 111.4 no
H111 . C11 . H112 . 110.8 no
S1 . C11 . H113 . 106.9 no
H111 . C11 . H113 . 106.5 no
H112 . C11 . H113 . 106.4 no
S1 . C12 . C13 . 113.0(4) yes
S1 . C12 . H121 . 106.5 no
C13 . C12 . H121 . 106.3 no
S1 . C12 . H122 . 105.8 no
C13 . C12 . H122 . 113.4 no
H121 . C12 . H122 . 111.8 no
C12 . C13 . N1 . 110.9(5) yes
C12 . C13 . C14 . 111.3(5) yes
N1 . C13 . C14 . 112.1(5) yes
C12 . C13 . H131 . 109.2 no
N1 . C13 . H131 . 107.4 no
C14 . C13 . H131 . 105.7 no
C13 . C14 . C15 . 122.2(5) yes
C13 . C14 . C19 . 117.9(6) yes
C15 . C14 . C19 . 119.8(6) yes
C14 . C15 . C16 . 120.6(6) yes
C14 . C15 . H151 . 120.4 no
C16 . C15 . H151 . 118.9 no
C15 . C16 . O6 . 126.4(6) yes
C15 . C16 . C17 . 119.0(7) yes
O6 . C16 . C17 . 114.6(6) yes
C16 . C17 . O7 . 115.7(7) yes
C16 . C17 . C18 . 119.0(6) yes
O7 . C17 . C18 . 125.2(6) yes
C17 . C18 . C19 . 121.9(6) yes
C17 . C18 . H181 . 118.3 no
C19 . C18 . H181 . 119.7 no
C14 . C19 . C18 . 119.6(6) yes
C14 . C19 . H191 . 121.1 no
C18 . C19 . H191 . 119.3 no
O6 . C20 . C21 . 106.1(8) yes
O6 . C20 . H201 . 116.6 no
C21 . C20 . H201 . 110.5 no
O6 . C20 . H202 . 107.6 no
C21 . C20 . H202 . 105.5 no
H201 . C20 . H202 . 109.9 no
C20 . C21 . H211 . 112.0 no
C20 . C21 . H212 . 114.0 no
H211 . C21 . H212 . 102.4 no
C20 . C21 . H213 . 112.5 no
H211 . C21 . H213 . 108.0 no
H212 . C21 . H213 . 107.3 no
O7 . C22 . H221 . 106.4 no
O7 . C22 . H222 . 111.0 no
H221 . C22 . H222 . 108.4 no
O7 . C22 . H223 . 109.9 no
H221 . C22 . H223 . 108.7 no
H222 . C22 . H223 . 112.2 no
C67 . O69 . H691 . 117(14) no
Br1 7_556 O68 . C67 . 83.4(8) yes
H621 7_556 C61 . Br1 7_556 133.7 no
H621 7_556 C61 . C63 7_556 152.5 no
Br1 7_556 C61 . C63 7_556 62.5(10) yes
H621 7_556 C61 . C62 7_556 58.6 no
Br1 7_556 C61 . C62 7_556 156.4(13) yes
C63 7_556 C61 . C62 7_556 98.5(18) yes
H621 7_556 C61 . C62 . 66.2 no
Br1 7_556 C61 . C62 . 158.3(9) yes
C63 7_556 C61 . C62 . 95.8(14) yes
C62 7_556 C61 . C62 . 15.4(10) yes
H621 7_556 C61 . C66 . 157.6 no
Br1 7_556 C61 . C66 . 38.8(6) yes
C63 7_556 C61 . C66 . 24.0(11) yes
C62 7_556 C61 . C66 . 120.7(13) yes
C62 . C61 . C66 . 119.6(9) yes
H621 7_556 C61 . C67 . 56.3 no
Br1 7_556 C61 . C67 . 84.4(8) yes
C63 7_556 C61 . C67 . 146.9(15) yes
C62 7_556 C61 . C67 . 114.0(15) yes
C62 . C61 . C67 . 117.2(12) yes
C66 . C61 . C67 . 123.2(11) yes
C65 7_556 C63 . C62 7_556 120.3(12) yes
C65 7_556 C63 . C61 7_556 170.0(17) yes
C62 7_556 C63 . C61 7_556 50.4(9) yes
C65 7_556 C63 . C62 . 136.2(12) yes
C62 7_556 C63 . C62 . 19.3(6) yes
C61 7_556 C63 . C62 . 33.9(11) yes
C65 7_556 C63 . C64 . 22.1(9) yes
C62 7_556 C63 . C64 . 102.5(8) yes
C61 7_556 C63 . C64 . 151.6(13) yes
C62 . C63 . C64 . 120.9(7) yes
C65 7_556 C63 . Br1 . 101.2(10) yes
C62 7_556 C63 . Br1 . 138.3(10) yes
C61 7_556 C63 . Br1 . 88.0(12) yes
C62 . C63 . Br1 . 120.6(9) yes
C64 . C63 . Br1 . 118.5(10) yes
C61 . C62 . C63 . 119.0(6) yes
C61 . C62 . C63 7_556 33.9(9) yes
C63 . C62 . C63 7_556 85.2(9) yes
C61 . C62 . C61 7_556 160.2(14) yes
C63 . C62 . C61 7_556 47.6(14) yes
C63 7_556 C62 . C61 7_556 130.3(11) yes
C61 . C62 . H621 . 118.6 no
C63 . C62 . H621 . 122.3 no
C63 7_556 C62 . H621 . 152.4 no
C61 7_556 C62 . H621 . 76.8 no
C63 7_556 C65 . H641 7_556 138.4 no
C63 7_556 C65 . C65 7_556 96.5(9) yes
H641 7_556 C65 . C65 7_556 92.9 no
C63 7_556 C65 . C64 . 94.0(10) yes
H641 7_556 C65 . C64 . 101.7 no
C65 7_556 C65 . C64 . 11.0(6) yes
C63 7_556 C65 . C66 . 25.8(8) yes
H641 7_556 C65 . C66 . 125.6 no
C65 7_556 C65 . C66 . 122.1(6) yes
C64 . C65 . C66 . 119.7(7) yes
C63 7_556 C65 . H651 . 148.7 no
H641 7_556 C65 . H651 . 37.5 no
C65 7_556 C65 . H651 . 113.7 no
C64 . C65 . H651 . 117.2 no
C66 . C65 . H651 . 123.1 no
C66 7_556 C64 . C65 . 142.0(11) yes
C66 7_556 C64 . C63 . 22.9(9) yes
C65 . C64 . C63 . 119.5(7) yes
C66 7_556 C64 . C64 7_556 131.7(8) yes
C65 . C64 . C64 7_556 18.5(7) yes
C63 . C64 . C64 7_556 112.2(6) yes
C66 7_556 C64 . H641 . 99.2 no
C65 . C64 . H641 . 118.7 no
C63 . C64 . H641 . 121.8 no
C64 7_556 C64 . H641 . 122.9 no
C64 7_556 C66 . C61 . 105.2(8) yes
C64 7_556 C66 . C65 . 19.4(6) yes
C61 . C66 . C65 . 121.3(6) yes
C64 7_556 C66 . Br1 7_556 150.4(13) yes
C61 . C66 . Br1 7_556 100.4(13) yes
C65 . C66 . Br1 7_556 138.2(13) yes
C64 7_556 C66 . H661 . 133.4 no
C61 . C66 . H661 . 119.8 no
C65 . C66 . H661 . 119.0 no
Br1 7_556 C66 . H661 . 19.5 no
C61 . C67 . H621 7_556 44.9 no
C61 . C67 . O69 . 114.3(12) yes
H621 7_556 C67 . O69 . 82.0 no
C61 . C67 . O68 . 123.7(12) yes
H621 7_556 C67 . O68 . 149.1 no
O69 . C67 . O68 . 121.2(7) yes
C63 . Br1 . C61 7_556 29.5(7) yes
C63 . Br1 . O68 7_556 96.7(6) yes
C61 7_556 Br1 . O68 7_556 67.3(5) yes
C63 . Br1 . C66 7_556 11.6(10) yes
C61 7_556 Br1 . C66 7_556 40.8(8) yes
O68 7_556 Br1 . C66 7_556 107.8(9) yes
C61 7_556 H621 . C62 . 44.6 no
C61 7_556 H621 . C67 7_556 78.8 no
C62 . H621 . C67 7_556 122.5 no
H651 7_556 H641 . C64 . 112.8 no
H651 7_556 H641 . C65 7_556 82.7 no
C64 . H641 . C65 7_556 33.0 no
H641 7_556 H651 . C65 . 59.8 no



_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SQRTW        is   0.00
  Minimum value of RATIO        is  -3.00
;
_chemical_name_systematic        
'N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide hemikis(3-bromobenzoic acid)'
_chemical_name_common            'apremilast hemikis(3-bromobenzoic acid)'
_chemical_melting_point          163
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methyl Ethyl Ketone'
####################################################################### 
# 
# 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_APR_4ClBA
_database_code_depnum_ccdc_archive 'CCDC 2477193'
loop_
_audit_author_name
_audit_author_address
'Yelizaveta Naumkina'
;University of Chemistry and Technology Prague
Czech Republic
;
_audit_update_record             
;
2025-07-30 deposited with the CCDC.	2025-10-13 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. 
;


#--------------------------------------------------------------- 
# _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                   13.1247(5)
_cell_length_b                   13.4043(5)
_cell_length_c                   28.9113(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5086.3(3)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
x+1/2,-y+1/2,-z
-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            8

# Given Formula = C25.50 H26.50 Cl0.50 N2 O8 S1 
# Dc =      1.41 Fooo =   2256.00 Mu =     20.73 M =    538.79
# Found Formula = C25.50 H26.50 Cl0.50 N2 O8 S1 
# Dc =      1.41 FOOO =   2255.99 Mu =     20.73 M =    538.79

_chemical_formula_sum            'C25.50 H26.50 Cl0.50 N2 O8 S'
_chemical_formula_moiety         'C22 H24 N2 O7 S, 1/2(C7 H5 Cl O2)'
_chemical_compound_source        .
_chemical_formula_weight         538.79


_cell_measurement_reflns_used    9815
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      72.33
_cell_measurement_temperature    180

_exptl_crystal_description       bipyramidal
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.258
_exptl_crystal_size_mid          0.268
_exptl_crystal_size_max          0.464

_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2255.989
_exptl_absorpt_coefficient_mu    2.073

# Sheldrick geometric approximatio 0.57 0.59 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_T_max  0.59
_diffrn_measurement_device_type  'Bruker Venture D8'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  polycapillary
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_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      180
_diffrn_reflns_number            10039
_diffrn_reflns_av_unetI/netI     0.018
_reflns_number_total             10039
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections without Friedels Law is 10039 
# Number of reflections with Friedels Law is 5579 
# Theoretical number of reflections is about 5030 


_diffrn_reflns_theta_min         3.057
_diffrn_reflns_theta_max         72.347
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        72.347
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       35
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              35

_oxford_diffrn_Wilson_B_factor   2.66
_oxford_diffrn_Wilson_scale      7.59

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

_refine_diff_density_min         -0.41
_refine_diff_density_max         0.19


# 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     10
_refine_ls_number_parameters     680
_refine_ls_number_reflns         10035
_refine_ls_R_factor_ref          0.0306
_refine_ls_wR_factor_ref         0.0837
_refine_ls_goodness_of_fit_ref   1.0114
_refine_ls_shift/su_max          0.0021913
_refine_ls_shift/su_mean         0.0000725


# Computed with I/sigma = -10 
_reflns_number_all               10035
_refine_ls_R_factor_all          0.0306
_refine_ls_wR_factor_all         0.0837

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                10005
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_gt          0.0835

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  0.0002(17) # for 3882 Friedel pairs 
_oxford_Bijvoet_difference       0.0094(19) # for 3882 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.015(8) # for 4460 Friedel pairs 
_refine_ls_abs_structure_Flack   0.0094(19)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 3882 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) + ( 0.05P)² + 1.51P] 
 ,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
S1 S 0.14031(3) 0.18500(3) 0.593915(14) 0.0300 1.0000 Uani . . . . . .
O1 O 0.14677(10) 0.47869(9) 0.56484(4) 0.0336 1.0000 Uani . . . . . .
O2 O 0.21365(9) 0.23600(9) 0.45762(4) 0.0294 1.0000 Uani . . . . . .
O3 O -0.06084(12) 0.29855(12) 0.33098(5) 0.0489 1.0000 Uani . . . . . .
O4 O 0.05111(10) 0.22740(10) 0.57237(5) 0.0388 1.0000 Uani . . . . . .
O5 O 0.18188(12) 0.09526(10) 0.57412(5) 0.0443 1.0000 Uani . . . . . .
O6 O 0.49696(10) 0.55714(11) 0.62794(5) 0.0398 1.0000 Uani . . . . . .
O7 O 0.62965(10) 0.54996(10) 0.56243(5) 0.0405 1.0000 Uani . . . . . .
N1 N 0.20064(10) 0.34827(10) 0.51846(4) 0.0245 1.0000 Uani . . . . . .
N2 N 0.05664(12) 0.28082(11) 0.38780(5) 0.0301 1.0000 Uani D . . . . .
C1 C 0.02793(13) 0.35553(13) 0.41903(6) 0.0272 1.0000 Uani D . . . . .
C2 C -0.05115(14) 0.42439(14) 0.41229(6) 0.0340 1.0000 Uani . . . . . .
C3 C -0.07068(14) 0.49825(15) 0.44485(7) 0.0368 1.0000 Uani . . . . . .
C4 C -0.01321(14) 0.50845(14) 0.48524(6) 0.0331 1.0000 Uani . . . . . .
C5 C 0.06337(12) 0.43970(12) 0.49158(5) 0.0264 1.0000 Uani . . . . . .
C6 C 0.13821(13) 0.42885(12) 0.53005(5) 0.0264 1.0000 Uani . . . . . .
C7 C 0.17188(12) 0.30629(11) 0.47593(5) 0.0237 1.0000 Uani . . . . . .
C8 C 0.08353(12) 0.36512(12) 0.45965(5) 0.0246 1.0000 Uani . . . . . .
C9 C 0.01525(15) 0.25815(15) 0.34579(6) 0.0347 1.0000 Uani D . . . . .
C10 C 0.07257(17) 0.18024(17) 0.31903(7) 0.0445 1.0000 Uani . . . . . .
C11 C 0.27975(12) 0.30391(12) 0.54832(5) 0.0255 1.0000 Uani . . . . . .
C12 C 0.23735(13) 0.27676(12) 0.59598(6) 0.0268 1.0000 Uani . . . . . .
C13 C 0.11347(18) 0.16539(17) 0.65260(7) 0.0463 1.0000 Uani . . . . . .
C14 C 0.37289(13) 0.37067(12) 0.55215(6) 0.0263 1.0000 Uani . . . . . .
C15 C 0.38793(12) 0.43448(12) 0.59021(6) 0.0278 1.0000 Uani . . . . . .
C16 C 0.47444(13) 0.49297(13) 0.59270(6) 0.0304 1.0000 Uani . . . . . .
C17 C 0.54687(13) 0.48931(13) 0.55675(6) 0.0305 1.0000 Uani . . . . . .
C18 C 0.53132(13) 0.42697(13) 0.51935(6) 0.0318 1.0000 Uani . . . . . .
C19 C 0.44489(13) 0.36740(13) 0.51727(6) 0.0297 1.0000 Uani . . . . . .
C20 C 0.42549(14) 0.56341(16) 0.66563(7) 0.0379 1.0000 Uani . . . . . .
C21 C 0.4623(2) 0.6425(3) 0.69835(11) 0.0784 1.0000 Uani . . . . . .
C22 C 0.70622(14) 0.54605(16) 0.52700(7) 0.0398 1.0000 Uani . . . . . .
H21 H -0.0895 0.4201 0.3854 0.0412 1.0000 Uiso R . . . . .
H22 H 0.1045(14) 0.2438(14) 0.3967(6) 0.0363(19) 1.0000 Uiso D . . . . .
H31 H -0.1241 0.5420 0.4396 0.0427 1.0000 Uiso R . . . . .
H41 H -0.0247 0.5614 0.5065 0.0401 1.0000 Uiso R . . . . .
H101 H 0.0934 0.1266 0.3374 0.0677 1.0000 Uiso R . . . . .
H102 H 0.1310 0.2109 0.3042 0.0695 1.0000 Uiso R . . . . .
H103 H 0.0276 0.1558 0.2953 0.0671 1.0000 Uiso R . . . . .
H111 H 0.3010 0.2430 0.5337 0.0312 1.0000 Uiso R . . . . .
H121 H 0.2108 0.3323 0.6119 0.0321 1.0000 Uiso R . . . . .
H122 H 0.2919 0.2465 0.6131 0.0315 1.0000 Uiso R . . . . .
H131 H 0.0612 0.1139 0.6542 0.0714 1.0000 Uiso R . . . . .
H132 H 0.1752 0.1410 0.6670 0.0695 1.0000 Uiso R . . . . .
H133 H 0.0884 0.2290 0.6674 0.0702 1.0000 Uiso R . . . . .
H151 H 0.3395 0.4371 0.6133 0.0329 1.0000 Uiso R . . . . .
H181 H 0.5794 0.4228 0.4950 0.0393 1.0000 Uiso R . . . . .
H191 H 0.4348 0.3221 0.4925 0.0361 1.0000 Uiso R . . . . .
H201 H 0.4236 0.4977 0.6804 0.0454 1.0000 Uiso R . . . . .
H202 H 0.3585 0.5801 0.6540 0.0444 1.0000 Uiso R . . . . .
H211 H 0.4157 0.6463 0.7240 0.1158 1.0000 Uiso R . . . . .
H212 H 0.5278 0.6239 0.7097 0.1168 1.0000 Uiso R . . . . .
H213 H 0.4682 0.7069 0.6828 0.1167 1.0000 Uiso R . . . . .
H221 H 0.7560 0.5913 0.5369 0.0583 1.0000 Uiso R . . . . .
H222 H 0.7366 0.4796 0.5251 0.0591 1.0000 Uiso R . . . . .
H223 H 0.6793 0.5670 0.4982 0.0584 1.0000 Uiso R . . . . .
S31 S -0.09230(3) 0.43626(3) 0.660500(14) 0.0303 1.0000 Uani . . . . . .
O31 O 0.21521(9) 0.44151(10) 0.67458(4) 0.0337 1.0000 Uani . . . . . .
O32 O -0.01466(9) 0.49932(9) 0.79038(4) 0.0309 1.0000 Uani . . . . . .
O33 O 0.08030(12) 0.22414(11) 0.91246(4) 0.0425 1.0000 Uani . . . . . .
O34 O -0.04558(11) 0.35052(10) 0.68189(5) 0.0393 1.0000 Uani . . . . . .
O35 O -0.17948(11) 0.47894(12) 0.68313(6) 0.0470 1.0000 Uani . . . . . .
O36 O 0.28989(10) 0.77247(10) 0.60584(4) 0.0356 1.0000 Uani . . . . . .
O37 O 0.30208(11) 0.90567(10) 0.67098(5) 0.0404 1.0000 Uani . . . . . .
N31 N 0.09222(10) 0.49348(10) 0.72661(4) 0.0252 1.0000 Uani . . . . . .
N32 N 0.04495(11) 0.34084(11) 0.85726(5) 0.0280 1.0000 Uani D . . . . .
C31 C 0.11420(12) 0.31532(13) 0.82261(5) 0.0265 1.0000 Uani D . . . . .
C32 C 0.18227(14) 0.23452(13) 0.82432(6) 0.0324 1.0000 Uani . . . . . .
C33 C 0.25049(14) 0.21698(14) 0.78849(7) 0.0354 1.0000 Uani . . . . . .
C34 C 0.25609(13) 0.27782(14) 0.74970(6) 0.0325 1.0000 Uani . . . . . .
C35 C 0.18782(12) 0.35586(12) 0.74791(6) 0.0276 1.0000 Uani . . . . . .
C36 C 0.17114(12) 0.43217(12) 0.71152(5) 0.0263 1.0000 Uani . . . . . .
C37 C 0.05559(12) 0.46120(12) 0.76964(5) 0.0240 1.0000 Uani . . . . . .
C38 C 0.11803(12) 0.37417(12) 0.78285(5) 0.0248 1.0000 Uani . . . . . .
C39 C 0.03375(14) 0.29780(13) 0.90019(6) 0.0314 1.0000 Uani D . . . . .
C40 C -0.04044(16) 0.35181(15) 0.93108(6) 0.0385 1.0000 Uani . . . . . .
C41 C 0.04237(12) 0.57138(12) 0.69859(5) 0.0255 1.0000 Uani . . . . . .
C42 C 0.00223(13) 0.52919(13) 0.65287(6) 0.0271 1.0000 Uani . . . . . .
C43 C -0.12405(18) 0.40557(17) 0.60290(7) 0.0453 1.0000 Uani . . . . . .
C44 C 0.11211(13) 0.66068(12) 0.69077(6) 0.0264 1.0000 Uani . . . . . .
C45 C 0.16840(13) 0.67273(12) 0.64985(6) 0.0276 1.0000 Uani . . . . . .
C46 C 0.23140(13) 0.75498(13) 0.64407(6) 0.0284 1.0000 Uani . . . . . .
C47 C 0.23886(13) 0.82704(13) 0.67948(6) 0.0295 1.0000 Uani . . . . . .
C48 C 0.18207(14) 0.81497(13) 0.71950(6) 0.0308 1.0000 Uani . . . . . .
C49 C 0.11833(14) 0.73242(13) 0.72494(6) 0.0296 1.0000 Uani . . . . . .
C50 C 0.28858(15) 0.69819(13) 0.56991(6) 0.0327 1.0000 Uani . . . . . .
C51 C 0.36909(17) 0.72694(17) 0.53526(7) 0.0441 1.0000 Uani . . . . . .
C52 C 0.3127(2) 0.97635(15) 0.70761(7) 0.0479 1.0000 Uani . . . . . .
H321 H 0.1841 0.1923 0.8506 0.0401 1.0000 Uiso R . . . . .
H322 H 0.0127(15) 0.3949(13) 0.8532(6) 0.0336(19) 1.0000 Uiso D . . . . .
H331 H 0.2932 0.1631 0.7918 0.0415 1.0000 Uiso R . . . . .
H341 H 0.3037 0.2653 0.7260 0.0396 1.0000 Uiso R . . . . .
H401 H -0.0088 0.4105 0.9441 0.0569 1.0000 Uiso R . . . . .
H402 H -0.0967 0.3718 0.9145 0.0603 1.0000 Uiso R . . . . .
H403 H -0.0594 0.3122 0.9562 0.0580 1.0000 Uiso R . . . . .
H411 H -0.0146 0.5917 0.7168 0.0312 1.0000 Uiso R . . . . .
H421 H -0.0261 0.5832 0.6350 0.0328 1.0000 Uiso R . . . . .
H422 H 0.0566 0.5003 0.6354 0.0333 1.0000 Uiso R . . . . .
H431 H -0.1412 0.4656 0.5869 0.0677 1.0000 Uiso R . . . . .
H432 H -0.1786 0.3594 0.6044 0.0672 1.0000 Uiso R . . . . .
H433 H -0.0658 0.3737 0.5889 0.0694 1.0000 Uiso R . . . . .
H451 H 0.1636 0.6242 0.6265 0.0332 1.0000 Uiso R . . . . .
H481 H 0.1844 0.8621 0.7430 0.0365 1.0000 Uiso R . . . . .
H491 H 0.0800 0.7255 0.7515 0.0363 1.0000 Uiso R . . . . .
H501 H 0.2231 0.6970 0.5571 0.0386 1.0000 Uiso R . . . . .
H502 H 0.3027 0.6320 0.5811 0.0377 1.0000 Uiso R . . . . .
H511 H 0.3752 0.6757 0.5117 0.0671 1.0000 Uiso R . . . . .
H512 H 0.3482 0.7895 0.5196 0.0670 1.0000 Uiso R . . . . .
H513 H 0.4347 0.7346 0.5497 0.0671 1.0000 Uiso R . . . . .
H521 H 0.3596 1.0279 0.6976 0.0707 1.0000 Uiso R . . . . .
H522 H 0.2453 1.0055 0.7135 0.0720 1.0000 Uiso R . . . . .
H523 H 0.3374 0.9441 0.7352 0.0715 1.0000 Uiso R . . . . .
Cl1 Cl 0.81814(5) 1.17044(4) 0.66078(3) 0.0636 1.0000 Uani . . . . . .
O68 O 0.66064(16) 0.78178(13) 0.53322(6) 0.0611 1.0000 Uani . . . . . .
O69 O 0.61630(14) 0.73746(12) 0.60520(6) 0.0561 1.0000 Uani D . . . . .
C61 C 0.68908(15) 0.89464(14) 0.59560(7) 0.0369 1.0000 Uani . . . . . .
C62 C 0.65503(17) 0.92433(15) 0.63889(7) 0.0430 1.0000 Uani . . . . . .
C63 C 0.69337(18) 1.01062(16) 0.65908(8) 0.0461 1.0000 Uani . . . . . .
C64 C 0.76653(16) 1.06434(14) 0.63528(8) 0.0421 1.0000 Uani . . . . . .
C65 C 0.80052(16) 1.03714(15) 0.59245(8) 0.0443 1.0000 Uani . . . . . .
C66 C 0.76038(16) 0.95180(15) 0.57213(8) 0.0412 1.0000 Uani . . . . . .
C67 C 0.65420(17) 0.79990(15) 0.57387(8) 0.0448 1.0000 Uani . . . . . .
H621 H 0.6035 0.8880 0.6552 0.0502 1.0000 Uiso R . . . . .
H631 H 0.6697 1.0331 0.6874 0.0540 1.0000 Uiso R . . . . .
H651 H 0.8551 1.0778 0.5784 0.0532 1.0000 Uiso R . . . . .
H661 H 0.7858 0.9311 0.5410 0.0487 1.0000 Uiso R . . . . .
H691 H 0.590(2) 0.6821(18) 0.5962(12) 0.086(2) 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4004(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
S1 . O4 . 1.4428(14) yes
S1 . O5 . 1.4395(15) yes
S1 . C12 . 1.7716(16) yes
S1 . C13 . 1.753(2) yes
O1 . C6 . 1.213(2) yes
O2 . C7 . 1.212(2) yes
O3 . C9 . 1.214(2) yes
O6 . C16 . 1.366(2) yes
O6 . C20 . 1.440(2) yes
O7 . C17 . 1.367(2) yes
O7 . C22 . 1.436(2) yes
N1 . C6 . 1.396(2) yes
N1 . C7 . 1.404(2) yes
N1 . C11 . 1.475(2) yes
N2 . C1 . 1.400(2) yes
N2 . C9 . 1.365(2) yes
N2 . H22 . 0.841(15) no
C1 . C2 . 1.403(2) yes
C1 . C8 . 1.389(2) yes
C2 . C3 . 1.390(3) yes
C2 . H21 . 0.927 no
C3 . C4 . 1.397(3) yes
C3 . H31 . 0.926 no
C4 . C5 . 1.376(2) yes
C4 . H41 . 0.951 no
C5 . C6 . 1.491(2) yes
C5 . C8 . 1.386(2) yes
C7 . C8 . 1.479(2) yes
C9 . C10 . 1.502(3) yes
C10 . H101 . 0.934 no
C10 . H102 . 0.970 no
C10 . H103 . 0.962 no
C11 . C12 . 1.530(2) yes
C11 . C14 . 1.519(2) yes
C11 . H111 . 0.962 no
C12 . H121 . 0.942 no
C12 . H122 . 0.961 no
C13 . H131 . 0.974 no
C13 . H132 . 0.968 no
C13 . H133 . 1.008 no
C14 . C15 . 1.408(2) yes
C14 . C19 . 1.383(2) yes
C15 . C16 . 1.382(2) yes
C15 . H151 . 0.923 no
C16 . C17 . 1.409(2) yes
C17 . C18 . 1.382(3) yes
C18 . C19 . 1.389(3) yes
C18 . H181 . 0.948 no
C19 . H191 . 0.949 no
C20 . C21 . 1.501(3) yes
C20 . H201 . 0.979 no
C20 . H202 . 0.968 no
C21 . H211 . 0.962 no
C21 . H212 . 0.953 no
C21 . H213 . 0.977 no
C22 . H221 . 0.936 no
C22 . H222 . 0.977 no
C22 . H223 . 0.948 no
S31 . O34 . 1.4420(14) yes
S31 . O35 . 1.4369(15) yes
S31 . C42 . 1.7719(16) yes
S31 . C43 . 1.7653(19) yes
O31 . C36 . 1.221(2) yes
O32 . C37 . 1.213(2) yes
O33 . C39 . 1.214(2) yes
O36 . C46 . 1.366(2) yes
O36 . C50 . 1.439(2) yes
O37 . C47 . 1.364(2) yes
O37 . C52 . 1.428(2) yes
N31 . C36 . 1.392(2) yes
N31 . C37 . 1.402(2) yes
N31 . C41 . 1.475(2) yes
N32 . C31 . 1.395(2) yes
N32 . C39 . 1.377(2) yes
N32 . H322 . 0.847(15) no
C31 . C32 . 1.405(2) yes
C31 . C38 . 1.395(2) yes
C32 . C33 . 1.389(3) yes
C32 . H321 . 0.949 no
C33 . C34 . 1.389(3) yes
C33 . H331 . 0.920 no
C34 . C35 . 1.378(2) yes
C34 . H341 . 0.942 no
C35 . C36 . 1.483(2) yes
C35 . C38 . 1.385(2) yes
C37 . C38 . 1.476(2) yes
C39 . C40 . 1.507(3) yes
C40 . H401 . 0.965 no
C40 . H402 . 0.921 no
C40 . H403 . 0.933 no
C41 . C42 . 1.531(2) yes
C41 . C44 . 1.524(2) yes
C41 . H411 . 0.954 no
C42 . H421 . 0.965 no
C42 . H422 . 0.956 no
C43 . H431 . 0.955 no
C43 . H432 . 0.947 no
C43 . H433 . 0.965 no
C44 . C45 . 1.404(2) yes
C44 . C49 . 1.381(2) yes
C45 . C46 . 1.388(2) yes
C45 . H451 . 0.939 no
C46 . C47 . 1.411(2) yes
C47 . C48 . 1.386(2) yes
C48 . C49 . 1.396(2) yes
C48 . H481 . 0.929 no
C49 . H491 . 0.923 no
C50 . C51 . 1.506(2) yes
C50 . H501 . 0.937 no
C50 . H502 . 0.963 no
C51 . H511 . 0.971 no
C51 . H512 . 0.992 no
C51 . H513 . 0.962 no
C52 . H521 . 0.970 no
C52 . H522 . 0.982 no
C52 . H523 . 0.964 no
Cl1 . C64 . 1.739(2) yes
O68 . C67 . 1.203(3) yes
O69 . C67 . 1.330(3) yes
O69 . H691 . 0.861(18) no
C61 . C62 . 1.387(3) yes
C61 . C66 . 1.387(3) yes
C61 . C67 . 1.489(3) yes
C62 . C63 . 1.390(3) yes
C62 . H621 . 0.957 no
C63 . C64 . 1.383(3) yes
C63 . H631 . 0.927 no
C64 . C65 . 1.366(3) yes
C65 . C66 . 1.390(3) yes
C65 . H651 . 0.988 no
C66 . H661 . 0.999 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
O4 . S1 . O5 . 117.72(9) yes
O4 . S1 . C12 . 108.93(8) yes
O5 . S1 . C12 . 108.73(9) yes
O4 . S1 . C13 . 108.29(10) yes
O5 . S1 . C13 . 109.61(10) yes
C12 . S1 . C13 . 102.47(9) yes
C16 . O6 . C20 . 117.41(13) yes
C17 . O7 . C22 . 116.68(15) yes
C6 . N1 . C7 . 111.25(13) yes
C6 . N1 . C11 . 125.74(13) yes
C7 . N1 . C11 . 122.69(13) yes
C1 . N2 . C9 . 128.76(16) yes
C1 . N2 . H22 . 115.2(10) no
C9 . N2 . H22 . 116.0(11) no
N2 . C1 . C2 . 125.48(16) yes
N2 . C1 . C8 . 118.05(15) yes
C2 . C1 . C8 . 116.45(15) yes
C1 . C2 . C3 . 120.74(16) yes
C1 . C2 . H21 . 118.5 no
C3 . C2 . H21 . 120.8 no
C2 . C3 . C4 . 122.43(17) yes
C2 . C3 . H31 . 118.7 no
C4 . C3 . H31 . 118.9 no
C3 . C4 . C5 . 116.12(16) yes
C3 . C4 . H41 . 121.9 no
C5 . C4 . H41 . 121.9 no
C4 . C5 . C6 . 130.24(15) yes
C4 . C5 . C8 . 122.27(15) yes
C6 . C5 . C8 . 107.49(14) yes
C5 . C6 . N1 . 106.44(13) yes
C5 . C6 . O1 . 128.76(15) yes
N1 . C6 . O1 . 124.80(15) yes
N1 . C7 . O2 . 124.93(15) yes
N1 . C7 . C8 . 106.01(13) yes
O2 . C7 . C8 . 129.06(15) yes
C7 . C8 . C1 . 129.17(15) yes
C7 . C8 . C5 . 108.80(14) yes
C1 . C8 . C5 . 121.98(15) yes
N2 . C9 . O3 . 122.82(18) yes
N2 . C9 . C10 . 114.46(17) yes
O3 . C9 . C10 . 122.72(17) yes
C9 . C10 . H101 . 112.9 no
C9 . C10 . H102 . 109.2 no
H101 . C10 . H102 . 110.2 no
C9 . C10 . H103 . 107.3 no
H101 . C10 . H103 . 108.8 no
H102 . C10 . H103 . 108.3 no
N1 . C11 . C12 . 111.52(13) yes
N1 . C11 . C14 . 111.81(13) yes
C12 . C11 . C14 . 111.55(13) yes
N1 . C11 . H111 . 106.8 no
C12 . C11 . H111 . 107.5 no
C14 . C11 . H111 . 107.4 no
C11 . C12 . S1 . 113.34(11) yes
C11 . C12 . H121 . 112.7 no
S1 . C12 . H121 . 107.4 no
C11 . C12 . H122 . 107.2 no
S1 . C12 . H122 . 105.0 no
H121 . C12 . H122 . 110.9 no
S1 . C13 . H131 . 107.1 no
S1 . C13 . H132 . 107.5 no
H131 . C13 . H132 . 109.2 no
S1 . C13 . H133 . 110.4 no
H131 . C13 . H133 . 110.4 no
H132 . C13 . H133 . 112.1 no
C11 . C14 . C15 . 121.85(14) yes
C11 . C14 . C19 . 118.58(15) yes
C15 . C14 . C19 . 119.57(16) yes
C14 . C15 . C16 . 120.04(15) yes
C14 . C15 . H151 . 119.4 no
C16 . C15 . H151 . 120.5 no
C15 . C16 . O6 . 125.02(15) yes
C15 . C16 . C17 . 119.76(16) yes
O6 . C16 . C17 . 115.22(15) yes
C16 . C17 . O7 . 115.27(16) yes
C16 . C17 . C18 . 119.89(16) yes
O7 . C17 . C18 . 124.83(16) yes
C17 . C18 . C19 . 120.16(16) yes
C17 . C18 . H181 . 121.3 no
C19 . C18 . H181 . 118.6 no
C18 . C19 . C14 . 120.57(16) yes
C18 . C19 . H191 . 121.0 no
C14 . C19 . H191 . 118.4 no
O6 . C20 . C21 . 107.99(17) yes
O6 . C20 . H201 . 107.1 no
C21 . C20 . H201 . 111.7 no
O6 . C20 . H202 . 110.1 no
C21 . C20 . H202 . 110.3 no
H201 . C20 . H202 . 109.6 no
C20 . C21 . H211 . 108.6 no
C20 . C21 . H212 . 108.8 no
H211 . C21 . H212 . 108.9 no
C20 . C21 . H213 . 111.0 no
H211 . C21 . H213 . 111.0 no
H212 . C21 . H213 . 108.5 no
O7 . C22 . H221 . 104.2 no
O7 . C22 . H222 . 111.0 no
H221 . C22 . H222 . 108.9 no
O7 . C22 . H223 . 110.8 no
H221 . C22 . H223 . 109.7 no
H222 . C22 . H223 . 111.9 no
O34 . S31 . O35 . 117.43(9) yes
O34 . S31 . C42 . 108.41(8) yes
O35 . S31 . C42 . 109.53(9) yes
O34 . S31 . C43 . 108.62(10) yes
O35 . S31 . C43 . 109.54(11) yes
C42 . S31 . C43 . 102.22(9) yes
C46 . O36 . C50 . 117.30(13) yes
C47 . O37 . C52 . 116.01(15) yes
C36 . N31 . C37 . 110.53(13) yes
C36 . N31 . C41 . 125.17(13) yes
C37 . N31 . C41 . 123.63(13) yes
C31 . N32 . C39 . 127.89(15) yes
C31 . N32 . H322 . 115.8(10) no
C39 . N32 . H322 . 115.5(10) no
N32 . C31 . C32 . 125.31(15) yes
N32 . C31 . C38 . 118.46(15) yes
C32 . C31 . C38 . 116.23(15) yes
C31 . C32 . C33 . 120.94(16) yes
C31 . C32 . H321 . 120.3 no
C33 . C32 . H321 . 118.7 no
C32 . C33 . C34 . 122.47(17) yes
C32 . C33 . H331 . 116.7 no
C34 . C33 . H331 . 120.8 no
C33 . C34 . C35 . 116.21(16) yes
C33 . C34 . H341 . 121.1 no
C35 . C34 . H341 . 122.7 no
C34 . C35 . C36 . 130.23(15) yes
C34 . C35 . C38 . 122.47(16) yes
C36 . C35 . C38 . 107.30(14) yes
C35 . C36 . N31 . 107.14(13) yes
C35 . C36 . O31 . 128.40(16) yes
N31 . C36 . O31 . 124.45(16) yes
N31 . C37 . O32 . 124.71(15) yes
N31 . C37 . C38 . 106.44(13) yes
O32 . C37 . C38 . 128.85(15) yes
C37 . C38 . C31 . 129.80(15) yes
C37 . C38 . C35 . 108.57(14) yes
C31 . C38 . C35 . 121.63(15) yes
N32 . C39 . O33 . 123.40(17) yes
N32 . C39 . C40 . 113.70(16) yes
O33 . C39 . C40 . 122.88(16) yes
C39 . C40 . H401 . 110.1 no
C39 . C40 . H402 . 110.4 no
H401 . C40 . H402 . 108.1 no
C39 . C40 . H403 . 111.2 no
H401 . C40 . H403 . 106.0 no
H402 . C40 . H403 . 110.9 no
N31 . C41 . C42 . 111.43(13) yes
N31 . C41 . C44 . 111.79(13) yes
C42 . C41 . C44 . 111.64(13) yes
N31 . C41 . H411 . 104.3 no
C42 . C41 . H411 . 108.2 no
C44 . C41 . H411 . 109.1 no
C41 . C42 . S31 . 113.15(11) yes
C41 . C42 . H421 . 108.6 no
S31 . C42 . H421 . 108.9 no
C41 . C42 . H422 . 110.5 no
S31 . C42 . H422 . 107.7 no
H421 . C42 . H422 . 107.9 no
S31 . C43 . H431 . 108.4 no
S31 . C43 . H432 . 106.7 no
H431 . C43 . H432 . 113.2 no
S31 . C43 . H433 . 108.2 no
H431 . C43 . H433 . 110.9 no
H432 . C43 . H433 . 109.1 no
C41 . C44 . C45 . 122.10(14) yes
C41 . C44 . C49 . 118.45(14) yes
C45 . C44 . C49 . 119.44(15) yes
C44 . C45 . C46 . 120.42(15) yes
C44 . C45 . H451 . 119.3 no
C46 . C45 . H451 . 120.2 no
C45 . C46 . O36 . 124.64(15) yes
C45 . C46 . C47 . 119.84(15) yes
O36 . C46 . C47 . 115.51(15) yes
C46 . C47 . O37 . 116.13(15) yes
C46 . C47 . C48 . 119.25(15) yes
O37 . C47 . C48 . 124.61(15) yes
C47 . C48 . C49 . 120.60(15) yes
C47 . C48 . H481 . 120.9 no
C49 . C48 . H481 . 118.5 no
C48 . C49 . C44 . 120.44(15) yes
C48 . C49 . H491 . 120.0 no
C44 . C49 . H491 . 119.6 no
O36 . C50 . C51 . 107.14(15) yes
O36 . C50 . H501 . 108.0 no
C51 . C50 . H501 . 112.7 no
O36 . C50 . H502 . 113.2 no
C51 . C50 . H502 . 108.9 no
H501 . C50 . H502 . 107.1 no
C50 . C51 . H511 . 110.1 no
C50 . C51 . H512 . 109.0 no
H511 . C51 . H512 . 107.4 no
C50 . C51 . H513 . 111.5 no
H511 . C51 . H513 . 107.8 no
H512 . C51 . H513 . 110.8 no
O37 . C52 . H521 . 108.2 no
O37 . C52 . H522 . 107.8 no
H521 . C52 . H522 . 110.0 no
O37 . C52 . H523 . 110.4 no
H521 . C52 . H523 . 110.7 no
H522 . C52 . H523 . 109.7 no
C67 . O69 . H691 . 119(2) no
C62 . C61 . C66 . 120.01(18) yes
C62 . C61 . C67 . 121.76(19) yes
C66 . C61 . C67 . 118.18(19) yes
C61 . C62 . C63 . 120.1(2) yes
C61 . C62 . H621 . 121.7 no
C63 . C62 . H621 . 118.2 no
C62 . C63 . C64 . 118.4(2) yes
C62 . C63 . H631 . 121.4 no
C64 . C63 . H631 . 120.2 no
Cl1 . C64 . C63 . 119.01(17) yes
Cl1 . C64 . C65 . 118.38(17) yes
C63 . C64 . C65 . 122.60(19) yes
C64 . C65 . C66 . 118.6(2) yes
C64 . C65 . H651 . 117.6 no
C66 . C65 . H651 . 123.7 no
C65 . C66 . C61 . 120.3(2) yes
C65 . C66 . H661 . 118.8 no
C61 . C66 . H661 . 120.9 no
C61 . C67 . O69 . 111.37(18) yes
C61 . C67 . O68 . 124.3(2) yes
O69 . C67 . O68 . 124.4(2) yes



_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SQRTW        is   0.00
  Minimum value of RATIO        is  -3.00
;

# 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
1 1 7 x .
-1 2 2 x .
3 1 3 x .
0 1 3 x .
_chemical_name_systematic        
'bis(N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide) 4-chlorobenzoic acid'
_chemical_name_common            'bis(apremilast) 4-chlorobenzoic acid'
_chemical_melting_point          147
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methyl Ethyl Ketone'
####################################################################### 
# 
# 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_APR_4BrBA
_database_code_depnum_ccdc_archive 'CCDC 2477192'
loop_
_audit_author_name
_audit_author_address
'Yelizaveta Naumkina'
;University of Chemistry and Technology Prague
Czech Republic
;
_audit_update_record             
;
2025-07-30 deposited with the CCDC.	2025-10-13 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. 
;


#--------------------------------------------------------------- 
# _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                   13.2266(3)
_cell_length_b                   13.4694(3)
_cell_length_c                   28.8772(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5144.6(2)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
x+1/2,-y+1/2,-z
-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'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C25.50 H26.50 Br0.50 N2 O8 S1 
# Dc =      1.45 Fooo =   2328.00 Mu =     24.81 M =    561.02
# Found Formula = C25.50 H26.50 Br0.50 N2 O8 S1 
# Dc =      1.45 FOOO =   2327.99 Mu =     24.81 M =    561.02

_chemical_formula_sum            'C25.50 H26.50 Br0.50 N2 O8 S'
_chemical_formula_moiety         'C22 H24 N2 O7 S, 1/2(C7 H5 Br O2)'
_chemical_compound_source        .
_chemical_formula_weight         561.02


_cell_measurement_reflns_used    9838
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      42.39
_cell_measurement_temperature    180

_exptl_crystal_description       bipyramidal
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.160
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2327.987
_exptl_absorpt_coefficient_mu    2.481

# Sheldrick geometric approximatio 0.67 0.67 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_T_max  0.67
_diffrn_measurement_device_type  'Bruker Venture D8'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  polycapillary
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_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      180
_diffrn_reflns_number            10186
_diffrn_reflns_av_unetI/netI     0.023
_reflns_number_total             10186
_diffrn_reflns_av_R_equivalents  0.0389
# Number of reflections without Friedels Law is 10186 
# Number of reflections with Friedels Law is 5651 
# Theoretical number of reflections is about 5090 


_diffrn_reflns_theta_min         3.061
_diffrn_reflns_theta_max         72.382
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        72.382
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       35
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              35

_oxford_diffrn_Wilson_B_factor   2.88
_oxford_diffrn_Wilson_scale      13.30

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

_refine_diff_density_min         -0.86
_refine_diff_density_max         0.67


# 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     10
_refine_ls_number_parameters     680
_refine_ls_number_reflns         10180
_refine_ls_R_factor_ref          0.0423
_refine_ls_wR_factor_ref         0.1185
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_shift/su_max          0.0004565
_refine_ls_shift/su_mean         0.0000579


# Computed with I/sigma = -10 
_reflns_number_all               10180
_refine_ls_R_factor_all          0.0423
_refine_ls_wR_factor_all         0.1185

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                9877
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_gt          0.1181

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  -0.002(5) # for 4003 Friedel pairs 
_oxford_Bijvoet_difference       0.001(2) # for 4003 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          -0.003(13) # for 4535 Friedel pairs 
_refine_ls_abs_structure_Flack   0.001(2)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 4003 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) + ( 0.08P)² + 4.03P] 
 ,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
H22 H 0.898(2) -0.255(2) 0.6049(8) 0.036(2) 1.0000 Uiso D . . . . .
H320 H -0.009(2) 0.895(2) 0.1483(8) 0.031(2) 1.0000 Uiso D . . . . .
O69 O 0.3848(2) 0.2317(2) 0.39641(10) 0.0528 1.0000 Uani D . . . . .
O68 O 0.3433(3) 0.2761(2) 0.46864(10) 0.0583 1.0000 Uani . . . . . .
C61 C 0.3159(2) 0.3901(2) 0.40639(11) 0.0351 1.0000 Uani . . . . . .
C62 C 0.3515(3) 0.4192(3) 0.36294(13) 0.0425 1.0000 Uani . . . . . .
C63 C 0.3143(3) 0.5052(3) 0.34288(13) 0.0441 1.0000 Uani . . . . . .
C64 C 0.2418(3) 0.5593(2) 0.36631(13) 0.0398 1.0000 Uani . . . . . .
C65 C 0.2068(3) 0.5323(3) 0.40898(13) 0.0413 1.0000 Uani . . . . . .
C66 C 0.2459(3) 0.4469(3) 0.42958(12) 0.0396 1.0000 Uani . . . . . .
C67 C 0.3499(3) 0.2941(3) 0.42755(13) 0.0427 1.0000 Uani . . . . . .
H621 H 0.4017 0.3817 0.3473 0.0501 1.0000 Uiso R . . . . .
H631 H 0.3392 0.5278 0.3139 0.0525 1.0000 Uiso R . . . . .
H651 H 0.1571 0.5709 0.4234 0.0497 1.0000 Uiso R . . . . .
H661 H 0.2217 0.4281 0.4605 0.0480 1.0000 Uiso R . . . . .
Br70 Br 0.18516(3) 0.67344(3) 0.338294(19) 0.0617 1.0000 Uani . . . . . .
S1 S 0.86402(5) -0.31091(5) 0.40524(2) 0.0278 1.0000 Uani . . . . . .
O1 O 0.85725(17) -0.02023(16) 0.43600(7) 0.0319 1.0000 Uani . . . . . .
O2 O 0.79218(15) -0.26382(15) 0.54276(6) 0.0282 1.0000 Uani . . . . . .
O3 O 1.0675(2) -0.2049(2) 0.66866(9) 0.0500 1.0000 Uani . . . . . .
O4 O 0.95254(16) -0.26942(18) 0.42685(8) 0.0357 1.0000 Uani . . . . . .
O5 O 0.82378(19) -0.40148(17) 0.42436(9) 0.0423 1.0000 Uani . . . . . .
O6 O 0.50696(17) 0.05694(18) 0.37447(8) 0.0379 1.0000 Uani . . . . . .
O7 O 0.37529(17) 0.04647(18) 0.43976(8) 0.0382 1.0000 Uani . . . . . .
N1 N 0.80465(17) -0.15101(17) 0.48215(7) 0.0226 1.0000 Uani . . . . . .
N2 N 0.94922(19) -0.2202(2) 0.61238(8) 0.0304 1.0000 Uani D . . . . .
C1 C 0.9771(2) -0.1465(2) 0.58123(10) 0.0280 1.0000 Uani D . . . . .
C2 C 1.0566(2) -0.0779(2) 0.58780(11) 0.0335 1.0000 Uani . . . . . .
C3 C 1.0752(2) -0.0033(3) 0.55567(12) 0.0371 1.0000 Uani . . . . . .
C4 C 1.0176(2) 0.0075(2) 0.51537(11) 0.0324 1.0000 Uani . . . . . .
C5 C 0.9411(2) -0.0615(2) 0.50912(9) 0.0253 1.0000 Uani . . . . . .
C6 C 0.8659(2) -0.0706(2) 0.47066(9) 0.0255 1.0000 Uani . . . . . .
C7 C 0.83328(19) -0.1936(2) 0.52445(9) 0.0223 1.0000 Uani . . . . . .
C8 C 0.9212(2) -0.1354(2) 0.54097(9) 0.0242 1.0000 Uani . . . . . .
C9 C 0.9912(2) -0.2446(3) 0.65405(10) 0.0338 1.0000 Uani D . . . . .
C10 C 0.9345(3) -0.3228(3) 0.68092(12) 0.0458 1.0000 Uani . . . . . .
C11 C 0.7256(2) -0.1949(2) 0.45252(9) 0.0230 1.0000 Uani . . . . . .
C12 C 0.7667(2) -0.2204(2) 0.40424(9) 0.0238 1.0000 Uani . . . . . .
C13 C 0.8892(3) -0.3276(3) 0.34635(11) 0.0434 1.0000 Uani . . . . . .
C14 C 0.6329(2) -0.1293(2) 0.44913(9) 0.0236 1.0000 Uani . . . . . .
C15 C 0.6169(2) -0.0645(2) 0.41151(9) 0.0273 1.0000 Uani . . . . . .
C16 C 0.5299(2) -0.0079(2) 0.40938(10) 0.0280 1.0000 Uani . . . . . .
C17 C 0.4585(2) -0.0133(2) 0.44511(11) 0.0281 1.0000 Uani . . . . . .
C18 C 0.4747(2) -0.0758(2) 0.48218(9) 0.0283 1.0000 Uani . . . . . .
C19 C 0.5607(2) -0.1347(2) 0.48387(9) 0.0272 1.0000 Uani . . . . . .
C20 C 0.5769(2) 0.0638(3) 0.33618(11) 0.0361 1.0000 Uani . . . . . .
C21 C 0.5367(4) 0.1404(5) 0.30355(19) 0.0838 1.0000 Uani . . . . . .
C22 C 0.2992(2) 0.0407(3) 0.47502(11) 0.0363 1.0000 Uani . . . . . .
H21 H 1.0953 -0.0836 0.6130 0.0403 1.0000 Uiso R . . . . .
H662 H 1.1275 0.0413 0.5614 0.0440 1.0000 Uiso R . . . . .
H41 H 1.0294 0.0582 0.4945 0.0404 1.0000 Uiso R . . . . .
H101 H 0.9748 -0.3436 0.7061 0.0690 1.0000 Uiso R . . . . .
H102 H 0.8732 -0.2952 0.6924 0.0698 1.0000 Uiso R . . . . .
H103 H 0.9207 -0.3796 0.6628 0.0693 1.0000 Uiso R . . . . .
H111 H 0.7053 -0.2553 0.4668 0.0266 1.0000 Uiso R . . . . .
H121 H 0.7135 -0.2436 0.3854 0.0288 1.0000 Uiso R . . . . .
H122 H 0.7933 -0.1634 0.3893 0.0289 1.0000 Uiso R . . . . .
H131 H 0.9391 -0.3795 0.3442 0.0650 1.0000 Uiso R . . . . .
H132 H 0.8280 -0.3470 0.3317 0.0649 1.0000 Uiso R . . . . .
H133 H 0.9149 -0.2642 0.3342 0.0638 1.0000 Uiso R . . . . .
H151 H 0.6636 -0.0598 0.3888 0.0330 1.0000 Uiso R . . . . .
H181 H 0.4277 -0.0783 0.5047 0.0344 1.0000 Uiso R . . . . .
H191 H 0.5703 -0.1786 0.5085 0.0327 1.0000 Uiso R . . . . .
H201 H 0.6430 0.0820 0.3467 0.0421 1.0000 Uiso R . . . . .
H202 H 0.5797 -0.0019 0.3219 0.0435 1.0000 Uiso R . . . . .
H211 H 0.5269 0.2003 0.3208 0.1252 1.0000 Uiso R . . . . .
H212 H 0.5839 0.1514 0.2789 0.1251 1.0000 Uiso R . . . . .
H213 H 0.4733 0.1176 0.2918 0.1253 1.0000 Uiso R . . . . .
H221 H 0.3295 0.0577 0.5030 0.0534 1.0000 Uiso R . . . . .
H222 H 0.2464 0.0863 0.4679 0.0531 1.0000 Uiso R . . . . .
H223 H 0.2734 -0.0253 0.4761 0.0534 1.0000 Uiso R . . . . .
S31 S 0.09552(5) 0.94246(5) 0.33989(2) 0.0290 1.0000 Uani . . . . . .
O31 O -0.21168(15) 0.94752(17) 0.32686(7) 0.0314 1.0000 Uani . . . . . .
O32 O 0.01512(15) 1.00289(16) 0.20986(7) 0.0289 1.0000 Uani . . . . . .
O33 O -0.0830(2) 0.72915(18) 0.08843(7) 0.0406 1.0000 Uani . . . . . .
O34 O 0.04997(19) 0.85651(17) 0.31846(8) 0.0379 1.0000 Uani . . . . . .
O35 O 0.18159(19) 0.9855(2) 0.31680(9) 0.0477 1.0000 Uani . . . . . .
O36 O -0.29910(19) 1.40725(17) 0.32929(7) 0.0388 1.0000 Uani . . . . . .
O37 O -0.28777(17) 1.27407(17) 0.39419(7) 0.0346 1.0000 Uani . . . . . .
N33 N -0.09017(16) 0.99805(17) 0.27439(7) 0.0233 1.0000 Uani . . . . . .
N32 N -0.04720(18) 0.84610(18) 0.14327(8) 0.0270 1.0000 Uani D . . . . .
C31 C -0.1153(2) 0.8215(2) 0.17822(9) 0.0249 1.0000 Uani D . . . . .
C32 C -0.1841(2) 0.7419(2) 0.17688(10) 0.0311 1.0000 Uani . . . . . .
C33 C -0.2510(2) 0.7248(2) 0.21266(11) 0.0339 1.0000 Uani . . . . . .
C34 C -0.2553(2) 0.7858(2) 0.25187(10) 0.0305 1.0000 Uani . . . . . .
C35 C -0.1871(2) 0.8627(2) 0.25334(9) 0.0250 1.0000 Uani . . . . . .
C36 C -0.1684(2) 0.9383(2) 0.28957(9) 0.0257 1.0000 Uani . . . . . .
C37 C -0.0547(2) 0.9661(2) 0.23091(9) 0.0226 1.0000 Uani . . . . . .
C38 C -0.11800(19) 0.8804(2) 0.21787(9) 0.0225 1.0000 Uani . . . . . .
C39 C -0.0360(2) 0.8025(2) 0.10021(10) 0.0301 1.0000 Uani D . . . . .
C40 C 0.0377(3) 0.8545(3) 0.06916(11) 0.0392 1.0000 Uani . . . . . .
C41 C -0.0395(2) 1.0760(2) 0.30200(9) 0.0238 1.0000 Uani . . . . . .
C42 C 0.0009(2) 1.0339(2) 0.34783(9) 0.0253 1.0000 Uani . . . . . .
C43 C 0.1275(3) 0.9121(3) 0.39750(12) 0.0447 1.0000 Uani . . . . . .
C44 C -0.1084(2) 1.1645(2) 0.30999(9) 0.0238 1.0000 Uani . . . . . .
C45 C -0.1659(2) 1.1759(2) 0.35052(9) 0.0258 1.0000 Uani . . . . . .
C46 C -0.2289(2) 1.2574(2) 0.35629(9) 0.0269 1.0000 Uani . . . . . .
C47 C -0.2355(2) 1.3299(2) 0.32085(10) 0.0278 1.0000 Uani . . . . . .
C48 C -0.1777(2) 1.3186(2) 0.28113(9) 0.0285 1.0000 Uani . . . . . .
C49 C -0.1140(2) 1.2370(2) 0.27607(9) 0.0285 1.0000 Uani . . . . . .
C50 C -0.2859(2) 1.2007(2) 0.43046(10) 0.0320 1.0000 Uani . . . . . .
C51 C -0.3669(3) 1.2294(3) 0.46500(11) 0.0436 1.0000 Uani . . . . . .
C52 C -0.3090(3) 1.4783(3) 0.29298(12) 0.0479 1.0000 Uani . . . . . .
H321 H -0.1830 0.6987 0.1519 0.0383 1.0000 Uiso R . . . . .
H331 H -0.2911 0.6706 0.2105 0.0412 1.0000 Uiso R . . . . .
H341 H -0.2998 0.7736 0.2754 0.0365 1.0000 Uiso R . . . . .
H401 H 0.0970 0.8699 0.0859 0.0599 1.0000 Uiso R . . . . .
H402 H 0.0062 0.9144 0.0578 0.0594 1.0000 Uiso R . . . . .
H403 H 0.0542 0.8138 0.0428 0.0594 1.0000 Uiso R . . . . .
H411 H 0.0194 1.0977 0.2848 0.0295 1.0000 Uiso R . . . . .
H421 H -0.0532 1.0050 0.3663 0.0307 1.0000 Uiso R . . . . .
H422 H 0.0319 1.0888 0.3648 0.0302 1.0000 Uiso R . . . . .
H431 H 0.0705 0.8841 0.4131 0.0670 1.0000 Uiso R . . . . .
H432 H 0.1487 0.9713 0.4122 0.0664 1.0000 Uiso R . . . . .
H433 H 0.1822 0.8654 0.3960 0.0668 1.0000 Uiso R . . . . .
H451 H -0.1612 1.1284 0.3735 0.0315 1.0000 Uiso R . . . . .
H481 H -0.1815 1.3642 0.2578 0.0338 1.0000 Uiso R . . . . .
H491 H -0.0750 1.2319 0.2498 0.0344 1.0000 Uiso R . . . . .
H501 H -0.2209 1.1976 0.4440 0.0383 1.0000 Uiso R . . . . .
H502 H -0.3024 1.1365 0.4188 0.0382 1.0000 Uiso R . . . . .
H511 H -0.3510 1.2941 0.4775 0.0653 1.0000 Uiso R . . . . .
H512 H -0.3667 1.1842 0.4907 0.0658 1.0000 Uiso R . . . . .
H513 H -0.4319 1.2335 0.4508 0.0646 1.0000 Uiso R . . . . .
H521 H -0.2415 1.5041 0.2855 0.0704 1.0000 Uiso R . . . . .
H522 H -0.3511 1.5294 0.3039 0.0701 1.0000 Uiso R . . . . .
H523 H -0.3392 1.4475 0.2660 0.0705 1.0000 Uiso R . . . . .
H691 H 0.405(4) 0.177(2) 0.405(2) 0.079(2) 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2873(2)
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
H22 . N2 . 0.849(18) no
H320 . N32 . 0.842(18) no
O69 . C67 . 1.315(5) yes
O69 . H691 . 0.823(19) no
O68 . C67 . 1.214(5) yes
C61 . C62 . 1.396(5) yes
C61 . C66 . 1.376(5) yes
C61 . C67 . 1.499(4) yes
C62 . C63 . 1.386(5) yes
C62 . H621 . 0.948 no
C63 . C64 . 1.381(5) yes
C63 . H631 . 0.950 no
C64 . C65 . 1.366(5) yes
C64 . Br70 . 1.892(3) yes
C65 . C66 . 1.394(5) yes
C65 . H651 . 0.936 no
C66 . H661 . 0.982 no
S1 . O4 . 1.440(2) yes
S1 . O5 . 1.441(2) yes
S1 . C12 . 1.773(3) yes
S1 . C13 . 1.748(3) yes
O1 . C6 . 1.215(3) yes
O2 . C7 . 1.212(3) yes
O3 . C9 . 1.217(4) yes
O6 . C16 . 1.368(4) yes
O6 . C20 . 1.445(4) yes
O7 . C17 . 1.373(4) yes
O7 . C22 . 1.434(4) yes
N1 . C6 . 1.393(4) yes
N1 . C7 . 1.402(3) yes
N1 . C11 . 1.474(3) yes
N2 . C1 . 1.390(4) yes
N2 . C9 . 1.365(4) yes
C1 . C2 . 1.412(4) yes
C1 . C8 . 1.386(4) yes
C2 . C3 . 1.390(5) yes
C2 . H21 . 0.894 no
C3 . C4 . 1.398(5) yes
C3 . H662 . 0.931 no
C4 . C5 . 1.386(4) yes
C4 . H41 . 0.925 no
C5 . C6 . 1.495(4) yes
C5 . C8 . 1.381(4) yes
C7 . C8 . 1.481(4) yes
C9 . C10 . 1.508(5) yes
C10 . H101 . 0.944 no
C10 . H102 . 0.951 no
C10 . H103 . 0.946 no
C11 . C12 . 1.535(4) yes
C11 . C14 . 1.514(4) yes
C11 . H111 . 0.951 no
C12 . H121 . 0.942 no
C12 . H122 . 0.948 no
C13 . H131 . 0.963 no
C13 . H132 . 0.950 no
C13 . H133 . 0.985 no
C14 . C15 . 1.409(4) yes
C14 . C19 . 1.387(4) yes
C15 . C16 . 1.382(4) yes
C15 . H151 . 0.902 no
C16 . C17 . 1.400(4) yes
C17 . C18 . 1.379(4) yes
C18 . C19 . 1.389(4) yes
C18 . H181 . 0.899 no
C19 . H191 . 0.933 no
C20 . C21 . 1.495(5) yes
C20 . H201 . 0.957 no
C20 . H202 . 0.977 no
C21 . H211 . 0.957 no
C21 . H212 . 0.960 no
C21 . H213 . 0.955 no
C22 . H221 . 0.930 no
C22 . H222 . 0.952 no
C22 . H223 . 0.954 no
S31 . O34 . 1.444(2) yes
S31 . O35 . 1.441(3) yes
S31 . C42 . 1.771(3) yes
S31 . C43 . 1.765(3) yes
O31 . C36 . 1.225(3) yes
O32 . C37 . 1.212(3) yes
O33 . C39 . 1.216(4) yes
O36 . C47 . 1.361(4) yes
O36 . C52 . 1.426(4) yes
O37 . C46 . 1.362(3) yes
O37 . C50 . 1.440(3) yes
N33 . C36 . 1.382(4) yes
N33 . C37 . 1.408(3) yes
N33 . C41 . 1.478(3) yes
N32 . C31 . 1.393(3) yes
N32 . C39 . 1.383(4) yes
C31 . C32 . 1.407(4) yes
C31 . C38 . 1.394(4) yes
C32 . C33 . 1.380(4) yes
C32 . H321 . 0.926 no
C33 . C34 . 1.400(5) yes
C33 . H331 . 0.903 no
C34 . C35 . 1.375(4) yes
C34 . H341 . 0.914 no
C35 . C36 . 1.481(4) yes
C35 . C38 . 1.393(4) yes
C37 . C38 . 1.474(4) yes
C39 . C40 . 1.499(4) yes
C40 . H401 . 0.945 no
C40 . H402 . 0.965 no
C40 . H403 . 0.963 no
C41 . C42 . 1.536(4) yes
C41 . C44 . 1.518(4) yes
C41 . H411 . 0.968 no
C42 . H421 . 0.974 no
C42 . H422 . 0.977 no
C43 . H431 . 0.956 no
C43 . H432 . 0.947 no
C43 . H433 . 0.960 no
C44 . C45 . 1.404(4) yes
C44 . C49 . 1.385(4) yes
C45 . C46 . 1.388(4) yes
C45 . H451 . 0.923 no
C46 . C47 . 1.418(4) yes
C47 . C48 . 1.387(4) yes
C48 . C49 . 1.393(4) yes
C48 . H481 . 0.914 no
C49 . H491 . 0.919 no
C50 . C51 . 1.514(4) yes
C50 . H501 . 0.946 no
C50 . H502 . 0.953 no
C51 . H511 . 0.967 no
C51 . H512 . 0.959 no
C51 . H513 . 0.955 no
C52 . H521 . 0.982 no
C52 . H522 . 0.939 no
C52 . H523 . 0.968 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
C67 . O69 . H691 . 119(4) no
C62 . C61 . C66 . 120.5(3) yes
C62 . C61 . C67 . 120.5(3) yes
C66 . C61 . C67 . 118.9(3) yes
C61 . C62 . C63 . 119.4(3) yes
C61 . C62 . H621 . 121.0 no
C63 . C62 . H621 . 119.6 no
C62 . C63 . C64 . 118.9(3) yes
C62 . C63 . H631 . 120.8 no
C64 . C63 . H631 . 120.3 no
C63 . C64 . C65 . 122.5(3) yes
C63 . C64 . Br70 . 119.6(3) yes
C65 . C64 . Br70 . 117.9(3) yes
C64 . C65 . C66 . 118.6(3) yes
C64 . C65 . H651 . 119.4 no
C66 . C65 . H651 . 121.9 no
C65 . C66 . C61 . 120.1(3) yes
C65 . C66 . H661 . 118.7 no
C61 . C66 . H661 . 121.2 no
C61 . C67 . O69 . 112.2(3) yes
C61 . C67 . O68 . 123.3(4) yes
O69 . C67 . O68 . 124.5(3) yes
O4 . S1 . O5 . 117.58(14) yes
O4 . S1 . C12 . 109.31(13) yes
O5 . S1 . C12 . 108.67(14) yes
O4 . S1 . C13 . 108.46(16) yes
O5 . S1 . C13 . 109.52(18) yes
C12 . S1 . C13 . 102.19(15) yes
C16 . O6 . C20 . 117.6(2) yes
C17 . O7 . C22 . 116.8(2) yes
C6 . N1 . C7 . 111.6(2) yes
C6 . N1 . C11 . 125.9(2) yes
C7 . N1 . C11 . 122.2(2) yes
H22 . N2 . C1 . 116.0(13) no
H22 . N2 . C9 . 114.6(13) no
C1 . N2 . C9 . 129.4(3) yes
N2 . C1 . C2 . 125.3(3) yes
N2 . C1 . C8 . 118.5(3) yes
C2 . C1 . C8 . 116.1(3) yes
C1 . C2 . C3 . 121.0(3) yes
C1 . C2 . H21 . 118.6 no
C3 . C2 . H21 . 120.3 no
C2 . C3 . C4 . 122.3(3) yes
C2 . C3 . H662 . 118.7 no
C4 . C3 . H662 . 119.0 no
C3 . C4 . C5 . 115.9(3) yes
C3 . C4 . H41 . 121.8 no
C5 . C4 . H41 . 122.3 no
C4 . C5 . C6 . 129.6(3) yes
C4 . C5 . C8 . 122.4(3) yes
C6 . C5 . C8 . 108.0(2) yes
C5 . C6 . N1 . 105.9(2) yes
C5 . C6 . O1 . 129.0(3) yes
N1 . C6 . O1 . 125.1(3) yes
N1 . C7 . O2 . 125.3(2) yes
N1 . C7 . C8 . 106.0(2) yes
O2 . C7 . C8 . 128.7(2) yes
C7 . C8 . C1 . 129.2(3) yes
C7 . C8 . C5 . 108.5(2) yes
C1 . C8 . C5 . 122.3(3) yes
N2 . C9 . O3 . 122.5(3) yes
N2 . C9 . C10 . 114.8(3) yes
O3 . C9 . C10 . 122.7(3) yes
C9 . C10 . H101 . 108.8 no
C9 . C10 . H102 . 109.3 no
H101 . C10 . H102 . 109.1 no
C9 . C10 . H103 . 112.1 no
H101 . C10 . H103 . 107.2 no
H102 . C10 . H103 . 110.3 no
N1 . C11 . C12 . 111.5(2) yes
N1 . C11 . C14 . 112.2(2) yes
C12 . C11 . C14 . 111.0(2) yes
N1 . C11 . H111 . 106.9 no
C12 . C11 . H111 . 107.7 no
C14 . C11 . H111 . 107.3 no
C11 . C12 . S1 . 113.33(18) yes
C11 . C12 . H121 . 109.4 no
S1 . C12 . H121 . 108.9 no
C11 . C12 . H122 . 111.2 no
S1 . C12 . H122 . 107.2 no
H121 . C12 . H122 . 106.5 no
S1 . C13 . H131 . 106.7 no
S1 . C13 . H132 . 107.8 no
H131 . C13 . H132 . 110.8 no
S1 . C13 . H133 . 107.5 no
H131 . C13 . H133 . 111.7 no
H132 . C13 . H133 . 112.0 no
C11 . C14 . C15 . 122.2(2) yes
C11 . C14 . C19 . 118.7(2) yes
C15 . C14 . C19 . 119.1(3) yes
C14 . C15 . C16 . 120.1(2) yes
C14 . C15 . H151 . 120.0 no
C16 . C15 . H151 . 119.9 no
C15 . C16 . O6 . 124.7(3) yes
C15 . C16 . C17 . 120.0(3) yes
O6 . C16 . C17 . 115.2(2) yes
C16 . C17 . O7 . 115.3(3) yes
C16 . C17 . C18 . 120.0(3) yes
O7 . C17 . C18 . 124.7(3) yes
C17 . C18 . C19 . 120.2(3) yes
C17 . C18 . H181 . 118.4 no
C19 . C18 . H181 . 121.4 no
C18 . C19 . C14 . 120.6(3) yes
C18 . C19 . H191 . 120.0 no
C14 . C19 . H191 . 119.4 no
O6 . C20 . C21 . 107.4(3) yes
O6 . C20 . H201 . 111.0 no
C21 . C20 . H201 . 110.3 no
O6 . C20 . H202 . 106.8 no
C21 . C20 . H202 . 111.9 no
H201 . C20 . H202 . 109.4 no
C20 . C21 . H211 . 107.6 no
C20 . C21 . H212 . 110.1 no
H211 . C21 . H212 . 110.1 no
C20 . C21 . H213 . 108.4 no
H211 . C21 . H213 . 109.6 no
H212 . C21 . H213 . 110.9 no
O7 . C22 . H221 . 107.5 no
O7 . C22 . H222 . 109.0 no
H221 . C22 . H222 . 110.2 no
O7 . C22 . H223 . 108.9 no
H221 . C22 . H223 . 110.8 no
H222 . C22 . H223 . 110.3 no
O34 . S31 . O35 . 116.98(16) yes
O34 . S31 . C42 . 108.56(13) yes
O35 . S31 . C42 . 109.79(15) yes
O34 . S31 . C43 . 108.52(17) yes
O35 . S31 . C43 . 109.90(18) yes
C42 . S31 . C43 . 102.03(15) yes
C47 . O36 . C52 . 116.0(2) yes
C46 . O37 . C50 . 117.5(2) yes
C36 . N33 . C37 . 110.7(2) yes
C36 . N33 . C41 . 125.5(2) yes
C37 . N33 . C41 . 123.2(2) yes
H320 . N32 . C31 . 116.5(12) no
H320 . N32 . C39 . 115.2(12) no
C31 . N32 . C39 . 128.3(3) yes
N32 . C31 . C32 . 125.4(3) yes
N32 . C31 . C38 . 118.4(3) yes
C32 . C31 . C38 . 116.1(2) yes
C31 . C32 . C33 . 121.4(3) yes
C31 . C32 . H321 . 119.4 no
C33 . C32 . H321 . 119.2 no
C32 . C33 . C34 . 122.2(3) yes
C32 . C33 . H331 . 117.4 no
C34 . C33 . H331 . 120.3 no
C33 . C34 . C35 . 116.1(3) yes
C33 . C34 . H341 . 121.5 no
C35 . C34 . H341 . 122.3 no
C34 . C35 . C36 . 130.5(3) yes
C34 . C35 . C38 . 122.5(3) yes
C36 . C35 . C38 . 107.0(2) yes
C35 . C36 . N33 . 107.5(2) yes
C35 . C36 . O31 . 127.8(3) yes
N33 . C36 . O31 . 124.7(3) yes
N33 . C37 . O32 . 125.1(3) yes
N33 . C37 . C38 . 106.2(2) yes
O32 . C37 . C38 . 128.7(2) yes
C37 . C38 . C31 . 129.9(2) yes
C37 . C38 . C35 . 108.6(2) yes
C31 . C38 . C35 . 121.5(3) yes
N32 . C39 . O33 . 122.8(3) yes
N32 . C39 . C40 . 114.1(3) yes
O33 . C39 . C40 . 123.1(3) yes
C39 . C40 . H401 . 109.7 no
C39 . C40 . H402 . 108.3 no
H401 . C40 . H402 . 110.5 no
C39 . C40 . H403 . 110.7 no
H401 . C40 . H403 . 109.8 no
H402 . C40 . H403 . 107.8 no
N33 . C41 . C42 . 111.2(2) yes
N33 . C41 . C44 . 111.6(2) yes
C42 . C41 . C44 . 111.6(2) yes
N33 . C41 . H411 . 107.7 no
C42 . C41 . H411 . 105.8 no
C44 . C41 . H411 . 108.8 no
C41 . C42 . S31 . 113.01(18) yes
C41 . C42 . H421 . 111.3 no
S31 . C42 . H421 . 108.2 no
C41 . C42 . H422 . 107.4 no
S31 . C42 . H422 . 107.2 no
H421 . C42 . H422 . 109.7 no
S31 . C43 . H431 . 110.3 no
S31 . C43 . H432 . 107.3 no
H431 . C43 . H432 . 110.9 no
S31 . C43 . H433 . 106.8 no
H431 . C43 . H433 . 111.1 no
H432 . C43 . H433 . 110.4 no
C41 . C44 . C45 . 122.5(2) yes
C41 . C44 . C49 . 118.6(2) yes
C45 . C44 . C49 . 118.9(3) yes
C44 . C45 . C46 . 120.7(2) yes
C44 . C45 . H451 . 119.2 no
C46 . C45 . H451 . 120.1 no
C45 . C46 . O37 . 124.8(3) yes
C45 . C46 . C47 . 119.7(2) yes
O37 . C46 . C47 . 115.5(3) yes
C46 . C47 . O36 . 115.9(2) yes
C46 . C47 . C48 . 119.1(3) yes
O36 . C47 . C48 . 125.0(3) yes
C47 . C48 . C49 . 120.5(3) yes
C47 . C48 . H481 . 120.4 no
C49 . C48 . H481 . 119.1 no
C48 . C49 . C44 . 121.0(3) yes
C48 . C49 . H491 . 119.0 no
C44 . C49 . H491 . 120.1 no
O37 . C50 . C51 . 107.0(3) yes
O37 . C50 . H501 . 110.3 no
C51 . C50 . H501 . 112.4 no
O37 . C50 . H502 . 111.2 no
C51 . C50 . H502 . 107.7 no
H501 . C50 . H502 . 108.3 no
C50 . C51 . H511 . 108.9 no
C50 . C51 . H512 . 110.2 no
H511 . C51 . H512 . 106.4 no
C50 . C51 . H513 . 111.6 no
H511 . C51 . H513 . 107.8 no
H512 . C51 . H513 . 111.8 no
O36 . C52 . H521 . 108.4 no
O36 . C52 . H522 . 107.4 no
H521 . C52 . H522 . 110.7 no
O36 . C52 . H523 . 110.0 no
H521 . C52 . H523 . 110.4 no
H522 . C52 . H523 . 109.9 no



_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SQRTW        is   0.00
  Minimum value of RATIO        is  -3.00
;

# 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
2 1 0 x .
-6 7 2 x .
5 4 4 x .
0 1 5 x .
-6 12 2 x .
-1 5 25 x .
_chemical_name_systematic        
'bis(N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide) 4-bromobenzoic acid'
_chemical_name_common            'bis(apremilast) 4-bromobenzoic acid'
_chemical_melting_point          -
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methyl Ethyl Ketone'
