#------------------------------------------------------------------------------
#$Date: 2021-03-04 04:38:18 +0200 (Thu, 04 Mar 2021) $
#$Revision: 262435 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/08/1560811.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1560811
loop_
_publ_author_name
'Gui, Yue'
'McCann, Erin C.'
'Yao, Xin'
'Li, Yuhui'
'Jones, Karen J.'
'Yu, Lian'
_publ_section_title
;
 Amorphous Drug-Polymer Salt with High Stability under Tropical Conditions
 and Fast Dissolution: The Case of Clofazimine and Poly(acrylic acid).
;
_journal_issue                   3
_journal_name_full               'Molecular pharmaceutics'
_journal_page_first              1364
_journal_page_last               1372
_journal_paper_doi               10.1021/acs.molpharmaceut.0c01180
_journal_volume                  18
_journal_year                    2021
_chemical_formula_moiety         'C27 H23 Cl2 N4, C12 H25 O4 S'
_chemical_formula_sum            'C39 H48 Cl2 N4 O4 S'
_chemical_formula_weight         739.77
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                116.386(10)
_cell_angle_beta                 91.271(8)
_cell_angle_gamma                108.043(6)
_cell_formula_units_Z            2
_cell_length_a                   10.9239(13)
_cell_length_b                   13.7852(15)
_cell_length_c                   14.6224(16)
_cell_measurement_reflns_used    5661
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      78.913
_cell_measurement_theta_min      3.435
_cell_volume                     1842.2(4)
_computing_cell_refinement       'APEX3 (Bruker AXS Inc., 2019)'
_computing_data_collection
;
Bruker Instrument Service, BIS, v.6.2.12 (Bruker AXS Inc., 2019)'
;
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2019)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT, VERSION 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '0.5\ ω and 0.5\ φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON III'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19377
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         79.363
_diffrn_reflns_theta_min         3.435
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.486
_exptl_absorpt_correction_T_max  0.7746
_exptl_absorpt_correction_T_min  0.6260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         7647
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0569P)²+0.2315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5420
_reflns_number_total             7647
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mp0c01180_si_002.cif
_cod_data_source_block           yu216
_cod_database_code               1560811
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.722
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uiso(C37A) = Uiso(C38A) = Uiso(C39A)
3. Same fragment restrains
{C35, C36, C37A, C38A, C39A} sigma for 1-2: 0.008, 1-3: 0.016
as in
{C35, C36, C37, C38, C39}
4. Others
 Sof(H36C)=Sof(H36D)=Sof(C37A)=Sof(H37C)=Sof(H37D)=Sof(C38A)=Sof(H38C)=
 Sof(H38D)=Sof(C39A)=Sof(H39D)=Sof(H39E)=Sof(H39F)=1-FVAR(1)
 Sof(H36A)=Sof(H36B)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(C38)=Sof(H38A)=Sof(H38B)=
 Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(H39C)=FVAR(1)
 Fixed Uiso: C37A(0.048) C38A(0.048) C39A(0.048)
5.a Ternary CH refined with riding coordinates:
 C25(H25)
5.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,
 H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B),
 C36(H36C,H36D), C37(H37A,H37B), C38(H38A,H38B), C37A(H37C,H37D), C38A(H38C,
 H38D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23)
5.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C39(H39A,H39B,H39C), C39A(H39D,H39E,
 H39F)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.63996(7) 0.34439(5) 0.92083(5) 0.02834(16) Uani 1 1 d . . . . .
Cl2 Cl 0.16141(7) 1.12427(5) 0.59499(5) 0.03033(16) Uani 1 1 d . . . . .
N1 N 0.5405(2) 0.62537(17) 0.73695(17) 0.0221(4) Uani 1 1 d . . . . .
H1 H 0.585(3) 0.621(3) 0.684(3) 0.026 Uiso 1 1 d . U . . .
N2 N 0.3799(2) 0.88016(16) 1.00843(16) 0.0207(4) Uani 1 1 d . . . . .
N3 N 0.2890(2) 0.94701(16) 0.87351(16) 0.0199(4) Uani 1 1 d . . . . .
N4 N 0.4679(2) 0.70459(18) 0.60854(17) 0.0229(4) Uani 1 1 d . . . . .
H4 H 0.510(3) 0.657(3) 0.589(3) 0.027 Uiso 1 1 d . U . . .
C1 C 0.5626(3) 0.56255(19) 0.78596(19) 0.0211(5) Uani 1 1 d . . . . .
C2 C 0.6803(3) 0.5423(2) 0.7816(2) 0.0231(5) Uani 1 1 d . . . . .
H2 H 0.745286 0.575832 0.751459 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7029(3) 0.4731(2) 0.8212(2) 0.0229(5) Uani 1 1 d . . . . .
H3 H 0.782317 0.457999 0.817165 0.028 Uiso 1 1 calc R U . . .
C4 C 0.6082(3) 0.42645(19) 0.8668(2) 0.0227(5) Uani 1 1 d . . . . .
C5 C 0.4897(3) 0.4447(2) 0.8709(2) 0.0231(5) Uani 1 1 d . . . . .
H5 H 0.425354 0.411256 0.901396 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4663(3) 0.5123(2) 0.8299(2) 0.0231(5) Uani 1 1 d . . . . .
H6 H 0.385260 0.524551 0.831643 0.028 Uiso 1 1 calc R U . . .
C7 C 0.4828(3) 0.70779(19) 0.77540(19) 0.0199(5) Uani 1 1 d . . . . .
C8 C 0.4602(3) 0.75438(19) 0.87454(19) 0.0208(5) Uani 1 1 d . . . . .
H8 H 0.488287 0.731110 0.920935 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3961(2) 0.83659(19) 0.91120(19) 0.0203(5) Uani 1 1 d . . . . .
C10 C 0.3143(3) 0.95641(18) 1.04061(19) 0.0206(5) Uani 1 1 d . . . . .
C11 C 0.2945(3) 1.00279(19) 1.1441(2) 0.0229(5) Uani 1 1 d . . . . .
H11 H 0.329226 0.982734 1.190551 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2255(3) 1.0770(2) 1.1789(2) 0.0252(5) Uani 1 1 d . . . . .
H12 H 0.212240 1.107118 1.248698 0.030 Uiso 1 1 calc R U . . .
C13 C 0.1748(3) 1.1079(2) 1.1106(2) 0.0255(5) Uani 1 1 d . . . . .
H13 H 0.126453 1.158228 1.134606 0.031 Uiso 1 1 calc R U . . .
C14 C 0.1944(3) 1.0659(2) 1.0091(2) 0.0244(5) Uani 1 1 d . . . . .
H14 H 0.160642 1.087913 0.963858 0.029 Uiso 1 1 calc R U . . .
C15 C 0.2648(3) 0.99052(19) 0.97343(19) 0.0209(5) Uani 1 1 d . . . . .
C16 C 0.2538(3) 0.98928(19) 0.80515(19) 0.0198(5) Uani 1 1 d . . . . .
C17 C 0.1337(3) 0.9314(2) 0.7385(2) 0.0235(5) Uani 1 1 d . . . . .
H17 H 0.072032 0.864980 0.737880 0.028 Uiso 1 1 calc R U . . .
C18 C 0.1049(3) 0.9724(2) 0.6722(2) 0.0247(5) Uani 1 1 d . . . . .
H18 H 0.023122 0.934285 0.625598 0.030 Uiso 1 1 calc R U . . .
C19 C 0.1980(3) 1.0703(2) 0.6753(2) 0.0244(5) Uani 1 1 d . . . . .
C20 C 0.3174(3) 1.1272(2) 0.7418(2) 0.0247(5) Uani 1 1 d . . . . .
H20 H 0.379043 1.193705 0.742551 0.030 Uiso 1 1 calc R U . . .
C21 C 0.3470(3) 1.0864(2) 0.8080(2) 0.0222(5) Uani 1 1 d . . . . .
H21 H 0.429121 1.124124 0.854155 0.027 Uiso 1 1 calc R U . . .
C22 C 0.3530(2) 0.87060(19) 0.83866(19) 0.0195(5) Uani 1 1 d . . . . .
C23 C 0.3791(3) 0.82701(19) 0.73892(19) 0.0207(5) Uani 1 1 d . . . . .
H23 H 0.353000 0.851970 0.693226 0.025 Uiso 1 1 calc R U . . .
C24 C 0.4434(2) 0.74640(19) 0.70367(19) 0.0192(5) Uani 1 1 d . . . . .
C25 C 0.4321(3) 0.7349(2) 0.5293(2) 0.0253(5) Uani 1 1 d . . . . .
H25 H 0.450210 0.820208 0.563765 0.030 Uiso 1 1 calc R U . . .
C26 C 0.2868(3) 0.6712(2) 0.4815(2) 0.0286(6) Uani 1 1 d . . . . .
H26A H 0.265380 0.690819 0.427977 0.043 Uiso 1 1 calc R U . . .
H26B H 0.234764 0.694351 0.535708 0.043 Uiso 1 1 calc R U . . .
H26C H 0.266796 0.587408 0.450125 0.043 Uiso 1 1 calc R U . . .
C27 C 0.5205(3) 0.7074(2) 0.4500(2) 0.0280(6) Uani 1 1 d . . . . .
H27A H 0.508255 0.624911 0.419024 0.042 Uiso 1 1 calc R U . . .
H27B H 0.612147 0.754145 0.484330 0.042 Uiso 1 1 calc R U . . .
H27C H 0.498079 0.725225 0.395435 0.042 Uiso 1 1 calc R U . . .
S1 S 0.80486(6) 0.66579(5) 0.58332(5) 0.02141(15) Uani 1 1 d . . . . .
O1 O 0.66635(19) 0.59429(15) 0.56241(14) 0.0251(4) Uani 1 1 d . . . . .
O2 O 0.8735(2) 0.69344(15) 0.68176(14) 0.0263(4) Uani 1 1 d . . . . .
O3 O 0.8245(2) 0.76323(15) 0.56450(15) 0.0279(4) Uani 1 1 d . . . . .
O4 O 0.87111(19) 0.58358(15) 0.50280(14) 0.0246(4) Uani 1 1 d . . . . .
C28 C 0.8377(3) 0.5536(2) 0.3954(2) 0.0263(5) Uani 1 1 d . . . . .
H28A H 0.872614 0.623245 0.385961 0.032 Uiso 1 1 calc R U . . .
H28B H 0.741373 0.520328 0.372336 0.032 Uiso 1 1 calc R U . . .
C29 C 0.8986(3) 0.4651(2) 0.3330(2) 0.0256(5) Uani 1 1 d . . . . .
H29A H 0.852162 0.391305 0.333461 0.031 Uiso 1 1 calc R U . . .
H29B H 0.991398 0.493249 0.365946 0.031 Uiso 1 1 calc R U . . .
C30 C 0.8913(3) 0.4436(2) 0.2211(2) 0.0249(5) Uani 1 1 d . . . . .
H30A H 0.940880 0.516970 0.220859 0.030 Uiso 1 1 calc R U . . .
H30B H 0.798735 0.419299 0.189521 0.030 Uiso 1 1 calc R U . . .
C31 C 0.9462(3) 0.3510(2) 0.15477(19) 0.0223(5) Uani 1 1 d . . . . .
H31A H 0.885888 0.274548 0.143159 0.027 Uiso 1 1 calc R U . . .
H31B H 1.031597 0.366830 0.193618 0.027 Uiso 1 1 calc R U . . .
C32 C 0.9655(3) 0.3450(2) 0.0495(2) 0.0242(5) Uani 1 1 d . . . . .
H32A H 1.020115 0.422888 0.060382 0.029 Uiso 1 1 calc R U . . .
H32B H 0.879195 0.322275 0.007767 0.029 Uiso 1 1 calc R U . . .
C33 C 1.0311(3) 0.2584(2) -0.0110(2) 0.0264(6) Uani 1 1 d . . . . .
H33A H 1.092667 0.257719 0.039235 0.032 Uiso 1 1 calc R U . . .
H33B H 0.962928 0.179999 -0.048138 0.032 Uiso 1 1 calc R U . . .
C34 C 1.1057(3) 0.2832(2) -0.0895(2) 0.0321(6) Uani 1 1 d . . . . .
H34A H 1.140428 0.220459 -0.126452 0.038 Uiso 1 1 calc R U . . .
H34B H 1.181847 0.356322 -0.050964 0.038 Uiso 1 1 calc R U . . .
C35 C 1.0276(3) 0.2937(2) -0.1704(2) 0.0308(6) Uani 1 1 d D . . . .
H35A H 0.999184 0.360631 -0.134080 0.037 Uiso 1 1 calc R U . . .
H35B H 1.086233 0.310257 -0.216380 0.037 Uiso 1 1 calc R U . . .
C36 C 0.9075(3) 0.1868(2) -0.2373(2) 0.0324(6) Uani 1 1 d D . . . .
H36A H 0.838469 0.180627 -0.195295 0.039 Uiso 0.858(7) 1 calc R U P A 1
H36B H 0.930886 0.116592 -0.261315 0.039 Uiso 0.858(7) 1 calc R U P A 1
H36C H 0.939433 0.121599 -0.270885 0.039 Uiso 0.142(7) 1 calc R U P A 2
H36D H 0.853334 0.170999 -0.188628 0.039 Uiso 0.142(7) 1 calc R U P A 2
C37 C 0.8548(4) 0.1936(4) -0.3319(3) 0.0337(8) Uani 0.858(7) 1 d D . P A 1
H37A H 0.922645 0.194761 -0.375542 0.040 Uiso 0.858(7) 1 calc R U P A 1
H37B H 0.839227 0.267560 -0.307068 0.040 Uiso 0.858(7) 1 calc R U P A 1
C38 C 0.7270(4) 0.0930(3) -0.3996(3) 0.0385(10) Uani 0.858(7) 1 d D . P A 1
H38A H 0.713142 0.091636 -0.467386 0.046 Uiso 0.858(7) 1 calc R U P A 1
H38B H 0.736820 0.018992 -0.413160 0.046 Uiso 0.858(7) 1 calc R U P A 1
C39 C 0.6056(4) 0.1007(3) -0.3505(3) 0.0384(9) Uani 0.858(7) 1 d D . P A 1
H39A H 0.528270 0.034017 -0.397222 0.058 Uiso 0.858(7) 1 calc R U P A 1
H39B H 0.593178 0.172472 -0.339025 0.058 Uiso 0.858(7) 1 calc R U P A 1
H39C H 0.617616 0.100723 -0.283923 0.058 Uiso 0.858(7) 1 calc R U P A 1
C37A C 0.815(2) 0.1774(19) -0.321(2) 0.048 Uiso 0.142(7) 1 d D U P A 2
H37C H 0.862321 0.180879 -0.377504 0.058 Uiso 0.142(7) 1 calc R U P A 2
H37D H 0.784953 0.244080 -0.292342 0.058 Uiso 0.142(7) 1 calc R U P A 2
C38A C 0.694(2) 0.0628(18) -0.3681(18) 0.048 Uiso 0.142(7) 1 d D U P A 2
H38C H 0.724311 -0.002827 -0.385790 0.058 Uiso 0.142(7) 1 calc R U P A 2
H38D H 0.638945 0.065535 -0.314627 0.058 Uiso 0.142(7) 1 calc R U P A 2
C39A C 0.610(2) 0.041(2) -0.4650(16) 0.048 Uiso 0.142(7) 1 d D U P A 2
H39D H 0.666109 0.052565 -0.513114 0.072 Uiso 0.142(7) 1 calc R U P A 2
H39E H 0.561946 0.094391 -0.445197 0.072 Uiso 0.142(7) 1 calc R U P A 2
H39F H 0.547054 -0.039282 -0.499006 0.072 Uiso 0.142(7) 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 115(2) . . ?
C7 N1 H1 118(2) . . ?
C7 N1 C1 125.4(2) . . ?
C9 N2 C10 118.2(2) . . ?
C15 N3 C16 119.7(2) . . ?
C22 N3 C15 121.6(2) . . ?
C22 N3 C16 118.6(2) . . ?
C24 N4 H4 120(2) . . ?
C24 N4 C25 125.0(2) . . ?
C25 N4 H4 115(2) . . ?
C2 C1 N1 117.7(2) . . ?
C2 C1 C6 119.9(2) . . ?
C6 C1 N1 122.2(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 Cl1 119.0(2) . . ?
C3 C4 C5 121.3(2) . . ?
C5 C4 Cl1 119.7(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
N1 C7 C24 117.2(2) . . ?
C8 C7 N1 123.7(2) . . ?
C8 C7 C24 119.1(2) . . ?
C7 C8 H8 118.7 . . ?
C7 C8 C9 122.6(2) . . ?
C9 C8 H8 118.7 . . ?
N2 C9 C8 119.5(2) . . ?
N2 C9 C22 122.6(2) . . ?
C8 C9 C22 117.9(2) . . ?
N2 C10 C11 119.0(2) . . ?
N2 C10 C15 122.6(2) . . ?
C11 C10 C15 118.4(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.5(2) . . ?
C15 C14 H14 120.3 . . ?
N3 C15 C10 117.4(2) . . ?
N3 C15 C14 122.2(2) . . ?
C14 C15 C10 120.5(2) . . ?
C17 C16 N3 120.3(2) . . ?
C17 C16 C21 122.4(2) . . ?
C21 C16 N3 117.2(2) . . ?
C16 C17 H17 120.7 . . ?
C16 C17 C18 118.7(2) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.0(2) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 Cl2 119.4(2) . . ?
C20 C19 Cl2 118.7(2) . . ?
C20 C19 C18 121.9(2) . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.4(2) . . ?
C21 C20 H20 120.3 . . ?
C16 C21 C20 118.6(2) . . ?
C16 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
N3 C22 C9 117.5(2) . . ?
N3 C22 C23 122.3(2) . . ?
C23 C22 C9 120.2(2) . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.4(2) . . ?
C24 C23 H23 119.3 . . ?
N4 C24 C7 119.8(2) . . ?
N4 C24 C23 121.4(2) . . ?
C23 C24 C7 118.7(2) . . ?
N4 C25 H25 108.5 . . ?
N4 C25 C26 110.6(2) . . ?
N4 C25 C27 107.4(2) . . ?
C26 C25 H25 108.5 . . ?
C27 C25 H25 108.5 . . ?
C27 C25 C26 113.1(2) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O1 S1 O4 105.69(10) . . ?
O2 S1 O1 112.56(12) . . ?
O2 S1 O3 114.99(11) . . ?
O2 S1 O4 102.18(11) . . ?
O3 S1 O1 112.71(12) . . ?
O3 S1 O4 107.56(11) . . ?
C28 O4 S1 116.50(17) . . ?
O4 C28 H28A 110.3 . . ?
O4 C28 H28B 110.3 . . ?
O4 C28 C29 107.0(2) . . ?
H28A C28 H28B 108.6 . . ?
C29 C28 H28A 110.3 . . ?
C29 C28 H28B 110.3 . . ?
C28 C29 H29A 109.3 . . ?
C28 C29 H29B 109.3 . . ?
C28 C29 C30 111.6(2) . . ?
H29A C29 H29B 108.0 . . ?
C30 C29 H29A 109.3 . . ?
C30 C29 H29B 109.3 . . ?
C29 C30 H30A 109.0 . . ?
C29 C30 H30B 109.0 . . ?
C29 C30 C31 113.0(2) . . ?
H30A C30 H30B 107.8 . . ?
C31 C30 H30A 109.0 . . ?
C31 C30 H30B 109.0 . . ?
C30 C31 H31A 108.8 . . ?
C30 C31 H31B 108.8 . . ?
C30 C31 C32 113.7(2) . . ?
H31A C31 H31B 107.7 . . ?
C32 C31 H31A 108.8 . . ?
C32 C31 H31B 108.8 . . ?
C31 C32 H32A 109.2 . . ?
C31 C32 H32B 109.2 . . ?
C31 C32 C33 112.3(2) . . ?
H32A C32 H32B 107.9 . . ?
C33 C32 H32A 109.2 . . ?
C33 C32 H32B 109.2 . . ?
C32 C33 H33A 108.6 . . ?
C32 C33 H33B 108.6 . . ?
H33A C33 H33B 107.5 . . ?
C34 C33 C32 114.8(2) . . ?
C34 C33 H33A 108.6 . . ?
C34 C33 H33B 108.6 . . ?
C33 C34 H34A 108.3 . . ?
C33 C34 H34B 108.3 . . ?
C33 C34 C35 116.0(3) . . ?
H34A C34 H34B 107.4 . . ?
C35 C34 H34A 108.3 . . ?
C35 C34 H34B 108.3 . . ?
C34 C35 H35A 108.6 . . ?
C34 C35 H35B 108.6 . . ?
H35A C35 H35B 107.6 . . ?
C36 C35 C34 114.7(2) . . ?
C36 C35 H35A 108.6 . . ?
C36 C35 H35B 108.6 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 106.3 . . ?
C35 C36 H36D 106.3 . . ?
C35 C36 C37 110.7(3) . . ?
H36A C36 H36B 108.1 . . ?
H36C C36 H36D 106.4 . . ?
C37 C36 H36A 109.5 . . ?
C37 C36 H36B 109.5 . . ?
C37A C36 C35 124.2(7) . . ?
C37A C36 H36C 106.3 . . ?
C37A C36 H36D 106.3 . . ?
C36 C37 H37A 108.7 . . ?
C36 C37 H37B 108.7 . . ?
C36 C37 C38 114.2(3) . . ?
H37A C37 H37B 107.6 . . ?
C38 C37 H37A 108.7 . . ?
C38 C37 H37B 108.7 . . ?
C37 C38 H38A 108.8 . . ?
C37 C38 H38B 108.8 . . ?
H38A C38 H38B 107.7 . . ?
C39 C38 C37 113.8(3) . . ?
C39 C38 H38A 108.8 . . ?
C39 C38 H38B 108.8 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C36 C37A H37C 109.2 . . ?
C36 C37A H37D 109.2 . . ?
C36 C37A C38A 112.1(10) . . ?
H37C C37A H37D 107.9 . . ?
C38A C37A H37C 109.2 . . ?
C38A C37A H37D 109.2 . . ?
C37A C38A H38C 108.9 . . ?
C37A C38A H38D 108.9 . . ?
H38C C38A H38D 107.7 . . ?
C39A C38A C37A 113.6(11) . . ?
C39A C38A H38C 108.9 . . ?
C39A C38A H38D 108.9 . . ?
C38A C39A H39D 109.5 . . ?
C38A C39A H39E 109.5 . . ?
C38A C39A H39F 109.5 . . ?
H39D C39A H39E 109.5 . . ?
H39D C39A H39F 109.5 . . ?
H39E C39A H39F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.746(3) . ?
Cl2 C19 1.742(3) . ?
N1 H1 0.91(4) . ?
N1 C1 1.413(3) . ?
N1 C7 1.377(3) . ?
N2 C9 1.316(3) . ?
N2 C10 1.371(3) . ?
N3 C15 1.379(3) . ?
N3 C16 1.458(3) . ?
N3 C22 1.361(3) . ?
N4 H4 0.87(4) . ?
N4 C24 1.318(3) . ?
N4 C25 1.476(3) . ?
C1 C2 1.395(4) . ?
C1 C6 1.406(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(4) . ?
C4 C5 1.391(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.364(4) . ?
C7 C24 1.479(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.425(4) . ?
C9 C22 1.457(3) . ?
C10 C11 1.409(4) . ?
C10 C15 1.423(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.409(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.405(4) . ?
C16 C17 1.382(4) . ?
C16 C21 1.391(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.397(4) . ?
C19 C20 1.376(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.393(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.409(4) . ?
C25 H25 1.0000 . ?
C25 C26 1.524(4) . ?
C25 C27 1.519(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
S1 O1 1.464(2) . ?
S1 O2 1.4379(19) . ?
S1 O3 1.4418(19) . ?
S1 O4 1.598(2) . ?
O4 C28 1.440(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.517(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.523(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.526(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.528(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.530(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.521(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.527(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.521(4) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 H36C 0.9900 . ?
C36 H36D 0.9900 . ?
C36 C37 1.540(4) . ?
C36 C37A 1.508(8) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C38 1.540(6) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.532(6) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C37A H37C 0.9900 . ?
C37A H37D 0.9900 . ?
C37A C38A 1.555(10) . ?
C38A H38C 0.9900 . ?
C38A H38D 0.9900 . ?
C38A C39A 1.526(10) . ?
C39A H39D 0.9800 . ?
C39A H39E 0.9800 . ?
C39A H39F 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.91(4) 1.95(4) 2.852(3) 173(3) . yes
N4 H4 O1 0.87(4) 2.11(4) 2.943(3) 161(3) . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C4 C5 C6 178.51(19) . . . . ?
Cl2 C19 C20 C21 178.7(2) . . . . ?
N1 C1 C2 C3 -174.9(2) . . . . ?
N1 C1 C6 C5 175.6(2) . . . . ?
N1 C7 C8 C9 -177.7(2) . . . . ?
N1 C7 C24 N4 -2.1(3) . . . . ?
N1 C7 C24 C23 177.4(2) . . . . ?
N2 C9 C22 N3 -2.7(3) . . . . ?
N2 C9 C22 C23 176.3(2) . . . . ?
N2 C10 C11 C12 -177.9(2) . . . . ?
N2 C10 C15 N3 -2.3(3) . . . . ?
N2 C10 C15 C14 177.9(2) . . . . ?
N3 C16 C17 C18 -178.2(2) . . . . ?
N3 C16 C21 C20 178.5(2) . . . . ?
N3 C22 C23 C24 -178.9(2) . . . . ?
C1 N1 C7 C8 12.1(4) . . . . ?
C1 N1 C7 C24 -167.7(2) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C1 C6 C5 1.4(4) . . . . ?
C2 C3 C4 Cl1 -177.55(18) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C7 N1 C1 C2 -140.4(3) . . . . ?
C7 N1 C1 C6 45.3(3) . . . . ?
C7 C8 C9 N2 -178.5(2) . . . . ?
C7 C8 C9 C22 0.4(4) . . . . ?
C8 C7 C24 N4 178.1(2) . . . . ?
C8 C7 C24 C23 -2.4(3) . . . . ?
C8 C9 C22 N3 178.4(2) . . . . ?
C8 C9 C22 C23 -2.5(3) . . . . ?
C9 N2 C10 C11 179.2(2) . . . . ?
C9 N2 C10 C15 -0.6(3) . . . . ?
C9 C22 C23 C24 2.1(4) . . . . ?
C10 N2 C9 C8 -178.1(2) . . . . ?
C10 N2 C9 C22 3.1(3) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C11 C10 C15 N3 177.9(2) . . . . ?
C11 C10 C15 C14 -1.9(3) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C13 C14 C15 N3 -179.1(2) . . . . ?
C13 C14 C15 C10 0.7(4) . . . . ?
C15 N3 C16 C17 -93.5(3) . . . . ?
C15 N3 C16 C21 88.6(3) . . . . ?
C15 N3 C22 C9 -0.4(3) . . . . ?
C15 N3 C22 C23 -179.4(2) . . . . ?
C15 C10 C11 C12 1.8(4) . . . . ?
C16 N3 C15 C10 -173.0(2) . . . . ?
C16 N3 C15 C14 6.8(3) . . . . ?
C16 N3 C22 C9 175.4(2) . . . . ?
C16 N3 C22 C23 -3.7(3) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C17 C16 C21 C20 0.6(4) . . . . ?
C17 C18 C19 Cl2 -178.5(2) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C16 -0.5(4) . . . . ?
C21 C16 C17 C18 -0.4(4) . . . . ?
C22 N3 C15 C10 2.7(3) . . . . ?
C22 N3 C15 C14 -177.5(2) . . . . ?
C22 N3 C16 C17 90.7(3) . . . . ?
C22 N3 C16 C21 -87.2(3) . . . . ?
C22 C23 C24 N4 179.8(2) . . . . ?
C22 C23 C24 C7 0.3(4) . . . . ?
C24 N4 C25 C26 -77.6(3) . . . . ?
C24 N4 C25 C27 158.5(2) . . . . ?
C24 C7 C8 C9 2.0(4) . . . . ?
C25 N4 C24 C7 179.2(2) . . . . ?
C25 N4 C24 C23 -0.3(4) . . . . ?
S1 O4 C28 C29 -173.58(17) . . . . ?
O1 S1 O4 C28 71.1(2) . . . . ?
O2 S1 O4 C28 -171.00(18) . . . . ?
O3 S1 O4 C28 -49.6(2) . . . . ?
O4 C28 C29 C30 -169.5(2) . . . . ?
C28 C29 C30 C31 -177.5(2) . . . . ?
C29 C30 C31 C32 -168.4(2) . . . . ?
C30 C31 C32 C33 175.3(2) . . . . ?
C31 C32 C33 C34 -154.6(2) . . . . ?
C32 C33 C34 C35 -55.3(3) . . . . ?
C33 C34 C35 C36 -58.8(3) . . . . ?
C34 C35 C36 C37 -166.5(3) . . . . ?
C34 C35 C36 C37A 179.5(19) . . . . ?
C35 C36 C37 C38 -175.7(3) . . . . ?
C35 C36 C37A C38A -174.0(18) . . . . ?
C36 C37 C38 C39 73.9(4) . . . . ?
C36 C37A C38A C39A -170(3) . . . . ?
