#------------------------------------------------------------------------------
#$Date: 2021-02-05 00:57:25 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261597 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/15/7241514.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_7241514
loop_
_publ_author_name
'Bodart, Laurie'
'Prinzo, Maria'
'Derlet, Amélie'
'Tumanov, Nikolay'
'Wouters, Johan'
_publ_section_title
;
 Taking advantage of solvate formation to modulate drug--drug ratio in
 clofaziminium diclofenac salts
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              185
_journal_page_last               201
_journal_paper_doi               10.1039/D0CE01400A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety
;
2(C27 H23 Cl2 N4), 2(C14 H10 Cl2 N O2), 5(C9 H10 O)
;
_chemical_formula_sum            'C127 H116 Cl8 N10 O9'
_chemical_formula_weight         2209.89
_chemical_name_systematic
; 
pentakis(1-phenylpropan-1-one) bis(N-[(2E)-10-(4-chlorophenyl)
-3-[(4-chlorophenyl)amino]-2,10-dihydrophenazin-2-ylidene]
propan-2-aminium) bis(2-{2-[(2,6-dichlorophenyl)amino]phenyl}
acetate)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-09-17 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                73.502(4)
_cell_angle_beta                 77.404(4)
_cell_angle_gamma                73.540(4)
_cell_formula_units_Z            1
_cell_length_a                   10.7319(4)
_cell_length_b                   13.6005(6)
_cell_length_c                   21.5496(9)
_cell_measurement_reflns_used    6947
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      66.6340
_cell_measurement_theta_min      3.6160
_cell_volume                     2859.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28672
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         2.163
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.304
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'Metallic Dark Red'
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1156
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     937
_refine_ls_number_reflns         10049
_refine_ls_number_restraints     445
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0746P)²+0.3561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1602
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6767
_reflns_number_total             10049
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01400a2.cif
_cod_data_source_block           lb0623_CFZ-DCF_in_PPP
_cod_depositor_comments
'Adding full bibliography for 7241513--7241524.cif.'
_cod_database_code               7241514
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.656
_shelx_estimated_absorpt_t_max   0.855
_oxdiff_exptl_absorpt_empirical_full_min 0.798
_oxdiff_exptl_absorpt_empirical_full_max 1.447
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
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 0.95034(11) 0.89037(7) 0.32115(5) 0.1235(3) Uani 1 1 d . . . . .
Cl2 Cl 0.37325(10) -0.08427(7) 0.41732(5) 0.1141(3) Uani 1 1 d . . . . .
N1 N 0.72715(17) 0.52436(14) 0.46377(8) 0.0559(4) Uani 1 1 d . . . . .
N2 N 0.61523(18) 0.35329(15) 0.52753(9) 0.0601(4) Uani 1 1 d . . . . .
N3 N 0.5718(2) 0.30400(16) 0.32365(10) 0.0664(5) Uani 1 1 d . . . . .
H3 H 0.562(3) 0.337(2) 0.2824(15) 0.080 Uiso 1 1 d . U . . .
N4 N 0.6867(2) 0.47077(17) 0.25959(10) 0.0654(5) Uani 1 1 d . . . . .
H4 H 0.657(3) 0.439(2) 0.2386(14) 0.079 Uiso 1 1 d . U . . .
C1 C 0.7403(2) 0.5500(2) 0.56964(12) 0.0646(6) Uani 1 1 d . . . . .
H1 H 0.776940 0.607743 0.549815 0.077 Uiso 1 1 calc R U . . .
C2 C 0.7173(2) 0.5174(2) 0.63646(12) 0.0709(6) Uani 1 1 d . . . . .
H2 H 0.738308 0.553898 0.661725 0.085 Uiso 1 1 calc R U . . .
C3 C 0.6630(2) 0.4308(2) 0.66757(12) 0.0722(6) Uani 1 1 d . . . . .
H3A H 0.648412 0.409812 0.713021 0.087 Uiso 1 1 calc R U . . .
C4 C 0.6316(2) 0.3772(2) 0.63068(11) 0.0683(6) Uani 1 1 d . . . . .
H4A H 0.596000 0.319167 0.651355 0.082 Uiso 1 1 calc R U . . .
C5 C 0.6521(2) 0.40804(18) 0.56252(11) 0.0578(5) Uani 1 1 d . . . . .
C6 C 0.6349(2) 0.38299(17) 0.46309(10) 0.0538(5) Uani 1 1 d . . . . .
C7 C 0.5959(2) 0.32854(18) 0.42649(11) 0.0596(5) Uani 1 1 d . . . . .
H7 H 0.557800 0.272416 0.448957 0.072 Uiso 1 1 calc R U . . .
C8 C 0.6114(2) 0.35436(17) 0.35991(11) 0.0574(5) Uani 1 1 d . . . . .
C9 C 0.6722(2) 0.44310(17) 0.32411(10) 0.0560(5) Uani 1 1 d . . . . .
C10 C 0.7133(2) 0.49643(18) 0.36022(11) 0.0589(5) Uani 1 1 d . . . . .
H10 H 0.754300 0.551024 0.338082 0.071 Uiso 1 1 calc R U . . .
C11 C 0.69432(19) 0.46981(17) 0.42714(10) 0.0541(5) Uani 1 1 d . . . . .
C12 C 0.7079(2) 0.49525(18) 0.53132(11) 0.0568(5) Uani 1 1 d . . . . .
C13 C 0.7822(2) 0.61476(18) 0.42965(11) 0.0584(5) Uani 1 1 d . . . . .
C14 C 0.6988(2) 0.7096(2) 0.40649(13) 0.0703(6) Uani 1 1 d . . . . .
H14 H 0.608431 0.716429 0.413905 0.084 Uiso 1 1 calc R U . . .
C15 C 0.7513(3) 0.7944(2) 0.37211(14) 0.0789(7) Uani 1 1 d . . . . .
H15 H 0.696773 0.858794 0.354995 0.095 Uiso 1 1 calc R U . . .
C16 C 0.8845(3) 0.7832(2) 0.36335(13) 0.0778(7) Uani 1 1 d . . . . .
C17 C 0.9674(3) 0.6885(2) 0.38702(13) 0.0767(7) Uani 1 1 d . . . . .
H17 H 1.057512 0.682461 0.380716 0.092 Uiso 1 1 calc R U . . .
C18 C 0.9160(2) 0.6022(2) 0.42028(12) 0.0655(6) Uani 1 1 d . . . . .
H18 H 0.970784 0.537198 0.435971 0.079 Uiso 1 1 calc R U . . .
C19 C 0.5229(2) 0.21183(19) 0.34889(11) 0.0640(6) Uani 1 1 d . . . . .
C20 C 0.4155(3) 0.2072(2) 0.32526(13) 0.0723(6) Uani 1 1 d . . . . .
H20 H 0.374588 0.264992 0.295384 0.087 Uiso 1 1 calc R U . . .
C21 C 0.3687(3) 0.1159(2) 0.34626(15) 0.0821(8) Uani 1 1 d . . . . .
H21 H 0.296430 0.112296 0.330515 0.098 Uiso 1 1 calc R U . . .
C22 C 0.4299(3) 0.0312(2) 0.39042(14) 0.0805(7) Uani 1 1 d . . . . .
C23 C 0.5376(3) 0.0345(2) 0.41361(14) 0.0797(7) Uani 1 1 d . . . . .
H23 H 0.578524 -0.023550 0.443304 0.096 Uiso 1 1 calc R U . . .
C24 C 0.5843(3) 0.1246(2) 0.39242(13) 0.0734(6) Uani 1 1 d . . . . .
H24 H 0.657993 0.127004 0.407533 0.088 Uiso 1 1 calc R U . . .
C25 C 0.7401(3) 0.5606(2) 0.21778(12) 0.0729(7) Uani 1 1 d . . . . .
H25 H 0.819844 0.559372 0.233426 0.088 Uiso 1 1 calc R U . . .
C26 C 0.7771(4) 0.5477(3) 0.14866(14) 0.1039(11) Uani 1 1 d . . . . .
H26A H 0.817518 0.603223 0.121850 0.156 Uiso 1 1 calc R U . . .
H26B H 0.699639 0.550811 0.132049 0.156 Uiso 1 1 calc R U . . .
H26C H 0.837712 0.480664 0.147929 0.156 Uiso 1 1 calc R U . . .
C27 C 0.6425(3) 0.6642(3) 0.22230(17) 0.1016(10) Uani 1 1 d . . . . .
H27A H 0.679446 0.721544 0.195244 0.152 Uiso 1 1 calc R U . . .
H27B H 0.622988 0.670235 0.266892 0.152 Uiso 1 1 calc R U . . .
H27C H 0.563266 0.666467 0.207622 0.152 Uiso 1 1 calc R U . . .
Cl3 Cl 0.06986(10) 0.63389(8) 0.23540(4) 0.1106(3) Uani 1 1 d . . . . .
Cl4 Cl 0.16579(9) 0.69954(9) -0.02878(4) 0.1148(3) Uani 1 1 d . . . . .
O1 O 0.5772(2) 0.37877(16) 0.19014(9) 0.0849(5) Uani 1 1 d . . . . .
O2 O 0.3718(3) 0.4649(2) 0.20435(11) 0.1224(9) Uani 1 1 d . . . . .
N5 N 0.2109(2) 0.5812(2) 0.11010(12) 0.0806(6) Uani 1 1 d . . . . .
H5 H 0.252(3) 0.560(3) 0.1481(16) 0.097 Uiso 1 1 d . U . . .
C28 C 0.4734(3) 0.4312(2) 0.16892(13) 0.0754(7) Uani 1 1 d . . . . .
C29 C 0.4730(3) 0.4554(3) 0.09569(12) 0.0811(7) Uani 1 1 d . . . . .
H29A H 0.470352 0.529807 0.077523 0.097 Uiso 1 1 calc R U . . .
H29B H 0.554866 0.415741 0.076109 0.097 Uiso 1 1 calc R U . . .
C30 C 0.3606(3) 0.4306(2) 0.07617(11) 0.0719(6) Uani 1 1 d . . . . .
C31 C 0.3829(4) 0.3443(3) 0.04993(14) 0.0931(9) Uani 1 1 d . . . . .
H31 H 0.467140 0.301091 0.045400 0.112 Uiso 1 1 calc R U . . .
C32 C 0.2822(5) 0.3208(3) 0.03027(16) 0.1073(11) Uani 1 1 d . . . . .
H32 H 0.298926 0.261978 0.013159 0.129 Uiso 1 1 calc R U . . .
C33 C 0.1589(4) 0.3841(3) 0.03607(16) 0.1013(10) Uani 1 1 d . . . . .
H33 H 0.091380 0.368764 0.022559 0.122 Uiso 1 1 calc R U . . .
C34 C 0.1337(3) 0.4706(3) 0.06187(14) 0.0849(8) Uani 1 1 d . . . . .
H34 H 0.049137 0.513346 0.065907 0.102 Uiso 1 1 calc R U . . .
C35 C 0.2341(3) 0.4945(2) 0.08195(11) 0.0703(6) Uani 1 1 d . . . . .
C36 C 0.1058(3) 0.6679(2) 0.10361(14) 0.0778(7) Uani 1 1 d . . . . .
C37 C 0.0330(3) 0.7040(3) 0.15866(17) 0.0879(8) Uani 1 1 d . . . . .
C38 C -0.0652(4) 0.7938(3) 0.1544(2) 0.1125(11) Uani 1 1 d . . . . .
H38 H -0.109605 0.816246 0.191896 0.135 Uiso 1 1 calc R U . . .
C39 C -0.0974(4) 0.8499(4) 0.0948(3) 0.1276(14) Uani 1 1 d . . . . .
H39 H -0.166098 0.910010 0.091933 0.153 Uiso 1 1 calc R U . . .
C40 C -0.0301(4) 0.8195(3) 0.0381(2) 0.1193(13) Uani 1 1 d . . . . .
H40 H -0.053104 0.858355 -0.002511 0.143 Uiso 1 1 calc R U . . .
C41 C 0.0726(3) 0.7296(3) 0.04317(16) 0.0923(9) Uani 1 1 d . . . . .
O3 O 0.6254(19) 0.9399(11) 0.2434(9) 0.181(6) Uani 0.71(4) 1 d D U P A 1
C42 C 0.7270(16) 1.1152(12) 0.1955(8) 0.142(4) Uani 0.71(4) 1 d D U P A 1
H42A H 0.723462 1.095367 0.242189 0.213 Uiso 0.71(4) 1 calc R U P A 1
H42B H 0.742323 1.184797 0.178895 0.213 Uiso 0.71(4) 1 calc R U P A 1
H42C H 0.797143 1.066039 0.176233 0.213 Uiso 0.71(4) 1 calc R U P A 1
C43 C 0.5967(17) 1.1141(10) 0.1783(8) 0.133(4) Uani 0.71(4) 1 d D U P A 1
H43A H 0.528384 1.170630 0.192608 0.159 Uiso 0.71(4) 1 calc R U P A 1
H43B H 0.603910 1.127881 0.131074 0.159 Uiso 0.71(4) 1 calc R U P A 1
C44 C 0.5568(16) 1.0109(9) 0.2090(9) 0.124(3) Uani 0.71(4) 1 d D U P A 1
C45 C 0.4273(16) 1.0016(11) 0.2010(9) 0.123(3) Uani 0.71(4) 1 d D U P A 1
C46 C 0.3488(15) 1.0756(11) 0.1574(7) 0.135(3) Uani 0.71(4) 1 d D U P A 1
H46 H 0.374114 1.137435 0.133854 0.162 Uiso 0.71(4) 1 calc R U P A 1
C47 C 0.2343(13) 1.0584(11) 0.1488(8) 0.153(4) Uani 0.71(4) 1 d D U P A 1
H47 H 0.183349 1.108546 0.119187 0.183 Uiso 0.71(4) 1 calc R U P A 1
C48 C 0.1939(14) 0.9683(13) 0.1831(8) 0.164(4) Uani 0.71(4) 1 d D U P A 1
H48 H 0.116745 0.956800 0.176742 0.197 Uiso 0.71(4) 1 calc R U P A 1
C49 C 0.2694(17) 0.8959(13) 0.2268(10) 0.169(5) Uani 0.71(4) 1 d D U P A 1
H49 H 0.242612 0.834998 0.251052 0.203 Uiso 0.71(4) 1 calc R U P A 1
C50 C 0.384(2) 0.9122(17) 0.2352(16) 0.148(4) Uani 0.71(4) 1 d D U P A 1
H50 H 0.433630 0.861379 0.264970 0.177 Uiso 0.71(4) 1 calc R U P A 1
O3A O 0.662(3) 0.9285(17) 0.2295(16) 0.132(7) Uani 0.29(4) 1 d D U P A 2
C42A C 0.784(5) 1.096(4) 0.183(3) 0.175(13) Uani 0.29(4) 1 d D U P A 2
H42D H 0.794876 1.069550 0.228183 0.263 Uiso 0.29(4) 1 calc R U P A 2
H42E H 0.808574 1.162103 0.166124 0.263 Uiso 0.29(4) 1 calc R U P A 2
H42F H 0.839489 1.045969 0.158537 0.263 Uiso 0.29(4) 1 calc R U P A 2
C43A C 0.641(5) 1.111(2) 0.176(2) 0.136(9) Uani 0.29(4) 1 d D U P A 2
H43C H 0.587070 1.167427 0.195897 0.163 Uiso 0.29(4) 1 calc R U P A 2
H43D H 0.632491 1.131164 0.129984 0.163 Uiso 0.29(4) 1 calc R U P A 2
C44A C 0.591(4) 1.012(2) 0.208(2) 0.138(9) Uani 0.29(4) 1 d D U P A 2
C45A C 0.456(3) 1.007(3) 0.206(2) 0.143(11) Uani 0.29(4) 1 d D U P A 2
C46A C 0.371(3) 1.090(3) 0.170(2) 0.162(13) Uani 0.29(4) 1 d D U P A 2
H46A H 0.399317 1.150147 0.146439 0.195 Uiso 0.29(4) 1 calc R U P A 2
C47A C 0.246(3) 1.083(3) 0.170(2) 0.180(15) Uani 0.29(4) 1 d D U P A 2
H47A H 0.191093 1.138080 0.145194 0.216 Uiso 0.29(4) 1 calc R U P A 2
C48A C 0.202(3) 0.996(4) 0.207(2) 0.190(15) Uani 0.29(4) 1 d D U P A 2
H48A H 0.117077 0.992367 0.207400 0.228 Uiso 0.29(4) 1 calc R U P A 2
C49A C 0.284(3) 0.916(3) 0.244(2) 0.171(14) Uani 0.29(4) 1 d D U P A 2
H49A H 0.252997 0.857677 0.270301 0.205 Uiso 0.29(4) 1 calc R U P A 2
C50A C 0.410(5) 0.920(4) 0.243(4) 0.149(13) Uani 0.29(4) 1 d D U P A 2
H50A H 0.465781 0.863183 0.266958 0.178 Uiso 0.29(4) 1 calc R U P A 2
O4 O 0.9812(8) 0.3474(5) 0.4489(4) 0.121(2) Uani 0.697(12) 1 d D U P B 1
C51 C 1.0929(9) 0.1072(5) 0.4998(4) 0.138(3) Uani 0.697(12) 1 d D U P B 1
H51A H 1.131311 0.070204 0.465728 0.207 Uiso 0.697(12) 1 calc R U P B 1
H51B H 1.083613 0.057153 0.541113 0.207 Uiso 0.697(12) 1 calc R U P B 1
H51C H 1.148707 0.150405 0.501147 0.207 Uiso 0.697(12) 1 calc R U P B 1
C52 C 0.9720(14) 0.1696(9) 0.4875(6) 0.149(4) Uani 0.697(12) 1 d D U P B 1
H52A H 0.923212 0.188568 0.527601 0.179 Uiso 0.697(12) 1 calc R U P B 1
H52B H 0.924661 0.128759 0.475101 0.179 Uiso 0.697(12) 1 calc R U P B 1
C53 C 0.9754(10) 0.2709(7) 0.4337(4) 0.096(2) Uani 0.697(12) 1 d D U P B 1
C54 C 0.9924(14) 0.2701(9) 0.3629(4) 0.086(2) Uani 0.697(12) 1 d D U P B 1
C55 C 1.0404(12) 0.3481(8) 0.3156(4) 0.096(2) Uani 0.697(12) 1 d D U P B 1
H55 H 1.056489 0.402702 0.328275 0.115 Uiso 0.697(12) 1 calc R U P B 1
C56 C 1.0649(16) 0.3482(11) 0.2513(5) 0.128(3) Uani 0.697(12) 1 d D U P B 1
H56 H 1.097293 0.402426 0.220930 0.153 Uiso 0.697(12) 1 calc R U P B 1
C57 C 1.0427(13) 0.2694(9) 0.2305(5) 0.148(4) Uani 0.697(12) 1 d D U P B 1
H57 H 1.058894 0.269759 0.186291 0.177 Uiso 0.697(12) 1 calc R U P B 1
C58 C 0.9955(13) 0.1888(8) 0.2768(5) 0.156(4) Uani 0.697(12) 1 d D U P B 1
H58 H 0.978377 0.135191 0.263476 0.188 Uiso 0.697(12) 1 calc R U P B 1
C59 C 0.9742(14) 0.1880(11) 0.3411(4) 0.119(4) Uani 0.697(12) 1 d D U P B 1
H59 H 0.946878 0.131599 0.371703 0.143 Uiso 0.697(12) 1 calc R U P B 1
O4A O 1.045(2) 0.3303(18) 0.4257(11) 0.166(7) Uani 0.303(12) 1 d D U P B 2
C51A C 0.962(3) 0.143(2) 0.5351(11) 0.181(12) Uani 0.303(12) 1 d D U P B 2
H51D H 0.908150 0.092586 0.554898 0.272 Uiso 0.303(12) 1 calc R U P B 2
H51E H 0.941943 0.194428 0.560274 0.272 Uiso 0.303(12) 1 calc R U P B 2
H51F H 1.052687 0.106426 0.533761 0.272 Uiso 0.303(12) 1 calc R U P B 2
C52A C 0.9368(19) 0.189(2) 0.4750(11) 0.137(7) Uani 0.303(12) 1 d D U P B 2
H52C H 0.848071 0.232744 0.480503 0.164 Uiso 0.303(12) 1 calc R U P B 2
H52D H 0.931165 0.133140 0.457097 0.164 Uiso 0.303(12) 1 calc R U P B 2
C53A C 1.011(3) 0.257(2) 0.4194(10) 0.121(7) Uani 0.303(12) 1 d D U P B 2
C54A C 1.013(4) 0.253(2) 0.3503(9) 0.095(6) Uani 0.303(12) 1 d D U P B 2
C55A C 1.057(4) 0.326(2) 0.2980(11) 0.121(8) Uani 0.303(12) 1 d D U P B 2
H55A H 1.102906 0.369842 0.305255 0.145 Uiso 0.303(12) 1 calc R U P B 2
C56A C 1.036(5) 0.338(3) 0.2365(13) 0.157(9) Uani 0.303(12) 1 d D U P B 2
H56A H 1.064352 0.390211 0.202419 0.189 Uiso 0.303(12) 1 calc R U P B 2
C57A C 0.974(3) 0.271(2) 0.2247(13) 0.162(8) Uani 0.303(12) 1 d D U P B 2
H57A H 0.963179 0.276187 0.182174 0.195 Uiso 0.303(12) 1 calc R U P B 2
C58A C 0.926(2) 0.198(2) 0.2761(14) 0.158(7) Uani 0.303(12) 1 d D U P B 2
H58A H 0.888359 0.149735 0.268108 0.189 Uiso 0.303(12) 1 calc R U P B 2
C59A C 0.936(3) 0.195(3) 0.3377(13) 0.130(7) Uani 0.303(12) 1 d D U P B 2
H59A H 0.890439 0.153957 0.372562 0.156 Uiso 0.303(12) 1 calc R U P B 2
O5 O 0.6632(15) 1.0492(9) 0.0169(8) 0.175(6) Uani 0.5 1 d . . P C -1
C60 C 0.6489(14) 1.2163(10) -0.0905(7) 0.158(4) Uani 0.5 1 d . U P C -1
H60A H 0.631251 1.266856 -0.130810 0.237 Uiso 0.5 1 calc R U P C -1
H60B H 0.737978 1.175685 -0.095863 0.237 Uiso 0.5 1 calc R U P C -1
H60C H 0.636098 1.252499 -0.056508 0.237 Uiso 0.5 1 calc R U P C -1
C61 C 0.555(2) 1.1424(13) -0.0719(12) 0.118(5) Uani 0.5 1 d . U P C -1
H61A H 0.465574 1.184242 -0.065409 0.141 Uiso 0.5 1 calc R U P C -1
H61B H 0.563180 1.111394 -0.108410 0.141 Uiso 0.5 1 calc R U P C -1
C62 C 0.5766(8) 1.0558(9) -0.0123(5) 0.104(2) Uani 0.5 1 d . U P C -1
C63 C 0.4924(18) 0.9795(11) 0.0088(8) 0.090(2) Uani 0.5 1 d . U P C -1
C64 C 0.5261(9) 0.8921(7) 0.0603(4) 0.113(2) Uani 0.5 1 d . U P C -1
H64 H 0.597241 0.884173 0.080894 0.135 Uiso 0.5 1 calc R U P C -1
C65 C 0.452(3) 0.8180(14) 0.0800(11) 0.120(5) Uani 0.5 1 d . U P C -1
H65 H 0.472951 0.760022 0.114515 0.144 Uiso 0.5 1 calc R U P C -1
C66 C 0.3477(10) 0.8276(9) 0.0502(5) 0.114(3) Uani 0.5 1 d . U P C -1
H66 H 0.295287 0.779206 0.065791 0.137 Uiso 0.5 1 calc R U P C -1
C67 C 0.3216(18) 0.9093(11) -0.0028(8) 0.115(3) Uani 0.5 1 d . U P C -1
H67 H 0.257190 0.912698 -0.026585 0.138 Uiso 0.5 1 calc R U P C -1
C68 C 0.3903(11) 0.9862(9) -0.0210(5) 0.105(3) Uani 0.5 1 d . U P C -1
H68 H 0.366240 1.044696 -0.054676 0.126 Uiso 0.5 1 calc R U P C -1
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'
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'
Cl Cl 0.3639 0.7018 '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
C11 N1 C12 121.48(17) . . ?
C11 N1 C13 118.41(17) . . ?
C12 N1 C13 120.10(17) . . ?
C6 N2 C5 118.47(17) . . ?
C8 N3 C19 125.3(2) . . ?
C9 N4 C25 125.6(2) . . ?
C2 C1 C12 119.3(2) . . ?
C1 C2 C3 121.7(2) . . ?
C4 C3 C2 119.4(2) . . ?
C3 C4 C5 121.1(2) . . ?
N2 C5 C4 118.87(19) . . ?
N2 C5 C12 121.83(19) . . ?
C4 C5 C12 119.3(2) . . ?
N2 C6 C7 119.16(18) . . ?
N2 C6 C11 123.31(19) . . ?
C7 C6 C11 117.53(19) . . ?
C8 C7 C6 123.10(19) . . ?
C7 C8 N3 123.96(19) . . ?
C7 C8 C9 118.60(19) . . ?
N3 C8 C9 117.43(19) . . ?
N4 C9 C10 121.57(19) . . ?
N4 C9 C8 119.86(19) . . ?
C10 C9 C8 118.56(19) . . ?
C11 C10 C9 121.47(19) . . ?
C10 C11 N1 122.68(18) . . ?
C10 C11 C6 120.70(19) . . ?
N1 C11 C6 116.61(18) . . ?
N1 C12 C1 122.42(19) . . ?
N1 C12 C5 118.25(19) . . ?
C1 C12 C5 119.3(2) . . ?
C18 C13 C14 122.1(2) . . ?
C18 C13 N1 119.0(2) . . ?
C14 C13 N1 118.90(19) . . ?
C13 C14 C15 118.9(2) . . ?
C16 C15 C14 119.4(3) . . ?
C15 C16 C17 121.5(2) . . ?
C15 C16 Cl1 119.5(2) . . ?
C17 C16 Cl1 119.1(2) . . ?
C16 C17 C18 119.6(2) . . ?
C13 C18 C17 118.5(2) . . ?
C20 C19 C24 119.5(2) . . ?
C20 C19 N3 118.0(2) . . ?
C24 C19 N3 122.3(2) . . ?
C19 C20 C21 119.8(3) . . ?
C22 C21 C20 119.5(3) . . ?
C23 C22 C21 121.2(2) . . ?
C23 C22 Cl2 118.5(2) . . ?
C21 C22 Cl2 120.4(2) . . ?
C22 C23 C24 119.2(3) . . ?
C23 C24 C19 120.7(2) . . ?
N4 C25 C26 109.1(2) . . ?
N4 C25 C27 110.7(2) . . ?
C26 C25 C27 112.0(3) . . ?
C36 N5 C35 125.9(2) . . ?
O2 C28 O1 123.3(3) . . ?
O2 C28 C29 118.9(3) . . ?
O1 C28 C29 117.7(3) . . ?
C30 C29 C28 115.2(2) . . ?
C31 C30 C35 118.3(3) . . ?
C31 C30 C29 120.1(3) . . ?
C35 C30 C29 121.6(3) . . ?
C30 C31 C32 121.4(3) . . ?
C33 C32 C31 119.8(3) . . ?
C32 C33 C34 120.2(3) . . ?
C33 C34 C35 120.3(3) . . ?
C30 C35 C34 120.0(3) . . ?
C30 C35 N5 118.2(2) . . ?
C34 C35 N5 121.7(3) . . ?
N5 C36 C41 123.1(3) . . ?
N5 C36 C37 120.6(3) . . ?
C41 C36 C37 116.1(3) . . ?
C38 C37 C36 122.8(3) . . ?
C38 C37 Cl3 117.9(3) . . ?
C36 C37 Cl3 119.2(2) . . ?
C39 C38 C37 119.3(4) . . ?
C38 C39 C40 121.3(4) . . ?
C39 C40 C41 118.7(4) . . ?
C40 C41 C36 121.7(4) . . ?
C40 C41 Cl4 118.0(3) . . ?
C36 C41 Cl4 120.2(3) . . ?
C44 C43 C42 113.2(9) . . ?
O3 C44 C45 120.5(9) . . ?
O3 C44 C43 120.1(11) . . ?
C45 C44 C43 119.1(8) . . ?
C50 C45 C46 116.9(9) . . ?
C50 C45 C44 119.4(8) . . ?
C46 C45 C44 123.6(8) . . ?
C47 C46 C45 120.7(8) . . ?
C48 C47 C46 121.1(9) . . ?
C49 C48 C47 118.7(10) . . ?
C50 C49 C48 120.5(10) . . ?
C49 C50 C45 122.1(10) . . ?
C44A C43A C42A 112.6(18) . . ?
O3A C44A C45A 115.2(19) . . ?
O3A C44A C43A 122.2(19) . . ?
C45A C44A C43A 121.9(16) . . ?
C50A C45A C46A 118.5(17) . . ?
C50A C45A C44A 119.3(16) . . ?
C46A C45A C44A 122.1(17) . . ?
C47A C46A C45A 120.4(16) . . ?
C48A C47A C46A 120.5(17) . . ?
C49A C48A C47A 119.6(18) . . ?
C48A C49A C50A 120.6(18) . . ?
C49A C50A C45A 120.4(18) . . ?
C51 C52 C53 114.7(10) . . ?
O4 C53 C54 120.3(6) . . ?
O4 C53 C52 118.1(8) . . ?
C54 C53 C52 120.9(8) . . ?
C55 C54 C59 116.3(7) . . ?
C55 C54 C53 119.7(6) . . ?
C59 C54 C53 123.7(7) . . ?
C56 C55 C54 122.4(7) . . ?
C55 C56 C57 120.7(7) . . ?
C56 C57 C58 118.7(8) . . ?
C59 C58 C57 120.2(8) . . ?
C58 C59 C54 121.6(7) . . ?
C51A C52A C53A 130(2) . . ?
O4A C53A C54A 116.0(16) . . ?
O4A C53A C52A 123.1(19) . . ?
C54A C53A C52A 119.1(16) . . ?
C55A C54A C59A 116.7(17) . . ?
C55A C54A C53A 121.1(15) . . ?
C59A C54A C53A 119.8(17) . . ?
C56A C55A C54A 122.3(18) . . ?
C55A C56A C57A 119.4(18) . . ?
C56A C57A C58A 119.9(18) . . ?
C59A C58A C57A 119.8(18) . . ?
C58A C59A C54A 120.8(17) . . ?
C62 C61 C60 115.2(15) . . ?
O5 C62 C63 122.0(13) . . ?
O5 C62 C61 118.9(12) . . ?
C63 C62 C61 119.1(12) . . ?
C68 C63 C64 118.6(10) . . ?
C68 C63 C62 124.1(9) . . ?
C64 C63 C62 117.2(13) . . ?
C65 C64 C63 118.7(12) . . ?
C66 C65 C64 121.6(13) . . ?
C65 C66 C67 119.1(13) . . ?
C66 C67 C68 119.9(13) . . ?
C63 C68 C67 121.9(11) . . ?
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 C16 1.733(2) . ?
Cl2 C22 1.744(3) . ?
N1 C11 1.378(3) . ?
N1 C12 1.381(3) . ?
N1 C13 1.452(3) . ?
N2 C6 1.318(3) . ?
N2 C5 1.377(3) . ?
N3 C8 1.369(3) . ?
N3 C19 1.416(3) . ?
N4 C9 1.319(3) . ?
N4 C25 1.477(3) . ?
C1 C2 1.370(3) . ?
C1 C12 1.407(3) . ?
C2 C3 1.394(4) . ?
C3 C4 1.365(4) . ?
C4 C5 1.394(3) . ?
C5 C12 1.411(3) . ?
C6 C7 1.413(3) . ?
C6 C11 1.447(3) . ?
C7 C8 1.361(3) . ?
C8 C9 1.475(3) . ?
C9 C10 1.406(3) . ?
C10 C11 1.367(3) . ?
C13 C18 1.374(3) . ?
C13 C14 1.374(3) . ?
C14 C15 1.378(4) . ?
C15 C16 1.370(4) . ?
C16 C17 1.373(4) . ?
C17 C18 1.382(3) . ?
C19 C20 1.381(3) . ?
C19 C24 1.384(4) . ?
C20 C21 1.391(4) . ?
C21 C22 1.373(4) . ?
C22 C23 1.372(4) . ?
C23 C24 1.376(4) . ?
C25 C26 1.503(4) . ?
C25 C27 1.512(4) . ?
Cl3 C37 1.725(4) . ?
Cl4 C41 1.739(4) . ?
O1 C28 1.242(3) . ?
O2 C28 1.239(4) . ?
N5 C36 1.379(4) . ?
N5 C35 1.413(4) . ?
C28 C29 1.519(4) . ?
C29 C30 1.509(4) . ?
C30 C31 1.384(4) . ?
C30 C35 1.390(4) . ?
C31 C32 1.386(5) . ?
C32 C33 1.361(5) . ?
C33 C34 1.376(5) . ?
C34 C35 1.391(4) . ?
C36 C41 1.393(4) . ?
C36 C37 1.403(4) . ?
C37 C38 1.364(5) . ?
C38 C39 1.356(6) . ?
C39 C40 1.385(6) . ?
C40 C41 1.391(6) . ?
O3 C44 1.206(10) . ?
C42 C43 1.528(11) . ?
C43 C44 1.510(10) . ?
C44 C45 1.480(10) . ?
C45 C50 1.382(9) . ?
C45 C46 1.390(9) . ?
C46 C47 1.375(11) . ?
C47 C48 1.371(11) . ?
C48 C49 1.367(11) . ?
C49 C50 1.362(13) . ?
O3A C44A 1.201(17) . ?
C42A C43A 1.526(18) . ?
C43A C44A 1.517(16) . ?
C44A C45A 1.480(16) . ?
C45A C50A 1.381(16) . ?
C45A C46A 1.383(15) . ?
C46A C47A 1.369(18) . ?
C47A C48A 1.367(17) . ?
C48A C49A 1.364(17) . ?
C49A C50A 1.368(18) . ?
O4 C53 1.196(7) . ?
C51 C52 1.368(13) . ?
C52 C53 1.532(10) . ?
C53 C54 1.500(9) . ?
C54 C55 1.377(8) . ?
C54 C59 1.402(10) . ?
C55 C56 1.351(11) . ?
C56 C57 1.368(12) . ?
C57 C58 1.387(11) . ?
C58 C59 1.353(10) . ?
O4A C53A 1.203(15) . ?
C51A C52A 1.32(2) . ?
C52A C53A 1.514(16) . ?
C53A C54A 1.502(15) . ?
C54A C55A 1.374(15) . ?
C54A C59A 1.406(17) . ?
C55A C56A 1.350(19) . ?
C56A C57A 1.371(19) . ?
C57A C58A 1.381(18) . ?
C58A C59A 1.342(17) . ?
O5 C62 1.200(15) . ?
C60 C61 1.535(18) . ?
C61 C62 1.49(2) . ?
C62 C63 1.478(16) . ?
C63 C68 1.36(2) . ?
C63 C64 1.400(15) . ?
C64 C65 1.38(2) . ?
C65 C66 1.36(2) . ?
C66 C67 1.364(17) . ?
C67 C68 1.366(18) . ?
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
N3 H3 O1 0.89(3) 1.89(3) 2.760(3) 165(3) .
N4 H4 O1 0.86(3) 1.94(3) 2.802(3) 175(3) .
N5 H5 O2 0.95(3) 1.91(4) 2.787(3) 153(3) .
C15 H15 O3 0.93 2.53 3.230(12) 132.3 .
C18 H18 O4 0.93 2.49 3.238(6) 137.7 .
C1 H1 O4A 0.93 2.50 3.21(2) 133.1 2_766
C38 H38 O3A 0.93 2.59 3.33(3) 137.5 1_455
