#------------------------------------------------------------------------------
#$Date: 2020-10-15 00:52:26 +0300 (Thu, 15 Oct 2020) $
#$Revision: 258384 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/81/4518140.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_4518140
loop_
_publ_author_name
'Shang, Xiaobo'
'Song, Inho'
'Lee, Jeong Hyeon'
'Choi, Wanuk'
'Ahn, Jaeyong'
'Ohtsu, Hiroyoshi'
'Kim, Jin Chul'
'Koo, Jin Young'
'Kwak, Sang Kyu'
'Oh, Joon Hak'
_publ_section_title
;
 Surface-Doped Quasi-2D Chiral Organic Single Crystals for Chiroptical
 Sensing
;
_journal_name_full               'ACS Nano'
_journal_paper_doi               10.1021/acsnano.0c07012
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C40 H22 Cl4 N2 O4, C2.5 H5.83 N0.83 O0.83'
_chemical_formula_sum            'C42.5 H27.83 Cl4 N2.83 O4.83'
_chemical_formula_weight         797.31
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2017-07-19 deposited with the CCDC.	2020-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   11.8350(17)
_cell_length_b                   11.8350(17)
_cell_length_c                   43.729(9)
_cell_measurement_reflns_used    99714
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      0.315
_cell_volume                     5304.4(15)
_computing_cell_refinement       'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_data_collection       'PAL BL2D-SMDC Program'
_computing_data_reduction        'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    Mercury
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            36836
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         25.944
_diffrn_reflns_theta_min         1.957
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.589
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2456
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Flack x determined using 5508 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     993
_refine_ls_number_reflns         14253
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0861
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1431P)²+8.1018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2344
_refine_ls_wR_factor_ref         0.2443
_reflns_Friedel_coverage         0.988
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                12836
_reflns_number_total             14253
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nn0c07012_si_008.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        5304.4(19)
_cod_original_formula_sum        'C42.50 H27.83 Cl4 N2.83 O4.83'
_cod_database_code               4518140
_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   0.926
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
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
C1S C 0.672(2) 0.278(2) 0.0398(4) 0.111(7) Uani 0.923(13) 1 d . . P . .
H1S1 H 0.7525 0.3139 0.0278 0.166 Uiso 0.923(13) 1 calc R U P . .
H1S2 H 0.6021 0.2027 0.0290 0.166 Uiso 0.923(13) 1 calc R U P . .
H1S3 H 0.6466 0.3449 0.0423 0.166 Uiso 0.923(13) 1 calc R U P . .
C2S C 0.5892(17) 0.1855(16) 0.0890(4) 0.084(5) Uani 0.923(13) 1 d . . P . .
H2S1 H 0.6180 0.1633 0.1079 0.126 Uiso 0.923(13) 1 calc R U P . .
H2S2 H 0.5609 0.2487 0.0934 0.126 Uiso 0.923(13) 1 calc R U P . .
H2S3 H 0.5163 0.1064 0.0802 0.126 Uiso 0.923(13) 1 calc R U P . .
C3S C 0.8044(18) 0.2328(15) 0.0765(4) 0.081(4) Uani 0.923(13) 1 d . . P . .
H3S H 0.8073 0.2007 0.0962 0.098 Uiso 0.923(13) 1 calc R U P . .
C4S C 0.274(3) 0.154(3) 0.0539(6) 0.100(7) Uani 0.768(17) 1 d . . P . .
H4S1 H 0.2748 0.0948 0.0384 0.150 Uiso 0.768(17) 1 calc R U P . .
H4S2 H 0.3218 0.2440 0.0463 0.150 Uiso 0.768(17) 1 calc R U P . .
H4S3 H 0.3146 0.1470 0.0727 0.150 Uiso 0.768(17) 1 calc R U P . .
C5S C 0.037(3) 0.013(2) 0.0441(6) 0.112(9) Uani 0.768(17) 1 d . . P . .
H5S1 H 0.0771 -0.0227 0.0303 0.168 Uiso 0.768(17) 1 calc R U P . .
H5S2 H -0.0214 -0.0551 0.0584 0.168 Uiso 0.768(17) 1 calc R U P . .
H5S3 H -0.0129 0.0427 0.0320 0.168 Uiso 0.768(17) 1 calc R U P . .
C6S C 0.1078(17) 0.1843(17) 0.0807(3) 0.069(4) Uani 0.768(17) 1 d . . P . .
H6S H 0.0205 0.1670 0.0823 0.083 Uiso 0.768(17) 1 calc R U P . .
N1S N 0.6912(14) 0.2392(13) 0.0684(3) 0.081(4) Uani 0.923(13) 1 d . . P . .
N2S N 0.1348(18) 0.1180(16) 0.0605(3) 0.078(4) Uani 0.768(17) 1 d . . P . .
O1S O 0.8921(14) 0.2640(13) 0.0606(3) 0.090(3) Uani 0.923(13) 1 d . . P . .
O2S O 0.1920(19) 0.2683(17) 0.0978(4) 0.110(6) Uani 0.768(17) 1 d . . P . .
C1 C 0.0263(9) 0.6430(9) 0.3278(2) 0.0443(18) Uani 1 1 d . . . . .
C2 C -0.0448(9) 0.6971(9) 0.3112(2) 0.0457(19) Uani 1 1 d . . . . .
C3 C -0.1294(10) 0.7253(10) 0.3271(2) 0.0475(19) Uani 1 1 d . . . . .
H3 H -0.1356 0.7178 0.3487 0.057 Uiso 1 1 calc R U . . .
C4 C -0.2050(9) 0.7649(9) 0.3107(2) 0.0460(19) Uani 1 1 d . . . . .
C5 C -0.2008(8) 0.7744(9) 0.2791(2) 0.0427(18) Uani 1 1 d . . . . .
C6 C -0.2919(9) 0.7919(10) 0.2598(2) 0.0451(19) Uani 1 1 d . . . . .
C7 C -0.4271(9) 0.7364(9) 0.2641(2) 0.0448(18) Uani 1 1 d . . . . .
C8 C -0.4988(9) 0.7787(9) 0.2467(2) 0.0445(18) Uani 1 1 d . . . . .
H8 H -0.5898 0.7409 0.2502 0.053 Uiso 1 1 calc R U . . .
C9 C -0.4401(9) 0.8732(8) 0.2247(2) 0.0412(17) Uani 1 1 d . . . . .
C10 C -0.5122(9) 0.9270(9) 0.2088(2) 0.0429(18) Uani 1 1 d . . . . .
C11 C -0.3192(9) 1.0628(9) 0.1774(2) 0.0466(19) Uani 1 1 d . . . . .
C12 C -0.2472(8) 1.0094(9) 0.1939(2) 0.0417(17) Uani 1 1 d . . . . .
C13 C -0.1183(8) 1.0551(9) 0.1870(2) 0.0430(18) Uani 1 1 d . . . . .
H13 H -0.0751 1.1240 0.1727 0.052 Uiso 1 1 calc R U . . .
C14 C -0.0501(9) 1.0004(9) 0.2011(2) 0.0442(18) Uani 1 1 d . . . . .
C15 C -0.1129(9) 0.8968(9) 0.2217(2) 0.0421(17) Uani 1 1 d . . . . .
C16 C -0.0610(9) 0.8162(9) 0.2339(2) 0.0448(19) Uani 1 1 d . . . . .
C17 C 0.0168(8) 0.7777(8) 0.2179(2) 0.0413(18) Uani 1 1 d . . . . .
C18 C 0.0731(8) 0.7147(9) 0.2330(2) 0.0434(18) Uani 1 1 d . . . . .
H18 H 0.1236 0.6871 0.2217 0.052 Uiso 1 1 calc R U . . .
C19 C 0.0574(8) 0.6918(9) 0.2634(2) 0.0435(18) Uani 1 1 d . . . . .
C20 C 0.1224(9) 0.6293(9) 0.2790(2) 0.0452(19) Uani 1 1 d . . . . .
C21 C -0.0271(8) 0.7205(9) 0.2801(2) 0.0423(18) Uani 1 1 d . . . . .
C22 C -0.0951(8) 0.7711(9) 0.2642(2) 0.0427(18) Uani 1 1 d . . . . .
C23 C -0.2372(8) 0.8686(9) 0.2331(2) 0.0436(18) Uani 1 1 d . . . . .
C24 C -0.3098(9) 0.9169(9) 0.2170(2) 0.0432(18) Uani 1 1 d . . . . .
C25 C 0.0743(12) 0.4183(11) 0.3409(3) 0.061(3) Uani 1 1 d . . . . .
H25A H 0.1217 0.3805 0.3510 0.092 Uiso 1 1 calc R U . . .
H25B H 0.0232 0.4345 0.3561 0.092 Uiso 1 1 calc R U . . .
H25C H 0.0157 0.3576 0.3254 0.092 Uiso 1 1 calc R U . . .
C26 C 0.1712(10) 0.5463(10) 0.3258(2) 0.051(2) Uani 1 1 d . . . . .
H26 H 0.2138 0.5227 0.3092 0.062 Uiso 1 1 calc R U . . .
C27 C 0.2807(10) 0.6447(10) 0.3455(2) 0.049(2) Uani 1 1 d . . . . .
C28 C 0.3528(12) 0.7760(12) 0.3367(3) 0.062(3) Uani 1 1 d . . . . .
H28 H 0.3292 0.8046 0.3188 0.074 Uiso 1 1 calc R U . . .
C29 C 0.4591(12) 0.8650(13) 0.3542(3) 0.067(3) Uani 1 1 d . . . . .
H29 H 0.5050 0.9545 0.3486 0.080 Uiso 1 1 calc R U . . .
C30 C 0.4973(12) 0.8243(14) 0.3792(3) 0.067(3) Uani 1 1 d . . . . .
H30 H 0.5695 0.8851 0.3911 0.081 Uiso 1 1 calc R U . . .
C31 C 0.4313(12) 0.6956(14) 0.3871(3) 0.067(3) Uani 1 1 d . . . . .
H31 H 0.4602 0.6666 0.4041 0.080 Uiso 1 1 calc R U . . .
C32 C 0.3239(12) 0.6076(12) 0.3710(2) 0.060(2) Uani 1 1 d . . . . .
H32 H 0.2780 0.5191 0.3774 0.072 Uiso 1 1 calc R U . . .
C33 C -0.5614(10) 1.1483(11) 0.1950(3) 0.059(2) Uani 1 1 d . . . . .
H33A H -0.6054 1.1878 0.1841 0.089 Uiso 1 1 calc R U . . .
H33B H -0.6228 1.0818 0.2092 0.089 Uiso 1 1 calc R U . . .
H33C H -0.4872 1.2158 0.2065 0.089 Uiso 1 1 calc R U . . .
C34 C -0.5131(10) 1.0852(9) 0.1721(2) 0.049(2) Uani 1 1 d . . . . .
H34 H -0.4454 1.1585 0.1596 0.059 Uiso 1 1 calc R U . . .
C35 C -0.6163(10) 0.9923(11) 0.1493(2) 0.052(2) Uani 1 1 d . . . . .
C36 C -0.6230(11) 0.8793(11) 0.1391(2) 0.058(2) Uani 1 1 d . . . . .
H36 H -0.5624 0.8559 0.1468 0.070 Uiso 1 1 calc R U . . .
C37 C -0.7137(15) 0.7995(16) 0.1182(3) 0.080(4) Uani 1 1 d . . . . .
H37 H -0.7146 0.7224 0.1118 0.096 Uiso 1 1 calc R U . . .
C38 C -0.8025(15) 0.8278(18) 0.1065(3) 0.085(4) Uani 1 1 d . . . . .
H38 H -0.8667 0.7704 0.0924 0.102 Uiso 1 1 calc R U . . .
C39 C -0.7980(14) 0.9435(19) 0.1156(3) 0.086(5) Uani 1 1 d . . . . .
H39 H -0.8581 0.9665 0.1073 0.103 Uiso 1 1 calc R U . . .
C40 C -0.7034(12) 1.0259(15) 0.1371(2) 0.066(3) Uani 1 1 d . . . . .
H40 H -0.6996 1.1047 0.1433 0.079 Uiso 1 1 calc R U . . .
C41 C 0.1169(10) 1.1314(10) 0.2890(2) 0.051(2) Uani 1 1 d . . . . .
C42 C 0.0389(9) 1.1801(9) 0.2746(2) 0.0456(19) Uani 1 1 d . . . . .
C43 C -0.0901(10) 1.1319(9) 0.2829(2) 0.049(2) Uani 1 1 d . . . . .
H43 H -0.1286 1.0635 0.2975 0.058 Uiso 1 1 calc R U . . .
C44 C -0.1649(9) 1.1816(9) 0.2702(2) 0.0452(19) Uani 1 1 d . . . . .
C45 C -0.1102(9) 1.2830(9) 0.2492(2) 0.0454(19) Uani 1 1 d . . . . .
C46 C -0.1685(8) 1.3601(9) 0.2375(2) 0.0444(18) Uani 1 1 d . . . . .
C47 C -0.2444(8) 1.3977(9) 0.2543(2) 0.0438(18) Uani 1 1 d . . . . .
C48 C -0.3016(8) 1.4635(9) 0.2402(2) 0.0445(18) Uani 1 1 d . . . . .
H48 H -0.3459 1.4962 0.2522 0.053 Uiso 1 1 calc R U . . .
C49 C -0.2938(8) 1.4807(8) 0.2093(2) 0.0427(18) Uani 1 1 d . . . . .
C50 C -0.3626(9) 1.5410(9) 0.1941(2) 0.0453(19) Uani 1 1 d . . . . .
C51 C -0.2916(9) 1.5036(10) 0.1440(2) 0.047(2) Uani 1 1 d . . . . .
C52 C -0.2065(10) 1.4652(9) 0.1604(2) 0.0448(18) Uani 1 1 d . . . . .
C53 C -0.1206(9) 1.4419(10) 0.1436(2) 0.0472(19) Uani 1 1 d . . . . .
H53 H -0.1206 1.4449 0.1219 0.057 Uiso 1 1 calc R U . . .
C54 C -0.0325(9) 1.4134(9) 0.1593(2) 0.0430(18) Uani 1 1 d . . . . .
C55 C -0.0340(8) 1.4044(9) 0.1907(2) 0.0432(18) Uani 1 1 d . . . . .
C56 C 0.0605(9) 1.3931(9) 0.2095(2) 0.0452(18) Uani 1 1 d . . . . .
C57 C 0.1951(9) 1.4561(9) 0.2045(2) 0.0443(18) Uani 1 1 d . . . . .
C58 C 0.2751(9) 1.4218(9) 0.2201(2) 0.0451(18) Uani 1 1 d . . . . .
H58 H 0.3656 1.4637 0.2154 0.054 Uiso 1 1 calc R U . . .
C59 C 0.2236(8) 1.3270(9) 0.2423(2) 0.0434(18) Uani 1 1 d . . . . .
C60 C 0.3037(9) 1.2800(9) 0.2566(2) 0.0459(19) Uani 1 1 d . . . . .
C61 C 0.0919(9) 1.2747(9) 0.2513(2) 0.0460(19) Uani 1 1 d . . . . .
C62 C 0.0142(8) 1.3177(9) 0.2367(2) 0.0436(18) Uani 1 1 d . . . . .
C63 C -0.1413(9) 1.4031(9) 0.2069(2) 0.0438(18) Uani 1 1 d . . . . .
C64 C -0.2143(9) 1.4510(9) 0.1916(2) 0.0445(18) Uani 1 1 d . . . . .
C65 C 0.2993(12) 1.0108(11) 0.2877(3) 0.061(2) Uani 1 1 d . . . . .
H65A H 0.3567 0.9870 0.2986 0.091 Uiso 1 1 calc R U . . .
H65B H 0.2084 0.9502 0.2934 0.091 Uiso 1 1 calc R U . . .
H65C H 0.3101 1.0061 0.2656 0.091 Uiso 1 1 calc R U . . .
C66 C 0.3348(9) 1.1511(10) 0.2965(2) 0.050(2) Uani 1 1 d . . . . .
H66 H 0.4243 1.2087 0.2881 0.060 Uiso 1 1 calc R U . . .
C67 C 0.3446(10) 1.1809(11) 0.3297(2) 0.054(2) Uani 1 1 d . . . . .
C68 C 0.3898(14) 1.3115(13) 0.3381(3) 0.070(3) Uani 1 1 d . . . . .
H68 H 0.4098 1.3757 0.3228 0.084 Uiso 1 1 calc R U . . .
C69 C 0.4051(17) 1.3462(17) 0.3684(3) 0.086(4) Uani 1 1 d . . . . .
H69 H 0.4358 1.4346 0.3738 0.103 Uiso 1 1 calc R U . . .
C70 C 0.3769(16) 1.2560(18) 0.3906(3) 0.083(4) Uani 1 1 d . . . . .
H70 H 0.3878 1.2817 0.4115 0.100 Uiso 1 1 calc R U . . .
C71 C 0.3324(14) 1.1267(16) 0.3831(3) 0.077(4) Uani 1 1 d . . . . .
H71 H 0.3140 1.0639 0.3987 0.092 Uiso 1 1 calc R U . . .
C72 C 0.3151(12) 1.0902(13) 0.3528(3) 0.065(3) Uani 1 1 d . . . . .
H72 H 0.2824 1.0012 0.3476 0.078 Uiso 1 1 calc R U . . .
C73 C -0.5675(12) 1.4540(14) 0.1326(4) 0.073(3) Uani 1 1 d . . . . .
H73A H -0.6272 1.4773 0.1227 0.109 Uiso 1 1 calc R U . . .
H73B H -0.5329 1.4185 0.1174 0.109 Uiso 1 1 calc R U . . .
H73C H -0.6146 1.3883 0.1485 0.109 Uiso 1 1 calc R U . . .
C74 C -0.4556(10) 1.5750(11) 0.1472(2) 0.053(2) Uani 1 1 d . . . . .
H74 H -0.4956 1.6001 0.1641 0.064 Uiso 1 1 calc R U . . .
C75 C -0.3855(12) 1.6936(11) 0.1274(2) 0.055(2) Uani 1 1 d . . . . .
C76 C -0.2591(14) 1.7944(13) 0.1336(3) 0.068(3) Uani 1 1 d . . . . .
H76 H -0.2138 1.7860 0.1506 0.082 Uiso 1 1 calc R U . . .
C77 C -0.199(2) 1.9040(15) 0.1162(3) 0.090(5) Uani 1 1 d . . . . .
H77 H -0.1118 1.9706 0.1204 0.108 Uiso 1 1 calc R U . . .
C78 C -0.268(2) 1.9151(16) 0.0920(4) 0.092(5) Uani 1 1 d . . . . .
H78 H -0.2288 1.9918 0.0798 0.110 Uiso 1 1 calc R U . . .
C79 C -0.388(2) 1.821(2) 0.0854(4) 0.097(5) Uani 1 1 d . . . . .
H79 H -0.4323 1.8304 0.0683 0.116 Uiso 1 1 calc R U . . .
C80 C -0.4497(15) 1.7112(17) 0.1027(3) 0.082(4) Uani 1 1 d . . . . .
H80 H -0.5367 1.6462 0.0979 0.098 Uiso 1 1 calc R U . . .
N1 N 0.1026(7) 0.6076(8) 0.31001(18) 0.0453(16) Uani 1 1 d . . . . .
N2 N -0.4452(7) 1.0230(8) 0.18677(18) 0.0443(16) Uani 1 1 d . . . . .
N3 N 0.2493(8) 1.1900(8) 0.28036(18) 0.0472(16) Uani 1 1 d . . . . .
N4 N -0.3648(7) 1.5393(8) 0.16240(18) 0.0469(17) Uani 1 1 d . . . . .
O1 O 0.0209(7) 0.6297(7) 0.35532(15) 0.0508(15) Uani 1 1 d . . . . .
O2 O 0.1912(7) 0.5972(7) 0.26491(15) 0.0491(14) Uani 1 1 d . . . . .
O3 O -0.6272(6) 0.8889(7) 0.21461(15) 0.0482(14) Uani 1 1 d . . . . .
O4 O -0.2697(7) 1.1406(7) 0.15643(16) 0.0523(15) Uani 1 1 d . . . . .
O5 O 0.0730(7) 1.0442(8) 0.30815(18) 0.0595(17) Uani 1 1 d . . . . .
O6 O 0.4162(7) 1.3185(7) 0.24859(17) 0.0540(16) Uani 1 1 d . . . . .
O7 O -0.4176(7) 1.5875(7) 0.20879(17) 0.0522(15) Uani 1 1 d . . . . .
O8 O -0.2993(7) 1.5035(8) 0.11660(16) 0.0534(16) Uani 1 1 d . . . . .
Cl1 Cl -0.3018(2) 0.8044(3) 0.33240(5) 0.0510(5) Uani 1 1 d . . . . .
Cl2 Cl 0.0311(2) 0.7870(2) 0.17898(5) 0.0479(5) Uani 1 1 d . . . . .
Cl3 Cl -0.5113(2) 0.6087(2) 0.28819(5) 0.0494(5) Uani 1 1 d . . . . .
Cl4 Cl 0.1124(2) 1.0724(2) 0.19364(5) 0.0504(5) Uani 1 1 d . . . . .
Cl5 Cl -0.3266(2) 1.1034(2) 0.27991(5) 0.0513(5) Uani 1 1 d . . . . .
Cl6 Cl 0.2686(2) 1.5880(2) 0.18032(5) 0.0479(5) Uani 1 1 d . . . . .
Cl7 Cl -0.2582(2) 1.3859(2) 0.29326(5) 0.0505(5) Uani 1 1 d . . . . .
Cl8 Cl 0.0618(2) 1.3749(2) 0.13686(5) 0.0485(5) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O1S C3S N1S 123.8(17) . . ?
O2S C6S N2S 122.7(19) . . ?
C2S N1S C1S 119.1(18) . . ?
C2S N1S C3S 116.3(15) . . ?
C1S N1S C3S 123.9(16) . . ?
C6S N2S C5S 122(2) . . ?
C6S N2S C4S 120.9(17) . . ?
C5S N2S C4S 117(2) . . ?
O1 C1 N1 120.7(8) . . ?
O1 C1 C2 122.6(8) . . ?
N1 C1 C2 116.7(8) . . ?
C21 C2 C3 120.0(8) . . ?
C21 C2 C1 120.4(8) . . ?
C3 C2 C1 119.5(8) . . ?
C2 C3 C4 118.9(9) . . ?
C5 C4 C3 122.3(8) . . ?
C5 C4 Cl1 121.9(7) . . ?
C3 C4 Cl1 115.8(7) . . ?
C4 C5 C22 116.7(8) . . ?
C4 C5 C6 126.1(8) . . ?
C22 C5 C6 117.2(8) . . ?
C7 C6 C23 117.3(8) . . ?
C7 C6 C5 127.0(9) . . ?
C23 C6 C5 115.7(8) . . ?
C8 C7 C6 120.6(9) . . ?
C8 C7 Cl3 117.6(7) . . ?
C6 C7 Cl3 121.6(7) . . ?
C9 C8 C7 121.4(8) . . ?
C8 C9 C24 119.0(8) . . ?
C8 C9 C10 121.3(8) . . ?
C24 C9 C10 119.8(8) . . ?
O3 C10 N2 121.1(8) . . ?
O3 C10 C9 121.3(8) . . ?
N2 C10 C9 117.6(8) . . ?
O4 C11 N2 120.6(9) . . ?
O4 C11 C12 121.8(9) . . ?
N2 C11 C12 117.6(8) . . ?
C13 C12 C24 121.1(8) . . ?
C13 C12 C11 119.3(8) . . ?
C24 C12 C11 119.6(8) . . ?
C12 C13 C14 120.3(8) . . ?
C15 C14 C13 120.6(8) . . ?
C15 C14 Cl4 122.4(7) . . ?
C13 C14 Cl4 116.8(7) . . ?
C14 C15 C23 117.7(8) . . ?
C14 C15 C16 126.3(8) . . ?
C23 C15 C16 116.0(8) . . ?
C17 C16 C22 117.2(9) . . ?
C17 C16 C15 125.8(9) . . ?
C22 C16 C15 117.0(8) . . ?
C18 C17 C16 120.4(8) . . ?
C18 C17 Cl2 116.6(6) . . ?
C16 C17 Cl2 122.4(7) . . ?
C19 C18 C17 121.3(8) . . ?
C18 C19 C21 120.3(8) . . ?
C18 C19 C20 120.1(8) . . ?
C21 C19 C20 119.5(8) . . ?
O2 C20 N1 120.9(8) . . ?
O2 C20 C19 121.3(9) . . ?
N1 C20 C19 117.8(7) . . ?
C2 C21 C22 120.6(8) . . ?
C2 C21 C19 121.1(8) . . ?
C22 C21 C19 118.3(8) . . ?
C21 C22 C16 120.6(8) . . ?
C21 C22 C5 118.9(8) . . ?
C16 C22 C5 120.5(8) . . ?
C6 C23 C15 121.6(8) . . ?
C6 C23 C24 119.0(8) . . ?
C15 C23 C24 119.3(8) . . ?
C12 C24 C9 121.2(9) . . ?
C12 C24 C23 118.5(8) . . ?
C9 C24 C23 120.3(8) . . ?
N1 C26 C27 110.7(8) . . ?
N1 C26 C25 111.2(9) . . ?
C27 C26 C25 116.6(9) . . ?
C32 C27 C28 117.1(10) . . ?
C32 C27 C26 121.8(10) . . ?
C28 C27 C26 120.7(9) . . ?
C29 C28 C27 120.3(11) . . ?
C30 C29 C28 120.5(12) . . ?
C29 C30 C31 119.6(11) . . ?
C30 C31 C32 120.9(11) . . ?
C31 C32 C27 121.6(11) . . ?
N2 C34 C33 112.9(8) . . ?
N2 C34 C35 111.2(8) . . ?
C33 C34 C35 114.8(9) . . ?
C36 C35 C40 117.8(11) . . ?
C36 C35 C34 123.1(9) . . ?
C40 C35 C34 119.0(11) . . ?
C37 C36 C35 122.2(12) . . ?
C38 C37 C36 121.4(16) . . ?
C37 C38 C39 118.7(13) . . ?
C38 C39 C40 119.4(14) . . ?
C35 C40 C39 120.4(14) . . ?
O5 C41 N3 119.7(9) . . ?
O5 C41 C42 123.0(9) . . ?
N3 C41 C42 117.3(8) . . ?
C43 C42 C61 118.6(9) . . ?
C43 C42 C41 120.7(9) . . ?
C61 C42 C41 120.7(9) . . ?
C42 C43 C44 121.5(9) . . ?
C45 C44 C43 120.4(9) . . ?
C45 C44 Cl5 122.9(7) . . ?
C43 C44 Cl5 116.6(7) . . ?
C44 C45 C62 118.1(9) . . ?
C44 C45 C46 126.9(8) . . ?
C62 C45 C46 115.0(8) . . ?
C47 C46 C63 116.8(8) . . ?
C47 C46 C45 126.0(8) . . ?
C63 C46 C45 117.1(8) . . ?
C46 C47 C48 120.7(9) . . ?
C46 C47 Cl7 123.3(7) . . ?
C48 C47 Cl7 115.5(7) . . ?
C49 C48 C47 120.2(8) . . ?
C48 C49 C64 121.1(8) . . ?
C48 C49 C50 120.4(8) . . ?
C64 C49 C50 118.4(8) . . ?
O7 C50 N4 121.5(9) . . ?
O7 C50 C49 121.5(9) . . ?
N4 C50 C49 117.0(8) . . ?
O8 C51 N4 121.2(8) . . ?
O8 C51 C52 123.0(8) . . ?
N4 C51 C52 115.7(8) . . ?
C64 C52 C53 120.9(8) . . ?
C64 C52 C51 120.3(8) . . ?
C53 C52 C51 118.8(8) . . ?
C52 C53 C54 119.1(9) . . ?
C55 C54 C53 121.2(8) . . ?
C55 C54 Cl8 122.5(7) . . ?
C53 C54 Cl8 116.0(7) . . ?
C54 C55 C63 117.7(8) . . ?
C54 C55 C56 126.3(8) . . ?
C63 C55 C56 115.9(8) . . ?
C57 C56 C62 116.5(8) . . ?
C57 C56 C55 126.0(9) . . ?
C62 C56 C55 117.3(8) . . ?
C58 C57 C56 122.0(9) . . ?
C58 C57 Cl6 117.4(7) . . ?
C56 C57 Cl6 120.4(8) . . ?
C59 C58 C57 119.9(9) . . ?
C58 C59 C61 119.7(9) . . ?
C58 C59 C60 120.4(8) . . ?
C61 C59 C60 119.9(8) . . ?
O6 C60 N3 119.9(9) . . ?
O6 C60 C59 122.1(9) . . ?
N3 C60 C59 118.1(8) . . ?
C62 C61 C42 120.3(9) . . ?
C62 C61 C59 119.5(8) . . ?
C42 C61 C59 120.2(9) . . ?
C61 C62 C56 119.3(8) . . ?
C61 C62 C45 119.3(8) . . ?
C56 C62 C45 121.4(8) . . ?
C46 C63 C64 121.2(8) . . ?
C46 C63 C55 120.5(8) . . ?
C64 C63 C55 118.3(8) . . ?
C52 C64 C49 122.3(8) . . ?
C52 C64 C63 120.0(8) . . ?
C49 C64 C63 117.7(8) . . ?
N3 C66 C67 112.1(8) . . ?
N3 C66 C65 110.7(8) . . ?
C67 C66 C65 116.5(9) . . ?
C72 C67 C68 118.1(11) . . ?
C72 C67 C66 124.7(11) . . ?
C68 C67 C66 117.2(10) . . ?
C69 C68 C67 120.2(12) . . ?
C70 C69 C68 120.8(14) . . ?
C69 C70 C71 120.5(12) . . ?
C72 C71 C70 119.2(12) . . ?
C71 C72 C67 121.2(13) . . ?
N4 C74 C75 112.5(8) . . ?
N4 C74 C73 109.4(9) . . ?
C75 C74 C73 117.0(10) . . ?
C76 C75 C80 117.0(12) . . ?
C76 C75 C74 122.9(9) . . ?
C80 C75 C74 120.0(11) . . ?
C77 C76 C75 122.3(13) . . ?
C76 C77 C78 117.7(17) . . ?
C79 C78 C77 121.5(15) . . ?
C78 C79 C80 121.3(14) . . ?
C79 C80 C75 120.2(15) . . ?
C20 N1 C1 124.2(7) . . ?
C20 N1 C26 117.4(7) . . ?
C1 N1 C26 118.4(8) . . ?
C11 N2 C10 124.0(8) . . ?
C11 N2 C34 117.6(8) . . ?
C10 N2 C34 118.4(7) . . ?
C60 N3 C41 123.3(8) . . ?
C60 N3 C66 117.8(8) . . ?
C41 N3 C66 118.9(8) . . ?
C50 N4 C51 124.9(8) . . ?
C50 N4 C74 116.8(7) . . ?
C51 N4 C74 118.2(8) . . ?
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
C1S N1S 1.39(2) . ?
C2S N1S 1.38(2) . ?
C3S O1S 1.15(2) . ?
C3S N1S 1.42(2) . ?
C4S N2S 1.50(3) . ?
C5S N2S 1.40(3) . ?
C6S O2S 1.24(2) . ?
C6S N2S 1.32(2) . ?
C1 O1 1.213(11) . ?
C1 N1 1.404(12) . ?
C1 C2 1.478(13) . ?
C2 C21 1.383(13) . ?
C2 C3 1.389(13) . ?
C3 C4 1.397(14) . ?
C4 C5 1.387(13) . ?
C4 Cl1 1.721(9) . ?
C5 C22 1.429(12) . ?
C5 C6 1.464(12) . ?
C6 C7 1.406(13) . ?
C6 C23 1.419(13) . ?
C7 C8 1.406(13) . ?
C7 Cl3 1.697(10) . ?
C8 C9 1.371(13) . ?
C9 C24 1.400(12) . ?
C9 C10 1.469(12) . ?
C10 O3 1.228(11) . ?
C10 N2 1.396(12) . ?
C11 O4 1.221(12) . ?
C11 N2 1.382(12) . ?
C11 C12 1.479(13) . ?
C12 C13 1.372(12) . ?
C12 C24 1.400(13) . ?
C13 C14 1.405(13) . ?
C14 C15 1.397(13) . ?
C14 Cl4 1.700(9) . ?
C15 C23 1.426(12) . ?
C15 C16 1.470(13) . ?
C16 C17 1.401(12) . ?
C16 C22 1.411(13) . ?
C17 C18 1.390(13) . ?
C17 Cl2 1.707(9) . ?
C18 C19 1.352(13) . ?
C19 C21 1.409(12) . ?
C19 C20 1.474(13) . ?
C20 O2 1.223(11) . ?
C20 N1 1.379(12) . ?
C21 C22 1.404(13) . ?
C23 C24 1.432(13) . ?
C25 C26 1.520(15) . ?
C26 N1 1.499(12) . ?
C26 C27 1.508(14) . ?
C27 C32 1.385(14) . ?
C27 C28 1.401(16) . ?
C28 C29 1.398(17) . ?
C29 C30 1.358(19) . ?
C30 C31 1.36(2) . ?
C31 C32 1.369(18) . ?
C33 C34 1.523(14) . ?
C34 N2 1.480(12) . ?
C34 C35 1.534(14) . ?
C35 C36 1.374(16) . ?
C35 C40 1.383(14) . ?
C36 C37 1.365(17) . ?
C37 C38 1.35(2) . ?
C38 C39 1.40(3) . ?
C39 C40 1.41(2) . ?
C41 O5 1.226(12) . ?
C41 N3 1.411(13) . ?
C41 C42 1.453(14) . ?
C42 C43 1.385(14) . ?
C42 C61 1.408(13) . ?
C43 C44 1.399(14) . ?
C44 C45 1.389(13) . ?
C44 Cl5 1.710(10) . ?
C45 C62 1.425(12) . ?
C45 C46 1.482(13) . ?
C46 C47 1.394(13) . ?
C46 C63 1.412(13) . ?
C47 C48 1.407(13) . ?
C47 Cl7 1.710(10) . ?
C48 C49 1.360(13) . ?
C49 C64 1.392(12) . ?
C49 C50 1.483(13) . ?
C50 O7 1.224(12) . ?
C50 N4 1.384(12) . ?
C51 O8 1.202(12) . ?
C51 N4 1.393(11) . ?
C51 C52 1.483(12) . ?
C52 C64 1.373(13) . ?
C52 C53 1.389(14) . ?
C53 C54 1.422(13) . ?
C54 C55 1.377(13) . ?
C54 Cl8 1.711(9) . ?
C55 C63 1.446(12) . ?
C55 C56 1.448(13) . ?
C56 C57 1.397(13) . ?
C56 C62 1.421(13) . ?
C57 C58 1.383(14) . ?
C57 Cl6 1.718(10) . ?
C58 C59 1.375(13) . ?
C59 C61 1.415(12) . ?
C59 C60 1.458(13) . ?
C60 O6 1.223(12) . ?
C60 N3 1.395(12) . ?
C61 C62 1.407(13) . ?
C63 C64 1.414(13) . ?
C65 C66 1.544(15) . ?
C66 N3 1.483(12) . ?
C66 C67 1.485(15) . ?
C67 C72 1.384(16) . ?
C67 C68 1.409(17) . ?
C68 C69 1.369(19) . ?
C69 C70 1.36(2) . ?
C70 C71 1.39(2) . ?
C71 C72 1.378(19) . ?
C73 C74 1.521(16) . ?
C74 N4 1.493(12) . ?
C74 C75 1.498(16) . ?
C75 C76 1.396(18) . ?
C75 C80 1.397(16) . ?
C76 C77 1.360(19) . ?
C77 C78 1.39(2) . ?
C78 C79 1.33(3) . ?
C79 C80 1.36(2) . ?
