#------------------------------------------------------------------------------
#$Date: 2024-10-10 00:13:45 +0200 (Thu 10 de Oct de 2024) $
#$Revision: 295403 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/28/1572824.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_1572824
loop_
_publ_author_name
'Zhou, Huayi'
'Wang, Runzhe'
'Sun, Mizhen'
'Zhou, Yannan'
'Zhang, Li'
'Song, Jingru'
'Sun, Qikun'
'Zhang, Shitong'
'Yang, Wenjun'
'Xue, Shanfeng'
_publ_section_title
;
 Highly Efficient Pure Organic Near-ultraviolet (NUV) Electro-fluorescent
 Materials with High Electron Mobility and Improved Hole Mobility
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D4SC05625F
_journal_year                    2024
_chemical_formula_sum            'C58 H47 Cl3 N4'
_chemical_formula_weight         906.34
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-06-03 deposited with the CCDC.	2024-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                93.232(8)
_cell_angle_beta                 102.281(8)
_cell_angle_gamma                112.408(7)
_cell_formula_units_Z            2
_cell_length_a                   10.419(4)
_cell_length_b                   10.639(4)
_cell_length_c                   23.685(9)
_cell_measurement_reflns_used    1966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.15
_cell_volume                     2344.0(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.1818
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11692
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.095
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     588
_refine_ls_number_reflns         8154
_refine_ls_number_restraints     186
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.2081
_refine_ls_R_factor_gt           0.1255
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3279
_refine_ls_wR_factor_ref         0.3596
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4278
_reflns_number_total             8154
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc05625f2.cif
_cod_data_source_block           1
_cod_original_cell_volume        2344.1(17)
_cod_database_code               1572824
_shelx_shelxl_version_number     2014/7
_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   0.940
_shelx_estimated_absorpt_t_max   0.981
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 0.8667(3) -0.1338(2) 0.94303(11) 0.0512(7) Uani 1 1 d . . . . .
Cl3 Cl 0.7126(3) 0.0073(3) 0.87717(11) 0.0549(7) Uani 1 1 d . . . . .
Cl2 Cl 0.9822(3) 0.0263(3) 0.85635(12) 0.0606(8) Uani 1 1 d . . . . .
N4 N -0.1953(6) 0.4338(6) 0.0408(2) 0.0157(13) Uani 1 1 d . U . . .
N1 N 1.1493(6) 0.0894(6) 0.6048(2) 0.0168(13) Uani 1 1 d . U . . .
N2 N -0.0315(6) 0.6398(6) 0.0419(3) 0.0202(14) Uani 1 1 d . . . . .
N3 N -0.1511(7) 0.6131(6) -0.0036(3) 0.0237(15) Uani 1 1 d . . . . .
C12 C 1.0529(7) 0.1403(7) 0.5773(3) 0.0166(16) Uani 1 1 d . . . . .
C25 C 0.5224(7) 0.4706(7) 0.3705(3) 0.0152(15) Uani 1 1 d . U . . .
C30 C 0.5057(7) 0.4028(7) 0.3147(3) 0.0165(15) Uani 1 1 d . U . . .
C28 C 0.3336(7) 0.4912(7) 0.2720(3) 0.0172(16) Uani 1 1 d . U . . .
C29 C 0.4111(7) 0.4105(7) 0.2669(3) 0.0164(15) Uani 1 1 d . U . . .
H29 H 0.3976 0.3609 0.2300 0.020 Uiso 1 1 calc R U . . .
C22 C 0.6240(7) 0.4374(7) 0.4139(3) 0.0144(15) Uani 1 1 d . U . . .
C26 C 0.4478(7) 0.5541(7) 0.3764(3) 0.0179(16) Uani 1 1 d . . . . .
H26 H 0.4606 0.6027 0.4135 0.022 Uiso 1 1 calc R U . . .
C19 C 0.8061(7) 0.3279(7) 0.4755(3) 0.0184(16) Uani 1 1 d . U . . .
C23 C 0.6706(7) 0.3505(7) 0.3842(3) 0.0159(15) Uani 1 1 d . U . . .
C24 C 0.7607(7) 0.2973(7) 0.4152(3) 0.0174(16) Uani 1 1 d . U . . .
H24 H 0.7918 0.2392 0.3950 0.021 Uiso 1 1 calc R U . . .
C38 C 0.2299(7) 0.4990(7) 0.2200(3) 0.0179(16) Uani 1 1 d . U . . .
C8 C 1.0076(7) 0.2498(7) 0.4928(3) 0.0170(16) Uani 1 1 d . U . . .
H8 H 1.0291 0.2807 0.4577 0.020 Uiso 1 1 calc R U . . .
C43 C 0.1358(7) 0.3817(8) 0.1797(3) 0.0200(16) Uani 1 1 d . U . . .
H43 H 0.1353 0.2945 0.1868 0.024 Uiso 1 1 calc R U . . .
C11 C 0.9395(7) 0.1525(7) 0.5957(3) 0.0211(17) Uani 1 1 d . U . . .
H11 H 0.9163 0.1194 0.6302 0.025 Uiso 1 1 calc R U . . .
C3 C 1.4532(8) 0.0975(7) 0.5443(3) 0.0209(17) Uani 1 1 d . . . . .
H3 H 1.5344 0.0749 0.5507 0.025 Uiso 1 1 calc R U . . .
C5 C 1.2497(7) 0.1061(7) 0.5723(3) 0.0173(16) Uani 1 1 d . U . . .
C51 C -0.2472(7) 0.4908(7) -0.0043(3) 0.0157(16) Uani 1 1 d . . . . .
C44 C -0.0606(7) 0.5285(7) 0.0686(3) 0.0173(16) Uani 1 1 d . U . . .
C10 C 0.8612(7) 0.2144(7) 0.5621(3) 0.0182(16) Uani 1 1 d . . . . .
H10 H 0.7830 0.2235 0.5738 0.022 Uiso 1 1 calc R U . . .
C6 C 1.2162(7) 0.1652(7) 0.5230(3) 0.0181(16) Uani 1 1 d . U . . .
C1 C 1.3048(7) 0.1918(7) 0.4846(3) 0.0182(16) Uani 1 1 d . U . . .
H1 H 1.2845 0.2335 0.4513 0.022 Uiso 1 1 calc R U . . .
C9 C 0.8952(8) 0.2639(7) 0.5109(3) 0.0190(16) Uani 1 1 d . . . . .
C27 C 0.3559(7) 0.5644(7) 0.3275(3) 0.0205(17) Uani 1 1 d . U . . .
H27 H 0.3063 0.6219 0.3310 0.025 Uiso 1 1 calc R U . . .
C4 C 1.3679(7) 0.0705(7) 0.5838(3) 0.0193(16) Uani 1 1 d . . . . .
H4 H 1.3890 0.0296 0.6172 0.023 Uiso 1 1 calc R U . . .
C31 C 0.6026(7) 0.3256(7) 0.3183(3) 0.0187(16) Uani 1 1 d . U . . .
C52 C -0.3905(7) 0.4282(7) -0.0448(3) 0.0195(16) Uani 1 1 d . U . . .
C21 C 0.6693(7) 0.4698(7) 0.4733(3) 0.0174(16) Uani 1 1 d . U . . .
H21 H 0.6395 0.5297 0.4932 0.021 Uiso 1 1 calc R U . . .
C41 C 0.0355(7) 0.5143(7) 0.1194(3) 0.0186(16) Uani 1 1 d . U . . .
C39 C 0.2259(7) 0.6260(8) 0.2083(3) 0.0205(17) Uani 1 1 d . U . . .
H39 H 0.2904 0.7079 0.2340 0.025 Uiso 1 1 calc R U . . .
C2 C 1.4208(7) 0.1579(7) 0.4949(3) 0.0199(16) Uani 1 1 d . U . . .
H2 H 1.4801 0.1752 0.4683 0.024 Uiso 1 1 calc R U . . .
C13 C 1.1469(8) 0.0310(8) 0.6577(3) 0.0201(17) Uani 1 1 d . . . . .
C45 C -0.2624(7) 0.2969(7) 0.0557(3) 0.0205(17) Uani 1 1 d . U . . .
C7 C 1.0895(7) 0.1893(7) 0.5268(3) 0.0188(16) Uani 1 1 d . . . . .
C50 C -0.3102(8) 0.2837(7) 0.1061(3) 0.0240(18) Uani 1 1 d . . . . .
H50 H -0.3055 0.3617 0.1294 0.029 Uiso 1 1 calc R U . . .
C32 C 0.5156(7) 0.1705(7) 0.2940(3) 0.0183(16) Uani 1 1 d . . . . .
H32A H 0.4718 0.1611 0.2518 0.022 Uiso 1 1 calc R U . . .
H32B H 0.5829 0.1244 0.2981 0.022 Uiso 1 1 calc R U . . .
C42 C 0.0447(8) 0.3897(7) 0.1305(3) 0.0207(17) Uani 1 1 d . . . . .
H42 H -0.0140 0.3087 0.1032 0.025 Uiso 1 1 calc R U . . .
C35 C 0.7170(8) 0.3851(7) 0.2832(3) 0.0212(17) Uani 1 1 d . . . . .
H35A H 0.7801 0.3345 0.2880 0.025 Uiso 1 1 calc R U . . .
H35B H 0.6674 0.3684 0.2412 0.025 Uiso 1 1 calc R U . . .
C40 C 0.1299(7) 0.6329(8) 0.1601(3) 0.0229(17) Uani 1 1 d . U . . .
H40 H 0.1267 0.7192 0.1541 0.027 Uiso 1 1 calc R U . . .
C20 C 0.7593(8) 0.4151(7) 0.5048(3) 0.0204(17) Uani 1 1 d . . . . .
H20 H 0.7893 0.4365 0.5463 0.024 Uiso 1 1 calc R U . . .
C56 C -0.6458(8) 0.2932(7) -0.0676(3) 0.0249(18) Uani 1 1 d . . . . .
H56 H -0.7283 0.2352 -0.0564 0.030 Uiso 1 1 calc R U . . .
C57 C -0.5130(8) 0.3464(7) -0.0277(3) 0.0206(17) Uani 1 1 d . . . . .
H57 H -0.5048 0.3275 0.0113 0.025 Uiso 1 1 calc R U . . .
C18 C 1.0264(9) -0.0806(8) 0.6616(3) 0.0287(19) Uani 1 1 d . . . . .
H18 H 0.9458 -0.1172 0.6287 0.034 Uiso 1 1 calc R U . . .
C33 C 0.3973(8) 0.0955(8) 0.3235(3) 0.0224(17) Uani 1 1 d . U . . .
H33A H 0.3272 0.1385 0.3186 0.027 Uiso 1 1 calc R U . . .
H33B H 0.4394 0.1043 0.3659 0.027 Uiso 1 1 calc R U . . .
C46 C -0.2712(7) 0.1853(7) 0.0198(3) 0.0218(17) Uani 1 1 d . U . . .
H46 H -0.2407 0.1968 -0.0154 0.026 Uiso 1 1 calc R U . . .
C49 C -0.3655(9) 0.1530(8) 0.1219(3) 0.031(2) Uani 1 1 d . . . . .
H49 H -0.3970 0.1417 0.1568 0.038 Uiso 1 1 calc R U . . .
C48 C -0.3747(8) 0.0398(8) 0.0869(3) 0.0273(18) Uani 1 1 d . U . . .
H48 H -0.4147 -0.0492 0.0974 0.033 Uiso 1 1 calc R U . . .
C55 C -0.6582(9) 0.3245(8) -0.1235(4) 0.032(2) Uani 1 1 d . . . . .
H55 H -0.7500 0.2890 -0.1504 0.039 Uiso 1 1 calc R U . . .
C14 C 1.2632(9) 0.0885(8) 0.7054(3) 0.0291(19) Uani 1 1 d . . . . .
H14 H 1.3448 0.1671 0.7035 0.035 Uiso 1 1 calc R U . . .
C17 C 1.0197(9) -0.1395(9) 0.7112(4) 0.035(2) Uani 1 1 d . . . . .
H17 H 0.9362 -0.2164 0.7128 0.042 Uiso 1 1 calc R U . . .
C15 C 1.2593(10) 0.0287(9) 0.7574(3) 0.036(2) Uani 1 1 d . . . . .
H15 H 1.3392 0.0660 0.7906 0.043 Uiso 1 1 calc R U . . .
C53 C -0.4081(9) 0.4568(8) -0.1023(3) 0.032(2) Uani 1 1 d . . . . .
H53 H -0.3267 0.5127 -0.1148 0.038 Uiso 1 1 calc R U . . .
C47 C -0.3257(8) 0.0556(9) 0.0364(3) 0.0305(19) Uani 1 1 d . U . . .
H47 H -0.3295 -0.0222 0.0132 0.037 Uiso 1 1 calc R U . . .
C16 C 1.1381(10) -0.0844(10) 0.7596(4) 0.040(2) Uani 1 1 d . . . . .
H16 H 1.1357 -0.1249 0.7943 0.048 Uiso 1 1 calc R U . . .
C34 C 0.3199(9) -0.0571(8) 0.2973(4) 0.034(2) Uani 1 1 d . . . . .
H34A H 0.2812 -0.0659 0.2551 0.050 Uiso 1 1 calc R U . . .
H34B H 0.2413 -0.1018 0.3155 0.050 Uiso 1 1 calc R U . . .
H34C H 0.3878 -0.1012 0.3045 0.050 Uiso 1 1 calc R U . . .
C36 C 0.8110(9) 0.5400(8) 0.3016(4) 0.033(2) Uani 1 1 d . . . . .
H36A H 0.7494 0.5921 0.2957 0.040 Uiso 1 1 calc R U . . .
H36B H 0.8607 0.5582 0.3436 0.040 Uiso 1 1 calc R U . . .
C54 C -0.5414(9) 0.4052(9) -0.1409(4) 0.040(2) Uani 1 1 d . . . . .
H54 H -0.5518 0.4260 -0.1797 0.048 Uiso 1 1 calc R U . . .
C37 C 0.9218(10) 0.5888(10) 0.2659(4) 0.050(3) Uani 1 1 d . . . . .
H37A H 0.8747 0.5545 0.2244 0.075 Uiso 1 1 calc R U . . .
H37B H 0.9960 0.5538 0.2785 0.075 Uiso 1 1 calc R U . . .
H37C H 0.9659 0.6896 0.2720 0.075 Uiso 1 1 calc R U . . .
C58 C 0.8848(10) 0.0144(9) 0.9091(4) 0.045(2) Uani 1 1 d . . . . .
H58 H 0.9372 0.0978 0.9397 0.054 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
C44 N4 C51 106.6(6) . . ?
C44 N4 C45 124.9(6) . . ?
C51 N4 C45 128.4(5) . . ?
C12 N1 C5 107.8(6) . . ?
C12 N1 C13 125.9(6) . . ?
C5 N1 C13 126.2(6) . . ?
C44 N2 N3 106.5(5) . . ?
C51 N3 N2 109.3(6) . . ?
N1 C12 C11 128.3(6) . . ?
N1 C12 C7 109.8(6) . . ?
C11 C12 C7 121.9(7) . . ?
C26 C25 C30 119.8(6) . . ?
C26 C25 C22 131.4(6) . . ?
C30 C25 C22 108.8(6) . . ?
C29 C30 C25 120.8(7) . . ?
C29 C30 C31 128.6(6) . . ?
C25 C30 C31 110.6(6) . . ?
C29 C28 C27 118.7(6) . . ?
C29 C28 C38 120.3(6) . . ?
C27 C28 C38 121.0(6) . . ?
C30 C29 C28 120.2(6) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C21 C22 C23 120.0(6) . . ?
C21 C22 C25 131.7(6) . . ?
C23 C22 C25 108.2(6) . . ?
C27 C26 C25 118.7(6) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C24 C19 C20 119.0(7) . . ?
C24 C19 C9 121.9(6) . . ?
C20 C19 C9 119.0(6) . . ?
C24 C23 C22 120.2(6) . . ?
C24 C23 C31 129.2(6) . . ?
C22 C23 C31 110.5(6) . . ?
C23 C24 C19 120.4(7) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C43 C38 C39 117.4(7) . . ?
C43 C38 C28 121.6(7) . . ?
C39 C38 C28 121.0(6) . . ?
C9 C8 C7 119.3(7) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C42 C43 C38 121.6(7) . . ?
C42 C43 H43 119.2 . . ?
C38 C43 H43 119.2 . . ?
C10 C11 C12 118.0(7) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C4 C3 C2 120.9(7) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
N1 C5 C4 128.0(6) . . ?
N1 C5 C6 109.9(6) . . ?
C4 C5 C6 122.1(6) . . ?
N3 C51 N4 108.8(6) . . ?
N3 C51 C52 125.2(6) . . ?
N4 C51 C52 125.9(6) . . ?
N2 C44 N4 108.8(6) . . ?
N2 C44 C41 124.6(6) . . ?
N4 C44 C41 126.6(7) . . ?
C11 C10 C9 121.3(7) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C1 C6 C5 119.0(6) . . ?
C1 C6 C7 135.0(7) . . ?
C5 C6 C7 106.0(6) . . ?
C2 C1 C6 120.0(7) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C8 C9 C10 120.1(7) . . ?
C8 C9 C19 120.5(6) . . ?
C10 C9 C19 119.4(6) . . ?
C26 C27 C28 121.6(7) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 H27 119.2 . . ?
C3 C4 C5 117.2(7) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
C30 C31 C23 101.8(5) . . ?
C30 C31 C32 111.5(5) . . ?
C23 C31 C32 112.2(6) . . ?
C30 C31 C35 111.3(6) . . ?
C23 C31 C35 111.9(5) . . ?
C32 C31 C35 108.1(5) . . ?
C57 C52 C53 118.1(7) . . ?
C57 C52 C51 122.7(6) . . ?
C53 C52 C51 119.1(6) . . ?
C22 C21 C20 120.0(7) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C42 C41 C40 116.8(7) . . ?
C42 C41 C44 124.1(6) . . ?
C40 C41 C44 119.1(7) . . ?
C40 C39 C38 120.8(7) . . ?
C40 C39 H39 119.6 . . ?
C38 C39 H39 119.6 . . ?
C1 C2 C3 120.7(7) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C14 C13 C18 119.9(7) . . ?
C14 C13 N1 119.8(7) . . ?
C18 C13 N1 120.3(6) . . ?
C46 C45 C50 122.5(7) . . ?
C46 C45 N4 118.5(6) . . ?
C50 C45 N4 119.0(6) . . ?
C12 C7 C8 119.4(6) . . ?
C12 C7 C6 106.5(6) . . ?
C8 C7 C6 134.1(6) . . ?
C45 C50 C49 118.4(7) . . ?
C45 C50 H50 120.8 . . ?
C49 C50 H50 120.8 . . ?
C33 C32 C31 115.1(6) . . ?
C33 C32 H32A 108.5 . . ?
C31 C32 H32A 108.5 . . ?
C33 C32 H32B 108.5 . . ?
C31 C32 H32B 108.5 . . ?
H32A C32 H32B 107.5 . . ?
C43 C42 C41 121.7(7) . . ?
C43 C42 H42 119.2 . . ?
C41 C42 H42 119.2 . . ?
C36 C35 C31 114.4(6) . . ?
C36 C35 H35A 108.7 . . ?
C31 C35 H35A 108.7 . . ?
C36 C35 H35B 108.7 . . ?
C31 C35 H35B 108.7 . . ?
H35A C35 H35B 107.6 . . ?
C39 C40 C41 121.6(7) . . ?
C39 C40 H40 119.2 . . ?
C41 C40 H40 119.2 . . ?
C21 C20 C19 120.4(6) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C55 C56 C57 120.0(7) . . ?
C55 C56 H56 120.0 . . ?
C57 C56 H56 120.0 . . ?
C56 C57 C52 120.0(7) . . ?
C56 C57 H57 120.0 . . ?
C52 C57 H57 120.0 . . ?
C17 C18 C13 122.2(8) . . ?
C17 C18 H18 118.9 . . ?
C13 C18 H18 118.9 . . ?
C32 C33 C34 111.1(6) . . ?
C32 C33 H33A 109.4 . . ?
C34 C33 H33A 109.4 . . ?
C32 C33 H33B 109.4 . . ?
C34 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C45 C46 C47 118.4(7) . . ?
C45 C46 H46 120.8 . . ?
C47 C46 H46 120.8 . . ?
C48 C49 C50 120.2(7) . . ?
C48 C49 H49 119.9 . . ?
C50 C49 H49 119.9 . . ?
C49 C48 C47 120.4(8) . . ?
C49 C48 H48 119.8 . . ?
C47 C48 H48 119.8 . . ?
C54 C55 C56 121.1(8) . . ?
C54 C55 H55 119.4 . . ?
C56 C55 H55 119.4 . . ?
C13 C14 C15 119.0(8) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C18 C17 C16 118.6(8) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C16 C15 C14 119.6(8) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C54 C53 C52 121.0(7) . . ?
C54 C53 H53 119.5 . . ?
C52 C53 H53 119.5 . . ?
C46 C47 C48 120.0(7) . . ?
C46 C47 H47 120.0 . . ?
C48 C47 H47 120.0 . . ?
C15 C16 C17 120.6(7) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C37 C36 C35 110.9(6) . . ?
C37 C36 H36A 109.5 . . ?
C35 C36 H36A 109.5 . . ?
C37 C36 H36B 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 108.1 . . ?
C55 C54 C53 119.8(8) . . ?
C55 C54 H54 120.1 . . ?
C53 C54 H54 120.1 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
Cl2 C58 Cl3 110.5(5) . . ?
Cl2 C58 Cl1 111.1(5) . . ?
Cl3 C58 Cl1 109.1(5) . . ?
Cl2 C58 H58 108.7 . . ?
Cl3 C58 H58 108.7 . . ?
Cl1 C58 H58 108.7 . . ?
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 C58 1.773(9) . ?
Cl3 C58 1.764(10) . ?
Cl2 C58 1.752(10) . ?
N4 C44 1.368(9) . ?
N4 C51 1.370(9) . ?
N4 C45 1.456(9) . ?
N1 C12 1.380(9) . ?
N1 C5 1.392(8) . ?
N1 C13 1.429(9) . ?
N2 C44 1.337(9) . ?
N2 N3 1.385(8) . ?
N3 C51 1.301(8) . ?
C12 C11 1.389(10) . ?
C12 C7 1.400(9) . ?
C25 C26 1.405(10) . ?
C25 C30 1.413(9) . ?
C25 C22 1.470(10) . ?
C30 C29 1.363(9) . ?
C30 C31 1.518(10) . ?
C28 C29 1.401(10) . ?
C28 C27 1.416(9) . ?
C28 C38 1.485(10) . ?
C29 H29 0.9500 . ?
C22 C21 1.364(9) . ?
C22 C23 1.412(9) . ?
C26 C27 1.377(10) . ?
C26 H26 0.9500 . ?
C19 C24 1.384(9) . ?
C19 C20 1.412(10) . ?
C19 C9 1.498(10) . ?
C23 C24 1.378(10) . ?
C23 C31 1.533(9) . ?
C24 H24 0.9500 . ?
C38 C43 1.401(9) . ?
C38 C39 1.408(10) . ?
C8 C9 1.385(9) . ?
C8 C7 1.406(10) . ?
C8 H8 0.9500 . ?
C43 C42 1.367(10) . ?
C43 H43 0.9500 . ?
C11 C10 1.388(10) . ?
C11 H11 0.9500 . ?
C3 C4 1.393(9) . ?
C3 C2 1.406(10) . ?
C3 H3 0.9500 . ?
C5 C4 1.400(10) . ?
C5 C6 1.398(10) . ?
C51 C52 1.468(9) . ?
C44 C41 1.448(10) . ?
C10 C9 1.408(9) . ?
C10 H10 0.9500 . ?
C6 C1 1.395(9) . ?
C6 C7 1.457(10) . ?
C1 C2 1.366(10) . ?
C1 H1 0.9500 . ?
C27 H27 0.9500 . ?
C4 H4 0.9500 . ?
C31 C32 1.551(9) . ?
C31 C35 1.556(9) . ?
C52 C57 1.401(10) . ?
C52 C53 1.401(10) . ?
C21 C20 1.394(10) . ?
C21 H21 0.9500 . ?
C41 C42 1.400(10) . ?
C41 C40 1.416(9) . ?
C39 C40 1.374(10) . ?
C39 H39 0.9500 . ?
C2 H2 0.9500 . ?
C13 C14 1.376(10) . ?
C13 C18 1.386(10) . ?
C45 C46 1.383(10) . ?
C45 C50 1.383(10) . ?
C50 C49 1.394(10) . ?
C50 H50 0.9500 . ?
C32 C33 1.524(10) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C42 H42 0.9500 . ?
C35 C36 1.540(10) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C40 H40 0.9500 . ?
C20 H20 0.9500 . ?
C56 C55 1.375(11) . ?
C56 C57 1.384(10) . ?
C56 H56 0.9500 . ?
C57 H57 0.9500 . ?
C18 C17 1.364(11) . ?
C18 H18 0.9500 . ?
C33 C34 1.532(10) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C46 C47 1.393(11) . ?
C46 H46 0.9500 . ?
C49 C48 1.382(11) . ?
C49 H49 0.9500 . ?
C48 C47 1.392(10) . ?
C48 H48 0.9500 . ?
C55 C54 1.359(11) . ?
C55 H55 0.9500 . ?
C14 C15 1.419(11) . ?
C14 H14 0.9500 . ?
C17 C16 1.396(12) . ?
C17 H17 0.9500 . ?
C15 C16 1.386(12) . ?
C15 H15 0.9500 . ?
C53 C54 1.374(11) . ?
C53 H53 0.9500 . ?
C47 H47 0.9500 . ?
C16 H16 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C36 C37 1.524(11) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C54 H54 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C58 H58 1.0000 . ?
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
C58 H58 N2 1.00 2.56 3.420(11) 144.4 2_666
C58 H58 Cl1 1.00 2.98 3.703(10) 129.6 2_757
C58 H58 N2 1.00 2.56 3.420(11) 144.4 2_666
C46 H46 Cl3 0.95 2.99 3.716(8) 134.6 1_454
C58 H58 Cl1 1.00 2.98 3.703(10) 129.6 2_757
C58 H58 N2 1.00 2.56 3.420(11) 144.4 2_666
C46 H46 Cl3 0.95 2.99 3.716(8) 134.6 1_454
C58 H58 Cl1 1.00 2.98 3.703(10) 129.6 2_757
C58 H58 N2 1.00 2.56 3.420(11) 144.4 2_666
C46 H46 Cl3 0.95 2.99 3.716(8) 134.6 1_454
C58 H58 Cl1 1.00 2.98 3.703(10) 129.6 2_757
C58 H58 N2 1.00 2.56 3.420(11) 144.4 2_666
C46 H46 Cl3 0.95 2.99 3.716(8) 134.6 1_454
C58 H58 Cl1 1.00 2.98 3.703(10) 129.6 2_757
C58 H58 N2 1.00 2.56 3.420(11) 144.4 2_666
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
C44 N2 N3 C51 -0.3(7) . . . . ?
C5 N1 C12 C11 -176.0(7) . . . . ?
C13 N1 C12 C11 3.5(11) . . . . ?
C5 N1 C12 C7 0.3(7) . . . . ?
C13 N1 C12 C7 179.8(6) . . . . ?
C26 C25 C30 C29 -4.1(10) . . . . ?
C22 C25 C30 C29 176.5(6) . . . . ?
C26 C25 C30 C31 176.7(6) . . . . ?
C22 C25 C30 C31 -2.6(8) . . . . ?
C25 C30 C29 C28 2.9(10) . . . . ?
C31 C30 C29 C28 -178.0(6) . . . . ?
C27 C28 C29 C30 0.2(10) . . . . ?
C38 C28 C29 C30 -179.7(6) . . . . ?
C26 C25 C22 C21 5.2(12) . . . . ?
C30 C25 C22 C21 -175.6(7) . . . . ?
C26 C25 C22 C23 -178.5(7) . . . . ?
C30 C25 C22 C23 0.7(8) . . . . ?
C30 C25 C26 C27 2.1(10) . . . . ?
C22 C25 C26 C27 -178.8(7) . . . . ?
C21 C22 C23 C24 0.6(10) . . . . ?
C25 C22 C23 C24 -176.3(6) . . . . ?
C21 C22 C23 C31 178.4(6) . . . . ?
C25 C22 C23 C31 1.5(7) . . . . ?
C22 C23 C24 C19 0.2(10) . . . . ?
C31 C23 C24 C19 -177.1(6) . . . . ?
C20 C19 C24 C23 -0.3(10) . . . . ?
C9 C19 C24 C23 175.5(6) . . . . ?
C29 C28 C38 C43 42.8(10) . . . . ?
C27 C28 C38 C43 -137.1(7) . . . . ?
C29 C28 C38 C39 -135.1(7) . . . . ?
C27 C28 C38 C39 45.0(10) . . . . ?
C39 C38 C43 C42 0.9(10) . . . . ?
C28 C38 C43 C42 -177.1(6) . . . . ?
N1 C12 C11 C10 176.4(6) . . . . ?
C7 C12 C11 C10 0.5(10) . . . . ?
C12 N1 C5 C4 179.4(7) . . . . ?
C13 N1 C5 C4 -0.1(11) . . . . ?
C12 N1 C5 C6 -1.2(7) . . . . ?
C13 N1 C5 C6 179.3(6) . . . . ?
N2 N3 C51 N4 0.6(7) . . . . ?
N2 N3 C51 C52 177.5(6) . . . . ?
C44 N4 C51 N3 -0.7(7) . . . . ?
C45 N4 C51 N3 -177.2(6) . . . . ?
C44 N4 C51 C52 -177.6(6) . . . . ?
C45 N4 C51 C52 5.9(11) . . . . ?
N3 N2 C44 N4 -0.1(7) . . . . ?
N3 N2 C44 C41 -179.0(6) . . . . ?
C51 N4 C44 N2 0.5(7) . . . . ?
C45 N4 C44 N2 177.1(6) . . . . ?
C51 N4 C44 C41 179.3(6) . . . . ?
C45 N4 C44 C41 -4.1(11) . . . . ?
C12 C11 C10 C9 -0.2(10) . . . . ?
N1 C5 C6 C1 179.5(6) . . . . ?
C4 C5 C6 C1 -1.1(10) . . . . ?
N1 C5 C6 C7 1.6(7) . . . . ?
C4 C5 C6 C7 -179.0(6) . . . . ?
C5 C6 C1 C2 1.2(10) . . . . ?
C7 C6 C1 C2 178.3(7) . . . . ?
C7 C8 C9 C10 -1.8(10) . . . . ?
C7 C8 C9 C19 -180.0(6) . . . . ?
C11 C10 C9 C8 0.8(10) . . . . ?
C11 C10 C9 C19 179.0(6) . . . . ?
C24 C19 C9 C8 42.5(10) . . . . ?
C20 C19 C9 C8 -141.7(7) . . . . ?
C24 C19 C9 C10 -135.7(7) . . . . ?
C20 C19 C9 C10 40.1(9) . . . . ?
C25 C26 C27 C28 1.0(10) . . . . ?
C29 C28 C27 C26 -2.2(10) . . . . ?
C38 C28 C27 C26 177.6(6) . . . . ?
C2 C3 C4 C5 -0.1(9) . . . . ?
N1 C5 C4 C3 179.9(6) . . . . ?
C6 C5 C4 C3 0.6(10) . . . . ?
C29 C30 C31 C23 -175.8(7) . . . . ?
C25 C30 C31 C23 3.3(7) . . . . ?
C29 C30 C31 C32 -55.9(9) . . . . ?
C25 C30 C31 C32 123.2(6) . . . . ?
C29 C30 C31 C35 64.8(9) . . . . ?
C25 C30 C31 C35 -116.1(6) . . . . ?
C24 C23 C31 C30 174.6(7) . . . . ?
C22 C23 C31 C30 -2.9(7) . . . . ?
C24 C23 C31 C32 55.3(9) . . . . ?
C22 C23 C31 C32 -122.2(6) . . . . ?
C24 C23 C31 C35 -66.5(9) . . . . ?
C22 C23 C31 C35 116.0(6) . . . . ?
N3 C51 C52 C57 -141.6(7) . . . . ?
N4 C51 C52 C57 34.8(11) . . . . ?
N3 C51 C52 C53 34.9(11) . . . . ?
N4 C51 C52 C53 -148.7(7) . . . . ?
C23 C22 C21 C20 -1.2(10) . . . . ?
C25 C22 C21 C20 174.8(7) . . . . ?
N2 C44 C41 C42 -147.1(7) . . . . ?
N4 C44 C41 C42 34.3(11) . . . . ?
N2 C44 C41 C40 31.2(10) . . . . ?
N4 C44 C41 C40 -147.4(7) . . . . ?
C43 C38 C39 C40 2.0(10) . . . . ?
C28 C38 C39 C40 -180.0(6) . . . . ?
C6 C1 C2 C3 -0.7(10) . . . . ?
C4 C3 C2 C1 0.2(10) . . . . ?
C12 N1 C13 C14 -121.0(8) . . . . ?
C5 N1 C13 C14 58.4(10) . . . . ?
C12 N1 C13 C18 57.0(10) . . . . ?
C5 N1 C13 C18 -123.6(8) . . . . ?
C44 N4 C45 C46 -104.4(8) . . . . ?
C51 N4 C45 C46 71.5(9) . . . . ?
C44 N4 C45 C50 73.4(9) . . . . ?
C51 N4 C45 C50 -110.7(8) . . . . ?
N1 C12 C7 C8 -178.1(6) . . . . ?
C11 C12 C7 C8 -1.5(10) . . . . ?
N1 C12 C7 C6 0.6(7) . . . . ?
C11 C12 C7 C6 177.3(6) . . . . ?
C9 C8 C7 C12 2.1(10) . . . . ?
C9 C8 C7 C6 -176.2(7) . . . . ?
C1 C6 C7 C12 -178.7(7) . . . . ?
C5 C6 C7 C12 -1.4(7) . . . . ?
C1 C6 C7 C8 -0.2(14) . . . . ?
C5 C6 C7 C8 177.1(7) . . . . ?
C46 C45 C50 C49 1.8(11) . . . . ?
N4 C45 C50 C49 -175.8(6) . . . . ?
C30 C31 C32 C33 -57.1(8) . . . . ?
C23 C31 C32 C33 56.4(8) . . . . ?
C35 C31 C32 C33 -179.7(6) . . . . ?
C38 C43 C42 C41 -3.3(11) . . . . ?
C40 C41 C42 C43 2.8(10) . . . . ?
C44 C41 C42 C43 -178.9(6) . . . . ?
C30 C31 C35 C36 56.2(8) . . . . ?
C23 C31 C35 C36 -57.0(9) . . . . ?
C32 C31 C35 C36 178.9(6) . . . . ?
C38 C39 C40 C41 -2.5(11) . . . . ?
C42 C41 C40 C39 0.1(10) . . . . ?
C44 C41 C40 C39 -178.3(6) . . . . ?
C22 C21 C20 C19 1.1(10) . . . . ?
C24 C19 C20 C21 -0.3(10) . . . . ?
C9 C19 C20 C21 -176.3(6) . . . . ?
C55 C56 C57 C52 -2.2(11) . . . . ?
C53 C52 C57 C56 1.8(11) . . . . ?
C51 C52 C57 C56 178.3(7) . . . . ?
C14 C13 C18 C17 -2.1(12) . . . . ?
N1 C13 C18 C17 179.9(7) . . . . ?
C31 C32 C33 C34 -178.9(6) . . . . ?
C50 C45 C46 C47 -2.3(11) . . . . ?
N4 C45 C46 C47 175.4(6) . . . . ?
C45 C50 C49 C48 -1.4(12) . . . . ?
C50 C49 C48 C47 1.5(12) . . . . ?
C57 C56 C55 C54 1.2(12) . . . . ?
C18 C13 C14 C15 2.3(11) . . . . ?
N1 C13 C14 C15 -179.6(7) . . . . ?
C13 C18 C17 C16 0.5(12) . . . . ?
C13 C14 C15 C16 -1.1(12) . . . . ?
C57 C52 C53 C54 -0.5(12) . . . . ?
C51 C52 C53 C54 -177.1(8) . . . . ?
C45 C46 C47 C48 2.4(11) . . . . ?
C49 C48 C47 C46 -2.0(12) . . . . ?
C14 C15 C16 C17 -0.4(13) . . . . ?
C18 C17 C16 C15 0.7(13) . . . . ?
C31 C35 C36 C37 178.8(7) . . . . ?
C56 C55 C54 C53 0.1(14) . . . . ?
C52 C53 C54 C55 -0.4(14) . . . . ?
