#------------------------------------------------------------------------------
#$Date: 2020-06-05 12:39:06 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252673 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126413.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_7126413
loop_
_publ_author_name
'Li, Kuofei'
'Zhu, Yunhui'
'Yao, Bing'
'Chen, Yuannan'
'Deng, Hao'
'Zhang, Qisheng'
'Zhan, Hongmei'
'Xie, Zhiyuan'
'Cheng, Yanxiang'
_publ_section_title
;
 Rotation-restricted thermally activated delayed fluorescence compounds
 for efficient solution-processed OLEDs with EQEs of up to 24.3% and small
 roll-off.
;
_journal_issue                   44
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5957
_journal_page_last               5960
_journal_paper_doi               10.1039/d0cc01738h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C53 H46 N4'
_chemical_formula_sum            'C53 H46 N4'
_chemical_formula_weight         738.94
_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
;
2019-10-18 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                102.506(2)
_cell_angle_beta                 97.611(2)
_cell_angle_gamma                102.676(2)
_cell_formula_units_Z            2
_cell_length_a                   11.7669(10)
_cell_length_b                   12.1939(10)
_cell_length_c                   15.1362(12)
_cell_measurement_reflns_used    1392
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      2.18
_cell_volume                     2031.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL (Sheldrick,2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10842
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.770
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         7288
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1327
_refine_ls_R_factor_gt           0.0758
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1459P)²+0.0961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1994
_refine_ls_wR_factor_ref         0.2624
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4238
_reflns_number_total             7288
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc01738h2.cif
_cod_data_source_block           C113
_cod_depositor_comments
'Adding full bibliography for 7126413--7126415.cif.'
_cod_database_code               7126413
_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   0.978
_shelx_estimated_absorpt_t_max   0.986
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
C1 C -0.2060(3) 0.3602(3) 0.4144(2) 0.0322(8) Uani 1 1 d . . . . .
C2 C -0.1544(3) 0.3565(3) 0.5010(2) 0.0322(8) Uani 1 1 d . . . . .
H2 H -0.1823 0.3908 0.5536 0.039 Uiso 1 1 calc R U . . .
C3 C -0.0622(3) 0.3032(3) 0.5119(2) 0.0289(8) Uani 1 1 d . . . . .
C4 C 0.0055(3) 0.2901(3) 0.5929(2) 0.0289(8) Uani 1 1 d . . . . .
C5 C 0.0027(3) 0.3279(3) 0.6868(2) 0.0314(8) Uani 1 1 d . . . . .
H5 H -0.0527 0.3701 0.7053 0.038 Uiso 1 1 calc R U . . .
C6 C 0.0808(4) 0.3038(3) 0.7525(2) 0.0363(9) Uani 1 1 d . . . . .
C7 C 0.1608(3) 0.2412(3) 0.7214(2) 0.0348(9) Uani 1 1 d . . . . .
H7 H 0.2139 0.2243 0.7665 0.042 Uiso 1 1 calc R U . . .
C8 C 0.1683(3) 0.2018(3) 0.6288(2) 0.0301(8) Uani 1 1 d . . . . .
C9 C 0.0877(3) 0.2276(3) 0.5642(2) 0.0276(8) Uani 1 1 d . . . . .
C10 C -0.0190(3) 0.2503(3) 0.4353(2) 0.0284(8) Uani 1 1 d . . . . .
C11 C -0.0680(3) 0.2543(3) 0.3463(2) 0.0317(8) Uani 1 1 d . . . . .
C12 C -0.1605(3) 0.3081(3) 0.3392(2) 0.0325(8) Uani 1 1 d . . . . .
H12 H -0.1953 0.3098 0.2793 0.039 Uiso 1 1 calc R U . . .
C13 C 0.1404(3) 0.1437(3) 0.4112(2) 0.0277(8) Uani 1 1 d . . . . .
C14 C 0.2156(3) 0.2025(3) 0.3657(2) 0.0307(8) Uani 1 1 d . . . . .
H14 H 0.2236 0.2832 0.3721 0.037 Uiso 1 1 calc R U . . .
C15 C 0.2801(3) 0.1450(3) 0.3104(2) 0.0348(9) Uani 1 1 d . . . . .
H15 H 0.3312 0.1860 0.2781 0.042 Uiso 1 1 calc R U . . .
C16 C 0.2700(3) 0.0264(3) 0.3019(2) 0.0309(8) Uani 1 1 d . . . . .
C17 C 0.1950(3) -0.0316(3) 0.3491(2) 0.0339(9) Uani 1 1 d . . . . .
H17 H 0.1883 -0.1117 0.3446 0.041 Uiso 1 1 calc R U . . .
C18 C 0.1295(3) 0.0261(3) 0.4028(2) 0.0320(8) Uani 1 1 d . . . . .
H18 H 0.0768 -0.0148 0.4341 0.038 Uiso 1 1 calc R U . . .
C19 C 0.3449(3) -0.0327(3) 0.2456(2) 0.0332(8) Uani 1 1 d . . . . .
C20 C 0.4916(3) -0.0228(3) 0.1629(2) 0.0388(9) Uani 1 1 d . . . . .
C21 C 0.4092(3) -0.1915(3) 0.1952(3) 0.0391(9) Uani 1 1 d . . . . .
C22 C -0.0222(3) 0.2116(3) 0.2602(2) 0.0381(9) Uani 1 1 d . . . . .
C23 C 0.0257(4) 0.2946(4) 0.2173(3) 0.0483(11) Uani 1 1 d . . . . .
H23 H 0.0264 0.3735 0.2414 0.058 Uiso 1 1 calc R U . . .
C24 C 0.0731(4) 0.2635(4) 0.1387(3) 0.0591(13) Uani 1 1 d . . . . .
H24 H 0.1070 0.3214 0.1100 0.071 Uiso 1 1 calc R U . . .
C25 C 0.0710(4) 0.1494(4) 0.1027(3) 0.0623(13) Uani 1 1 d . . . . .
H25 H 0.1050 0.1283 0.0501 0.075 Uiso 1 1 calc R U . . .
C26 C 0.0186(4) 0.0648(4) 0.1442(3) 0.0534(12) Uani 1 1 d . . . . .
H26 H 0.0137 -0.0148 0.1186 0.064 Uiso 1 1 calc R U . . .
C27 C -0.0258(4) 0.0972(3) 0.2220(2) 0.0435(10) Uani 1 1 d . . . . .
H27 H -0.0602 0.0393 0.2506 0.052 Uiso 1 1 calc R U . . .
C28 C 0.2578(3) 0.1373(3) 0.6101(2) 0.0308(8) Uani 1 1 d . . . . .
C29 C 0.3659(3) 0.1885(3) 0.5906(3) 0.0387(9) Uani 1 1 d . . . . .
H29 H 0.3802 0.2653 0.5829 0.046 Uiso 1 1 calc R U . . .
C30 C 0.4529(4) 0.1296(3) 0.5824(3) 0.0464(10) Uani 1 1 d . . . . .
H30 H 0.5272 0.1667 0.5706 0.056 Uiso 1 1 calc R U . . .
C31 C 0.4328(4) 0.0171(4) 0.5910(3) 0.0449(10) Uani 1 1 d . . . . .
H31 H 0.4926 -0.0236 0.5844 0.054 Uiso 1 1 calc R U . . .
C32 C 0.3260(4) -0.0360(4) 0.6091(3) 0.0511(11) Uani 1 1 d . . . . .
H32 H 0.3113 -0.1136 0.6150 0.061 Uiso 1 1 calc R U . . .
C33 C 0.2406(4) 0.0242(3) 0.6187(3) 0.0421(10) Uani 1 1 d . . . . .
H33 H 0.1671 -0.0129 0.6316 0.050 Uiso 1 1 calc R U . . .
C34 C 0.5760(3) 0.0461(4) 0.1184(2) 0.0407(10) Uani 1 1 d . . . . .
C35 C 0.5723(4) 0.1581(4) 0.1158(3) 0.0533(12) Uani 1 1 d . . . . .
H35 H 0.5164 0.1918 0.1440 0.064 Uiso 1 1 calc R U . . .
C36 C 0.6484(4) 0.2206(4) 0.0730(3) 0.0614(13) Uani 1 1 d . . . . .
H36 H 0.6443 0.2972 0.0716 0.074 Uiso 1 1 calc R U . . .
C37 C 0.7304(4) 0.1747(5) 0.0321(3) 0.0648(14) Uani 1 1 d . . . . .
H37 H 0.7836 0.2188 0.0030 0.078 Uiso 1 1 calc R U . . .
C38 C 0.7343(4) 0.0637(5) 0.0340(3) 0.0692(15) Uani 1 1 d . . . . .
H38 H 0.7906 0.0309 0.0054 0.083 Uiso 1 1 calc R U . . .
C39 C 0.6574(4) -0.0026(4) 0.0772(3) 0.0563(12) Uani 1 1 d . . . . .
H39 H 0.6612 -0.0794 0.0780 0.068 Uiso 1 1 calc R U . . .
C40 C 0.4018(3) -0.3163(3) 0.1879(3) 0.0425(10) Uani 1 1 d . . . . .
C41 C 0.3345(4) -0.3759(4) 0.2388(3) 0.0532(11) Uani 1 1 d . . . . .
H41 H 0.2919 -0.3366 0.2786 0.064 Uiso 1 1 calc R U . . .
C42 C 0.3281(5) -0.4927(4) 0.2328(4) 0.0659(14) Uani 1 1 d . . . . .
H42 H 0.2814 -0.5333 0.2679 0.079 Uiso 1 1 calc R U . . .
C43 C 0.3911(4) -0.5488(4) 0.1746(3) 0.0632(13) Uani 1 1 d . . . . .
H43 H 0.3874 -0.6285 0.1699 0.076 Uiso 1 1 calc R U . . .
C44 C 0.4581(4) -0.4908(4) 0.1241(4) 0.0653(14) Uani 1 1 d . . . . .
H44 H 0.5001 -0.5305 0.0841 0.078 Uiso 1 1 calc R U . . .
C45 C 0.4654(4) -0.3741(4) 0.1309(3) 0.0541(12) Uani 1 1 d . . . . .
H45 H 0.5138 -0.3336 0.0966 0.065 Uiso 1 1 calc R U . . .
C46 C -0.3096(3) 0.4140(3) 0.3991(3) 0.0345(9) Uani 1 1 d . . . . .
C47 C 0.0834(4) 0.3482(3) 0.8552(2) 0.0438(10) Uani 1 1 d D . . . .
C48 C -0.4257(4) 0.3203(3) 0.3849(3) 0.0567(12) Uani 1 1 d . . . . .
H48A H -0.4324 0.2591 0.3291 0.085 Uiso 1 1 calc R U . . .
H48B H -0.4929 0.3551 0.3783 0.085 Uiso 1 1 calc R U . . .
H48C H -0.4259 0.2868 0.4382 0.085 Uiso 1 1 calc R U . . .
C49 C -0.3122(4) 0.4648(4) 0.3157(3) 0.0505(11) Uani 1 1 d . . . . .
H49A H -0.2354 0.5190 0.3204 0.076 Uiso 1 1 calc R U . . .
H49B H -0.3748 0.5061 0.3136 0.076 Uiso 1 1 calc R U . . .
H49C H -0.3281 0.4019 0.2594 0.076 Uiso 1 1 calc R U . . .
C50 C -0.3045(4) 0.5135(4) 0.4826(3) 0.0524(11) Uani 1 1 d . . . . .
H50A H -0.3238 0.4815 0.5344 0.079 Uiso 1 1 calc R U . . .
H50B H -0.3620 0.5567 0.4667 0.079 Uiso 1 1 calc R U . . .
H50C H -0.2246 0.5659 0.5000 0.079 Uiso 1 1 calc R U . . .
N1 N 0.0723(2) 0.2031(2) 0.46741(18) 0.0274(7) Uani 1 1 d . . . . .
N2 N 0.4204(3) 0.0323(3) 0.2076(2) 0.0386(8) Uani 1 1 d . . . . .
N3 N 0.3320(3) -0.1463(3) 0.2393(2) 0.0380(8) Uani 1 1 d . . . . .
N4 N 0.4911(3) -0.1342(3) 0.1562(2) 0.0418(8) Uani 1 1 d . . . . .
C51 C -0.0338(5) 0.2985(7) 0.8803(5) 0.0630(18) Uani 0.654(10) 1 d D . P A 1
H51A H -0.0240 0.3115 0.9474 0.095 Uiso 0.654(10) 1 calc R U P A 1
H51B H -0.0605 0.2149 0.8512 0.095 Uiso 0.654(10) 1 calc R U P A 1
H51C H -0.0929 0.3370 0.8586 0.095 Uiso 0.654(10) 1 calc R U P A 1
C52 C 0.1157(7) 0.4793(5) 0.8807(4) 0.0630(18) Uani 0.654(10) 1 d D . P A 1
H52A H 0.0634 0.5063 0.8390 0.095 Uiso 0.654(10) 1 calc R U P A 1
H52B H 0.1982 0.5087 0.8753 0.095 Uiso 0.654(10) 1 calc R U P A 1
H52C H 0.1062 0.5080 0.9442 0.095 Uiso 0.654(10) 1 calc R U P A 1
C53 C 0.1804(6) 0.3108(7) 0.9144(4) 0.0630(18) Uani 0.654(10) 1 d D . P A 1
H53A H 0.1837 0.3444 0.9799 0.095 Uiso 0.654(10) 1 calc R U P A 1
H53B H 0.2577 0.3388 0.8984 0.095 Uiso 0.654(10) 1 calc R U P A 1
H53C H 0.1605 0.2259 0.9019 0.095 Uiso 0.654(10) 1 calc R U P A 1
C51' C 0.0141(16) 0.4445(13) 0.8722(10) 0.113(6) Uani 0.346(10) 1 d D . P A 2
H51D H 0.0280 0.4814 0.9383 0.169 Uiso 0.346(10) 1 calc R U P A 2
H51E H -0.0709 0.4092 0.8495 0.169 Uiso 0.346(10) 1 calc R U P A 2
H51F H 0.0418 0.5032 0.8393 0.169 Uiso 0.346(10) 1 calc R U P A 2
C52' C 0.2028(8) 0.3951(17) 0.9170(9) 0.113(6) Uani 0.346(10) 1 d D . P A 2
H52D H 0.1929 0.4179 0.9811 0.169 Uiso 0.346(10) 1 calc R U P A 2
H52E H 0.2469 0.4629 0.8999 0.169 Uiso 0.346(10) 1 calc R U P A 2
H52F H 0.2467 0.3350 0.9103 0.169 Uiso 0.346(10) 1 calc R U P A 2
C53' C 0.0103(16) 0.2440(10) 0.8817(10) 0.113(6) Uani 0.346(10) 1 d D . P A 2
H53D H 0.0556 0.1855 0.8822 0.169 Uiso 0.346(10) 1 calc R U P A 2
H53E H -0.0640 0.2101 0.8368 0.169 Uiso 0.346(10) 1 calc R U P A 2
H53F H -0.0075 0.2697 0.9431 0.169 Uiso 0.346(10) 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 0.0033 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'
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
C2 C1 C12 116.9(3) . . ?
C2 C1 C46 122.4(3) . . ?
C12 C1 C46 120.6(3) . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C10 121.4(3) . . ?
C2 C3 C4 131.0(3) . . ?
C10 C3 C4 107.6(3) . . ?
C5 C4 C9 120.6(3) . . ?
C5 C4 C3 132.0(3) . . ?
C9 C4 C3 107.4(3) . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 117.7(3) . . ?
C5 C6 C47 121.3(3) . . ?
C7 C6 C47 121.0(3) . . ?
C8 C7 C6 124.9(3) . . ?
C8 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
C7 C8 C9 115.9(3) . . ?
C7 C8 C28 116.8(3) . . ?
C9 C8 C28 127.3(3) . . ?
N1 C9 C8 130.7(3) . . ?
N1 C9 C4 108.4(3) . . ?
C8 C9 C4 120.8(3) . . ?
N1 C10 C11 132.2(3) . . ?
N1 C10 C3 108.4(3) . . ?
C11 C10 C3 119.3(3) . . ?
C12 C11 C10 117.0(3) . . ?
C12 C11 C22 118.3(3) . . ?
C10 C11 C22 124.6(3) . . ?
C11 C12 C1 124.7(3) . . ?
C11 C12 H12 117.7 . . ?
C1 C12 H12 117.7 . . ?
C14 C13 C18 119.9(3) . . ?
C14 C13 N1 120.2(3) . . ?
C18 C13 N1 119.8(3) . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 C19 121.7(3) . . ?
C15 C16 C19 119.3(3) . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
N2 C19 N3 125.6(3) . . ?
N2 C19 C16 117.2(3) . . ?
N3 C19 C16 117.1(3) . . ?
N4 C20 N2 124.6(3) . . ?
N4 C20 C34 118.5(3) . . ?
N2 C20 C34 116.9(3) . . ?
N3 C21 N4 125.7(3) . . ?
N3 C21 C40 116.8(3) . . ?
N4 C21 C40 117.5(3) . . ?
C23 C22 C27 118.6(3) . . ?
C23 C22 C11 116.4(3) . . ?
C27 C22 C11 125.0(3) . . ?
C22 C23 C24 120.4(4) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 120.2(4) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.4(4) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C27 C26 C25 119.5(4) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C22 121.9(4) . . ?
C26 C27 H27 119.0 . . ?
C22 C27 H27 119.0 . . ?
C33 C28 C29 117.2(3) . . ?
C33 C28 C8 120.4(3) . . ?
C29 C28 C8 122.2(3) . . ?
C30 C29 C28 121.0(3) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C31 C30 C29 120.3(4) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C30 119.8(4) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C33 C32 C31 119.3(4) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C32 C33 C28 122.3(4) . . ?
C32 C33 H33 118.8 . . ?
C28 C33 H33 118.8 . . ?
C39 C34 C35 119.4(4) . . ?
C39 C34 C20 119.9(4) . . ?
C35 C34 C20 120.6(3) . . ?
C36 C35 C34 120.6(4) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C37 121.1(5) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 H36 119.5 . . ?
C38 C37 C36 118.6(4) . . ?
C38 C37 H37 120.7 . . ?
C36 C37 H37 120.7 . . ?
C37 C38 C39 121.6(4) . . ?
C37 C38 H38 119.2 . . ?
C39 C38 H38 119.2 . . ?
C34 C39 C38 118.6(4) . . ?
C34 C39 H39 120.7 . . ?
C38 C39 H39 120.7 . . ?
C41 C40 C45 119.1(4) . . ?
C41 C40 C21 120.7(3) . . ?
C45 C40 C21 120.2(4) . . ?
C40 C41 C42 120.9(4) . . ?
C40 C41 H41 119.5 . . ?
C42 C41 H41 119.5 . . ?
C43 C42 C41 118.9(4) . . ?
C43 C42 H42 120.5 . . ?
C41 C42 H42 120.5 . . ?
C44 C43 C42 120.7(4) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C43 C44 C45 120.4(4) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 H44 119.8 . . ?
C44 C45 C40 120.0(4) . . ?
C44 C45 H45 120.0 . . ?
C40 C45 H45 120.0 . . ?
C1 C46 C49 113.2(3) . . ?
C1 C46 C48 108.9(3) . . ?
C49 C46 C48 108.2(3) . . ?
C1 C46 C50 110.9(3) . . ?
C49 C46 C50 106.6(3) . . ?
C48 C46 C50 108.9(3) . . ?
C51 C47 C52 111.6(4) . . ?
C52' C47 C53' 111.0(7) . . ?
C52' C47 C6 117.1(6) . . ?
C51 C47 C6 111.1(4) . . ?
C52 C47 C6 109.2(3) . . ?
C53' C47 C6 104.2(6) . . ?
C52' C47 C51' 107.6(6) . . ?
C53' C47 C51' 105.8(6) . . ?
C6 C47 C51' 110.6(6) . . ?
C51 C47 C53 106.8(4) . . ?
C52 C47 C53 107.0(4) . . ?
C6 C47 C53 111.1(4) . . ?
C46 C48 H48A 109.5 . . ?
C46 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C46 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C46 C49 H49A 109.5 . . ?
C46 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C46 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C46 C50 H50A 109.5 . . ?
C46 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C46 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C10 N1 C9 108.2(3) . . ?
C10 N1 C13 125.7(3) . . ?
C9 N1 C13 126.1(3) . . ?
C19 N2 C20 115.1(3) . . ?
C19 N3 C21 114.1(3) . . ?
C20 N4 C21 114.8(3) . . ?
C47 C51 H51A 109.5 . . ?
C47 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C47 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C47 C52 H52A 109.5 . . ?
C47 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C47 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C47 C53 H53A 109.5 . . ?
C47 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C47 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C47 C51' H51D 109.5 . . ?
C47 C51' H51E 109.5 . . ?
H51D C51' H51E 109.5 . . ?
C47 C51' H51F 109.5 . . ?
H51D C51' H51F 109.5 . . ?
H51E C51' H51F 109.5 . . ?
C47 C52' H52D 109.5 . . ?
C47 C52' H52E 109.5 . . ?
H52D C52' H52E 109.5 . . ?
C47 C52' H52F 109.5 . . ?
H52D C52' H52F 109.5 . . ?
H52E C52' H52F 109.5 . . ?
C47 C53' H53D 109.5 . . ?
C47 C53' H53E 109.5 . . ?
H53D C53' H53E 109.5 . . ?
C47 C53' H53F 109.5 . . ?
H53D C53' H53F 109.5 . . ?
H53E C53' H53F 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
C1 C2 1.384(5) . ?
C1 C12 1.408(4) . ?
C1 C46 1.521(5) . ?
C2 C3 1.391(5) . ?
C2 H2 0.9500 . ?
C3 C10 1.412(4) . ?
C3 C4 1.431(5) . ?
C4 C5 1.403(4) . ?
C4 C9 1.413(4) . ?
C5 C6 1.387(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.402(5) . ?
C6 C47 1.525(5) . ?
C7 C8 1.401(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.405(5) . ?
C8 C28 1.468(5) . ?
C9 N1 1.409(4) . ?
C10 N1 1.405(4) . ?
C10 C11 1.409(5) . ?
C11 C12 1.392(5) . ?
C11 C22 1.509(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.365(4) . ?
C13 C18 1.387(4) . ?
C13 N1 1.435(4) . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.400(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(5) . ?
C16 C19 1.496(4) . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 N2 1.331(4) . ?
C19 N3 1.341(4) . ?
C20 N4 1.338(5) . ?
C20 N2 1.346(4) . ?
C20 C34 1.484(5) . ?
C21 N3 1.339(4) . ?
C21 N4 1.342(5) . ?
C21 C40 1.484(5) . ?
C22 C23 1.376(5) . ?
C22 C27 1.378(5) . ?
C23 C24 1.394(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.366(5) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.386(5) . ?
C28 C29 1.387(5) . ?
C29 C30 1.378(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.378(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.373(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.374(5) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C39 1.380(5) . ?
C34 C35 1.385(6) . ?
C35 C36 1.368(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.368(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.371(7) . ?
C37 H37 0.9500 . ?
C38 C39 1.400(6) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 C41 1.379(6) . ?
C40 C45 1.394(5) . ?
C41 C42 1.392(6) . ?
C41 H41 0.9500 . ?
C42 C43 1.390(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.361(6) . ?
C43 H43 0.9500 . ?
C44 C45 1.387(6) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 C49 1.521(5) . ?
C46 C48 1.532(5) . ?
C46 C50 1.536(5) . ?
C47 C52' 1.497(8) . ?
C47 C51 1.512(6) . ?
C47 C52 1.509(6) . ?
C47 C53' 1.533(8) . ?
C47 C51' 1.567(8) . ?
C47 C53 1.563(6) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C51' H51D 0.9800 . ?
C51' H51E 0.9800 . ?
C51' H51F 0.9800 . ?
C52' H52D 0.9800 . ?
C52' H52E 0.9800 . ?
C52' H52F 0.9800 . ?
C53' H53D 0.9800 . ?
C53' H53E 0.9800 . ?
C53' H53F 0.9800 . ?
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
C12 C1 C2 C3 -0.1(5) . . . . ?
C46 C1 C2 C3 177.9(3) . . . . ?
C1 C2 C3 C10 -0.6(5) . . . . ?
C1 C2 C3 C4 178.9(3) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
C10 C3 C4 C5 178.2(3) . . . . ?
C2 C3 C4 C9 179.5(3) . . . . ?
C10 C3 C4 C9 -0.9(4) . . . . ?
C9 C4 C5 C6 -0.3(5) . . . . ?
C3 C4 C5 C6 -179.3(4) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C4 C5 C6 C47 177.4(3) . . . . ?
C5 C6 C7 C8 0.4(5) . . . . ?
C47 C6 C7 C8 -176.9(3) . . . . ?
C6 C7 C8 C9 -0.5(5) . . . . ?
C6 C7 C8 C28 -179.8(3) . . . . ?
C7 C8 C9 N1 178.9(3) . . . . ?
C28 C8 C9 N1 -2.0(6) . . . . ?
C7 C8 C9 C4 0.3(5) . . . . ?
C28 C8 C9 C4 179.4(3) . . . . ?
C5 C4 C9 N1 -178.8(3) . . . . ?
C3 C4 C9 N1 0.4(4) . . . . ?
C5 C4 C9 C8 0.1(5) . . . . ?
C3 C4 C9 C8 179.3(3) . . . . ?
C2 C3 C10 N1 -179.3(3) . . . . ?
C4 C3 C10 N1 1.0(4) . . . . ?
C2 C3 C10 C11 1.8(5) . . . . ?
C4 C3 C10 C11 -177.9(3) . . . . ?
N1 C10 C11 C12 179.3(3) . . . . ?
C3 C10 C11 C12 -2.0(5) . . . . ?
N1 C10 C11 C22 -4.8(6) . . . . ?
C3 C10 C11 C22 173.8(3) . . . . ?
C10 C11 C12 C1 1.3(5) . . . . ?
C22 C11 C12 C1 -174.8(3) . . . . ?
C2 C1 C12 C11 -0.2(5) . . . . ?
C46 C1 C12 C11 -178.3(3) . . . . ?
C18 C13 C14 C15 0.7(5) . . . . ?
N1 C13 C14 C15 -179.0(3) . . . . ?
C13 C14 C15 C16 -1.0(5) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C14 C15 C16 C19 -177.0(3) . . . . ?
C15 C16 C17 C18 0.9(5) . . . . ?
C19 C16 C17 C18 178.0(3) . . . . ?
C16 C17 C18 C13 -1.3(5) . . . . ?
C14 C13 C18 C17 0.5(5) . . . . ?
N1 C13 C18 C17 -179.8(3) . . . . ?
C17 C16 C19 N2 -175.6(3) . . . . ?
C15 C16 C19 N2 1.5(5) . . . . ?
C17 C16 C19 N3 3.0(5) . . . . ?
C15 C16 C19 N3 -179.8(3) . . . . ?
C12 C11 C22 C23 61.7(5) . . . . ?
C10 C11 C22 C23 -114.1(4) . . . . ?
C12 C11 C22 C27 -117.8(4) . . . . ?
C10 C11 C22 C27 66.4(5) . . . . ?
C27 C22 C23 C24 -2.2(6) . . . . ?
C11 C22 C23 C24 178.3(4) . . . . ?
C22 C23 C24 C25 0.8(7) . . . . ?
C23 C24 C25 C26 1.5(8) . . . . ?
C24 C25 C26 C27 -2.5(7) . . . . ?
C25 C26 C27 C22 1.1(7) . . . . ?
C23 C22 C27 C26 1.2(6) . . . . ?
C11 C22 C27 C26 -179.3(4) . . . . ?
C7 C8 C28 C33 73.7(4) . . . . ?
C9 C8 C28 C33 -105.4(4) . . . . ?
C7 C8 C28 C29 -100.9(4) . . . . ?
C9 C8 C28 C29 79.9(5) . . . . ?
C33 C28 C29 C30 -1.4(5) . . . . ?
C8 C28 C29 C30 173.5(4) . . . . ?
C28 C29 C30 C31 1.6(6) . . . . ?
C29 C30 C31 C32 -0.9(6) . . . . ?
C30 C31 C32 C33 -0.2(6) . . . . ?
C31 C32 C33 C28 0.4(6) . . . . ?
C29 C28 C33 C32 0.3(6) . . . . ?
C8 C28 C33 C32 -174.6(4) . . . . ?
N4 C20 C34 C39 -4.7(6) . . . . ?
N2 C20 C34 C39 175.3(4) . . . . ?
N4 C20 C34 C35 173.8(4) . . . . ?
N2 C20 C34 C35 -6.2(5) . . . . ?
C39 C34 C35 C36 -0.1(7) . . . . ?
C20 C34 C35 C36 -178.5(4) . . . . ?
C34 C35 C36 C37 -0.4(7) . . . . ?
C35 C36 C37 C38 0.6(7) . . . . ?
C36 C37 C38 C39 -0.5(7) . . . . ?
C35 C34 C39 C38 0.2(6) . . . . ?
C20 C34 C39 C38 178.7(4) . . . . ?
C37 C38 C39 C34 0.1(7) . . . . ?
N3 C21 C40 C41 -11.9(6) . . . . ?
N4 C21 C40 C41 169.1(4) . . . . ?
N3 C21 C40 C45 169.7(4) . . . . ?
N4 C21 C40 C45 -9.3(6) . . . . ?
C45 C40 C41 C42 -1.0(7) . . . . ?
C21 C40 C41 C42 -179.4(4) . . . . ?
C40 C41 C42 C43 0.2(7) . . . . ?
C41 C42 C43 C44 0.0(8) . . . . ?
C42 C43 C44 C45 0.7(8) . . . . ?
C43 C44 C45 C40 -1.5(7) . . . . ?
C41 C40 C45 C44 1.7(7) . . . . ?
C21 C40 C45 C44 -179.9(4) . . . . ?
C2 C1 C46 C49 150.4(3) . . . . ?
C12 C1 C46 C49 -31.6(5) . . . . ?
C2 C1 C46 C48 -89.2(4) . . . . ?
C12 C1 C46 C48 88.8(4) . . . . ?
C2 C1 C46 C50 30.6(5) . . . . ?
C12 C1 C46 C50 -151.4(3) . . . . ?
C5 C6 C47 C52' -138.0(10) . . . . ?
C7 C6 C47 C52' 39.3(10) . . . . ?
C5 C6 C47 C51 62.2(5) . . . . ?
C7 C6 C47 C51 -120.5(5) . . . . ?
C5 C6 C47 C52 -61.3(5) . . . . ?
C7 C6 C47 C52 116.0(5) . . . . ?
C5 C6 C47 C53' 99.0(9) . . . . ?
C7 C6 C47 C53' -83.7(9) . . . . ?
C5 C6 C47 C51' -14.2(9) . . . . ?
C7 C6 C47 C51' 163.0(9) . . . . ?
C5 C6 C47 C53 -179.1(4) . . . . ?
C7 C6 C47 C53 -1.8(5) . . . . ?
C11 C10 N1 C9 177.9(3) . . . . ?
C3 C10 N1 C9 -0.8(4) . . . . ?
C11 C10 N1 C13 -0.1(6) . . . . ?
C3 C10 N1 C13 -178.8(3) . . . . ?
C8 C9 N1 C10 -178.5(3) . . . . ?
C4 C9 N1 C10 0.2(3) . . . . ?
C8 C9 N1 C13 -0.5(5) . . . . ?
C4 C9 N1 C13 178.2(3) . . . . ?
C14 C13 N1 C10 66.4(4) . . . . ?
C18 C13 N1 C10 -113.3(4) . . . . ?
C14 C13 N1 C9 -111.3(4) . . . . ?
C18 C13 N1 C9 69.0(4) . . . . ?
N3 C19 N2 C20 -2.9(6) . . . . ?
C16 C19 N2 C20 175.6(3) . . . . ?
N4 C20 N2 C19 -0.8(5) . . . . ?
C34 C20 N2 C19 179.2(3) . . . . ?
N2 C19 N3 C21 4.4(5) . . . . ?
C16 C19 N3 C21 -174.1(3) . . . . ?
N4 C21 N3 C19 -2.5(5) . . . . ?
C40 C21 N3 C19 178.5(3) . . . . ?
N2 C20 N4 C21 2.4(6) . . . . ?
C34 C20 N4 C21 -177.6(3) . . . . ?
N3 C21 N4 C20 -0.6(6) . . . . ?
C40 C21 N4 C20 178.4(3) . . . . ?
