#------------------------------------------------------------------------------
#$Date: 2024-12-06 18:45:40 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296403 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/25/1572536.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_1572536
loop_
_publ_author_name
'Li, Qian'
'Guo, Yusong'
'Lan, Jingbo'
'Yang, Yudong'
'Wu, Di'
'Bin, Zhengyang'
_publ_section_title
;
 Spirobifluorene-based hole-transporting materials for RGB OLEDs with high
 efficiency and low efficiency roll-off.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              16096
_journal_page_last               16102
_journal_paper_doi               10.1039/d4sc04979a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C53 H42 N2'
_chemical_formula_sum            'C53 H42 N2'
_chemical_formula_weight         706.88
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-07-13 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.1121(13)
_cell_length_b                   13.8417(9)
_cell_length_c                   30.0202(17)
_cell_measurement_reflns_used    8257
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.832
_cell_measurement_theta_min      2.267
_cell_volume                     7941.7(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1295
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            45883
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.131
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1531 before and 0.0990 after correction.
The Ratio of minimum to maximum transmission is 0.6978.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       needle
_exptl_crystal_F_000             2992
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0071(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         6971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0537
_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)+(0.0581P)²+1.8339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1548
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4681
_reflns_number_total             6971
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc04979a2.cif
_cod_data_source_block           mo_sbf_0ma_a
_cod_depositor_comments          'Adding full bibliography for 1572536.cif.'
_cod_database_code               1572536
_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_max   0.995
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C10(H10), C13(H13), C14(H14), C19(H19), C20(H20),
 C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C29(H29), C32(H32), C33(H33),
  C34(H34), C35(H35), C36(H36), C37(H37), C41(H41), C42(H42), C43(H43),
 C44(H44), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C31(H31A,H31B,H31C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'
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
N1 N 0.80917(10) 0.53654(15) 0.52219(6) 0.0512(5) Uani 1 1 d . . . . .
N2 N 0.51250(10) 0.75577(16) 0.36981(6) 0.0563(6) Uani 1 1 d . . . . .
C1 C 0.97965(14) 0.21600(19) 0.57650(9) 0.0645(7) Uani 1 1 d . . . . .
H1A H 0.9523 0.1779 0.5978 0.097 Uiso 1 1 calc R U . . .
H1B H 1.0226 0.2390 0.5909 0.097 Uiso 1 1 calc R U . . .
H1C H 0.9918 0.1756 0.5508 0.097 Uiso 1 1 calc R U . . .
C2 C 0.93710(12) 0.30117(17) 0.56111(7) 0.0459(6) Uani 1 1 d . . . . .
C3 C 0.90114(13) 0.30027(18) 0.52114(8) 0.0525(6) Uani 1 1 d . . . . .
H3 H 0.9054 0.2456 0.5022 0.063 Uiso 1 1 calc R U . . .
C4 C 0.85921(12) 0.37618(18) 0.50783(7) 0.0509(6) Uani 1 1 d . . . . .
H4 H 0.8342 0.3724 0.4805 0.061 Uiso 1 1 calc R U . . .
C5 C 0.85353(11) 0.45815(17) 0.53439(7) 0.0426(5) Uani 1 1 d . . . . .
C6 C 0.81072(11) 0.57466(17) 0.47837(7) 0.0419(5) Uani 1 1 d . . . . .
C7 C 0.75112(11) 0.61601(17) 0.45966(6) 0.0417(5) Uani 1 1 d . . . . .
H7 H 0.7092 0.6207 0.4765 0.050 Uiso 1 1 calc R U . . .
C8 C 0.75326(10) 0.65016(16) 0.41633(6) 0.0377(5) Uani 1 1 d . . . . .
C9 C 0.69758(10) 0.68916(16) 0.38758(6) 0.0377(5) Uani 1 1 d . . . . .
C10 C 0.62753(11) 0.70676(17) 0.39617(7) 0.0431(5) Uani 1 1 d . . . . .
H10 H 0.6090 0.6967 0.4252 0.052 Uiso 1 1 calc R U . . .
C11 C 0.58442(11) 0.73955(18) 0.36170(7) 0.0451(6) Uani 1 1 d . . . . .
C12 C 0.47990(11) 0.70901(18) 0.40684(7) 0.0452(6) Uani 1 1 d . . . . .
C13 C 0.47376(13) 0.6106(2) 0.40824(9) 0.0595(7) Uani 1 1 d . . . . .
H13 H 0.4917 0.5724 0.3845 0.071 Uiso 1 1 calc R U . . .
C14 C 0.44158(15) 0.5667(2) 0.44405(10) 0.0696(8) Uani 1 1 d . . . . .
H14 H 0.4383 0.4982 0.4447 0.083 Uiso 1 1 calc R U . . .
C15 C 0.41425(13) 0.6186(2) 0.47862(9) 0.0596(7) Uani 1 1 d . . . . .
C16 C 0.37710(18) 0.5703(3) 0.51702(11) 0.1000(12) Uani 1 1 d . . . . .
H16A H 0.3278 0.5603 0.5093 0.150 Uiso 1 1 calc R U . . .
H16B H 0.3803 0.6114 0.5435 0.150 Uiso 1 1 calc R U . . .
H16C H 0.3991 0.5077 0.5232 0.150 Uiso 1 1 calc R U . . .
C17 C 0.34977(18) 1.0486(3) 0.28229(10) 0.0891(10) Uani 1 1 d . . . . .
H17A H 0.3797 1.1035 0.2745 0.134 Uiso 1 1 calc R U . . .
H17B H 0.3126 1.0704 0.3024 0.134 Uiso 1 1 calc R U . . .
H17C H 0.3289 1.0217 0.2552 0.134 Uiso 1 1 calc R U . . .
C18 C 0.39320(14) 0.9717(2) 0.30527(8) 0.0574(7) Uani 1 1 d . . . . .
C19 C 0.46396(14) 0.98508(19) 0.31295(8) 0.0556(7) Uani 1 1 d . . . . .
H19 H 0.4856 1.0433 0.3035 0.067 Uiso 1 1 calc R U . . .
C20 C 0.50391(13) 0.91551(19) 0.33415(7) 0.0515(6) Uani 1 1 d . . . . .
H20 H 0.5522 0.9270 0.3395 0.062 Uiso 1 1 calc R U . . .
C21 C 0.47410(11) 0.82962(18) 0.34761(7) 0.0458(6) Uani 1 1 d . . . . .
C22 C 0.45366(12) 0.76278(19) 0.44188(7) 0.0506(6) Uani 1 1 d . . . . .
H22 H 0.4582 0.8311 0.4418 0.061 Uiso 1 1 calc R U . . .
C23 C 0.42067(12) 0.7169(2) 0.47713(8) 0.0567(7) Uani 1 1 d . . . . .
H23 H 0.4021 0.7546 0.5008 0.068 Uiso 1 1 calc R U . . .
C24 C 0.61268(12) 0.75259(19) 0.31936(7) 0.0511(6) Uani 1 1 d . . . . .
H24 H 0.5831 0.7724 0.2956 0.061 Uiso 1 1 calc R U . . .
C25 C 0.68320(11) 0.73710(18) 0.31123(7) 0.0467(6) Uani 1 1 d . . . . .
H25 H 0.7019 0.7476 0.2823 0.056 Uiso 1 1 calc R U . . .
C26 C 0.72609(10) 0.70637(16) 0.34536(6) 0.0384(5) Uani 1 1 d . . . . .
C27 C 0.76666(11) 0.57854(17) 0.55610(7) 0.0421(5) Uani 1 1 d . . . . .
C28 C 0.76216(12) 0.67731(18) 0.56164(7) 0.0485(6) Uani 1 1 d . . . . .
H28 H 0.7855 0.7192 0.5415 0.058 Uiso 1 1 calc R U . . .
C29 C 0.72367(13) 0.71545(19) 0.59657(7) 0.0530(6) Uani 1 1 d . . . . .
H29 H 0.7208 0.7836 0.5998 0.064 Uiso 1 1 calc R U . . .
C30 C 0.68931(12) 0.65714(19) 0.62680(7) 0.0506(6) Uani 1 1 d . . . . .
C31 C 0.64988(16) 0.7005(2) 0.66557(8) 0.0744(9) Uani 1 1 d . . . . .
H31A H 0.6821 0.7109 0.6905 0.112 Uiso 1 1 calc R U . . .
H31B H 0.6125 0.6563 0.6748 0.112 Uiso 1 1 calc R U . . .
H31C H 0.6294 0.7624 0.6566 0.112 Uiso 1 1 calc R U . . .
C32 C 0.69319(13) 0.55884(19) 0.62039(8) 0.0545(6) Uani 1 1 d . . . . .
H32 H 0.6694 0.5170 0.6404 0.065 Uiso 1 1 calc R U . . .
C33 C 0.73097(12) 0.51957(18) 0.58544(7) 0.0499(6) Uani 1 1 d . . . . .
H33 H 0.7324 0.4515 0.5816 0.060 Uiso 1 1 calc R U . . .
C34 C 0.93080(11) 0.38316(17) 0.58696(7) 0.0440(5) Uani 1 1 d . . . . .
H34 H 0.9551 0.3862 0.6145 0.053 Uiso 1 1 calc R U . . .
C35 C 0.89027(11) 0.46110(17) 0.57410(7) 0.0428(5) Uani 1 1 d . . . . .
H35 H 0.8876 0.5167 0.5926 0.051 Uiso 1 1 calc R U . . .
C36 C 0.87200(12) 0.56953(18) 0.45301(7) 0.0455(6) Uani 1 1 d . . . . .
H36 H 0.9129 0.5418 0.4657 0.055 Uiso 1 1 calc R U . . .
C37 C 0.87413(11) 0.60407(17) 0.40990(7) 0.0436(5) Uani 1 1 d . . . . .
H37 H 0.9161 0.6000 0.3931 0.052 Uiso 1 1 calc R U . . .
C38 C 0.81484(10) 0.64464(16) 0.39127(6) 0.0380(5) Uani 1 1 d . . . . .
C39 C 0.80461(11) 0.68762(16) 0.34506(6) 0.0381(5) Uani 1 1 d . . . . .
C40 C 0.84567(10) 0.78122(17) 0.33830(7) 0.0403(5) Uani 1 1 d . . . . .
C41 C 0.84060(13) 0.86666(18) 0.36178(8) 0.0506(6) Uani 1 1 d . . . . .
H41 H 0.8089 0.8727 0.3860 0.061 Uiso 1 1 calc R U . . .
C42 C 0.88264(14) 0.9434(2) 0.34929(9) 0.0610(7) Uani 1 1 d . . . . .
H42 H 0.8798 1.0028 0.3651 0.073 Uiso 1 1 calc R U . . .
C43 C 0.92880(15) 0.9346(2) 0.31399(9) 0.0650(7) Uani 1 1 d . . . . .
H43 H 0.9577 0.9877 0.3061 0.078 Uiso 1 1 calc R U . . .
C44 C 0.93341(13) 0.8500(2) 0.29030(8) 0.0581(7) Uani 1 1 d . . . . .
H44 H 0.9652 0.8445 0.2661 0.070 Uiso 1 1 calc R U . . .
C45 C 0.89122(11) 0.77274(17) 0.30212(7) 0.0436(6) Uani 1 1 d . . . . .
C46 C 0.88211(11) 0.67707(17) 0.28242(7) 0.0428(5) Uani 1 1 d . . . . .
C47 C 0.83170(11) 0.62633(17) 0.30687(7) 0.0402(5) Uani 1 1 d . . . . .
C48 C 0.81287(13) 0.53386(18) 0.29523(8) 0.0524(6) Uani 1 1 d . . . . .
H48 H 0.7791 0.4994 0.3122 0.063 Uiso 1 1 calc R U . . .
C49 C 0.84400(14) 0.4918(2) 0.25835(8) 0.0617(7) Uani 1 1 d . . . . .
H49 H 0.8315 0.4278 0.2500 0.074 Uiso 1 1 calc R U . . .
C50 C 0.89292(14) 0.5418(2) 0.23362(8) 0.0624(7) Uani 1 1 d . . . . .
H50 H 0.9132 0.5120 0.2082 0.075 Uiso 1 1 calc R U . . .
C51 C 0.91283(12) 0.6338(2) 0.24515(7) 0.0549(7) Uani 1 1 d . . . . .
H51 H 0.9469 0.6675 0.2281 0.066 Uiso 1 1 calc R U . . .
C52 C 0.40291(12) 0.81555(19) 0.34003(7) 0.0502(6) Uani 1 1 d . . . . .
H52 H 0.3812 0.7570 0.3491 0.060 Uiso 1 1 calc R U . . .
C53 C 0.36385(13) 0.8862(2) 0.31940(8) 0.0576(7) Uani 1 1 d . . . . .
H53 H 0.3153 0.8756 0.3148 0.069 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'
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
C5 N1 C27 117.78(17) . . ?
C6 N1 C5 120.62(18) . . ?
C6 N1 C27 121.49(18) . . ?
C11 N2 C12 119.07(18) . . ?
C11 N2 C21 122.30(19) . . ?
C21 N2 C12 117.67(18) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.9(2) . . ?
C34 C2 C1 121.3(2) . . ?
C34 C2 C3 116.9(2) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.2(2) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 N1 121.3(2) . . ?
C35 C5 N1 120.0(2) . . ?
C35 C5 C4 118.6(2) . . ?
C7 C6 N1 120.66(19) . . ?
C7 C6 C36 119.08(19) . . ?
C36 C6 N1 120.25(19) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.66(19) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 130.87(19) . . ?
C7 C8 C38 120.77(19) . . ?
C38 C8 C9 108.22(17) . . ?
C10 C9 C8 130.83(18) . . ?
C10 C9 C26 120.99(19) . . ?
C26 C9 C8 108.17(17) . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.26(18) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 N2 119.79(19) . . ?
C24 C11 N2 120.91(19) . . ?
C24 C11 C10 119.27(19) . . ?
C13 C12 N2 120.8(2) . . ?
C13 C12 C22 118.8(2) . . ?
C22 C12 N2 120.4(2) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 122.1(3) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C16 121.8(3) . . ?
C14 C15 C23 117.7(2) . . ?
C23 C15 C16 120.5(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
C19 C18 C17 121.1(3) . . ?
C53 C18 C17 121.4(3) . . ?
C53 C18 C19 117.5(2) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.5(3) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 N2 122.9(2) . . ?
C20 C21 C52 118.4(2) . . ?
C52 C21 N2 118.7(2) . . ?
C12 C22 H22 120.0 . . ?
C12 C22 C23 119.9(2) . . ?
C23 C22 H22 120.0 . . ?
C15 C23 C22 121.5(2) . . ?
C15 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C11 C24 H24 119.4 . . ?
C25 C24 C11 121.2(2) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.6(2) . . ?
C26 C25 H25 120.2 . . ?
C9 C26 C39 111.10(17) . . ?
C25 C26 C9 119.58(19) . . ?
C25 C26 C39 129.32(18) . . ?
C28 C27 N1 121.7(2) . . ?
C28 C27 C33 118.5(2) . . ?
C33 C27 N1 119.7(2) . . ?
C27 C28 H28 119.9 . . ?
C27 C28 C29 120.1(2) . . ?
C29 C28 H28 119.9 . . ?
C28 C29 H29 119.1 . . ?
C30 C29 C28 121.8(2) . . ?
C30 C29 H29 119.1 . . ?
C29 C30 C31 120.8(2) . . ?
C32 C30 C29 117.4(2) . . ?
C32 C30 C31 121.8(2) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32 119.3 . . ?
C30 C32 C33 121.5(2) . . ?
C33 C32 H32 119.3 . . ?
C27 C33 C32 120.6(2) . . ?
C27 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C2 C34 H34 118.9 . . ?
C2 C34 C35 122.2(2) . . ?
C35 C34 H34 118.9 . . ?
C5 C35 H35 120.0 . . ?
C34 C35 C5 120.1(2) . . ?
C34 C35 H35 120.0 . . ?
C6 C36 H36 119.4 . . ?
C37 C36 C6 121.2(2) . . ?
C37 C36 H36 119.4 . . ?
C36 C37 H37 120.1 . . ?
C36 C37 C38 119.7(2) . . ?
C38 C37 H37 120.1 . . ?
C8 C38 C39 111.15(17) . . ?
C37 C38 C8 119.60(18) . . ?
C37 C38 C39 129.25(18) . . ?
C26 C39 C40 111.25(18) . . ?
C38 C39 C26 100.82(15) . . ?
C38 C39 C40 112.72(17) . . ?
C47 C39 C26 115.86(17) . . ?
C47 C39 C38 115.23(18) . . ?
C47 C39 C40 101.44(16) . . ?
C41 C40 C39 128.50(19) . . ?
C41 C40 C45 120.9(2) . . ?
C45 C40 C39 110.61(19) . . ?
C40 C41 H41 120.7 . . ?
C40 C41 C42 118.6(2) . . ?
C42 C41 H41 120.7 . . ?
C41 C42 H42 119.7 . . ?
C41 C42 C43 120.6(3) . . ?
C43 C42 H42 119.7 . . ?
C42 C43 H43 119.6 . . ?
C44 C43 C42 120.9(2) . . ?
C44 C43 H43 119.6 . . ?
C43 C44 H44 120.4 . . ?
C43 C44 C45 119.2(2) . . ?
C45 C44 H44 120.4 . . ?
C40 C45 C46 108.47(19) . . ?
C44 C45 C40 119.8(2) . . ?
C44 C45 C46 131.7(2) . . ?
C47 C46 C45 108.93(18) . . ?
C51 C46 C45 131.5(2) . . ?
C51 C46 C47 119.6(2) . . ?
C46 C47 C39 110.5(2) . . ?
C48 C47 C39 128.6(2) . . ?
C48 C47 C46 120.9(2) . . ?
C47 C48 H48 120.6 . . ?
C47 C48 C49 118.8(2) . . ?
C49 C48 H48 120.6 . . ?
C48 C49 H49 119.7 . . ?
C50 C49 C48 120.7(3) . . ?
C50 C49 H49 119.7 . . ?
C49 C50 H50 119.4 . . ?
C51 C50 C49 121.1(2) . . ?
C51 C50 H50 119.4 . . ?
C46 C51 H51 120.6 . . ?
C50 C51 C46 118.8(2) . . ?
C50 C51 H51 120.6 . . ?
C21 C52 H52 119.9 . . ?
C53 C52 C21 120.2(2) . . ?
C53 C52 H52 119.9 . . ?
C18 C53 C52 121.9(2) . . ?
C18 C53 H53 119.1 . . ?
C52 C53 H53 119.1 . . ?
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
N1 C5 1.425(3) . ?
N1 C6 1.418(3) . ?
N1 C27 1.426(3) . ?
N2 C11 1.414(3) . ?
N2 C12 1.429(3) . ?
N2 C21 1.424(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.505(3) . ?
C2 C3 1.383(3) . ?
C2 C34 1.380(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
C5 C35 1.384(3) . ?
C6 C7 1.393(3) . ?
C6 C36 1.399(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(3) . ?
C8 C9 1.473(3) . ?
C8 C38 1.399(3) . ?
C9 C10 1.385(3) . ?
C9 C26 1.400(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.398(3) . ?
C11 C24 1.393(3) . ?
C12 C13 1.368(3) . ?
C12 C22 1.383(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.366(4) . ?
C15 C16 1.510(4) . ?
C15 C23 1.367(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C18 1.516(4) . ?
C18 C19 1.384(4) . ?
C18 C53 1.377(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(3) . ?
C21 C52 1.393(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.386(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.379(3) . ?
C26 C39 1.523(3) . ?
C27 C28 1.380(3) . ?
C27 C33 1.381(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.385(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.381(3) . ?
C30 C31 1.511(3) . ?
C30 C32 1.376(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32 0.9500 . ?
C32 C33 1.385(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C34 C35 1.383(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C36 C37 1.380(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.383(3) . ?
C38 C39 1.522(3) . ?
C39 C40 1.528(3) . ?
C39 C47 1.517(3) . ?
C40 C41 1.380(3) . ?
C40 C45 1.397(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.384(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.384(4) . ?
C43 H43 0.9500 . ?
C43 C44 1.372(4) . ?
C44 H44 0.9500 . ?
C44 C45 1.386(3) . ?
C45 C46 1.461(3) . ?
C46 C47 1.400(3) . ?
C46 C51 1.398(3) . ?
C47 C48 1.375(3) . ?
C48 H48 0.9500 . ?
C48 C49 1.386(3) . ?
C49 H49 0.9500 . ?
C49 C50 1.380(4) . ?
C50 H50 0.9500 . ?
C50 C51 1.374(4) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C52 C53 1.377(3) . ?
C53 H53 0.9500 . ?
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
N1 C5 C35 C34 177.0(2) . . . . ?
N1 C6 C7 C8 -178.1(2) . . . . ?
N1 C6 C36 C37 178.4(2) . . . . ?
N1 C27 C28 C29 -176.2(2) . . . . ?
N1 C27 C33 C32 175.7(2) . . . . ?
N2 C11 C24 C25 179.8(2) . . . . ?
N2 C12 C13 C14 -179.4(2) . . . . ?
N2 C12 C22 C23 178.5(2) . . . . ?
N2 C21 C52 C53 178.8(2) . . . . ?
C1 C2 C3 C4 176.7(2) . . . . ?
C1 C2 C34 C35 -178.0(2) . . . . ?
C2 C3 C4 C5 1.7(4) . . . . ?
C2 C34 C35 C5 0.8(3) . . . . ?
C3 C2 C34 C35 0.4(3) . . . . ?
C3 C4 C5 N1 -178.2(2) . . . . ?
C3 C4 C5 C35 -0.4(3) . . . . ?
C4 C5 C35 C34 -0.9(3) . . . . ?
C5 N1 C6 C7 150.3(2) . . . . ?
C5 N1 C6 C36 -28.4(3) . . . . ?
C5 N1 C27 C28 133.2(2) . . . . ?
C5 N1 C27 C33 -44.2(3) . . . . ?
C6 N1 C5 C4 -47.7(3) . . . . ?
C6 N1 C5 C35 134.5(2) . . . . ?
C6 N1 C27 C28 -43.1(3) . . . . ?
C6 N1 C27 C33 139.5(2) . . . . ?
C6 C7 C8 C9 174.4(2) . . . . ?
C6 C7 C8 C38 -0.7(3) . . . . ?
C6 C36 C37 C38 0.1(4) . . . . ?
C7 C6 C36 C37 -0.4(4) . . . . ?
C7 C8 C9 C10 3.1(4) . . . . ?
C7 C8 C9 C26 -175.3(2) . . . . ?
C7 C8 C38 C37 0.4(3) . . . . ?
C7 C8 C38 C39 -179.3(2) . . . . ?
C8 C9 C10 C11 -176.4(2) . . . . ?
C8 C9 C26 C25 175.6(2) . . . . ?
C8 C9 C26 C39 -5.0(2) . . . . ?
C8 C38 C39 C26 -7.0(2) . . . . ?
C8 C38 C39 C40 111.7(2) . . . . ?
C8 C38 C39 C47 -132.5(2) . . . . ?
C9 C8 C38 C37 -175.7(2) . . . . ?
C9 C8 C38 C39 4.5(2) . . . . ?
C9 C10 C11 N2 178.6(2) . . . . ?
C9 C10 C11 C24 0.8(4) . . . . ?
C9 C26 C39 C38 7.2(2) . . . . ?
C9 C26 C39 C40 -112.6(2) . . . . ?
C9 C26 C39 C47 132.3(2) . . . . ?
C10 C9 C26 C25 -3.0(3) . . . . ?
C10 C9 C26 C39 176.4(2) . . . . ?
C10 C11 C24 C25 -2.4(4) . . . . ?
C11 N2 C12 C13 -64.9(3) . . . . ?
C11 N2 C12 C22 115.4(2) . . . . ?
C11 N2 C21 C20 -31.4(3) . . . . ?
C11 N2 C21 C52 150.1(2) . . . . ?
C11 C24 C25 C26 1.3(4) . . . . ?
C12 N2 C11 C10 -21.2(3) . . . . ?
C12 N2 C11 C24 156.5(2) . . . . ?
C12 N2 C21 C20 137.3(2) . . . . ?
C12 N2 C21 C52 -41.2(3) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C12 C22 C23 C15 1.1(4) . . . . ?
C13 C12 C22 C23 -1.2(3) . . . . ?
C13 C14 C15 C16 178.1(3) . . . . ?
C13 C14 C15 C23 -1.0(4) . . . . ?
C14 C15 C23 C22 0.0(4) . . . . ?
C16 C15 C23 C22 -179.1(2) . . . . ?
C17 C18 C19 C20 179.6(2) . . . . ?
C17 C18 C53 C52 179.6(2) . . . . ?
C18 C19 C20 C21 1.1(4) . . . . ?
C19 C18 C53 C52 -0.6(4) . . . . ?
C19 C20 C21 N2 -179.6(2) . . . . ?
C19 C20 C21 C52 -1.1(3) . . . . ?
C20 C21 C52 C53 0.2(3) . . . . ?
C21 N2 C11 C10 147.3(2) . . . . ?
C21 N2 C11 C24 -34.9(4) . . . . ?
C21 N2 C12 C13 126.0(2) . . . . ?
C21 N2 C12 C22 -53.7(3) . . . . ?
C21 C52 C53 C18 0.6(4) . . . . ?
C22 C12 C13 C14 0.3(4) . . . . ?
C24 C25 C26 C9 1.4(3) . . . . ?
C24 C25 C26 C39 -177.9(2) . . . . ?
C25 C26 C39 C38 -173.5(2) . . . . ?
C25 C26 C39 C40 66.8(3) . . . . ?
C25 C26 C39 C47 -48.4(3) . . . . ?
C26 C9 C10 C11 1.9(3) . . . . ?
C26 C39 C40 C41 52.5(3) . . . . ?
C26 C39 C40 C45 -125.41(18) . . . . ?
C26 C39 C47 C46 121.7(2) . . . . ?
C26 C39 C47 C48 -58.3(3) . . . . ?
C27 N1 C5 C4 136.0(2) . . . . ?
C27 N1 C5 C35 -41.8(3) . . . . ?
C27 N1 C6 C7 -33.5(3) . . . . ?
C27 N1 C6 C36 147.8(2) . . . . ?
C27 C28 C29 C30 0.4(4) . . . . ?
C28 C27 C33 C32 -1.8(3) . . . . ?
C28 C29 C30 C31 177.7(2) . . . . ?
C28 C29 C30 C32 -1.6(4) . . . . ?
C29 C30 C32 C33 1.0(4) . . . . ?
C30 C32 C33 C27 0.7(4) . . . . ?
C31 C30 C32 C33 -178.3(2) . . . . ?
C33 C27 C28 C29 1.3(3) . . . . ?
C34 C2 C3 C4 -1.7(3) . . . . ?
C36 C6 C7 C8 0.7(3) . . . . ?
C36 C37 C38 C8 -0.1(3) . . . . ?
C36 C37 C38 C39 179.6(2) . . . . ?
C37 C38 C39 C26 173.3(2) . . . . ?
C37 C38 C39 C40 -68.0(3) . . . . ?
C37 C38 C39 C47 47.8(3) . . . . ?
C38 C8 C9 C10 178.7(2) . . . . ?
C38 C8 C9 C26 0.3(2) . . . . ?
C38 C39 C40 C41 -59.9(3) . . . . ?
C38 C39 C40 C45 122.18(19) . . . . ?
C38 C39 C47 C46 -121.0(2) . . . . ?
C38 C39 C47 C48 59.0(3) . . . . ?
C39 C40 C41 C42 -179.0(2) . . . . ?
C39 C40 C45 C44 180.0(2) . . . . ?
C39 C40 C45 C46 1.6(2) . . . . ?
C39 C47 C48 C49 179.1(2) . . . . ?
C40 C39 C47 C46 1.1(2) . . . . ?
C40 C39 C47 C48 -178.9(2) . . . . ?
C40 C41 C42 C43 0.0(4) . . . . ?
C40 C45 C46 C47 -0.8(2) . . . . ?
C40 C45 C46 C51 177.5(2) . . . . ?
C41 C40 C45 C44 1.9(3) . . . . ?
C41 C40 C45 C46 -176.5(2) . . . . ?
C41 C42 C43 C44 0.7(4) . . . . ?
C42 C43 C44 C45 -0.1(4) . . . . ?
C43 C44 C45 C40 -1.2(3) . . . . ?
C43 C44 C45 C46 176.8(2) . . . . ?
C44 C45 C46 C47 -179.0(2) . . . . ?
C44 C45 C46 C51 -0.6(4) . . . . ?
C45 C40 C41 C42 -1.3(3) . . . . ?
C45 C46 C47 C39 -0.2(2) . . . . ?
C45 C46 C47 C48 179.8(2) . . . . ?
C45 C46 C51 C50 -178.6(2) . . . . ?
C46 C47 C48 C49 -0.9(3) . . . . ?
C47 C39 C40 C41 176.3(2) . . . . ?
C47 C39 C40 C45 -1.6(2) . . . . ?
C47 C46 C51 C50 -0.4(3) . . . . ?
C47 C48 C49 C50 -0.2(4) . . . . ?
C48 C49 C50 C51 0.9(4) . . . . ?
C49 C50 C51 C46 -0.6(4) . . . . ?
C51 C46 C47 C39 -178.83(19) . . . . ?
C51 C46 C47 C48 1.2(3) . . . . ?
C53 C18 C19 C20 -0.2(4) . . . . ?
