#------------------------------------------------------------------------------
#$Date: 2021-06-17 08:18:58 +0300 (Thu, 17 Jun 2021) $
#$Revision: 266525 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/23/2022393.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022393
loop_
_publ_author_name
'Shi, Linqi'
'Sun, Zipei'
'Tian, Jiajie'
'Huang, Yaodong'
'Meng, Jiben'
_publ_section_title
;
 Study of naphthopyran derivatives: structure and photochromic properties
 in solution and in polymer film
;
_journal_coeditor_code           CU3171
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229621005969
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C37 H26 O'
_chemical_formula_moiety         'C37 H26 O'
_chemical_formula_sum            'C37 H26 O'
_chemical_formula_weight         486.58
_chemical_name_systematic
;
3,3-Bis([1,1'-biphenyl]-4-yl)-3H-naphtho[2,1-b]pyran
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.941(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.960(4)
_cell_length_b                   23.880(8)
_cell_length_c                   20.385(7)
_cell_measurement_reflns_used    18178
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      1.3
_cell_volume                     5178(3)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2008)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2008)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2008)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            42284
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         1.337
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.9855
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.263
_refine_ls_extinction_coef       0.0050(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         9136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0853P)²+0.2747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1776
_refine_ls_wR_factor_ref         0.1920
_reflns_number_gt                6968
_reflns_number_total             9136
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cu3171sup1.cif
_cod_data_source_block           NP2
_cod_database_code               2022393
_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   0.985
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.58120(14) 0.14284(6) 0.19415(8) 0.0331(4) Uani d 1 . .
O O2 0.44537(14) 0.08748(6) 0.36916(8) 0.0330(4) Uani d 1 . .
C C1 0.6911(2) 0.11910(9) 0.18492(13) 0.0319(6) Uani d 1 . .
C C2 0.7764(2) 0.09771(9) 0.24269(13) 0.0347(6) Uani d 1 . .
H H2 0.758687 0.100460 0.285950 0.042 Uiso calc 1 . .
C C3 0.8853(2) 0.07292(10) 0.23558(13) 0.0369(6) Uani d 1 . .
H H3 0.942459 0.058120 0.274316 0.044 Uiso calc 1 . .
C C4 0.9144(2) 0.06888(9) 0.17176(13) 0.0348(6) Uani d 1 . .
C C5 1.0251(2) 0.04151(10) 0.16393(14) 0.0395(6) Uani d 1 . .
H H5 1.081959 0.025914 0.202245 0.047 Uiso calc 1 . .
C C6 1.0504(2) 0.03748(10) 0.10164(15) 0.0418(7) Uani d 1 . .
H H6 1.123824 0.018424 0.096786 0.050 Uiso calc 1 . .
C C7 0.9677(2) 0.06156(10) 0.04422(14) 0.0401(6) Uani d 1 . .
H H7 0.986533 0.058829 0.001203 0.048 Uiso calc 1 . .
C C8 0.8611(2) 0.08868(10) 0.05032(14) 0.0369(6) Uani d 1 . .
H H8 0.807322 0.105035 0.011471 0.044 Uiso calc 1 . .
C C9 0.8294(2) 0.09284(9) 0.11369(13) 0.0324(6) Uani d 1 . .
C C10 0.7160(2) 0.11860(9) 0.12179(13) 0.0316(6) Uani d 1 . .
C C11 0.6228(2) 0.14584(9) 0.06678(13) 0.0339(6) Uani d 1 . .
H H11 0.645967 0.158233 0.027178 0.041 Uiso calc 1 . .
C C12 0.5069(2) 0.15281(10) 0.07316(13) 0.0346(6) Uani d 1 . .
H H12 0.445440 0.170056 0.038087 0.041 Uiso calc 1 . .
C C13 0.4727(2) 0.13291(10) 0.13736(13) 0.0328(6) Uani d 1 . .
C C14 0.3639(2) 0.16729(9) 0.15071(13) 0.0337(6) Uani d 1 . .
C C15 0.3813(2) 0.21612(10) 0.18920(13) 0.0381(6) Uani d 1 . .
H H15 0.464053 0.228861 0.209198 0.046 Uiso calc 1 . .
C C16 0.2786(2) 0.24624(10) 0.19850(14) 0.0392(6) Uani d 1 . .
H H16 0.293063 0.278880 0.225922 0.047 Uiso calc 1 . .
C C17 0.1553(2) 0.23058(9) 0.16930(12) 0.0321(6) Uani d 1 . .
C C18 0.1387(2) 0.18126(10) 0.12990(13) 0.0369(6) Uani d 1 . .
H H18 0.056134 0.168812 0.109129 0.044 Uiso calc 1 . .
C C19 0.2408(2) 0.15089(10) 0.12115(13) 0.0357(6) Uani d 1 . .
H H19 0.226783 0.117935 0.094274 0.043 Uiso calc 1 . .
C C20 0.0443(2) 0.26195(10) 0.17944(13) 0.0362(6) Uani d 1 . .
C C21 0.0534(3) 0.31812(11) 0.19900(16) 0.0503(8) Uani d 1 . .
H H21 0.132501 0.336478 0.206502 0.060 Uiso calc 1 . .
C C22 -0.0499(3) 0.34757(12) 0.20769(17) 0.0569(8) Uani d 1 . .
H H22 -0.041493 0.386099 0.219534 0.068 Uiso calc 1 . .
C C23 -0.1659(3) 0.32159(11) 0.19932(16) 0.0505(7) Uani d 1 . .
H H23 -0.236453 0.341825 0.206173 0.061 Uiso calc 1 . .
C C24 -0.1770(2) 0.26619(11) 0.18098(16) 0.0519(8) Uani d 1 . .
H H24 -0.256080 0.247932 0.174208 0.062 Uiso calc 1 . .
C C25 -0.0730(2) 0.23693(11) 0.17236(15) 0.0475(7) Uani d 1 . .
H H25 -0.081970 0.198281 0.161182 0.057 Uiso calc 1 . .
C C26 0.4415(2) 0.07001(9) 0.13709(13) 0.0323(6) Uani d 1 . .
C C27 0.4271(2) 0.03619(9) 0.08019(13) 0.0348(6) Uani d 1 . .
H H27 0.445106 0.050846 0.040233 0.042 Uiso calc 1 . .
C C28 0.3863(2) -0.01900(10) 0.08127(13) 0.0362(6) Uani d 1 . .
H H28 0.378300 -0.041659 0.042158 0.043 Uiso calc 1 . .
C C29 0.3570(2) -0.04165(10) 0.13889(14) 0.0352(6) Uani d 1 . .
C C30 0.3760(2) -0.00794(10) 0.19670(13) 0.0354(6) Uani d 1 . .
H H30 0.359321 -0.022788 0.236902 0.042 Uiso calc 1 . .
C C31 0.4185(2) 0.04668(10) 0.19633(13) 0.0364(6) Uani d 1 . .
H H31 0.432205 0.068534 0.236381 0.044 Uiso calc 1 . .
C C32 0.3014(2) -0.09873(9) 0.13702(13) 0.0356(6) Uani d 1 . .
C C33 0.3494(2) -0.14383(10) 0.10855(14) 0.0420(6) Uani d 1 . .
H H33 0.423135 -0.139002 0.092396 0.050 Uiso calc 1 . .
C C34 0.2918(3) -0.19583(10) 0.10325(15) 0.0485(7) Uani d 1 . .
H H34 0.326928 -0.226242 0.083973 0.058 Uiso calc 1 . .
C C35 0.1838(3) -0.20389(12) 0.12575(15) 0.0520(8) Uani d 1 . .
H H35 0.142534 -0.239167 0.120686 0.062 Uiso calc 1 . .
C C36 0.1371(2) -0.15946(11) 0.15580(15) 0.0482(7) Uani d 1 . .
H H36 0.064276 -0.164746 0.172633 0.058 Uiso calc 1 . .
C C37 0.1942(2) -0.10768(10) 0.16176(14) 0.0422(7) Uani d 1 . .
H H37 0.160696 -0.077823 0.182780 0.051 Uiso calc 1 . .
C C38 0.3358(2) 0.11252(9) 0.37618(13) 0.0320(6) Uani d 1 . .
C C39 0.2475(2) 0.12765(9) 0.31588(13) 0.0344(6) Uani d 1 . .
H H39 0.265561 0.121401 0.273181 0.041 Uiso calc 1 . .
C C40 0.1357(2) 0.15138(9) 0.31977(13) 0.0356(6) Uani d 1 . .
H H40 0.075560 0.160727 0.279323 0.043 Uiso calc 1 . .
C C41 0.1081(2) 0.16225(9) 0.38293(14) 0.0350(6) Uani d 1 . .
C C42 -0.0060(2) 0.18830(10) 0.38759(15) 0.0427(7) Uani d 1 . .
H H42 -0.067235 0.197374 0.347441 0.051 Uiso calc 1 . .
C C43 -0.0290(2) 0.20053(11) 0.44914(16) 0.0507(8) Uani d 1 . .
H H43 -0.106339 0.217412 0.451426 0.061 Uiso calc 1 . .
C C44 0.0620(3) 0.18809(12) 0.50924(17) 0.0566(8) Uani d 1 . .
H H44 0.047148 0.198302 0.551684 0.068 Uiso calc 1 . .
C C45 0.1718(2) 0.16135(11) 0.50680(15) 0.0475(7) Uani d 1 . .
H H45 0.231043 0.152259 0.547687 0.057 Uiso calc 1 . .
C C46 0.1978(2) 0.14714(10) 0.44396(14) 0.0355(6) Uani d 1 . .
C C47 0.3124(2) 0.12026(9) 0.43931(13) 0.0339(6) Uani d 1 . .
C C48 0.4044(2) 0.09629(10) 0.49697(13) 0.0378(6) Uani d 1 . .
H H48 0.381971 0.089625 0.538493 0.045 Uiso calc 1 . .
C C49 0.5194(2) 0.08397(10) 0.49063(13) 0.0365(6) Uani d 1 . .
H H49 0.578293 0.066107 0.526337 0.044 Uiso calc 1 . .
C C50 0.5546(2) 0.09904(9) 0.42508(13) 0.0328(6) Uani d 1 . .
C C51 0.5890(2) 0.16104(9) 0.42082(13) 0.0320(6) Uani d 1 . .
C C52 0.6134(2) 0.19676(10) 0.47614(13) 0.0364(6) Uani d 1 . .
H H52 0.604024 0.183510 0.518595 0.044 Uiso calc 1 . .
C C53 0.6516(2) 0.25203(10) 0.47019(14) 0.0379(6) Uani d 1 . .
H H53 0.667609 0.275843 0.508653 0.045 Uiso calc 1 . .
C C54 0.6665(2) 0.27272(9) 0.40852(13) 0.0345(6) Uani d 1 . .
C C55 0.6406(2) 0.23667(9) 0.35294(13) 0.0349(6) Uani d 1 . .
H H55 0.649054 0.249905 0.310307 0.042 Uiso calc 1 . .
C C56 0.6026(2) 0.18177(9) 0.35892(13) 0.0344(6) Uani d 1 . .
H H56 0.585665 0.158028 0.320395 0.041 Uiso calc 1 . .
C C57 0.7078(2) 0.33169(10) 0.40165(14) 0.0371(6) Uani d 1 . .
C C58 0.6647(2) 0.37594(10) 0.43542(15) 0.0446(7) Uani d 1 . .
H H58 0.610359 0.368148 0.464202 0.054 Uiso calc 1 . .
C C59 0.6999(2) 0.43047(11) 0.42764(16) 0.0514(8) Uani d 1 . .
H H59 0.669836 0.459722 0.451160 0.062 Uiso calc 1 . .
C C60 0.7785(2) 0.44292(11) 0.38587(16) 0.0486(7) Uani d 1 . .
H H60 0.801962 0.480593 0.380244 0.058 Uiso calc 1 . .
C C61 0.8222(3) 0.40057(11) 0.35279(17) 0.0542(8) Uani d 1 . .
H H61 0.876574 0.408931 0.324188 0.065 Uiso calc 1 . .
C C62 0.7878(2) 0.34488(11) 0.36050(16) 0.0481(7) Uani d 1 . .
H H62 0.819537 0.315878 0.337346 0.058 Uiso calc 1 . .
C C63 0.6628(2) 0.06260(9) 0.41388(13) 0.0316(6) Uani d 1 . .
C C64 0.7845(2) 0.07480(10) 0.44997(13) 0.0379(6) Uani d 1 . .
H H64 0.797697 0.104297 0.482174 0.046 Uiso calc 1 . .
C C65 0.8873(2) 0.04494(10) 0.44010(13) 0.0375(6) Uani d 1 . .
H H65 0.969356 0.054375 0.465423 0.045 Uiso calc 1 . .
C C66 0.8714(2) 0.00124(9) 0.39344(13) 0.0339(6) Uani d 1 . .
C C67 0.7488(2) -0.01182(9) 0.35863(14) 0.0387(6) Uani d 1 . .
H H67 0.735501 -0.041885 0.327179 0.046 Uiso calc 1 . .
C C68 0.6449(2) 0.01795(9) 0.36859(13) 0.0357(6) Uani d 1 . .
H H68 0.562397 0.007774 0.344576 0.043 Uiso calc 1 . .
C C69 0.9827(2) -0.02845(9) 0.37990(13) 0.0363(6) Uani d 1 . .
C C70 1.0947(2) -0.00026(10) 0.38257(13) 0.0385(6) Uani d 1 . .
H H70 1.100636 0.038396 0.393889 0.046 Uiso calc 1 . .
C C71 1.1985(3) -0.02743(11) 0.36902(15) 0.0471(7) Uani d 1 . .
H H71 1.273895 -0.007353 0.370501 0.057 Uiso calc 1 . .
C C72 1.1907(3) -0.08365(13) 0.35348(17) 0.0586(9) Uani d 1 . .
H H72 1.260632 -0.102346 0.343567 0.070 Uiso calc 1 . .
C C73 1.0820(3) -0.11279(13) 0.35226(19) 0.0673(10) Uani d 1 . .
H H73 1.077965 -0.151756 0.342585 0.081 Uiso calc 1 . .
C C74 0.9776(3) -0.08555(11) 0.36512(16) 0.0526(8) Uani d 1 . .
H H74 0.902731 -0.105984 0.363800 0.063 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C13 . . 113.16(17) ?
C38 O2 C50 . . 113.93(17) ?
O1 C1 C2 . . 117.3(2) ?
C10 C1 O1 . . 120.3(2) ?
C10 C1 C2 . . 122.3(2) ?
C1 C2 H2 . . 120.4 ?
C3 C2 C1 . . 119.1(2) ?
C3 C2 H2 . . 120.4 ?
C2 C3 H3 . . 119.3 ?
C2 C3 C4 . . 121.4(2) ?
C4 C3 H3 . . 119.3 ?
C3 C4 C5 . . 121.5(2) ?
C3 C4 C9 . . 119.0(2) ?
C5 C4 C9 . . 119.5(2) ?
C4 C5 H5 . . 119.8 ?
C6 C5 C4 . . 120.5(2) ?
C6 C5 H5 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C5 C6 C7 . . 120.4(2) ?
C7 C6 H6 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C8 C7 C6 . . 120.5(3) ?
C8 C7 H7 . . 119.8 ?
C7 C8 H8 . . 119.4 ?
C7 C8 C9 . . 121.2(2) ?
C9 C8 H8 . . 119.4 ?
C8 C9 C4 . . 118.0(2) ?
C8 C9 C10 . . 123.0(2) ?
C10 C9 C4 . . 119.0(2) ?
C1 C10 C9 . . 119.0(2) ?
C1 C10 C11 . . 116.7(2) ?
C9 C10 C11 . . 124.3(2) ?
C10 C11 H11 . . 120.4 ?
C12 C11 C10 . . 119.2(2) ?
C12 C11 H11 . . 120.4 ?
C11 C12 H12 . . 120.4 ?
C11 C12 C13 . . 119.2(2) ?
C13 C12 H12 . . 120.4 ?
O1 C13 C12 . . 107.94(18) ?
O1 C13 C14 . . 107.01(19) ?
O1 C13 C26 . . 107.33(18) ?
C12 C13 C14 . . 110.51(19) ?
C12 C13 C26 . . 113.7(2) ?
C14 C13 C26 . . 110.06(18) ?
C15 C14 C13 . . 122.9(2) ?
C15 C14 C19 . . 117.8(2) ?
C19 C14 C13 . . 119.2(2) ?
C14 C15 H15 . . 119.8 ?
C16 C15 C14 . . 120.3(2) ?
C16 C15 H15 . . 119.8 ?
C15 C16 H16 . . 118.7 ?
C15 C16 C17 . . 122.6(2) ?
C17 C16 H16 . . 118.7 ?
C16 C17 C18 . . 116.5(2) ?
C16 C17 C20 . . 123.3(2) ?
C18 C17 C20 . . 120.2(2) ?
C17 C18 H18 . . 119.5 ?
C19 C18 C17 . . 121.0(2) ?
C19 C18 H18 . . 119.5 ?
C14 C19 H19 . . 119.1 ?
C18 C19 C14 . . 121.8(2) ?
C18 C19 H19 . . 119.1 ?
C21 C20 C17 . . 121.3(2) ?
C25 C20 C17 . . 122.4(2) ?
C25 C20 C21 . . 116.2(2) ?
C20 C21 H21 . . 119.3 ?
C22 C21 C20 . . 121.5(3) ?
C22 C21 H21 . . 119.3 ?
C21 C22 H22 . . 119.6 ?
C21 C22 C23 . . 120.8(3) ?
C23 C22 H22 . . 119.6 ?
C22 C23 H23 . . 120.6 ?
C24 C23 C22 . . 118.9(2) ?
C24 C23 H23 . . 120.6 ?
C23 C24 H24 . . 120.0 ?
C23 C24 C25 . . 120.0(3) ?
C25 C24 H24 . . 120.0 ?
C20 C25 H25 . . 118.7 ?
C24 C25 C20 . . 122.6(2) ?
C24 C25 H25 . . 118.7 ?
C27 C26 C13 . . 123.4(2) ?
C27 C26 C31 . . 118.5(2) ?
C31 C26 C13 . . 118.0(2) ?
C26 C27 H27 . . 119.7 ?
C26 C27 C28 . . 120.6(2) ?
C28 C27 H27 . . 119.7 ?
C27 C28 H28 . . 119.4 ?
C27 C28 C29 . . 121.2(2) ?
C29 C28 H28 . . 119.4 ?
C28 C29 C30 . . 117.8(2) ?
C28 C29 C32 . . 120.5(2) ?
C30 C29 C32 . . 121.6(2) ?
C29 C30 H30 . . 119.4 ?
C31 C30 C29 . . 121.2(2) ?
C31 C30 H30 . . 119.4 ?
C26 C31 H31 . . 119.7 ?
C30 C31 C26 . . 120.5(2) ?
C30 C31 H31 . . 119.7 ?
C33 C32 C29 . . 121.8(2) ?
C33 C32 C37 . . 117.9(2) ?
C37 C32 C29 . . 120.2(2) ?
C32 C33 H33 . . 119.4 ?
C34 C33 C32 . . 121.1(2) ?
C34 C33 H33 . . 119.4 ?
C33 C34 H34 . . 119.7 ?
C35 C34 C33 . . 120.6(3) ?
C35 C34 H34 . . 119.7 ?
C34 C35 H35 . . 120.7 ?
C34 C35 C36 . . 118.6(3) ?
C36 C35 H35 . . 120.7 ?
C35 C36 H36 . . 119.4 ?
C37 C36 C35 . . 121.2(3) ?
C37 C36 H36 . . 119.4 ?
C32 C37 H37 . . 119.8 ?
C36 C37 C32 . . 120.5(2) ?
C36 C37 H37 . . 119.8 ?
O2 C38 C39 . . 116.8(2) ?
O2 C38 C47 . . 121.0(2) ?
C47 C38 C39 . . 122.2(2) ?
C38 C39 H39 . . 120.3 ?
C40 C39 C38 . . 119.3(2) ?
C40 C39 H39 . . 120.3 ?
C39 C40 H40 . . 119.4 ?
C39 C40 C41 . . 121.3(2) ?
C41 C40 H40 . . 119.4 ?
C40 C41 C42 . . 121.7(2) ?
C40 C41 C46 . . 119.4(2) ?
C42 C41 C46 . . 118.9(2) ?
C41 C42 H42 . . 119.5 ?
C43 C42 C41 . . 120.9(3) ?
C43 C42 H42 . . 119.5 ?
C42 C43 H43 . . 119.9 ?
C42 C43 C44 . . 120.2(2) ?
C44 C43 H43 . . 119.9 ?
C43 C44 H44 . . 119.7 ?
C45 C44 C43 . . 120.5(3) ?
C45 C44 H44 . . 119.7 ?
C44 C45 H45 . . 119.6 ?
C44 C45 C46 . . 120.8(3) ?
C46 C45 H45 . . 119.6 ?
C41 C46 C47 . . 118.9(2) ?
C45 C46 C41 . . 118.6(2) ?
C45 C46 C47 . . 122.4(2) ?
C38 C47 C46 . . 118.9(2) ?
C38 C47 C48 . . 116.6(2) ?
C46 C47 C48 . . 124.4(2) ?
C47 C48 H48 . . 120.3 ?
C49 C48 C47 . . 119.5(2) ?
C49 C48 H48 . . 120.3 ?
C48 C49 H49 . . 120.7 ?
C48 C49 C50 . . 118.7(2) ?
C50 C49 H49 . . 120.7 ?
O2 C50 C49 . . 107.83(18) ?
O2 C50 C51 . . 107.65(18) ?
O2 C50 C63 . . 107.07(19) ?
C49 C50 C51 . . 113.32(19) ?
C49 C50 C63 . . 111.48(19) ?
C63 C50 C51 . . 109.23(18) ?
C52 C51 C50 . . 123.3(2) ?
C52 C51 C56 . . 118.3(2) ?
C56 C51 C50 . . 118.3(2) ?
C51 C52 H52 . . 119.6 ?
C51 C52 C53 . . 120.8(2) ?
C53 C52 H52 . . 119.6 ?
C52 C53 H53 . . 119.5 ?
C54 C53 C52 . . 120.9(2) ?
C54 C53 H53 . . 119.5 ?
C53 C54 C57 . . 121.4(2) ?
C55 C54 C53 . . 117.8(2) ?
C55 C54 C57 . . 120.8(2) ?
C54 C55 H55 . . 119.4 ?
C56 C55 C54 . . 121.1(2) ?
C56 C55 H55 . . 119.4 ?
C51 C56 H56 . . 119.6 ?
C55 C56 C51 . . 120.9(2) ?
C55 C56 H56 . . 119.6 ?
C58 C57 C54 . . 121.2(2) ?
C62 C57 C54 . . 121.3(2) ?
C62 C57 C58 . . 117.5(2) ?
C57 C58 H58 . . 119.4 ?
C59 C58 C57 . . 121.3(3) ?
C59 C58 H58 . . 119.4 ?
C58 C59 H59 . . 119.8 ?
C58 C59 C60 . . 120.5(3) ?
C60 C59 H59 . . 119.8 ?
C59 C60 H60 . . 120.3 ?
C61 C60 C59 . . 119.3(3) ?
C61 C60 H60 . . 120.3 ?
C60 C61 H61 . . 119.6 ?
C60 C61 C62 . . 120.8(3) ?
C62 C61 H61 . . 119.6 ?
C57 C62 C61 . . 120.6(2) ?
C57 C62 H62 . . 119.7 ?
C61 C62 H62 . . 119.7 ?
C64 C63 C50 . . 118.7(2) ?
C64 C63 C68 . . 118.4(2) ?
C68 C63 C50 . . 122.9(2) ?
C63 C64 H64 . . 119.2 ?
C65 C64 C63 . . 121.6(2) ?
C65 C64 H64 . . 119.2 ?
C64 C65 H65 . . 119.6 ?
C64 C65 C66 . . 120.7(2) ?
C66 C65 H65 . . 119.6 ?
C65 C66 C67 . . 117.5(2) ?
C65 C66 C69 . . 120.5(2) ?
C67 C66 C69 . . 122.0(2) ?
C66 C67 H67 . . 119.0 ?
C66 C67 C68 . . 122.1(2) ?
C68 C67 H67 . . 119.0 ?
C63 C68 C67 . . 119.7(2) ?
C63 C68 H68 . . 120.2 ?
C67 C68 H68 . . 120.2 ?
C70 C69 C66 . . 121.1(2) ?
C70 C69 C74 . . 118.1(2) ?
C74 C69 C66 . . 120.8(2) ?
C69 C70 H70 . . 119.3 ?
C69 C70 C71 . . 121.5(2) ?
C71 C70 H70 . . 119.3 ?
C70 C71 H71 . . 120.3 ?
C72 C71 C70 . . 119.4(3) ?
C72 C71 H71 . . 120.3 ?
C71 C72 H72 . . 119.9 ?
C73 C72 C71 . . 120.2(3) ?
C73 C72 H72 . . 119.9 ?
C72 C73 H73 . . 119.8 ?
C72 C73 C74 . . 120.5(3) ?
C74 C73 H73 . . 119.8 ?
C69 C74 H74 . . 119.8 ?
C73 C74 C69 . . 120.3(3) ?
C73 C74 H74 . . 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.384(3) ?
O1 C13 . 1.465(3) ?
O2 C38 . 1.379(3) ?
O2 C50 . 1.466(3) ?
C1 C2 . 1.412(3) ?
C1 C10 . 1.379(3) ?
C2 H2 . 0.9500 ?
C2 C3 . 1.371(3) ?
C3 H3 . 0.9500 ?
C3 C4 . 1.415(3) ?
C4 C5 . 1.421(3) ?
C4 C9 . 1.437(3) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.367(4) ?
C6 H6 . 0.9500 ?
C6 C7 . 1.418(4) ?
C7 H7 . 0.9500 ?
C7 C8 . 1.368(3) ?
C8 H8 . 0.9500 ?
C8 C9 . 1.419(3) ?
C9 C10 . 1.432(3) ?
C10 C11 . 1.474(3) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.318(3) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.522(3) ?
C13 C14 . 1.526(3) ?
C13 C26 . 1.540(3) ?
C14 C15 . 1.393(3) ?
C14 C19 . 1.395(3) ?
C15 H15 . 0.9500 ?
C15 C16 . 1.387(3) ?
C16 H16 . 0.9500 ?
C16 C17 . 1.390(3) ?
C17 C18 . 1.412(3) ?
C17 C20 . 1.485(3) ?
C18 H18 . 0.9500 ?
C18 C19 . 1.380(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.396(3) ?
C20 C25 . 1.394(3) ?
C21 H21 . 0.9500 ?
C21 C22 . 1.380(4) ?
C22 H22 . 0.9500 ?
C22 C23 . 1.388(4) ?
C23 H23 . 0.9500 ?
C23 C24 . 1.372(4) ?
C24 H24 . 0.9500 ?
C24 C25 . 1.384(3) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.391(3) ?
C26 C31 . 1.407(3) ?
C27 H27 . 0.9500 ?
C27 C28 . 1.393(3) ?
C28 H28 . 0.9500 ?
C28 C29 . 1.399(3) ?
C29 C30 . 1.401(3) ?
C29 C32 . 1.490(3) ?
C30 H30 . 0.9500 ?
C30 C31 . 1.386(3) ?
C31 H31 . 0.9500 ?
C32 C33 . 1.386(3) ?
C32 C37 . 1.402(3) ?
C33 H33 . 0.9500 ?
C33 C34 . 1.385(3) ?
C34 H34 . 0.9500 ?
C34 C35 . 1.382(4) ?
C35 H35 . 0.9500 ?
C35 C36 . 1.384(4) ?
C36 H36 . 0.9500 ?
C36 C37 . 1.378(3) ?
C37 H37 . 0.9500 ?
C38 C39 . 1.416(3) ?
C38 C47 . 1.384(3) ?
C39 H39 . 0.9500 ?
C39 C40 . 1.369(3) ?
C40 H40 . 0.9500 ?
C40 C41 . 1.416(3) ?
C41 C42 . 1.420(3) ?
C41 C46 . 1.434(4) ?
C42 H42 . 0.9500 ?
C42 C43 . 1.370(4) ?
C43 H43 . 0.9500 ?
C43 C44 . 1.412(4) ?
C44 H44 . 0.9500 ?
C44 C45 . 1.374(3) ?
C45 H45 . 0.9500 ?
C45 C46 . 1.419(4) ?
C46 C47 . 1.434(3) ?
C47 C48 . 1.468(3) ?
C48 H48 . 0.9500 ?
C48 C49 . 1.330(3) ?
C49 H49 . 0.9500 ?
C49 C50 . 1.521(3) ?
C50 C51 . 1.535(3) ?
C50 C63 . 1.532(3) ?
C51 C52 . 1.388(3) ?
C51 C56 . 1.396(3) ?
C52 H52 . 0.9500 ?
C52 C53 . 1.399(3) ?
C53 H53 . 0.9500 ?
C53 C54 . 1.397(3) ?
C54 C55 . 1.397(3) ?
C54 C57 . 1.496(3) ?
C55 H55 . 0.9500 ?
C55 C56 . 1.390(3) ?
C56 H56 . 0.9500 ?
C57 C58 . 1.403(3) ?
C57 C62 . 1.388(4) ?
C58 H58 . 0.9500 ?
C58 C59 . 1.378(4) ?
C59 H59 . 0.9500 ?
C59 C60 . 1.382(4) ?
C60 H60 . 0.9500 ?
C60 C61 . 1.365(4) ?
C61 H61 . 0.9500 ?
C61 C62 . 1.401(4) ?
C62 H62 . 0.9500 ?
C63 C64 . 1.390(3) ?
C63 C68 . 1.393(3) ?
C64 H64 . 0.9500 ?
C64 C65 . 1.388(3) ?
C65 H65 . 0.9500 ?
C65 C66 . 1.394(3) ?
C66 C67 . 1.396(3) ?
C66 C69 . 1.493(3) ?
C67 H67 . 0.9500 ?
C67 C68 . 1.398(3) ?
C68 H68 . 0.9500 ?
C69 C70 . 1.389(3) ?
C69 C74 . 1.395(3) ?
C70 H70 . 0.9500 ?
C70 C71 . 1.394(3) ?
C71 H71 . 0.9500 ?
C71 C72 . 1.377(4) ?
C72 H72 . 0.9500 ?
C72 C73 . 1.374(4) ?
C73 H73 . 0.9500 ?
C73 C74 . 1.395(4) ?
C74 H74 . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 178.80(19) ?
O1 C1 C10 C9 . . . . -178.90(18) ?
O1 C1 C10 C11 . . . . 1.9(3) ?
O1 C13 C14 C15 . . . . 27.0(3) ?
O1 C13 C14 C19 . . . . -155.7(2) ?
O1 C13 C26 C27 . . . . -128.6(2) ?
O1 C13 C26 C31 . . . . 55.8(3) ?
O2 C38 C39 C40 . . . . 178.40(19) ?
O2 C38 C47 C46 . . . . 179.22(19) ?
O2 C38 C47 C48 . . . . -5.1(3) ?
O2 C50 C51 C52 . . . . 132.9(2) ?
O2 C50 C51 C56 . . . . -50.4(3) ?
O2 C50 C63 C64 . . . . 164.8(2) ?
O2 C50 C63 C68 . . . . -14.6(3) ?
C1 O1 C13 C12 . . . . -54.1(2) ?
C1 O1 C13 C14 . . . . -173.09(17) ?
C1 O1 C13 C26 . . . . 68.8(2) ?
C1 C2 C3 C4 . . . . 0.7(3) ?
C1 C10 C11 C12 . . . . -21.5(3) ?
C2 C1 C10 C9 . . . . 3.4(3) ?
C2 C1 C10 C11 . . . . -175.8(2) ?
C2 C3 C4 C5 . . . . -177.8(2) ?
C2 C3 C4 C9 . . . . 1.9(3) ?
C3 C4 C5 C6 . . . . 179.1(2) ?
C3 C4 C9 C8 . . . . 179.5(2) ?
C3 C4 C9 C10 . . . . -1.8(3) ?
C4 C5 C6 C7 . . . . 1.3(4) ?
C4 C9 C10 C1 . . . . -0.7(3) ?
C4 C9 C10 C11 . . . . 178.4(2) ?
C5 C4 C9 C8 . . . . -0.8(3) ?
C5 C4 C9 C10 . . . . 177.8(2) ?
C5 C6 C7 C8 . . . . -0.6(4) ?
C6 C7 C8 C9 . . . . -0.9(4) ?
C7 C8 C9 C4 . . . . 1.5(3) ?
C7 C8 C9 C10 . . . . -177.1(2) ?
C8 C9 C10 C1 . . . . 177.9(2) ?
C8 C9 C10 C11 . . . . -3.0(4) ?
C9 C4 C5 C6 . . . . -0.6(3) ?
C9 C10 C11 C12 . . . . 159.3(2) ?
C10 C1 C2 C3 . . . . -3.4(3) ?
C10 C11 C12 C13 . . . . 0.4(3) ?
C11 C12 C13 O1 . . . . 36.2(3) ?
C11 C12 C13 C14 . . . . 152.9(2) ?
C11 C12 C13 C26 . . . . -82.7(3) ?
C12 C13 C14 C15 . . . . -90.3(3) ?
C12 C13 C14 C19 . . . . 87.1(3) ?
C12 C13 C26 C27 . . . . -9.3(3) ?
C12 C13 C26 C31 . . . . 175.1(2) ?
C13 O1 C1 C2 . . . . -145.0(2) ?
C13 O1 C1 C10 . . . . 37.2(3) ?
C13 C14 C15 C16 . . . . 178.7(2) ?
C13 C14 C19 C18 . . . . -178.2(2) ?
C13 C26 C27 C28 . . . . -173.4(2) ?
C13 C26 C31 C30 . . . . 172.6(2) ?
C14 C13 C26 C27 . . . . 115.3(2) ?
C14 C13 C26 C31 . . . . -60.4(3) ?
C14 C15 C16 C17 . . . . -1.6(4) ?
C15 C14 C19 C18 . . . . -0.7(4) ?
C15 C16 C17 C18 . . . . 1.0(4) ?
C15 C16 C17 C20 . . . . 179.2(2) ?
C16 C17 C18 C19 . . . . -0.3(4) ?
C16 C17 C20 C21 . . . . 22.1(4) ?
C16 C17 C20 C25 . . . . -155.7(3) ?
C17 C18 C19 C14 . . . . 0.2(4) ?
C17 C20 C21 C22 . . . . 179.2(3) ?
C17 C20 C25 C24 . . . . -179.2(3) ?
C18 C17 C20 C21 . . . . -159.8(3) ?
C18 C17 C20 C25 . . . . 22.5(4) ?
C19 C14 C15 C16 . . . . 1.4(4) ?
C20 C17 C18 C19 . . . . -178.6(2) ?
C20 C21 C22 C23 . . . . 2.1(5) ?
C21 C20 C25 C24 . . . . 2.9(4) ?
C21 C22 C23 C24 . . . . -1.2(5) ?
C22 C23 C24 C25 . . . . 1.2(5) ?
C23 C24 C25 C20 . . . . -2.1(5) ?
C25 C20 C21 C22 . . . . -2.9(4) ?
C26 C13 C14 C15 . . . . 143.3(2) ?
C26 C13 C14 C19 . . . . -39.3(3) ?
C26 C27 C28 C29 . . . . 1.0(4) ?
C27 C26 C31 C30 . . . . -3.3(3) ?
C27 C28 C29 C30 . . . . -3.1(3) ?
C27 C28 C29 C32 . . . . 173.8(2) ?
C28 C29 C30 C31 . . . . 2.0(3) ?
C28 C29 C32 C33 . . . . 46.3(3) ?
C28 C29 C32 C37 . . . . -130.9(3) ?
C29 C30 C31 C26 . . . . 1.2(4) ?
C29 C32 C33 C34 . . . . -175.8(2) ?
C29 C32 C37 C36 . . . . 175.4(2) ?
C30 C29 C32 C33 . . . . -136.9(3) ?
C30 C29 C32 C37 . . . . 45.9(3) ?
C31 C26 C27 C28 . . . . 2.2(3) ?
C32 C29 C30 C31 . . . . -174.9(2) ?
C32 C33 C34 C35 . . . . 0.6(4) ?
C33 C32 C37 C36 . . . . -1.9(4) ?
C33 C34 C35 C36 . . . . -2.3(4) ?
C34 C35 C36 C37 . . . . 1.8(4) ?
C35 C36 C37 C32 . . . . 0.3(4) ?
C37 C32 C33 C34 . . . . 1.4(4) ?
C38 O2 C50 C49 . . . . 52.9(2) ?
C38 O2 C50 C51 . . . . -69.6(2) ?
C38 O2 C50 C63 . . . . 173.02(17) ?
C38 C39 C40 C41 . . . . 1.5(3) ?
C38 C47 C48 C49 . . . . 19.9(3) ?
C39 C38 C47 C46 . . . . -3.3(3) ?
C39 C38 C47 C48 . . . . 172.4(2) ?
C39 C40 C41 C42 . . . . 178.2(2) ?
C39 C40 C41 C46 . . . . -1.2(3) ?
C40 C41 C42 C43 . . . . -177.4(2) ?
C40 C41 C46 C45 . . . . 176.3(2) ?
C40 C41 C46 C47 . . . . -1.3(3) ?
C41 C42 C43 C44 . . . . 1.0(4) ?
C41 C46 C47 C38 . . . . 3.5(3) ?
C41 C46 C47 C48 . . . . -171.9(2) ?
C42 C41 C46 C45 . . . . -3.1(3) ?
C42 C41 C46 C47 . . . . 179.3(2) ?
C42 C43 C44 C45 . . . . -3.0(4) ?
C43 C44 C45 C46 . . . . 1.9(4) ?
C44 C45 C46 C41 . . . . 1.2(4) ?
C44 C45 C46 C47 . . . . 178.7(2) ?
C45 C46 C47 C38 . . . . -174.0(2) ?
C45 C46 C47 C48 . . . . 10.6(4) ?
C46 C41 C42 C43 . . . . 2.0(4) ?
C46 C47 C48 C49 . . . . -164.7(2) ?
C47 C38 C39 C40 . . . . 0.8(3) ?
C47 C48 C49 C50 . . . . 4.3(4) ?
C48 C49 C50 O2 . . . . -39.5(3) ?
C48 C49 C50 C51 . . . . 79.5(3) ?
C48 C49 C50 C63 . . . . -156.7(2) ?
C49 C50 C51 C52 . . . . 13.8(3) ?
C49 C50 C51 C56 . . . . -169.6(2) ?
C49 C50 C63 C64 . . . . -77.4(3) ?
C49 C50 C63 C68 . . . . 103.1(3) ?
C50 O2 C38 C39 . . . . 149.5(2) ?
C50 O2 C38 C47 . . . . -32.9(3) ?
C50 C51 C52 C53 . . . . 176.2(2) ?
C50 C51 C56 C55 . . . . -176.3(2) ?
C50 C63 C64 C65 . . . . -177.2(2) ?
C50 C63 C68 C67 . . . . 177.0(2) ?
C51 C50 C63 C64 . . . . 48.5(3) ?
C51 C50 C63 C68 . . . . -130.9(2) ?
C51 C52 C53 C54 . . . . -0.2(3) ?
C52 C51 C56 C55 . . . . 0.5(3) ?
C52 C53 C54 C55 . . . . 0.8(3) ?
C52 C53 C54 C57 . . . . -179.8(2) ?
C53 C54 C55 C56 . . . . -0.8(3) ?
C53 C54 C57 C58 . . . . -38.5(3) ?
C53 C54 C57 C62 . . . . 142.9(3) ?
C54 C55 C56 C51 . . . . 0.1(3) ?
C54 C57 C58 C59 . . . . -178.2(2) ?
C54 C57 C62 C61 . . . . 177.8(3) ?
C55 C54 C57 C58 . . . . 140.9(3) ?
C55 C54 C57 C62 . . . . -37.7(4) ?
C56 C51 C52 C53 . . . . -0.5(3) ?
C57 C54 C55 C56 . . . . 179.8(2) ?
C57 C58 C59 C60 . . . . 0.2(4) ?
C58 C57 C62 C61 . . . . -0.8(4) ?
C58 C59 C60 C61 . . . . -0.6(5) ?
C59 C60 C61 C62 . . . . 0.3(5) ?
C60 C61 C62 C57 . . . . 0.5(5) ?
C62 C57 C58 C59 . . . . 0.5(4) ?
C63 C50 C51 C52 . . . . -111.2(2) ?
C63 C50 C51 C56 . . . . 65.5(3) ?
C63 C64 C65 C66 . . . . -0.3(4) ?
C64 C63 C68 C67 . . . . -2.5(4) ?
C64 C65 C66 C67 . . . . -1.4(4) ?
C64 C65 C66 C69 . . . . 176.2(2) ?
C65 C66 C67 C68 . . . . 1.1(4) ?
C65 C66 C69 C70 . . . . -33.4(4) ?
C65 C66 C69 C74 . . . . 145.6(3) ?
C66 C67 C68 C63 . . . . 0.8(4) ?
C66 C69 C70 C71 . . . . -179.0(2) ?
C66 C69 C74 C73 . . . . 179.7(3) ?
C67 C66 C69 C70 . . . . 144.1(3) ?
C67 C66 C69 C74 . . . . -36.8(4) ?
C68 C63 C64 C65 . . . . 2.2(4) ?
C69 C66 C67 C68 . . . . -176.5(2) ?
C69 C70 C71 C72 . . . . -0.9(4) ?
C70 C69 C74 C73 . . . . -1.2(4) ?
C70 C71 C72 C73 . . . . -0.9(5) ?
C71 C72 C73 C74 . . . . 1.5(5) ?
C72 C73 C74 C69 . . . . -0.5(5) ?
C74 C69 C70 C71 . . . . 1.9(4) ?
