#------------------------------------------------------------------------------
#$Date: 2022-02-04 03:42:24 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272538 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/63/1566302.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_1566302
loop_
_publ_author_name
'Hirao, Yasukazu'
'Ihara, Keiji'
'Ishibashi, Yukihide'
'Tiu, Elisha Gabrielle'
'Asahi, Tsuyoshi'
'Kubo, Takashi'
_publ_section_title
;
 Mechanism and Kinetics of Fluorescence Quenching of Fluorene-Endcapped
 Butatriene: A Microspectroscopic Study of the Discrete State Constructed
 in Microcrystals
;
_journal_issue                   2
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              1196
_journal_page_last               1203
_journal_paper_doi               10.1021/acs.jpcc.1c09163
_journal_volume                  126
_journal_year                    2022
_chemical_formula_sum            'C44 H48'
_chemical_formula_weight         576.82
_chemical_name_systematic
;
1,2-bis(3,6-di-tert-butyl-9H-fluoren-9-ylidene)ethene
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 98.646(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9081(10)
_cell_length_b                   10.1431(6)
_cell_length_c                   23.4731(17)
_cell_measurement_reflns_used    23934
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      3.08
_cell_volume                     3744.5(4)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_computing_publication_material
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Rigaku VariMax RAPID FR-E
;
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            36166
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.079
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Empirical Absorption Correction   March 2001 T. Higashi
    Rigaku Corporation, Tokyo, Japan
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.023
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         8588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1283
_refine_ls_R_factor_gt           0.0762
_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)+(0.0688P)²+1.0156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5417
_reflns_number_total             8588
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp1c09163_si_002.cif
_cod_data_source_block           3b
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1566302
_shelx_shelxl_version_number     2018/1
_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   0.983
_shelx_estimated_absorpt_t_max   0.989
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_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 0.15806(14) 0.0918(2) 0.04911(10) 0.0427(5) Uani 1 1 d . . . . .
C2 C 0.18693(14) 0.0128(2) 0.01661(10) 0.0413(5) Uani 1 1 d . . . . .
C3 C 0.12728(13) 0.1731(2) 0.08636(9) 0.0380(5) Uani 1 1 d . . . . .
C4 C 0.21860(14) -0.0761(2) -0.01714(9) 0.0405(5) Uani 1 1 d . . . . .
C5 C 0.15984(13) 0.3030(2) 0.10584(9) 0.0365(5) Uani 1 1 d . . . . .
C6 C 0.22542(14) 0.3780(2) 0.09075(10) 0.0457(6) Uani 1 1 d . . . . .
H1 H 0.257222 0.347741 0.062177 0.055 Uiso 1 1 calc R U . . .
C7 C 0.24430(14) 0.4982(2) 0.11781(10) 0.0481(6) Uani 1 1 d . . . . .
H2 H 0.288934 0.550155 0.106856 0.058 Uiso 1 1 calc R U . . .
C8 C 0.19997(13) 0.5456(2) 0.16062(9) 0.0394(5) Uani 1 1 d . . . . .
C9 C 0.13394(12) 0.46862(19) 0.17544(9) 0.0358(5) Uani 1 1 d . . . . .
H3 H 0.102609 0.498894 0.204280 0.043 Uiso 1 1 calc R U . . .
C10 C 0.11336(12) 0.34890(19) 0.14877(8) 0.0336(4) Uani 1 1 d . . . . .
C11 C 0.04972(12) 0.24855(19) 0.15676(8) 0.0331(4) Uani 1 1 d . . . . .
C12 C -0.00968(13) 0.2412(2) 0.19429(9) 0.0388(5) Uani 1 1 d . . . . .
H4 H -0.014159 0.311157 0.220593 0.047 Uiso 1 1 calc R U . . .
C13 C -0.06312(13) 0.1312(2) 0.19361(10) 0.0422(5) Uani 1 1 d . . . . .
C14 C -0.05585(15) 0.0319(2) 0.15373(11) 0.0499(6) Uani 1 1 d . . . . .
H5 H -0.092904 -0.041928 0.152122 0.060 Uiso 1 1 calc R U . . .
C15 C 0.00342(14) 0.0370(2) 0.11642(10) 0.0468(6) Uani 1 1 d . . . . .
H6 H 0.007239 -0.032631 0.089876 0.056 Uiso 1 1 calc R U . . .
C16 C 0.05705(13) 0.1444(2) 0.11810(9) 0.0371(5) Uani 1 1 d . . . . .
C17 C 0.18420(13) -0.2090(2) -0.03187(9) 0.0374(5) Uani 1 1 d . . . . .
C18 C 0.11373(14) -0.2728(2) -0.01807(10) 0.0431(5) Uani 1 1 d . . . . .
H7 H 0.077443 -0.230444 0.004929 0.052 Uiso 1 1 calc R U . . .
C19 C 0.09644(13) -0.4002(2) -0.03831(9) 0.0421(5) Uani 1 1 d . . . . .
H8 H 0.048088 -0.444622 -0.028420 0.050 Uiso 1 1 calc R U . . .
C20 C 0.14775(13) -0.46489(19) -0.07267(9) 0.0354(5) Uani 1 1 d . . . . .
C21 C 0.21816(13) -0.39816(19) -0.08672(9) 0.0363(5) Uani 1 1 d . . . . .
H9 H 0.253898 -0.439625 -0.110347 0.044 Uiso 1 1 calc R U . . .
C22 C 0.23650(13) -0.27155(19) -0.06648(9) 0.0365(5) Uani 1 1 d . . . . .
C23 C 0.30642(13) -0.18175(19) -0.07413(9) 0.0382(5) Uani 1 1 d . . . . .
C24 C 0.37581(13) -0.1978(2) -0.10255(9) 0.0413(5) Uani 1 1 d . . . . .
H10 H 0.382831 -0.278045 -0.122144 0.050 Uiso 1 1 calc R U . . .
C25 C 0.43556(13) -0.0974(2) -0.10273(9) 0.0414(5) Uani 1 1 d . . . . .
C26 C 0.42283(15) 0.0185(2) -0.07349(11) 0.0493(6) Uani 1 1 d . . . . .
H11 H 0.462975 0.087873 -0.073375 0.059 Uiso 1 1 calc R U . . .
C27 C 0.35387(15) 0.0369(2) -0.04449(11) 0.0484(6) Uani 1 1 d . . . . .
H12 H 0.347100 0.117236 -0.024864 0.058 Uiso 1 1 calc R U . . .
C28 C 0.29519(13) -0.0637(2) -0.04467(9) 0.0398(5) Uani 1 1 d . . . . .
C29 C 0.22303(15) 0.6786(2) 0.18988(11) 0.0512(6) Uani 1 1 d . . . . .
C30 C 0.2984(4) 0.7438(6) 0.1760(3) 0.079(2) Uani 0.601(7) 1 d . . P A 1
H13 H 0.347924 0.686598 0.186663 0.118 Uiso 0.601(7) 1 calc R U P A 1
H14 H 0.306981 0.826877 0.197365 0.118 Uiso 0.601(7) 1 calc R U P A 1
H15 H 0.291291 0.761909 0.134534 0.118 Uiso 0.601(7) 1 calc R U P A 1
C31 C 0.2367(4) 0.6557(6) 0.2580(2) 0.0660(16) Uani 0.601(7) 1 d . . P A 1
H16 H 0.285957 0.598234 0.268993 0.099 Uiso 0.601(7) 1 calc R U P A 1
H17 H 0.185867 0.614079 0.268992 0.099 Uiso 0.601(7) 1 calc R U P A 1
H18 H 0.246507 0.740637 0.277741 0.099 Uiso 0.601(7) 1 calc R U P A 1
C32 C 0.1441(3) 0.7713(4) 0.1775(3) 0.075(2) Uani 0.601(7) 1 d . . P A 1
H19 H 0.157465 0.856436 0.196496 0.112 Uiso 0.601(7) 1 calc R U P A 1
H20 H 0.095884 0.730941 0.192466 0.112 Uiso 0.601(7) 1 calc R U P A 1
H21 H 0.129476 0.784746 0.135879 0.112 Uiso 0.601(7) 1 calc R U P A 1
C33 C 0.3230(5) 0.6787(10) 0.2066(5) 0.080(3) Uani 0.399(7) 1 d . . P A 2
H22 H 0.341319 0.761880 0.225765 0.119 Uiso 0.399(7) 1 calc R U P A 2
H23 H 0.349321 0.669229 0.171658 0.119 Uiso 0.399(7) 1 calc R U P A 2
H24 H 0.340324 0.604958 0.232713 0.119 Uiso 0.399(7) 1 calc R U P A 2
C34 C 0.1819(7) 0.7108(10) 0.2367(5) 0.089(4) Uani 0.399(7) 1 d . . P A 2
H25 H 0.120481 0.715952 0.223924 0.134 Uiso 0.399(7) 1 calc R U P A 2
H26 H 0.202715 0.796130 0.252600 0.134 Uiso 0.399(7) 1 calc R U P A 2
H27 H 0.193816 0.642745 0.266511 0.134 Uiso 0.399(7) 1 calc R U P A 2
C35 C 0.2065(6) 0.7881(6) 0.1396(3) 0.077(3) Uani 0.399(7) 1 d . . P A 2
H28 H 0.145885 0.789742 0.123705 0.115 Uiso 0.399(7) 1 calc R U P A 2
H29 H 0.239752 0.766187 0.108998 0.115 Uiso 0.399(7) 1 calc R U P A 2
H30 H 0.223719 0.874943 0.155575 0.115 Uiso 0.399(7) 1 calc R U P A 2
C36 C -0.12501(15) 0.1204(2) 0.23785(11) 0.0501(6) Uani 1 1 d . . . . .
C37 C -0.1875(3) 0.0034(4) 0.2239(2) 0.0766(15) Uani 0.788(7) 1 d . . P B 1
H31 H -0.155512 -0.079530 0.226562 0.115 Uiso 0.788(7) 1 calc R U P B 1
H32 H -0.218521 0.013587 0.184833 0.115 Uiso 0.788(7) 1 calc R U P B 1
H33 H -0.227888 0.002188 0.251587 0.115 Uiso 0.788(7) 1 calc R U P B 1
C38 C -0.1790(2) 0.2449(3) 0.23680(19) 0.0606(13) Uani 0.788(7) 1 d . . P B 1
H34 H -0.217047 0.237810 0.265816 0.091 Uiso 0.788(7) 1 calc R U P B 1
H35 H -0.212729 0.255252 0.198559 0.091 Uiso 0.788(7) 1 calc R U P B 1
H36 H -0.141754 0.321608 0.245344 0.091 Uiso 0.788(7) 1 calc R U P B 1
C39 C -0.0732(3) 0.1007(6) 0.29607(18) 0.0790(15) Uani 0.788(7) 1 d . . P B 1
H37 H -0.037419 0.178293 0.306174 0.118 Uiso 0.788(7) 1 calc R U P B 1
H38 H -0.037168 0.022559 0.295269 0.118 Uiso 0.788(7) 1 calc R U P B 1
H39 H -0.111284 0.088249 0.324818 0.118 Uiso 0.788(7) 1 calc R U P B 1
C40 C -0.0962(15) 0.003(2) 0.2812(8) 0.098(7) Uani 0.212(7) 1 d . . P B 2
H40 H -0.132121 0.001980 0.311683 0.147 Uiso 0.212(7) 1 calc R U P B 2
H41 H -0.036716 0.016060 0.298489 0.147 Uiso 0.212(7) 1 calc R U P B 2
H42 H -0.101884 -0.080750 0.260360 0.147 Uiso 0.212(7) 1 calc R U P B 2
C41 C -0.2097(13) 0.107(3) 0.2134(9) 0.120(10) Uani 0.212(7) 1 d . . P B 2
H43 H -0.229771 0.189825 0.194530 0.180 Uiso 0.212(7) 1 calc R U P B 2
H44 H -0.244001 0.086127 0.243571 0.180 Uiso 0.212(7) 1 calc R U P B 2
H45 H -0.215073 0.035854 0.184869 0.180 Uiso 0.212(7) 1 calc R U P B 2
C42 C -0.1207(11) 0.2475(15) 0.2827(8) 0.081(6) Uani 0.212(7) 1 d . . P B 2
H46 H -0.126333 0.329707 0.260523 0.121 Uiso 0.212(7) 1 calc R U P B 2
H47 H -0.066148 0.246829 0.308361 0.121 Uiso 0.212(7) 1 calc R U P B 2
H48 H -0.167206 0.240895 0.305607 0.121 Uiso 0.212(7) 1 calc R U P B 2
C43 C 0.12825(13) -0.6049(2) -0.09582(9) 0.0389(5) Uani 1 1 d . . . . .
C44 C 0.05499(16) -0.6679(2) -0.07047(11) 0.0552(6) Uani 1 1 d . . . . .
H49 H 0.069567 -0.672533 -0.028444 0.083 Uiso 1 1 calc R U . . .
H50 H 0.044854 -0.757102 -0.086085 0.083 Uiso 1 1 calc R U . . .
H51 H 0.003514 -0.614687 -0.080612 0.083 Uiso 1 1 calc R U . . .
C45 C 0.20660(14) -0.6929(2) -0.08193(11) 0.0500(6) Uani 1 1 d . . . . .
H52 H 0.224657 -0.695035 -0.040148 0.075 Uiso 1 1 calc R U . . .
H53 H 0.252757 -0.657726 -0.100797 0.075 Uiso 1 1 calc R U . . .
H54 H 0.192621 -0.782444 -0.095955 0.075 Uiso 1 1 calc R U . . .
C46 C 0.10374(16) -0.5974(2) -0.16149(10) 0.0519(6) Uani 1 1 d . . . . .
H55 H 0.089511 -0.685844 -0.176800 0.078 Uiso 1 1 calc R U . . .
H56 H 0.151646 -0.562315 -0.178573 0.078 Uiso 1 1 calc R U . . .
H57 H 0.054400 -0.539345 -0.171037 0.078 Uiso 1 1 calc R U . . .
C47 C 0.51126(14) -0.1156(2) -0.13524(10) 0.0448(5) Uani 1 1 d . . . . .
C48 C 0.5740(2) 0.0006(4) -0.12561(19) 0.0636(13) Uani 0.701(4) 1 d . . P C 1
H58 H 0.622494 -0.016557 -0.145780 0.095 Uiso 0.701(4) 1 calc R U P C 1
H59 H 0.594053 0.010727 -0.084288 0.095 Uiso 0.701(4) 1 calc R U P C 1
H60 H 0.545263 0.081661 -0.140640 0.095 Uiso 0.701(4) 1 calc R U P C 1
C49 C 0.4754(2) -0.1257(5) -0.19816(15) 0.0608(12) Uani 0.701(4) 1 d . . P C 1
H61 H 0.434869 -0.198979 -0.204005 0.091 Uiso 0.701(4) 1 calc R U P C 1
H62 H 0.521670 -0.141343 -0.220569 0.091 Uiso 0.701(4) 1 calc R U P C 1
H63 H 0.446280 -0.043304 -0.210875 0.091 Uiso 0.701(4) 1 calc R U P C 1
C50 C 0.5584(2) -0.2415(4) -0.11427(19) 0.0598(12) Uani 0.701(4) 1 d . . P C 1
H64 H 0.520304 -0.317235 -0.122407 0.090 Uiso 0.701(4) 1 calc R U P C 1
H65 H 0.577550 -0.235432 -0.072671 0.090 Uiso 0.701(4) 1 calc R U P C 1
H66 H 0.607810 -0.252624 -0.134256 0.090 Uiso 0.701(4) 1 calc R U P C 1
C51 C 0.5942(6) -0.1000(13) -0.0960(5) 0.077(3) Uani 0.299(4) 1 d . . P C 2
H67 H 0.593952 -0.016970 -0.074670 0.115 Uiso 0.299(4) 1 calc R U P C 2
H68 H 0.640898 -0.098954 -0.118914 0.115 Uiso 0.299(4) 1 calc R U P C 2
H69 H 0.602075 -0.173806 -0.068783 0.115 Uiso 0.299(4) 1 calc R U P C 2
C52 C 0.5083(6) -0.0097(10) -0.1835(4) 0.067(3) Uani 0.299(4) 1 d . . P C 2
H70 H 0.512734 0.078367 -0.166113 0.101 Uiso 0.299(4) 1 calc R U P C 2
H71 H 0.454433 -0.017031 -0.209774 0.101 Uiso 0.299(4) 1 calc R U P C 2
H72 H 0.555758 -0.023652 -0.205017 0.101 Uiso 0.299(4) 1 calc R U P C 2
C53 C 0.5147(7) -0.2522(9) -0.1673(5) 0.075(4) Uani 0.299(4) 1 d . . P C 2
H73 H 0.565899 -0.255669 -0.185833 0.112 Uiso 0.299(4) 1 calc R U P C 2
H74 H 0.464213 -0.261433 -0.196539 0.112 Uiso 0.299(4) 1 calc R U P C 2
H75 H 0.516211 -0.324225 -0.139298 0.112 Uiso 0.299(4) 1 calc R U P C 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'
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 C3 177.2(2) . . ?
C1 C2 C4 178.0(2) . . ?
C1 C3 C16 126.10(19) . . ?
C1 C3 C5 127.44(19) . . ?
C16 C3 C5 106.37(17) . . ?
C2 C4 C28 127.6(2) . . ?
C2 C4 C17 126.20(19) . . ?
C28 C4 C17 106.16(17) . . ?
C6 C5 C10 119.83(19) . . ?
C6 C5 C3 131.45(19) . . ?
C10 C5 C3 108.68(17) . . ?
C5 C6 C7 119.18(19) . . ?
C5 C6 H1 120.4 . . ?
C7 C6 H1 120.4 . . ?
C6 C7 C8 122.3(2) . . ?
C6 C7 H2 118.9 . . ?
C8 C7 H2 118.9 . . ?
C9 C8 C7 117.90(19) . . ?
C9 C8 C29 121.29(19) . . ?
C7 C8 C29 120.80(19) . . ?
C10 C9 C8 120.98(19) . . ?
C10 C9 H3 119.5 . . ?
C8 C9 H3 119.5 . . ?
C9 C10 C5 119.85(18) . . ?
C9 C10 C11 132.24(18) . . ?
C5 C10 C11 107.89(17) . . ?
C12 C11 C16 119.94(19) . . ?
C12 C11 C10 131.85(18) . . ?
C16 C11 C10 108.20(17) . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H4 119.8 . . ?
C13 C12 H4 119.8 . . ?
C14 C13 C12 118.19(19) . . ?
C14 C13 C36 121.91(19) . . ?
C12 C13 C36 119.9(2) . . ?
C15 C14 C13 122.2(2) . . ?
C15 C14 H5 118.9 . . ?
C13 C14 H5 118.9 . . ?
C14 C15 C16 119.3(2) . . ?
C14 C15 H6 120.3 . . ?
C16 C15 H6 120.3 . . ?
C15 C16 C11 119.95(19) . . ?
C15 C16 C3 131.2(2) . . ?
C11 C16 C3 108.80(18) . . ?
C18 C17 C22 120.05(19) . . ?
C18 C17 C4 131.40(19) . . ?
C22 C17 C4 108.54(17) . . ?
C17 C18 C19 118.91(19) . . ?
C17 C18 H7 120.5 . . ?
C19 C18 H7 120.5 . . ?
C18 C19 C20 122.16(19) . . ?
C18 C19 H8 118.9 . . ?
C20 C19 H8 118.9 . . ?
C21 C20 C19 118.06(18) . . ?
C21 C20 C43 119.57(17) . . ?
C19 C20 C43 122.36(18) . . ?
C22 C21 C20 120.38(18) . . ?
C22 C21 H9 119.8 . . ?
C20 C21 H9 119.8 . . ?
C21 C22 C17 120.44(18) . . ?
C21 C22 C23 131.08(18) . . ?
C17 C22 C23 108.48(17) . . ?
C24 C23 C28 120.44(19) . . ?
C24 C23 C22 131.30(19) . . ?
C28 C23 C22 108.24(17) . . ?
C23 C24 C25 120.7(2) . . ?
C23 C24 H10 119.7 . . ?
C25 C24 H10 119.7 . . ?
C26 C25 C24 117.77(19) . . ?
C26 C25 C47 122.14(19) . . ?
C24 C25 C47 120.08(19) . . ?
C27 C26 C25 122.7(2) . . ?
C27 C26 H11 118.7 . . ?
C25 C26 H11 118.7 . . ?
C28 C27 C26 118.8(2) . . ?
C28 C27 H12 120.6 . . ?
C26 C27 H12 120.6 . . ?
C27 C28 C23 119.60(19) . . ?
C27 C28 C4 131.8(2) . . ?
C23 C28 C4 108.57(18) . . ?
C34 C29 C8 116.6(4) . . ?
C30 C29 C8 116.8(3) . . ?
C30 C29 C32 110.7(4) . . ?
C8 C29 C32 108.4(2) . . ?
C34 C29 C33 112.1(6) . . ?
C8 C29 C33 106.0(4) . . ?
C30 C29 C31 107.4(4) . . ?
C8 C29 C31 107.9(3) . . ?
C32 C29 C31 105.0(4) . . ?
C34 C29 C35 111.7(6) . . ?
C8 C29 C35 106.0(3) . . ?
C33 C29 C35 103.2(6) . . ?
C29 C30 H13 109.5 . . ?
C29 C30 H14 109.5 . . ?
H13 C30 H14 109.5 . . ?
C29 C30 H15 109.5 . . ?
H13 C30 H15 109.5 . . ?
H14 C30 H15 109.5 . . ?
C29 C31 H16 109.5 . . ?
C29 C31 H17 109.5 . . ?
H16 C31 H17 109.5 . . ?
C29 C31 H18 109.5 . . ?
H16 C31 H18 109.5 . . ?
H17 C31 H18 109.5 . . ?
C29 C32 H19 109.5 . . ?
C29 C32 H20 109.5 . . ?
H19 C32 H20 109.5 . . ?
C29 C32 H21 109.5 . . ?
H19 C32 H21 109.5 . . ?
H20 C32 H21 109.5 . . ?
C29 C33 H22 109.5 . . ?
C29 C33 H23 109.5 . . ?
H22 C33 H23 109.5 . . ?
C29 C33 H24 109.5 . . ?
H22 C33 H24 109.5 . . ?
H23 C33 H24 109.5 . . ?
C29 C34 H25 109.5 . . ?
C29 C34 H26 109.5 . . ?
H25 C34 H26 109.5 . . ?
C29 C34 H27 109.5 . . ?
H25 C34 H27 109.5 . . ?
H26 C34 H27 109.5 . . ?
C29 C35 H28 109.5 . . ?
C29 C35 H29 109.5 . . ?
H28 C35 H29 109.5 . . ?
C29 C35 H30 109.5 . . ?
H28 C35 H30 109.5 . . ?
H29 C35 H30 109.5 . . ?
C39 C36 C38 110.8(3) . . ?
C41 C36 C13 114.0(8) . . ?
C39 C36 C13 107.8(2) . . ?
C38 C36 C13 110.2(2) . . ?
C39 C36 C37 109.7(3) . . ?
C38 C36 C37 106.8(3) . . ?
C13 C36 C37 111.5(2) . . ?
C41 C36 C40 111.2(12) . . ?
C13 C36 C40 109.5(7) . . ?
C41 C36 C42 106.4(13) . . ?
C13 C36 C42 113.8(5) . . ?
C40 C36 C42 101.2(10) . . ?
C36 C37 H31 109.5 . . ?
C36 C37 H32 109.5 . . ?
H31 C37 H32 109.5 . . ?
C36 C37 H33 109.5 . . ?
H31 C37 H33 109.5 . . ?
H32 C37 H33 109.5 . . ?
C36 C38 H34 109.5 . . ?
C36 C38 H35 109.5 . . ?
H34 C38 H35 109.5 . . ?
C36 C38 H36 109.5 . . ?
H34 C38 H36 109.5 . . ?
H35 C38 H36 109.5 . . ?
C36 C39 H37 109.5 . . ?
C36 C39 H38 109.5 . . ?
H37 C39 H38 109.5 . . ?
C36 C39 H39 109.5 . . ?
H37 C39 H39 109.5 . . ?
H38 C39 H39 109.5 . . ?
C36 C40 H40 109.5 . . ?
C36 C40 H41 109.5 . . ?
H40 C40 H41 109.5 . . ?
C36 C40 H42 109.5 . . ?
H40 C40 H42 109.5 . . ?
H41 C40 H42 109.5 . . ?
C36 C41 H43 109.5 . . ?
C36 C41 H44 109.5 . . ?
H43 C41 H44 109.5 . . ?
C36 C41 H45 109.5 . . ?
H43 C41 H45 109.5 . . ?
H44 C41 H45 109.5 . . ?
C36 C42 H46 109.5 . . ?
C36 C42 H47 109.5 . . ?
H46 C42 H47 109.5 . . ?
C36 C42 H48 109.5 . . ?
H46 C42 H48 109.5 . . ?
H47 C42 H48 109.5 . . ?
C44 C43 C45 108.54(18) . . ?
C44 C43 C46 108.59(18) . . ?
C45 C43 C46 108.61(19) . . ?
C44 C43 C20 112.04(17) . . ?
C45 C43 C20 110.49(17) . . ?
C46 C43 C20 108.51(17) . . ?
C43 C44 H49 109.5 . . ?
C43 C44 H50 109.5 . . ?
H49 C44 H50 109.5 . . ?
C43 C44 H51 109.5 . . ?
H49 C44 H51 109.5 . . ?
H50 C44 H51 109.5 . . ?
C43 C45 H52 109.5 . . ?
C43 C45 H53 109.5 . . ?
H52 C45 H53 109.5 . . ?
C43 C45 H54 109.5 . . ?
H52 C45 H54 109.5 . . ?
H53 C45 H54 109.5 . . ?
C43 C46 H55 109.5 . . ?
C43 C46 H56 109.5 . . ?
H55 C46 H56 109.5 . . ?
C43 C46 H57 109.5 . . ?
H55 C46 H57 109.5 . . ?
H56 C46 H57 109.5 . . ?
C49 C47 C50 110.8(3) . . ?
C51 C47 C25 111.5(4) . . ?
C49 C47 C25 106.7(2) . . ?
C50 C47 C25 109.1(2) . . ?
C49 C47 C48 109.7(3) . . ?
C50 C47 C48 108.5(3) . . ?
C25 C47 C48 112.0(2) . . ?
C51 C47 C52 107.5(6) . . ?
C25 C47 C52 109.8(4) . . ?
C51 C47 C53 107.1(6) . . ?
C25 C47 C53 115.4(4) . . ?
C52 C47 C53 105.0(6) . . ?
C47 C48 H58 109.5 . . ?
C47 C48 H59 109.5 . . ?
H58 C48 H59 109.5 . . ?
C47 C48 H60 109.5 . . ?
H58 C48 H60 109.5 . . ?
H59 C48 H60 109.5 . . ?
C47 C49 H61 109.5 . . ?
C47 C49 H62 109.5 . . ?
H61 C49 H62 109.5 . . ?
C47 C49 H63 109.5 . . ?
H61 C49 H63 109.5 . . ?
H62 C49 H63 109.5 . . ?
C47 C50 H64 109.5 . . ?
C47 C50 H65 109.5 . . ?
H64 C50 H65 109.5 . . ?
C47 C50 H66 109.5 . . ?
H64 C50 H66 109.5 . . ?
H65 C50 H66 109.5 . . ?
C47 C51 H67 109.5 . . ?
C47 C51 H68 109.5 . . ?
H67 C51 H68 109.5 . . ?
C47 C51 H69 109.5 . . ?
H67 C51 H69 109.5 . . ?
H68 C51 H69 109.5 . . ?
C47 C52 H70 109.5 . . ?
C47 C52 H71 109.5 . . ?
H70 C52 H71 109.5 . . ?
C47 C52 H72 109.5 . . ?
H70 C52 H72 109.5 . . ?
H71 C52 H72 109.5 . . ?
C47 C53 H73 109.5 . . ?
C47 C53 H74 109.5 . . ?
H73 C53 H74 109.5 . . ?
C47 C53 H75 109.5 . . ?
H73 C53 H75 109.5 . . ?
H74 C53 H75 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 1.241(3) . ?
C1 C3 1.346(3) . ?
C2 C4 1.347(3) . ?
C3 C16 1.462(3) . ?
C3 C5 1.464(3) . ?
C4 C28 1.468(3) . ?
C4 C17 1.476(3) . ?
C5 C6 1.380(3) . ?
C5 C10 1.415(3) . ?
C6 C7 1.386(3) . ?
C6 H1 0.9500 . ?
C7 C8 1.397(3) . ?
C7 H2 0.9500 . ?
C8 C9 1.394(3) . ?
C8 C29 1.534(3) . ?
C9 C10 1.383(3) . ?
C9 H3 0.9500 . ?
C10 C11 1.467(3) . ?
C11 C12 1.387(3) . ?
C11 C16 1.409(3) . ?
C12 C13 1.402(3) . ?
C12 H4 0.9500 . ?
C13 C14 1.392(3) . ?
C13 C36 1.538(3) . ?
C14 C15 1.381(3) . ?
C14 H5 0.9500 . ?
C15 C16 1.380(3) . ?
C15 H6 0.9500 . ?
C17 C18 1.374(3) . ?
C17 C22 1.399(3) . ?
C18 C19 1.390(3) . ?
C18 H7 0.9500 . ?
C19 C20 1.395(3) . ?
C19 H8 0.9500 . ?
C20 C21 1.390(3) . ?
C20 C43 1.535(3) . ?
C21 C22 1.385(3) . ?
C21 H9 0.9500 . ?
C22 C23 1.469(3) . ?
C23 C24 1.383(3) . ?
C23 C28 1.407(3) . ?
C24 C25 1.393(3) . ?
C24 H10 0.9500 . ?
C25 C26 1.391(3) . ?
C25 C47 1.531(3) . ?
C26 C27 1.388(3) . ?
C26 H11 0.9500 . ?
C27 C28 1.383(3) . ?
C27 H12 0.9500 . ?
C29 C34 1.400(8) . ?
C29 C30 1.448(5) . ?
C29 C32 1.560(5) . ?
C29 C33 1.579(9) . ?
C29 C31 1.598(6) . ?
C29 C35 1.613(7) . ?
C30 H13 0.9800 . ?
C30 H14 0.9800 . ?
C30 H15 0.9800 . ?
C31 H16 0.9800 . ?
C31 H17 0.9800 . ?
C31 H18 0.9800 . ?
C32 H19 0.9800 . ?
C32 H20 0.9800 . ?
C32 H21 0.9800 . ?
C33 H22 0.9800 . ?
C33 H23 0.9800 . ?
C33 H24 0.9800 . ?
C34 H25 0.9800 . ?
C34 H26 0.9800 . ?
C34 H27 0.9800 . ?
C35 H28 0.9800 . ?
C35 H29 0.9800 . ?
C35 H30 0.9800 . ?
C36 C41 1.389(19) . ?
C36 C39 1.499(5) . ?
C36 C38 1.525(4) . ?
C36 C37 1.551(4) . ?
C36 C40 1.587(16) . ?
C36 C42 1.659(16) . ?
C37 H31 0.9800 . ?
C37 H32 0.9800 . ?
C37 H33 0.9800 . ?
C38 H34 0.9800 . ?
C38 H35 0.9800 . ?
C38 H36 0.9800 . ?
C39 H37 0.9800 . ?
C39 H38 0.9800 . ?
C39 H39 0.9800 . ?
C40 H40 0.9800 . ?
C40 H41 0.9800 . ?
C40 H42 0.9800 . ?
C41 H43 0.9800 . ?
C41 H44 0.9800 . ?
C41 H45 0.9800 . ?
C42 H46 0.9800 . ?
C42 H47 0.9800 . ?
C42 H48 0.9800 . ?
C43 C44 1.526(3) . ?
C43 C45 1.528(3) . ?
C43 C46 1.534(3) . ?
C44 H49 0.9800 . ?
C44 H50 0.9800 . ?
C44 H51 0.9800 . ?
C45 H52 0.9800 . ?
C45 H53 0.9800 . ?
C45 H54 0.9800 . ?
C46 H55 0.9800 . ?
C46 H56 0.9800 . ?
C46 H57 0.9800 . ?
C47 C51 1.500(10) . ?
C47 C49 1.505(4) . ?
C47 C50 1.524(4) . ?
C47 C48 1.539(4) . ?
C47 C52 1.557(9) . ?
C47 C53 1.581(9) . ?
C48 H58 0.9800 . ?
C48 H59 0.9800 . ?
C48 H60 0.9800 . ?
C49 H61 0.9800 . ?
C49 H62 0.9800 . ?
C49 H63 0.9800 . ?
C50 H64 0.9800 . ?
C50 H65 0.9800 . ?
C50 H66 0.9800 . ?
C51 H67 0.9800 . ?
C51 H68 0.9800 . ?
C51 H69 0.9800 . ?
C52 H70 0.9800 . ?
C52 H71 0.9800 . ?
C52 H72 0.9800 . ?
C53 H73 0.9800 . ?
C53 H74 0.9800 . ?
C53 H75 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
C1 C3 C5 C6 3.0(4) . . . . ?
C16 C3 C5 C6 179.7(2) . . . . ?
C1 C3 C5 C10 -174.8(2) . . . . ?
C16 C3 C5 C10 1.8(2) . . . . ?
C10 C5 C6 C7 -0.4(3) . . . . ?
C3 C5 C6 C7 -178.1(2) . . . . ?
C5 C6 C7 C8 1.0(4) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C6 C7 C8 C29 179.6(2) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C29 C8 C9 C10 179.8(2) . . . . ?
C8 C9 C10 C5 0.1(3) . . . . ?
C8 C9 C10 C11 178.3(2) . . . . ?
C6 C5 C10 C9 -0.1(3) . . . . ?
C3 C5 C10 C9 178.05(18) . . . . ?
C6 C5 C10 C11 -178.65(18) . . . . ?
C3 C5 C10 C11 -0.5(2) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C5 C10 C11 C12 177.4(2) . . . . ?
C9 C10 C11 C16 -179.4(2) . . . . ?
C5 C10 C11 C16 -1.1(2) . . . . ?
C16 C11 C12 C13 -0.6(3) . . . . ?
C10 C11 C12 C13 -179.0(2) . . . . ?
C11 C12 C13 C14 -1.2(3) . . . . ?
C11 C12 C13 C36 176.4(2) . . . . ?
C12 C13 C14 C15 1.8(4) . . . . ?
C36 C13 C14 C15 -175.7(2) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C11 -1.4(3) . . . . ?
C14 C15 C16 C3 176.7(2) . . . . ?
C12 C11 C16 C15 1.9(3) . . . . ?
C10 C11 C16 C15 -179.35(19) . . . . ?
C12 C11 C16 C3 -176.49(19) . . . . ?
C10 C11 C16 C3 2.2(2) . . . . ?
C1 C3 C16 C15 -4.0(4) . . . . ?
C5 C3 C16 C15 179.3(2) . . . . ?
C1 C3 C16 C11 174.2(2) . . . . ?
C5 C3 C16 C11 -2.5(2) . . . . ?
C2 C4 C17 C18 2.6(4) . . . . ?
C28 C4 C17 C18 -179.6(2) . . . . ?
C2 C4 C17 C22 -178.3(2) . . . . ?
C28 C4 C17 C22 -0.5(2) . . . . ?
C22 C17 C18 C19 0.9(3) . . . . ?
C4 C17 C18 C19 179.9(2) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C18 C19 C20 C43 -179.1(2) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C43 C20 C21 C22 179.66(19) . . . . ?
C20 C21 C22 C17 -0.3(3) . . . . ?
C20 C21 C22 C23 179.0(2) . . . . ?
C18 C17 C22 C21 -0.5(3) . . . . ?
C4 C17 C22 C21 -179.68(19) . . . . ?
C18 C17 C22 C23 -179.9(2) . . . . ?
C4 C17 C22 C23 0.9(2) . . . . ?
C21 C22 C23 C24 -1.8(4) . . . . ?
C17 C22 C23 C24 177.5(2) . . . . ?
C21 C22 C23 C28 179.7(2) . . . . ?
C17 C22 C23 C28 -0.9(2) . . . . ?
C28 C23 C24 C25 -0.3(3) . . . . ?
C22 C23 C24 C25 -178.6(2) . . . . ?
C23 C24 C25 C26 0.0(3) . . . . ?
C23 C24 C25 C47 -179.0(2) . . . . ?
C24 C25 C26 C27 0.2(4) . . . . ?
C47 C25 C26 C27 179.1(2) . . . . ?
C25 C26 C27 C28 -0.1(4) . . . . ?
C26 C27 C28 C23 -0.1(3) . . . . ?
C26 C27 C28 C4 177.8(2) . . . . ?
C24 C23 C28 C27 0.3(3) . . . . ?
C22 C23 C28 C27 179.0(2) . . . . ?
C24 C23 C28 C4 -178.1(2) . . . . ?
C22 C23 C28 C4 0.6(2) . . . . ?
C2 C4 C28 C27 -0.4(4) . . . . ?
C17 C4 C28 C27 -178.2(2) . . . . ?
C2 C4 C28 C23 177.7(2) . . . . ?
C17 C4 C28 C23 -0.1(2) . . . . ?
C9 C8 C29 C34 7.7(7) . . . . ?
C7 C8 C29 C34 -172.8(7) . . . . ?
C9 C8 C29 C30 173.4(4) . . . . ?
C7 C8 C29 C30 -7.1(5) . . . . ?
C9 C8 C29 C32 -60.8(4) . . . . ?
C7 C8 C29 C32 118.7(3) . . . . ?
C9 C8 C29 C33 133.3(5) . . . . ?
C7 C8 C29 C33 -47.2(5) . . . . ?
C9 C8 C29 C31 52.3(4) . . . . ?
C7 C8 C29 C31 -128.2(3) . . . . ?
C9 C8 C29 C35 -117.4(4) . . . . ?
C7 C8 C29 C35 62.1(4) . . . . ?
C14 C13 C36 C41 -59.8(15) . . . . ?
C12 C13 C36 C41 122.7(14) . . . . ?
C14 C13 C36 C39 109.2(3) . . . . ?
C12 C13 C36 C39 -68.3(3) . . . . ?
C14 C13 C36 C38 -129.7(3) . . . . ?
C12 C13 C36 C38 52.8(3) . . . . ?
C14 C13 C36 C37 -11.3(4) . . . . ?
C12 C13 C36 C37 171.2(3) . . . . ?
C14 C13 C36 C40 65.5(10) . . . . ?
C12 C13 C36 C40 -112.0(10) . . . . ?
C14 C13 C36 C42 177.9(8) . . . . ?
C12 C13 C36 C42 0.4(8) . . . . ?
C21 C20 C43 C44 173.48(19) . . . . ?
C19 C20 C43 C44 -7.5(3) . . . . ?
C21 C20 C43 C45 52.3(3) . . . . ?
C19 C20 C43 C45 -128.6(2) . . . . ?
C21 C20 C43 C46 -66.6(2) . . . . ?
C19 C20 C43 C46 112.4(2) . . . . ?
C26 C25 C47 C51 58.9(6) . . . . ?
C24 C25 C47 C51 -122.2(6) . . . . ?
C26 C25 C47 C49 -113.8(3) . . . . ?
C24 C25 C47 C49 65.1(3) . . . . ?
C26 C25 C47 C50 126.5(3) . . . . ?
C24 C25 C47 C50 -54.6(3) . . . . ?
C26 C25 C47 C48 6.3(4) . . . . ?
C24 C25 C47 C48 -174.7(3) . . . . ?
C26 C25 C47 C52 -60.3(5) . . . . ?
C24 C25 C47 C52 118.7(5) . . . . ?
C26 C25 C47 C53 -178.6(6) . . . . ?
C24 C25 C47 C53 0.3(6) . . . . ?
