#------------------------------------------------------------------------------
#$Date: 2020-05-06 03:12:26 +0300 (Wed, 06 May 2020) $
#$Revision: 251802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038256.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_4038256
loop_
_publ_author_name
'Yakiyama, Yumi'
'Hishikawa, Shota'
'Sakurai, Hidehiro'
_publ_section_title
;
 Synthesis of C₇₀-fragment buckybowls bearing alkoxy
 substituents.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              681
_journal_page_last               690
_journal_paper_doi               10.3762/bjoc.16.66
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C29 H14 O2'
_chemical_formula_sum            'C29 H14 O2'
_chemical_formula_weight         394.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.62(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.274(4)
_cell_length_b                   7.4408(15)
_cell_length_c                   27.913(6)
_cell_measurement_reflns_used    3950
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      3.03
_cell_volume                     3526.3(14)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'?'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku R-AXIS VII area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1884
_diffrn_reflns_av_unetI/netI     0.3510
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19291
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.026
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9999
_exptl_absorpt_correction_T_min  0.5437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         7995
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.3593
_refine_ls_R_factor_gt           0.1217
_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)+(0.0558P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.2096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2351
_reflns_number_total             7995
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Dioxole-5c-re.cif
_cod_data_source_block           Dioxole5c
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_cell_measurement_temperature' value '150(2' was changed
to '150(2)' -- precision was estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4038256--4038257.cif.
;
_cod_original_cell_volume        3526.2(13)
_cod_database_code               4038256
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C23, C24, C25, C26, C27, C28
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C28: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C23, C24
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C13(H13A,H13B), C29(H29A,H29B), C37(H37A,H37B), C42(H42A,H42B),
 C58(H58A,H58B)
5.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C15(H15), C16(H16), C18(H18), C22(H22), C25(H25),
 C26(H26), C39(H39), C40(H40), C44(H44), C45(H45), C47(H47), C51(H51), C54(H54),
  C55(H55)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.3024(2) 0.0242(5) 0.36021(13) 0.0589(12) Uani 1 1 d . . . . .
O2 O 0.2501(3) 0.1422(6) 0.42428(13) 0.0770(14) Uani 1 1 d . . . . .
O3 O 0.5032(3) 0.0937(6) 0.11413(14) 0.0717(14) Uani 1 1 d . . . . .
O4 O 0.5680(3) 0.1391(7) 0.05000(14) 0.0904(16) Uani 1 1 d . . . . .
C1 C 0.1170(3) -0.0211(7) 0.17136(19) 0.0338(14) Uani 1 1 d . . . . .
C2 C 0.0497(3) 0.0519(7) 0.1396(2) 0.0381(15) Uani 1 1 d . . . . .
C3 C 0.0547(3) 0.0665(8) 0.0907(2) 0.0438(16) Uani 1 1 d . . . . .
C4 C 0.1239(4) 0.0197(7) 0.0733(2) 0.0410(16) Uani 1 1 d . . . . .
C5 C 0.1888(4) -0.0463(7) 0.1043(2) 0.0429(16) Uani 1 1 d . . . . .
C6 C 0.1852(4) -0.0653(7) 0.1545(2) 0.0410(15) Uani 1 1 d . . . . .
C7 C 0.2596(3) -0.0728(7) 0.1825(2) 0.0406(15) Uani 1 1 d . . . . .
C8 C 0.3194(3) -0.0651(7) 0.14699(17) 0.0460(16) Uani 1 1 d . . . . .
H8A H 0.347495 -0.177923 0.146870 0.055 Uiso 1 1 calc R . . . .
H8B H 0.357097 0.031362 0.155689 0.055 Uiso 1 1 calc R . . . .
C9 C 0.2654(4) -0.0293(7) 0.0967(2) 0.0512(17) Uani 1 1 d . . . . .
C10 C 0.2720(4) 0.0384(8) 0.0518(2) 0.0570(18) Uani 1 1 d . . . . .
H10 H 0.321277 0.042188 0.042904 0.068 Uiso 1 1 calc R . . . .
C11 C 0.2049(4) 0.1031(8) 0.01833(19) 0.0530(17) Uani 1 1 d . . . . .
H11 H 0.211766 0.146474 -0.011853 0.064 Uiso 1 1 calc R . . . .
C12 C 0.1297(4) 0.1029(8) 0.0297(2) 0.0474(17) Uani 1 1 d . . . . .
C13 C 0.0511(3) 0.2038(7) 0.01268(18) 0.0556(18) Uani 1 1 d . . . . .
H13A H 0.020596 0.149558 -0.016374 0.067 Uiso 1 1 calc R . . . .
H13B H 0.059964 0.329655 0.006380 0.067 Uiso 1 1 calc R . . . .
C14 C 0.0098(4) 0.1804(9) 0.0573(2) 0.0590(19) Uani 1 1 d . . . . .
C15 C -0.0513(3) 0.2646(8) 0.0741(2) 0.0619(19) Uani 1 1 d . . . . .
H15 H -0.087284 0.332589 0.052621 0.074 Uiso 1 1 calc R . . . .
C16 C -0.0603(3) 0.2496(8) 0.1231(2) 0.0505(17) Uani 1 1 d . . . . .
H16 H -0.102948 0.306053 0.132776 0.061 Uiso 1 1 calc R . . . .
C17 C -0.0069(3) 0.1521(8) 0.1583(2) 0.0453(16) Uani 1 1 d . . . . .
C18 C 0.0022(3) 0.1685(7) 0.2108(2) 0.0473(16) Uani 1 1 d . . . . .
H18 H -0.036548 0.225901 0.224322 0.057 Uiso 1 1 calc R . . . .
C19 C 0.0664(3) 0.1012(7) 0.2402(2) 0.0406(15) Uani 1 1 d . . . . .
C20 C 0.1255(3) 0.0112(7) 0.2203(2) 0.0389(15) Uani 1 1 d . . . . .
C21 C 0.1986(4) -0.0078(7) 0.25184(19) 0.0442(16) Uani 1 1 d . . . . .
C22 C 0.2676(3) -0.0463(7) 0.23378(18) 0.0430(15) Uani 1 1 d . . . . .
H22 H 0.316378 -0.054162 0.254396 0.052 Uiso 1 1 calc R . . . .
C23 C 0.1812(3) 0.0581(7) 0.29855(19) 0.0423(15) Uani 1 1 d . U . . .
C24 C 0.1027(3) 0.1258(7) 0.2924(2) 0.0476(16) Uani 1 1 d . U . . .
C25 C 0.0739(3) 0.2030(7) 0.3316(2) 0.0476(16) Uani 1 1 d . U . . .
H25 H 0.022793 0.247725 0.326176 0.057 Uiso 1 1 calc R . . . .
C26 C 0.1186(4) 0.2148(8) 0.3776(2) 0.0620(18) Uani 1 1 d . U . . .
H26 H 0.099449 0.264266 0.403674 0.074 Uiso 1 1 calc R . . . .
C27 C 0.1933(4) 0.1485(8) 0.3821(2) 0.0514(17) Uani 1 1 d . U . . .
C28 C 0.2250(4) 0.0774(8) 0.3444(2) 0.0495(16) Uani 1 1 d . U . . .
C29 C 0.3210(4) 0.0934(9) 0.4086(2) 0.076(2) Uani 1 1 d . . . . .
H29A H 0.348759 0.003067 0.430234 0.091 Uiso 1 1 calc R . . . .
H29B H 0.354882 0.197708 0.409325 0.091 Uiso 1 1 calc R . . . .
C30 C 0.6725(3) -0.0914(7) 0.3018(2) 0.0430(16) Uani 1 1 d . . . . .
C31 C 0.7473(4) -0.0874(7) 0.3330(2) 0.0446(16) Uani 1 1 d . . . . .
C32 C 0.7477(3) -0.0642(7) 0.3829(2) 0.0433(16) Uani 1 1 d . . . . .
C33 C 0.6766(4) -0.0460(7) 0.4013(2) 0.0444(16) Uani 1 1 d . . . . .
C34 C 0.6062(3) -0.0472(7) 0.3702(2) 0.0388(15) Uani 1 1 d . . . . .
C35 C 0.6025(3) -0.0694(7) 0.3194(2) 0.0448(16) Uani 1 1 d . . . . .
C36 C 0.5325(3) -0.0042(8) 0.2926(2) 0.0427(16) Uani 1 1 d . . . . .
C37 C 0.4809(3) 0.0562(8) 0.32967(17) 0.0533(18) Uani 1 1 d . . . . .
H37A H 0.462797 0.178867 0.323582 0.064 Uiso 1 1 calc R . . . .
H37B H 0.435702 -0.022142 0.328536 0.064 Uiso 1 1 calc R . . . .
C38 C 0.5383(4) 0.0400(8) 0.3791(2) 0.0536(18) Uani 1 1 d . . . . .
C39 C 0.5469(3) 0.1208(8) 0.4245(2) 0.0556(18) Uani 1 1 d . . . . .
H39 H 0.503845 0.177256 0.433593 0.067 Uiso 1 1 calc R . . . .
C40 C 0.6210(4) 0.1191(8) 0.4577(2) 0.0570(18) Uani 1 1 d . . . . .
H40 H 0.624125 0.170443 0.488397 0.068 Uiso 1 1 calc R . . . .
C41 C 0.6872(4) 0.0442(8) 0.4456(2) 0.0487(17) Uani 1 1 d . . . . .
C42 C 0.7773(3) 0.0632(7) 0.46229(18) 0.0550(17) Uani 1 1 d . . . . .
H42A H 0.796308 -0.013021 0.490173 0.066 Uiso 1 1 calc R . . . .
H42B H 0.791871 0.186753 0.470644 0.066 Uiso 1 1 calc R . . . .
C43 C 0.8102(4) 0.0012(8) 0.4170(2) 0.0512(17) Uani 1 1 d . . . . .
C44 C 0.8793(4) 0.0283(8) 0.3997(2) 0.0629(19) Uani 1 1 d . . . . .
H44 H 0.924344 0.064866 0.421106 0.075 Uiso 1 1 calc R . . . .
C45 C 0.8822(4) 0.0012(7) 0.3506(3) 0.0602(19) Uani 1 1 d . . . . .
H45 H 0.930296 0.016381 0.340575 0.072 Uiso 1 1 calc R . . . .
C46 C 0.8165(4) -0.0476(8) 0.3154(2) 0.0553(18) Uani 1 1 d . . . . .
C47 C 0.8090(4) -0.0259(7) 0.2632(3) 0.0621(19) Uani 1 1 d . . . . .
H47 H 0.854432 -0.011655 0.250157 0.075 Uiso 1 1 calc R . . . .
C48 C 0.7383(4) -0.0256(8) 0.2328(2) 0.0498(17) Uani 1 1 d . . . . .
C49 C 0.6688(3) -0.0552(7) 0.2531(2) 0.0415(15) Uani 1 1 d . . . . .
C50 C 0.5984(3) -0.0036(8) 0.2228(2) 0.0483(17) Uani 1 1 d . . . . .
C51 C 0.5297(3) 0.0267(7) 0.24192(18) 0.0475(16) Uani 1 1 d . . . . .
H51 H 0.483568 0.065963 0.222005 0.057 Uiso 1 1 calc R . . . .
C52 C 0.6229(4) 0.0361(7) 0.1759(2) 0.0487(17) Uani 1 1 d . . . . .
C53 C 0.7074(4) 0.0234(8) 0.1810(2) 0.0539(17) Uani 1 1 d . . . . .
C54 C 0.7453(4) 0.0559(8) 0.1423(2) 0.0622(19) Uani 1 1 d . . . . .
H54 H 0.799946 0.051700 0.147013 0.075 Uiso 1 1 calc R . . . .
C55 C 0.7017(5) 0.0950(8) 0.0965(2) 0.066(2) Uani 1 1 d . . . . .
H55 H 0.726187 0.114301 0.069900 0.079 Uiso 1 1 calc R . . . .
C56 C 0.6217(4) 0.1038(8) 0.0919(3) 0.0599(19) Uani 1 1 d . . . . .
C57 C 0.5832(4) 0.0749(8) 0.1299(2) 0.0557(18) Uani 1 1 d . . . . .
C58 C 0.4927(4) 0.1284(9) 0.0628(2) 0.074(2) Uani 1 1 d . . . . .
H58A H 0.462428 0.032344 0.044712 0.089 Uiso 1 1 calc R . . . .
H58B H 0.464431 0.240402 0.054998 0.089 Uiso 1 1 calc R . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C28 O1 C29 103.6(4) . . ?
C27 O2 C29 105.1(4) . . ?
C57 O3 C58 105.8(5) . . ?
C56 O4 C58 106.4(4) . . ?
C6 C1 C2 121.5(5) . . ?
C20 C1 C2 118.4(5) . . ?
C20 C1 C6 116.1(5) . . ?
C3 C2 C1 116.6(5) . . ?
C3 C2 C17 119.8(6) . . ?
C17 C2 C1 120.9(5) . . ?
C2 C3 C4 121.8(6) . . ?
C14 C3 C2 125.4(6) . . ?
C14 C3 C4 109.0(6) . . ?
C5 C4 C3 121.0(5) . . ?
C5 C4 C12 122.1(6) . . ?
C12 C4 C3 113.1(6) . . ?
C4 C5 C6 118.6(5) . . ?
C4 C5 C9 124.2(6) . . ?
C9 C5 C6 112.2(6) . . ?
C1 C6 C5 120.4(6) . . ?
C7 C6 C1 125.3(5) . . ?
C7 C6 C5 111.0(5) . . ?
C6 C7 C8 107.2(4) . . ?
C6 C7 C22 118.2(5) . . ?
C22 C7 C8 132.8(5) . . ?
C7 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
C7 C8 C9 102.9(4) . . ?
H8A C8 H8B 109.1 . . ?
C9 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
C5 C9 C8 105.9(5) . . ?
C10 C9 C5 114.6(6) . . ?
C10 C9 C8 138.4(6) . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.7(5) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.9(5) . . ?
C12 C11 H11 119.1 . . ?
C4 C12 C11 114.9(6) . . ?
C4 C12 C13 106.6(5) . . ?
C11 C12 C13 137.1(6) . . ?
C12 C13 H13A 111.4 . . ?
C12 C13 H13B 111.4 . . ?
C12 C13 C14 101.9(4) . . ?
H13A C13 H13B 109.3 . . ?
C14 C13 H13A 111.4 . . ?
C14 C13 H13B 111.4 . . ?
C3 C14 C13 108.9(5) . . ?
C15 C14 C3 114.7(6) . . ?
C15 C14 C13 135.4(7) . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.4(6) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 118.7 . . ?
C15 C16 C17 122.6(5) . . ?
C17 C16 H16 118.7 . . ?
C2 C17 C16 115.1(5) . . ?
C2 C17 C18 117.8(6) . . ?
C16 C17 C18 126.3(6) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(5) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 120.4(5) . . ?
C18 C19 C24 134.6(6) . . ?
C20 C19 C24 103.8(5) . . ?
C1 C20 C19 121.6(5) . . ?
C1 C20 C21 121.7(5) . . ?
C21 C20 C19 115.4(5) . . ?
C20 C21 C22 121.2(5) . . ?
C20 C21 C23 102.4(5) . . ?
C22 C21 C23 135.1(6) . . ?
C7 C22 H22 121.5 . . ?
C21 C22 C7 117.1(5) . . ?
C21 C22 H22 121.5 . . ?
C24 C23 C21 110.7(5) . . ?
C28 C23 C21 133.9(6) . . ?
C28 C23 C24 115.2(5) . . ?
C23 C24 C19 107.2(5) . . ?
C25 C24 C19 131.8(5) . . ?
C25 C24 C23 121.0(5) . . ?
C24 C25 H25 118.8 . . ?
C26 C25 C24 122.4(6) . . ?
C26 C25 H25 118.8 . . ?
C25 C26 H26 122.5 . . ?
C27 C26 C25 115.0(6) . . ?
C27 C26 H26 122.5 . . ?
C26 C27 O2 126.8(6) . . ?
C26 C27 C28 124.7(6) . . ?
C28 C27 O2 108.5(5) . . ?
C23 C28 O1 127.1(6) . . ?
C23 C28 C27 121.6(6) . . ?
C27 C28 O1 111.2(5) . . ?
O1 C29 H29A 109.9 . . ?
O1 C29 H29B 109.9 . . ?
O2 C29 O1 109.1(5) . . ?
O2 C29 H29A 109.9 . . ?
O2 C29 H29B 109.9 . . ?
H29A C29 H29B 108.3 . . ?
C35 C30 C31 122.1(5) . . ?
C49 C30 C31 118.2(5) . . ?
C49 C30 C35 116.0(6) . . ?
C32 C31 C30 116.7(5) . . ?
C32 C31 C46 118.1(6) . . ?
C46 C31 C30 121.9(6) . . ?
C31 C32 C33 121.7(6) . . ?
C43 C32 C31 125.8(6) . . ?
C43 C32 C33 109.4(6) . . ?
C34 C33 C32 120.0(5) . . ?
C34 C33 C41 121.8(6) . . ?
C41 C33 C32 112.8(6) . . ?
C33 C34 C35 120.6(5) . . ?
C33 C34 C38 124.4(5) . . ?
C38 C34 C35 110.2(6) . . ?
C30 C35 C34 118.9(6) . . ?
C36 C35 C30 125.3(5) . . ?
C36 C35 C34 111.8(5) . . ?
C35 C36 C37 107.0(5) . . ?
C35 C36 C51 117.3(5) . . ?
C51 C36 C37 134.1(5) . . ?
C36 C37 H37A 111.2 . . ?
C36 C37 H37B 111.2 . . ?
H37A C37 H37B 109.1 . . ?
C38 C37 C36 102.7(4) . . ?
C38 C37 H37A 111.2 . . ?
C38 C37 H37B 111.2 . . ?
C34 C38 C37 107.4(5) . . ?
C39 C38 C34 114.2(6) . . ?
C39 C38 C37 136.4(6) . . ?
C38 C39 H39 119.3 . . ?
C38 C39 C40 121.4(5) . . ?
C40 C39 H39 119.3 . . ?
C39 C40 H40 119.0 . . ?
C41 C40 C39 121.9(5) . . ?
C41 C40 H40 119.0 . . ?
C33 C41 C42 105.8(5) . . ?
C40 C41 C33 116.0(6) . . ?
C40 C41 C42 136.7(6) . . ?
C41 C42 H42A 111.1 . . ?
C41 C42 H42B 111.1 . . ?
C41 C42 C43 103.1(4) . . ?
H42A C42 H42B 109.1 . . ?
C43 C42 H42A 111.1 . . ?
C43 C42 H42B 111.1 . . ?
C32 C43 C42 107.9(5) . . ?
C44 C43 C32 115.2(6) . . ?
C44 C43 C42 135.3(6) . . ?
C43 C44 H44 119.6 . . ?
C43 C44 C45 120.8(6) . . ?
C45 C44 H44 119.6 . . ?
C44 C45 H45 118.2 . . ?
C44 C45 C46 123.5(6) . . ?
C46 C45 H45 118.2 . . ?
C31 C46 C47 116.8(6) . . ?
C45 C46 C31 116.2(6) . . ?
C45 C46 C47 125.8(6) . . ?
C46 C47 H47 118.9 . . ?
C48 C47 C46 122.3(6) . . ?
C48 C47 H47 118.9 . . ?
C47 C48 C49 118.4(6) . . ?
C47 C48 C53 136.8(6) . . ?
C49 C48 C53 104.2(5) . . ?
C30 C49 C48 122.0(6) . . ?
C30 C49 C50 121.8(5) . . ?
C50 C49 C48 114.5(5) . . ?
C49 C50 C51 120.9(5) . . ?
C49 C50 C52 103.4(5) . . ?
C51 C50 C52 134.7(6) . . ?
C36 C51 H51 120.9 . . ?
C50 C51 C36 118.3(5) . . ?
C50 C51 H51 120.9 . . ?
C53 C52 C50 110.4(6) . . ?
C57 C52 C50 134.2(6) . . ?
C57 C52 C53 115.4(6) . . ?
C52 C53 C48 106.7(5) . . ?
C54 C53 C48 131.6(6) . . ?
C54 C53 C52 121.7(6) . . ?
C53 C54 H54 119.9 . . ?
C53 C54 C55 120.1(6) . . ?
C55 C54 H54 119.9 . . ?
C54 C55 H55 121.2 . . ?
C56 C55 C54 117.5(6) . . ?
C56 C55 H55 121.2 . . ?
C55 C56 O4 126.9(6) . . ?
C55 C56 C57 123.3(7) . . ?
C57 C56 O4 109.9(6) . . ?
C52 C57 O3 128.3(6) . . ?
C56 C57 O3 109.8(6) . . ?
C56 C57 C52 121.9(6) . . ?
O3 C58 H58A 110.1 . . ?
O3 C58 H58B 110.1 . . ?
O4 C58 O3 108.0(5) . . ?
O4 C58 H58A 110.1 . . ?
O4 C58 H58B 110.1 . . ?
H58A C58 H58B 108.4 . . ?
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
O1 C28 1.385(6) . ?
O1 C29 1.425(6) . ?
O2 C27 1.388(6) . ?
O2 C29 1.421(6) . ?
O3 C57 1.378(6) . ?
O3 C58 1.435(5) . ?
O4 C56 1.378(7) . ?
O4 C58 1.413(6) . ?
C1 C2 1.433(6) . ?
C1 C6 1.387(6) . ?
C1 C20 1.368(6) . ?
C2 C3 1.389(6) . ?
C2 C17 1.403(6) . ?
C3 C4 1.414(7) . ?
C3 C14 1.385(7) . ?
C4 C5 1.374(7) . ?
C4 C12 1.386(6) . ?
C5 C6 1.419(6) . ?
C5 C9 1.385(7) . ?
C6 C7 1.376(6) . ?
C7 C8 1.558(5) . ?
C7 C22 1.427(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.559(6) . ?
C9 C10 1.374(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.430(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.394(6) . ?
C12 C13 1.548(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.556(7) . ?
C14 C15 1.382(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.409(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.416(7) . ?
C17 C18 1.452(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.348(6) . ?
C19 C20 1.418(6) . ?
C19 C24 1.486(7) . ?
C20 C21 1.407(6) . ?
C21 C22 1.408(6) . ?
C21 C23 1.475(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.426(7) . ?
C23 C28 1.368(7) . ?
C24 C25 1.405(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.374(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.365(7) . ?
C27 C28 1.379(7) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.418(7) . ?
C30 C35 1.395(6) . ?
C30 C49 1.375(6) . ?
C31 C32 1.402(6) . ?
C31 C46 1.406(7) . ?
C32 C33 1.422(6) . ?
C32 C43 1.390(7) . ?
C33 C34 1.359(6) . ?
C33 C41 1.389(7) . ?
C34 C35 1.418(6) . ?
C34 C38 1.401(7) . ?
C35 C36 1.387(7) . ?
C36 C37 1.551(6) . ?
C36 C51 1.426(6) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C38 1.547(6) . ?
C38 C39 1.386(7) . ?
C39 H39 0.9300 . ?
C39 C40 1.436(7) . ?
C40 H40 0.9300 . ?
C40 C41 1.370(7) . ?
C41 C42 1.547(7) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C43 1.549(6) . ?
C43 C44 1.381(7) . ?
C44 H44 0.9300 . ?
C44 C45 1.398(7) . ?
C45 H45 0.9300 . ?
C45 C46 1.404(7) . ?
C46 C47 1.447(7) . ?
C47 H47 0.9300 . ?
C47 C48 1.354(7) . ?
C48 C49 1.435(6) . ?
C48 C53 1.491(7) . ?
C49 C50 1.401(7) . ?
C50 C51 1.407(6) . ?
C50 C52 1.478(7) . ?
C51 H51 0.9300 . ?
C52 C53 1.443(7) . ?
C52 C57 1.370(7) . ?
C53 C54 1.383(6) . ?
C54 H54 0.9300 . ?
C54 C55 1.391(7) . ?
C55 H55 0.9300 . ?
C55 C56 1.366(7) . ?
C56 C57 1.369(7) . ?
C58 H58A 0.9700 . ?
C58 H58B 0.9700 . ?
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
O2 C27 C28 O1 -0.4(7) . . . . ?
O2 C27 C28 C23 176.8(5) . . . . ?
O4 C56 C57 O3 -1.1(7) . . . . ?
O4 C56 C57 C52 179.7(6) . . . . ?
C1 C2 C3 C4 -2.9(8) . . . . ?
C1 C2 C3 C14 -158.5(5) . . . . ?
C1 C2 C17 C16 166.4(5) . . . . ?
C1 C2 C17 C18 -4.2(7) . . . . ?
C1 C6 C7 C8 -161.9(5) . . . . ?
C1 C6 C7 C22 4.9(8) . . . . ?
C1 C20 C21 C22 5.4(8) . . . . ?
C1 C20 C21 C23 174.3(5) . . . . ?
C2 C1 C6 C5 -2.7(8) . . . . ?
C2 C1 C6 C7 155.1(5) . . . . ?
C2 C1 C20 C19 5.3(8) . . . . ?
C2 C1 C20 C21 -161.0(5) . . . . ?
C2 C3 C4 C5 1.5(8) . . . . ?
C2 C3 C4 C12 -157.0(5) . . . . ?
C2 C3 C14 C13 161.2(5) . . . . ?
C2 C3 C14 C15 -9.5(9) . . . . ?
C2 C17 C18 C19 5.1(8) . . . . ?
C3 C2 C17 C16 5.7(7) . . . . ?
C3 C2 C17 C18 -164.9(5) . . . . ?
C3 C4 C5 C6 -0.5(8) . . . . ?
C3 C4 C5 C9 -153.4(6) . . . . ?
C3 C4 C12 C11 162.5(5) . . . . ?
C3 C4 C12 C13 -6.2(6) . . . . ?
C3 C14 C15 C16 6.9(8) . . . . ?
C4 C3 C14 C13 3.0(6) . . . . ?
C4 C3 C14 C15 -167.7(5) . . . . ?
C4 C5 C6 C1 1.1(8) . . . . ?
C4 C5 C6 C7 -159.6(5) . . . . ?
C4 C5 C9 C8 162.1(5) . . . . ?
C4 C5 C9 C10 -8.4(8) . . . . ?
C4 C12 C13 C14 7.2(6) . . . . ?
C5 C4 C12 C11 4.3(8) . . . . ?
C5 C4 C12 C13 -164.4(5) . . . . ?
C5 C6 C7 C8 -2.3(6) . . . . ?
C5 C6 C7 C22 164.5(5) . . . . ?
C5 C9 C10 C11 6.3(8) . . . . ?
C6 C1 C2 C3 3.5(8) . . . . ?
C6 C1 C2 C17 -157.8(5) . . . . ?
C6 C1 C20 C19 163.5(5) . . . . ?
C6 C1 C20 C21 -2.9(8) . . . . ?
C6 C5 C9 C8 7.7(6) . . . . ?
C6 C5 C9 C10 -162.8(5) . . . . ?
C6 C7 C8 C9 6.5(5) . . . . ?
C6 C7 C22 C21 -2.2(7) . . . . ?
C7 C8 C9 C5 -8.5(6) . . . . ?
C7 C8 C9 C10 158.5(7) . . . . ?
C8 C7 C22 C21 160.5(5) . . . . ?
C8 C9 C10 C11 -159.9(6) . . . . ?
C9 C5 C6 C1 157.1(5) . . . . ?
C9 C5 C6 C7 -3.6(7) . . . . ?
C9 C10 C11 C12 0.8(9) . . . . ?
C10 C11 C12 C4 -6.1(8) . . . . ?
C10 C11 C12 C13 157.9(6) . . . . ?
C11 C12 C13 C14 -157.6(6) . . . . ?
C12 C4 C5 C6 156.1(5) . . . . ?
C12 C4 C5 C9 3.2(9) . . . . ?
C12 C13 C14 C3 -6.2(6) . . . . ?
C12 C13 C14 C15 161.6(6) . . . . ?
C13 C14 C15 C16 -160.4(6) . . . . ?
C14 C3 C4 C5 160.6(5) . . . . ?
C14 C3 C4 C12 2.1(7) . . . . ?
C14 C15 C16 C17 1.5(9) . . . . ?
C15 C16 C17 C2 -8.0(8) . . . . ?
C15 C16 C17 C18 161.7(5) . . . . ?
C16 C17 C18 C19 -164.4(5) . . . . ?
C17 C2 C3 C4 158.7(5) . . . . ?
C17 C2 C3 C14 3.1(9) . . . . ?
C17 C18 C19 C20 -0.8(8) . . . . ?
C17 C18 C19 C24 164.4(5) . . . . ?
C18 C19 C20 C1 -4.5(8) . . . . ?
C18 C19 C20 C21 162.6(5) . . . . ?
C18 C19 C24 C23 -163.9(6) . . . . ?
C18 C19 C24 C25 14.2(11) . . . . ?
C19 C20 C21 C22 -161.7(5) . . . . ?
C19 C20 C21 C23 7.1(6) . . . . ?
C19 C24 C25 C26 -178.9(5) . . . . ?
C20 C1 C2 C3 160.4(5) . . . . ?
C20 C1 C2 C17 -0.9(8) . . . . ?
C20 C1 C6 C5 -160.1(5) . . . . ?
C20 C1 C6 C7 -2.3(8) . . . . ?
C20 C19 C24 C23 3.1(6) . . . . ?
C20 C19 C24 C25 -178.8(6) . . . . ?
C20 C21 C22 C7 -2.7(8) . . . . ?
C20 C21 C23 C24 -4.7(6) . . . . ?
C20 C21 C23 C28 -179.9(6) . . . . ?
C21 C23 C24 C19 1.1(6) . . . . ?
C21 C23 C24 C25 -177.3(5) . . . . ?
C21 C23 C28 O1 -4.9(11) . . . . ?
C21 C23 C28 C27 178.4(6) . . . . ?
C22 C7 C8 C9 -157.5(6) . . . . ?
C22 C21 C23 C24 161.7(6) . . . . ?
C22 C21 C23 C28 -13.4(11) . . . . ?
C23 C21 C22 C7 -167.2(6) . . . . ?
C23 C24 C25 C26 -1.1(8) . . . . ?
C24 C19 C20 C1 -173.8(5) . . . . ?
C24 C19 C20 C21 -6.6(6) . . . . ?
C24 C23 C28 O1 -179.8(5) . . . . ?
C24 C23 C28 C27 3.4(8) . . . . ?
C24 C25 C26 C27 1.0(8) . . . . ?
C25 C26 C27 O2 -179.3(5) . . . . ?
C25 C26 C27 C28 1.4(9) . . . . ?
C26 C27 C28 O1 179.0(5) . . . . ?
C26 C27 C28 C23 -3.8(10) . . . . ?
C27 O2 C29 O1 -15.7(6) . . . . ?
C28 O1 C29 O2 15.2(6) . . . . ?
C28 C23 C24 C19 177.2(5) . . . . ?
C28 C23 C24 C25 -1.2(8) . . . . ?
C29 O1 C28 C23 173.9(6) . . . . ?
C29 O1 C28 C27 -9.1(6) . . . . ?
C29 O2 C27 C26 -169.6(6) . . . . ?
C29 O2 C27 C28 9.8(7) . . . . ?
C30 C31 C32 C33 0.2(8) . . . . ?
C30 C31 C32 C43 -157.5(6) . . . . ?
C30 C31 C46 C45 162.8(5) . . . . ?
C30 C31 C46 C47 -5.2(8) . . . . ?
C30 C35 C36 C37 -161.6(5) . . . . ?
C30 C35 C36 C51 6.2(9) . . . . ?
C30 C49 C50 C51 4.9(9) . . . . ?
C30 C49 C50 C52 175.2(5) . . . . ?
C31 C30 C35 C34 -1.7(8) . . . . ?
C31 C30 C35 C36 154.0(6) . . . . ?
C31 C30 C49 C48 4.1(8) . . . . ?
C31 C30 C49 C50 -160.6(5) . . . . ?
C31 C32 C33 C34 -1.4(8) . . . . ?
C31 C32 C33 C41 -155.8(5) . . . . ?
C31 C32 C43 C42 161.5(5) . . . . ?
C31 C32 C43 C44 -6.4(9) . . . . ?
C31 C46 C47 C48 6.5(9) . . . . ?
C32 C31 C46 C45 4.1(8) . . . . ?
C32 C31 C46 C47 -163.9(5) . . . . ?
C32 C33 C34 C35 1.0(8) . . . . ?
C32 C33 C34 C38 -152.1(5) . . . . ?
C32 C33 C41 C40 159.1(5) . . . . ?
C32 C33 C41 C42 -9.3(6) . . . . ?
C32 C43 C44 C45 3.9(8) . . . . ?
C33 C32 C43 C42 1.6(6) . . . . ?
C33 C32 C43 C44 -166.4(5) . . . . ?
C33 C34 C35 C30 0.5(8) . . . . ?
C33 C34 C35 C36 -158.3(5) . . . . ?
C33 C34 C38 C37 162.6(5) . . . . ?
C33 C34 C38 C39 -3.9(8) . . . . ?
C33 C41 C42 C43 9.4(6) . . . . ?
C34 C33 C41 C40 5.1(8) . . . . ?
C34 C33 C41 C42 -163.2(5) . . . . ?
C34 C35 C36 C37 -4.4(6) . . . . ?
C34 C35 C36 C51 163.4(5) . . . . ?
C34 C38 C39 C40 2.6(8) . . . . ?
C35 C30 C31 C32 1.4(8) . . . . ?
C35 C30 C31 C46 -157.7(6) . . . . ?
C35 C30 C49 C48 163.3(5) . . . . ?
C35 C30 C49 C50 -1.5(8) . . . . ?
C35 C34 C38 C37 7.1(6) . . . . ?
C35 C34 C38 C39 -159.4(5) . . . . ?
C35 C36 C37 C38 8.1(6) . . . . ?
C35 C36 C51 C50 -2.5(8) . . . . ?
C36 C37 C38 C34 -9.2(6) . . . . ?
C36 C37 C38 C39 152.9(7) . . . . ?
C37 C36 C51 C50 161.2(6) . . . . ?
C37 C38 C39 C40 -158.6(6) . . . . ?
C38 C34 C35 C30 157.0(5) . . . . ?
C38 C34 C35 C36 -1.8(7) . . . . ?
C38 C39 C40 C41 2.6(9) . . . . ?
C39 C40 C41 C33 -6.3(8) . . . . ?
C39 C40 C41 C42 157.2(6) . . . . ?
C40 C41 C42 C43 -155.2(7) . . . . ?
C41 C33 C34 C35 153.2(5) . . . . ?
C41 C33 C34 C38 0.0(9) . . . . ?
C41 C42 C43 C32 -6.7(6) . . . . ?
C41 C42 C43 C44 157.7(6) . . . . ?
C42 C43 C44 C45 -159.7(6) . . . . ?
C43 C32 C33 C34 159.6(5) . . . . ?
C43 C32 C33 C41 5.1(7) . . . . ?
C43 C44 C45 C46 2.4(9) . . . . ?
C44 C45 C46 C31 -6.5(9) . . . . ?
C44 C45 C46 C47 160.3(6) . . . . ?
C45 C46 C47 C48 -160.2(6) . . . . ?
C46 C31 C32 C33 160.0(5) . . . . ?
C46 C31 C32 C43 2.3(9) . . . . ?
C46 C47 C48 C49 -2.6(9) . . . . ?
C46 C47 C48 C53 166.7(6) . . . . ?
C47 C48 C49 C30 -2.9(9) . . . . ?
C47 C48 C49 C50 162.9(5) . . . . ?
C47 C48 C53 C52 -164.9(7) . . . . ?
C47 C48 C53 C54 14.4(12) . . . . ?
C48 C49 C50 C51 -160.9(5) . . . . ?
C48 C49 C50 C52 9.4(6) . . . . ?
C48 C53 C54 C55 178.1(6) . . . . ?
C49 C30 C31 C32 159.2(5) . . . . ?
C49 C30 C31 C46 0.1(8) . . . . ?
C49 C30 C35 C34 -160.0(5) . . . . ?
C49 C30 C35 C36 -4.2(9) . . . . ?
C49 C48 C53 C52 5.4(6) . . . . ?
C49 C48 C53 C54 -175.3(6) . . . . ?
C49 C50 C51 C36 -2.8(8) . . . . ?
C49 C50 C52 C53 -5.4(6) . . . . ?
C49 C50 C52 C57 172.1(7) . . . . ?
C50 C52 C53 C48 -0.1(6) . . . . ?
C50 C52 C53 C54 -179.5(5) . . . . ?
C50 C52 C57 O3 2.1(11) . . . . ?
C50 C52 C57 C56 -178.9(6) . . . . ?
C51 C36 C37 C38 -156.8(6) . . . . ?
C51 C50 C52 C53 162.9(6) . . . . ?
C51 C50 C52 C57 -19.7(11) . . . . ?
C52 C50 C51 C36 -169.4(6) . . . . ?
C52 C53 C54 C55 -2.7(9) . . . . ?
C53 C48 C49 C30 -175.4(5) . . . . ?
C53 C48 C49 C50 -9.6(7) . . . . ?
C53 C52 C57 O3 179.5(5) . . . . ?
C53 C52 C57 C56 -1.5(9) . . . . ?
C53 C54 C55 C56 1.6(9) . . . . ?
C54 C55 C56 O4 -179.5(6) . . . . ?
C54 C55 C56 C57 -0.5(10) . . . . ?
C55 C56 C57 O3 179.8(6) . . . . ?
C55 C56 C57 C52 0.6(10) . . . . ?
C56 O4 C58 O3 2.6(7) . . . . ?
C57 O3 C58 O4 -3.2(7) . . . . ?
C57 C52 C53 C48 -178.1(5) . . . . ?
C57 C52 C53 C54 2.5(8) . . . . ?
C58 O3 C57 C52 -178.2(6) . . . . ?
C58 O3 C57 C56 2.7(7) . . . . ?
C58 O4 C56 C55 178.1(7) . . . . ?
C58 O4 C56 C57 -1.0(7) . . . . ?
