#------------------------------------------------------------------------------
#$Date: 2020-08-06 17:43:52 +0300 (Thu, 06 Aug 2020) $
#$Revision: 255094 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157544.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_7157544
loop_
_publ_author_name
'Yang, Yong'
'Nanjo, Yuki'
'Isobe, Hiroyuki'
'Sato, Sota'
_publ_section_title
;
 Synthesis and stereoisomerism of [n]cyclo-2,9-phenanthrenylene congeners
 possessing alternating E/Z- and R/S-biaryl linkages.
;
_journal_issue                   26
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4949
_journal_page_last               4955
_journal_paper_doi               10.1039/d0ob01064b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C56 H32'
_chemical_formula_sum            'C56 H32'
_chemical_formula_weight         704.81
_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
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-01-11 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.232(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6620(16)
_cell_length_b                   15.9490(11)
_cell_length_c                   14.374(2)
_cell_measurement_reflns_used    14363
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.210
_cell_measurement_theta_min      2.054
_cell_volume                     1733.8(5)
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       'SPring-8 BSS'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'PAD Pilatus3 6M (Dectris)'
_diffrn_measurement_method       'oscillation method, ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.760
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0084
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            40355
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        27.129
_diffrn_reflns_theta_max         27.210
_diffrn_reflns_theta_min         2.054
_diffrn_source                   'SPring-8 BL38B1 bending magnet beamline'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform and acetonitrile'
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0436
_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)+(0.0606P)²+0.8747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2983
_reflns_number_total             3157
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01064b2.cif
_cod_data_source_block           p21c
_cod_depositor_comments
'Adding full bibliography for 7157543--7157545.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157544
_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.
;
_shelx_estimated_absorpt_t_min   0.995
_shelx_estimated_absorpt_t_max   0.998
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
C1 C -0.23085(19) 0.62055(9) 0.66822(10) 0.0297(3) Uani 1 1 d . . . . .
H1 H -0.291730 0.627059 0.605660 0.036 Uiso 1 1 calc R U . . .
C2 C -0.29516(19) 0.56499(10) 0.72581(10) 0.0290(3) Uani 1 1 d . . . . .
C3 C -0.23270(19) 0.57162(9) 0.82682(10) 0.0293(3) Uani 1 1 d . . . . .
C4 C -0.3062(2) 0.52416(10) 0.89351(11) 0.0330(3) Uani 1 1 d . . . . .
H4 H -0.394862 0.483800 0.872298 0.040 Uiso 1 1 calc R U . . .
C5 C -0.2521(2) 0.53503(10) 0.98911(11) 0.0354(4) Uani 1 1 d . . . . .
H5 H -0.306406 0.503919 1.033026 0.043 Uiso 1 1 calc R U . . .
C6 C -0.1174(2) 0.59181(10) 1.02091(10) 0.0353(4) Uani 1 1 d . . . . .
H6 H -0.082222 0.600605 1.086607 0.042 Uiso 1 1 calc R U . . .
C7 C -0.0357(2) 0.63497(10) 0.95757(10) 0.0319(3) Uani 1 1 d . . . . .
H7 H 0.059747 0.671406 0.980322 0.038 Uiso 1 1 calc R U . . .
C8 C -0.0894(2) 0.62672(9) 0.85976(10) 0.0295(3) Uani 1 1 d . . . . .
C9 C 0.0037(2) 0.66947(9) 0.79280(10) 0.0290(3) Uani 1 1 d . . . . .
C10 C 0.1752(2) 0.70325(10) 0.81460(10) 0.0312(3) Uani 1 1 d . . . . .
H10 H 0.226494 0.710700 0.878747 0.037 Uiso 1 1 calc R U . . .
C11 C 0.2708(2) 0.72589(10) 0.74423(10) 0.0316(3) Uani 1 1 d . . . . .
H11 H 0.387932 0.746522 0.760799 0.038 Uiso 1 1 calc R U . . .
C12 C 0.1956(2) 0.71856(9) 0.64847(10) 0.0303(3) Uani 1 1 d . . . . .
C13 C 0.0180(2) 0.69839(9) 0.62809(10) 0.0302(3) Uani 1 1 d . . . . .
H13 H -0.041766 0.704319 0.565209 0.036 Uiso 1 1 calc R U . . .
C14 C -0.07621(19) 0.66955(9) 0.69737(10) 0.0291(3) Uani 1 1 d . . . . .
C15 C 0.2551(2) 0.64113(10) 0.51270(10) 0.0322(3) Uani 1 1 d . . . . .
H15 H 0.151790 0.610534 0.520002 0.039 Uiso 1 1 calc R U . . .
C16 C 0.3026(2) 0.70787(10) 0.57092(10) 0.0309(3) Uani 1 1 d . . . . .
C17 C 0.4526(2) 0.75465(10) 0.55540(10) 0.0321(3) Uani 1 1 d . . . . .
H17 H 0.486876 0.802854 0.592711 0.039 Uiso 1 1 calc R U . . .
C18 C 0.5496(2) 0.73077(10) 0.48636(10) 0.0318(3) Uani 1 1 d . . . . .
H18 H 0.648091 0.763857 0.476439 0.038 Uiso 1 1 calc R U . . .
C19 C 0.50625(19) 0.65834(9) 0.43001(10) 0.0291(3) Uani 1 1 d . . . . .
C20 C 0.61198(19) 0.62148(10) 0.36482(10) 0.0296(3) Uani 1 1 d . . . . .
C21 C 0.7747(2) 0.65609(10) 0.35123(11) 0.0329(3) Uani 1 1 d . . . . .
H21 H 0.811125 0.708206 0.379972 0.039 Uiso 1 1 calc R U . . .
C22 C 0.8823(2) 0.61635(11) 0.29741(11) 0.0361(4) Uani 1 1 d . . . . .
H22 H 0.990565 0.641602 0.288261 0.043 Uiso 1 1 calc R U . . .
C23 C 0.8329(2) 0.53878(11) 0.25601(11) 0.0351(4) Uani 1 1 d . . . . .
H23 H 0.910949 0.509727 0.222171 0.042 Uiso 1 1 calc R U . . .
C24 C 0.6731(2) 0.50490(10) 0.26418(10) 0.0321(3) Uani 1 1 d . . . . .
H24 H 0.639682 0.452787 0.234563 0.039 Uiso 1 1 calc R U . . .
C25 C 0.55581(19) 0.54567(9) 0.31582(10) 0.0294(3) Uani 1 1 d . . . . .
C26 C 0.38541(19) 0.50981(10) 0.32381(10) 0.0293(3) Uani 1 1 d . . . . .
C27 C 0.2926(2) 0.54494(10) 0.38663(10) 0.0313(3) Uani 1 1 d . . . . .
H27 H 0.181922 0.520832 0.393385 0.038 Uiso 1 1 calc R U . . .
C28 C 0.3517(2) 0.61579(10) 0.44282(10) 0.0303(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0038 0.0019 '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 C14 122.99(13) . . ?
C2 C1 H1 118.5 . . ?
C14 C1 H1 118.5 . . ?
C1 C2 C3 117.81(14) . . ?
C1 C2 C26 114.43(13) . 3_566 ?
C3 C2 C26 125.71(13) . 3_566 ?
C4 C3 C8 118.41(13) . . ?
C4 C3 C2 122.40(14) . . ?
C8 C3 C2 119.18(13) . . ?
C5 C4 C3 121.39(15) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.75(14) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.11(14) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 121.69(15) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C3 118.42(14) . . ?
C7 C8 C9 121.38(14) . . ?
C3 C8 C9 120.12(13) . . ?
C10 C9 C14 117.42(13) . . ?
C10 C9 C8 124.81(13) . . ?
C14 C9 C8 117.45(13) . . ?
C11 C10 C9 121.31(14) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.63(14) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 117.39(13) . . ?
C13 C12 C16 117.00(13) . . ?
C11 C12 C16 123.41(14) . . ?
C12 C13 C14 121.89(13) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C9 120.01(14) . . ?
C13 C14 C1 118.09(13) . . ?
C9 C14 C1 119.77(13) . . ?
C16 C15 C28 123.00(14) . . ?
C16 C15 H15 118.5 . . ?
C28 C15 H15 118.5 . . ?
C15 C16 C17 117.17(14) . . ?
C15 C16 C12 114.91(14) . . ?
C17 C16 C12 127.76(14) . . ?
C18 C17 C16 120.65(14) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 121.94(14) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C28 C19 C18 116.38(13) . . ?
C28 C19 C20 117.22(13) . . ?
C18 C19 C20 126.29(14) . . ?
C21 C20 C25 117.84(14) . . ?
C21 C20 C19 121.88(14) . . ?
C25 C20 C19 120.21(13) . . ?
C22 C21 C20 121.56(15) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 120.14(15) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.04(15) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 121.30(15) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C24 C25 C20 118.78(14) . . ?
C24 C25 C26 121.19(14) . . ?
C20 C25 C26 119.94(13) . . ?
C27 C26 C25 117.75(14) . . ?
C27 C26 C2 113.19(13) . 3_566 ?
C25 C26 C2 129.01(13) . 3_566 ?
C26 C27 C28 123.60(14) . . ?
C26 C27 H27 118.2 . . ?
C28 C27 H27 118.2 . . ?
C15 C28 C19 120.63(14) . . ?
C15 C28 C27 118.72(14) . . ?
C19 C28 C27 120.64(14) . . ?
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 1.358(2) . ?
C1 C14 1.425(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.458(2) . ?
C2 C26 1.501(2) 3_566 ?
C3 C4 1.408(2) . ?
C3 C8 1.426(2) . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.370(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.406(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.457(2) . ?
C9 C10 1.408(2) . ?
C9 C14 1.410(2) . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.409(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 C16 1.496(2) . ?
C13 C14 1.398(2) . ?
C13 H13 0.9500 . ?
C15 C16 1.367(2) . ?
C15 C28 1.400(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.417(2) . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.419(2) . ?
C18 H18 0.9500 . ?
C19 C28 1.402(2) . ?
C19 C20 1.457(2) . ?
C20 C21 1.406(2) . ?
C20 C25 1.430(2) . ?
C21 C22 1.373(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.398(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.361(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.412(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.447(2) . ?
C26 C27 1.357(2) . ?
C27 C28 1.420(2) . ?
C27 H27 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
C14 C1 C2 C3 16.5(2) . . . . ?
C14 C1 C2 C26 -148.11(14) . . . 3_566 ?
C1 C2 C3 C4 172.13(14) . . . . ?
C26 C2 C3 C4 -25.1(2) 3_566 . . . ?
C1 C2 C3 C8 -9.3(2) . . . . ?
C26 C2 C3 C8 153.48(14) 3_566 . . . ?
C8 C3 C4 C5 5.2(2) . . . . ?
C2 C3 C4 C5 -176.14(14) . . . . ?
C3 C4 C5 C6 -2.4(2) . . . . ?
C4 C5 C6 C7 -1.8(2) . . . . ?
C5 C6 C7 C8 3.1(2) . . . . ?
C6 C7 C8 C3 -0.1(2) . . . . ?
C6 C7 C8 C9 -176.83(14) . . . . ?
C4 C3 C8 C7 -3.9(2) . . . . ?
C2 C3 C8 C7 177.40(13) . . . . ?
C4 C3 C8 C9 172.82(13) . . . . ?
C2 C3 C8 C9 -5.8(2) . . . . ?
C7 C8 C9 C10 17.4(2) . . . . ?
C3 C8 C9 C10 -159.24(14) . . . . ?
C7 C8 C9 C14 -169.34(14) . . . . ?
C3 C8 C9 C14 14.0(2) . . . . ?
C14 C9 C10 C11 -8.0(2) . . . . ?
C8 C9 C10 C11 165.23(14) . . . . ?
C9 C10 C11 C12 2.4(2) . . . . ?
C10 C11 C12 C13 8.0(2) . . . . ?
C10 C11 C12 C16 -154.64(15) . . . . ?
C11 C12 C13 C14 -12.9(2) . . . . ?
C16 C12 C13 C14 150.86(14) . . . . ?
C12 C13 C14 C9 7.4(2) . . . . ?
C12 C13 C14 C1 -156.02(14) . . . . ?
C10 C9 C14 C13 3.3(2) . . . . ?
C8 C9 C14 C13 -170.50(13) . . . . ?
C10 C9 C14 C1 166.35(14) . . . . ?
C8 C9 C14 C1 -7.4(2) . . . . ?
C2 C1 C14 C13 155.21(15) . . . . ?
C2 C1 C14 C9 -8.2(2) . . . . ?
C28 C15 C16 C17 2.9(2) . . . . ?
C28 C15 C16 C12 -172.83(14) . . . . ?
C13 C12 C16 C15 -35.5(2) . . . . ?
C11 C12 C16 C15 127.20(16) . . . . ?
C13 C12 C16 C17 149.34(15) . . . . ?
C11 C12 C16 C17 -48.0(2) . . . . ?
C15 C16 C17 C18 -2.6(2) . . . . ?
C12 C16 C17 C18 172.52(15) . . . . ?
C16 C17 C18 C19 -1.3(2) . . . . ?
C17 C18 C19 C28 4.8(2) . . . . ?
C17 C18 C19 C20 -171.22(14) . . . . ?
C28 C19 C20 C21 -175.96(14) . . . . ?
C18 C19 C20 C21 0.0(2) . . . . ?
C28 C19 C20 C25 0.9(2) . . . . ?
C18 C19 C20 C25 176.92(14) . . . . ?
C25 C20 C21 C22 -3.9(2) . . . . ?
C19 C20 C21 C22 173.08(14) . . . . ?
C20 C21 C22 C23 -1.3(2) . . . . ?
C21 C22 C23 C24 4.0(2) . . . . ?
C22 C23 C24 C25 -1.4(2) . . . . ?
C23 C24 C25 C20 -3.8(2) . . . . ?
C23 C24 C25 C26 179.54(14) . . . . ?
C21 C20 C25 C24 6.3(2) . . . . ?
C19 C20 C25 C24 -170.72(13) . . . . ?
C21 C20 C25 C26 -176.97(13) . . . . ?
C19 C20 C25 C26 6.0(2) . . . . ?
C24 C25 C26 C27 169.43(14) . . . . ?
C20 C25 C26 C27 -7.2(2) . . . . ?
C24 C25 C26 C2 -7.9(2) . . . 3_566 ?
C20 C25 C26 C2 175.43(13) . . . 3_566 ?
C25 C26 C27 C28 1.6(2) . . . . ?
C2 C26 C27 C28 179.31(13) 3_566 . . . ?
C16 C15 C28 C19 0.7(2) . . . . ?
C16 C15 C28 C27 179.26(14) . . . . ?
C18 C19 C28 C15 -4.5(2) . . . . ?
C20 C19 C28 C15 171.90(13) . . . . ?
C18 C19 C28 C27 177.00(13) . . . . ?
C20 C19 C28 C27 -6.6(2) . . . . ?
C26 C27 C28 C15 -172.96(14) . . . . ?
C26 C27 C28 C19 5.6(2) . . . . ?
