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#$Date: 2020-10-23 01:57:29 +0300 (Fri, 23 Oct 2020) $
#$Revision: 258563 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/53/4135311.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_4135311
loop_
_publ_author_name
'Lu, Hua'
'Nakamuro, Takayuki'
'Yamashita, Keitaro'
'Yanagisawa, Haruaki'
'Nureki, Osamu'
'Kikkawa, Masahide'
'Gao, Han'
'Tian, Jiangwei'
'Shang, Rui'
'Nakamura, Eiichi'
_publ_section_title
;
 B/N-Doped p-Arylenevinylene Chromophores: Synthesis, Properties, and
 Microcrystal Electron Crystallographic Study
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c10337
_journal_year                    2020
_chemical_formula_moiety         'C38 H28 B N'
_chemical_formula_sum            'C38 H28 B N'
_chemical_formula_weight         509.42
_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   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 102.335(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6701(6)
_cell_length_b                   15.1062(9)
_cell_length_c                   8.7738(6)
_cell_measurement_reflns_used    3715
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      65.13
_cell_measurement_theta_min      2.11
_cell_volume                     1381.56(15)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10594
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         89.033
_diffrn_reflns_theta_min         4.241
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3145
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0487
_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)+(0.05P)²+0.33P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1332
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1849
_reflns_number_total             3145
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c10337_si_002.cif
_cod_data_source_block           cu190517
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4135311
_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   0.925
_shelx_estimated_absorpt_t_max   0.939
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
N1 N 0.56053(13) 0.61789(9) 0.64869(16) 0.0376(3) Uani 0.5 1 d . . P . .
C1 C 0.56053(13) 0.61789(9) 0.64869(16) 0.0376(3) Uani 0.5 1 d . . P . .
B1 B 0.33972(14) 0.45542(10) 0.37971(19) 0.0363(4) Uani 0.5 1 d . . P . .
C2 C 0.33972(14) 0.45542(10) 0.37971(19) 0.0363(4) Uani 0.5 1 d . . P . .
C3 C 0.43984(15) 0.51517(10) 0.48810(18) 0.0399(3) Uani 1 1 d . . . . .
C4 C 0.43858(15) 0.59862(10) 0.57223(18) 0.0399(3) Uani 1 1 d . . . . .
C5 C 0.33706(15) 0.65537(10) 0.58328(18) 0.0399(3) Uani 1 1 d . U . . .
H5 H 0.252122 0.642771 0.528509 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3630(2) 0.72984(12) 0.6753(2) 0.0596(4) Uani 1 1 d . U . . .
H6 H 0.295275 0.768654 0.685547 0.071 Uiso 1 1 calc R U . . .
C7 C 0.48548(19) 0.74809(12) 0.7516(2) 0.0596(4) Uani 1 1 d . . . . .
H7 H 0.502171 0.799633 0.814733 0.071 Uiso 1 1 calc R U . . .
C8 C 0.5864(2) 0.69229(11) 0.7384(2) 0.0545(5) Uani 1 1 d . . . . .
C9 C 0.28022(14) 0.50561(9) 0.22223(18) 0.0355(4) Uani 1 1 d . . . . .
C10 C 0.15678(15) 0.54126(11) 0.1910(2) 0.0482(4) Uani 1 1 d . . . . .
H10 H 0.104815 0.534309 0.265661 0.058 Uiso 1 1 calc R U . . .
C11 C 0.10866(17) 0.58603(12) 0.0554(2) 0.0553(5) Uani 1 1 d . . . . .
H11 H 0.023626 0.608565 0.036857 0.066 Uiso 1 1 calc R U . . .
C12 C 0.18096(19) 0.59873(12) -0.0533(2) 0.0596(5) Uani 1 1 d . U . . .
H12 H 0.146726 0.628622 -0.148343 0.072 Uiso 1 1 calc R U . . .
C13 C 0.30493(19) 0.56715(12) -0.0220(2) 0.0576(5) Uani 1 1 d . U . . .
H13 H 0.358071 0.577353 -0.094401 0.069 Uiso 1 1 calc R U . . .
C14 C 0.35201(17) 0.52145(12) 0.1117(2) 0.0489(4) Uani 1 1 d . . . . .
H14 H 0.437429 0.499684 0.129503 0.059 Uiso 1 1 calc R U . . .
C15 C 0.23806(14) 0.41201(10) 0.46322(18) 0.0387(4) Uani 1 1 d . . . . .
C16 C 0.24589(17) 0.41852(12) 0.6215(2) 0.0533(5) Uani 1 1 d . . . . .
H16 H 0.313999 0.452026 0.682168 0.064 Uiso 1 1 calc R U . . .
C17 C 0.1588(2) 0.37837(14) 0.6962(2) 0.0634(5) Uani 1 1 d . U . . .
H17 H 0.166959 0.384812 0.805613 0.076 Uiso 1 1 calc R U . . .
C18 C 0.06066(19) 0.32912(13) 0.6098(2) 0.0619(5) Uani 1 1 d . U . . .
H18 H 0.000677 0.300660 0.659372 0.074 Uiso 1 1 calc R U . . .
C19 C 0.04957(18) 0.32124(13) 0.4534(2) 0.0581(5) Uani 1 1 d . . . . .
H19 H -0.018636 0.287392 0.393754 0.070 Uiso 1 1 calc R U . . .
C20 C 0.13670(16) 0.36205(11) 0.3802(2) 0.0489(4) Uani 1 1 d . . . . .
H20 H 0.127077 0.355794 0.270581 0.059 Uiso 1 1 calc R U . . .
H8 H 0.683(2) 0.7044(15) 0.800(2) 0.085(7) Uiso 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 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C4 N1 C8 120.93(14) . . ?
C4 N1 B1 112.00(12) . 3_666 ?
C8 N1 B1 127.07(14) . 3_666 ?
C3 B1 C15 114.06(13) . . ?
C3 B1 C9 110.48(12) . . ?
C15 B1 C9 114.65(12) . . ?
C3 B1 N1 95.99(11) . 3_666 ?
C15 B1 N1 109.44(12) . 3_666 ?
C9 B1 N1 110.67(12) . 3_666 ?
C3 C3 C4 109.19(19) 3_666 . ?
C3 C3 B1 114.03(18) 3_666 . ?
C4 C3 B1 136.77(13) . . ?
N1 C4 C5 120.44(15) . . ?
N1 C4 C3 108.79(13) . . ?
C5 C4 C3 130.77(15) . . ?
C6 C5 C4 118.59(16) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C7 C6 C5 120.32(16) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.94(18) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
N1 C8 C7 118.78(19) . . ?
N1 C8 H8 119.1(12) . . ?
C7 C8 H8 122.0(12) . . ?
C14 C9 C10 115.97(15) . . ?
C14 C9 B1 121.12(13) . . ?
C10 C9 B1 122.77(13) . . ?
C11 C10 C9 121.61(16) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 120.96(17) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 118.36(17) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 120.61(17) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C9 122.41(16) . . ?
C13 C14 H14 118.8 . . ?
C9 C14 H14 118.8 . . ?
C16 C15 C20 116.10(15) . . ?
C16 C15 B1 122.67(15) . . ?
C20 C15 B1 121.20(14) . . ?
C15 C16 C17 122.93(18) . . ?
C15 C16 H16 118.5 . . ?
C17 C16 H16 118.5 . . ?
C18 C17 C16 119.01(18) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C19 C18 C17 119.82(17) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.57(18) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 121.57(17) . . ?
C19 C20 H20 119.2 . . ?
C15 C20 H20 119.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.362(2) . ?
N1 C8 1.366(2) . ?
N1 B1 1.592(2) 3_666 ?
B1 C3 1.558(2) . ?
B1 C15 1.576(2) . ?
B1 C9 1.585(2) . ?
C3 C3 1.337(3) 3_666 ?
C3 C4 1.462(2) . ?
C4 C5 1.401(2) . ?
C5 C6 1.378(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.363(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(2) . ?
C7 H7 0.9500 . ?
C8 H8 1.07(2) . ?
C9 C14 1.379(2) . ?
C9 C10 1.395(2) . ?
C10 C11 1.370(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.362(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.361(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.377(2) . ?
C15 C20 1.390(2) . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.357(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
