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#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/51/7235198.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_7235198
loop_
_publ_author_name
'Sandra Schraff'
'Yu Sun'
'Frank Pammer'
_publ_section_title
;
 Tuning of electronic properties via labile N->B-coordination in
 conjugated organoboranes
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1730
_journal_page_last               1741
_journal_paper_doi               10.1039/C6TC05418H
_journal_volume                  5
_journal_year                    2017
_chemical_formula_sum            'C46 H48 B2'
_chemical_formula_weight         622.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                69.417(8)
_cell_angle_beta                 88.074(7)
_cell_angle_gamma                78.462(6)
_cell_formula_units_Z            1
_cell_length_a                   6.9356(5)
_cell_length_b                   11.2669(9)
_cell_length_c                   12.5929(13)
_cell_measurement_reflns_used    3492
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.8890
_cell_measurement_theta_min      3.7020
_cell_volume                     901.89(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3385
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8238
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.237
_diffrn_reflns_theta_min         3.000
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_description       'transparent prism'
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0509
_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)+(0.0511P)²+0.3130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1307
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3342
_reflns_number_total             4241
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2017-5-1730.cif
_cod_data_source_block           1
_cod_database_code               7235198
_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   0.989
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.1433(2) 0.29975(14) 0.55455(13) 0.0290(3) Uani 1 1 d . . . . .
H1 H 0.0597 0.3671 0.5728 0.035 Uiso 1 1 calc R U . . .
C2 C 0.2478(2) 0.21568(13) 0.53172(11) 0.0220(3) Uani 1 1 d . . . . .
C3 C 0.3760(2) 0.10870(13) 0.51175(11) 0.0204(3) Uani 1 1 d . . . . .
C4 C 0.4376(2) 0.11468(13) 0.40215(11) 0.0205(3) Uani 1 1 d . . . . .
C5 C 0.5603(2) 0.00383(13) 0.39426(11) 0.0208(3) Uani 1 1 d . . . . .
H5 H 0.6026 0.0048 0.3215 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3564(2) 0.37852(12) 0.28739(11) 0.0201(3) Uani 1 1 d . . . . .
C7 C 0.4973(2) 0.41488(13) 0.34166(11) 0.0229(3) Uani 1 1 d . . . . .
C8 C 0.4726(2) 0.54195(14) 0.33918(12) 0.0264(3) Uani 1 1 d . . . . .
H8 H 0.5700 0.5647 0.3754 0.032 Uiso 1 1 calc R U . . .
C9 C 0.3103(2) 0.63550(13) 0.28543(12) 0.0261(3) Uani 1 1 d . . . . .
C10 C 0.1724(2) 0.60015(13) 0.23160(12) 0.0257(3) Uani 1 1 d . . . . .
H10 H 0.0599 0.6634 0.1946 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1923(2) 0.47550(13) 0.22969(11) 0.0221(3) Uani 1 1 d . . . . .
C12 C 0.6818(2) 0.32164(15) 0.40103(14) 0.0326(4) Uani 1 1 d . . . . .
H12A H 0.7830 0.3701 0.4038 0.049 Uiso 1 1 calc R U . . .
H12B H 0.7297 0.2633 0.3594 0.049 Uiso 1 1 calc R U . . .
H12C H 0.6525 0.2709 0.4785 0.049 Uiso 1 1 calc R U . . .
C13 C 0.2847(3) 0.77234(15) 0.28338(15) 0.0363(4) Uani 1 1 d . . . . .
H13A H 0.2694 0.8324 0.2046 0.055 Uiso 1 1 calc R U . . .
H13B H 0.4007 0.7814 0.3199 0.055 Uiso 1 1 calc R U . . .
H13C H 0.1672 0.7922 0.3244 0.055 Uiso 1 1 calc R U . . .
C14 C 0.0346(2) 0.45017(15) 0.16612(14) 0.0329(4) Uani 1 1 d . . . . .
H14A H -0.0729 0.5264 0.1417 0.049 Uiso 1 1 calc R U . . .
H14B H -0.0163 0.3753 0.2158 0.049 Uiso 1 1 calc R U . . .
H14C H 0.0901 0.4323 0.0994 0.049 Uiso 1 1 calc R U . . .
C15 C 0.3509(2) 0.20622(12) 0.17859(11) 0.0204(3) Uani 1 1 d . . . . .
C16 C 0.4649(2) 0.25101(13) 0.08290(11) 0.0227(3) Uani 1 1 d . . . . .
C17 C 0.4361(2) 0.22328(14) -0.01411(12) 0.0264(3) Uani 1 1 d . . . . .
H17 H 0.5146 0.2532 -0.0775 0.032 Uiso 1 1 calc R U . . .
C18 C 0.2968(2) 0.15339(14) -0.02123(12) 0.0267(3) Uani 1 1 d . . . . .
C19 C 0.1828(2) 0.11152(14) 0.07237(12) 0.0258(3) Uani 1 1 d . . . . .
H19 H 0.0841 0.0655 0.0684 0.031 Uiso 1 1 calc R U . . .
C20 C 0.2092(2) 0.13504(13) 0.17177(12) 0.0231(3) Uani 1 1 d . . . . .
C21 C 0.6240(2) 0.32490(16) 0.08423(13) 0.0319(4) Uani 1 1 d . . . . .
H21A H 0.6818 0.3510 0.0095 0.048 Uiso 1 1 calc R U . . .
H21B H 0.7266 0.2695 0.1418 0.048 Uiso 1 1 calc R U . . .
H21C H 0.5667 0.4021 0.1023 0.048 Uiso 1 1 calc R U . . .
C22 C 0.2744(3) 0.12032(17) -0.12587(13) 0.0355(4) Uani 1 1 d . . . . .
H22A H 0.2859 0.1949 -0.1938 0.053 Uiso 1 1 calc R U . . .
H22B H 0.1450 0.0985 -0.1277 0.053 Uiso 1 1 calc R U . . .
H22C H 0.3777 0.0461 -0.1240 0.053 Uiso 1 1 calc R U . . .
C23 C 0.0791(2) 0.08584(15) 0.26990(13) 0.0298(3) Uani 1 1 d . . . . .
H23A H -0.0310 0.0594 0.2434 0.045 Uiso 1 1 calc R U . . .
H23B H 0.0279 0.1548 0.3000 0.045 Uiso 1 1 calc R U . . .
H23C H 0.1562 0.0115 0.3298 0.045 Uiso 1 1 calc R U . . .
B1 B 0.3793(2) 0.23616(15) 0.28945(13) 0.0204(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 0.0033 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'
B B 0.0013 0.0007 '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
C2 C1 H1 180.0 . .
C1 C2 C3 176.28(15) . .
C5 C3 C4 120.10(12) 2_656 .
C5 C3 C2 117.58(12) 2_656 .
C4 C3 C2 122.31(12) . .
C5 C4 C3 116.60(12) . .
C5 C4 B1 118.15(12) . .
C3 C4 B1 125.24(12) . .
C4 C5 C3 123.29(12) . 2_656
C4 C5 H5 118.4 . .
C3 C5 H5 118.4 2_656 .
C7 C6 C11 117.74(12) . .
C7 C6 B1 121.61(12) . .
C11 C6 B1 120.64(13) . .
C8 C7 C6 120.43(13) . .
C8 C7 C12 117.17(14) . .
C6 C7 C12 122.38(13) . .
C9 C8 C7 121.80(14) . .
C9 C8 H8 119.1 . .
C7 C8 H8 119.1 . .
C8 C9 C10 117.84(13) . .
C8 C9 C13 121.44(15) . .
C10 C9 C13 120.71(14) . .
C9 C10 C11 122.55(13) . .
C9 C10 H10 118.7 . .
C11 C10 H10 118.7 . .
C10 C11 C6 119.60(14) . .
C10 C11 C14 117.40(13) . .
C6 C11 C14 123.00(12) . .
C7 C12 H12A 109.5 . .
C7 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C7 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C9 C13 H13A 109.5 . .
C9 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C9 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C20 C15 C16 118.21(13) . .
C20 C15 B1 120.69(12) . .
C16 C15 B1 121.10(13) . .
C17 C16 C15 119.81(14) . .
C17 C16 C21 118.56(13) . .
C15 C16 C21 121.59(13) . .
C18 C17 C16 122.18(14) . .
C18 C17 H17 118.9 . .
C16 C17 H17 118.9 . .
C17 C18 C19 117.78(13) . .
C17 C18 C22 121.00(14) . .
C19 C18 C22 121.20(15) . .
C18 C19 C20 121.90(14) . .
C18 C19 H19 119.1 . .
C20 C19 H19 119.1 . .
C19 C20 C15 120.10(13) . .
C19 C20 C23 118.55(14) . .
C15 C20 C23 121.32(13) . .
C16 C21 H21A 109.5 . .
C16 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C16 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C18 C22 H22A 109.5 . .
C18 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C18 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C20 C23 H23A 109.5 . .
C20 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C20 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C6 B1 C15 121.79(11) . .
C6 B1 C4 122.04(12) . .
C15 B1 C4 116.15(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.186(2) .
C1 H1 0.9500 .
C2 C3 1.4409(19) .
C3 C5 1.4000(18) 2_656
C3 C4 1.4136(19) .
C4 C5 1.3964(18) .
C4 B1 1.5819(19) .
C5 C3 1.3999(18) 2_656
C5 H5 0.9500 .
C6 C7 1.411(2) .
C6 C11 1.4205(19) .
C6 B1 1.571(2) .
C7 C8 1.397(2) .
C7 C12 1.508(2) .
C8 C9 1.382(2) .
C8 H8 0.9500 .
C9 C10 1.385(2) .
C9 C13 1.507(2) .
C10 C11 1.3921(19) .
C10 H10 0.9500 .
C11 C14 1.504(2) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C20 1.409(2) .
C15 C16 1.4139(19) .
C15 B1 1.574(2) .
C16 C17 1.393(2) .
C16 C21 1.513(2) .
C17 C18 1.386(2) .
C17 H17 0.9500 .
C18 C19 1.390(2) .
C18 C22 1.511(2) .
C19 C20 1.392(2) .
C19 H19 0.9500 .
C20 C23 1.514(2) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 140136288
