#------------------------------------------------------------------------------
#$Date: 2017-06-04 13:06:38 +0300 (Sun, 04 Jun 2017) $
#$Revision: 197250 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/61/4126101.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_4126101
loop_
_publ_author_name
'Liu, Zhiqiang'
'Ishibashi, Jacob S. A.'
'Darrigan, Clovis'
'Dargelos, Alain'
'Chrostowska, Anna'
'Li, Bo'
'Vasiliu, Monica'
'Dixon, David A.'
'Liu, Shih-Yuan'
_publ_section_title
;
 The Least Stable Isomer of BN Naphthalene: Toward Predictive Trends for
 the Optoelectronic Properties of BN Acenes.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6082
_journal_page_last               6085
_journal_paper_doi               10.1021/jacs.7b02661
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C8 H7 B F N'
_chemical_formula_sum            'C8 H7 B F N'
_chemical_formula_weight         146.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 103.790(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.465(3)
_cell_length_b                   14.687(6)
_cell_length_c                   6.709(3)
_cell_measurement_reflns_used    1526
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.43
_cell_measurement_theta_min      2.77
_cell_volume                     714.4(5)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3916
_diffrn_reflns_point_group_measured_fraction_full 0.664
_diffrn_reflns_point_group_measured_fraction_max 0.641
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.431
_diffrn_reflns_theta_min         2.774
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2013). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 435 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       na
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2294
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0403
_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)+(0.0662P)²+0.1056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1176
_reflns_Friedel_coverage         0.319
_reflns_Friedel_fraction_full    0.338
_reflns_Friedel_fraction_max     0.312
_reflns_number_gt                2005
_reflns_number_total             2294
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b02661_si_003.cif
_cod_data_source_block           C8H7BFN
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4126101
_shelx_shelxl_version_number     2014/7
_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   0.944
_shelx_estimated_absorpt_t_max   0.969
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, 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
F1 F 0.1900(2) 0.21405(8) 0.3030(3) 0.0280(4) Uani 1 1 d . .
N1 N 0.3683(3) 0.44354(12) 0.3468(3) 0.0147(4) Uani 1 1 d . .
B1 B 0.5475(4) 0.48793(18) 0.3932(4) 0.0198(5) Uani 1 1 d . .
H1B H 0.671(4) 0.4395(18) 0.420(5) 0.024 Uiso 1 1 d . U
C1 C 0.3580(3) 0.34925(15) 0.3422(3) 0.0165(5) Uani 1 1 d . .
H1 H 0.4682 0.3144 0.3657 0.020 Uiso 1 1 calc R U
C2 C 0.1955(4) 0.30696(14) 0.3052(4) 0.0193(5) Uani 1 1 d . .
C3 C 0.0249(3) 0.35400(16) 0.2669(4) 0.0224(5) Uani 1 1 d . .
H3 H -0.0894 0.3225 0.2427 0.027 Uiso 1 1 calc R U
C4 C 0.0333(3) 0.44661(16) 0.2664(4) 0.0201(5) Uani 1 1 d . .
H4 H -0.0782 0.4806 0.2378 0.024 Uiso 1 1 calc R U
C5 C 0.2050(3) 0.49395(15) 0.3078(3) 0.0158(4) Uani 1 1 d . .
C6 C 0.2135(3) 0.58850(15) 0.3109(4) 0.0194(5) Uani 1 1 d . .
H6 H 0.1022 0.6226 0.2830 0.023 Uiso 1 1 calc R U
C7 C 0.3819(4) 0.63426(14) 0.3540(4) 0.0214(5) Uani 1 1 d . .
H7 H 0.3819 0.6989 0.3548 0.026 Uiso 1 1 calc R U
C8 C 0.5485(4) 0.58905(16) 0.3954(4) 0.0221(5) Uani 1 1 d . .
H8 H 0.6615 0.6218 0.4248 0.027 Uiso 1 1 calc R U
F2 F 0.6518(2) -0.21509(8) 0.6544(3) 0.0266(4) Uani 1 1 d . .
N2 N 0.8033(3) 0.01885(12) 0.6906(3) 0.0158(4) Uani 1 1 d . .
B2 B 0.9776(4) 0.06810(19) 0.7348(5) 0.0227(6) Uani 1 1 d . .
H2B H 1.107(4) 0.0212(19) 0.763(5) 0.027 Uiso 1 1 d . U
C9 C 0.8054(3) -0.07629(14) 0.6928(3) 0.0164(5) Uani 1 1 d . .
H9 H 0.9195 -0.1081 0.7235 0.020 Uiso 1 1 calc R U
C10 C 0.6455(4) -0.12281(14) 0.6515(4) 0.0187(5) Uani 1 1 d . .
C11 C 0.4721(3) -0.08046(16) 0.6039(4) 0.0210(5) Uani 1 1 d . .
H11 H 0.3612 -0.1150 0.5740 0.025 Uiso 1 1 calc R U
C12 C 0.4693(3) 0.01216(16) 0.6023(4) 0.0203(5) Uani 1 1 d . .
H12 H 0.3542 0.0430 0.5707 0.024 Uiso 1 1 calc R U
C13 C 0.6357(3) 0.06385(14) 0.6471(3) 0.0164(5) Uani 1 1 d . .
C14 C 0.6324(4) 0.15894(15) 0.6454(4) 0.0211(5) Uani 1 1 d . .
H14 H 0.5170 0.1896 0.6165 0.025 Uiso 1 1 calc R U
C15 C 0.7946(4) 0.20982(14) 0.6851(4) 0.0265(6) Uani 1 1 d . .
H15 H 0.7870 0.2744 0.6816 0.032 Uiso 1 1 calc R U
C16 C 0.9656(4) 0.16907(16) 0.7294(5) 0.0269(6) Uani 1 1 d . .
H16 H 1.0745 0.2050 0.7561 0.032 Uiso 1 1 calc R U
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C1 N1 C5 118.94(18)
C1 N1 B1 119.74(19)
C5 N1 B1 121.32(19)
N1 B1 C8 116.9(2)
N1 B1 H1B 114.9(14)
C8 B1 H1B 128.2(14)
C2 C1 N1 120.9(2)
C2 C1 H1 119.6
N1 C1 H1 119.6
C1 C2 F1 119.5(2)
C1 C2 C3 123.04(19)
F1 C2 C3 117.5(2)
C4 C3 C2 116.6(2)
C4 C3 H3 121.7
C2 C3 H3 121.7
C3 C4 C5 121.8(2)
C3 C4 H4 119.1
C5 C4 H4 119.1
C6 C5 N1 119.5(2)
C6 C5 C4 121.7(2)
N1 C5 C4 118.81(19)
C5 C6 C7 121.4(2)
C5 C6 H6 119.3
C7 C6 H6 119.3
C8 C7 C6 122.37(19)
C8 C7 H7 118.8
C6 C7 H7 118.8
C7 C8 B1 118.5(2)
C7 C8 H8 120.7
B1 C8 H8 120.7
C13 N2 C9 119.16(19)
C13 N2 B2 121.66(18)
C9 N2 B2 119.2(2)
N2 B2 C16 116.5(2)
N2 B2 H2B 113.9(14)
C16 B2 H2B 129.6(14)
C10 C9 N2 119.9(2)
C10 C9 H9 120.0
N2 C9 H9 120.0
C9 C10 F2 118.6(2)
C9 C10 C11 123.16(19)
F2 C10 C11 118.2(2)
C12 C11 C10 117.2(2)
C12 C11 H11 121.4
C10 C11 H11 121.4
C11 C12 C13 121.4(2)
C11 C12 H12 119.3
C13 C12 H12 119.3
N2 C13 C14 119.5(2)
N2 C13 C12 119.26(18)
C14 C13 C12 121.2(2)
C15 C14 C13 121.5(2)
C15 C14 H14 119.3
C13 C14 H14 119.3
C16 C15 C14 121.8(2)
C16 C15 H15 119.1
C14 C15 H15 119.1
C15 C16 B2 119.1(2)
C15 C16 H16 120.4
B2 C16 H16 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.365(2)
N1 C1 1.387(2)
N1 C5 1.397(3)
N1 B1 1.454(3)
B1 C8 1.485(3)
B1 H1B 1.15(3)
C1 C2 1.333(3)
C1 H1 0.9500
C2 C3 1.417(4)
C3 C4 1.362(3)
C3 H3 0.9500
C4 C5 1.426(3)
C4 H4 0.9500
C5 C6 1.390(3)
C6 C7 1.394(4)
C6 H6 0.9500
C7 C8 1.378(4)
C7 H7 0.9500
C8 H8 0.9500
F2 C10 1.356(2)
N2 C13 1.383(3)
N2 C9 1.398(2)
N2 B2 1.456(3)
B2 C16 1.486(3)
B2 H2B 1.16(3)
C9 C10 1.345(3)
C9 H9 0.9500
C10 C11 1.403(4)
C11 C12 1.360(3)
C11 H11 0.9500
C12 C13 1.425(3)
C12 H12 0.9500
C13 C14 1.397(3)
C14 C15 1.394(4)
C14 H14 0.9500
C15 C16 1.376(4)
C15 H15 0.9500
C16 H16 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
C1 N1 B1 C8 180.0(2)
C5 N1 B1 C8 -0.5(3)
C5 N1 C1 C2 -1.3(3)
B1 N1 C1 C2 178.3(2)
N1 C1 C2 F1 -179.6(2)
N1 C1 C2 C3 0.6(4)
C1 C2 C3 C4 0.9(4)
F1 C2 C3 C4 -179.0(2)
C2 C3 C4 C5 -1.6(4)
C1 N1 C5 C6 -179.7(2)
B1 N1 C5 C6 0.8(3)
C1 N1 C5 C4 0.6(3)
B1 N1 C5 C4 -179.0(2)
C3 C4 C5 C6 -178.8(2)
C3 C4 C5 N1 0.9(4)
N1 C5 C6 C7 -0.6(4)
C4 C5 C6 C7 179.2(2)
C5 C6 C7 C8 0.1(4)
C6 C7 C8 B1 0.2(4)
N1 B1 C8 C7 0.0(3)
C13 N2 B2 C16 -0.3(4)
C9 N2 B2 C16 179.8(2)
C13 N2 C9 C10 0.5(3)
B2 N2 C9 C10 -179.7(2)
N2 C9 C10 F2 179.88(19)
N2 C9 C10 C11 0.4(4)
C9 C10 C11 C12 -0.6(4)
F2 C10 C11 C12 179.9(2)
C10 C11 C12 C13 0.0(3)
C9 N2 C13 C14 179.7(2)
B2 N2 C13 C14 -0.1(3)
C9 N2 C13 C12 -1.0(3)
B2 N2 C13 C12 179.1(2)
C11 C12 C13 N2 0.8(4)
C11 C12 C13 C14 -180.0(2)
N2 C13 C14 C15 0.5(4)
C12 C13 C14 C15 -178.7(2)
C13 C14 C15 C16 -0.5(4)
C14 C15 C16 B2 0.0(4)
N2 B2 C16 C15 0.3(4)
