#------------------------------------------------------------------------------
#$Date: 2020-05-30 02:13:17 +0300 (Sat, 30 May 2020) $
#$Revision: 252462 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038434.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_4038434
loop_
_publ_author_name
'Zhang, Qian'
'Sun, Zhe'
'Zhang, Lei'
'Li, Mengyuan'
'Zi, Lingjian'
'Liu, Zongyu'
'Zhen, Bin'
'Sun, Wenfang'
'Liu, Xuguang'
_publ_section_title
;
 Synthesis, Structures, and Properties of BN-Dinaphthothiophenes:
 Influence of B and N Placement on Photophysical Properties and
 Aromaticity.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00541
_journal_year                    2020
_chemical_formula_moiety         'B2 C30 N2 S, C H Cl3'
_chemical_formula_sum            'C31 H23 B2 Cl3 N2 S'
_chemical_formula_weight         583.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.34(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.915(5)
_cell_length_b                   8.985(4)
_cell_length_c                   25.802(9)
_cell_measurement_reflns_used    843
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.1200
_cell_measurement_theta_min      2.5010
_cell_volume                     5765(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.815
_diffrn_measured_fraction_theta_max 0.815
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00 117.00   1.00   10.00    --   30.00  54.00 240.00  122
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0193783000
_diffrn_orient_matrix_UB_12      0.0033709000
_diffrn_orient_matrix_UB_13      -0.0147044000
_diffrn_orient_matrix_UB_21      0.0210204000
_diffrn_orient_matrix_UB_22      -0.0005557000
_diffrn_orient_matrix_UB_23      0.0246649000
_diffrn_orient_matrix_UB_31      0.0009468000
_diffrn_orient_matrix_UB_32      -0.0784815000
_diffrn_orient_matrix_UB_33      -0.0007528000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1398
_diffrn_reflns_av_unetI/netI     0.1467
_diffrn_reflns_Laue_measured_fraction_full 0.815
_diffrn_reflns_Laue_measured_fraction_max 0.815
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5432
_diffrn_reflns_point_group_measured_fraction_full 0.815
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.410
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.2107
_refine_ls_R_factor_gt           0.1443
_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)+(0.1898P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3537
_refine_ls_wR_factor_ref         0.4083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1806
_reflns_number_total             4151
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00541_si_003.cif
_cod_data_source_block           1
_cod_database_code               4038434
_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_max   0.929
_shelx_estimated_absorpt_t_min   0.914
_reflns_odcompleteness_completeness 61.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.85
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C31(H31)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.033
_oxdiff_exptl_absorpt_empirical_full_min 0.479
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
B1 B 0.8314(4) 0.4597(12) 0.6376(4) 0.046(2) Uani 1 1 d . . . . .
B2 B 0.6073(4) 0.4557(12) 0.6404(4) 0.050(3) Uani 1 1 d . . . . .
C1 C 0.8633(3) 0.5977(10) 0.6671(3) 0.043(2) Uani 1 1 d . . . . .
C2 C 0.9173(3) 0.6255(11) 0.6659(4) 0.053(2) Uani 1 1 d . . . . .
C3 C 0.9446(4) 0.7506(12) 0.6897(4) 0.064(3) Uani 1 1 d . . . . .
C4 C 0.9194(4) 0.8503(12) 0.7163(4) 0.065(3) Uani 1 1 d . . . . .
C5 C 0.8675(4) 0.8297(11) 0.7198(4) 0.060(3) Uani 1 1 d . . . . .
C6 C 0.8379(3) 0.7011(10) 0.6935(3) 0.045(2) Uani 1 1 d . . . . .
C7 C 0.7828(3) 0.6754(9) 0.6941(3) 0.044(2) Uani 1 1 d . . . . .
C8 C 0.7538(3) 0.5518(10) 0.6666(3) 0.045(2) Uani 1 1 d . . . . .
C9 C 0.7000(3) 0.5507(10) 0.6680(4) 0.046(2) Uani 1 1 d . . . . .
C10 C 0.6855(3) 0.6717(10) 0.6939(3) 0.047(2) Uani 1 1 d . . . . .
C11 C 0.6305(3) 0.6987(10) 0.6957(4) 0.048(2) Uani 1 1 d . . . . .
C12 C 0.6159(4) 0.8230(11) 0.7204(4) 0.053(2) Uani 1 1 d . . . . .
C13 C 0.5634(4) 0.8490(12) 0.7181(4) 0.062(3) Uani 1 1 d . . . . .
C14 C 0.5217(4) 0.7467(13) 0.6894(4) 0.070(3) Uani 1 1 d . . . . .
C15 C 0.5364(4) 0.6233(11) 0.6652(3) 0.051(2) Uani 1 1 d . . . . .
C16 C 0.5905(3) 0.5940(10) 0.6663(3) 0.044(2) Uani 1 1 d . . . . .
C17 C 0.5649(3) 0.3368(10) 0.6095(4) 0.046(2) Uani 1 1 d . . . . .
C18 C 0.5244(4) 0.3781(11) 0.5630(4) 0.062(3) Uani 1 1 d . . . . .
C19 C 0.4860(4) 0.2709(13) 0.5333(5) 0.074(3) Uani 1 1 d . . . . .
C20 C 0.4883(4) 0.1286(14) 0.5512(5) 0.076(3) Uani 1 1 d . . . . .
C21 C 0.5287(4) 0.0809(11) 0.5975(6) 0.076(3) Uani 1 1 d . . . . .
C22 C 0.5675(4) 0.1856(11) 0.6262(4) 0.060(3) Uani 1 1 d . . . . .
C23 C 0.6874(4) 0.3161(13) 0.6192(6) 0.086(4) Uani 1 1 d . . . . .
C24 C 0.7351(4) 0.3459(16) 0.6058(7) 0.117(6) Uani 1 1 d . . . . .
C25 C 0.8561(3) 0.3393(10) 0.6078(4) 0.048(2) Uani 1 1 d . . . . .
C26 C 0.8734(4) 0.3739(11) 0.5620(4) 0.060(3) Uani 1 1 d . . . . .
C27 C 0.8947(4) 0.2730(14) 0.5343(5) 0.072(3) Uani 1 1 d . . . . .
C28 C 0.8994(4) 0.1240(13) 0.5494(5) 0.071(3) Uani 1 1 d . . . . .
C29 C 0.8816(4) 0.0819(13) 0.5956(6) 0.083(4) Uani 1 1 d . . . . .
C30 C 0.8591(3) 0.1877(11) 0.6240(4) 0.060(3) Uani 1 1 d . . . . .
C31 C 0.6940(5) 0.8304(13) 0.5650(6) 0.087(4) Uani 1 1 d . . . . .
H31 H 0.7078 0.7640 0.5960 0.105 Uiso 1 1 calc R . . . .
Cl1 Cl 0.6747(2) 0.7206(5) 0.5109(2) 0.150(2) Uani 1 1 d . . . . .
Cl2 Cl 0.74490(19) 0.9501(6) 0.5654(3) 0.160(2) Uani 1 1 d . . . . .
Cl3 Cl 0.63842(16) 0.9238(5) 0.57661(16) 0.1085(13) Uani 1 1 d . . . . .
N1 N 0.7766(3) 0.4483(8) 0.6400(3) 0.052(2) Uani 1 1 d . . . . .
N2 N 0.6620(3) 0.4397(8) 0.6420(3) 0.0490(19) Uani 1 1 d . . . . .
S1 S 0.74164(8) 0.7882(3) 0.71939(10) 0.0544(8) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
Cl Cl 0.1484 0.1585 '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
C1 B1 C25 123.7(7) . . ?
N1 B1 C1 115.2(8) . . ?
N1 B1 C25 121.0(7) . . ?
C16 B2 C17 121.8(8) . . ?
N2 B2 C16 118.4(7) . . ?
N2 B2 C17 119.7(9) . . ?
C2 C1 B1 121.0(8) . . ?
C6 C1 B1 120.1(7) . . ?
C6 C1 C2 118.9(8) . . ?
C3 C2 C1 121.1(9) . . ?
C2 C3 C4 119.4(9) . . ?
C5 C4 C3 122.8(9) . . ?
C4 C5 C6 118.3(9) . . ?
C1 C6 C7 119.4(7) . . ?
C5 C6 C1 119.5(8) . . ?
C5 C6 C7 121.1(8) . . ?
C6 C7 S1 128.7(6) . . ?
C8 C7 C6 120.3(7) . . ?
C8 C7 S1 110.7(6) . . ?
C9 C8 C7 112.5(7) . . ?
N1 C8 C7 122.5(7) . . ?
N1 C8 C9 125.0(7) . . ?
C8 C9 N2 123.4(8) . . ?
C10 C9 C8 114.4(7) . . ?
C10 C9 N2 122.1(8) . . ?
C9 C10 C11 123.1(7) . . ?
C9 C10 S1 109.8(6) . . ?
C11 C10 S1 127.0(7) . . ?
C12 C11 C10 122.8(8) . . ?
C12 C11 C16 121.1(8) . . ?
C16 C11 C10 116.0(8) . . ?
C13 C12 C11 120.9(9) . . ?
C12 C13 C14 120.2(9) . . ?
C15 C14 C13 118.6(9) . . ?
C14 C15 C16 122.6(9) . . ?
C11 C16 B2 120.5(7) . . ?
C15 C16 B2 122.9(8) . . ?
C15 C16 C11 116.6(8) . . ?
C18 C17 B2 119.9(8) . . ?
C18 C17 C22 118.2(8) . . ?
C22 C17 B2 121.8(8) . . ?
C17 C18 C19 121.1(9) . . ?
C20 C19 C18 119.5(10) . . ?
C19 C20 C21 121.6(9) . . ?
C20 C21 C22 119.1(10) . . ?
C17 C22 C21 120.5(9) . . ?
C24 C23 N2 118.2(9) . . ?
C23 C24 N1 120.6(11) . . ?
C26 C25 B1 121.9(9) . . ?
C26 C25 C30 117.0(9) . . ?
C30 C25 B1 121.1(8) . . ?
C27 C26 C25 124.3(10) . . ?
C26 C27 C28 120.5(11) . . ?
C27 C28 C29 117.5(10) . . ?
C30 C29 C28 121.5(11) . . ?
C29 C30 C25 119.1(10) . . ?
Cl1 C31 H31 106.1 . . ?
Cl1 C31 Cl2 115.3(9) . . ?
Cl1 C31 Cl3 110.9(7) . . ?
Cl2 C31 H31 106.1 . . ?
Cl2 C31 Cl3 111.6(7) . . ?
Cl3 C31 H31 106.1 . . ?
B1 N1 C24 124.7(8) . . ?
C8 N1 B1 122.5(7) . . ?
C8 N1 C24 111.7(7) . . ?
B2 N2 C23 127.8(7) . . ?
C9 N2 B2 119.7(7) . . ?
C9 N2 C23 112.5(7) . . ?
C7 S1 C10 92.5(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
B1 C1 1.563(12) . ?
B1 C25 1.563(14) . ?
B1 N1 1.444(11) . ?
B2 C16 1.531(14) . ?
B2 C17 1.578(12) . ?
B2 N2 1.415(12) . ?
C1 C2 1.431(11) . ?
C1 C6 1.420(12) . ?
C2 C3 1.377(13) . ?
C3 C4 1.397(15) . ?
C4 C5 1.384(14) . ?
C5 C6 1.446(11) . ?
C6 C7 1.452(11) . ?
C7 C8 1.414(11) . ?
C7 S1 1.726(8) . ?
C8 C9 1.405(12) . ?
C8 N1 1.384(11) . ?
C9 C10 1.383(13) . ?
C9 N2 1.429(10) . ?
C10 C11 1.459(12) . ?
C10 S1 1.762(8) . ?
C11 C12 1.390(13) . ?
C11 C16 1.446(11) . ?
C12 C13 1.364(13) . ?
C13 C14 1.454(14) . ?
C14 C15 1.377(14) . ?
C15 C16 1.419(12) . ?
C17 C18 1.402(13) . ?
C17 C22 1.421(13) . ?
C18 C19 1.442(13) . ?
C19 C20 1.354(16) . ?
C20 C21 1.417(17) . ?
C21 C22 1.423(13) . ?
C23 C24 1.399(15) . ?
C23 N2 1.495(12) . ?
C24 N1 1.499(12) . ?
C25 C26 1.411(14) . ?
C25 C30 1.420(13) . ?
C26 C27 1.365(15) . ?
C27 C28 1.391(16) . ?
C28 C29 1.444(18) . ?
C29 C30 1.421(16) . ?
C31 H31 0.9800 . ?
C31 Cl1 1.667(14) . ?
C31 Cl2 1.699(14) . ?
C31 Cl3 1.765(13) . ?
