Synthesis, Structures, and Properties of BN-Dinaphthothiophenes: Influence of B and N Placement on Photophysical Properties and Aromaticity.
Zhang, Qian; Sun, Zhe; Zhang, Lei; Li, Mengyuan; Zi, Lingjian; Liu, Zongyu; Zhen, Bin; Sun, Wenfang; Liu, Xuguang; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00541

data_4038434
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -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       '\w 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/[\s^2^(Fo^2^)+(0.1898P)^2^] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              16719
_shelx_hkl_checksum              60036
_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