Synthesis of bis-BN-naphthalene-fused Oxepins and Their Photoluminescence Including White-Light Emission.
Tian, Dawei; Li, Qian; Zhao, Yifan; Wang, Zijia; Li, Wenbin; Xia, Shuling; Xing, Siyang; Zhu, Bolin; Zhang, Jianying; Cui, Chunming; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02594

data_4037758
_publ_section_title
;
 Synthesis of bis-BN-naphthalene-fused Oxepins and Their Photoluminescence
 Including White-Light Emission.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02594
_journal_year                    2019
_chemical_formula_moiety         'C37 H27 B2 Br N2 O2'
_chemical_formula_sum            'C37 H27 B2 Br N2 O2'
_chemical_formula_weight         633.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.598(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0689(7)
_cell_length_b                   8.5804(4)
_cell_length_c                   23.3930(11)
_cell_measurement_reflns_used    3041
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.3830
_cell_measurement_theta_min      3.5540
_cell_volume                     3018.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -46.00  27.00   1.00   14.44    --  -41.49  38.00 -30.00   73
  2  \w   -118.00  -9.00   1.00   14.44    --  -41.49 -77.00-120.00  109
  3  \w    -22.00  27.00   1.00   14.44    --  -41.49  57.00   0.00   49
  4  \w     32.00  88.00   1.00   14.44    --   41.49-125.00  90.00   56
  5  \w    -25.00  56.00   1.00   14.44    --   41.49 -38.00  60.00   81
  6  \w     72.00 132.00   1.00   77.77    --  107.08 -30.00 120.00   60
  7  \w     32.00 125.00   1.00   77.77    --  107.08 -30.00 -30.00   93
  8  \w     45.00  89.00   1.00   77.77    --  107.08 -95.00 -60.00   44
  9  \w     51.00 140.00   1.00   77.77    --  107.08 -77.00   0.00   89
 10  \w     31.00  84.00   1.00   77.77    --  107.08 -95.00-180.00   53
 11  \w    153.00 178.00   1.00   77.77    --  107.08  15.00 -90.00   25
 12  \w     47.00 103.00   1.00   77.77    --  107.08-112.00-101.00   56
 13  \w     46.00 117.00   1.00   77.77    --  107.08-125.00  30.00   71
 14  \w     81.00 169.00   1.00   77.77    --  107.08  45.00 150.00   88
 15  \w     40.00 116.00   1.00   77.77    --  107.08 -30.00-150.00   76
 16  \w     67.00 138.00   1.00   77.77    --  107.08  15.00 -90.00   71
 17  \w     89.00 124.00   1.00   77.77    --  107.08-134.00-168.66   35
 18  \w     37.00  73.00   1.00   77.77    --  107.08-134.00-168.66   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0494778000
_diffrn_orient_matrix_UB_12      0.1026462000
_diffrn_orient_matrix_UB_13      0.0456748000
_diffrn_orient_matrix_UB_21      0.0136949000
_diffrn_orient_matrix_UB_22      -0.1428556000
_diffrn_orient_matrix_UB_23      0.0394367000
_diffrn_orient_matrix_UB_31      0.0886315000
_diffrn_orient_matrix_UB_32      -0.0354411000
_diffrn_orient_matrix_UB_33      -0.0268035000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0800
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19640
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         3.394
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.144
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5393
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0698
_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^)+(0.1136P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1819
_refine_ls_wR_factor_ref         0.2161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3226
_reflns_number_total             5393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02594_si_003.cif
_cod_data_source_block           a180630d
_cod_database_code               4037758
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C37) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C5(H5), C7(H7), C12(H12), C14(H14), C16(H16),
  C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26),
 C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C35(H35), C36(H36)
3.b Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2018-06-30
_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 1.504
_oxdiff_exptl_absorpt_empirical_full_min 0.597