gem-Dibromovinyl boron dipyrrins: synthesis, spectral properties and crystal structures.
Ali, Hasrat; Guérin, Brigitte; van Lier, Johan E.; Dalton transactions (Cambridge, England : 2003) 48 (2019) 11492–11507; doi:10.1039/c9dt02309g

data_7700409
_publ_section_title
;
 gem-Dibromovinyl boron dipyrrins: synthesis, spectral properties and
 crystal structures.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11492
_journal_page_last               11507
_journal_paper_doi               10.1039/c9dt02309g
_journal_volume                  48
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H23 B Br2 F2 N2'
_chemical_formula_sum            'C27 H23 B Br2 F2 N2'
_chemical_formula_weight         584.1
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc22jlx4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2018-09-06T08:28:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-06-12 deposited with the CCDC.    2019-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.91800(10)
_cell_length_b                   10.5403(2)
_cell_length_c                   33.2991(7)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.94
_cell_measurement_theta_min      4.4
_cell_measurement_wavelength     1.54184
_cell_volume                     2428.10(8)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_UB_11      -0.035203
_diffrn_orient_matrix_UB_12      -0.062552
_diffrn_orient_matrix_UB_13      0.021356
_diffrn_orient_matrix_UB_21      0.067295
_diffrn_orient_matrix_UB_22      -0.068585
_diffrn_orient_matrix_UB_23      -0.015326
_diffrn_orient_matrix_UB_31      0.122946
_diffrn_orient_matrix_UB_32      0.01963
_diffrn_orient_matrix_UB_33      0.014504
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1624
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            32681
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         71.187
_diffrn_reflns_theta_min         2.654
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.518
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.4712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.62
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details
;
 Flack x determined using 1162 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+2.1567P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                3496
_reflns_number_total             4637
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt02309g2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7700406--7700415.cif.'
_cod_database_code               7700409
_shelx_estimated_absorpt_t_min   0.194
_shelx_estimated_absorpt_t_max   0.915