Crystal Structure of 1,9-Dibromo-5-phenyldipyrrin, Tetrapyrrole Synthesis Derivative and Free Base Ligand of BODIPY Building Blocks
O’SHEA, Donal F.; SOMMER, Roger D.; TANIGUCHI, Masahiko; LINDSEY, Jonathan S.; X-ray Structure Analysis Online 36 (2020) 21–22; doi:10.2116/xraystruct.36.21

data_1558793
_publ_section_title
;
 Crystal Structure of 1,9-Dibromo-5-phenyldipyrrin, Tetrapyrrole Synthesis
 Derivative and Free Base Ligand of BODIPY Building Blocks
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              21
_journal_page_last               22
_journal_paper_doi               10.2116/xraystruct.36.21
_journal_volume                  36
_journal_year                    2020
_chemical_formula_moiety         'C15 H10 Br2 N2'
_chemical_formula_sum            'C15 H10 Br2 N2'
_chemical_formula_weight         378.07
_chemical_name_common            Integration
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 118.8050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.94150(10)
_cell_length_b                   15.8691(3)
_cell_length_c                   10.2160(2)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    566.(2)
_cell_measurement_theta_max      23.1109
_cell_measurement_theta_min      2.5670
_cell_volume                     1412.28(4)
_computing_data_reduction
;
Bruker-Nonius, SAINT+ version 7.07B, (2004), Bruker-Nonius, Madison, WI 53711,
USA
;
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      566.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            84002
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.34
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    5.726
_exptl_absorpt_correction_T_max  0.50
_exptl_absorpt_correction_T_min  0.30
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker--Nonius, SADABS version 2.10, (2004), Bruker--Nonius, Madison, WI 53711,
USA
;
_exptl_crystal_colour            brown-gold
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.561
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0266
_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^)+(0.0252P)^2^+1.3245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0653
_reflns_number_gt                2376
_reflns_number_total             2896
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            36_21_1.txt
_cod_data_source_block           x06037
_cod_depositor_comments          'Adding full bibliography for 1558793.cif.'
_cod_database_code               1558793
_shelx_res_checksum              89368
_shelx_hkl_checksum              53450