6-Bromoindigo dye
Szalda, David J.; Ramig, Keith; Lavinda, Olga; Koren, Zvi C.; Massa, Lou; Acta Crystallographica Section C 68 (2012) o160–o163; doi:10.1107/S0108270112006440

data_2018456
_publ_section_title
;
 6-Bromoindigo dye
;
_journal_coeditor_code           GG3263
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o160
_journal_page_last               o163
_journal_paper_doi               10.1107/S0108270112006440
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H9 Br N2 O2'
_chemical_formula_moiety         'C16 H9 Br N2 O2'
_chemical_formula_sum            'C16 H9 Br N2 O2'
_chemical_formula_weight         341.16
_chemical_name_systematic
;
6-bromo-2-(3-oxo-2,3-dihydro-1<i>H</i>-indol-2-ylidene)-2,3-dihydro-1<i>H</i>-
indol-3-one
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 105.856(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.347(3)
_cell_length_b                   4.6558(12)
_cell_length_c                   11.607(3)
_cell_measurement_reflns_used    1383
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.46
_cell_measurement_theta_min      3.58
_cell_volume                     641.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0881
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4715
_diffrn_reflns_theta_full        25.86
_diffrn_reflns_theta_max         25.86
_diffrn_reflns_theta_min         3.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.208
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.601
_refine_ls_abs_structure_details 'Flack (1983), with 934 Friedel pairs'
_refine_ls_abs_structure_Flack   0.42(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2180
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0590
_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^)+(0.0716P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1414
_reflns_number_gt                1558
_reflns_number_total             2180
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gg3263.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2018456
_cod_database_fobs_code          2018456