Crystal structure of 4'-bromo-2,5-dihydroxy-2',5'-dimethoxy-[1,1'-biphenyl]-3,4-dicarbonitrile
Meany, Joseph E.; Kelley, Steven P.; Rogers, Robin D.; Woski, Stephen A.; Acta Crystallographica Section E 72 (2016) 667–670; doi:10.1107/S2056989016005715

data_2241646
_publ_section_title
;
 Crystal structure of
 4'-bromo-2,5-dihydroxy-2',5'-dimethoxy-[1,1'-biphenyl]-3,4-dicarbonitrile
;
_journal_coeditor_code           ZS2361
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              667
_journal_page_last               670
_journal_paper_doi               10.1107/S2056989016005715
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C16 H11 Br N2 O4'
_chemical_formula_moiety         'C16 H11 Br N2 O4'
_chemical_formula_sum            'C16 H11 Br N2 O4'
_chemical_formula_weight         375.18
_chemical_name_systematic
;
4'-Bromo-2,5-dihydroxy-2',5'-dimethoxy-[1,1'-biphenyl]-3,4-dicarbonitrile
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 111.6985(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4726(3)
_cell_length_b                   23.7748(8)
_cell_length_c                   8.0833(3)
_cell_measurement_reflns_used    9370
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.86
_cell_measurement_theta_min      2.59
_cell_volume                     1512.88(9)
_computing_cell_refinement
;
SAINT (Bruker, 2010)
;
_computing_data_collection
;
APEX2 (Bruker, 2010)
;
_computing_data_reduction
;
SAINT (Bruker, 2010)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            65083
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.457
_diffrn_reflns_theta_min         1.713
_exptl_absorpt_coefficient_mu    2.739
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.4276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2010)
;
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.264
_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     216
_refine_ls_number_reflns         6269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0431P)^2^+0.4609P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                4739
_reflns_number_total             6269
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zs2361sup1.cif
_cod_data_source_block           I
_cod_database_code               2241646
_cod_database_fobs_code          2241646
_shelx_estimated_absorpt_t_min   0.447
_shelx_estimated_absorpt_t_max   0.791
_shelx_hkl_checksum              50582
_shelx_res_checksum              8907
_shelxl_version_number           .2013