Crystal structures of methyl 3,5-dibromo-4-cyanobenzoate and methyl 3,5-dibromo-4-isocyanobenzoate
Noland, Wayland E.; Herzig, Ryan J.; Engwall, Abigail J.; Jensen, Renee C.; Tritch, Kenneth J.; Acta Crystallographica Section E 74 (2018) 345–348; doi:10.1107/S2056989018002256

data_2242386
_publ_section_title
;
 Crystal structures of methyl 3,5-dibromo-4-cyanobenzoate and methyl
 3,5-dibromo-4-isocyanobenzoate
;
_journal_coeditor_code           LH5870
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              345
_journal_page_last               348
_journal_paper_doi               10.1107/S2056989018002256
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C9 H5 Br2 N O2'
_chemical_formula_moiety         'C9 H5 Br2 N O2'
_chemical_formula_sum            'C9 H5 Br2 N O2'
_chemical_formula_weight         318.96
_chemical_melting_point          410
_chemical_name_common            RCN
_chemical_name_systematic        'Methyl 3,5-dibromo-4-cyanobenzoate'
_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   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 93.757(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9273(18)
_cell_length_b                   17.881(8)
_cell_length_c                   14.739(7)
_cell_measurement_reflns_used    2977
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.67
_cell_volume                     1032.8(8)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>, 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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  0.0430
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.814
_diffrn_reflns_theta_min         1.793
_exptl_absorpt_coefficient_mu    7.820
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.051
_exptl_crystal_description       Block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.518
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0263
_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^)+(0.0274P)^2^+0.0295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0593
_reflns_number_gt                2013
_reflns_number_total             2426
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5870sup1.cif
_cod_data_source_block           RCN
_cod_original_cell_volume        1032.9(8)
_cod_database_code               2242386
_cod_database_fobs_code          2242386
_shelx_estimated_absorpt_t_min   0.189
_shelx_estimated_absorpt_t_max   0.245
_shelx_hkl_checksum              70008
_shelx_res_checksum              82408
_shelxl_version_number           2014/6