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_2242387
_publ_section_title
;
 Crystal structures of methyl 3,5-dibromo-4-cyanobenzoate and methyl
 3,5-dibromo-4-isocyanobenzoate
;
_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          391
_chemical_name_common            RNC
_chemical_name_systematic        'Methyl 3,5-dibromo-4-isocyanobenzoate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90.002(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9233(9)
_cell_length_b                   13.554(3)
_cell_length_c                   18.672(4)
_cell_measurement_reflns_used    2953
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.18
_cell_volume                     992.9(4)
_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 0.998
_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  0.0526
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11400
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         1.090
_exptl_absorpt_coefficient_mu    8.134
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.134
_exptl_crystal_description       Needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.653
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0385P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0689
_reflns_number_gt                2132
_reflns_number_total             2277
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5870sup1.cif
_cod_data_source_block           RNC
_cod_database_code               2242387
_cod_database_fobs_code          2242387
_shelx_estimated_absorpt_t_min   0.106
_shelx_estimated_absorpt_t_max   0.792
_shelx_hkl_checksum              14850
_shelx_res_checksum              26906
_shelxl_version_number           2014/6