Hydrogen bonding in C-substituted nitroanilines: simple <i>C</i>(8) chains in 2-bromo-6-chloro-4-nitroaniline
Glidewell, Christopher; Low, John N.; Skakle, Janet M. S.; Wardell, James L.; Acta Crystallographica Section C 61 (2005) o336–o338; doi:10.1107/S0108270105010085

data_2014911
_publ_section_title
;
 Hydrogen bonding in C-substituted nitroanilines: simple <i>C</i>(8)
 chains in 2-bromo-6-chloro-4-nitroaniline
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o336
_journal_page_last               o338
_journal_paper_doi               10.1107/S0108270105010085
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C6 H4 Br0.90 Cl1.10 N2 O2'
_chemical_formula_moiety         'C6 H4 Br0.90 Cl1.10 N2 O2'
_chemical_formula_sum            'C6 H4 Br0.9 Cl1.1 N2 O2'
_chemical_formula_weight         247.02
_chemical_name_systematic
;
2-bromo-6-chloro-4-nitroaniline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 93.224(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8052(3)
_cell_length_b                   17.9667(13)
_cell_length_c                   12.0417(9)
_cell_measurement_reflns_used    1863
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.04
_cell_volume                     821.95(11)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'OSCAIL and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       \f-\w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR91 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5904
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    4.828
_exptl_absorpt_correction_T_max  0.749
_exptl_absorpt_correction_T_min  0.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.996
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480.8
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.379
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1863
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0477P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                1357
_reflns_number_total             1863
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk1832.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C6 H4 Br0.90 Cl1.10 N2 O2'
_cod_database_code               2014911
_cod_database_fobs_code          2014911