Hydrogen bonding in substituted nitroanilines: hydrogen-bonded sheets in 4-iodo-3-nitroaniline
Garden, Simon J.; Wardell, James L.; Skakle, Janet M. S.; Low, John N.; Glidewell, Christopher; Acta Crystallographica Section C 60 (2004) o328–o330; doi:10.1107/S0108270104006092

data_2014009
_publ_section_title
;
 Hydrogen bonding in substituted nitroanilines: hydrogen-bonded sheets
 in 4-iodo-3-nitroaniline
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o328
_journal_page_last               o330
_journal_paper_doi               10.1107/S0108270104006092
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C6 H5 I N2 O2'
_chemical_formula_moiety         'C6 H5 I N2 O2'
_chemical_formula_sum            'C6 H5 I N2 O2'
_chemical_formula_weight         264.02
_chemical_name_systematic
;
4-iodo-3-nitroaniline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 111.5800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5174(7)
_cell_length_b                   4.2601(3)
_cell_length_c                   16.0042(9)
_cell_measurement_reflns_used    2848
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      32.52
_cell_measurement_theta_min      2.59
_cell_volume                     793.61(8)
_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      291(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       \f/\w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8259
_diffrn_reflns_theta_full        32.52
_diffrn_reflns_theta_max         32.52
_diffrn_reflns_theta_min         2.59
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    3.985
_exptl_absorpt_correction_T_max  0.819
_exptl_absorpt_correction_T_min  0.456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.100
_refine_diff_density_min         -0.854
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         2848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0553P)^2^+0.2861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                1971
_reflns_number_total             2848
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gg1211.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2014009
_cod_database_fobs_code          2014009