Triclinic and orthorhombic polymorphs of 2-iodo-4-nitroaniline: interplay of hydrogen bonds, nitro···I interactions and aromatic π–π-stacking interactions
McWilliam, Susan A.; Skakle, Janet M.S.; Low, John N.; Wardell, James L.; Garden, Simon J.; Pinto, Angelo C.; Torres, Jose C.; Glidewell, Christopher; Acta Crystallographica Section C 57 (2001) 942–945; doi:10.1107/S0108270101007053

data_2012160
_publ_section_title
;
 Triclinic and orthorhombic polymorphs of 2-iodo-4-nitroaniline:
 interplay of hydrogen bonds, nitro&#x00B7;&#x00B7;&#x00B7;I
 interactions and aromatic \p--\p-stacking interactions
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              942
_journal_page_last               945
_journal_paper_doi               10.1107/S0108270101007053
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C6 H5 I N2 O2'
_chemical_formula_sum            'C6 H5 I N2 O2'
_chemical_formula_weight         264.02
_chemical_name_systematic
;
2-Iodo-4-nitroaniline
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.4215(5)
_cell_length_b                   12.6755(9)
_cell_length_c                   16.4638(11)
_cell_measurement_reflns_used    2339
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.14
_cell_measurement_theta_min      2.47
_cell_volume                     1548.77(18)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2001)'
_computing_publication_material  'SHELXL97  and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full .998
_diffrn_measured_fraction_theta_max .935
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD 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     .71073
_diffrn_reflns_av_R_equivalents  .0886
_diffrn_reflns_av_sigmaI/netI    .0695
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12391
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         31.14
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    4.084
_exptl_absorpt_correction_T_max  .887
_exptl_absorpt_correction_T_min  .495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .03
_refine_diff_density_max         '2.20 (0.91 \%A from I2)'
_refine_diff_density_min         '-1.21 (0.90 \%A from I2)'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .961
_refine_ls_R_factor_all          .1376
_refine_ls_R_factor_gt           .0631
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0943P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1798
_reflns_number_gt                1109
_reflns_number_total             2339
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk1480.cif
_cod_data_source_block           Ib
_cod_database_code               2012160
_cod_database_fobs_code          2012160