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_2012159
_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           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                67.905(3)
_cell_angle_beta                 86.956(3)
_cell_angle_gamma                65.744(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1647(4)
_cell_length_b                   7.9572(4)
_cell_length_c                   8.0489(5)
_cell_measurement_reflns_used    1728
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.05
_cell_volume                     384.84(4)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa-CCD Server Software (Nonius, 1997)'
_computing_data_reduction        DENZO-SMN
_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      150(2)
_diffrn_measured_fraction_theta_full .988
_diffrn_measured_fraction_theta_max .972
_diffrn_measurement_device_type  Kappa-CCD
_diffrn_measurement_method       '\f scans, and \w scans with \k offsets'
_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  .047
_diffrn_reflns_av_sigmaI/netI    .0493
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4602
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.05
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    4.109
_exptl_absorpt_correction_T_max  .887
_exptl_absorpt_correction_T_min  .393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             248
_exptl_crystal_size_max          .28
_exptl_crystal_size_mid          .08
_exptl_crystal_size_min          .03
_refine_diff_density_max         '2.77 (0.96 \%A from I2)'
_refine_diff_density_min         '-2.14 (0.83 \%A from I2)'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          .0535
_refine_ls_R_factor_gt           .0460
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+1.2313P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1200
_reflns_number_gt                1556
_reflns_number_total             1728
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk1480.cif
_cod_data_source_block           Ia
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2012159
_cod_database_fobs_code          2012159