Interplay of hydrogen bonds, iodo···nitro interactions and aromatic π···π stacking interactions in iodo-nitroanilines
Garden, Simon J.; Fontes, Silvia P.; Wardell, James L.; Skakle, Janet M. S.; Low, John N.; Glidewell, Christopher; Acta Crystallographica Section B 58 (2002) 701–709; doi:10.1107/S0108768102007978

data_2103326
_publ_section_title
;
 Interplay of hydrogen bonds, iodo&#x00B7;&#x00B7;&#x00B7;nitro
 interactions and aromatic \p&#x00B7;&#x00B7;&#x00B7;\p stacking
 interactions in iodo-nitroanilines
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              701
_journal_page_last               709
_journal_paper_doi               10.1107/S0108768102007978
_journal_volume                  58
_journal_year                    2002
_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-5-nitro-aniline
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                71.422(4)
_cell_angle_beta                 85.285(4)
_cell_angle_gamma                86.125(4)
_cell_formula_units_Z            2
_cell_length_a                   6.4236(15)
_cell_length_b                   7.4979(18)
_cell_length_c                   8.293(2)
_cell_measurement_reflns_used    1674
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      2.60
_cell_volume                     376.96(16)
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2002)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 1997) and  PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.880
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2274
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         28.44
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    4.195
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_correction_T_min  0.434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1997)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
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_refine_diff_density_min         -1.864
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         1674
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_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0823P)^2^+0.6322P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                1620
_reflns_number_total             1674
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            na0135.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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_cell_volume        376.98(16)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2103326