Hydrogen bonding in C-substituted nitroanilines: π-stacked sheets of <i>R</i>f̱{_4^4}(20) and <i>R</i>f̱{_4^4}(28) rings in 2-cyano-4-nitroaniline
Glidewell, Christopher; Low, John N.; Skakle, Janet M. S.; Wardell, James L.; Acta Crystallographica Section C 60 (2004) o35–o37; doi:10.1107/S0108270103027057

data_2013862
_publ_section_title
;
 Hydrogen bonding in C-substituted nitroanilines: \p-stacked sheets of
 <i>R</i>f&#x0331;{_4^4}(20) and <i>R</i>f&#x0331;{_4^4}(28) rings in
 2-cyano-4-nitroaniline
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o35
_journal_page_last               o37
_journal_paper_doi               10.1107/S0108270103027057
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C7 H5 N3 O2'
_chemical_formula_moiety         'C7 H5 N3 O2'
_chemical_formula_sum            'C7 H5 N3 O2'
_chemical_formula_weight         163.14
_chemical_name_systematic
;
2-Cyano-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
_cell_angle_beta                 94.630(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.2316(4)
_cell_length_b                   17.7275(7)
_cell_length_c                   7.1078(2)
_cell_measurement_reflns_used    3216
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.93
_cell_volume                     1410.60(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction        DENZO-SMN
_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      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '\f scans, and \w scans with \k offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.059
_diffrn_reflns_av_sigmaI/netI    0.044
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19532
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.93
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995, 1997)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3216
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.083
_refine_ls_R_factor_gt           0.044
_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^)+(0.0739P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.109
_refine_ls_wR_factor_ref         0.126
_reflns_number_gt                2067
_reflns_number_total             3216
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk1684.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/c'
_cod_database_code               2013862
_cod_database_fobs_code          2013862