##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-10-19
_journal_date_accepted     2012-12-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      1
_journal_page_first     o114
_journal_page_last     o114
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812050878
_journal_coeditor_code     NR2034
_publ_contact_author_name
; Dr Muhammad D. Bala
;
_publ_contact_author_address
; School of Chemistry,
  University of KwaZulu-Natal,
  Westville Campus, Private Bag X54001
  Durban 4000,
  South Africa
;
_publ_contact_author_email     'bala@ukzn.ac.za'
_publ_contact_author_fax     '+27312603091'
_publ_contact_author_phone     '+27312602616'
_publ_section_title
;
1-(4-Nitrophenyl)-1H-imidazol-3-ium chloride
;
loop_
    _publ_author_name
    _publ_author_address
    'Ibrahim, Halliru'
; School of Chemistry & Physics,
  University of KwaZulu-Natal,
  Westville Campus, Private Bag X54001
  Durban 4000,
  South Africa
;
    'Bala, Muhammad D.'
; School of Chemistry & Physics,
  University of KwaZulu-Natal,
  Westville Campus, Private Bag X54001
  Durban 4000,
  South Africa
;
data_I
_chemical_name_systematic
;
1-(4-Nitrophenyl)-1H-imidazol-3-ium chloride
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H8 N3 O2 +, Cl -'
_chemical_formula_sum     'C9 H8 Cl N3 O2'
_chemical_formula_iupac     'C9 H8 N3 O2 +, Cl -'
_chemical_formula_weight     225.64
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y+1/2, z'
    '-x+1/2, y+1/2, z+1/2'
_cell_length_a     14.6042(8)
_cell_length_b     12.1781(7)
_cell_length_c     5.6070(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     997.21(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9896
_cell_measurement_theta_min     2.18
_cell_measurement_theta_max     28.27
_cell_measurement_temperature     173(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.54
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.503
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     464
_exptl_absorpt_coefficient_mu     0.365
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.5243
_exptl_absorpt_correction_T_max     0.7457
_exptl_special_details
;
Carbon-bound H-atoms were placed in calculated positions [C---H = 0.93 Å for
aromatic H atoms; Uiso(H) = 1.2Ueq(C)] and were included in
the refinement in the riding model. The nitrogen-bound H atom was located on a
difference Fourier map and refined freely with isotropic parameters.
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_reflns_number     20153
_diffrn_reflns_av_R_equivalents     0.0595
_diffrn_reflns_av_sigmaI/netI     0.0283
_diffrn_reflns_theta_min     2.18
_diffrn_reflns_theta_max     28.34
_diffrn_reflns_theta_full     28.34
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -7
_diffrn_reflns_limit_l_max     6
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2217
_reflns_number_gt     2120
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0311
_refine_ls_R_factor_gt     0.0290
_refine_ls_wR_factor_gt     0.0735
_refine_ls_wR_factor_ref     0.0758
_refine_ls_goodness_of_fit_ref     1.089
_refine_ls_restrained_S_all     1.087
_refine_ls_number_reflns     2217
_refine_ls_number_parameters     140
_refine_ls_number_restraints     8
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0354P)²+0.3302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.297
_refine_diff_density_min     -0.221
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
;
Flack (1983), Hooft et al. (2010) and Spek
(2009);
Hooft parameter = 0.03(2), 856 Bijvoet pairs
;
_refine_ls_abs_structure_Flack     0.00(6)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2008)'
_computing_data_reduction     'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material     'WinGX (Farrugia, 2012)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C2 0.61881(11) 0.39839(13) -0.1020(3) 0.0241(5) Uani d . 1 1 . .
    H H2 0.5556 0.4068 -0.0918 0.029 Uiso calc R 1 1 . .
    C C4 0.76184(13) 0.41464(15) -0.2179(4) 0.0308(5) Uani d . 1 1 . .
    H H4 0.8131 0.4368 -0.3039 0.037 Uiso calc R 1 1 . .
    C C3 0.76136(12) 0.34674(15) -0.0291(4) 0.0303(4) Uani d . 1 1 . .
    H H3 0.8120 0.3132 0.0402 0.036 Uiso calc R 1 1 . .
    N N3 0.54484(10) 0.08365(11) 0.8199(3) 0.0274(3) Uani d U 1 1 . .
    N N2 0.67050(9) 0.33611(11) 0.0429(3) 0.0210(3) Uani d . 1 1 . .
    N N1 0.67229(10) 0.44554(12) -0.2608(3) 0.0251(3) Uani d . 1 1 . .
    O O1 0.46671(9) 0.09724(10) 0.8910(3) 0.0323(4) Uani d U 1 1 . .
    O O2 0.59895(10) 0.01721(12) 0.9069(3) 0.0406(4) Uani d . 1 1 . .
    H H1 0.6548(14) 0.4898(17) -0.386(4) 0.030(5) Uiso d . 1 1 . .
    Cl Cl1 0.88518(2) 0.09410(3) 0.84010(10) 0.02647(12) Uani d . 1 1 . .
    C C8 0.57713(11) 0.14961(13) 0.6161(3) 0.0217(3) Uani d . 1 1 . .
    C C9 0.66889(12) 0.14545(14) 0.5571(4) 0.0303(4) Uani d . 1 1 . .
    H H9 0.7093 0.1022 0.6443 0.036 Uiso calc R 1 1 . .
    C C10 0.69939(11) 0.20704(13) 0.3655(4) 0.0300(4) Uani d . 1 1 . .
    H H10 0.7608 0.2048 0.3216 0.036 Uiso calc R 1 1 . .
    C C5 0.63843(11) 0.27213(12) 0.2387(3) 0.0204(3) Uani d . 1 1 . .
    C C6 0.54623(11) 0.27679(13) 0.3038(4) 0.0264(4) Uani d . 1 1 . .
    H H6 0.5058 0.3212 0.2196 0.032 Uiso calc R 1 1 . .
    C C7 0.51553(11) 0.21484(13) 0.4943(4) 0.0260(4) Uani d . 1 1 . .
    H H7 0.4543 0.2170 0.5397 0.031 Uiso calc R 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C2 N1 . 1.316(2) ?
    C2 N2 . 1.343(2) ?
    C2 H2 . 0.9300 ?
    C4 C3 . 1.343(3) ?
    C4 N1 . 1.382(2) ?
    C4 H4 . 0.9300 ?
    C3 N2 . 1.393(2) ?
    C3 H3 . 0.9300 ?
    N3 O1 . 1.220(2) ?
    N3 O2 . 1.232(2) ?
    N3 C8 . 1.474(2) ?
    N2 C5 . 1.425(2) ?
    N1 H1 . 0.92(2) ?
    C8 C7 . 1.381(2) ?
    C8 C9 . 1.381(2) ?
    C9 C10 . 1.384(3) ?
    C9 H9 . 0.9300 ?
    C10 C5 . 1.388(2) ?
    C10 H10 . 0.9300 ?
    C5 C6 . 1.396(2) ?
    C6 C7 . 1.382(3) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 C2 N2 . . 108.78(15) ?
    N1 C2 H2 . . 125.6 ?
    N2 C2 H2 . . 125.6 ?
    C3 C4 N1 . . 107.45(16) ?
    C3 C4 H4 . . 126.3 ?
    N1 C4 H4 . . 126.3 ?
    C4 C3 N2 . . 106.90(16) ?
    C4 C3 H3 . . 126.5 ?
    N2 C3 H3 . . 126.5 ?
    O1 N3 O2 . . 124.04(17) ?
    O1 N3 C8 . . 118.59(14) ?
    O2 N3 C8 . . 117.37(15) ?
    C2 N2 C3 . . 107.90(15) ?
    C2 N2 C5 . . 126.14(14) ?
    C3 N2 C5 . . 125.95(15) ?
    C2 N1 C4 . . 108.96(16) ?
    C2 N1 H1 . . 127.3(13) ?
    C4 N1 H1 . . 123.7(13) ?
    C7 C8 C9 . . 122.31(17) ?
    C7 C8 N3 . . 119.25(15) ?
    C9 C8 N3 . . 118.43(16) ?
    C8 C9 C10 . . 118.58(16) ?
    C8 C9 H9 . . 120.7 ?
    C10 C9 H9 . . 120.7 ?
    C9 C10 C5 . . 120.04(15) ?
    C9 C10 H10 . . 120.0 ?
    C5 C10 H10 . . 120.0 ?
    C10 C5 C6 . . 120.53(17) ?
    C10 C5 N2 . . 119.73(15) ?
    C6 C5 N2 . . 119.73(15) ?
    C7 C6 C5 . . 119.50(15) ?
    C7 C6 H6 . . 120.2 ?
    C5 C6 H6 . . 120.2 ?
    C8 C7 C6 . . 119.02(16) ?
    C8 C7 H7 . . 120.5 ?
    C6 C7 H7 . . 120.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N1 C4 C3 N2 . . . . 0.1(2) ?
    N1 C2 N2 C3 . . . . 0.8(2) ?
    N1 C2 N2 C5 . . . . 179.69(15) ?
    C4 C3 N2 C2 . . . . -0.6(2) ?
    C4 C3 N2 C5 . . . . -179.45(15) ?
    N2 C2 N1 C4 . . . . -0.7(2) ?
    C3 C4 N1 C2 . . . . 0.4(2) ?
    O1 N3 C8 C7 . . . . -7.6(2) ?
    O2 N3 C8 C7 . . . . 171.90(17) ?
    O1 N3 C8 C9 . . . . 171.10(16) ?
    O2 N3 C8 C9 . . . . -9.4(2) ?
    C7 C8 C9 C10 . . . . -1.5(3) ?
    N3 C8 C9 C10 . . . . 179.81(16) ?
    C8 C9 C10 C5 . . . . 0.7(3) ?
    C9 C10 C5 C6 . . . . 0.4(3) ?
    C9 C10 C5 N2 . . . . 179.43(17) ?
    C2 N2 C5 C10 . . . . 176.61(17) ?
    C3 N2 C5 C10 . . . . -4.7(3) ?
    C2 N2 C5 C6 . . . . -4.4(3) ?
    C3 N2 C5 C6 . . . . 174.27(17) ?
    C10 C5 C6 C7 . . . . -0.8(3) ?
    N2 C5 C6 C7 . . . . -179.81(15) ?
    C9 C8 C7 C6 . . . . 1.1(3) ?
    N3 C8 C7 C6 . . . . 179.81(16) ?
    C5 C6 C7 C8 . . . . 0.0(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1 Cl1 4_653 0.92(2) 2.08(2) 2.9976(17) 178(2)
    C9 H9 Cl1 1 0.93 2.80 3.5898(19) 144.1
    C2 H2 Cl1 3_454 0.93 2.52 3.4286(17) 166.1
    C4 H4 O2 4_653 0.93 2.29 3.181(2) 160.6
