##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
2-Amino-1-(4-nitrobenzyl)pyridinium bromide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H12 O2 N3 + , Br -'
_chemical_formula_sum     'C12 H12 Br1 N3 O2'
_chemical_formula_iupac     'C12 H12 O2 N3 + , Br -'
_chemical_formula_weight     310.16
_chemical_melting_point     518
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c n'
_symmetry_space_group_name_Hall     '-P 2n 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z+1/2'
    '-x, y, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y-1/2, -z-1/2'
    'x, -y, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     8.0505(6)
_cell_length_b     14.0971(10)
_cell_length_c     21.8990(15)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2485.3(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     6556
_cell_measurement_theta_min     2.69
_cell_measurement_theta_max     26.57
_cell_measurement_temperature     273(2)
_exptl_crystal_description     'Block'
_exptl_crystal_colour     'Colourless'
_exptl_crystal_size_max     0.10
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.658
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1248
_exptl_absorpt_coefficient_mu     3.306
_exptl_absorpt_correction_type     none
_exptl_special_details
;
;
_diffrn_ambient_temperature     273(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 APEX CCD area-detector'
_diffrn_measurement_device     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16442
_diffrn_reflns_av_R_equivalents     0.0412
_diffrn_reflns_av_sigmaI/netI     0.0303
_diffrn_reflns_theta_min     1.86
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 > 2sigma(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     2203
_reflns_number_gt     1899
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0387
_refine_ls_R_factor_gt     0.0317
_refine_ls_wR_factor_gt     0.0804
_refine_ls_wR_factor_ref     0.0847
_refine_ls_goodness_of_fit_ref     1.065
_refine_ls_restrained_S_all     1.065
_refine_ls_number_reflns     2203
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0323P)²+2.4183P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.427
_refine_diff_density_min     -0.471
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.0062(5)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'DIRDIF99 (Beurskens et al.,  1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                              'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL97 and PARST (Nardelli, 1995)'
loop_
    _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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    Br1 1.01693(4) -0.09384(2) 0.105125(15) 0.05078(16) Uani d . 1 . . Br
    C1 0.6431(3) 0.09972(17) 0.03121(12) 0.0345(6) Uani d . 1 . . C
    C2 0.5791(4) 0.14921(19) -0.01942(12) 0.0408(6) Uani d . 1 . . C
    H2 0.6504 0.1700 -0.0500 0.049 Uiso calc R 1 . . H
    C3 0.4136(4) 0.1667(2) -0.02373(13) 0.0466(7) Uani d . 1 . . C
    H3 0.3720 0.1997 -0.0572 0.056 Uiso calc R 1 . . H
    C4 0.3060(4) 0.1354(2) 0.02168(15) 0.0508(8) Uani d . 1 . . C
    H4 0.1927 0.1474 0.0190 0.061 Uiso calc R 1 . . H
    C5 0.3683(4) 0.0876(2) 0.06956(14) 0.0456(7) Uani d . 1 . . C
    H5 0.2967 0.0661 0.0999 0.055 Uiso calc R 1 . . H
    C6 0.5944(4) 0.01860(19) 0.12924(11) 0.0394(6) Uani d . 1 . . C
    H6A 0.6813 -0.0252 0.1172 0.047 Uiso calc R 1 . . H
    H6B 0.5035 -0.0183 0.1460 0.047 Uiso calc R 1 . . H
    C7 0.6608(3) 0.08365(17) 0.17824(11) 0.0333(6) Uani d . 1 . . C
    C8 0.7423(4) 0.0422(2) 0.22713(12) 0.0424(6) Uani d . 1 . . C
    H8 0.7529 -0.0234 0.2287 0.051 Uiso calc R 1 . . H
    C9 0.8079(4) 0.0966(2) 0.27336(13) 0.0438(7) Uani d . 1 . . C
    H9 0.8619 0.0687 0.3063 0.053 Uiso calc R 1 . . H
    C10 0.7912(3) 0.1934(2) 0.26936(12) 0.0403(7) Uani d . 1 . . C
    C11 0.7089(4) 0.2367(2) 0.22200(13) 0.0439(7) Uani d . 1 . . C
    H11 0.6978 0.3023 0.2208 0.053 Uiso calc R 1 . . H
    C12 0.6430(4) 0.18091(19) 0.17625(12) 0.0403(6) Uani d . 1 . . C
    H12 0.5863 0.2090 0.1440 0.048 Uiso calc R 1 . . H
    N1 0.5351(3) 0.06982(16) 0.07470(10) 0.0355(5) Uani d . 1 . . N
    N2 0.8053(3) 0.08377(17) 0.03638(11) 0.0441(6) Uani d . 1 . . N
    H2A 0.8433 0.0541 0.0677 0.053 Uiso calc R 1 . . H
    H2B 0.8721 0.1032 0.0084 0.053 Uiso calc R 1 . . H
    N3 0.8684(3) 0.2529(2) 0.31648(12) 0.0568(7) Uani d . 1 . . N
    O1 0.8792(4) 0.3374(2) 0.30749(12) 0.0800(8) Uani d . 1 . . O
    O2 0.9211(4) 0.2134(2) 0.36222(11) 0.0787(8) Uani d . 1 . . O
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Br1 0.0479(2) 0.0596(2) 0.0448(2) 0.00445(14) 0.00594(13) 0.01166(14)
    C1 0.0395(14) 0.0344(13) 0.0295(13) -0.0054(11) 0.0001(11) -0.0055(11)
    C2 0.0516(17) 0.0406(15) 0.0301(14) -0.0005(13) -0.0016(13) 0.0007(11)
    C3 0.0562(18) 0.0428(16) 0.0407(16) 0.0062(14) -0.0117(14) -0.0060(13)
    C4 0.0389(16) 0.0561(18) 0.0574(19) 0.0038(14) -0.0090(15) -0.0160(16)
    C5 0.0397(16) 0.0547(18) 0.0423(17) -0.0069(13) 0.0065(13) -0.0109(14)
    C6 0.0520(16) 0.0367(14) 0.0296(13) -0.0078(12) 0.0043(13) 0.0017(11)
    C7 0.0374(14) 0.0368(14) 0.0256(12) -0.0031(11) 0.0058(11) 0.0000(10)
    C8 0.0542(17) 0.0396(14) 0.0333(14) 0.0049(13) 0.0043(13) 0.0020(12)
    C9 0.0436(16) 0.0622(19) 0.0257(13) 0.0064(14) 0.0027(12) 0.0024(13)
    C10 0.0358(15) 0.0570(17) 0.0280(13) -0.0061(13) 0.0048(11) -0.0117(13)
    C11 0.0525(17) 0.0372(14) 0.0419(15) -0.0039(13) 0.0026(14) -0.0051(13)
    C12 0.0479(16) 0.0397(15) 0.0331(14) -0.0006(12) -0.0046(12) 0.0010(12)
    N1 0.0390(12) 0.0404(12) 0.0271(11) -0.0075(10) -0.0003(9) -0.0041(9)
    N2 0.0389(13) 0.0564(15) 0.0370(13) -0.0039(11) 0.0006(10) 0.0086(11)
    N3 0.0460(15) 0.087(2) 0.0375(15) -0.0143(14) 0.0080(12) -0.0219(15)
    O1 0.095(2) 0.0741(18) 0.0704(17) -0.0275(16) -0.0020(15) -0.0289(14)
    O2 0.0804(18) 0.119(2) 0.0369(13) -0.0151(17) -0.0124(13) -0.0173(14)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    C1 N2 . 1.330(3) ?
    C1 N1 . 1.357(3) ?
    C1 C2 . 1.408(4) ?
    C2 C3 . 1.359(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.390(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.343(4) ?
    C4 H4 . 0.9300 ?
    C5 N1 . 1.370(4) ?
    C5 H5 . 0.9300 ?
    C6 N1 . 1.475(3) ?
    C6 C7 . 1.509(4) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C12 . 1.379(4) ?
    C7 C8 . 1.385(4) ?
    C8 C9 . 1.375(4) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.374(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.374(4) ?
    C10 N3 . 1.468(4) ?
    C11 C12 . 1.380(4) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 0.9300 ?
    N2 H2A . 0.8600 ?
    N2 H2B . 0.8600 ?
    N3 O1 . 1.211(4) ?
    N3 O2 . 1.222(4) ?
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
    N2 C1 N1 . . 121.1(2) ?
    N2 C1 C2 . . 120.7(3) ?
    N1 C1 C2 . . 118.2(2) ?
    C3 C2 C1 . . 120.2(3) ?
    C3 C2 H2 . . 119.9 ?
    C1 C2 H2 . . 119.9 ?
    C2 C3 C4 . . 120.2(3) ?
    C2 C3 H3 . . 119.9 ?
    C4 C3 H3 . . 119.9 ?
    C5 C4 C3 . . 119.0(3) ?
    C5 C4 H4 . . 120.5 ?
    C3 C4 H4 . . 120.5 ?
    C4 C5 N1 . . 121.4(3) ?
    C4 C5 H5 . . 119.3 ?
    N1 C5 H5 . . 119.3 ?
    N1 C6 C7 . . 113.1(2) ?
    N1 C6 H6A . . 109.0 ?
    C7 C6 H6A . . 109.0 ?
    N1 C6 H6B . . 109.0 ?
    C7 C6 H6B . . 109.0 ?
    H6A C6 H6B . . 107.8 ?
    C12 C7 C8 . . 119.5(2) ?
    C12 C7 C6 . . 123.0(2) ?
    C8 C7 C6 . . 117.5(2) ?
    C9 C8 C7 . . 121.1(3) ?
    C9 C8 H8 . . 119.5 ?
    C7 C8 H8 . . 119.5 ?
    C10 C9 C8 . . 118.0(3) ?
    C10 C9 H9 . . 121.0 ?
    C8 C9 H9 . . 121.0 ?
    C11 C10 C9 . . 122.5(3) ?
    C11 C10 N3 . . 118.8(3) ?
    C9 C10 N3 . . 118.8(3) ?
    C10 C11 C12 . . 118.7(3) ?
    C10 C11 H11 . . 120.6 ?
    C12 C11 H11 . . 120.6 ?
    C7 C12 C11 . . 120.2(3) ?
    C7 C12 H12 . . 119.9 ?
    C11 C12 H12 . . 119.9 ?
    C1 N1 C5 . . 120.9(2) ?
    C1 N1 C6 . . 120.9(2) ?
    C5 N1 C6 . . 118.2(2) ?
    C1 N2 H2A . . 120.0 ?
    C1 N2 H2B . . 120.0 ?
    H2A N2 H2B . . 120.0 ?
    O1 N3 O2 . . 123.8(3) yes
    O1 N3 C10 . . 118.6(3) yes
    O2 N3 C10 . . 117.6(3) yes
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
    N2 C1 C2 C3 . . . . -178.8(2) ?
    N1 C1 C2 C3 . . . . 0.5(4) ?
    C1 C2 C3 C4 . . . . -0.3(4) ?
    C2 C3 C4 C5 . . . . -0.2(4) ?
    C3 C4 C5 N1 . . . . 0.5(4) ?
    N1 C6 C7 C12 . . . . 9.9(4) yes
    N1 C6 C7 C8 . . . . -170.4(2) yes
    C12 C7 C8 C9 . . . . -0.9(4) ?
    C6 C7 C8 C9 . . . . 179.4(3) ?
    C7 C8 C9 C10 . . . . -0.5(4) ?
    C8 C9 C10 C11 . . . . 1.5(4) ?
    C8 C9 C10 N3 . . . . -176.6(2) ?
    C9 C10 C11 C12 . . . . -1.1(4) ?
    N3 C10 C11 C12 . . . . 177.1(2) ?
    C8 C7 C12 C11 . . . . 1.3(4) ?
    C6 C7 C12 C11 . . . . -178.9(3) ?
    C10 C11 C12 C7 . . . . -0.4(4) ?
    N2 C1 N1 C5 . . . . 179.1(2) ?
    C2 C1 N1 C5 . . . . -0.2(4) ?
    N2 C1 N1 C6 . . . . 0.0(4) ?
    C2 C1 N1 C6 . . . . -179.3(2) ?
    C4 C5 N1 C1 . . . . -0.3(4) ?
    C4 C5 N1 C6 . . . . 178.8(3) ?
    C7 C6 N1 C1 . . . . 81.4(3) ?
    C7 C6 N1 C5 . . . . -97.7(3) ?
    C11 C10 N3 O1 . . . . -11.1(4) ?
    C9 C10 N3 O1 . . . . 167.1(3) ?
    C11 C10 N3 O2 . . . . 170.3(3) ?
    C9 C10 N3 O2 . . . . -11.5(4) ?
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
    N2 H2A Br1 1 0.86 2.64 3.382(2) 145
    N2 H2B Br1 5_755 0.86 2.65 3.416(2) 150
data_global
_journal_date_recd_electronic     2005-11-17
_journal_date_accepted     2005-11-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      1
_journal_page_first     o74
_journal_page_last     o76
_journal_paper_category     EO
_journal_coeditor_code     CV6613
_publ_contact_author_name     'Dr V. Parthasarathi'
_publ_contact_author_address
;
School of Physics
Bharathidasan University
Tiruchirappalli 620 024
India
;
_publ_contact_author_email     vpsarati@yahoo.com
_publ_contact_author_fax     '+91-431-2407045'
_publ_contact_author_phone     '+91-431-2407057'
_publ_section_title
;
2-Amino-1-(4-nitrobenzyl)pyridinium bromide
;
loop_
    _publ_author_name
    _publ_author_address
    'Sundar, T. V.'
;
School of Physics
Bharathidasan University
Tiruchirappalli 620 024
India
;
    'Parthasarathi, V.'
;
School of Physics
Bharathidasan University
Tiruchirappalli 620 024
India
;
    'Sridhar, B.'
;
Laboratory of X-ray Crystallography
Indian Institute of Chemical Technology
Hyderabad 500 007
India
;
    'Venkatesan, P.'
;
School of Chemistry
Bharathidasan University
Tiruchirappalli 620 024
India
;
    'Nallu, M.'
;
School of Chemistry
Bharathidasan University
Tiruchirappalli 620 024
India
;
