##############################################################################
#                                                                            #
# 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
_audit_creation_method     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-07-07
_journal_date_accepted     2012-09-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue     10
_journal_page_first     o2941
_journal_page_last     o2941
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812038834
_journal_coeditor_code     CV5319
_publ_contact_author_name     'Doraisamyraja Kalaivani'
_publ_contact_author_address
;
PG and Research Department of Chemistry
Seethalakshmi Ramaswami College,
Tiruchirappalli 620 002,
Tamil Nadu, India
;
_publ_contact_author_email     kalaivbalaj@yahoo.co.in
_publ_contact_author_phone        .91E-306
_publ_section_title
;
1-(5-Amino-2,4-dinitrophenyl)pyridinium chloride monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Rajamanickam Babykala'
;
     PG and Research Department of Chemistry
     Seethalakshmi Ramaswami College,
     Tiruchirappalli 620 002, Tamil Nadu, India
;
    'Doraisamyraja Kalaivani'
;
      PG and Research Department of Chemistry
      Seethalakshmi Ramaswami College,
      Tiruchirappalli 620 002, Tamil Nadu, India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-(5-Amino-2,4-dinitrophenyl)pyridinium chloride monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H9 N4 O4 +, Cl -, H2 O'
_chemical_formula_sum     'C11 H11 Cl N4 O5'
_chemical_formula_iupac     'C11 H9 N4 O4 +, Cl -, H2 O'
_chemical_formula_weight     314.69
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     5.4312(4)
_cell_length_b     21.493(2)
_cell_length_c     11.3892(9)
_cell_angle_alpha     90.00
_cell_angle_beta     92.362(3)
_cell_angle_gamma     90.00
_cell_volume     1328.33(19)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4581
_cell_measurement_theta_min     2.60
_cell_measurement_theta_max     25.43
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.574
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     648
_exptl_absorpt_coefficient_mu     0.317
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2004)'
_exptl_absorpt_correction_T_min     0.8709
_exptl_absorpt_correction_T_max     0.9393
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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 Kappa APEXII CCD diffractometer'
_diffrn_measurement_method     'ω and φ scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     14754
_diffrn_reflns_av_R_equivalents     0.0308
_diffrn_reflns_av_sigmaI/netI     0.0241
_diffrn_reflns_theta_min     2.61
_diffrn_reflns_theta_max     27.87
_diffrn_reflns_theta_full     27.87
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -28
_diffrn_reflns_limit_k_max     28
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     ?
_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 >
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     3125
_reflns_number_gt     2288
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0571
_refine_ls_R_factor_gt     0.0383
_refine_ls_wR_factor_gt     0.0999
_refine_ls_wR_factor_ref     0.1117
_refine_ls_goodness_of_fit_ref     1.031
_refine_ls_restrained_S_all     1.031
_refine_ls_number_reflns     3125
_refine_ls_number_parameters     224
_refine_ls_number_restraints     9
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0538P)²+0.2604P] 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     0.195
_refine_diff_density_min     -0.265
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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, 2004)'
_computing_cell_refinement     'APEX2 and SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT and XPREP (Bruker, 2004)'
_computing_structure_solution     'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
             'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material     'PLATON (Spek, 2009)'
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 C1 0.3483(3) 0.66419(8) 0.10183(14) 0.0449(4) Uani d . 1 1 . .
    H H1 0.4780 0.6878 0.1336 0.054 Uiso calc R 1 1 . .
    C C2 0.3105(3) 0.66065(9) -0.01760(15) 0.0531(4) Uani d . 1 1 . .
    H H2 0.4149 0.6814 -0.0671 0.064 Uiso calc R 1 1 . .
    C C3 0.1174(4) 0.62626(9) -0.06342(15) 0.0563(5) Uani d . 1 1 . .
    H H3 0.0871 0.6242 -0.1443 0.068 Uiso calc R 1 1 . .
    C C4 -0.0302(4) 0.59508(11) 0.01082(17) 0.0663(6) Uani d . 1 1 . .
    H H4 -0.1607 0.5712 -0.0194 0.080 Uiso calc R 1 1 . .
    C C5 0.0137(3) 0.59893(10) 0.12967(16) 0.0613(5) Uani d . 1 1 . .
    H H5 -0.0855 0.5773 0.1803 0.074 Uiso calc R 1 1 . .
    C C6 0.2469(3) 0.63860(8) 0.29921(13) 0.0403(4) Uani d . 1 1 . .
    C C7 0.1136(3) 0.67842(8) 0.37070(14) 0.0414(4) Uani d . 1 1 . .
    C C8 0.1804(3) 0.68200(8) 0.48832(14) 0.0441(4) Uani d . 1 1 . .
    H H8 0.0915 0.7076 0.5370 0.053 Uiso calc R 1 1 . .
    C C9 0.3760(3) 0.64842(8) 0.53520(13) 0.0432(4) Uani d . 1 1 . .
    C C10 0.5080(3) 0.60594(8) 0.46686(13) 0.0439(4) Uani d . 1 1 . .
    C C11 0.4326(3) 0.60318(8) 0.34576(14) 0.0446(4) Uani d . 1 1 . .
    H H11 0.5138 0.5761 0.2969 0.054 Uiso calc R 1 1 . .
    N N2 -0.0913(3) 0.71602(7) 0.32853(13) 0.0493(4) Uani d . 1 1 . .
    N N1 0.1997(2) 0.63388(6) 0.17294(11) 0.0404(3) Uani d . 1 1 . .
    N N3 0.4403(3) 0.65911(7) 0.65862(12) 0.0517(4) Uani d . 1 1 . .
    O O1 -0.1404(2) 0.71820(7) 0.22235(12) 0.0628(4) Uani d . 1 1 . .
    O O2 -0.2092(3) 0.74376(8) 0.40064(13) 0.0787(5) Uani d . 1 1 . .
    O O3 0.3182(3) 0.69609(7) 0.71230(11) 0.0676(4) Uani d . 1 1 . .
    O O4 0.6154(3) 0.63139(8) 0.70329(11) 0.0740(4) Uani d . 1 1 . .
    N N4 0.6928(3) 0.57003(8) 0.50422(14) 0.0560(4) Uani d D 1 1 . .
    O O5 0.3996(12) 0.4960(2) 0.1460(6) 0.0653(17) Uani d PD 0.555(13) 1 A 1
    O O5' 0.4978(12) 0.5075(2) 0.0942(7) 0.0622(16) Uani d PD 0.445(13) 1 B 2
    Cl Cl1 0.88637(9) 0.47657(2) 0.30769(4) 0.06455(18) Uani d . 1 1 . .
    H H5A 0.274(7) 0.487(3) 0.196(5) 0.15(2) Uiso d PD 0.555(13) 1 A 1
    H H5B 0.556(4) 0.494(4) 0.174(5) 0.15(2) Uiso d PD 0.555(13) 1 A 1
    H H5C 0.520(14) 0.481(3) 0.156(4) 0.08(3) Uiso d PD 0.445(13) 1 B 2
    H H5D 0.554(9) 0.499(3) 0.022(2) 0.064(16) Uiso d PD 0.445(13) 1 B 2
    H H4A 0.747(3) 0.5711(10) 0.5766(14) 0.063(6) Uiso d D 1 1 . .
    H H4B 0.759(4) 0.5437(9) 0.4563(18) 0.071(7) Uiso d D 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
    C1 N1 . 1.336(2) ?
    C1 C2 . 1.369(2) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.369(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.365(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.367(3) ?
    C4 H4 . 0.9300 ?
    C5 N1 . 1.336(2) ?
    C5 H5 . 0.9300 ?
    C6 C11 . 1.354(2) ?
    C6 C7 . 1.403(2) ?
    C6 N1 . 1.4540(19) ?
    C7 C8 . 1.375(2) ?
    C7 N2 . 1.442(2) ?
    C8 C9 . 1.374(2) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.414(2) ?
    C9 N3 . 1.4528(19) ?
    C10 N4 . 1.323(2) ?
    C10 C11 . 1.424(2) ?
    C11 H11 . 0.9300 ?
    N2 O2 . 1.2176(19) ?
    N2 O1 . 1.2285(18) ?
    N3 O4 . 1.2158(19) ?
    N3 O3 . 1.216(2) ?
    N4 H4A . 0.864(15) ?
    N4 H4B . 0.874(16) ?
    O5 H5A . 0.930(19) ?
    O5 H5B . 0.90(2) ?
    O5' H5C . 0.916(19) ?
    O5' H5D . 0.913(19) ?
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 C1 C2 . . 120.36(15) ?
    N1 C1 H1 . . 119.8 ?
    C2 C1 H1 . . 119.8 ?
    C3 C2 C1 . . 119.33(16) ?
    C3 C2 H2 . . 120.3 ?
    C1 C2 H2 . . 120.3 ?
    C4 C3 C2 . . 119.29(16) ?
    C4 C3 H3 . . 120.4 ?
    C2 C3 H3 . . 120.4 ?
    C3 C4 C5 . . 120.05(18) ?
    C3 C4 H4 . . 120.0 ?
    C5 C4 H4 . . 120.0 ?
    N1 C5 C4 . . 119.83(17) ?
    N1 C5 H5 . . 120.1 ?
    C4 C5 H5 . . 120.1 ?
    C11 C6 C7 . . 120.64(14) ?
    C11 C6 N1 . . 116.52(14) ?
    C7 C6 N1 . . 122.83(14) ?
    C8 C7 C6 . . 118.53(14) ?
    C8 C7 N2 . . 117.52(15) ?
    C6 C7 N2 . . 123.95(14) ?
    C9 C8 C7 . . 121.18(15) ?
    C9 C8 H8 . . 119.4 ?
    C7 C8 H8 . . 119.4 ?
    C8 C9 C10 . . 121.78(14) ?
    C8 C9 N3 . . 116.37(15) ?
    C10 C9 N3 . . 121.85(14) ?
    N4 C10 C9 . . 126.50(15) ?
    N4 C10 C11 . . 118.14(16) ?
    C9 C10 C11 . . 115.35(14) ?
    C6 C11 C10 . . 122.40(16) ?
    C6 C11 H11 . . 118.8 ?
    C10 C11 H11 . . 118.8 ?
    O2 N2 O1 . . 123.14(15) ?
    O2 N2 C7 . . 118.02(14) ?
    O1 N2 C7 . . 118.83(15) ?
    C1 N1 C5 . . 121.11(14) ?
    C1 N1 C6 . . 118.62(13) ?
    C5 N1 C6 . . 120.26(13) ?
    O4 N3 O3 . . 122.92(14) ?
    O4 N3 C9 . . 118.69(15) ?
    O3 N3 C9 . . 118.39(15) ?
    C10 N4 H4A . . 121.1(14) ?
    C10 N4 H4B . . 120.2(15) ?
    H4A N4 H4B . . 119(2) ?
    H5A O5 H5B . . 119(3) ?
    H5A O5 H5C . . 119(5) ?
    H5C O5' H5D . . 122(4) ?
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 C1 C2 C3 . . . . 0.7(3) ?
    C1 C2 C3 C4 . . . . -1.4(3) ?
    C2 C3 C4 C5 . . . . 0.7(3) ?
    C3 C4 C5 N1 . . . . 0.8(3) ?
    C11 C6 C7 C8 . . . . 1.9(2) ?
    N1 C6 C7 C8 . . . . -176.69(14) ?
    C11 C6 C7 N2 . . . . -177.90(15) ?
    N1 C6 C7 N2 . . . . 3.5(2) ?
    C6 C7 C8 C9 . . . . 1.2(2) ?
    N2 C7 C8 C9 . . . . -178.98(14) ?
    C7 C8 C9 C10 . . . . -3.9(2) ?
    C7 C8 C9 N3 . . . . 175.86(15) ?
    C8 C9 C10 N4 . . . . -177.62(17) ?
    N3 C9 C10 N4 . . . . 2.6(3) ?
    C8 C9 C10 C11 . . . . 3.3(2) ?
    N3 C9 C10 C11 . . . . -176.45(14) ?
    C7 C6 C11 C10 . . . . -2.4(2) ?
    N1 C6 C11 C10 . . . . 176.28(14) ?
    N4 C10 C11 C6 . . . . -179.34(16) ?
    C9 C10 C11 C6 . . . . -0.2(2) ?
    C8 C7 N2 O2 . . . . -7.3(2) ?
    C6 C7 N2 O2 . . . . 172.42(16) ?
    C8 C7 N2 O1 . . . . 173.29(15) ?
    C6 C7 N2 O1 . . . . -6.9(2) ?
    C2 C1 N1 C5 . . . . 0.9(3) ?
    C2 C1 N1 C6 . . . . 179.68(16) ?
    C4 C5 N1 C1 . . . . -1.6(3) ?
    C4 C5 N1 C6 . . . . 179.61(18) ?
    C11 C6 N1 C1 . . . . -78.17(19) ?
    C7 C6 N1 C1 . . . . 100.44(18) ?
    C11 C6 N1 C5 . . . . 100.64(19) ?
    C7 C6 N1 C5 . . . . -80.8(2) ?
    C8 C9 N3 O4 . . . . -178.50(16) ?
    C10 C9 N3 O4 . . . . 1.3(2) ?
    C8 C9 N3 O3 . . . . 0.6(2) ?
    C10 C9 N3 O3 . . . . -179.63(15) ?
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
    N4 H4A O4 . 0.864(15) 2.088(19) 2.671(2) 124.3(17)
    N4 H4B Cl1 . 0.874(16) 2.349(17) 3.2162(19) 171(2)
    N4 H4A Cl1 3_766 0.864(15) 2.556(18) 3.2268(16) 135.2(17)
    O5 H5B Cl1 . 0.90(2) 2.34(3) 3.187(3) 158(5)
    O5 H5A Cl1 1_455 0.930(19) 2.51(2) 3.429(9) 169(5)
    O5' H5D O5 3_665 0.913(19) 1.94(3) 2.815(16) 160(5)
