#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/61/2236151.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2236151
loop_
_publ_author_name
'Babykala, Rajamanickam'
'Kalaivani, Doraisamyraja'
_publ_section_title
;
 1-(5-Amino-2,4-dinitrophenyl)pyridinium chloride monohydrate
;
_journal_coeditor_code           CV5319
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2941
_journal_paper_doi               10.1107/S1600536812038834
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H9 N4 O4 +, Cl -, H2 O'
_chemical_formula_moiety         'C11 H9 N4 O4 +, Cl -, H2 O'
_chemical_formula_sum            'C11 H11 Cl N4 O5'
_chemical_formula_weight         314.69
_chemical_name_systematic
;
1-(5-Amino-2,4-dinitrophenyl)pyridinium chloride monohydrate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.362(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4312(4)
_cell_length_b                   21.493(2)
_cell_length_c                   11.3892(9)
_cell_measurement_reflns_used    4581
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.43
_cell_measurement_theta_min      2.60
_cell_volume                     1328.36(19)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14754
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.9393
_exptl_absorpt_correction_T_min  0.8709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.265
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0538P)²+0.2604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                2288
_reflns_number_total             3125
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5319.cif
_cod_data_source_block           I
_cod_original_cell_volume        1328.33(19)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236151
_cod_database_fobs_code          2236151
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'
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 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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)
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
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)
