#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/77/2017707.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_2017707
loop_
_publ_author_name
'Meng, Gao-Xiang'
'Yang, He-Lin'
'Cheng, Cui-Xia'
'Huang, Xin-Tang'
_publ_section_title
;
 Two-dimensional networks in 2-methylanilinium picrate and
 2,5-dichloroanilinium picrate
;
_journal_coeditor_code           GD3342
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o337
_journal_page_last               o340
_journal_paper_doi               10.1107/S0108270110020846
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C7 H10 N + , C6 H2 N3 O7 -'
_chemical_formula_moiety         'C7 H10 N + , C6 H2 N3 O7 -'
_chemical_formula_sum            'C13 H12 N4 O7'
_chemical_formula_weight         336.27
_chemical_name_systematic
;
2-methylanilinium picrate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.269(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6501(3)
_cell_length_b                   16.4813(4)
_cell_length_c                   7.5754(2)
_cell_measurement_reflns_used    1547
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.15
_cell_volume                     1450.51(6)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.3° wide ω exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed Siemens Mo tube'
_diffrn_radiation_type           'Mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9575
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0666
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[s²(Fo²)+(0.0785P)²+1.5344P] where  P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1720
_reflns_number_gt                2267
_reflns_number_total             2852
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3342.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017707
_cod_database_fobs_code          2017707
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_disorder_assembly
_atom_site_disorder_group
C C1 0.5876(2) 0.24890(17) 0.4978(4) 0.0124(6) Uani d . 1 . .
C C2 0.5032(2) 0.19308(18) 0.5370(4) 0.0140(6) Uani d . 1 . .
C C3 0.3990(2) 0.22580(19) 0.5852(4) 0.0178(7) Uani d . 1 . .
H H3 0.3383 0.1902 0.6109 0.021 Uiso calc R 1 . .
C C4 0.3824(2) 0.30889(19) 0.5964(4) 0.0193(7) Uani d . 1 . .
H H4 0.3115 0.3292 0.6323 0.023 Uiso calc R 1 . .
C C5 0.4686(2) 0.36292(18) 0.5556(4) 0.0181(7) Uani d . 1 . .
H H5 0.4565 0.4198 0.5622 0.022 Uiso calc R 1 . .
C C6 0.5728(2) 0.33255(18) 0.5049(4) 0.0168(6) Uani d . 1 . .
H H6 0.6325 0.3683 0.4757 0.020 Uiso calc R 1 . .
C C7 0.9026(2) 0.12291(17) 0.7829(4) 0.0129(6) Uani d . 1 . .
C C8 1.0156(2) 0.15881(17) 0.8107(4) 0.0144(6) Uani d . 1 . .
C C9 1.1170(2) 0.11606(18) 0.8051(4) 0.0146(6) Uani d . 1 . .
H H9 1.1891 0.1430 0.8214 0.018 Uiso calc R 1 . .
C C10 1.1120(2) 0.03303(18) 0.7752(4) 0.0151(6) Uani d . 1 . .
C C11 1.0069(2) -0.00764(17) 0.7478(4) 0.0139(6) Uani d . 1 . .
H H11 1.0042 -0.0642 0.7243 0.017 Uiso calc R 1 . .
C C12 0.9083(2) 0.03654(17) 0.7560(4) 0.0128(6) Uani d . 1 . .
C C13 0.5217(2) 0.10246(18) 0.5298(4) 0.0183(7) Uani d . 1 . .
H H13A 0.5460 0.0875 0.4131 0.027 Uiso calc R 1 . .
H H13B 0.4496 0.0745 0.5503 0.027 Uiso calc R 1 . .
H H13C 0.5813 0.0866 0.6213 0.027 Uiso calc R 1 . .
N N1 0.7004(2) 0.21749(16) 0.4502(4) 0.0145(5) Uani d . 1 . .
H H1C 0.689(3) 0.174(2) 0.375(5) 0.017 Uiso d . 1 . .
H H1A 0.745(3) 0.197(2) 0.560(5) 0.017 Uiso d . 1 . .
H H1B 0.741(3) 0.258(2) 0.403(5) 0.017 Uiso d . 1 . .
N N2 1.0252(2) 0.24733(15) 0.8351(4) 0.0189(6) Uani d . 1 . .
N N3 1.21805(19) -0.01227(15) 0.7659(3) 0.0174(6) Uani d . 1 . .
N N4 0.79761(19) -0.00660(14) 0.7297(3) 0.0133(5) Uani d . 1 . .
O O1 0.80771(16) 0.16211(12) 0.7685(3) 0.0155(5) Uani d . 1 . .
O O2 0.95267(17) 0.28171(13) 0.9192(3) 0.0253(6) Uani d . 1 . .
O O3 1.10521(19) 0.28239(14) 0.7711(4) 0.0344(7) Uani d . 1 . .
O O4 1.31051(16) 0.02380(13) 0.7795(3) 0.0204(5) Uani d . 1 . .
O O5 1.20952(18) -0.08698(13) 0.7414(3) 0.0286(6) Uani d . 1 . .
O O6 0.78077(18) -0.05062(14) 0.5981(3) 0.0251(6) Uani d . 1 . .
O O7 0.72885(17) 0.00209(13) 0.8446(3) 0.0214(5) Uani d . 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'
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
C6 C1 C2 . . 123.6(3) ?
C6 C1 N1 . . 118.1(2) ?
C2 C1 N1 . . 118.3(2) ?
C1 C2 C3 . . 116.1(3) ?
C1 C2 C13 . . 122.7(2) ?
C3 C2 C13 . . 121.2(3) ?
C4 C3 C2 . . 121.6(3) ?
C4 C3 H3 . . 119.2 ?
C2 C3 H3 . . 119.2 ?
C3 C4 C5 . . 120.7(3) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C6 C5 C4 . . 119.2(3) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
C1 C6 C5 . . 118.7(3) ?
C1 C6 H6 . . 120.6 ?
C5 C6 H6 . . 120.6 ?
O1 C7 C12 . . 122.4(2) ?
O1 C7 C8 . . 125.4(3) ?
C12 C7 C8 . . 112.0(2) ?
C9 C8 C7 . . 124.0(3) ?
C9 C8 N2 . . 116.9(2) ?
C7 C8 N2 . . 118.9(2) ?
C8 C9 C10 . . 118.9(2) ?
C8 C9 H9 . . 120.5 ?
C10 C9 H9 . . 120.5 ?
C9 C10 C11 . . 121.5(3) ?
C9 C10 N3 . . 119.4(2) ?
C11 C10 N3 . . 119.1(3) ?
C12 C11 C10 . . 117.9(3) ?
C12 C11 H11 . . 121.0 ?
C10 C11 H11 . . 121.0 ?
C11 C12 C7 . . 125.5(2) ?
C11 C12 N4 . . 117.9(2) ?
C7 C12 N4 . . 116.6(2) ?
C2 C13 H13A . . 109.5 ?
C2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C1 N1 H1C . . 109(2) ?
C1 N1 H1A . . 109.5(18) ?
H1C N1 H1A . . 107(3) ?
C1 N1 H1B . . 110(2) ?
H1C N1 H1B . . 113(3) ?
H1A N1 H1B . . 109(3) ?
O3 N2 O2 . . 123.9(3) ?
O3 N2 C8 . . 118.0(2) ?
O2 N2 C8 . . 118.1(2) ?
O4 N3 O5 . . 123.4(2) ?
O4 N3 C10 . . 119.5(2) ?
O5 N3 C10 . . 117.2(2) ?
O7 N4 O6 . . 124.3(2) ?
O7 N4 C12 . . 117.1(2) ?
O6 N4 C12 . . 118.5(2) ?
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 C6 . 1.391(4) ?
C1 C2 . 1.395(4) ?
C1 N1 . 1.481(3) ?
C2 C3 . 1.401(4) ?
C2 C13 . 1.511(4) ?
C3 C4 . 1.386(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.395(4) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.392(4) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 O1 . 1.278(3) ?
C7 C12 . 1.440(4) ?
C7 C8 . 1.444(4) ?
C8 C9 . 1.379(4) ?
C8 N2 . 1.474(4) ?
C9 C10 . 1.388(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.398(4) ?
C10 N3 . 1.450(3) ?
C11 C12 . 1.366(4) ?
C11 H11 . 0.9500 ?
C12 N4 . 1.473(3) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
N1 H1C . 0.92(4) ?
N1 H1A . 1.00(3) ?
N1 H1B . 0.91(4) ?
N2 O3 . 1.227(3) ?
N2 O2 . 1.233(3) ?
N3 O4 . 1.228(3) ?
N3 O5 . 1.248(3) ?
N4 O7 . 1.235(3) ?
N4 O6 . 1.236(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
_geom_hbond_publ_flag
N1 H1A O1 . 1.00(3) 1.79(4) 2.786(3) 172(3) yes
N1 H1B O1 4_565 0.91(4) 1.86(4) 2.767(3) 170(3) yes
N1 H1C O5 3_756 0.92(4) 2.10(3) 2.840(3) 137(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
C6 C1 C2 C3 . . . . 0.1(4) ?
N1 C1 C2 C3 . . . . 178.6(3) ?
C6 C1 C2 C13 . . . . -179.5(3) ?
N1 C1 C2 C13 . . . . -1.1(4) ?
C1 C2 C3 C4 . . . . -1.3(4) ?
C13 C2 C3 C4 . . . . 178.4(3) ?
C2 C3 C4 C5 . . . . 1.6(5) ?
C3 C4 C5 C6 . . . . -0.7(5) ?
C2 C1 C6 C5 . . . . 0.7(5) ?
N1 C1 C6 C5 . . . . -177.7(3) ?
C4 C5 C6 C1 . . . . -0.4(4) ?
O1 C7 C8 C9 . . . . -172.0(3) ?
C12 C7 C8 C9 . . . . 2.4(4) ?
O1 C7 C8 N2 . . . . 3.7(4) ?
C12 C7 C8 N2 . . . . 178.2(3) ?
C7 C8 C9 C10 . . . . -1.6(5) ?
N2 C8 C9 C10 . . . . -177.4(3) ?
C8 C9 C10 C11 . . . . 1.1(4) ?
C8 C9 C10 N3 . . . . 178.9(3) ?
C9 C10 C11 C12 . . . . -1.7(4) ?
N3 C10 C11 C12 . . . . -179.5(3) ?
C10 C11 C12 C7 . . . . 2.9(4) ?
C10 C11 C12 N4 . . . . -179.1(3) ?
O1 C7 C12 C11 . . . . 171.5(3) ?
C8 C7 C12 C11 . . . . -3.2(4) ?
O1 C7 C12 N4 . . . . -6.5(4) ?
C8 C7 C12 N4 . . . . 178.9(2) ?
C9 C8 N2 O3 . . . . 32.8(4) ?
C7 C8 N2 O3 . . . . -143.3(3) ?
C9 C8 N2 O2 . . . . -146.9(3) ?
C7 C8 N2 O2 . . . . 37.1(4) ?
C9 C10 N3 O4 . . . . -2.1(4) ?
C11 C10 N3 O4 . . . . 175.7(3) ?
C9 C10 N3 O5 . . . . 179.0(3) ?
C11 C10 N3 O5 . . . . -3.2(4) ?
C11 C12 N4 O7 . . . . 127.0(3) ?
C7 C12 N4 O7 . . . . -54.9(3) ?
C11 C12 N4 O6 . . . . -51.0(4) ?
C7 C12 N4 O6 . . . . 127.1(3) ?
