#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/66/2226627.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_2226627
loop_
_publ_author_name
'Xu, Rui-jun'
_publ_section_title
;
 4-Methylanilinium 3,5-dinitrobenzoate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1574
_journal_paper_doi               10.1107/S1600536810018441
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C7 H10 N + , C7 H3 N2 O6 -'
_chemical_formula_moiety         'C7 H10 N + , C7 H3 N2 O6 -'
_chemical_formula_sum            'C14 H13 N3 O6'
_chemical_formula_weight         319.27
_chemical_name_systematic
;
4-methylanilinium 3,5-dinitrobenzoate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.790(4)
_cell_length_b                   7.2380(14)
_cell_length_c                   20.473(4)
_cell_measurement_reflns_used    11511
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.480
_cell_measurement_theta_min      2.995
_cell_volume                     2932.6(10)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0776
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            28284
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.16
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.224
_refine_ls_extinction_coef       0.0065(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0824P)²+0.9690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1587
_reflns_number_gt                2368
_reflns_number_total             3360
_reflns_threshold_expression     'I > 2.0 σ(I)'
_cod_data_source_file            pv2280.cif
_cod_data_source_block           I
_cod_original_cell_volume        2932.5(10)
_cod_database_code               2226627
_cod_database_fobs_code          2226627
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 C13 0.05834(9) 0.8208(3) 0.03041(9) 0.0389(4) Uani d . 1 . .
H H13 0.0302 0.7235 0.0424 0.047 Uiso calc R 1 . .
O O2 0.01845(8) 1.1416(2) 0.15941(8) 0.0607(5) Uani d . 1 . .
C C8 0.06408(9) 0.9758(2) 0.06998(9) 0.0355(4) Uani d . 1 . .
O O1 0.00415(8) 0.8407(2) 0.15781(7) 0.0572(4) Uani d . 1 . .
C C9 0.10590(10) 1.1195(3) 0.05077(9) 0.0424(5) Uani d . 1 . .
H H9 0.1096 1.2252 0.0763 0.051 Uiso calc R 1 . .
C C12 0.09496(10) 0.8128(3) -0.02711(9) 0.0418(5) Uani d . 1 A .
C C14 0.02558(9) 0.9872(3) 0.13409(9) 0.0397(4) Uani d . 1 . .
O O4 0.12095(11) 0.6430(3) -0.11917(9) 0.0845(6) Uani d . 1 A .
N N2 0.08814(12) 0.6506(3) -0.07003(10) 0.0655(6) Uani d . 1 . .
C C11 0.13792(10) 0.9514(3) -0.04684(9) 0.0433(5) Uani d . 1 . .
H H11 0.1629 0.9426 -0.0852 0.052 Uiso calc R 1 A .
N N3 0.18743(11) 1.2557(3) -0.02654(9) 0.0660(6) Uani d . 1 . .
C C10 0.14210(10) 1.1040(3) -0.00676(9) 0.0441(5) Uani d . 1 A .
O O5 0.21377(11) 1.2487(3) -0.07970(9) 0.0895(7) Uani d . 1 A .
N N1 0.03402(8) 0.4988(2) 0.21019(8) 0.0423(4) Uani d . 1 . .
H H1A 0.0216 0.3954 0.1899 0.051 Uiso calc R 1 . .
H H1B 0.0188 0.5959 0.1880 0.051 Uiso calc R 1 . .
H H1C 0.0168 0.5001 0.2503 0.051 Uiso calc R 1 . .
C C5 0.14494(11) 0.5352(3) 0.15756(10) 0.0464(5) Uani d . 1 . .
H H5 0.1232 0.5520 0.1177 0.056 Uiso calc R 1 . .
C C4 0.10811(10) 0.5068(2) 0.21395(9) 0.0378(4) Uani d . 1 . .
C C1 0.24824(11) 0.5139(3) 0.22000(10) 0.0443(5) Uani d . 1 . .
C C3 0.13975(11) 0.4821(3) 0.27266(10) 0.0504(5) Uani d . 1 . .
H H3 0.1146 0.4624 0.3104 0.061 Uiso calc R 1 . .
C C6 0.21460(11) 0.5381(3) 0.16134(10) 0.0501(5) Uani d . 1 . .
H H6 0.2396 0.5568 0.1234 0.060 Uiso calc R 1 . .
C C2 0.20983(11) 0.4868(3) 0.27537(10) 0.0527(6) Uani d . 1 . .
H H2 0.2313 0.4713 0.3154 0.063 Uiso calc R 1 . .
C C7 0.32394(11) 0.5136(3) 0.22312(13) 0.0601(6) Uani d . 1 . .
H H7A 0.3382 0.5282 0.2676 0.072 Uiso calc R 1 . .
H H7B 0.3413 0.6137 0.1974 0.072 Uiso calc R 1 . .
H H7C 0.3408 0.3986 0.2064 0.072 Uiso calc R 1 . .
O O6 0.1864(11) 1.4010(15) 0.0066(7) 0.079(3) Uani d P 0.59(5) A 1
O O3 0.0382(13) 0.549(3) -0.0614(5) 0.086(4) Uani d P 0.59(5) A 1
O O6' 0.2092(15) 1.351(5) 0.0179(11) 0.090(7) Uani d P 0.41(5) A 2
O O3' 0.0653(14) 0.5080(19) -0.0405(18) 0.086(6) Uani d P 0.41(5) A 2
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
C12 C13 C8 . . 119.15(17) ?
C12 C13 H13 . . 120.4 ?
C8 C13 H13 . . 120.4 ?
C9 C8 C13 . . 119.31(17) ?
C9 C8 C14 . . 120.25(16) ?
C13 C8 C14 . . 120.43(16) ?
C10 C9 C8 . . 119.36(18) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
C11 C12 C13 . . 122.91(18) ?
C11 C12 N2 . . 117.56(18) ?
C13 C12 N2 . . 119.53(18) ?
O2 C14 O1 . . 124.57(18) ?
O2 C14 C8 . . 117.84(17) ?
O1 C14 C8 . . 117.58(17) ?
O4 N2 O3 . . 121.6(4) ?
O4 N2 O3' . . 123.5(6) ?
O3 N2 O3' . . 34.5(6) ?
O4 N2 C12 . . 119.18(19) ?
O3 N2 C12 . . 117.2(6) ?
O3' N2 C12 . . 113.2(12) ?
C12 C11 C10 . . 116.52(18) ?
C12 C11 H11 . . 121.7 ?
C10 C11 H11 . . 121.7 ?
O5 N3 O6' . . 122.9(8) ?
O5 N3 O6 . . 122.1(6) ?
O6' N3 O6 . . 29.2(15) ?
O5 N3 C10 . . 118.59(19) ?
O6' N3 C10 . . 115.5(11) ?
O6 N3 C10 . . 117.9(7) ?
C11 C10 C9 . . 122.73(18) ?
C11 C10 N3 . . 118.01(18) ?
C9 C10 N3 . . 119.25(18) ?
C4 N1 H1A . . 109.5 ?
C4 N1 H1B . . 109.5 ?
H1A N1 H1B . . 109.5 ?
C4 N1 H1C . . 109.5 ?
H1A N1 H1C . . 109.5 ?
H1B N1 H1C . . 109.5 ?
C4 C5 C6 . . 118.84(19) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C3 C4 C5 . . 120.86(19) ?
C3 C4 N1 . . 119.86(16) ?
C5 C4 N1 . . 119.26(17) ?
C2 C1 C6 . . 117.8(2) ?
C2 C1 C7 . . 121.0(2) ?
C6 C1 C7 . . 121.17(19) ?
C4 C3 C2 . . 119.30(18) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C5 C6 C1 . . 121.78(18) ?
C5 C6 H6 . . 119.1 ?
C1 C6 H6 . . 119.1 ?
C1 C2 C3 . . 121.4(2) ?
C1 C2 H2 . . 119.3 ?
C3 C2 H2 . . 119.3 ?
C1 C7 H7A . . 109.5 ?
C1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
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
C13 C12 . 1.384(3) ?
C13 C8 . 1.389(3) ?
C13 H13 . 0.9300 ?
O2 C14 . 1.240(2) ?
C8 C9 . 1.386(3) ?
C8 C14 . 1.520(3) ?
O1 C14 . 1.241(2) ?
C9 C10 . 1.383(3) ?
C9 H9 . 0.9300 ?
C12 C11 . 1.376(3) ?
C12 N2 . 1.473(3) ?
O4 N2 . 1.199(2) ?
N2 O3 . 1.242(12) ?
N2 O3' . 1.279(19) ?
C11 C10 . 1.378(3) ?
C11 H11 . 0.9300 ?
N3 O5 . 1.208(2) ?
N3 O6' . 1.218(16) ?
N3 O6 . 1.252(12) ?
N3 C10 . 1.475(3) ?
N1 C4 . 1.469(3) ?
N1 H1A . 0.8900 ?
N1 H1B . 0.8900 ?
N1 H1C . 0.8900 ?
C5 C4 . 1.381(3) ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.9300 ?
C4 C3 . 1.367(3) ?
C1 C2 . 1.379(3) ?
C1 C6 . 1.384(3) ?
C1 C7 . 1.499(3) ?
C3 C2 . 1.388(3) ?
C3 H3 . 0.9300 ?
C6 H6 . 0.9300 ?
C2 H2 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
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 H1A O2 1_545 0.89 1.94 2.803(2) 162.6
N1 H1B O1 . 0.89 1.90 2.761(2) 162.8
N1 H1C O2 3_545 0.89 2.22 3.045(2) 153.1
N1 H1C O1 3_545 0.89 2.24 3.030(2) 147.0
C3 H3 O1 3_545 0.93 2.59 3.344(3) 138.2
C13 H13 O3 5_565 0.93 2.43 3.351(7) 172.8
