#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/88/2008850.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_2008850
loop_
_publ_author_name
'Paixão, J. A.'
'Matos Beja, A.'
'Ramos Silva, M.'
'Alte da Veiga, L.'
_publ_section_title
;
 Bis(N,N'-diphenylguanidinium) oxalate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1290
_journal_page_last               1292
_journal_paper_doi               10.1107/S010827019900493X
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         '2C13 H14 N3 1+ , C2 O4  2-'
_chemical_formula_sum            'C28 H28 N6 O4'
_chemical_formula_weight         512.56
_chemical_name_systematic
;
 bis(N,N'-diphenylguanidinium) oxalate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.59(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.784(9)
_cell_length_b                   11.101(9)
_cell_length_c                   12.384(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.38
_cell_measurement_theta_min      10.20
_cell_volume                     2607(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'SDP-Plus (Frenz, 1985)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.895
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'profile data from ω-2θ scans'
_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  0.017
_diffrn_reflns_av_sigmaI/netI    0.033
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2918
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        5.8
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.136
_refine_ls_extinction_coef       0.0038(4)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.087
_refine_ls_R_factor_gt           0.035
_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)+(0.0405P)²+0.9201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.095
_reflns_number_gt                1688
_reflns_number_total             2682
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1285.cif
_cod_data_source_block           dpgox
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2008850
_cod_database_fobs_code          2008850
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
C1 0.32118(8) 0.89752(14) -0.15994(12) 0.0408(4) Uani d . 1 . . C
N1 0.33476(7) 0.91994(12) -0.05007(10) 0.0437(3) Uani d . 1 . . N
H1 0.3169(9) 0.9855(17) -0.0299(14) 0.052 Uiso d . 1 . . H
N2 0.27517(8) 0.96477(14) -0.23252(12) 0.0511(4) Uani d . 1 . . N
H2A 0.2532(10) 1.0244(18) -0.2067(15) 0.061 Uiso d . 1 . . H
H2B 0.2715(9) 0.9566(17) -0.3054(16) 0.061 Uiso d . 1 . . H
N3 0.35316(7) 0.80790(14) -0.19904(11) 0.0503(4) Uani d . 1 . . N
H3 0.3297(9) 0.7792(17) -0.2658(16) 0.060 Uiso d . 1 . . H
C2 0.35665(8) 0.83524(14) 0.03959(12) 0.0403(4) Uani d . 1 . . C
C3 0.33850(9) 0.71490(16) 0.02746(16) 0.0510(4) Uani d . 1 . . C
H3A 0.3127(9) 0.6873(17) -0.0479(15) 0.061 Uiso d . 1 . . H
C4 0.35813(12) 0.63952(19) 0.1205(2) 0.0670(6) Uani d . 1 . . C
H4 0.3435(11) 0.559(2) 0.1089(17) 0.080 Uiso d . 1 . . H
C5 0.39404(13) 0.6838(2) 0.2235(2) 0.0782(7) Uani d . 1 . . C
H5 0.4083(12) 0.632(2) 0.289(2) 0.094 Uiso d . 1 . . H
C6 0.41137(13) 0.8034(2) 0.23543(17) 0.0764(6) Uani d . 1 . . C
H6 0.4400(12) 0.835(2) 0.3100(19) 0.092 Uiso d . 1 . . H
C7 0.39314(10) 0.87918(18) 0.14381(14) 0.0566(5) Uani d . 1 . . C
H7 0.4047(10) 0.9618(19) 0.1511(16) 0.068 Uiso d . 1 . . H
C8 0.42190(8) 0.76363(15) -0.14693(12) 0.0437(4) Uani d . 1 . . C
C9 0.47615(10) 0.83986(18) -0.09428(15) 0.0552(5) Uani d . 1 . . C
H9 0.4665(10) 0.9230(18) -0.0915(16) 0.066 Uiso d . 1 . . H
C10 0.54283(10) 0.7938(2) -0.04791(17) 0.0660(6) Uani d . 1 . . C
H10 0.5792(11) 0.844(2) -0.0113(17) 0.079 Uiso d . 1 . . H
C11 0.55564(11) 0.6733(2) -0.05405(18) 0.0706(6) Uani d . 1 . . C
H11 0.6020(12) 0.641(2) -0.0211(17) 0.085 Uiso d . 1 . . H
C12 0.50197(12) 0.5984(2) -0.1078(2) 0.0753(6) Uani d . 1 . . C
H12 0.5105(11) 0.515(2) -0.1152(18) 0.090 Uiso d . 1 . . H
C13 0.43502(11) 0.64318(18) -0.15451(17) 0.0627(5) Uani d . 1 . . C
H13 0.3960(11) 0.5907(19) -0.1916(16) 0.075 Uiso d . 1 . . H
O1 0.28204(7) 1.10732(10) 0.04705(9) 0.0554(3) Uani d . 1 . . O
O2 0.22742(7) 1.16781(10) -0.12543(9) 0.0536(3) Uani d . 1 . . O
C14 0.25252(8) 1.18545(13) -0.02284(11) 0.0366(3) Uani d . 1 . . C
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_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N1 . 119.38(15) yes
N2 C1 N3 . 118.72(14) yes
N1 C1 N3 . 121.90(14) yes
C1 N1 C2 . 126.88(14) yes
C1 N1 H1 . 117.8(11) ?
C2 N1 H1 . 112.5(11) ?
C1 N2 H2A . 119.1(12) ?
C1 N2 H2B . 118.4(12) ?
H2A N2 H2B . 121.9(17) ?
C1 N3 C8 . 125.69(13) yes
C1 N3 H3 . 115.4(12) ?
C8 N3 H3 . 118.8(12) ?
C7 C2 C3 . 119.72(16) ?
C7 C2 N1 . 117.28(15) ?
C3 C2 N1 . 122.83(15) ?
C2 C3 C4 . 119.41(19) ?
C2 C3 H3A . 117.2(11) ?
C4 C3 H3A . 123.4(11) ?
C5 C4 C3 . 120.5(2) ?
C5 C4 H4 . 122.9(13) ?
C3 C4 H4 . 116.4(13) ?
C4 C5 C6 . 119.9(2) ?
C4 C5 H5 . 121.2(14) ?
C6 C5 H5 . 118.9(14) ?
C5 C6 C7 . 120.4(2) ?
C5 C6 H6 . 119.7(14) ?
C7 C6 H6 . 119.8(14) ?
C6 C7 C2 . 120.1(2) ?
C6 C7 H7 . 121.1(12) ?
C2 C7 H7 . 118.9(12) ?
C13 C8 C9 . 119.68(17) ?
C13 C8 N3 . 118.90(16) ?
C9 C8 N3 . 121.33(16) ?
C8 C9 C10 . 119.57(19) ?
C8 C9 H9 . 118.6(12) ?
C10 C9 H9 . 121.8(12) ?
C11 C10 C9 . 120.7(2) ?
C11 C10 H10 . 119.3(14) ?
C9 C10 H10 . 120.0(14) ?
C12 C11 C10 . 119.5(2) ?
C12 C11 H11 . 119.5(13) ?
C10 C11 H11 . 121.0(13) ?
C11 C12 C13 . 120.4(2) ?
C11 C12 H12 . 120.4(13) ?
C13 C12 H12 . 119.1(13) ?
C8 C13 C12 . 120.1(2) ?
C8 C13 H13 . 118.5(12) ?
C12 C13 H13 . 121.4(12) ?
O2 C14 O1 . 124.92(14) ?
O2 C14 C14 7_575 118.02(15) ?
O1 C14 C14 7_575 117.06(15) ?
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 . 1.314(2) yes
C1 N1 . 1.3329(19) yes
C1 N3 . 1.341(2) yes
N1 C2 . 1.425(2) yes
N1 H1 . 0.876(19) ?
N2 H2A . 0.90(2) ?
N2 H2B . 0.889(19) ?
N3 C8 . 1.416(2) yes
N3 H3 . 0.884(19) ?
C2 C7 . 1.376(2) ?
C2 C3 . 1.380(3) ?
C3 C4 . 1.387(3) ?
C3 H3A . 0.977(18) ?
C4 C5 . 1.362(3) ?
C4 H4 . 0.93(2) ?
C5 C6 . 1.369(4) ?
C5 H5 . 0.97(2) ?
C6 C7 . 1.375(3) ?
C6 H6 . 1.00(2) ?
C7 H7 . 0.94(2) ?
C8 C13 . 1.370(3) ?
C8 C9 . 1.376(2) ?
C9 C10 . 1.378(3) ?
C9 H9 . 0.945(19) ?
C10 C11 . 1.367(3) ?
C10 H10 . 0.92(2) ?
C11 C12 . 1.363(3) ?
C11 H11 . 0.96(2) ?
C12 C13 . 1.378(3) ?
C12 H12 . 0.95(2) ?
C13 H13 . 0.97(2) ?
O1 C14 . 1.2465(18) ?
O2 C14 . 1.2404(17) ?
C14 C14 7_575 1.554(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
N1 H1 O1 . 0.876(19) 1.894(19) 2.753(2) 166.2(16)
N2 H2A O2 . 0.90(2) 2.03(2) 2.906(2) 166.3(17)
N2 H2B O1 6_575 0.889(19) 2.03(2) 2.885(2) 162.2(17)
N3 H3 O2 4_544 0.884(19) 1.937(19) 2.776(2) 158.0(17)
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
_geom_torsion_publ_flag
N2 C1 N1 C2 151.17(17) yes
N3 C1 N1 C2 -28.8(3) ?
N2 C1 N3 C8 149.85(17) yes
N1 C1 N3 C8 -30.2(3) ?
C1 N1 C2 C7 155.63(17) ?
C1 N1 C2 C3 -29.0(2) yes
C7 C2 C3 C4 -0.8(3) ?
N1 C2 C3 C4 -176.00(16) ?
C2 C3 C4 C5 1.0(3) ?
C3 C4 C5 C6 -0.4(3) ?
C4 C5 C6 C7 -0.4(4) ?
C5 C6 C7 C2 0.7(3) ?
C3 C2 C7 C6 0.0(3) ?
N1 C2 C7 C6 175.43(18) ?
C1 N3 C8 C13 145.29(18) ?
C1 N3 C8 C9 -38.1(3) yes
C13 C8 C9 C10 -1.2(3) ?
N3 C8 C9 C10 -177.79(17) ?
C8 C9 C10 C11 0.2(3) ?
C9 C10 C11 C12 0.8(3) ?
C10 C11 C12 C13 -0.8(4) ?
C9 C8 C13 C12 1.2(3) ?
N3 C8 C13 C12 177.87(18) ?
C11 C12 C13 C8 -0.2(3) ?
