#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/96/2229628.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_2229628
loop_
_publ_author_name
'Zhang, Wan-Ju'
'Wang, Fang'
'Zhang, Gui-Ling'
'Xiao, Xin'
_publ_section_title
;
 A triclinic polymorph with Z = 3 of
 N,N'-bis(2-pyridyl)oxamide
;
_journal_coeditor_code           EZ2234
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o972
_journal_page_last               o973
_journal_paper_doi               10.1107/S1600536811010294
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H10 N4 O2'
_chemical_formula_moiety         'C12 H10 N4 O2'
_chemical_formula_sum            'C12 H10 N4 O2'
_chemical_formula_weight         242.24
_chemical_name_common
;
N,N'-bis(2-pyridyl)oxamide
;
_chemical_name_systematic
;
N,N'-bis(pyridin-2-yl)ethanediamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.555(9)
_cell_angle_beta                 101.344(8)
_cell_angle_gamma                112.980(8)
_cell_formula_units_Z            3
_cell_length_a                   8.459(2)
_cell_length_b                   10.705(3)
_cell_length_c                   11.058(3)
_cell_measurement_reflns_used    2575
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      1.95
_cell_volume                     870.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics
'XP (Siemens, 1994) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8909
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             378
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.343
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0444
_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/[σ²(Fo²)+(0.0745P)²+0.1649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                2575
_reflns_number_total             3018
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2234.cif
_cod_data_source_block           I
_cod_original_cell_volume        870.5(4)
_cod_original_sg_symbol_Hall     '-p 1'
_cod_database_code               2229628
_cod_database_fobs_code          2229628
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 C1 0.8362(2) 0.46853(19) 0.37248(18) 0.0520(4) Uani d . 1 . .
H H1 0.8499 0.5608 0.3908 0.062 Uiso calc R 1 . .
C C2 0.9305(2) 0.4331(2) 0.29625(17) 0.0530(5) Uani d . 1 . .
H H2 1.0085 0.5002 0.2655 0.064 Uiso calc R 1 . .
C C3 0.9066(3) 0.2958(2) 0.26675(17) 0.0557(5) Uani d . 1 . .
H H3 0.9672 0.2682 0.2144 0.067 Uiso calc R 1 . .
C C4 0.7921(3) 0.1992(2) 0.31520(17) 0.0525(4) Uani d . 1 . .
H H4 0.7732 0.1056 0.2957 0.063 Uiso calc R 1 . .
C C5 0.7062(2) 0.24577(17) 0.39383(15) 0.0413(4) Uani d . 1 . .
C C6 0.5610(2) 0.02730(17) 0.45799(16) 0.0433(4) Uani d . 1 . .
C C7 0.2643(3) 0.1234(2) 0.11856(19) 0.0686(6) Uani d . 1 . .
H H7 0.3133 0.2017 0.0881 0.082 Uiso calc R 1 . .
C C8 0.2515(4) -0.0019(2) 0.0534(2) 0.0805(7) Uani d . 1 . .
H H8 0.2911 -0.0087 -0.0191 0.097 Uiso calc R 1 . .
C C9 0.1791(4) -0.1164(2) 0.0977(2) 0.0880(8) Uani d . 1 . .
H H9 0.1681 -0.2033 0.0552 0.106 Uiso calc R 1 . .
C C10 0.1222(3) -0.1038(2) 0.20524(19) 0.0662(6) Uani d . 1 . .
H H10 0.0731 -0.1809 0.2371 0.079 Uiso calc R 1 . .
C C11 0.1405(2) 0.02693(16) 0.26431(14) 0.0386(4) Uani d . 1 . .
C C12 0.0128(2) -0.03698(15) 0.43944(14) 0.0364(3) Uani d . 1 . .
C C13 0.7504(3) 0.5115(2) 0.97931(17) 0.0646(6) Uani d . 1 . .
H H13 0.8479 0.5692 1.0504 0.078 Uiso calc R 1 . .
C C14 0.6308(3) 0.3874(2) 0.99039(17) 0.0631(5) Uani d . 1 . .
H H14 0.6460 0.3612 1.0664 0.076 Uiso calc R 1 . .
C C15 0.4884(3) 0.3032(2) 0.88626(18) 0.0660(6) Uani d . 1 . .
H H15 0.4042 0.2175 0.8901 0.079 Uiso calc R 1 . .
C C16 0.4690(3) 0.34467(18) 0.77573(16) 0.0521(5) Uani d . 1 . .
H H16 0.3719 0.2886 0.7040 0.063 Uiso calc R 1 . .
C C17 0.5974(2) 0.47196(15) 0.77397(13) 0.0347(3) Uani d . 1 . .
C C18 0.48440(19) 0.45519(14) 0.54712(13) 0.0312(3) Uani d . 1 . .
N N1 0.72567(19) 0.37762(14) 0.42180(14) 0.0472(4) Uani d . 1 . .
N N2 0.59256(19) 0.15935(14) 0.45411(14) 0.0457(4) Uani d . 1 . .
H H2A 0.5362 0.1959 0.4934 0.055 Uiso calc R 1 . .
N N3 0.2108(2) 0.14008(15) 0.22304(13) 0.0505(4) Uani d . 1 . .
N N4 0.08990(17) 0.05422(13) 0.37520(12) 0.0385(3) Uani d . 1 . .
H H4A 0.1109 0.1402 0.4060 0.046 Uiso calc R 1 . .
N N5 0.7374(2) 0.55612(16) 0.87343(13) 0.0531(4) Uani d . 1 . .
N N6 0.59098(16) 0.52565(12) 0.66636(11) 0.0351(3) Uani d . 1 . .
H H6 0.6628 0.6127 0.6784 0.042 Uiso calc R 1 . .
O O1 0.62022(18) -0.04585(13) 0.40434(13) 0.0584(4) Uani d . 1 . .
O O2 -0.03443(16) -0.16334(11) 0.41046(11) 0.0501(3) Uani d . 1 . .
O O3 0.37249(15) 0.33253(10) 0.51223(9) 0.0415(3) 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
N1 C1 C2 . . 123.58(17) ?
N1 C1 H1 . . 118.2 ?
C2 C1 H1 . . 118.2 ?
C1 C2 C3 . . 118.10(17) ?
C1 C2 H2 . . 121.0 ?
C3 C2 H2 . . 121.0 ?
C2 C3 C4 . . 119.68(17) ?
C2 C3 H3 . . 120.2 ?
C4 C3 H3 . . 120.2 ?
C3 C4 C5 . . 117.98(17) ?
C3 C4 H4 . . 121.0 ?
C5 C4 H4 . . 121.0 ?
N1 C5 C4 . . 123.16(15) ?
N1 C5 N2 . . 113.25(14) ?
C4 C5 N2 . . 123.58(15) ?
O1 C6 N2 . . 126.53(16) ?
O1 C6 C6 . 2_656 120.90(18) ?
N2 C6 C6 . 2_656 112.56(18) ?
N3 C7 C8 . . 123.90(18) ?
N3 C7 H7 . . 118.1 ?
C8 C7 H7 . . 118.1 ?
C9 C8 C7 . . 117.97(19) ?
C9 C8 H8 . . 121.0 ?
C7 C8 H8 . . 121.0 ?
C8 C9 C10 . . 120.0(2) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C9 C10 C11 . . 117.76(17) ?
C9 C10 H10 . . 121.1 ?
C11 C10 H10 . . 121.1 ?
N3 C11 C10 . . 123.32(15) ?
N3 C11 N4 . . 113.26(14) ?
C10 C11 N4 . . 123.41(14) ?
O2 C12 N4 . . 126.93(14) ?
O2 C12 C12 . 2_556 121.30(15) ?
N4 C12 C12 . 2_556 111.77(15) ?
N5 C13 C14 . . 124.56(18) ?
N5 C13 H13 . . 117.7 ?
C14 C13 H13 . . 117.7 ?
C15 C14 C13 . . 117.60(16) ?
C15 C14 H14 . . 121.2 ?
C13 C14 H14 . . 121.2 ?
C14 C15 C16 . . 119.96(17) ?
C14 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C15 C16 C17 . . 118.07(17) ?
C15 C16 H16 . . 121.0 ?
C17 C16 H16 . . 121.0 ?
N5 C17 C16 . . 123.44(14) ?
N5 C17 N6 . . 113.46(13) ?
C16 C17 N6 . . 123.09(14) ?
O3 C18 N6 . . 126.12(12) ?
O3 C18 C18 . 2_666 121.04(16) ?
N6 C18 C18 . 2_666 112.84(15) ?
C5 N1 C1 . . 117.47(15) ?
C6 N2 C5 . . 128.27(15) ?
C6 N2 H2A . . 115.9 ?
C5 N2 H2A . . 115.9 ?
C11 N3 C7 . . 117.05(15) ?
C12 N4 C11 . . 128.10(13) ?
C12 N4 H4A . . 115.9 ?
C11 N4 H4A . . 115.9 ?
C17 N5 C13 . . 116.37(15) ?
C18 N6 C17 . . 126.63(12) ?
C18 N6 H6 . . 116.7 ?
C17 N6 H6 . . 116.7 ?
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 . 1.373(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.375(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.378(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.386(2) ?
C4 H4 . 0.9300 ?
C5 N1 . 1.330(2) ?
C5 N2 . 1.410(2) ?
C6 O1 . 1.219(2) ?
C6 N2 . 1.342(2) ?
C6 C6 2_656 1.535(3) ?
C7 N3 . 1.331(2) ?
C7 C8 . 1.365(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.360(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.374(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.377(2) ?
C10 H10 . 0.9300 ?
C11 N3 . 1.326(2) ?
C11 N4 . 1.399(2) ?
C12 O2 . 1.2149(18) ?
C12 N4 . 1.3411(18) ?
C12 C12 2_556 1.537(3) ?
C13 N5 . 1.337(2) ?
C13 C14 . 1.363(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.361(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.370(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.378(2) ?
C16 H16 . 0.9300 ?
C17 N5 . 1.323(2) ?
C17 N6 . 1.4054(18) ?
C18 O3 . 1.2193(18) ?
C18 N6 . 1.3384(19) ?
C18 C18 2_666 1.523(3) ?
N2 H2A . 0.8600 ?
N4 H4A . 0.8600 ?
N6 H6 . 0.8600 ?
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
N2 H2A O3 ? 0.86 2.39 3.176(2) 153
N4 H4A O3 ? 0.86 2.27 2.898(2) 130
N6 H6 N3 2_666 0.86 2.39 3.188(2) 155
