#------------------------------------------------------------------------------
#$Date: 2023-03-08 10:12:45 +0200 (Wed, 08 Mar 2023) $
#$Revision: 281729 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106872.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106872
loop_
_publ_author_name
'Habarurema, Gratien'
'Gerber, Thomas I. A.'
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of 1,2-bis(2-pyrazinecarboxamido)-benzene,
 C16H12N6O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              347
_journal_page_last               349
_journal_paper_doi               10.1515/ncrs-2014-8191
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C16 H12 N6 O2'
_chemical_formula_sum            'C16 H12 N6 O2'
_chemical_formula_weight         320.32
_chemical_name_common
;
bis(pyrazinecarboxylicacid)-ortho-phenylenediamide
;
_chemical_name_systematic
;
1,2-bis(2-pyrazinecarboxamido)-benzene
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 109.955(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2912(9)
_cell_length_b                   9.4979(6)
_cell_length_c                   14.5778(10)
_cell_measurement_reflns_used    3627
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      2.61
_cell_volume                     1469.50(18)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEPIII (Farrugia, 2012), Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-97, PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13430
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9052
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS (Bruker, 2008)                                          
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.285
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.231
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0421
_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)+(0.0484P)²+0.2894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                2495
_reflns_number_total             3650
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2014-8191_suppl.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_Hall     ' 	-P 2ybc'
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               8106872
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.10512(15) 0.33905(12) -0.08162(8) 0.0617(4) Uani 1 1 d . . .
O2 O 0.42821(11) 0.60921(11) 0.11715(7) 0.0418(3) Uani 1 1 d . . .
N1 N 0.15660(12) 0.52502(12) 0.02337(9) 0.0313(3) Uani 1 1 d . . .
H71 H 0.1851(15) 0.5419(17) 0.0855(13) 0.040(5) Uiso 1 1 d . . .
N2 N 0.27688(11) 0.77110(12) 0.10795(8) 0.0290(3) Uani 1 1 d . . .
H72 H 0.2559(16) 0.8378(17) 0.1403(12) 0.040(5) Uiso 1 1 d . . .
N21 N 0.16764(14) 0.06142(14) 0.15014(10) 0.0424(3) Uani 1 1 d . . .
N22 N 0.21428(12) 0.35085(13) 0.17620(9) 0.0347(3) Uani 1 1 d . . .
N31 N 0.56198(14) 0.63286(17) 0.42008(10) 0.0500(4) Uani 1 1 d . . .
N32 N 0.39090(12) 0.82685(12) 0.30189(8) 0.0309(3) Uani 1 1 d . . .
C1 C 0.13821(15) 0.38758(15) 0.00044(10) 0.0331(3) Uani 1 1 d . . .
C2 C 0.37976(13) 0.69374(14) 0.15649(10) 0.0288(3) Uani 1 1 d . . .
C11 C 0.15588(13) 0.63896(14) -0.03825(10) 0.0281(3) Uani 1 1 d . . .
C12 C 0.09559(14) 0.63378(16) -0.13910(10) 0.0322(3) Uani 1 1 d . . .
H12 H 0.0538 0.5502 -0.1690 0.039 Uiso 1 1 calc R . .
C13 C 0.09672(15) 0.75062(17) -0.19562(11) 0.0365(4) Uani 1 1 d . . .
H13 H 0.0553 0.7469 -0.2643 0.044 Uiso 1 1 calc R . .
C14 C 0.15738(16) 0.87213(16) -0.15318(11) 0.0387(4) Uani 1 1 d . . .
H14 H 0.1575 0.9518 -0.1925 0.046 Uiso 1 1 calc R . .
C15 C 0.21814(14) 0.87837(15) -0.05327(10) 0.0334(3) Uani 1 1 d . . .
H15 H 0.2606 0.9621 -0.0242 0.040 Uiso 1 1 calc R . .
C16 C 0.21721(13) 0.76289(14) 0.00464(10) 0.0274(3) Uani 1 1 d . . .
C21 C 0.16380(13) 0.29367(15) 0.08769(10) 0.0298(3) Uani 1 1 d . . .
C22 C 0.13888(16) 0.15097(15) 0.07512(12) 0.0372(4) Uani 1 1 d . . .
H22 H 0.1000 0.1155 0.0109 0.045 Uiso 1 1 calc R . .
C23 C 0.21786(16) 0.11927(16) 0.23801(12) 0.0415(4) Uani 1 1 d . . .
H23 H 0.2396 0.0600 0.2938 0.050 Uiso 1 1 calc R . .
C24 C 0.23957(16) 0.26206(16) 0.25125(12) 0.0400(4) Uani 1 1 d . . .
H24 H 0.2735 0.2981 0.3158 0.048 Uiso 1 1 calc R . .
C31 C 0.42995(13) 0.71496(14) 0.26476(10) 0.0276(3) Uani 1 1 d . . .
C32 C 0.51427(15) 0.61909(17) 0.32297(11) 0.0384(4) Uani 1 1 d . . .
H32 H 0.5392 0.5409 0.2932 0.046 Uiso 1 1 calc R . .
C33 C 0.52216(16) 0.74420(19) 0.45612(11) 0.0452(4) Uani 1 1 d . . .
H33 H 0.5529 0.7583 0.5248 0.054 Uiso 1 1 calc R . .
C34 C 0.43811(15) 0.84042(16) 0.39838(10) 0.0356(3) Uani 1 1 d . . .
H34 H 0.4132 0.9185 0.4283 0.043 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C11 128.44(12) . .
C1 N1 H71 114.2(11) . .
C11 N1 H71 116.4(11) . .
C2 N2 C16 122.31(12) . .
C2 N2 H72 117.1(11) . .
C16 N2 H72 119.7(11) . .
C23 N21 C22 115.49(14) . .
C24 N22 C21 115.92(13) . .
C33 N31 C32 115.38(14) . .
C34 N32 C31 115.97(13) . .
O1 C1 N1 125.57(14) . .
O1 C1 C21 120.99(13) . .
N1 C1 C21 113.43(12) . .
O2 C2 N2 123.69(13) . .
O2 C2 C31 121.01(13) . .
N2 C2 C31 115.27(12) . .
C12 C11 C16 119.31(13) . .
C12 C11 N1 122.77(13) . .
C16 C11 N1 117.91(12) . .
C13 C12 C11 119.92(14) . .
C13 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
C14 C13 C12 120.58(14) . .
C14 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
C13 C14 C15 120.07(14) . .
C13 C14 H14 120.0 . .
C15 C14 H14 120.0 . .
C14 C15 C16 120.21(14) . .
C14 C15 H15 119.9 . .
C16 C15 H15 119.9 . .
C15 C16 C11 119.91(12) . .
C15 C16 N2 120.03(12) . .
C11 C16 N2 120.05(12) . .
N22 C21 C22 121.80(13) . .
N22 C21 C1 118.24(12) . .
C22 C21 C1 119.93(13) . .
N21 C22 C21 122.27(14) . .
N21 C22 H22 118.9 . .
C21 C22 H22 118.9 . .
N21 C23 C24 122.53(15) . .
N21 C23 H23 118.7 . .
C24 C23 H23 118.7 . .
N22 C24 C23 121.93(15) . .
N22 C24 H24 119.0 . .
C23 C24 H24 119.0 . .
N32 C31 C32 122.03(13) . .
N32 C31 C2 118.45(12) . .
C32 C31 C2 119.52(13) . .
N31 C32 C31 122.01(15) . .
N31 C32 H32 119.0 . .
C31 C32 H32 119.0 . .
N31 C33 C34 122.89(15) . .
N31 C33 H33 118.6 . .
C34 C33 H33 118.6 . .
N32 C34 C33 121.72(15) . .
N32 C34 H34 119.1 . .
C33 C34 H34 119.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2158(17) .
O2 C2 1.2194(16) .
N1 C1 1.3459(18) .
N1 C11 1.4047(17) .
N1 H71 0.867(17) .
N2 C2 1.3524(18) .
N2 C16 1.4267(17) .
N2 H72 0.870(17) .
N21 C23 1.330(2) .
N21 C22 1.335(2) .
N22 C24 1.3328(19) .
N22 C21 1.3351(18) .
N31 C33 1.326(2) .
N31 C32 1.338(2) .
N32 C34 1.3294(18) .
N32 C31 1.3340(18) .
C1 C21 1.499(2) .
C2 C31 1.4974(19) .
C11 C12 1.3943(19) .
C11 C16 1.4001(19) .
C12 C13 1.385(2) .
C12 H12 0.9500 .
C13 C14 1.376(2) .
C13 H13 0.9500 .
C14 C15 1.383(2) .
C14 H14 0.9500 .
C15 C16 1.3862(19) .
C15 H15 0.9500 .
C21 C22 1.384(2) .
C22 H22 0.9500 .
C23 C24 1.380(2) .
C23 H23 0.9500 .
C24 H24 0.9500 .
C31 C32 1.380(2) .
C32 H32 0.9500 .
C33 C34 1.378(2) .
C33 H33 0.9500 .
C34 H34 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H71 N22 0.867(17) 2.203(16) 2.6710(17) 113.6(13) .
N2 H72 N21 0.870(17) 2.371(17) 3.1656(18) 152.0(14) 1_565
C13 H13 O1 0.95 2.51 3.3753(19) 151.0 2_554
C15 H15 N31 0.95 2.62 3.534(2) 161.0 2_655
C33 H33 O2 0.95 2.58 3.205(2) 123.3 4_576
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C11 N1 C1 O1 -7.6(3) . . . .
C11 N1 C1 C21 171.83(13) . . . .
C16 N2 C2 O2 -1.6(2) . . . .
C16 N2 C2 C31 -179.77(12) . . . .
C1 N1 C11 C12 21.9(2) . . . .
C1 N1 C11 C16 -158.99(15) . . . .
C16 C11 C12 C13 -0.1(2) . . . .
N1 C11 C12 C13 178.99(14) . . . .
C11 C12 C13 C14 0.3(2) . . . .
C12 C13 C14 C15 0.1(2) . . . .
C13 C14 C15 C16 -0.6(2) . . . .
C14 C15 C16 C11 0.8(2) . . . .
C14 C15 C16 N2 -178.19(14) . . . .
C12 C11 C16 C15 -0.4(2) . . . .
N1 C11 C16 C15 -179.54(13) . . . .
C12 C11 C16 N2 178.55(13) . . . .
N1 C11 C16 N2 -0.58(19) . . . .
C2 N2 C16 C15 -113.98(15) . . . .
C2 N2 C16 C11 67.05(18) . . . .
C24 N22 C21 C22 0.3(2) . . . .
C24 N22 C21 C1 -177.58(14) . . . .
O1 C1 C21 N22 172.05(16) . . . .
N1 C1 C21 N22 -7.4(2) . . . .
O1 C1 C21 C22 -5.9(2) . . . .
N1 C1 C21 C22 174.63(14) . . . .
C23 N21 C22 C21 2.2(2) . . . .
N22 C21 C22 N21 -2.4(2) . . . .
C1 C21 C22 N21 175.49(14) . . . .
C22 N21 C23 C24 -0.3(2) . . . .
C21 N22 C24 C23 1.6(2) . . . .
N21 C23 C24 N22 -1.7(3) . . . .
C34 N32 C31 C32 0.0(2) . . . .
C34 N32 C31 C2 179.82(12) . . . .
O2 C2 C31 N32 166.69(13) . . . .
N2 C2 C31 N32 -15.11(19) . . . .
O2 C2 C31 C32 -13.5(2) . . . .
N2 C2 C31 C32 164.73(13) . . . .
C33 N31 C32 C31 0.3(2) . . . .
N32 C31 C32 N31 -0.1(2) . . . .
C2 C31 C32 N31 -179.94(14) . . . .
C32 N31 C33 C34 -0.4(3) . . . .
C31 N32 C34 C33 -0.1(2) . . . .
N31 C33 C34 N32 0.3(3) . . . .
