#------------------------------------------------------------------------------
#$Date: 2017-07-25 12:26:49 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199119 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/21/2242143.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_2242143
loop_
_publ_author_name
'Cati, Dilovan S.'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 The crystal structures of three pyrazine-2,5-dicarboxamides:
 three-dimensional supramolecular structures
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              729
_journal_page_last               734
_journal_paper_doi               10.1107/S2056989017005898
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C18 H16 N6 O2'
_chemical_formula_moiety         'C18 H16 N6 O2'
_chemical_formula_sum            'C18 H16 N6 O2'
_chemical_formula_weight         348.37
_chemical_name_systematic
;
N²,N⁵-Bis(pyridin-2-ylmethyl)pyrazine-2,5-dicarboxamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 100.781(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0769(9)
_cell_length_b                   5.6076(7)
_cell_length_c                   18.3724(18)
_cell_measurement_reflns_used    3344
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.91
_cell_measurement_theta_min      2.26
_cell_volume                     817.44(16)
_computing_cell_refinement
;
CELL in IPDS-I (Stoe & Cie, 2004)
;
_computing_data_collection
;
EXPOSE in IPDS-I (Stoe & Cie, 2004)
;
_computing_data_reduction
;
INTEGRATE in IPDS-I (Stoe & Cie, 2004)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '1 circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 1'
_diffrn_measurement_method       'φ rotation'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.911
_diffrn_reflns_theta_min         2.257
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(MULABS; Spek, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.147
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2016 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.866
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0456P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0756
_reflns_number_gt                1024
_reflns_number_total             1574
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7672sup1.cif
_cod_data_source_block           I
_cod_database_code               2242143
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_occupancy
N N1 0.05799(15) 0.0574(2) 0.93513(7) 0.0261(3) Uani d 1
N N2 -0.05730(16) 0.4484(2) 0.85602(7) 0.0274(3) Uani d 1
H H2N 0.031(2) 0.366(3) 0.8485(10) 0.045(5) Uiso d 1
N N3 -0.26574(14) 0.7526(2) 0.68676(7) 0.0274(3) Uani d 1
O O1 -0.24558(13) 0.51737(18) 0.93146(6) 0.0336(3) Uani d 1
C C1 -0.06037(17) 0.1872(2) 0.95909(8) 0.0232(3) Uani d 1
C C2 0.11771(18) -0.1299(3) 0.97651(8) 0.0262(4) Uani d 1
H H2A 0.201781 -0.226769 0.961478 0.031 Uiso calc 1
C C3 -0.13034(17) 0.4004(3) 0.91401(8) 0.0253(4) Uani d 1
C C4 -0.10976(18) 0.6452(3) 0.80607(8) 0.0283(4) Uani d 1
H H4A -0.009417 0.709655 0.789038 0.034 Uiso calc 1
H H4B -0.155051 0.773295 0.833863 0.034 Uiso calc 1
C C5 -0.24122(16) 0.5825(3) 0.73894(8) 0.0223(3) Uani d 1
C C6 -0.33024(18) 0.3704(3) 0.73168(9) 0.0278(4) Uani d 1
H H6 -0.308875 0.252378 0.769361 0.033 Uiso calc 1
C C7 -0.45098(18) 0.3331(3) 0.66858(9) 0.0317(4) Uani d 1
H H7 -0.513660 0.188834 0.662344 0.038 Uiso calc 1
C C8 -0.47904(19) 0.5068(3) 0.61521(9) 0.0323(4) Uani d 1
H H8 -0.561978 0.485946 0.571644 0.039 Uiso calc 1
C C9 -0.38401(19) 0.7125(3) 0.62623(9) 0.0332(4) Uani d 1
H H9 -0.403298 0.832226 0.589013 0.040 Uiso calc 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
C2 N1 C1 . . 116.42(13)
C3 N2 C4 . . 122.52(13)
C3 N2 H2N . . 120.6(12)
C4 N2 H2N . . 116.8(12)
C5 N3 C9 . . 117.41(13)
N1 C1 C2 . 3_557 121.83(13)
N1 C1 C3 . . 117.97(13)
C2 C1 C3 3_557 . 120.21(13)
N1 C2 C1 . 3_557 121.75(13)
N1 C2 H2A . . 119.1
C1 C2 H2A 3_557 . 119.1
O1 C3 N2 . . 124.66(14)
O1 C3 C1 . . 120.38(14)
N2 C3 C1 . . 114.96(13)
N2 C4 C5 . . 114.69(12)
N2 C4 H4A . . 108.6
C5 C4 H4A . . 108.6
N2 C4 H4B . . 108.6
C5 C4 H4B . . 108.6
H4A C4 H4B . . 107.6
N3 C5 C6 . . 122.56(13)
N3 C5 C4 . . 113.93(12)
C6 C5 C4 . . 123.51(13)
C5 C6 C7 . . 118.86(14)
C5 C6 H6 . . 120.6
C7 C6 H6 . . 120.6
C8 C7 C6 . . 119.23(14)
C8 C7 H7 . . 120.4
C6 C7 H7 . . 120.4
C7 C8 C9 . . 118.44(14)
C7 C8 H8 . . 120.8
C9 C8 H8 . . 120.8
N3 C9 C8 . . 123.49(15)
N3 C9 H9 . . 118.3
C8 C9 H9 . . 118.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C2 . 1.3330(19)
N1 C1 . 1.3397(18)
N2 C3 . 1.338(2)
N2 C4 . 1.4475(19)
N2 H2N . 0.879(19)
N3 C5 . 1.3405(18)
N3 C9 . 1.3424(19)
O1 C3 . 1.2290(17)
C1 C2 3_557 1.387(2)
C1 C3 . 1.503(2)
C2 H2A . 0.9500
C4 C5 . 1.5107(19)
C4 H4A . 0.9900
C4 H4B . 0.9900
C5 C6 . 1.383(2)
C6 C7 . 1.384(2)
C6 H6 . 0.9500
C7 C8 . 1.370(2)
C7 H7 . 0.9500
C8 C9 . 1.380(2)
C8 H8 . 0.9500
C9 H9 . 0.9500
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 H2N N3 2_546 0.88(2) 2.209(17) 3.0657(18) 164(2)
C7 H7 O1 2_446 0.95 2.53 3.292(2) 137
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_4
_geom_torsion
C2 N1 C1 C2 . 3_557 0.0(2)
C2 N1 C1 C3 . . 179.79(12)
C1 N1 C2 C1 . 3_557 0.0(2)
C4 N2 C3 O1 . . -1.0(2)
C4 N2 C3 C1 . . 179.29(12)
N1 C1 C3 O1 . . 175.99(13)
C2 C1 C3 O1 3_557 . -4.2(2)
N1 C1 C3 N2 . . -4.33(18)
C2 C1 C3 N2 3_557 . 175.43(12)
C3 N2 C4 C5 . . -92.36(17)
C9 N3 C5 C6 . . 1.1(2)
C9 N3 C5 C4 . . -178.26(13)
N2 C4 C5 N3 . . -168.30(13)
N2 C4 C5 C6 . . 12.3(2)
N3 C5 C6 C7 . . -0.9(2)
C4 C5 C6 C7 . . 178.46(14)
C5 C6 C7 C8 . . 0.0(2)
C6 C7 C8 C9 . . 0.6(2)
C5 N3 C9 C8 . . -0.5(2)
C7 C8 C9 N3 . . -0.3(2)

_cod_database_fobs_code 2242143
