#------------------------------------------------------------------------------
#$Date: 2017-07-25 12:26:49 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199119 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/21/2242144.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_2242144
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          'C20 H20 N6 O2'
_chemical_formula_moiety         'C20 H20 N6 O2'
_chemical_formula_sum            'C20 H20 N6 O2'
_chemical_formula_weight         376.42
_chemical_name_systematic
3,6-Dimethyl-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 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.834(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7271(5)
_cell_length_b                   5.2950(4)
_cell_length_c                   20.1403(13)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.00
_cell_measurement_theta_min      20.40
_cell_volume                     917.01(11)
_computing_cell_refinement
;
STADI4 (Stoe & Cie, 1997)
;
_computing_data_collection
;
STADI4 (Stoe & Cie, 1997)
;
_computing_data_reduction
;
X-RED (Stoe & Cie, 1997)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015), PLATON (Spek, 2009)
and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Stoe--Siemens AED2 four-circle'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            2576
_diffrn_reflns_theta_full        59.574
_diffrn_reflns_theta_max         59.574
_diffrn_reflns_theta_min         4.456
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(MULABS; Spek, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       rod
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.124
_refine_ls_extinction_coef       0.0124(10)
_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   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0354
_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)+(0.0453P)²+0.2943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                1226
_reflns_number_total             1345
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7672sup1.cif
_cod_data_source_block           II
_cod_database_code               2242144
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O O1 1.12510(14) 0.4700(3) 0.90448(6) 0.0615(4) Uani d 1
N N1 0.88491(14) 0.9651(3) 0.94504(6) 0.0422(4) Uani d 1
N N2 0.89518(17) 0.6199(3) 0.85116(7) 0.0466(4) Uani d 1
H H2N 0.818(2) 0.714(4) 0.8529(10) 0.061(6) Uiso d 1
N N3 0.94177(16) 0.3148(3) 0.69204(7) 0.0503(4) Uani d 1
C C1 1.01225(18) 0.8206(3) 0.95440(8) 0.0399(4) Uani d 1
C C2 0.86917(18) 1.1468(3) 0.98964(8) 0.0408(4) Uani d 1
C C3 1.01729(18) 0.6201(3) 0.90156(8) 0.0432(4) Uani d 1
C C4 0.87726(19) 0.4317(3) 0.79852(8) 0.0453(4) Uani d 1
H H4A 0.767587 0.416493 0.779865 0.054 Uiso calc 1
H H4B 0.911490 0.270168 0.818461 0.054 Uiso calc 1
C C5 0.96522(17) 0.4847(3) 0.74167(8) 0.0381(4) Uani d 1
C C6 1.06331(19) 0.6880(3) 0.74049(9) 0.0466(5) Uani d 1
H H6 1.074867 0.807192 0.774909 0.056 Uiso calc 1
C C7 1.14401(19) 0.7128(4) 0.68778(9) 0.0514(5) Uani d 1
H H7 1.210827 0.848639 0.686234 0.062 Uiso calc 1
C C8 1.1248(2) 0.5356(4) 0.63781(9) 0.0529(5) Uani d 1
H H8 1.179711 0.545797 0.602164 0.064 Uiso calc 1
C C9 1.0223(2) 0.3422(4) 0.64172(9) 0.0577(5) Uani d 1
H H9 1.008001 0.223016 0.607303 0.069 Uiso calc 1
C C10 0.7223(2) 1.3002(4) 0.97432(9) 0.0539(5) Uani d 1
H H10A 0.672121 1.267830 0.928884 0.081 Uiso calc 1
H H10B 0.747288 1.476475 0.979389 0.081 Uiso calc 1
H H10C 0.653830 1.254180 1.004892 0.081 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 N1 C2 . . 119.67(13)
C3 N2 C4 . . 121.93(15)
C3 N2 H2N . . 120.4(14)
C4 N2 H2N . . 116.7(14)
C5 N3 C9 . . 117.48(15)
N1 C1 C2 . 3_777 121.60(14)
N1 C1 C3 . . 115.29(14)
C2 C1 C3 3_777 . 123.11(14)
N1 C2 C1 . 3_777 118.73(14)
N1 C2 C10 . . 115.57(14)
C1 C2 C10 3_777 . 125.69(15)
O1 C3 N2 . . 122.72(16)
O1 C3 C1 . . 122.48(15)
N2 C3 C1 . . 114.80(14)
N2 C4 C5 . . 115.02(14)
N2 C4 H4A . . 108.5
C5 C4 H4A . . 108.5
N2 C4 H4B . . 108.5
C5 C4 H4B . . 108.5
H4A C4 H4B . . 107.5
N3 C5 C6 . . 122.01(15)
N3 C5 C4 . . 114.19(14)
C6 C5 C4 . . 123.79(14)
C7 C6 C5 . . 119.25(16)
C7 C6 H6 . . 120.4
C5 C6 H6 . . 120.4
C8 C7 C6 . . 119.26(16)
C8 C7 H7 . . 120.4
C6 C7 H7 . . 120.4
C7 C8 C9 . . 118.03(16)
C7 C8 H8 . . 121.0
C9 C8 H8 . . 121.0
N3 C9 C8 . . 123.91(17)
N3 C9 H9 . . 118.0
C8 C9 H9 . . 118.0
C2 C10 H10A . . 109.5
C2 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C2 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C3 . 1.2255(19)
N1 C1 . 1.336(2)
N1 C2 . 1.339(2)
N2 C3 . 1.340(2)
N2 C4 . 1.444(2)
N2 H2N . 0.85(2)
N3 C5 . 1.335(2)
N3 C9 . 1.336(2)
C1 C2 3_777 1.404(2)
C1 C3 . 1.509(2)
C2 C10 . 1.504(2)
C4 C5 . 1.510(2)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 C6 . 1.378(2)
C6 C7 . 1.377(2)
C6 H6 . 0.9300
C7 C8 . 1.365(3)
C7 H7 . 0.9300
C8 C9 . 1.371(3)
C8 H8 . 0.9300
C9 H9 . 0.9300
C10 H10A . 0.9600
C10 H10B . 0.9600
C10 H10C . 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
N2 H2N N3 2_656 0.85(2) 2.35(2) 3.097(2) 147.4(18)
C7 H7 O1 2_756 0.93 2.59 3.263(2) 130
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_777 0.3(3)
C2 N1 C1 C3 . . 179.38(14)
C1 N1 C2 C1 . 3_777 -0.3(2)
C1 N1 C2 C10 . . 179.58(15)
C4 N2 C3 O1 . . 3.9(3)
C4 N2 C3 C1 . . -176.38(14)
N1 C1 C3 O1 . . -178.22(15)
C2 C1 C3 O1 3_777 . 0.9(3)
N1 C1 C3 N2 . . 2.0(2)
C2 C1 C3 N2 3_777 . -178.88(15)
C3 N2 C4 C5 . . -83.2(2)
C9 N3 C5 C6 . . 2.7(2)
C9 N3 C5 C4 . . -176.51(16)
N2 C4 C5 N3 . . -177.14(14)
N2 C4 C5 C6 . . 3.6(2)
N3 C5 C6 C7 . . -2.3(3)
C4 C5 C6 C7 . . 176.86(15)
C5 C6 C7 C8 . . 0.1(3)
C6 C7 C8 C9 . . 1.4(3)
C5 N3 C9 C8 . . -1.1(3)
C7 C8 C9 N3 . . -1.0(3)

_cod_database_fobs_code 2242144
