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#$Date: 2018-12-04 13:11:15 +0200 (Tue, 04 Dec 2018) $
#$Revision: 212337 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/13/2021397.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_2021397
loop_
_publ_author_name
'Dutkiewicz, Grzegorz'
'Dutkiewicz, Edward'
'Kubicki, Maciej'
_publ_contact_author
;
Maciej Kubicki
Faculty of Chemistry
Adam Mickiewicz University
Grunwaldzka 6
60-780 Poznań
Poland 
;
_publ_section_title
;
 Cocrystals of pyrazine and benzene polycarboxylic acids
;
_publ_section_keywords
;
cocrystals; pyrazine; benzene carboxylic acids; hydrogen bonds; Hirshfeld
surface, crystal structure
;
_journal_coeditor_code           YP3167
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1420
_journal_page_last               1426
_journal_paper_doi               10.1107/S2053229618013669
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C4 H4 N2, C8 H6 O4'
_chemical_formula_moiety         'C4 H4 N2, C8 H6 O4'
_chemical_formula_sum            'C12 H10 N2 O4'
_chemical_formula_weight         246.22
_chemical_name_common
;
Pyrazine--phthalic acid (1/1)
;
_chemical_name_systematic
;
Pyrazine--benzene-1,2-dicarboxylic acid (1/1)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.425(7)
_cell_angle_beta                 96.907(6)
_cell_angle_gamma                114.347(9)
_cell_formula_units_Z            2
_cell_length_a                   6.6714(5)
_cell_length_b                   7.3296(8)
_cell_length_c                   12.9870(9)
_cell_measurement_reflns_used    1538
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      27.9370
_cell_measurement_theta_min      3.5380
_cell_volume                     573.23(10)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Xcalibur Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.828
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3698
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.060
_diffrn_reflns_theta_min         3.166
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       prism
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0416P)²+0.1017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2049
_reflns_number_total             2308
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yp3167sup1.cif
_cod_data_source_block           1
_cod_original_cell_volume        573.23(9)
_cod_database_code               2021397
_shelx_shelxl_version_number     2014/7
_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.
;
_exptl_absorpt_special_details
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
C1A C 0.13789(19) 0.24741(18) 0.69369(9) 0.0151(3) Uani 1 1 d
C2A C 0.1030(2) 0.35787(19) 0.77285(9) 0.0164(3) Uani 1 1 d
C3A C -0.1055(2) 0.2893(2) 0.80572(10) 0.0195(3) Uani 1 1 d
H3A H -0.131(3) 0.371(2) 0.8614(12) 0.028(4) Uiso 1 1 d
C4A C -0.2757(2) 0.1096(2) 0.76306(10) 0.0199(3) Uani 1 1 d
H4A H -0.416(2) 0.063(2) 0.7879(11) 0.020(4) Uiso 1 1 d
C5A C -0.2405(2) -0.0021(2) 0.68600(10) 0.0192(3) Uani 1 1 d
H5A H -0.358(2) -0.128(2) 0.6569(11) 0.025(4) Uiso 1 1 d
C6A C -0.0344(2) 0.06825(19) 0.65114(10) 0.0172(3) Uani 1 1 d
H6A H -0.009(2) -0.005(2) 0.5946(12) 0.023(4) Uiso 1 1 d
C7A C 0.3557(2) 0.33058(19) 0.65184(10) 0.0159(3) Uani 1 1 d
O71A O 0.37644(15) 0.20601(14) 0.58360(7) 0.0212(2) Uani 1 1 d
H71A H 0.515(4) 0.269(3) 0.5618(16) 0.070(7) Uiso 1 1 d
O72A O 0.49732(15) 0.49833(14) 0.67712(8) 0.0248(2) Uani 1 1 d
C8A C 0.2823(2) 0.5490(2) 0.82548(10) 0.0201(3) Uani 1 1 d
O81A O 0.42988(17) 0.51504(16) 0.88979(8) 0.0320(3) Uani 1 1 d
H81A H 0.548(3) 0.640(3) 0.9188(15) 0.056(6) Uiso 1 1 d
O82A O 0.27875(15) 0.71212(14) 0.81401(8) 0.0281(3) Uani 1 1 d
N1B N 0.78422(17) 0.39411(16) 0.52281(8) 0.0176(2) Uani 1 1 d
C2B C 0.8609(2) 0.3292(2) 0.44645(10) 0.0184(3) Uani 1 1 d
H2B H 0.766(2) 0.207(2) 0.4058(11) 0.021(4) Uiso 1 1 d
C3B C 1.0753(2) 0.4349(2) 0.42354(10) 0.0179(3) Uani 1 1 d
H3B H 1.132(2) 0.391(2) 0.3694(11) 0.018(3) Uiso 1 1 d
N1C N 0.79526(18) 0.84410(17) 0.96575(9) 0.0233(3) Uani 1 1 d
C2C C 0.9755(2) 0.8705(2) 0.92202(10) 0.0233(3) Uani 1 1 d
H2C H 0.955(2) 0.779(2) 0.8670(12) 0.027(4) Uiso 1 1 d
C3C C 1.1790(2) 1.0257(2) 0.95620(11) 0.0245(3) Uani 1 1 d
H3C H 1.307(3) 1.044(2) 0.9244(12) 0.031(4) Uiso 1 1 d
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
C6A C1A C2A 119.62(12) . .
C6A C1A C7A 121.03(11) . .
C2A C1A C7A 119.24(11) . .
C3A C2A C1A 119.33(12) . .
C3A C2A C8A 117.69(11) . .
C1A C2A C8A 122.98(11) . .
C4A C3A C2A 120.47(12) . .
C4A C3A H3A 120.3(9) . .
C2A C3A H3A 119.2(9) . .
C5A C4A C3A 120.33(12) . .
C5A C4A H4A 120.3(9) . .
C3A C4A H4A 119.3(9) . .
C4A C5A C6A 119.39(12) . .
C4A C5A H5A 120.4(9) . .
C6A C5A H5A 120.2(9) . .
C5A C6A C1A 120.82(12) . .
C5A C6A H6A 120.5(9) . .
C1A C6A H6A 118.7(9) . .
O72A C7A O71A 123.61(12) . .
O72A C7A C1A 122.55(11) . .
O71A C7A C1A 113.83(11) . .
C7A O71A H71A 108.1(13) . .
O82A C8A O81A 125.10(12) . .
O82A C8A C2A 122.63(12) . .
O81A C8A C2A 112.07(11) . .
C8A O81A H81A 110.3(11) . .
C2B N1B C3B 116.79(11) . 2_766
N1B C2B C3B 121.49(12) . .
N1B C2B H2B 119.6(9) . .
C3B C2B H2B 118.9(9) . .
N1B C3B C2B 121.71(12) 2_766 .
N1B C3B H3B 115.7(9) 2_766 .
C2B C3B H3B 122.6(9) . .
C3C N1C C2C 116.87(12) 2_777 .
N1C C2C C3C 121.42(12) . .
N1C C2C H2C 116.2(10) . .
C3C C2C H2C 122.4(10) . .
N1C C3C C2C 121.71(13) 2_777 .
N1C C3C H3C 117.3(10) 2_777 .
C2C C3C H3C 121.0(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A C6A 1.3938(18) .
C1A C2A 1.4026(17) .
C1A C7A 1.4975(17) .
C2A C3A 1.3922(18) .
C2A C8A 1.5061(17) .
C3A C4A 1.3913(19) .
C3A H3A 1.010(15) .
C4A C5A 1.3893(19) .
C4A H4A 0.954(15) .
C5A C6A 1.3894(18) .
C5A H5A 0.970(15) .
C6A H6A 0.974(15) .
C7A O72A 1.2141(15) .
C7A O71A 1.3267(15) .
O71A H71A 0.93(2) .
C8A O82A 1.2156(16) .
C8A O81A 1.3174(16) .
O81A H81A 0.96(2) .
N1B C2B 1.3366(16) .
N1B C3B 1.3403(17) 2_766
C2B C3B 1.3880(18) .
C2B H2B 0.962(15) .
C3B N1B 1.3403(17) 2_766
C3B H3B 0.949(15) .
N1C C3C 1.3328(17) 2_777
N1C C2C 1.3340(18) .
C2C C3C 1.382(2) .
C2C H2C 0.933(15) .
C3C N1C 1.3328(17) 2_777
C3C H3C 0.952(16) .
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_4
C6A C1A C2A C3A -1.73(18) . .
C7A C1A C2A C3A 174.55(11) . .
C6A C1A C2A C8A 177.84(11) . .
C7A C1A C2A C8A -5.87(17) . .
C1A C2A C3A C4A 2.13(19) . .
C8A C2A C3A C4A -177.47(11) . .
C2A C3A C4A C5A -0.9(2) . .
C3A C4A C5A C6A -0.67(19) . .
C4A C5A C6A C1A 1.05(19) . .
C2A C1A C6A C5A 0.15(18) . .
C7A C1A C6A C5A -176.07(11) . .
C6A C1A C7A O72A 169.61(12) . .
C2A C1A C7A O72A -6.63(18) . .
C6A C1A C7A O71A -9.08(16) . .
C2A C1A C7A O71A 174.69(10) . .
C3A C2A C8A O82A -69.34(17) . .
C1A C2A C8A O82A 111.08(15) . .
C3A C2A C8A O81A 105.91(13) . .
C1A C2A C8A O81A -73.67(15) . .
C3B N1B C2B C3B -0.4(2) 2_766 .
N1B C2B C3B N1B 0.4(2) . 2_766
C3C N1C C2C C3C 0.0(2) 2_777 .
N1C C2C C3C N1C 0.0(2) . 2_777

_cod_database_fobs_code 2021397
