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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/2/02/13/2021398.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_2021398
loop_
_publ_author_name
'Dutkiewicz, Grzegorz'
'Dutkiewicz, Edward'
'Kubicki, Maciej'
_publ_section_title
;
 Cocrystals of pyrazine and benzene polycarboxylic acids
;
_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, C9 H6 O6'
_chemical_formula_moiety         'C4 H4 N2, C9 H6 O6'
_chemical_formula_sum            'C13 H10 N2 O6'
_chemical_formula_weight         290.23
_chemical_name_common
;
Pyrazine--hemimellitic acid (1/1)
;
_chemical_name_systematic
;
Pyrazine--benzene-1,2,3-tricarboxylic 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                115.029(10)
_cell_angle_beta                 112.471(10)
_cell_angle_gamma                92.672(9)
_cell_formula_units_Z            2
_cell_length_a                   7.7184(9)
_cell_length_b                   9.9393(10)
_cell_length_c                   10.0300(10)
_cell_measurement_reflns_used    1758
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      26.3940
_cell_measurement_theta_min      4.5280
_cell_volume                     624.00(15)
_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_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.910
_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  0.0163
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4116
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.618
_diffrn_reflns_theta_min         3.275
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0346
_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)+(0.0457P)²+0.1205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2083
_reflns_number_total             2396
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yp3167sup1.cif
_cod_data_source_block           2
_cod_database_code               2021398
_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 0.77882(19) 0.80344(15) 0.27507(16) 0.0137(3) Uani 1 1 d
C2A C 0.63009(19) 0.70793(15) 0.26611(16) 0.0130(3) Uani 1 1 d
C3A C 0.62151(19) 0.55080(15) 0.20468(16) 0.0134(3) Uani 1 1 d
C4A C 0.7578(2) 0.49160(16) 0.15290(16) 0.0155(3) Uani 1 1 d
H4A H 0.750(2) 0.3828(19) 0.1076(18) 0.016(4) Uiso 1 1 d
C5A C 0.9085(2) 0.58751(17) 0.16845(17) 0.0159(3) Uani 1 1 d
H5A H 1.004(2) 0.5487(19) 0.140(2) 0.023(4) Uiso 1 1 d
C6A C 0.9190(2) 0.74282(16) 0.23014(16) 0.0149(3) Uani 1 1 d
H6A H 1.024(2) 0.8093(18) 0.2436(19) 0.017(4) Uiso 1 1 d
C7A C 0.78911(19) 0.97030(16) 0.33081(16) 0.0145(3) Uani 1 1 d
O71A O 0.93572(14) 1.04177(12) 0.32928(13) 0.0205(3) Uani 1 1 d
H71A H 0.938(3) 1.152(3) 0.368(3) 0.071(7) Uiso 1 1 d
O72A O 0.67285(15) 1.03387(11) 0.37084(13) 0.0232(3) Uani 1 1 d
C8A C 0.4806(2) 0.77328(15) 0.31933(17) 0.0150(3) Uani 1 1 d
O81A O 0.54245(15) 0.82580(12) 0.48002(12) 0.0205(3) Uani 1 1 d
H81A H 0.450(3) 0.869(2) 0.510(3) 0.053(6) Uiso 1 1 d
O82A O 0.32857(14) 0.77818(11) 0.22763(12) 0.0204(3) Uani 1 1 d
C9A C 0.46821(19) 0.44580(15) 0.19762(16) 0.0151(3) Uani 1 1 d
O91A O 0.47584(15) 0.30072(12) 0.13041(13) 0.0221(3) Uani 1 1 d
H91A H 0.373(4) 0.244(3) 0.126(3) 0.069(7) Uiso 1 1 d
O92A O 0.35251(15) 0.48904(12) 0.25017(13) 0.0240(3) Uani 1 1 d
N1B N 0.17076(18) 0.11055(14) 0.07462(15) 0.0195(3) Uani 1 1 d
C2B C -0.0016(2) 0.14191(17) 0.02235(18) 0.0190(3) Uani 1 1 d
H2B H -0.005(2) 0.246(2) 0.0359(19) 0.023(4) Uiso 1 1 d
C3B C -0.1722(2) 0.03190(17) -0.05225(18) 0.0205(3) Uani 1 1 d
H3B H -0.295(3) 0.0579(19) -0.089(2) 0.027(4) Uiso 1 1 d
N1C N 0.96658(17) 1.34142(13) 0.43213(14) 0.0175(3) Uani 1 1 d
C2C C 1.1168(2) 1.42572(17) 0.44258(17) 0.0179(3) Uani 1 1 d
H2C H 1.200(2) 1.3711(19) 0.401(2) 0.022(4) Uiso 1 1 d
C3C C 1.1493(2) 1.58355(17) 0.50973(17) 0.0178(3) Uani 1 1 d
H3C H 1.260(2) 1.6428(17) 0.5157(18) 0.016(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 120.00(12) . .
C6A C1A C7A 118.84(12) . .
C2A C1A C7A 121.16(12) . .
C3A C2A C1A 118.74(12) . .
C3A C2A C8A 120.77(12) . .
C1A C2A C8A 120.48(12) . .
C4A C3A C2A 120.18(12) . .
C4A C3A C9A 119.47(12) . .
C2A C3A C9A 120.33(12) . .
C5A C4A C3A 120.65(13) . .
C5A C4A H4A 119.1(9) . .
C3A C4A H4A 120.2(9) . .
C6A C5A C4A 119.53(13) . .
C6A C5A H5A 119.8(10) . .
C4A C5A H5A 120.6(10) . .
C5A C6A C1A 120.77(12) . .
C5A C6A H6A 119.9(10) . .
C1A C6A H6A 119.3(10) . .
O72A C7A O71A 123.00(13) . .
O72A C7A C1A 123.96(12) . .
O71A C7A C1A 113.03(12) . .
C7A O71A H71A 110.7(14) . .
O82A C8A O81A 125.50(13) . .
O82A C8A C2A 123.72(12) . .
O81A C8A C2A 110.78(11) . .
C8A O81A H81A 108.7(13) . .
O92A C9A O91A 123.61(12) . .
O92A C9A C3A 123.82(12) . .
O91A C9A C3A 112.56(12) . .
C9A O91A H91A 106.8(15) . .
C2B N1B C3B 117.41(13) . 2
N1B C2B C3B 121.56(13) . .
N1B C2B H2B 118.1(10) . .
C3B C2B H2B 120.3(10) . .
N1B C3B C2B 121.03(14) 2 .
N1B C3B H3B 119.2(10) 2 .
C2B C3B H3B 119.8(10) . .
C3C N1C C2C 117.16(13) 2_786 .
N1C C2C C3C 121.28(14) . .
N1C C2C H2C 116.5(10) . .
C3C C2C H2C 122.2(10) . .
N1C C3C C2C 121.56(13) 2_786 .
N1C C3C H3C 118.7(9) 2_786 .
C2C C3C H3C 119.7(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A C6A 1.3933(19) .
C1A C2A 1.4052(19) .
C1A C7A 1.4962(19) .
C2A C3A 1.4028(19) .
C2A C8A 1.5119(19) .
C3A C4A 1.3925(19) .
C3A C9A 1.5008(19) .
C4A C5A 1.385(2) .
C4A H4A 0.968(16) .
C5A C6A 1.383(2) .
C5A H5A 0.932(18) .
C6A H6A 0.948(16) .
C7A O72A 1.2163(17) .
C7A O71A 1.3164(16) .
O71A H71A 0.99(3) .
C8A O82A 1.2013(17) .
C8A O81A 1.3322(17) .
O81A H81A 0.93(2) .
C9A O92A 1.2099(17) .
C9A O91A 1.3240(17) .
O91A H91A 0.93(2) .
N1B C2B 1.336(2) .
N1B C3B 1.3377(19) 2
C2B C3B 1.382(2) .
C2B H2B 0.984(17) .
C3B N1B 1.3377(19) 2
C3B H3B 0.971(18) .
N1C C3C 1.3377(19) 2_786
N1C C2C 1.3416(19) .
C2C C3C 1.385(2) .
C2C H2C 0.957(17) .
C3C N1C 1.3378(19) 2_786
C3C H3C 0.984(15) .
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 -2.77(19) . .
C7A C1A C2A C3A 176.62(11) . .
C6A C1A C2A C8A 178.17(12) . .
C7A C1A C2A C8A -2.44(19) . .
C1A C2A C3A C4A -0.40(19) . .
C8A C2A C3A C4A 178.66(11) . .
C1A C2A C3A C9A 178.27(12) . .
C8A C2A C3A C9A -2.67(19) . .
C2A C3A C4A C5A 3.1(2) . .
C9A C3A C4A C5A -175.60(12) . .
C3A C4A C5A C6A -2.5(2) . .
C4A C5A C6A C1A -0.7(2) . .
C2A C1A C6A C5A 3.4(2) . .
C7A C1A C6A C5A -176.05(12) . .
C6A C1A C7A O72A 179.16(13) . .
C2A C1A C7A O72A -0.2(2) . .
C6A C1A C7A O71A 0.40(17) . .
C2A C1A C7A O71A -179.00(12) . .
C3A C2A C8A O82A -86.80(17) . .
C1A C2A C8A O82A 92.24(17) . .
C3A C2A C8A O81A 94.20(14) . .
C1A C2A C8A O81A -86.75(15) . .
C4A C3A C9A O92A 174.85(12) . .
C2A C3A C9A O92A -3.8(2) . .
C4A C3A C9A O91A -3.90(18) . .
C2A C3A C9A O91A 177.42(11) . .
C3B N1B C2B C3B -0.1(2) 2 .
N1B C2B C3B N1B 0.1(2) . 2
C3C N1C C2C C3C -0.4(2) 2_786 .
N1C C2C C3C N1C 0.5(2) . 2_786

_cod_database_fobs_code 2021398
