#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/39/7103921.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_7103921
loop_
_publ_author_name
'Andrew Bond'
_publ_section_title
;
In situ co-crystallisation as a tool for
low-temperature crystal engineering
;
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/b208904a
_journal_year                    2003
_chemical_formula_moiety         'C4 H4 N2, 2(C2 H4 O2)'
_chemical_formula_sum            'C8 H12 N2 O4'
_chemical_formula_weight         200.20
_chemical_name_common            'pyrazine / acetic acid'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                70.076(1)
_cell_angle_beta                 86.667(1)
_cell_angle_gamma                89.925(2)
_cell_formula_units_Z            2
_cell_length_a                   5.4869(2)
_cell_length_b                   8.1885(2)
_cell_length_c                   11.9960(4)
_cell_measurement_reflns_used    3505
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     505.76(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor, 1997)
;
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5274
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.72
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             212
_exptl_crystal_size_length       0.35
_exptl_crystal_size_rad          0.10
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2287
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0518
_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)+(0.0677P)²+0.1511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                1904
_reflns_number_total             2287
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b208904a.txt
_cod_data_source_block           ab0209
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7103921
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2_1 O -0.1440(2) 0.32153(17) -0.00707(11) 0.0460(3) Uani 1 1 d . . .
O1_1 O -0.0215(2) 0.20358(16) 0.17682(10) 0.0426(3) Uani 1 1 d . . .
H1_1 H 0.093(5) 0.149(3) 0.136(2) 0.077(8) Uiso 1 1 d . . .
C1_1 C -0.1633(3) 0.3057(2) 0.09716(15) 0.0353(3) Uani 1 1 d . . .
C2_1 C -0.3504(3) 0.3953(2) 0.15031(16) 0.0444(4) Uani 1 1 d . . .
H2A_1 H -0.4125 0.4950 0.0875 0.067 Uiso 1 1 calc R . .
H2B_1 H -0.2757 0.4354 0.2089 0.067 Uiso 1 1 calc R . .
H2C_1 H -0.4854 0.3140 0.1894 0.067 Uiso 1 1 calc R . .
N1A_1 N 0.3190(2) 0.05536(18) 0.06390(12) 0.0380(3) Uani 1 1 d . . .
C1A_1 C 0.3234(3) 0.1024(2) -0.05361(16) 0.0392(4) Uani 1 1 d . . .
H1AA_1 H 0.1993 0.1753 -0.0950 0.047 Uiso 1 1 calc R . .
C2A_1 C 0.4952(3) -0.0477(2) 0.11734(15) 0.0388(4) Uani 1 1 d . . .
H2AA_1 H 0.4971 -0.0850 0.2014 0.047 Uiso 1 1 calc R . .
O2_2 O 0.2155(2) 0.44093(17) -0.39220(12) 0.0484(3) Uani 1 1 d . . .
O1_2 O -0.0370(2) 0.21128(15) -0.33587(11) 0.0419(3) Uani 1 1 d . . .
H1_2 H 0.093(4) 0.163(3) -0.370(2) 0.064(6) Uiso 1 1 d . . .
C1_2 C 0.0194(3) 0.3743(2) -0.34952(13) 0.0314(3) Uani 1 1 d . . .
C2_2 C -0.1833(3) 0.4641(2) -0.30628(15) 0.0372(4) Uani 1 1 d . . .
H2D_2 H -0.1449 0.5887 -0.3315 0.056 Uiso 1 1 calc R . .
H2E_2 H -0.2020 0.4161 -0.2194 0.056 Uiso 1 1 calc R . .
H2F_2 H -0.3357 0.4461 -0.3396 0.056 Uiso 1 1 calc R . .
N1A_2 N 0.3211(2) 0.06645(17) -0.44135(12) 0.0353(3) Uani 1 1 d . . .
C2A_2 C 0.3004(3) -0.0921(2) -0.44764(15) 0.0367(4) Uani 1 1 d . . .
H2AB_2 H 0.1598 -0.1616 -0.4110 0.044 Uiso 1 1 calc R . .
C1A_2 C 0.5214(3) 0.1588(2) -0.49370(14) 0.0343(3) Uani 1 1 d . . .
H1AB_2 H 0.5429 0.2724 -0.4909 0.041 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
_geom_angle_publ_flag
C1_1 O1_1 H1_1 108.3(15) . . ?
O2_1 C1_1 O1_1 122.94(14) . . ?
O2_1 C1_1 C2_1 124.15(15) . . ?
O1_1 C1_1 C2_1 112.90(14) . . ?
C1_1 C2_1 H2A_1 109.5 . . ?
C1_1 C2_1 H2B_1 109.5 . . ?
H2A_1 C2_1 H2B_1 109.5 . . ?
C1_1 C2_1 H2C_1 109.5 . . ?
H2A_1 C2_1 H2C_1 109.5 . . ?
H2B_1 C2_1 H2C_1 109.5 . . ?
C2A_1 N1A_1 C1A_1 116.79(13) . . ?
N1A_1 C1A_1 C2A_1 121.54(15) . 2_655 ?
N1A_1 C1A_1 H1AA_1 119.2 . . ?
C2A_1 C1A_1 H1AA_1 119.2 2_655 . ?
N1A_1 C2A_1 C1A_1 121.67(15) . 2_655 ?
N1A_1 C2A_1 H2AA_1 119.2 . . ?
C1A_1 C2A_1 H2AA_1 119.2 2_655 . ?
C1_2 O1_2 H1_2 109.6(14) . . ?
O2_2 C1_2 O1_2 122.66(14) . . ?
O2_2 C1_2 C2_2 124.60(15) . . ?
O1_2 C1_2 C2_2 112.75(13) . . ?
C1_2 C2_2 H2D_2 109.5 . . ?
C1_2 C2_2 H2E_2 109.5 . . ?
H2D_2 C2_2 H2E_2 109.5 . . ?
C1_2 C2_2 H2F_2 109.5 . . ?
H2D_2 C2_2 H2F_2 109.5 . . ?
H2E_2 C2_2 H2F_2 109.5 . . ?
C2A_2 N1A_2 C1A_2 116.97(13) . . ?
N1A_2 C2A_2 C1A_2 121.82(14) . 2_654 ?
N1A_2 C2A_2 H2AB_2 119.1 . . ?
C1A_2 C2A_2 H2AB_2 119.1 2_654 . ?
N1A_2 C1A_2 C2A_2 121.21(14) . 2_654 ?
N1A_2 C1A_2 H1AB_2 119.4 . . ?
C2A_2 C1A_2 H1AB_2 119.4 2_654 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2_1 C1_1 1.211(2) . ?
O1_1 C1_1 1.326(2) . ?
O1_1 H1_1 0.97(3) . ?
C1_1 C2_1 1.496(2) . ?
C2_1 H2A_1 0.9800 . ?
C2_1 H2B_1 0.9800 . ?
C2_1 H2C_1 0.9800 . ?
N1A_1 C2A_1 1.327(2) . ?
N1A_1 C1A_1 1.327(2) . ?
C1A_1 C2A_1 1.385(2) 2_655 ?
C1A_1 H1AA_1 0.9500 . ?
C2A_1 C1A_1 1.385(2) 2_655 ?
C2A_1 H2AA_1 0.9500 . ?
O2_2 C1_2 1.2101(18) . ?
O1_2 C1_2 1.3235(19) . ?
O1_2 H1_2 0.95(3) . ?
C1_2 C2_2 1.4952(19) . ?
C2_2 H2D_2 0.9800 . ?
C2_2 H2E_2 0.9800 . ?
C2_2 H2F_2 0.9800 . ?
N1A_2 C2A_2 1.331(2) . ?
N1A_2 C1A_2 1.331(2) . ?
C2A_2 C1A_2 1.389(2) 2_654 ?
C2A_2 H2AB_2 0.9500 . ?
C1A_2 C2A_2 1.389(2) 2_654 ?
C1A_2 H1AB_2 0.9500 . ?
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
_geom_torsion_publ_flag
C2A_1 N1A_1 C1A_1 C2A_1 -0.6(3) . . . 2_655 ?
C1A_1 N1A_1 C2A_1 C1A_1 0.6(3) . . . 2_655 ?
C1A_2 N1A_2 C2A_2 C1A_2 -0.2(3) . . . 2_654 ?
C2A_2 N1A_2 C1A_2 C2A_2 0.2(2) . . . 2_654 ?
