#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/39/7103920.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_7103920
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(C H2 O2)'
_chemical_formula_sum            'C6 H8 N2 O4'
_chemical_formula_weight         172.14
_chemical_name_common            'pyrazine / formic acid'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.068(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.6994(1)
_cell_length_b                   7.0340(3)
_cell_length_c                   16.1607(9)
_cell_measurement_reflns_used    3743
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.02
_cell_volume                     418.17(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 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.1556
_diffrn_reflns_av_sigmaI/netI    0.0862
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2895
_diffrn_reflns_theta_full        25.32
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         3.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9771
_exptl_absorpt_correction_T_min  0.9604
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             180
_exptl_crystal_size_length       0.35
_exptl_crystal_size_rad          0.10
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     59
_refine_ls_number_reflns         760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0723
_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)+(0.1003P)²+0.0876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1839
_refine_ls_wR_factor_ref         0.1925
_reflns_number_gt                661
_reflns_number_total             760
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b208904a.txt
_cod_data_source_block           ab0210
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7103920
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 0.3994(5) 0.9644(2) 0.38667(10) 0.0559(6) Uani 1 1 d . . .
H1 H 0.281(11) 0.873(5) 0.414(2) 0.096(11) Uiso 1 1 d . . .
O2 O 0.1775(5) 0.8171(2) 0.26999(10) 0.0597(6) Uani 1 1 d . . .
C1 C 0.3318(6) 0.9476(3) 0.30605(14) 0.0510(7) Uani 1 1 d . . .
H1A H 0.4120 1.0478 0.2730 0.061 Uiso 1 1 calc R . .
N1A N 0.1374(5) 0.6608(2) 0.46444(11) 0.0455(6) Uani 1 1 d . . .
C2A C 0.0975(6) 0.6525(3) 0.54571(13) 0.0464(7) Uani 1 1 d . . .
H2AA H 0.1640 0.7592 0.5800 0.056 Uiso 1 1 calc R . .
C1A C 0.0379(6) 0.5075(3) 0.41936(13) 0.0469(7) Uani 1 1 d . . .
H1AA H 0.0610 0.5086 0.3614 0.056 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0709(12) 0.0392(10) 0.0575(11) 0.0018(7) 0.0061(8) -0.0146(7)
O2 0.0789(13) 0.0437(10) 0.0562(11) -0.0006(7) 0.0060(9) -0.0058(8)
C1 0.0608(14) 0.0362(11) 0.0569(13) 0.0045(9) 0.0097(11) -0.0025(9)
N1A 0.0480(11) 0.0369(10) 0.0516(11) 0.0019(7) 0.0049(8) -0.0038(7)
C2A 0.0505(13) 0.0372(11) 0.0510(12) -0.0080(9) 0.0036(9) -0.0037(8)
C1A 0.0528(13) 0.0454(12) 0.0426(11) -0.0014(9) 0.0051(10) -0.0026(8)
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 O1 H1 111(2) . . ?
O2 C1 O1 125.8(2) . . ?
O2 C1 H1A 117.1 . . ?
O1 C1 H1A 117.1 . . ?
C1A N1A C2A 116.64(17) . . ?
N1A C2A C1A 121.39(18) . 3_566 ?
N1A C2A H2AA 119.3 . . ?
C1A C2A H2AA 119.3 3_566 . ?
N1A C1A C2A 121.96(18) . 3_566 ?
N1A C1A H1AA 119.0 . . ?
C2A C1A H1AA 119.0 3_566 . ?
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
O1 C1 1.306(3) . ?
O1 H1 0.92(4) . ?
O2 C1 1.199(3) . ?
C1 H1A 0.9500 . ?
N1A C1A 1.331(3) . ?
N1A C2A 1.338(3) . ?
C2A C1A 1.377(3) 3_566 ?
C2A H2AA 0.9500 . ?
C1A C2A 1.377(3) 3_566 ?
C1A H1AA 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
C1A N1A C2A C1A 0.4(3) . . . 3_566 ?
C2A N1A C1A C2A -0.4(3) . . . 3_566 ?
