#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:19:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180387 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/56/7205665.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_7205665
loop_
_publ_author_name
'Braga, Dario'
'Grepioni, Fabrizia'
'Lampronti, Giulio I.'
_publ_section_title
;
 Supramolecular metathesis: co-former exchange in co-crystals of
 pyrazine with (R,R)-, (S,S)-, (R,S)- and (S,S/R,R)-tartaric acid
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              3122
_journal_paper_doi               10.1039/c0ce00576b
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C8 H10 N2 O6'
_chemical_formula_sum            'C8 H10 N2 O6'
_chemical_formula_weight         230.18
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-04-07T10:53:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 96.315(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4966(4)
_cell_length_b                   5.1521(2)
_cell_length_c                   17.0937(6)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1006.34(6)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.818
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4566
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         29.32
_diffrn_reflns_theta_min         2.4
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.084
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0483P)²+0.2180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.105
_reflns_number_gt                1538
_reflns_number_total             2258
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00576b.txt
_cod_data_source_block           ract1py1
_cod_database_code               7205665
loop_
_symmetry_equiv_pos_as_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_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.51278(15) 0.1470(4) 0.67697(11) 0.0355(5) Uani d . 1 . . C
C2 0.62010(14) -0.0076(4) 0.66294(10) 0.0315(4) Uani d . 1 . . C
H2 0.6113 -0.1853 0.6819 0.038 Uiso calc R 1 . . H
C3 0.63212(14) -0.0155(4) 0.57439(10) 0.0290(4) Uani d . 1 . . C
H3 0.5739 -0.137 0.5493 0.035 Uiso calc R 1 . . H
C4 0.75346(15) -0.1186(4) 0.56403(10) 0.0303(4) Uani d . 1 . . C
O1 0.51841(12) 0.3460(3) 0.71395(9) 0.0560(5) Uani d . 1 . . O
O2 0.41513(11) 0.0403(3) 0.64539(9) 0.0519(5) Uani d . 1 . . O
O3 0.72136(10) 0.1040(3) 0.70429(7) 0.0441(4) Uani d . 1 . . O
H300 0.7029 0.2339 0.7278 0.066 Uiso calc R 1 . . H
O4 0.61251(12) 0.2292(3) 0.53927(8) 0.0421(4) Uani d . 1 . . O
O5 0.76918(11) -0.3573(3) 0.59164(8) 0.0410(4) Uani d . 1 . . O
O6 0.82687(12) 0.0032(3) 0.53546(9) 0.0523(4) Uani d . 1 . . O
H200 0.353(2) 0.140(6) 0.6520(16) 0.089(9) Uiso d . 1 . . H
H400 0.667(2) 0.345(5) 0.5582(13) 0.062(8) Uiso d . 1 . . H
H500 0.846(2) -0.406(5) 0.5922(14) 0.070(8) Uiso d . 1 . . H
C6 0.87321(16) -0.2041(4) 0.32098(11) 0.0394(5) Uani d . 1 . . C
H6 0.8598 -0.0623 0.2875 0.047 Uiso calc R 1 . . H
C8 0.91935(17) -0.6112(4) 0.41364(11) 0.0413(5) Uani d . 1 . . C
H8 0.9329 -0.7559 0.4459 0.05 Uiso calc R 1 . . H
C7 0.80658(17) -0.5261(5) 0.39488(12) 0.0452(6) Uani d . 1 . . C
H7 0.7455 -0.6138 0.4148 0.054 Uiso calc R 1 . . H
C5 0.98607(16) -0.2884(4) 0.34051(10) 0.0359(5) Uani d . 1 . . C
H5 1.0473 -0.201 0.3208 0.043 Uiso calc R 1 . . H
N1 1.00919(13) -0.4926(4) 0.38704(9) 0.0367(4) Uani d . 1 . . N
N2 0.78283(13) -0.3192(4) 0.34850(10) 0.0433(5) Uani d . 1 . . N
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
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
O1 C1 O2 124.59(18) . . ?
O1 C1 C2 122.38(17) . . ?
O2 C1 C2 113.02(18) . . ?
O3 C2 C1 110.37(16) . . ?
O3 C2 C3 110.17(14) . . ?
C1 C2 C3 109.54(14) . . ?
O4 C3 C4 111.71(15) . . ?
O4 C3 C2 111.71(16) . . ?
C4 C3 C2 107.89(13) . . ?
O6 C4 O5 123.91(18) . . ?
O6 C4 C3 124.11(18) . . ?
O5 C4 C3 111.97(16) . . ?
N2 C6 C5 121.86(19) . . ?
N1 C8 C7 121.7(2) . . ?
N2 C7 C8 121.23(18) . . ?
N1 C5 C6 121.17(18) . . ?
C8 N1 C5 117.34(17) . . ?
C6 N2 C7 116.70(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.203(2) ?
C1 O2 . 1.312(2) ?
C1 C2 . 1.510(3) ?
C2 O3 . 1.416(2) ?
C2 C3 . 1.536(2) ?
C3 O4 . 1.404(2) ?
C3 C4 . 1.521(2) ?
C4 O6 . 1.198(2) ?
C4 O5 . 1.323(2) ?
C6 N2 . 1.327(2) ?
C6 C5 . 1.374(3) ?
C8 N1 . 1.323(3) ?
C8 C7 . 1.373(3) ?
C7 N2 . 1.339(3) ?
C5 N1 . 1.328(3) ?
