#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:53:33 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180361 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/30/7203097.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_7203097
loop_
_publ_author_name
'Babu, N. Jagadeesh'
'Nangia, Ashwini'
_publ_section_title
;
 High Z′ polymorphs have shorter C--H⋯O interactions and
 O--H⋯O hydrogen bonds
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              980
_journal_paper_doi               10.1039/b711739f
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         ' C2 H2 N O, 0.5(C4 H4 N2 O2)'
_chemical_formula_sum            'C4 H4 N2 O2'
_chemical_formula_weight         112.09
_chemical_name_common            Pyrazine-N,N'-dioxide
_chemical_name_systematic
;
Pyrazine-N,N'-dioxide
;
_chemical_temperature_decomposition 560
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.8672(18)
_cell_length_b                   12.2217(19)
_cell_length_c                   6.4287(10)
_cell_measurement_reflns_used    1512
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      3.33
_cell_volume                     932.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4790
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0605
_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)+(0.0730P)²+0.2522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1584
_reflns_number_gt                643
_reflns_number_total             956
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b711739f.txt
_cod_data_source_block           pnma
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been '560K
(decomp) '. The value '560K (decomp) ' was changed to '560'.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'Pnma '
_cod_database_code               7203097
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
N2 N 0.5620(2) 0.2500 0.1955(4) 0.0328(7) Uani 1 2 d S . .
O2 O 0.4985(2) 0.2500 0.3607(4) 0.0466(7) Uani 1 2 d S . .
O1 O 0.7642(2) 0.2500 -0.3092(4) 0.0714(10) Uani 1 2 d S . .
C1 C 0.7432(3) 0.2500 0.0447(5) 0.0381(9) Uani 1 2 d S . .
H1 H 0.8211 0.2500 0.0613 0.046 Uiso 1 2 calc SR . .
C3 C 0.5188(3) 0.2500 0.0012(5) 0.0368(9) Uani 1 2 d S . .
H3 H 0.4410 0.2500 -0.0157 0.044 Uiso 1 2 calc SR . .
C2 C 0.6762(3) 0.2500 0.2151(5) 0.0369(9) Uani 1 2 d S . .
H2 H 0.7085 0.2500 0.3469 0.044 Uiso 1 2 calc SR . .
N1 N 0.6989(2) 0.2500 -0.1494(4) 0.0424(8) Uani 1 2 d S . .
C4 C 0.5847(3) 0.2500 -0.1677(5) 0.0424(9) Uani 1 2 d S . .
H4 H 0.5520 0.2500 -0.2992 0.051 Uiso 1 2 calc SR . .
O3 O 0.36647(16) 0.49092(17) 0.1660(3) 0.0577(7) Uani 1 1 d . . .
N3 N 0.43087(18) 0.49625(16) 0.3286(3) 0.0365(6) Uani 1 1 d . . .
C5 C 0.3878(2) 0.4920(2) 0.5233(4) 0.0378(7) Uani 1 1 d . . .
H5 H 0.3103 0.4869 0.5413 0.045 Uiso 1 1 calc R . .
C6 C 0.5444(2) 0.50498(19) 0.3080(4) 0.0370(7) Uani 1 1 d . . .
H6 H 0.5760 0.5089 0.1758 0.044 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
N2 0.0243(15) 0.0462(17) 0.0279(15) 0.000 0.0006(11) 0.000
O2 0.0301(14) 0.0754(19) 0.0343(13) 0.000 0.0105(10) 0.000
O1 0.0403(17) 0.140(3) 0.0341(16) 0.000 0.0142(12) 0.000
C1 0.0231(18) 0.055(2) 0.036(2) 0.000 -0.0004(14) 0.000
C3 0.0213(17) 0.052(2) 0.0370(19) 0.000 -0.0024(14) 0.000
C2 0.0237(17) 0.054(2) 0.0334(19) 0.000 -0.0026(14) 0.000
N1 0.0313(17) 0.065(2) 0.0307(16) 0.000 0.0012(12) 0.000
C4 0.035(2) 0.061(2) 0.0313(19) 0.000 -0.0070(16) 0.000
O3 0.0364(12) 0.1026(18) 0.0342(11) -0.0040(11) -0.0122(8) -0.0007(10)
N3 0.0259(11) 0.0541(14) 0.0296(11) -0.0031(9) -0.0036(8) 0.0006(9)
C5 0.0223(12) 0.0509(15) 0.0402(14) -0.0035(12) 0.0028(10) -0.0013(10)
C6 0.0268(14) 0.0526(16) 0.0315(13) -0.0011(11) 0.0076(10) -0.0009(10)
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
O2 N2 C3 122.3(3) . . ?
O2 N2 C2 120.0(3) . . ?
C3 N2 C2 117.6(3) . . ?
C2 C1 N1 121.2(3) . . ?
C2 C1 H1 119.4 . . ?
N1 C1 H1 119.4 . . ?
C4 C3 N2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
N2 C3 H3 119.0 . . ?
C1 C2 N2 120.7(3) . . ?
C1 C2 H2 119.7 . . ?
N2 C2 H2 119.7 . . ?
O1 N1 C1 120.1(3) . . ?
O1 N1 C4 122.1(3) . . ?
C1 N1 C4 117.8(3) . . ?
C3 C4 N1 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
N1 C4 H4 119.6 . . ?
O3 N3 C5 121.4(2) . . ?
O3 N3 C6 120.7(2) . . ?
C5 N3 C6 117.9(2) . . ?
C6 C5 N3 121.2(2) 5_666 . ?
C6 C5 H5 119.4 5_666 . ?
N3 C5 H5 119.4 . . ?
C5 C6 N3 120.9(2) 5_666 . ?
C5 C6 H6 119.5 5_666 . ?
N3 C6 H6 119.5 . . ?
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
N2 O2 1.302(3) . ?
N2 C3 1.350(4) . ?
N2 C2 1.361(4) . ?
O1 N1 1.287(3) . ?
C1 C2 1.354(5) . ?
C1 N1 1.354(4) . ?
C1 H1 0.9300 . ?
C3 C4 1.338(5) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
N1 C4 1.361(4) . ?
C4 H4 0.9300 . ?
O3 N3 1.297(2) . ?
N3 C5 1.353(3) . ?
N3 C6 1.358(3) . ?
C5 C6 1.350(4) 5_666 ?
C5 H5 0.9300 . ?
C6 C5 1.350(4) 5_666 ?
C6 H6 0.9300 . ?
