#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/45/2224535.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_2224535
loop_
_publ_author_name
'Gratton, Jessica L.'
'Knaust, Jacqueline M.'
_publ_section_title
;
 2-Methylpyrazine 1,4-dioxide
;
_journal_coeditor_code           ZL2250
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3040
_journal_paper_doi               10.1107/S1600536809046534
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C5 H6 N2 O2'
_chemical_formula_moiety         'C5 H6 N2 O2'
_chemical_formula_sum            'C5 H6 N2 O2'
_chemical_formula_weight         126.12
_chemical_name_common            '2-methylpyrazine 1,4-dioxide'
_chemical_name_systematic
;
2-Methylpyrazine 1,4-dioxide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c 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                   6.3953(9)
_cell_length_b                   12.2472(18)
_cell_length_c                   13.6613(19)
_cell_measurement_reflns_used    1890
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.5295
_cell_measurement_theta_min      2.982
_cell_volume                     1070.0(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'X-SEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω
_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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5556
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.81
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.762900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.309
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0458
_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)+(0.0537P)²+0.6359P]where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                1407
_reflns_number_total             1708
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2250.cif
_cod_data_source_block           I
_cod_database_code               2224535
_cod_database_fobs_code          2224535
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
O O1 0.33101(13) 0.64269(8) 0.41676(7) 0.0164(2) Uani d . 1 . .
O O2 0.99921(14) 0.59296(8) 0.64921(7) 0.0183(2) Uani d . 1 . .
N N1 0.49403(15) 0.63273(8) 0.47271(8) 0.0122(2) Uani d . 1 . .
N N2 0.83721(15) 0.60672(9) 0.59294(8) 0.0128(2) Uani d . 1 . .
C C1 0.47150(19) 0.62449(10) 0.57203(9) 0.0136(2) Uani d . 1 . .
H H1 0.3386 0.6279 0.5995 0.016 Uiso calc R 1 . .
C C2 0.64141(19) 0.61132(10) 0.63137(9) 0.0142(2) Uani d . 1 . .
H H2 0.6230 0.6055 0.6987 0.017 Uiso calc R 1 . .
C C3 0.86033(18) 0.61629(10) 0.49464(9) 0.0126(2) Uani d . 1 . .
H H3 0.9940 0.6141 0.4679 0.015 Uiso calc R 1 . .
C C4 0.69092(18) 0.62919(10) 0.43327(9) 0.0125(2) Uani d . 1 . .
C C5 0.7106(2) 0.63969(11) 0.32565(9) 0.0165(2) Uani d . 1 . .
H H5A 0.6439 0.7059 0.3046 0.025 Uiso calc R 1 . .
H H5B 0.6448 0.5783 0.2946 0.025 Uiso calc R 1 . .
H H5C 0.8559 0.6417 0.3080 0.025 Uiso calc R 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0092(4) 0.0223(5) 0.0177(4) 0.0005(3) -0.0044(3) 0.0008(3)
O2 0.0112(4) 0.0298(5) 0.0140(4) 0.0004(3) -0.0053(3) 0.0002(4)
N1 0.0090(4) 0.0139(4) 0.0138(5) 0.0001(3) -0.0009(4) -0.0004(3)
N2 0.0103(4) 0.0169(5) 0.0113(5) -0.0005(3) -0.0013(4) -0.0003(4)
C1 0.0118(5) 0.0155(5) 0.0136(5) 0.0000(4) 0.0027(4) 0.0001(4)
C2 0.0137(5) 0.0167(5) 0.0122(5) -0.0006(4) 0.0026(4) -0.0006(4)
C3 0.0097(4) 0.0160(5) 0.0120(5) -0.0007(4) 0.0013(4) -0.0006(4)
C4 0.0104(5) 0.0143(5) 0.0126(5) 0.0000(4) 0.0008(4) -0.0004(4)
C5 0.0142(5) 0.0242(6) 0.0112(5) 0.0008(4) 0.0007(4) 0.0015(5)
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'
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'
H H 0.0000 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 N1 C1 . . 120.41(10) ?
O1 N1 C4 . . 120.62(10) ?
C1 N1 C4 . . 118.97(10) ?
O2 N2 C3 . . 120.63(10) ?
O2 N2 C2 . . 120.72(10) ?
C3 N2 C2 . . 118.65(10) ?
C2 C1 N1 . . 120.92(11) ?
C2 C1 H1 . . 119.5 ?
N1 C1 H1 . . 119.5 ?
N2 C2 C1 . . 120.59(11) ?
N2 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
N2 C3 C4 . . 121.75(11) ?
N2 C3 H3 . . 119.1 ?
C4 C3 H3 . . 119.1 ?
N1 C4 C3 . . 119.11(11) ?
N1 C4 C5 . . 117.75(11) ?
C3 C4 C5 . . 123.14(11) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
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
O1 N1 . 1.2985(13) ?
O2 N2 . 1.3011(13) ?
N1 C1 . 1.3681(16) ?
N1 C4 . 1.3703(15) ?
N2 C3 . 1.3561(16) ?
N2 C2 . 1.3590(15) ?
C1 C2 . 1.3653(17) ?
C1 H1 . 0.9300 ?
C2 H2 . 0.9300 ?
C3 C4 . 1.3789(16) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.4813(18) ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1 O2 1_455 0.93 2.31 3.2224(16) 165.3 y
C2 H2 O2 6_557 0.93 2.23 3.1405(17) 166.5 y
C3 H3 O1 1_655 0.93 2.29 3.2090(15) 168.4 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 498526
