#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/38/2223859.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_2223859
loop_
_publ_author_name
'Zhang, Chang-Hua'
'Tan, Xue-Jie'
'Xing, Dian-Xiang'
_publ_section_title
;
 Methyl pyrazine-2-carboxylate
;
_journal_coeditor_code           IM2150
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2902
_journal_paper_doi               10.1107/S1600536809043451
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H6 N2 O2'
_chemical_formula_moiety         'C6 H6 N2 O2'
_chemical_formula_sum            'C6 H6 N2 O2'
_chemical_formula_weight         138.13
_chemical_name_systematic
;
Methyl pyrazine-2-carboxylate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   3.865(2)
_cell_length_b                   6.690(4)
_cell_length_c                   24.92(2)
_cell_measurement_reflns_used    378
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      1.63
_cell_volume                     644.4(7)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'π and 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  0.0796
_diffrn_reflns_av_sigmaI/netI    0.0654
_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       22
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            3378
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.63
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0698P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1527
_reflns_number_gt                505
_reflns_number_total             757
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2150.cif
_cod_data_source_block           I
_cod_database_code               2223859
_cod_database_fobs_code          2223859
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
C C1 0.2013(5) 0.6623(3) 0.93604(7) 0.0546(6) Uani d . 1 . .
H H1 0.0959 0.7714 0.9524 0.065 Uiso calc R 1 . .
C C2 0.2602(4) 0.6690(2) 0.88246(6) 0.0371(5) Uani d . 1 . .
C C3 0.5035(6) 0.3674(2) 0.88599(7) 0.0561(6) Uani d . 1 . .
H H2 0.6133 0.2594 0.8698 0.067 Uiso calc R 1 . .
C C4 0.4367(6) 0.3607(3) 0.93986(7) 0.0604(6) Uani d . 1 . .
H H3 0.4999 0.2470 0.9589 0.072 Uiso calc R 1 . .
C C5 0.1459(4) 0.8493(2) 0.85163(6) 0.0395(5) Uani d . 1 . .
C C6 0.1405(5) 1.0165(2) 0.76991(8) 0.0642(7) Uani d . 1 . .
H H4 0.2569 1.0139 0.7359 0.096 Uiso calc R 1 . .
H H5 0.1955 1.1385 0.7883 0.096 Uiso calc R 1 . .
H H6 -0.1049 1.0089 0.7643 0.096 Uiso calc R 1 . .
N N1 0.4157(4) 0.52391(19) 0.85628(6) 0.0479(5) Uani d . 1 . .
N N2 0.2869(5) 0.5082(2) 0.96584(6) 0.0665(6) Uani d . 1 . .
O O1 0.2516(3) 0.84861(17) 0.80180(4) 0.0514(4) Uani d . 1 . .
O O2 -0.0298(4) 0.97530(17) 0.87108(5) 0.0690(5) Uani d . 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
C1 0.0681(13) 0.0448(11) 0.0508(10) 0.0017(11) 0.0019(11) 0.0020(10)
C2 0.0335(8) 0.0284(8) 0.0494(10) 0.0006(8) 0.0029(9) 0.0011(8)
C3 0.0621(12) 0.0330(9) 0.0733(12) 0.0112(11) -0.0098(11) 0.0040(10)
C4 0.0677(13) 0.0406(10) 0.0728(12) 0.0014(11) -0.0187(12) 0.0199(10)
C5 0.0409(10) 0.0302(8) 0.0475(10) -0.0001(9) 0.0019(9) 0.0023(9)
C6 0.0719(15) 0.0541(11) 0.0666(13) 0.0086(12) -0.0045(11) 0.0180(11)
N1 0.0535(9) 0.0344(7) 0.0559(9) 0.0089(8) -0.0002(8) -0.0017(8)
N2 0.0891(12) 0.0549(10) 0.0554(10) 0.0024(11) -0.0065(10) 0.0083(9)
O1 0.0664(8) 0.0412(6) 0.0465(7) 0.0105(7) 0.0004(7) 0.0083(6)
O2 0.0935(10) 0.0428(7) 0.0705(9) 0.0264(8) 0.0187(8) -0.0033(7)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 C2 . . 122.76(17) ?
N2 C1 H1 . . 118.6 ?
C2 C1 H1 . . 118.6 ?
N1 C2 C1 . . 122.77(15) ?
N1 C2 C5 . . 118.36(15) ?
C1 C2 C5 . . 118.87(15) ?
N1 C3 C4 . . 121.68(17) ?
N1 C3 H2 . . 119.2 ?
C4 C3 H2 . . 119.2 ?
N2 C4 C3 . . 122.83(17) ?
N2 C4 H3 . . 118.6 ?
C3 C4 H3 . . 118.6 ?
O2 C5 O1 . . 124.72(15) ?
O2 C5 C2 . . 122.14(15) ?
O1 C5 C2 . . 113.11(14) ?
O1 C6 H4 . . 109.5 ?
O1 C6 H5 . . 109.5 ?
H4 C6 H5 . . 109.5 ?
O1 C6 H6 . . 109.5 ?
H4 C6 H6 . . 109.5 ?
H5 C6 H6 . . 109.5 ?
C2 N1 C3 . . 114.99(15) ?
C1 N2 C4 . . 114.94(16) ?
C5 O1 C6 . . 115.33(14) ?
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 N2 . 1.312(2) ?
C1 C2 . 1.355(2) ?
C1 H1 . 0.9300 ?
C2 N1 . 1.315(2) ?
C2 C5 . 1.497(2) ?
C3 N1 . 1.327(2) ?
C3 C4 . 1.368(3) ?
C3 H2 . 0.9300 ?
C4 N2 . 1.315(3) ?
C4 H3 . 0.9300 ?
C5 O2 . 1.186(2) ?
C5 O1 . 1.307(2) ?
C6 O1 . 1.441(2) ?
C6 H4 . 0.9600 ?
C6 H5 . 0.9600 ?
C6 H6 . 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
C3 H2 O2 1_645 0.93 2.35 3.205(3) 152.9
C6 H4 N1 3_656 0.96 2.62 3.582(3) 177.4
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 65523
