#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/55/2235514.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_2235514
loop_
_publ_author_name
'Li, Chuan-Hui'
'Wu, Wen-Shi'
'Huang, Yu-Min'
_publ_section_title
;
 Diethyl pyrazine-2,5-dicarboxylate
;
_journal_coeditor_code           IS5143
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2236
_journal_paper_doi               10.1107/S1600536812028164
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H12 N2 O4'
_chemical_formula_moiety         'C10 H12 N2 O4'
_chemical_formula_sum            'C10 H12 N2 O4'
_chemical_formula_weight         224.22
_chemical_name_systematic
;
Diethyl pyrazine-2,5-dicarboxylate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.713(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.284(6)
_cell_length_b                   5.640(3)
_cell_length_c                   7.881(4)
_cell_measurement_reflns_used    2994
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.50
_cell_measurement_theta_min      4.02
_cell_volume                     517.1(5)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       'ω 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    0.0358
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2994
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         4.02
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick,1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             236.0
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.313
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0525
_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)+(0.0606P)²+0.1472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                1055
_reflns_number_total             1317
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL a in P2(1)/c
CELL 0.71073  12.2837   5.6397   7.8806  90.000  108.713  90.000
ZERR   10.00   0.0061   0.0029   0.0039   0.000   0.0089   0.000
LATT  1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H N O
UNIT 10 12 2 4
htab
L.S. 10
BOND $h
FMAP 2
PLAN 20
conf
eqiv $1 x,-0.5-y,0.5+z
rtab H4A O2_$1
rtab ahd C4 H4A O2_$1
htab
htab C4 O2_$1
acta
WGHT    0.060000    0.146400
FVAR       0.23822
WGHT      0.0606      0.1472
N1    3    0.469621   -0.231456    0.526518    11.00000    0.03129    0.01737 =
         0.03692    0.00017    0.01534   -0.00007
O1    4    0.260069    0.092082    0.644250    11.00000    0.02890    0.02342 =
         0.04566    0.00063    0.01985    0.00123
O2    4    0.280727   -0.300510    0.631278    11.00000    0.04500    0.02339 =
         0.06176   -0.00047    0.03070   -0.00617
C1    1    0.412079   -0.045050    0.555124    11.00000    0.02562    0.02105 =
         0.02555   -0.00049    0.00796   -0.00093
C2    1    0.441750    0.186043    0.528921    11.00000    0.03049    0.01836 =
         0.03280    0.00000    0.01328    0.00141
AFIX  43
H2A   2    0.398631    0.311003    0.550686    11.00000   -1.20000
AFIX   0
C3    1    0.311618   -0.103015    0.614644    11.00000    0.02845    0.02123 =
         0.03044    0.00070    0.01038   -0.00099
C4    1    0.161064    0.056774    0.701775    11.00000    0.03305    0.03379 =
         0.04920    0.00491    0.02479    0.00008
AFIX  23
H4A   2    0.184800    0.001013    0.824684    11.00000    -1.2
H4B   2    0.110218   -0.060495    0.626627    11.00000   -1.20000
AFIX   0
C5    1    0.100963    0.288328    0.687125    11.00000    0.03304    0.04108 =
         0.04467    0.00188    0.02069    0.00462
AFIX  33
H5A   2    0.072505    0.335654    0.563684    11.00000   -1.5
H5B   2    0.153693    0.405776    0.754901    11.00000   -1.5
H5C   2    0.037871    0.273116    0.733329    11.00000   -1.5
HKLF 4
REM  a in P2(1)/c
REM R1 =  0.0523 for   1055 Fo > 4sig(Fo)  and  0.0602 for all   1223 data
REM     75 parameters refined using      0 restraints
END
;
_cod_data_source_file            is5143.cif
_cod_data_source_block           I
_cod_original_cell_volume        517.2(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235514
_cod_database_fobs_code          2235514
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_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_symmetry_multiplicity
N N1 0.46961(11) -0.2315(2) 0.52651(18) 0.0275(3) Uani d . 1 1
O O1 0.26007(9) 0.0921(2) 0.64425(16) 0.0308(3) Uani d . 1 1
O O2 0.28072(11) -0.3005(2) 0.63126(19) 0.0401(4) Uani d . 1 1
C C1 0.41208(12) -0.0450(3) 0.55512(19) 0.0241(3) Uani d . 1 1
C C2 0.44174(13) 0.1860(3) 0.5289(2) 0.0265(4) Uani d . 1 1
H H2A 0.3986 0.3110 0.5507 0.032 Uiso calc R 1 1
C C3 0.31162(13) -0.1030(3) 0.6147(2) 0.0265(4) Uani d . 1 1
C C4 0.16106(15) 0.0568(3) 0.7018(3) 0.0359(4) Uani d . 1 1
H H4A 0.1848 0.0010 0.8247 0.043 Uiso calc R 1 1
H H4B 0.1102 -0.0605 0.6266 0.043 Uiso calc R 1 1
C C5 0.10095(15) 0.2883(3) 0.6871(2) 0.0377(4) Uani d . 1 1
H H5A 0.0725 0.3356 0.5636 0.057 Uiso calc R 1 1
H H5B 0.1537 0.4058 0.7549 0.057 Uiso calc R 1 1
H H5C 0.0378 0.2732 0.7333 0.057 Uiso calc R 1 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
N1 0.0314(7) 0.0174(6) 0.0369(7) -0.0001(5) 0.0154(6) 0.0002(5)
O1 0.0289(6) 0.0234(6) 0.0457(7) 0.0012(4) 0.0199(5) 0.0006(5)
O2 0.0450(8) 0.0234(7) 0.0617(9) -0.0062(5) 0.0307(6) -0.0005(6)
C1 0.0256(7) 0.0211(8) 0.0256(7) -0.0009(6) 0.0080(6) -0.0005(6)
C2 0.0304(8) 0.0184(7) 0.0328(8) 0.0014(6) 0.0132(6) 0.0000(6)
C3 0.0284(8) 0.0212(8) 0.0304(8) -0.0010(6) 0.0104(6) 0.0007(6)
C4 0.0330(9) 0.0337(9) 0.0493(10) 0.0000(7) 0.0247(8) 0.0048(8)
C5 0.0330(9) 0.0410(11) 0.0450(10) 0.0046(7) 0.0208(8) 0.0018(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_site_symmetry_1
_geom_angle
C2 N1 C1 3_656 116.31(14)
C3 O1 C4 . 116.04(13)
N1 C1 C2 . 122.69(14)
N1 C1 C3 . 114.83(14)
C2 C1 C3 . 122.47(14)
N1 C2 C1 3_656 121.00(15)
N1 C2 H2A 3_656 119.5
C1 C2 H2A . 119.5
O2 C3 O1 . 124.49(15)
O2 C3 C1 . 124.19(15)
O1 C3 C1 . 111.31(13)
O1 C4 C5 . 107.59(14)
O1 C4 H4A . 110.2
C5 C4 H4A . 110.2
O1 C4 H4B . 110.2
C5 C4 H4B . 110.2
H4A C4 H4B . 108.5
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
N1 C2 3_656 1.322(2)
N1 C1 . 1.326(2)
O1 C3 . 1.3270(19)
O1 C4 . 1.442(2)
O2 C3 . 1.197(2)
C1 C2 . 1.386(2)
C1 C3 . 1.490(2)
C2 H2A . 0.9300
C4 C5 . 1.486(3)
C4 H4A . 0.9700
C4 H4B . 0.9700
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
C4 H4A O2 4_556 0.97 2.58 3.537(3) 168
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C2 N1 C1 C2 3_656 . 0.1(3)
C2 N1 C1 C3 3_656 . 179.07(13)
N1 C1 C2 N1 . 3_656 -0.1(3)
C3 C1 C2 N1 . 3_656 -178.99(14)
C4 O1 C3 O2 . . 0.6(2)
C4 O1 C3 C1 . . 179.71(13)
N1 C1 C3 O2 . . -2.3(2)
C2 C1 C3 O2 . . 176.70(16)
N1 C1 C3 O1 . . 178.63(13)
C2 C1 C3 O1 . . -2.4(2)
C3 O1 C4 C5 . . -167.24(14)
