##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_journal_date_recd_electronic     2017-06-28
_journal_date_accepted     2017-07-05
_journal_name_full     'IUCrData'
_journal_year     2017
_journal_volume     2
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S241431461700997X
_journal_coeditor_code     SJ4126
_publ_contact_author_name     'D. Paul Rillema'
_publ_contact_author_address
;
Department of Chemistry
Wichita State University
Wichita, KS 67260,
USA
;
_publ_contact_author_email     'paul.rillema@wichita.edu'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '316-978-3732'
_publ_section_title
;
Methyl 5-methylpyrazine-2-carboxylate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Rillema, D. Paul' .
;
Department of Chemistry
Wichita State University
Wichita, KS 67260,
USA
;
    'KomReddy, Venugopal' .
;
Department of Chemistry
Wichita State University
Wichita, KS 67260,
USA
;
    'Senaratne, Nilmini K.' .
;
Department of Chemistry
Wichita State University
Wichita, KS 67260
USA
;
    'Eichhorn, David M.' .
;
Department of Chemistry
Wichita State University
Wichita, KS 67260,
USA
;
_publ_section_synopsis
;
The molecular and crystal structure of the title pyrazinecarboxylate derivative
is reported. C---H...N and C---H...O hydrogen bonding is the key component in
the crystal packing.
;
_chemical_name_systematic
;
Methyl 5-methylpyrazine-2-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C7 H8 N2 O2'
_chemical_formula_sum     'C7 H8 N2 O2'
_chemical_formula_iupac     'C7 H8 N2 O2'
_chemical_formula_weight     152.15
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     3.88720(10)
_cell_length_b     6.8386(3)
_cell_length_c     13.6279(5)
_cell_angle_alpha     90
_cell_angle_beta     93.303(2)
_cell_angle_gamma     90
_cell_volume     361.67(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     7189
_cell_measurement_theta_min     2.99
_cell_measurement_theta_max     26.97
_cell_measurement_temperature     150
_exptl_crystal_description     block
_exptl_crystal_colour     'clear colourless'
_exptl_crystal_size_max     0.657
_exptl_crystal_size_mid     0.652
_exptl_crystal_size_min     0.562
_exptl_crystal_density_diffrn     1.397
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     160
_exptl_absorpt_coefficient_mu     0.105
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.9248
_exptl_absorpt_correction_T_max     0.9755
_exptl_special_details     ?
_diffrn_ambient_temperature     150
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_device     'three-circle diffractometer'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     5.6
_diffrn_reflns_number     9931
_diffrn_reflns_av_R_equivalents     0.0149
_diffrn_reflns_theta_min     3.334
_diffrn_reflns_theta_max     27.119
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -4
_diffrn_reflns_limit_h_max     4
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     1556
_reflns_number_gt     1495
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0303
_refine_ls_R_factor_gt     0.0290
_refine_ls_wR_factor_gt     0.0817
_refine_ls_wR_factor_ref     0.0827
_refine_ls_goodness_of_fit_ref     1.137
_refine_ls_restrained_S_all     1.136
_refine_ls_number_reflns     1556
_refine_ls_number_parameters     102
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0504P)²+0.0328P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.195
_refine_diff_density_min     -0.173
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x
determined using 659 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al, 2013)
;
_refine_ls_abs_structure_Flack     0.0(2)
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'
_computing_data_collection
;
SMART (Bruker, 2012)
;
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O2 0.2766(3) 0.74768(19) 0.59049(8) 0.0235(3) Uani d 1 . .
    O O1 0.5934(4) 0.8742(2) 0.71764(10) 0.0338(4) Uani d 1 . .
    N N2 0.3528(4) 0.4025(2) 0.89293(10) 0.0223(3) Uani d 1 . .
    N N1 0.1414(4) 0.4246(2) 0.69310(10) 0.0211(3) Uani d 1 . .
    C C6 0.4125(4) 0.7469(3) 0.68198(12) 0.0204(4) Uani d 1 . .
    C C4 0.3192(4) 0.5692(2) 0.73882(12) 0.0182(4) Uani d 1 . .
    C C3 0.0722(4) 0.2702(3) 0.74819(12) 0.0216(4) Uani d 1 . .
    H H3 -0.0525 0.1642 0.7184 0.026 Uiso calc 1 . .
    C C2 0.1754(4) 0.2572(2) 0.84819(12) 0.0194(4) Uani d 1 . .
    C C1 0.0880(5) 0.0836(3) 0.90848(13) 0.0267(4) Uani d 1 . .
    H H1A 0.2996 0.0283 0.9397 0.040 Uiso calc 1 . .
    H H1B -0.0271 -0.0151 0.8660 0.040 Uiso calc 1 . .
    H H1C -0.0660 0.1238 0.9593 0.040 Uiso calc 1 . .
    C C5 0.4222(5) 0.5576(3) 0.83769(12) 0.0222(4) Uani d 1 . .
    H H5 0.5466 0.6639 0.8673 0.027 Uiso calc 1 . .
    C C7 0.3671(5) 0.9159(3) 0.53238(13) 0.0288(4) Uani d 1 . .
    H H7A 0.2383 0.9115 0.4685 0.043 Uiso calc 1 . .
    H H7B 0.6148 0.9136 0.5225 0.043 Uiso calc 1 . .
    H H7C 0.3093 1.0361 0.5669 0.043 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    O2 C6 . 1.3259(19) ?
    O2 C7 . 1.451(2) ?
    O1 C6 . 1.203(2) ?
    N2 C2 . 1.337(2) ?
    N2 C5 . 1.337(2) ?
    N1 C4 . 1.339(2) ?
    N1 C3 . 1.332(2) ?
    C6 C4 . 1.497(2) ?
    C4 C5 . 1.386(2) ?
    C3 H3 . 0.9500 ?
    C3 C2 . 1.401(2) ?
    C2 C1 . 1.494(2) ?
    C1 H1A . 0.9800 ?
    C1 H1B . 0.9800 ?
    C1 H1C . 0.9800 ?
    C5 H5 . 0.9500 ?
    C7 H7A . 0.9800 ?
    C7 H7B . 0.9800 ?
    C7 H7C . 0.9800 ?
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
    C6 O2 C7 . . 114.85(14) ?
    C2 N2 C5 . . 116.65(14) ?
    C3 N1 C4 . . 116.01(13) ?
    O2 C6 C4 . . 113.23(14) ?
    O1 C6 O2 . . 124.67(16) ?
    O1 C6 C4 . . 122.10(15) ?
    N1 C4 C6 . . 119.51(14) ?
    N1 C4 C5 . . 121.52(15) ?
    C5 C4 C6 . . 118.97(14) ?
    N1 C3 H3 . . 118.6 ?
    N1 C3 C2 . . 122.86(15) ?
    C2 C3 H3 . . 118.6 ?
    N2 C2 C3 . . 120.52(15) ?
    N2 C2 C1 . . 117.89(14) ?
    C3 C2 C1 . . 121.59(15) ?
    C2 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    N2 C5 C4 . . 122.43(16) ?
    N2 C5 H5 . . 118.8 ?
    C4 C5 H5 . . 118.8 ?
    O2 C7 H7A . . 109.5 ?
    O2 C7 H7B . . 109.5 ?
    O2 C7 H7C . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
loop_
    _geom_hbond_atom_site_label_d
    _geom_hbond_atom_site_label_h
    _geom_hbond_atom_site_label_a
    _geom_hbond_site_symmetry_d
    _geom_hbond_site_symmetry_h
    _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 H1A N2 2_555 2_555 2_555 0.980 2.723 3.592 148.13 yes
    C1 H1B O1 2_555 2_555 2_555 0.980 2.548 3.455 153.73 yes
    C3 H3 O1 2_555 2_555 2_555 0.950 2.414 3.299 154.90 yes
_shelxl_version_number         .2013
