#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/03/2200386.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_2200386
loop_
_publ_author_name
'Hökelek, Tuncer'
'Batı, Hümeyra'
'Bekdemir, Yunus'
'Kütük, Halil'
_publ_section_title
;
 2,3-Dimethylquinoxaline--dimethylglyoxime (1/1)
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o663
_journal_page_last               o665
_journal_paper_doi               10.1107/S1600536801010765
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C10 H10 N2, C4 H8 N2 O2'
_chemical_formula_moiety         'C10 H10 N2, C4 H8 N2 O2'
_chemical_formula_sum            'C14 H18 N4 O2'
_chemical_formula_weight         274.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.779(18)
_cell_angle_beta                 106.668(14)
_cell_angle_gamma                111.018(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9814(10)
_cell_length_b                   8.2719(10)
_cell_length_c                   12.168(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      10
_cell_volume                     710.3(2)
_computing_cell_refinement       MolEN
_computing_data_collection       'MolEN (Fair, 1990)'
_computing_data_reduction        MolEN
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  MolEN
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0000
_diffrn_reflns_av_sigmaI/netI    .0220
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2884
_diffrn_reflns_theta_full        26.29
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .089
_exptl_absorpt_correction_T_max  .982
_exptl_absorpt_correction_T_min  .974
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(Fair, 1990)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod-shaped
_exptl_crystal_F_000             292
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .20
_refine_diff_density_max         .195
_refine_diff_density_min         -.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          .0627
_refine_ls_R_factor_gt           .0458
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0745P)²+0.0913P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1332
_reflns_number_gt                2244
_reflns_number_total             2884
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6055.cif
_cod_data_source_block           I
_cod_database_code               2200386
_cod_database_fobs_code          2200386
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
C1 .41475(19) -.03235(18) .44813(11) .0359(3) Uani d . 1 . . C
C3 .27915(19) .05366(18) -.04196(12) .0337(3) Uani d . 1 . . C
C5 .53352(19) .26909(18) .09310(12) .0343(3) Uani d . 1 . . C
C10 .6008(2) .34364(18) .00366(12) .0347(3) Uani d . 1 . . C
C11 .3451(2) .13324(19) -.13348(12) .0366(3) Uani d . 1 . . C
C14 .5746(2) .51620(19) -.44390(12) .0414(4) Uani d . 1 . . C
N1 .43691(17) .03273(16) .35668(10) .0403(3) Uani d . 1 . . N
N2 .37163(16) .12052(15) .06745(10) .0351(3) Uani d . 1 . . N
N3 .50272(17) .27221(16) -.10997(10) .0384(3) Uani d . 1 . . N
N4 .5232(2) .42225(18) -.36865(11) .0480(3) Uani d . 1 . . N
O1 .27003(15) -.03360(16) .26142(9) .0512(3) Uani d . 1 . . O
O2 .67083(19) .45902(19) -.26459(11) .0635(4) Uani d . 1 . . O
C2 .2332(2) -.1654(2) .45309(14) .0538(5) Uani d . 1 . . C
H2A .1363 -.1868 .3798 .081 Uiso calc PR .50 . . H
H2B .1968 -.1226 .5130 .081 Uiso calc PR .50 . . H
H2C .2498 -.2724 .4696 .081 Uiso calc PR .50 . . H
H2D .2523 -.2011 .5285 .081 Uiso calc PR .50 . . H
H2E .1918 -.2653 .3953 .081 Uiso calc PR .50 . . H
H2F .1388 -.1154 .4387 .081 Uiso calc PR .50 . . H
C4 .1028(2) -.10884(19) -.07081(14) .0443(4) Uani d . 1 . . C
H4A .0866 -.1514 -.0005 .066 Uiso calc R 1 . . H
H4B .1132 -.1967 -.1189 .066 Uiso calc R 1 . . H
H4C -.0044 -.0826 -.1116 .066 Uiso calc R 1 . . H
C6 .6350(2) .3473(2) .20883(13) .0439(4) Uani d . 1 . . C
H6 .5904 .3009 .2683 .053 Uiso calc R 1 . . H
C7 .7989(2) .4915(2) .23377(14) .0503(4) Uani d . 1 . . C
H7 .8660 .5425 .3106 .060 Uiso calc R 1 . . H
C8 .8679(2) .5643(2) .14522(15) .0495(4) Uani d . 1 . . C
H8 .9809 .6618 .1639 .059 Uiso calc R 1 . . H
C9 .7705(2) .4932(2) .03228(14) .0440(4) Uani d . 1 . . C
H9 .8159 .5431 -.0261 .053 Uiso calc R 1 . . H
C12 .2337(2) .0600(2) -.25797(13) .0520(4) Uani d . 1 . . C
H12A .2928 .1336 -.3067 .078 Uiso calc R 1 . . H
H12B .1071 .0554 -.2732 .078 Uiso calc R 1 . . H
H12C .2298 -.0559 -.2739 .078 Uiso calc R 1 . . H
C13 .7696(3) .6519(2) -.42280(16) .0601(5) Uani d . 1 . . C
H13A .8442 .6635 -.3434 .090 Uiso calc PR .50 . . H
H13B .7613 .7623 -.4386 .090 Uiso calc PR .50 . . H
H13C .8280 .6170 -.4729 .090 Uiso calc PR .50 . . H
H13D .7781 .6984 -.4932 .090 Uiso calc PR .50 . . H
H13E .8611 .5995 -.3980 .090 Uiso calc PR .50 . . H
H13F .7943 .7448 -.3637 .090 Uiso calc PR .50 . . H
H1 .303(3) .009(3) .2045(19) .071(6) Uiso d . 1 . . H
H2 .619(3) .397(3) -.224(2) .081(7) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
N1 C1 C1 . 2_656 115.18(15) yes
N1 C1 C2 . . 124.09(13) yes
C1 C1 C2 2_656 . 120.73(15) yes
N2 C3 C11 . . 121.25(12) yes
N2 C3 C4 . . 118.64(12) ?
C11 C3 C4 . . 120.12(13) ?
N2 C5 C6 . . 120.23(12) ?
N2 C5 C10 . . 120.40(13) ?
C6 C5 C10 . . 119.37(13) ?
N3 C10 C9 . . 119.98(13) ?
N3 C10 C5 . . 120.59(13) ?
C9 C10 C5 . . 119.43(13) ?
N3 C11 C3 . . 121.11(13) yes
N3 C11 C12 . . 118.26(13) ?
C3 C11 C12 . . 120.63(13) ?
N4 C14 C14 . 2_664 115.03(17) yes
N4 C14 C13 . . 124.25(15) yes
C14 C14 C13 2_664 . 120.72(16) yes
C1 N1 O1 . . 112.39(12) yes
C3 N2 C5 . . 118.23(11) yes
C11 N3 C10 . . 118.35(12) yes
C14 N4 O2 . . 112.15(13) yes
N1 O1 H1 . . 104.5(14) yes
N4 O2 H2 . . 102.4(16) yes
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C1 C2 H2D . . 109.5 ?
H2A C2 H2D . . 141.1 ?
H2B C2 H2D . . 56.3 ?
H2C C2 H2D . . 56.3 ?
C1 C2 H2E . . 109.5 ?
H2A C2 H2E . . 56.3 ?
H2B C2 H2E . . 141.1 ?
H2C C2 H2E . . 56.3 ?
H2D C2 H2E . . 109.5 ?
C1 C2 H2F . . 109.5 ?
H2A C2 H2F . . 56.3 ?
H2B C2 H2F . . 56.3 ?
H2C C2 H2F . . 141.1 ?
H2D C2 H2F . . 109.5 ?
H2E C2 H2F . . 109.5 ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C7 C6 C5 . . 119.83(14) ?
C7 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
C6 C7 C8 . . 120.96(15) ?
C6 C7 H7 . . 119.5 ?
C8 C7 H7 . . 119.5 ?
C9 C8 C7 . . 120.41(14) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C8 C9 C10 . . 119.99(14) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 H13A . . 109.5 ?
C14 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C14 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C14 C13 H13D . . 109.5 ?
H13A C13 H13D . . 141.1 ?
H13B C13 H13D . . 56.3 ?
H13C C13 H13D . . 56.3 ?
C14 C13 H13E . . 109.5 ?
H13A C13 H13E . . 56.3 ?
H13B C13 H13E . . 141.1 ?
H13C C13 H13E . . 56.3 ?
H13D C13 H13E . . 109.5 ?
C14 C13 H13F . . 109.5 ?
H13A C13 H13F . . 56.3 ?
H13B C13 H13F . . 56.3 ?
H13C C13 H13F . . 141.1 ?
H13D C13 H13F . . 109.5 ?
H13E C13 H13F . . 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
C1 N1 . 1.2811(18) yes
C1 C1 2_656 1.477(3) yes
C1 C2 . 1.491(2) yes
C3 N2 . 1.3119(18) yes
C3 C11 . 1.4434(19) ?
C3 C4 . 1.497(2) ?
C5 N2 . 1.3723(18) yes
C5 C6 . 1.404(2) ?
C5 C10 . 1.4114(19) ?
C10 N3 . 1.3676(19) yes
C10 C9 . 1.410(2) ?
C11 N3 . 1.3123(19) yes
C11 C12 . 1.495(2) ?
C14 N4 . 1.2813(19) yes
C14 C14 2_664 1.473(3) yes
C14 C13 . 1.499(2) yes
N1 O1 . 1.4033(16) yes
N4 O2 . 1.3956(18) yes
O1 H1 . .85(2) yes
O2 H2 . .82(2) yes
C2 H2A . .9600 ?
C2 H2B . .9600 ?
C2 H2C . .9600 ?
C2 H2D . .9600 ?
C2 H2E . .9600 ?
C2 H2F . .9600 ?
C4 H4A . .9600 ?
C4 H4B . .9600 ?
C4 H4C . .9600 ?
C6 C7 . 1.363(2) ?
C6 H6 . .9300 ?
C7 C8 . 1.403(2) ?
C7 H7 . .9300 ?
C8 C9 . 1.359(2) ?
C8 H8 . .9300 ?
C9 H9 . .9300 ?
C12 H12A . .9600 ?
C12 H12B . .9600 ?
C12 H12C . .9600 ?
C13 H13A . .9600 ?
C13 H13B . .9600 ?
C13 H13C . .9600 ?
C13 H13D . .9600 ?
C13 H13E . .9600 ?
C13 H13F . .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
O1 H1 N2 1_546 .8539 2.0451 2.8977 176.30 yes
O2 H2 N3 . .8180 1.9917 2.8053 172.85 yes
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
_geom_torsion_publ_flag
N2 C5 C10 N3 . 2.0(2) yes
C6 C5 C10 N3 . -178.67(13) ?
N2 C5 C10 C9 . -178.06(13) ?
C6 C5 C10 C9 . 1.3(2) ?
N2 C3 C11 N3 . 2.0(2) yes
C4 C3 C11 N3 . -177.63(13) ?
N2 C3 C11 C12 . -177.35(14) ?
C4 C3 C11 C12 . 3.0(2) ?
C1 C1 N1 O1 2_656 -179.87(14) ?
C2 C1 N1 O1 . .8(2) yes
C11 C3 N2 C5 . .1(2) ?
C4 C3 N2 C5 . 179.73(12) ?
C6 C5 N2 C3 . 178.68(13) ?
C10 C5 N2 C3 . -2.0(2) ?
C3 C11 N3 C10 . -2.0(2) ?
C12 C11 N3 C10 . 177.37(13) ?
C9 C10 N3 C11 . -179.87(13) ?
C5 C10 N3 C11 . .1(2) ?
C14 C14 N4 O2 2_664 179.87(16) ?
C13 C14 N4 O2 . -.8(2) yes
N2 C5 C6 C7 . 177.88(14) ?
C10 C5 C6 C7 . -1.5(2) ?
C5 C6 C7 C8 . .4(3) ?
C6 C7 C8 C9 . .9(3) ?
C7 C8 C9 C10 . -1.1(3) ?
N3 C10 C9 C8 . 179.93(14) ?
C5 C10 C9 C8 . .0(2) ?
