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#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/69/2226959.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_2226959
loop_
_publ_author_name
'Li, Jian-Ye'
'Sun, Tao'
'Hao, Ai-You'
'Qiao, Hongwei'
'Xin, Feifei'
_publ_section_title
;
 2-Isopropyl-3-methylquinoxaline 1,4-dioxide
;
_journal_coeditor_code           JH2164
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1906
_journal_paper_doi               10.1107/S1600536810023706
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H14 N2 O2'
_chemical_formula_moiety         'C12 H14 N2 O2'
_chemical_formula_sum            'C12 H14 N2 O2'
_chemical_formula_weight         218.25
_chemical_name_common            '2-isopropyl-3-methylquinoxaline 1,4-dioxide'
_chemical_name_systematic
;
2-Isopropyl-3-methylquinoxaline 1,4-dioxide
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m 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            4
_cell_length_a                   13.3879(10)
_cell_length_b                   6.8462(6)
_cell_length_c                   11.8861(9)
_cell_measurement_reflns_used    4638
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.98
_cell_volume                     1089.44(15)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10376
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         2.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.347
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1446
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0568
_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)+(0.0863P)²+0.4481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.2033
_reflns_number_gt                1062
_reflns_number_total             1446
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jh2164.cif
_cod_data_source_block           I
_cod_database_code               2226959
_cod_database_fobs_code          2226959
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
C C1 0.9509(2) 0.2500 1.1853(3) 0.0603(8) Uani d S 1 . .
H H11 0.9026 0.2500 1.2416 0.072 Uiso calc SR 1 . .
C C2 1.0499(3) 0.2500 1.2128(4) 0.0731(10) Uani d S 1 . .
H H2 1.0689 0.2500 1.2880 0.088 Uiso calc SR 1 . .
C C3 1.1212(2) 0.2500 1.1306(4) 0.0723(11) Uani d S 1 . .
H H3 1.1883 0.2500 1.1510 0.087 Uiso calc SR 1 . .
C C4 1.0962(2) 0.2500 1.0186(4) 0.0641(9) Uani d S 1 . .
H H4 1.1454 0.2500 0.9633 0.077 Uiso calc SR 1 . .
C C5 0.99369(19) 0.2500 0.9893(2) 0.0449(6) Uani d SU 1 . .
C C6 0.92245(18) 0.2500 1.0730(2) 0.0440(6) Uani d S 1 . .
C C7 0.79331(18) 0.2500 0.9352(2) 0.0427(6) Uani d S 1 . .
C C8 0.8664(2) 0.2500 0.8500(2) 0.0481(6) Uani d S 1 . .
C C9 0.8419(3) 0.2500 0.7287(3) 0.0705(9) Uani d S 1 . .
H H9A 0.9023 0.2500 0.6845 0.080 Uiso d S 1 . .
H H9B 0.8034 0.1355 0.7099 0.080 Uiso d . 1 . .
C C10 0.6836(2) 0.2500 0.9063(3) 0.0551(7) Uani d S 1 . .
H H10 0.6798 0.2500 0.8240 0.066 Uiso calc SR 1 . .
C C11 0.63084(17) 0.0655(4) 0.9452(2) 0.0777(8) Uani d . 1 . .
H H11A 0.6657 -0.0468 0.9169 0.117 Uiso calc R 1 . .
H H11B 0.5636 0.0652 0.9173 0.117 Uiso calc R 1 . .
H H11C 0.6299 0.0615 1.0259 0.117 Uiso calc R 1 . .
N N1 0.82094(15) 0.2500 1.04424(19) 0.0445(6) Uani d S 1 . .
N N2 0.96482(17) 0.2500 0.8772(2) 0.0513(6) Uani d SU 1 . .
O O1 0.75580(15) 0.2500 1.12490(18) 0.0681(7) Uani d S 1 . .
O O2 1.03357(18) 0.2500 0.8002(2) 0.0809(8) Uani d S 1 . .
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
C2 C1 C6 . . 119.7(3) ?
C2 C1 H11 . . 120.1 ?
C6 C1 H11 . . 120.1 ?
C1 C2 C3 . . 120.5(3) ?
C1 C2 H2 . . 119.7 ?
C3 C2 H2 . . 119.7 ?
C2 C3 C4 . . 121.5(3) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C3 C4 C5 . . 118.4(3) ?
C3 C4 H4 . . 120.8 ?
C5 C4 H4 . . 120.8 ?
C6 C5 N2 . . 120.0(2) ?
C6 C5 C4 . . 119.6(3) ?
N2 C5 C4 . . 120.4(3) ?
C5 C6 C1 . . 120.3(3) ?
C5 C6 N1 . . 119.7(3) ?
C1 C6 N1 . . 120.0(3) ?
N1 C7 C8 . . 120.0(2) ?
N1 C7 C10 . . 119.1(2) ?
C8 C7 C10 . . 120.9(3) ?
N2 C8 C7 . . 120.2(3) ?
N2 C8 C9 . . 116.6(3) ?
C7 C8 C9 . . 123.1(3) ?
C8 C9 H9A . . 110.2(3) ?
C8 C9 H9B . . 110.1(2) ?
H9A C9 H9B . . 108.8(2) ?
C7 C10 C11 . 7_565 112.56(16) ?
C7 C10 C11 . . 112.56(16) ?
C11 C10 C11 7_565 . 112.5(3) ?
C7 C10 H10 . . 106.2 ?
C11 C10 H10 7_565 . 106.2 ?
C11 C10 H10 . . 106.2 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O1 N1 C7 . . 121.8(2) ?
O1 N1 C6 . . 118.2(2) ?
C7 N1 C6 . . 120.0(2) ?
O2 N2 C8 . . 121.4(3) ?
O2 N2 C5 . . 118.7(2) ?
C8 N2 C5 . . 120.0(2) ?
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 C2 . 1.365(4) ?
C1 C6 . 1.389(4) ?
C1 H11 . 0.9300 ?
C2 C3 . 1.366(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.373(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.416(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.378(4) ?
C5 N2 . 1.387(4) ?
C6 N1 . 1.401(3) ?
C7 N1 . 1.348(3) ?
C7 C8 . 1.409(4) ?
C7 C10 . 1.508(4) ?
C8 N2 . 1.357(4) ?
C8 C9 . 1.479(4) ?
C9 H9A . 0.964(4) ?
C9 H9B . 0.964(2) ?
C10 C11 7_565 1.519(3) ?
C10 C11 . 1.519(3) ?
C10 H10 . 0.9800 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
N1 O1 . 1.296(3) ?
N2 O2 . 1.298(3) ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.000(2) ?
C1 C2 C3 C4 . . . . 0.000(2) ?
C2 C3 C4 C5 . . . . 0.0000(10) ?
C3 C4 C5 C6 . . . . 0.0000(10) ?
C3 C4 C5 N2 . . . . 180.0000(10) ?
N2 C5 C6 C1 . . . . 180.0 ?
C4 C5 C6 C1 . . . . 0.0000(10) ?
N2 C5 C6 N1 . . . . 0.0 ?
C4 C5 C6 N1 . . . . 180.0 ?
C2 C1 C6 C5 . . . . 0.0000(10) ?
C2 C1 C6 N1 . . . . 180.0 ?
N1 C7 C8 N2 . . . . 0.0 ?
C10 C7 C8 N2 . . . . 180.0 ?
N1 C7 C8 C9 . . . . 180.0 ?
C10 C7 C8 C9 . . . . 0.0 ?
N1 C7 C10 C11 . . . 7_565 64.2(2) ?
C8 C7 C10 C11 . . . 7_565 -115.8(2) ?
N1 C7 C10 C11 . . . . -64.2(2) ?
C8 C7 C10 C11 . . . . 115.8(2) ?
C8 C7 N1 O1 . . . . 180.0 ?
C10 C7 N1 O1 . . . . 0.0 ?
C8 C7 N1 C6 . . . . 0.0 ?
C10 C7 N1 C6 . . . . 180.0 ?
C5 C6 N1 O1 . . . . 180.0 ?
C1 C6 N1 O1 . . . . 0.0 ?
C5 C6 N1 C7 . . . . 0.0 ?
C1 C6 N1 C7 . . . . 180.0 ?
C7 C8 N2 O2 . . . . 180.0 ?
C9 C8 N2 O2 . . . . 0.0 ?
C7 C8 N2 C5 . . . . 0.0 ?
C9 C8 N2 C5 . . . . 180.0 ?
C6 C5 N2 O2 . . . . 180.0 ?
C4 C5 N2 O2 . . . . 0.0 ?
C6 C5 N2 C8 . . . . 0.0 ?
C4 C5 N2 C8 . . . . 180.0 ?
