#------------------------------------------------------------------------------
#$Date: 2021-01-09 07:21:54 +0100 (Sat 09 de Jan de 2021) $
#$Revision: 260888 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/00/1560014.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_1560014
loop_
_publ_author_name
'Chen, Lin'
'Hu, Jin'
'Sun, Hong-Shun'
_publ_section_title
;
 7,8-Dimethyl-11H-indeno[1,2-b]quinoxalin-11-one
;
_journal_coeditor_code           XU4042
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x210018
_journal_paper_doi               10.1107/S2414314621000183
_journal_volume                  6
_journal_year                    2021
_chemical_formula_iupac          'C17 H12 N2 O'
_chemical_formula_moiety         'C17 H12 N2 O'
_chemical_formula_sum            'C17 H12 N2 O'
_chemical_formula_weight         260.29
_chemical_name_systematic
;
7,8-Dimethyl-11H-indeno[1,2-b]quinoxalin-11-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.866(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4548(9)
_cell_length_b                   22.976(3)
_cell_length_c                   8.3149(10)
_cell_measurement_reflns_used    5967
_cell_measurement_temperature    282
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.66
_cell_volume                     1281.5(3)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
SMART (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
ShelXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      282.34
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10114
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_min         3.069
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0487P)²+0.7679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1532
_reflns_number_gt                2437
_reflns_number_total             3134
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            xu4042sup1.cif
_cod_data_source_block           I
_cod_database_code               1560014
_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.
;
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.1899(2) 0.67104(6) 0.38760(19) 0.0613(4) Uani d 1 . .
N N1 0.1135(2) 0.54175(6) 0.3195(2) 0.0400(4) Uani d 1 . .
N N2 0.3665(2) 0.48258(6) 0.6458(2) 0.0417(4) Uani d 1 . .
C C1 0.3614(2) 0.53906(7) 0.6270(2) 0.0348(4) Uani d 1 . .
C C2 0.4780(2) 0.58312(7) 0.7599(2) 0.0366(4) Uani d 1 . .
C C3 0.6183(3) 0.57743(9) 0.9349(3) 0.0483(5) Uani d 1 . .
H H3 0.6505 0.5411 0.9892 0.058 Uiso calc 1 . .
C C4 0.7104(3) 0.62748(10) 1.0279(3) 0.0542(5) Uani d 1 . .
H H4 0.8068 0.6244 1.1455 0.065 Uiso calc 1 . .
C C5 0.6616(3) 0.68157(9) 0.9493(3) 0.0517(5) Uani d 1 . .
H H5 0.7257 0.7144 1.0146 0.062 Uiso calc 1 . .
C C6 0.5187(3) 0.68793(8) 0.7744(3) 0.0463(5) Uani d 1 . .
H H6 0.4851 0.7245 0.7217 0.056 Uiso calc 1 . .
C C7 0.4275(3) 0.63822(8) 0.6807(2) 0.0381(4) Uani d 1 . .
C C8 0.2716(3) 0.63268(7) 0.4928(2) 0.0400(4) Uani d 1 . .
C C9 0.2358(2) 0.56799(7) 0.4648(2) 0.0362(4) Uani d 1 . .
C C10 0.1132(3) 0.48201(7) 0.3342(2) 0.0381(4) Uani d 1 . .
C C11 -0.0140(3) 0.44895(8) 0.1861(3) 0.0448(4) Uani d 1 . .
H H11 -0.0943 0.4680 0.0802 0.054 Uiso calc 1 . .
C C12 -0.0229(3) 0.38935(8) 0.1933(3) 0.0490(5) Uani d 1 . .
C C13 0.1007(3) 0.36040(8) 0.3545(3) 0.0528(5) Uani d 1 . .
C C14 0.2283(3) 0.39190(8) 0.4996(3) 0.0500(5) Uani d 1 . .
H H14 0.3106 0.3723 0.6037 0.060 Uiso calc 1 . .
C C15 0.2382(3) 0.45313(7) 0.4951(2) 0.0389(4) Uani d 1 . .
C C16 0.0931(4) 0.29501(9) 0.3674(4) 0.0773(8) Uani d 1 . .
H H16A 0.1901 0.2825 0.4830 0.116 Uiso calc 1 . .
H H16B 0.1219 0.2775 0.2765 0.116 Uiso calc 1 . .
H H16C -0.0375 0.2834 0.3511 0.116 Uiso calc 1 . .
C C17 -0.1623(4) 0.35635(10) 0.0302(4) 0.0665(7) Uani d 1 . .
H H17A -0.2286 0.3831 -0.0665 0.100 Uiso calc 1 . .
H H17B -0.2595 0.3362 0.0560 0.100 Uiso calc 1 . .
H H17C -0.0878 0.3287 -0.0030 0.100 Uiso calc 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
C9 N1 C10 . . 114.01(15) ?
C1 N2 C15 . . 114.02(15) ?
N2 C1 C2 . . 128.14(16) ?
N2 C1 C9 . . 123.29(16) ?
C9 C1 C2 . . 108.57(14) ?
C3 C2 C1 . . 130.93(17) ?
C3 C2 C7 . . 120.44(17) ?
C7 C2 C1 . . 108.62(15) ?
C2 C3 H3 . . 120.9 ?
C2 C3 C4 . . 118.18(19) ?
C4 C3 H3 . . 120.9 ?
C3 C4 H4 . . 119.4 ?
C5 C4 C3 . . 121.26(19) ?
C5 C4 H4 . . 119.4 ?
C4 C5 H5 . . 119.5 ?
C4 C5 C6 . . 121.09(19) ?
C6 C5 H5 . . 119.5 ?
C5 C6 H6 . . 121.0 ?
C7 C6 C5 . . 117.92(18) ?
C7 C6 H6 . . 121.0 ?
C2 C7 C8 . . 110.02(15) ?
C6 C7 C2 . . 121.10(17) ?
C6 C7 C8 . . 128.89(17) ?
O1 C8 C7 . . 127.95(16) ?
O1 C8 C9 . . 127.57(17) ?
C7 C8 C9 . . 104.47(14) ?
N1 C9 C1 . . 124.53(15) ?
N1 C9 C8 . . 127.17(15) ?
C1 C9 C8 . . 108.30(14) ?
N1 C10 C11 . . 119.18(16) ?
N1 C10 C15 . . 121.59(16) ?
C11 C10 C15 . . 119.23(16) ?
C10 C11 H11 . . 119.1 ?
C12 C11 C10 . . 121.88(19) ?
C12 C11 H11 . . 119.1 ?
C11 C12 C13 . . 118.99(18) ?
C11 C12 C17 . . 119.4(2) ?
C13 C12 C17 . . 121.62(19) ?
C12 C13 C16 . . 120.3(2) ?
C14 C13 C12 . . 119.94(17) ?
C14 C13 C16 . . 119.7(2) ?
C13 C14 H14 . . 119.1 ?
C13 C14 C15 . . 121.82(19) ?
C15 C14 H14 . . 119.1 ?
N2 C15 C10 . . 122.55(15) ?
N2 C15 C14 . . 119.32(17) ?
C14 C15 C10 . . 118.13(17) ?
C13 C16 H16A . . 109.5 ?
C13 C16 H16B . . 109.5 ?
C13 C16 H16C . . 109.5 ?
H16A C16 H16B . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C12 C17 H17A . . 109.5 ?
C12 C17 H17B . . 109.5 ?
C12 C17 H17C . . 109.5 ?
H17A C17 H17B . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 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
O1 C8 . 1.203(2) ?
N1 C9 . 1.301(2) ?
N1 C10 . 1.378(2) ?
N2 C1 . 1.306(2) ?
N2 C15 . 1.377(2) ?
C1 C2 . 1.471(2) ?
C1 C9 . 1.427(2) ?
C2 C3 . 1.378(3) ?
C2 C7 . 1.401(2) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.389(3) ?
C4 H4 . 0.9300 ?
C4 C5 . 1.377(3) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.385(3) ?
C6 H6 . 0.9300 ?
C6 C7 . 1.382(2) ?
C7 C8 . 1.491(2) ?
C8 C9 . 1.510(2) ?
C10 C11 . 1.405(2) ?
C10 C15 . 1.418(3) ?
C11 H11 . 0.9300 ?
C11 C12 . 1.374(3) ?
C12 C13 . 1.418(3) ?
C12 C17 . 1.505(3) ?
C13 C14 . 1.372(3) ?
C13 C16 . 1.509(3) ?
C14 H14 . 0.9300 ?
C14 C15 . 1.410(2) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
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
O1 C8 C9 N1 . . . . 2.1(3) ?
O1 C8 C9 C1 . . . . -178.2(2) ?
N1 C10 C11 C12 . . . . -179.08(17) ?
N1 C10 C15 N2 . . . . 0.1(3) ?
N1 C10 C15 C14 . . . . 179.67(16) ?
N2 C1 C2 C3 . . . . -0.6(3) ?
N2 C1 C2 C7 . . . . 178.74(17) ?
N2 C1 C9 N1 . . . . 0.2(3) ?
N2 C1 C9 C8 . . . . -179.51(16) ?
C1 N2 C15 C10 . . . . 0.3(2) ?
C1 N2 C15 C14 . . . . -179.21(16) ?
C1 C2 C3 C4 . . . . 177.84(18) ?
C1 C2 C7 C6 . . . . -178.38(16) ?
C1 C2 C7 C8 . . . . 1.22(19) ?
C2 C1 C9 N1 . . . . 179.72(16) ?
C2 C1 C9 C8 . . . . 0.04(18) ?
C2 C3 C4 C5 . . . . 0.9(3) ?
C2 C7 C8 O1 . . . . 177.7(2) ?
C2 C7 C8 C9 . . . . -1.16(19) ?
C3 C2 C7 C6 . . . . 1.0(3) ?
C3 C2 C7 C8 . . . . -179.36(16) ?
C3 C4 C5 C6 . . . . 0.0(3) ?
C4 C5 C6 C7 . . . . -0.5(3) ?
C5 C6 C7 C2 . . . . -0.1(3) ?
C5 C6 C7 C8 . . . . -179.59(18) ?
C6 C7 C8 O1 . . . . -2.7(3) ?
C6 C7 C8 C9 . . . . 178.41(18) ?
C7 C2 C3 C4 . . . . -1.4(3) ?
C7 C8 C9 N1 . . . . -179.01(17) ?
C7 C8 C9 C1 . . . . 0.66(18) ?
C9 N1 C10 C11 . . . . 179.60(16) ?
C9 N1 C10 C15 . . . . -0.4(2) ?
C9 C1 C2 C3 . . . . 179.88(18) ?
C9 C1 C2 C7 . . . . -0.79(19) ?
C10 N1 C9 C1 . . . . 0.3(2) ?
C10 N1 C9 C8 . . . . 179.93(16) ?
C10 C11 C12 C13 . . . . -0.4(3) ?
C10 C11 C12 C17 . . . . 179.93(17) ?
C11 C10 C15 N2 . . . . -179.92(16) ?
C11 C10 C15 C14 . . . . -0.4(2) ?
C11 C12 C13 C14 . . . . -0.7(3) ?
C11 C12 C13 C16 . . . . 179.44(19) ?
C12 C13 C14 C15 . . . . 1.3(3) ?
C13 C14 C15 N2 . . . . 178.80(17) ?
C13 C14 C15 C10 . . . . -0.8(3) ?
C15 N2 C1 C2 . . . . -179.95(15) ?
C15 N2 C1 C9 . . . . -0.5(2) ?
C15 C10 C11 C12 . . . . 1.0(3) ?
C16 C13 C14 C15 . . . . -178.83(19) ?
C17 C12 C13 C14 . . . . 178.92(18) ?
C17 C12 C13 C16 . . . . -0.9(3) ?

_cod_database_fobs_code 1560014
