#------------------------------------------------------------------------------
#$Date: 2020-09-09 08:10:40 +0300 (Wed, 09 Sep 2020) $
#$Revision: 256248 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/90/1559022.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_1559022
loop_
_publ_author_name
'Chen, Lin'
'Hu, Jin'
'Wu, Li-Li'
'Sun, Hong-Shun'
_publ_section_title
;
 11,11-Diphenyl-11H-indeno[1,2-b]quinoxaline
;
_journal_coeditor_code           HB4357
_journal_issue                   9
_journal_name_full               IUCrData
_journal_page_first              x201213
_journal_paper_doi               10.1107/S2414314620012134
_journal_volume                  5
_journal_year                    2020
_chemical_formula_iupac          'C27 H18 N2'
_chemical_formula_moiety         'C27 H18 N2'
_chemical_formula_sum            'C27 H18 N2'
_chemical_formula_weight         370.43
_chemical_name_systematic
;
11,11-Diphenyl-11H-indeno[1,2-b]quinoxaline
;
_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     dual
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.606(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.642(5)
_cell_length_b                   11.407(5)
_cell_length_c                   17.858(8)
_cell_measurement_reflns_used    3937
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.357
_cell_measurement_theta_min      2.347
_cell_volume                     1909.0(16)
_computing_cell_refinement
;
SAINT  (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_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      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11621
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.633
_diffrn_reflns_theta_min         2.347
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.999996
_exptl_absorpt_correction_T_min  0.858773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.202
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0427
_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)+(0.0447P)²+0.3316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                3277
_reflns_number_total             4429
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4357sup1.cif
_cod_data_source_block           I
_cod_database_code               1559022
_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
N N1 0.51226(11) 0.55738(9) 0.65772(6) 0.0394(3) Uani d 1 . .
N N2 0.23762(11) 0.47436(9) 0.57474(6) 0.0395(3) Uani d 1 . .
C C1 0.5462(2) 1.01277(15) 0.63861(11) 0.0695(5) Uani d 1 . .
H H1 0.5840 1.0786 0.6200 0.083 Uiso calc 1 . .
C C2 0.4016(2) 0.99914(15) 0.62609(11) 0.0716(5) Uani d 1 . .
H H2 0.3410 1.0565 0.5995 0.086 Uiso calc 1 . .
C C3 0.34490(17) 0.90057(13) 0.65275(9) 0.0541(4) Uani d 1 . .
H H3 0.2464 0.8923 0.6439 0.065 Uiso calc 1 . .
C C4 0.43262(13) 0.81433(11) 0.69233(7) 0.0375(3) Uani d 1 . .
C C5 0.57958(15) 0.83006(12) 0.70533(9) 0.0495(3) Uani d 1 . .
H H5 0.6409 0.7734 0.7322 0.059 Uiso calc 1 . .
C C6 0.63502(18) 0.92863(14) 0.67879(11) 0.0631(4) Uani d 1 . .
H H6 0.7334 0.9382 0.6882 0.076 Uiso calc 1 . .
C C7 0.37522(12) 0.70131(11) 0.72101(7) 0.0350(3) Uani d 1 . .
C C8 0.44723(13) 0.67853(11) 0.80551(7) 0.0382(3) Uani d 1 . .
C C9 0.45826(15) 0.76998(14) 0.85801(8) 0.0495(3) Uani d 1 . .
H H9 0.4275 0.8445 0.8405 0.059 Uiso calc 1 . .
C C10 0.51424(17) 0.75184(17) 0.93576(9) 0.0620(4) Uani d 1 . .
H H10 0.5191 0.8135 0.9704 0.074 Uiso calc 1 . .
C C11 0.56268(18) 0.64278(19) 0.96174(10) 0.0707(5) Uani d 1 . .
H H11 0.6005 0.6304 1.0140 0.085 Uiso calc 1 . .
C C12 0.55541(18) 0.55199(17) 0.91067(10) 0.0667(5) Uani d 1 . .
H H12 0.5904 0.4786 0.9284 0.080 Uiso calc 1 . .
C C13 0.49617(15) 0.56892(13) 0.83284(9) 0.0504(4) Uani d 1 . .
H H13 0.4893 0.5063 0.7988 0.060 Uiso calc 1 . .
C C14 0.21179(13) 0.70151(11) 0.70965(7) 0.0363(3) Uani d 1 . .
C C15 0.12920(14) 0.76476(12) 0.74945(8) 0.0450(3) Uani d 1 . .
H H15 0.1717 0.8172 0.7879 0.054 Uiso calc 1 . .
C C16 -0.01721(15) 0.74878(13) 0.73120(9) 0.0486(3) Uani d 1 . .
H H16 -0.0727 0.7907 0.7580 0.058 Uiso calc 1 . .
C C17 -0.08276(14) 0.67165(13) 0.67389(9) 0.0486(3) Uani d 1 . .
H H17 -0.1814 0.6630 0.6622 0.058 Uiso calc 1 . .
C C18 -0.00211(14) 0.60742(12) 0.63394(8) 0.0434(3) Uani d 1 . .
H H18 -0.0454 0.5555 0.5953 0.052 Uiso calc 1 . .
C C19 0.14523(13) 0.62214(11) 0.65281(7) 0.0358(3) Uani d 1 . .
C C20 0.25545(13) 0.55958(10) 0.62526(7) 0.0345(3) Uani d 1 . .
C C21 0.39212(13) 0.60103(10) 0.66650(7) 0.0345(3) Uani d 1 . .
C C22 0.49792(14) 0.46536(11) 0.60637(7) 0.0382(3) Uani d 1 . .
C C23 0.36232(14) 0.42444(11) 0.56559(7) 0.0378(3) Uani d 1 . .
C C24 0.35458(17) 0.32749(12) 0.51582(8) 0.0483(3) Uani d 1 . .
H H24 0.2661 0.2993 0.4894 0.058 Uiso calc 1 . .
C C25 0.47617(18) 0.27492(13) 0.50633(9) 0.0547(4) Uani d 1 . .
H H25 0.4701 0.2115 0.4730 0.066 Uiso calc 1 . .
C C26 0.61001(17) 0.31559(13) 0.54628(9) 0.0547(4) Uani d 1 . .
H H26 0.6921 0.2787 0.5394 0.066 Uiso calc 1 . .
C C27 0.62156(15) 0.40861(12) 0.59517(9) 0.0481(3) Uani d 1 . .
H H27 0.7112 0.4348 0.6213 0.058 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'
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
C21 N1 C22 . . 114.68(11) ?
C20 N2 C23 . . 114.37(11) ?
C2 C1 H1 . . 120.2 ?
C2 C1 C6 . . 119.53(15) ?
C6 C1 H1 . . 120.2 ?
C1 C2 H2 . . 119.8 ?
C1 C2 C3 . . 120.42(16) ?
C3 C2 H2 . . 119.8 ?
C2 C3 H3 . . 119.6 ?
C4 C3 C2 . . 120.81(15) ?
C4 C3 H3 . . 119.6 ?
C3 C4 C5 . . 118.09(13) ?
C3 C4 C7 . . 122.92(12) ?
C5 C4 C7 . . 118.97(11) ?
C4 C5 H5 . . 119.7 ?
C6 C5 C4 . . 120.69(14) ?
C6 C5 H5 . . 119.7 ?
C1 C6 C5 . . 120.45(16) ?
C1 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C4 C7 C14 . . 113.08(10) ?
C8 C7 C4 . . 110.86(10) ?
C8 C7 C14 . . 110.09(10) ?
C8 C7 C21 . . 114.09(10) ?
C21 C7 C4 . . 108.26(10) ?
C21 C7 C14 . . 100.11(9) ?
C9 C8 C7 . . 118.92(12) ?
C13 C8 C7 . . 122.69(12) ?
C13 C8 C9 . . 118.32(13) ?
C8 C9 H9 . . 119.5 ?
C10 C9 C8 . . 121.01(15) ?
C10 C9 H9 . . 119.5 ?
C9 C10 H10 . . 120.1 ?
C11 C10 C9 . . 119.83(16) ?
C11 C10 H10 . . 120.1 ?
C10 C11 H11 . . 120.0 ?
C10 C11 C12 . . 120.03(16) ?
C12 C11 H11 . . 120.0 ?
C11 C12 H12 . . 119.8 ?
C11 C12 C13 . . 120.41(16) ?
C13 C12 H12 . . 119.8 ?
C8 C13 C12 . . 120.35(15) ?
C8 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C15 C14 C7 . . 128.73(12) ?
C15 C14 C19 . . 119.19(12) ?
C19 C14 C7 . . 112.03(10) ?
C14 C15 H15 . . 120.4 ?
C16 C15 C14 . . 119.16(13) ?
C16 C15 H15 . . 120.4 ?
C15 C16 H16 . . 119.3 ?
C15 C16 C17 . . 121.38(12) ?
C17 C16 H16 . . 119.3 ?
C16 C17 H17 . . 119.9 ?
C18 C17 C16 . . 120.25(13) ?
C18 C17 H17 . . 119.9 ?
C17 C18 H18 . . 120.7 ?
C17 C18 C19 . . 118.52(13) ?
C19 C18 H18 . . 120.7 ?
C14 C19 C20 . . 108.37(11) ?
C18 C19 C14 . . 121.48(11) ?
C18 C19 C20 . . 130.03(12) ?
N2 C20 C19 . . 127.41(11) ?
N2 C20 C21 . . 123.76(11) ?
C21 C20 C19 . . 108.72(11) ?
N1 C21 C7 . . 126.20(11) ?
N1 C21 C20 . . 123.29(12) ?
C20 C21 C7 . . 110.51(10) ?
N1 C22 C23 . . 121.89(11) ?
N1 C22 C27 . . 119.16(12) ?
C27 C22 C23 . . 118.94(13) ?
N2 C23 C22 . . 121.97(12) ?
N2 C23 C24 . . 118.80(12) ?
C24 C23 C22 . . 119.20(12) ?
C23 C24 H24 . . 119.9 ?
C25 C24 C23 . . 120.28(14) ?
C25 C24 H24 . . 119.9 ?
C24 C25 H25 . . 119.7 ?
C24 C25 C26 . . 120.55(14) ?
C26 C25 H25 . . 119.7 ?
C25 C26 H26 . . 119.6 ?
C27 C26 C25 . . 120.79(14) ?
C27 C26 H26 . . 119.6 ?
C22 C27 H27 . . 119.9 ?
C26 C27 C22 . . 120.24(14) ?
C26 C27 H27 . . 119.9 ?
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
N1 C21 . 1.3038(16) ?
N1 C22 . 1.3791(17) ?
N2 C20 . 1.3099(16) ?
N2 C23 . 1.3744(17) ?
C1 H1 . 0.9300 ?
C1 C2 . 1.368(3) ?
C1 C6 . 1.371(2) ?
C2 H2 . 0.9300 ?
C2 C3 . 1.383(2) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.3790(19) ?
C4 C5 . 1.3925(19) ?
C4 C7 . 1.5375(18) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.376(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.5276(19) ?
C7 C14 . 1.5408(18) ?
C7 C21 . 1.5353(17) ?
C8 C9 . 1.390(2) ?
C8 C13 . 1.384(2) ?
C9 H9 . 0.9300 ?
C9 C10 . 1.382(2) ?
C10 H10 . 0.9300 ?
C10 C11 . 1.371(3) ?
C11 H11 . 0.9300 ?
C11 C12 . 1.371(3) ?
C12 H12 . 0.9300 ?
C12 C13 . 1.386(2) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.3878(18) ?
C14 C19 . 1.3984(18) ?
C15 H15 . 0.9300 ?
C15 C16 . 1.384(2) ?
C16 H16 . 0.9300 ?
C16 C17 . 1.384(2) ?
C17 H17 . 0.9300 ?
C17 C18 . 1.3826(19) ?
C18 H18 . 0.9300 ?
C18 C19 . 1.3909(19) ?
C19 C20 . 1.4583(17) ?
C20 C21 . 1.4303(18) ?
C22 C23 . 1.4176(19) ?
C22 C27 . 1.4116(18) ?
C23 C24 . 1.4097(18) ?
C24 H24 . 0.9300 ?
C24 C25 . 1.362(2) ?
C25 H25 . 0.9300 ?
C25 C26 . 1.399(2) ?
C26 H26 . 0.9300 ?
C26 C27 . 1.362(2) ?
C27 H27 . 0.9300 ?
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
C15 H15 Cg2 2_556 0.93 2.92 3.728(2) 145
C25 H25 Cg3 3_666 0.93 2.96 3.830(3) 156
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 . . . . -0.9(3) ?
C1 C2 C3 C4 . . . . 0.0(3) ?
C2 C3 C4 C5 . . . . 0.7(2) ?
C2 C3 C4 C7 . . . . -178.05(15) ?
C3 C4 C5 C6 . . . . -0.5(2) ?
C7 C4 C5 C6 . . . . 178.31(14) ?
C2 C1 C6 C5 . . . . 1.1(3) ?
C4 C5 C6 C1 . . . . -0.4(3) ?
C3 C4 C7 C8 . . . . -131.10(13) ?
C5 C4 C7 C8 . . . . 50.19(15) ?
C3 C4 C7 C21 . . . . 103.05(14) ?
C5 C4 C7 C21 . . . . -75.66(14) ?
C3 C4 C7 C14 . . . . -6.91(17) ?
C5 C4 C7 C14 . . . . 174.37(11) ?
C21 C7 C8 C13 . . . . -13.19(16) ?
C4 C7 C8 C13 . . . . -135.71(13) ?
C14 C7 C8 C13 . . . . 98.41(14) ?
C21 C7 C8 C9 . . . . 169.96(11) ?
C4 C7 C8 C9 . . . . 47.44(15) ?
C14 C7 C8 C9 . . . . -78.44(14) ?
C13 C8 C9 C10 . . . . -1.1(2) ?
C7 C8 C9 C10 . . . . 175.84(12) ?
C8 C9 C10 C11 . . . . 1.4(2) ?
C9 C10 C11 C12 . . . . -0.1(3) ?
C10 C11 C12 C13 . . . . -1.5(3) ?
C9 C8 C13 C12 . . . . -0.4(2) ?
C7 C8 C13 C12 . . . . -177.30(13) ?
C11 C12 C13 C8 . . . . 1.8(2) ?
C8 C7 C14 C15 . . . . 52.10(17) ?
C21 C7 C14 C15 . . . . 172.54(13) ?
C4 C7 C14 C15 . . . . -72.51(17) ?
C8 C7 C14 C19 . . . . -125.24(12) ?
C21 C7 C14 C19 . . . . -4.80(13) ?
C4 C7 C14 C19 . . . . 110.15(12) ?
C19 C14 C15 C16 . . . . -0.8(2) ?
C7 C14 C15 C16 . . . . -177.99(13) ?
C14 C15 C16 C17 . . . . -0.4(2) ?
C15 C16 C17 C18 . . . . 0.7(2) ?
C16 C17 C18 C19 . . . . 0.1(2) ?
C17 C18 C19 C14 . . . . -1.3(2) ?
C17 C18 C19 C20 . . . . 174.12(13) ?
C15 C14 C19 C18 . . . . 1.67(19) ?
C7 C14 C19 C18 . . . . 179.30(11) ?
C15 C14 C19 C20 . . . . -174.64(11) ?
C7 C14 C19 C20 . . . . 2.99(14) ?
C23 N2 C20 C21 . . . . 1.74(17) ?
C23 N2 C20 C19 . . . . -173.95(11) ?
C18 C19 C20 N2 . . . . 0.7(2) ?
C14 C19 C20 N2 . . . . 176.62(12) ?
C18 C19 C20 C21 . . . . -175.49(13) ?
C14 C19 C20 C21 . . . . 0.40(14) ?
C22 N1 C21 C20 . . . . -1.39(17) ?
C22 N1 C21 C7 . . . . 178.39(11) ?
N2 C20 C21 N1 . . . . -0.19(19) ?
C19 C20 C21 N1 . . . . 176.19(11) ?
N2 C20 C21 C7 . . . . 180.00(11) ?
C19 C20 C21 C7 . . . . -3.62(13) ?
C8 C7 C21 N1 . . . . -57.34(16) ?
C4 C7 C21 N1 . . . . 66.59(15) ?
C14 C7 C21 N1 . . . . -174.85(12) ?
C8 C7 C21 C20 . . . . 122.46(11) ?
C4 C7 C21 C20 . . . . -113.61(11) ?
C14 C7 C21 C20 . . . . 4.95(12) ?
C21 N1 C22 C27 . . . . -177.33(11) ?
C21 N1 C22 C23 . . . . 1.35(17) ?
C20 N2 C23 C24 . . . . 176.38(11) ?
C20 N2 C23 C22 . . . . -1.72(17) ?
N1 C22 C23 N2 . . . . 0.21(19) ?
C27 C22 C23 N2 . . . . 178.89(11) ?
N1 C22 C23 C24 . . . . -177.89(11) ?
C27 C22 C23 C24 . . . . 0.79(18) ?
N2 C23 C24 C25 . . . . -179.05(13) ?
C22 C23 C24 C25 . . . . -0.9(2) ?
C23 C24 C25 C26 . . . . 0.6(2) ?
C24 C25 C26 C27 . . . . -0.2(2) ?
C25 C26 C27 C22 . . . . 0.1(2) ?
N1 C22 C27 C26 . . . . 178.29(12) ?
C23 C22 C27 C26 . . . . -0.4(2) ?

_cod_database_fobs_code 1559022
