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#$Date: 2022-06-23 10:04:23 +0300 (Thu, 23 Jun 2022) $
#$Revision: 276162 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105456.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105456
loop_
_publ_author_name
'Missioui, Mohcine'
'Essassi, El Mokhtar'
'Mague, Joel T.'
'Ramli, Youssef'
_publ_section_title
;
 Synthesis and crystal structure of
 (E)-1-benzyl-3-(4-methoxystyryl)quinoxalin-2(1H)-one, C24H20N2O2
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1323
_journal_page_last               1325
_journal_paper_doi               10.1515/ncrs-2020-0300
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C24 H20 N2 O2'
_chemical_formula_sum            'C24 H20 N2 O2'
_chemical_formula_weight         368.42
_chemical_melting_point          375
_chemical_name_systematic
;
(E)-1-benzyl-3-(4-methoxystyryl)quinoxalin-
2(1H)-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 118.990(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1713(3)
_cell_length_b                   17.7718(5)
_cell_length_c                   10.9852(3)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.5035
_cell_measurement_theta_min      4.5250
_cell_volume                     1907.67(9)
_computing_cell_refinement       'SAINT, Ver 8.40A [1]'
_computing_data_collection       'APEX3 [1]'
_computing_data_reduction        'SAINT, Ver 8.40A [1]'
_computing_molecular_graphics    'DIAMOND 4.0 [4]'
_computing_publication_material  'SHELXL 2018/3 [3]'
_computing_structure_refinement  'SHELXL 2018/3 [3]'
_computing_structure_solution    'SHELXT/5 [2]'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14266
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        69.000
_diffrn_reflns_theta_max         72.496
_diffrn_reflns_theta_min         4.525
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.279
_exptl_transmission_factor_max   0.806
_exptl_transmission_factor_min   0.740
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0265(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL 2018/3'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0870P)²+0.2556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3032
_reflns_number_total             3708
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0300_suppl.cif
_cod_data_source_block           JTM1246_0ma_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105456
_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   0.795
_shelx_estimated_absorpt_t_max   0.838
_iucr_geom_hbonds_special_details
;
Cg1 and Cg4 are, respectively, the centroids of the 
C1/C6/N1/C7/C8/N2 and CC18...C23 rings.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42090(14) 0.30337(7) 0.50175(14) 0.0800(4) Uani 1 1 d . . . . .
O2 O 0.11095(17) 0.34160(10) -0.38584(15) 0.0973(5) Uani 1 1 d . . . . .
N1 N 0.42507(12) 0.39399(7) 0.64889(13) 0.0583(3) Uani 1 1 d . . . . .
N2 N 0.31361(13) 0.49376(7) 0.42404(13) 0.0612(3) Uani 1 1 d . . . . .
C1 C 0.34999(14) 0.51788(9) 0.55669(16) 0.0574(4) Uani 1 1 d . . . . .
C2 C 0.32838(18) 0.59338(10) 0.57641(19) 0.0692(4) Uani 1 1 d . . . . .
H2 H 0.290102 0.625748 0.500394 0.083 Uiso 1 1 calc R U . . .
C3 C 0.3627(2) 0.62020(11) 0.7056(2) 0.0802(5) Uani 1 1 d . . . . .
H3 H 0.346227 0.670241 0.717464 0.096 Uiso 1 1 calc R U . . .
C4 C 0.4219(3) 0.57247(12) 0.8182(2) 0.0878(6) Uani 1 1 d . . . . .
H4 H 0.446893 0.591029 0.906516 0.105 Uiso 1 1 calc R U . . .
C5 C 0.4448(2) 0.49811(11) 0.80297(19) 0.0776(5) Uani 1 1 d . . . . .
H5 H 0.485506 0.466916 0.880559 0.093 Uiso 1 1 calc R U . . .
C6 C 0.40724(14) 0.46935(9) 0.67173(16) 0.0575(4) Uani 1 1 d . . . . .
C7 C 0.39769(15) 0.36851(9) 0.52022(17) 0.0603(4) Uani 1 1 d . . . . .
C8 C 0.33550(15) 0.42407(9) 0.40464(16) 0.0584(4) Uani 1 1 d . . . . .
C9 C 0.46967(16) 0.33806(9) 0.76112(17) 0.0644(4) Uani 1 1 d . . . . .
H9A H 0.435264 0.289123 0.719840 0.077 Uiso 1 1 calc R U . . .
H9B H 0.428360 0.350405 0.818530 0.077 Uiso 1 1 calc R U . . .
C10 C 0.62167(15) 0.33245(8) 0.85298(16) 0.0559(4) Uani 1 1 d . . . . .
C11 C 0.67210(19) 0.29902(9) 0.98287(17) 0.0675(4) Uani 1 1 d . . . . .
H11 H 0.611875 0.282658 1.013157 0.081 Uiso 1 1 calc R U . . .
C12 C 0.8114(2) 0.28995(11) 1.0673(2) 0.0831(6) Uani 1 1 d . . . . .
H12 H 0.844562 0.268132 1.154743 0.100 Uiso 1 1 calc R U . . .
C13 C 0.9013(2) 0.31302(12) 1.0228(2) 0.0866(6) Uani 1 1 d . . . . .
H13 H 0.994963 0.306624 1.079677 0.104 Uiso 1 1 calc R U . . .
C14 C 0.85219(19) 0.34547(12) 0.8941(2) 0.0808(5) Uani 1 1 d . . . . .
H14 H 0.912700 0.360749 0.863401 0.097 Uiso 1 1 calc R U . . .
C15 C 0.71331(17) 0.35553(10) 0.80997(18) 0.0676(4) Uani 1 1 d . . . . .
H15 H 0.680993 0.378108 0.723292 0.081 Uiso 1 1 calc R U . . .
C16 C 0.29872(16) 0.39615(10) 0.26666(17) 0.0648(4) Uani 1 1 d . . . . .
H16 H 0.322149 0.346868 0.258784 0.078 Uiso 1 1 calc R U . . .
C17 C 0.23374(17) 0.43660(10) 0.15108(18) 0.0670(4) Uani 1 1 d . . . . .
H17 H 0.208470 0.485162 0.160732 0.080 Uiso 1 1 calc R U . . .
C18 C 0.19795(16) 0.41265(10) 0.01056(17) 0.0656(4) Uani 1 1 d . . . . .
C19 C 0.21993(19) 0.33988(11) -0.02119(19) 0.0744(5) Uani 1 1 d . . . . .
H19 H 0.258075 0.304593 0.050111 0.089 Uiso 1 1 calc R U . . .
C20 C 0.1878(2) 0.31831(12) -0.15244(19) 0.0786(5) Uani 1 1 d . . . . .
H20 H 0.203089 0.268950 -0.169508 0.094 Uiso 1 1 calc R U . . .
C21 C 0.13372(18) 0.36854(12) -0.25801(19) 0.0750(5) Uani 1 1 d . U . . .
C22 C 0.1077(2) 0.44130(13) -0.2344(2) 0.0891(6) Uani 1 1 d . U . . .
H22 H 0.068815 0.475568 -0.307383 0.107 Uiso 1 1 calc R U . . .
C23 C 0.1407(2) 0.46317(12) -0.0987(2) 0.0847(5) Uani 1 1 d . . . . .
H23 H 0.123831 0.512328 -0.082150 0.102 Uiso 1 1 calc R U . . .
C24 C 0.0463(2) 0.38768(18) -0.5028(2) 0.1077(8) Uani 1 1 d . . . . .
H24A H 0.102723 0.430717 -0.491422 0.162 Uiso 1 1 calc R U . . .
H24B H -0.040288 0.404026 -0.513763 0.162 Uiso 1 1 calc R U . . .
H24C H 0.031888 0.360020 -0.583903 0.162 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C21 O2 C24 119.3(2) . .
C7 N1 C6 121.54(12) . .
C7 N1 C9 117.21(13) . .
C6 N1 C9 121.22(13) . .
C8 N2 C1 119.16(13) . .
N2 C1 C2 118.53(14) . .
N2 C1 C6 122.26(14) . .
C2 C1 C6 119.20(15) . .
C3 C2 C1 120.91(16) . .
C3 C2 H2 119.5 . .
C1 C2 H2 119.5 . .
C2 C3 C4 119.35(18) . .
C2 C3 H3 120.3 . .
C4 C3 H3 120.3 . .
C5 C4 C3 121.38(18) . .
C5 C4 H4 119.3 . .
C3 C4 H4 119.3 . .
C4 C5 C6 120.06(17) . .
C4 C5 H5 120.0 . .
C6 C5 H5 120.0 . .
C5 C6 N1 122.85(14) . .
C5 C6 C1 119.05(15) . .
N1 C6 C1 118.09(14) . .
O1 C7 N1 121.60(15) . .
O1 C7 C8 122.33(15) . .
N1 C7 C8 116.06(14) . .
N2 C8 C16 121.08(14) . .
N2 C8 C7 122.65(14) . .
C16 C8 C7 116.27(14) . .
N1 C9 C10 114.97(12) . .
N1 C9 H9A 108.5 . .
C10 C9 H9A 108.5 . .
N1 C9 H9B 108.5 . .
C10 C9 H9B 108.5 . .
H9A C9 H9B 107.5 . .
C15 C10 C11 118.67(15) . .
C15 C10 C9 122.35(14) . .
C11 C10 C9 118.88(14) . .
C12 C11 C10 120.27(16) . .
C12 C11 H11 119.9 . .
C10 C11 H11 119.9 . .
C13 C12 C11 120.33(17) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C14 C13 C12 119.74(17) . .
C14 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
C13 C14 C15 120.19(18) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C14 C15 C10 120.79(16) . .
C14 C15 H15 119.6 . .
C10 C15 H15 119.6 . .
C17 C16 C8 124.07(16) . .
C17 C16 H16 118.0 . .
C8 C16 H16 118.0 . .
C16 C17 C18 126.65(17) . .
C16 C17 H17 116.7 . .
C18 C17 H17 116.7 . .
C23 C18 C19 116.71(17) . .
C23 C18 C17 120.24(17) . .
C19 C18 C17 123.04(16) . .
C20 C19 C18 122.62(18) . .
C20 C19 H19 118.7 . .
C18 C19 H19 118.7 . .
C21 C20 C19 120.09(19) . .
C21 C20 H20 120.0 . .
C19 C20 H20 120.0 . .
C20 C21 C22 120.38(18) . .
C20 C21 O2 115.31(19) . .
C22 C21 O2 124.29(19) . .
C21 C22 C23 119.24(18) . .
C21 C22 H22 120.4 . .
C23 C22 H22 120.4 . .
C18 C23 C22 120.94(19) . .
C18 C23 H23 119.5 . .
C22 C23 H23 119.5 . .
O2 C24 H24A 109.5 . .
O2 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
O2 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.225(2) .
O2 C21 1.385(2) .
O2 C24 1.394(3) .
N1 C7 1.370(2) .
N1 C6 1.395(2) .
N1 C9 1.4700(19) .
N2 C8 1.300(2) .
N2 C1 1.378(2) .
C1 C2 1.399(2) .
C1 C6 1.402(2) .
C2 C3 1.364(3) .
C2 H2 0.9300 .
C3 C4 1.376(3) .
C3 H3 0.9300 .
C4 C5 1.372(3) .
C4 H4 0.9300 .
C5 C6 1.389(2) .
C5 H5 0.9300 .
C7 C8 1.488(2) .
C8 C16 1.452(2) .
C9 C10 1.500(2) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C15 1.381(2) .
C10 C11 1.388(2) .
C11 C12 1.382(3) .
C11 H11 0.9300 .
C12 C13 1.376(3) .
C12 H12 0.9300 .
C13 C14 1.371(3) .
C13 H13 0.9300 .
C14 C15 1.380(2) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 C17 1.328(2) .
C16 H16 0.9300 .
C17 C18 1.458(2) .
C17 H17 0.9300 .
C18 C23 1.382(3) .
C18 C19 1.392(3) .
C19 C20 1.361(3) .
C19 H19 0.9300 .
C20 C21 1.352(3) .
C20 H20 0.9300 .
C21 C22 1.377(3) .
C22 C23 1.406(3) .
C22 H22 0.9300 .
C23 H23 0.9300 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C14 H14 Cg4 0.93 2.81 3.589(3) 158 1_656 y
C11 H11 O1 0.93 2.58 3.434(3) 153 4_566 y
C20 H20 O1 0.93 2.58 3.170(2) 122 4_565 yes
C24 H24A Cg1 0.96 2.87 3.585(3) 132 1_554 y
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C8 N2 C1 C2 178.72(14) . . . .
C8 N2 C1 C6 -1.5(2) . . . .
N2 C1 C2 C3 -179.94(16) . . . .
C6 C1 C2 C3 0.3(2) . . . .
C1 C2 C3 C4 1.3(3) . . . .
C2 C3 C4 C5 -1.3(3) . . . .
C3 C4 C5 C6 -0.4(3) . . . .
C4 C5 C6 N1 -178.61(18) . . . .
C4 C5 C6 C1 2.0(3) . . . .
C7 N1 C6 C5 -174.48(15) . . . .
C9 N1 C6 C5 7.6(2) . . . .
C7 N1 C6 C1 4.9(2) . . . .
C9 N1 C6 C1 -172.98(12) . . . .
N2 C1 C6 C5 178.29(14) . . . .
C2 C1 C6 C5 -1.9(2) . . . .
N2 C1 C6 N1 -1.1(2) . . . .
C2 C1 C6 N1 178.67(13) . . . .
C6 N1 C7 O1 175.63(14) . . . .
C9 N1 C7 O1 -6.4(2) . . . .
C6 N1 C7 C8 -5.7(2) . . . .
C9 N1 C7 C8 172.26(12) . . . .
C1 N2 C8 C16 179.95(13) . . . .
C1 N2 C8 C7 0.5(2) . . . .
O1 C7 C8 N2 -178.30(15) . . . .
N1 C7 C8 N2 3.1(2) . . . .
O1 C7 C8 C16 2.2(2) . . . .
N1 C7 C8 C16 -176.44(13) . . . .
C7 N1 C9 C10 96.62(16) . . . .
C6 N1 C9 C10 -85.40(17) . . . .
N1 C9 C10 C15 -22.5(2) . . . .
N1 C9 C10 C11 161.18(14) . . . .
C15 C10 C11 C12 0.7(2) . . . .
C9 C10 C11 C12 177.08(16) . . . .
C10 C11 C12 C13 -0.9(3) . . . .
C11 C12 C13 C14 0.3(3) . . . .
C12 C13 C14 C15 0.5(3) . . . .
C13 C14 C15 C10 -0.7(3) . . . .
C11 C10 C15 C14 0.1(3) . . . .
C9 C10 C15 C14 -176.15(17) . . . .
N2 C8 C16 C17 -4.4(2) . . . .
C7 C8 C16 C17 175.08(15) . . . .
C8 C16 C17 C18 177.90(15) . . . .
C16 C17 C18 C23 -174.28(18) . . . .
C16 C17 C18 C19 5.0(3) . . . .
C23 C18 C19 C20 0.2(3) . . . .
C17 C18 C19 C20 -179.12(17) . . . .
C18 C19 C20 C21 0.8(3) . . . .
C19 C20 C21 C22 -1.5(3) . . . .
C19 C20 C21 O2 177.07(17) . . . .
C24 O2 C21 C20 175.37(18) . . . .
C24 O2 C21 C22 -6.1(3) . . . .
C20 C21 C22 C23 1.3(3) . . . .
O2 C21 C22 C23 -177.15(18) . . . .
C19 C18 C23 C22 -0.4(3) . . . .
C17 C18 C23 C22 178.94(18) . . . .
C21 C22 C23 C18 -0.4(3) . . . .
