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#$Date: 2022-06-03 11:30:37 +0300 (Fri, 03 Jun 2022) $
#$Revision: 275766 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105335.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_8105335
loop_
_publ_author_name
'Wang, Feng'
'Shen, Lun-Hua'
'Jiang, Jin-Ke'
'Chen, Nian-gen'
_publ_section_title
;
 Crystal structure of
 (E)-1-(2-cyano-3-oxo-1-phenylprop-1-en-1-yl)-3,7-diphenylindolizine-6-carbonitrile,
 C31H19N3O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              933
_journal_page_last               934
_journal_paper_doi               10.1515/ncrs-2020-0106
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C31 H19 N3 O'
_chemical_formula_sum            'C31 H19 N3 O'
_chemical_formula_weight         449.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                97.550(9)
_cell_angle_beta                 101.415(9)
_cell_angle_gamma                109.603(9)
_cell_formula_units_Z            2
_cell_length_a                   8.672(5)
_cell_length_b                   10.725(6)
_cell_length_c                   13.886(8)
_cell_measurement_reflns_used    2349
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.53
_cell_measurement_theta_min      2.58
_cell_volume                     1164.9(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5907
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.532
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0439
_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)+(0.0700P)²+0.1079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1288
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3168
_reflns_number_total             4060
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0106_suppl.cif
_cod_data_source_block           2
_cod_database_code               8105335
_shelx_shelxl_version_number     2018/3
_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   0.981
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.3097(2) 0.40101(16) 0.56440(12) 0.0357(4) Uani 1 1 d . . . . .
C2 C 0.3088(2) 0.52698(17) 0.53712(12) 0.0348(4) Uani 1 1 d . . . . .
C3 C 0.4106(2) 0.64391(17) 0.60777(12) 0.0357(4) Uani 1 1 d . . . . .
H3 H 0.420844 0.726881 0.590869 0.043 Uiso 1 1 calc R U . . .
C4 C 0.5000(2) 0.64362(16) 0.70451(12) 0.0343(4) Uani 1 1 d . . . . .
C5 C 0.3957(2) 0.39959(17) 0.65828(12) 0.0360(4) Uani 1 1 d . . . . .
H5 H 0.395031 0.317674 0.673737 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2217(2) 0.26982(19) 0.49658(13) 0.0443(5) Uani 1 1 d . . . . .
C7 C 0.2037(2) 0.53535(17) 0.44035(12) 0.0351(4) Uani 1 1 d . . . . .
C8 C 0.1603(2) 0.44195(19) 0.34975(13) 0.0454(5) Uani 1 1 d . . . . .
H8 H 0.197771 0.370190 0.347888 0.054 Uiso 1 1 calc R U . . .
C9 C 0.0619(3) 0.4549(2) 0.26253(14) 0.0565(6) Uani 1 1 d . . . . .
H9 H 0.032152 0.390412 0.203474 0.068 Uiso 1 1 calc R U . . .
C10 C 0.0075(3) 0.5620(2) 0.26212(15) 0.0562(5) Uani 1 1 d . . . . .
H10 H -0.056885 0.570624 0.203148 0.067 Uiso 1 1 calc R U . . .
C11 C 0.0506(3) 0.6568(2) 0.35125(15) 0.0507(5) Uani 1 1 d . . . . .
H11 H 0.015991 0.730115 0.351717 0.061 Uiso 1 1 calc R U . . .
C12 C 0.1448(2) 0.64261(19) 0.43951(14) 0.0445(5) Uani 1 1 d . . . . .
H12 H 0.169470 0.705002 0.499004 0.053 Uiso 1 1 calc R U . . .
C13 C 0.5818(2) 0.53816(17) 0.82828(12) 0.0360(4) Uani 1 1 d . . . . .
C14 C 0.6653(2) 0.67569(17) 0.86180(12) 0.0372(4) Uani 1 1 d . . . . .
H14 H 0.742133 0.717667 0.924186 0.045 Uiso 1 1 calc R U . . .
C15 C 0.6174(2) 0.74494(17) 0.78735(12) 0.0358(4) Uani 1 1 d . . . . .
C16 C 0.5843(2) 0.42703(17) 0.88014(12) 0.0359(4) Uani 1 1 d . . . . .
C17 C 0.4378(2) 0.31372(18) 0.87128(13) 0.0432(4) Uani 1 1 d . . . . .
H17 H 0.334273 0.307513 0.831908 0.052 Uiso 1 1 calc R U . . .
C18 C 0.4458(3) 0.21090(19) 0.92069(14) 0.0473(5) Uani 1 1 d . . . . .
H18 H 0.348225 0.135559 0.913292 0.057 Uiso 1 1 calc R U . . .
C19 C 0.5980(3) 0.2198(2) 0.98081(14) 0.0508(5) Uani 1 1 d . . . . .
H19 H 0.603370 0.150096 1.013108 0.061 Uiso 1 1 calc R U . . .
C20 C 0.7427(3) 0.3330(2) 0.99277(14) 0.0526(5) Uani 1 1 d . . . . .
H20 H 0.844774 0.339955 1.034441 0.063 Uiso 1 1 calc R U . . .
C21 C 0.7368(2) 0.43543(19) 0.94345(13) 0.0462(5) Uani 1 1 d . . . . .
H21 H 0.834958 0.510892 0.952215 0.055 Uiso 1 1 calc R U . . .
C22 C 0.6735(2) 0.89055(16) 0.79191(12) 0.0349(4) Uani 1 1 d . . . . .
C23 C 0.5451(2) 0.93981(16) 0.73936(12) 0.0356(4) Uani 1 1 d . . . . .
C24 C 0.3809(2) 0.89496(18) 0.75326(13) 0.0419(4) Uani 1 1 d . . . . .
H24 H 0.356054 0.841095 0.799677 0.050 Uiso 1 1 calc R U . . .
C25 C 0.2554(2) 0.9298(2) 0.69880(14) 0.0491(5) Uani 1 1 d . . . . .
H25 H 0.147203 0.899307 0.708901 0.059 Uiso 1 1 calc R U . . .
C26 C 0.2902(3) 1.0098(2) 0.62945(15) 0.0548(5) Uani 1 1 d . . . . .
H26 H 0.205381 1.032254 0.592411 0.066 Uiso 1 1 calc R U . . .
C27 C 0.4524(3) 1.0565(2) 0.61536(15) 0.0554(5) Uani 1 1 d . . . . .
H27 H 0.476188 1.111245 0.569364 0.067 Uiso 1 1 calc R U . . .
C28 C 0.5796(2) 1.02198(18) 0.66952(14) 0.0463(5) Uani 1 1 d . . . . .
H28 H 0.687690 1.053463 0.659383 0.056 Uiso 1 1 calc R U . . .
C29 C 0.8372(2) 0.97846(17) 0.83992(13) 0.0386(4) Uani 1 1 d . . . . .
C30 C 0.9683(2) 0.92835(18) 0.87584(14) 0.0435(4) Uani 1 1 d . . . . .
C31 C 0.8933(2) 1.12735(19) 0.85718(14) 0.0479(5) Uani 1 1 d . . . . .
H31 H 0.810771 1.164302 0.842233 0.057 Uiso 1 1 calc R U . . .
N1 N 0.1564(2) 0.16341(18) 0.44536(13) 0.0675(6) Uani 1 1 d . . . . .
N2 N 0.48267(17) 0.51762(13) 0.72977(10) 0.0341(3) Uani 1 1 d . . . . .
N3 N 1.0779(2) 0.89456(18) 0.90389(14) 0.0591(5) Uani 1 1 d . . . . .
O1 O 1.03928(18) 1.20472(14) 0.88948(12) 0.0663(4) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C5 C1 C6 115.40(15) . .
C5 C1 C2 121.19(15) . .
C6 C1 C2 123.41(15) . .
C3 C2 C1 115.88(15) . .
C3 C2 C7 119.91(15) . .
C1 C2 C7 124.19(15) . .
C2 C3 C4 123.16(16) . .
C2 C3 H3 118.4 . .
C4 C3 H3 118.4 . .
N2 C4 C3 118.04(14) . .
N2 C4 C15 107.04(14) . .
C3 C4 C15 134.84(16) . .
C1 C5 N2 120.90(15) . .
C1 C5 H5 119.6 . .
N2 C5 H5 119.6 . .
N1 C6 C1 176.95(19) . .
C8 C7 C12 117.58(16) . .
C8 C7 C2 123.59(16) . .
C12 C7 C2 118.83(15) . .
C9 C8 C7 120.90(18) . .
C9 C8 H8 119.5 . .
C7 C8 H8 119.5 . .
C10 C9 C8 121.03(18) . .
C10 C9 H9 119.5 . .
C8 C9 H9 119.5 . .
C9 C10 C11 119.04(18) . .
C9 C10 H10 120.5 . .
C11 C10 H10 120.5 . .
C12 C11 C10 120.33(18) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C11 C12 C7 121.07(17) . .
C11 C12 H12 119.5 . .
C7 C12 H12 119.5 . .
C14 C13 N2 106.54(14) . .
C14 C13 C16 129.93(15) . .
N2 C13 C16 123.51(15) . .
C13 C14 C15 110.33(15) . .
C13 C14 H14 124.8 . .
C15 C14 H14 124.8 . .
C4 C15 C14 106.37(15) . .
C4 C15 C22 124.99(15) . .
C14 C15 C22 128.64(15) . .
C17 C16 C21 118.03(16) . .
C17 C16 C13 122.46(16) . .
C21 C16 C13 119.48(15) . .
C18 C17 C16 120.62(17) . .
C18 C17 H17 119.7 . .
C16 C17 H17 119.7 . .
C19 C18 C17 120.36(18) . .
C19 C18 H18 119.8 . .
C17 C18 H18 119.8 . .
C18 C19 C20 119.67(18) . .
C18 C19 H19 120.2 . .
C20 C19 H19 120.2 . .
C21 C20 C19 120.58(18) . .
C21 C20 H20 119.7 . .
C19 C20 H20 119.7 . .
C20 C21 C16 120.69(17) . .
C20 C21 H21 119.7 . .
C16 C21 H21 119.7 . .
C29 C22 C15 122.38(15) . .
C29 C22 C23 121.33(15) . .
C15 C22 C23 116.27(14) . .
C28 C23 C24 118.38(16) . .
C28 C23 C22 121.64(16) . .
C24 C23 C22 119.79(15) . .
C25 C24 C23 120.90(17) . .
C25 C24 H24 119.5 . .
C23 C24 H24 119.5 . .
C26 C25 C24 120.29(19) . .
C26 C25 H25 119.9 . .
C24 C25 H25 119.9 . .
C25 C26 C27 119.71(18) . .
C25 C26 H26 120.1 . .
C27 C26 H26 120.1 . .
C26 C27 C28 120.55(19) . .
C26 C27 H27 119.7 . .
C28 C27 H27 119.7 . .
C27 C28 C23 120.16(18) . .
C27 C28 H28 119.9 . .
C23 C28 H28 119.9 . .
C22 C29 C30 121.11(16) . .
C22 C29 C31 123.99(16) . .
C30 C29 C31 114.89(16) . .
N3 C30 C29 176.6(2) . .
O1 C31 C29 124.48(19) . .
O1 C31 H31 117.8 . .
C29 C31 H31 117.8 . .
C5 N2 C4 120.26(14) . .
C5 N2 C13 129.60(14) . .
C4 N2 C13 109.66(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C5 1.372(2) .
C1 C6 1.448(3) .
C1 C2 1.452(2) .
C2 C3 1.380(2) .
C2 C7 1.499(2) .
C3 C4 1.413(2) .
C3 H3 0.9300 .
C4 N2 1.407(2) .
C4 C15 1.416(2) .
C5 N2 1.375(2) .
C5 H5 0.9300 .
C6 N1 1.150(2) .
C7 C8 1.399(2) .
C7 C12 1.407(3) .
C8 C9 1.389(3) .
C8 H8 0.9300 .
C9 C10 1.380(3) .
C9 H9 0.9300 .
C10 C11 1.392(3) .
C10 H10 0.9300 .
C11 C12 1.389(3) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.373(2) .
C13 N2 1.410(2) .
C13 C16 1.475(2) .
C14 C15 1.425(2) .
C14 H14 0.9300 .
C15 C22 1.460(2) .
C16 C17 1.403(2) .
C16 C21 1.404(2) .
C17 C18 1.387(3) .
C17 H17 0.9300 .
C18 C19 1.381(3) .
C18 H18 0.9300 .
C19 C20 1.385(3) .
C19 H19 0.9300 .
C20 C21 1.379(3) .
C20 H20 0.9300 .
C21 H21 0.9300 .
C22 C29 1.383(2) .
C22 C23 1.492(2) .
C23 C28 1.403(3) .
C23 C24 1.403(3) .
C24 C25 1.385(3) .
C24 H24 0.9300 .
C25 C26 1.383(3) .
C25 H25 0.9300 .
C26 C27 1.389(3) .
C26 H26 0.9300 .
C27 C28 1.392(3) .
C27 H27 0.9300 .
C28 H28 0.9300 .
C29 C30 1.445(3) .
C29 C31 1.475(3) .
C30 N3 1.144(2) .
C31 O1 1.211(2) .
C31 H31 0.9300 .
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
C5 C1 C2 C3 5.4(2) . . . .
C6 C1 C2 C3 -174.82(16) . . . .
C5 C1 C2 C7 -173.34(15) . . . .
C6 C1 C2 C7 6.4(3) . . . .
C1 C2 C3 C4 -5.3(2) . . . .
C7 C2 C3 C4 173.49(15) . . . .
C2 C3 C4 N2 -0.5(3) . . . .
C2 C3 C4 C15 175.78(18) . . . .
C6 C1 C5 N2 -179.30(15) . . . .
C2 C1 C5 N2 0.5(3) . . . .
C3 C2 C7 C8 149.87(18) . . . .
C1 C2 C7 C8 -31.4(3) . . . .
C3 C2 C7 C12 -30.0(2) . . . .
C1 C2 C7 C12 148.65(17) . . . .
C12 C7 C8 C9 -0.3(3) . . . .
C2 C7 C8 C9 179.78(18) . . . .
C7 C8 C9 C10 1.6(3) . . . .
C8 C9 C10 C11 -1.0(3) . . . .
C9 C10 C11 C12 -0.9(3) . . . .
C10 C11 C12 C7 2.2(3) . . . .
C8 C7 C12 C11 -1.5(3) . . . .
C2 C7 C12 C11 178.38(16) . . . .
N2 C13 C14 C15 1.81(19) . . . .
C16 C13 C14 C15 -176.81(17) . . . .
N2 C4 C15 C14 -1.08(18) . . . .
C3 C4 C15 C14 -177.69(19) . . . .
N2 C4 C15 C22 179.17(15) . . . .
C3 C4 C15 C22 2.6(3) . . . .
C13 C14 C15 C4 -0.47(19) . . . .
C13 C14 C15 C22 179.27(16) . . . .
C14 C13 C16 C17 139.55(19) . . . .
N2 C13 C16 C17 -38.9(3) . . . .
C14 C13 C16 C21 -38.4(3) . . . .
N2 C13 C16 C21 143.16(17) . . . .
C21 C16 C17 C18 -2.5(3) . . . .
C13 C16 C17 C18 179.47(16) . . . .
C16 C17 C18 C19 1.1(3) . . . .
C17 C18 C19 C20 0.9(3) . . . .
C18 C19 C20 C21 -1.4(3) . . . .
C19 C20 C21 C16 0.0(3) . . . .
C17 C16 C21 C20 2.0(3) . . . .
C13 C16 C21 C20 -179.94(17) . . . .
C4 C15 C22 C29 -144.31(18) . . . .
C14 C15 C22 C29 36.0(3) . . . .
C4 C15 C22 C23 34.2(2) . . . .
C14 C15 C22 C23 -145.54(18) . . . .
C29 C22 C23 C28 50.4(2) . . . .
C15 C22 C23 C28 -128.11(17) . . . .
C29 C22 C23 C24 -134.83(18) . . . .
C15 C22 C23 C24 46.7(2) . . . .
C28 C23 C24 C25 0.6(2) . . . .
C22 C23 C24 C25 -174.39(16) . . . .
C23 C24 C25 C26 0.0(3) . . . .
C24 C25 C26 C27 -0.7(3) . . . .
C25 C26 C27 C28 0.8(3) . . . .
C26 C27 C28 C23 -0.2(3) . . . .
C24 C23 C28 C27 -0.5(3) . . . .
C22 C23 C28 C27 174.40(16) . . . .
C15 C22 C29 C30 9.0(3) . . . .
C23 C22 C29 C30 -169.42(16) . . . .
C15 C22 C29 C31 -172.08(16) . . . .
C23 C22 C29 C31 9.5(3) . . . .
C22 C29 C31 O1 -171.89(18) . . . .
C30 C29 C31 O1 7.1(3) . . . .
C1 C5 N2 C4 -6.7(2) . . . .
C1 C5 N2 C13 -177.87(16) . . . .
C3 C4 N2 C5 6.8(2) . . . .
C15 C4 N2 C5 -170.51(15) . . . .
C3 C4 N2 C13 179.51(15) . . . .
C15 C4 N2 C13 2.23(18) . . . .
C14 C13 N2 C5 169.36(16) . . . .
C16 C13 N2 C5 -11.9(3) . . . .
C14 C13 N2 C4 -2.51(19) . . . .
C16 C13 N2 C4 176.23(15) . . . .
