#------------------------------------------------------------------------------
#$Date: 2022-09-29 04:21:32 +0300 (Thu, 29 Sep 2022) $
#$Revision: 278262 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/55/7245582.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_7245582
loop_
_publ_author_name
'Sigalov, Mark'
'Mazor, Royi'
'Ellern, Arkady'
'Larina, Nina'
'Lokshin, Vladimir'
'Khodorkovsky, Vladimir'
_publ_section_title
;
 Conjugated donor--acceptor substituted systems involving the
 1,3-indandione-derived electron accepting moieties
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              27766
_journal_page_last               27774
_journal_paper_doi               10.1039/D2RA05335G
_journal_volume                  12
_journal_year                    2022
_chemical_formula_sum            'C28 H21 N5'
_chemical_formula_weight         427.50
_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-2014/7
_audit_update_record
;
2021-05-11 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                104.04(4)
_cell_angle_beta                 91.86(4)
_cell_angle_gamma                97.94(4)
_cell_formula_units_Z            2
_cell_length_a                   8.190(4)
_cell_length_b                   11.379(5)
_cell_length_c                   12.636(6)
_cell_measurement_reflns_used    420
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.25
_cell_measurement_theta_min      2.18
_cell_volume                     1128.8(9)
_computing_cell_refinement       'Syntax P-1 Suite'
_computing_data_collection       'Syntax P-1 Suite'
_computing_data_reduction        'Syntax P-1 Suite'
_computing_molecular_graphics    'XSHELL, Bruker'
_computing_publication_material  "'XSHELL, Bruker"
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Syntax P-1 Suite'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Syntax P-1'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2846
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        21.721
_diffrn_reflns_theta_max         21.721
_diffrn_reflns_theta_min         2.169
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       0.024(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         2619
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0731
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1994
_refine_ls_wR_factor_ref         0.2512
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2000
_reflns_number_total             2619
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra05335g3.cif
_cod_data_source_block           RV1
_cod_original_cell_volume        1128.8(10)
_cod_database_code               7245582
_shelx_shelxl_version_number     2014/7
_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   0.970
_shelx_estimated_absorpt_t_max   0.985
_exptl_absorpt_special_details   'phi scan'
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
N1 N 0.8161(5) 0.6854(4) 0.6501(3) 0.0720(13) Uani 1 1 d . . . . .
N2 N 0.5214(6) 0.5524(4) 0.8742(4) 0.0767(13) Uani 1 1 d . . . . .
N3 N 0.6635(5) 1.2194(4) 0.4821(3) 0.0702(12) Uani 1 1 d . . . . .
N4 N 1.5366(5) 0.8910(4) 0.8630(4) 0.0687(12) Uani 1 1 d . . . . .
N5 N 1.5727(5) 0.8070(4) 1.1670(4) 0.0687(12) Uani 1 1 d . . . . .
C1 C 0.9271(5) 0.7172(3) 0.9301(3) 0.0376(10) Uani 1 1 d . . . . .
C2 C 1.0821(5) 0.7937(3) 0.9211(3) 0.0381(10) Uani 1 1 d . . . . .
C3 C 1.2032(5) 0.7740(3) 0.9994(3) 0.0371(10) Uani 1 1 d . . . . .
C4 C 1.1131(5) 0.7038(3) 1.0694(3) 0.0343(10) Uani 1 1 d . . . . .
C5 C 1.1671(5) 0.6637(3) 1.1568(3) 0.0404(10) Uani 1 1 d . . . . .
H5 H 1.2804 0.6806 1.1822 0.049 Uiso 1 1 calc R U . . .
C6 C 1.0522(5) 0.5982(4) 1.2068(3) 0.0464(11) Uani 1 1 d . . . . .
H6 H 1.0869 0.5724 1.2688 0.056 Uiso 1 1 calc R U . . .
C7 C 0.8899(5) 0.5700(4) 1.1688(3) 0.0476(11) Uani 1 1 d . . . . .
H7 H 0.8143 0.5241 1.2046 0.057 Uiso 1 1 calc R U . . .
C8 C 0.8339(5) 0.6062(4) 1.0806(3) 0.0457(11) Uani 1 1 d . . . . .
H8 H 0.7208 0.5857 1.0547 0.055 Uiso 1 1 calc R U . . .
C9 C 0.9463(4) 0.6741(3) 1.0291(3) 0.0368(10) Uani 1 1 d . . . . .
C10 C 0.7982(5) 0.6768(3) 0.8514(3) 0.0418(10) Uani 1 1 d . . . . .
C11 C 0.8099(5) 0.6861(4) 0.7412(4) 0.0482(12) Uani 1 1 d . . . . .
C12 C 0.6462(6) 0.6067(4) 0.8675(3) 0.0491(12) Uani 1 1 d . . . . .
C13 C 1.1048(5) 0.8853(3) 0.8656(3) 0.0427(11) Uani 1 1 d . . . . .
H13 H 1.2166 0.9200 0.8635 0.051 Uiso 1 1 calc R U . . .
C14 C 0.9905(5) 0.9342(3) 0.8128(3) 0.0445(11) Uani 1 1 d . . . . .
H14 H 0.8760 0.9129 0.8207 0.053 Uiso 1 1 calc R U . . .
C15 C 1.0398(5) 1.0128(3) 0.7494(3) 0.0448(11) Uani 1 1 d . . . . .
H15 H 1.1557 1.0366 0.7498 0.054 Uiso 1 1 calc R U . . .
C16 C 0.9406(5) 1.0635(3) 0.6830(3) 0.0387(10) Uani 1 1 d . . . . .
C17 C 1.0162(5) 1.1294(4) 0.6123(3) 0.0509(12) Uani 1 1 d . . . . .
H17 H 1.1331 1.1391 0.6107 0.061 Uiso 1 1 calc R U . . .
C18 C 0.9293(6) 1.1797(4) 0.5464(3) 0.0565(13) Uani 1 1 d . . . . .
H18 H 0.9859 1.2224 0.4992 0.068 Uiso 1 1 calc R U . . .
C19 C 0.7539(6) 1.1695(4) 0.5469(3) 0.0521(12) Uani 1 1 d . . . . .
C20 C 0.6778(5) 1.1036(4) 0.6174(3) 0.0501(12) Uani 1 1 d . . . . .
H20 H 0.5612 1.0957 0.6209 0.060 Uiso 1 1 calc R U . . .
C21 C 0.7680(5) 1.0506(3) 0.6812(3) 0.0442(11) Uani 1 1 d . . . . .
H21 H 0.7118 1.0038 0.7255 0.053 Uiso 1 1 calc R U . . .
C22 C 0.4900(7) 1.2300(5) 0.4979(4) 0.0791(17) Uani 1 1 d . U . . .
H22A H 0.4325 1.1506 0.5063 0.095 Uiso 1 1 calc R U . . .
H22B H 0.4397 1.2457 0.4314 0.095 Uiso 1 1 calc R U . . .
C23 C 0.4611(8) 1.3287(5) 0.5945(5) 0.0864(18) Uani 1 1 d . U . . .
H23A H 0.5126 1.3154 0.6609 0.130 Uiso 1 1 calc R U . . .
H23B H 0.3420 1.3269 0.6016 0.130 Uiso 1 1 calc R U . . .
H23C H 0.5097 1.4086 0.5844 0.130 Uiso 1 1 calc R U . . .
C24 C 0.7362(10) 1.2669(7) 0.3934(5) 0.115(2) Uani 1 1 d D U . . .
H24A H 0.6532 1.2512 0.3310 0.138 Uiso 1 1 calc R U . . .
H24B H 0.8311 1.2248 0.3679 0.138 Uiso 1 1 calc R U . . .
C25 C 0.7943(12) 1.4054(7) 0.4357(9) 0.178(4) Uani 1 1 d D U . . .
H25A H 0.7049 1.4446 0.4723 0.266 Uiso 1 1 calc R U . . .
H25B H 0.8243 1.4404 0.3741 0.266 Uiso 1 1 calc R U . . .
H25C H 0.8907 1.4196 0.4877 0.266 Uiso 1 1 calc R U . . .
C26 C 1.3713(5) 0.8109(3) 1.0076(3) 0.0415(11) Uani 1 1 d . . . . .
C27 C 1.4584(5) 0.8562(4) 0.9263(4) 0.0473(11) Uani 1 1 d . . . . .
C28 C 1.4793(5) 0.8052(4) 1.0964(4) 0.0471(11) 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'
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
_geom_angle_publ_flag
C19 N3 C22 121.8(4) . . ?
C19 N3 C24 121.6(5) . . ?
C22 N3 C24 116.6(4) . . ?
C10 C1 C2 126.2(3) . . ?
C10 C1 C9 125.8(3) . . ?
C2 C1 C9 107.2(3) . . ?
C13 C2 C3 124.8(3) . . ?
C13 C2 C1 127.1(3) . . ?
C3 C2 C1 107.0(3) . . ?
C26 C3 C2 127.4(4) . . ?
C26 C3 C4 125.2(4) . . ?
C2 C3 C4 107.4(3) . . ?
C5 C4 C9 120.7(3) . . ?
C5 C4 C3 131.3(3) . . ?
C9 C4 C3 108.0(3) . . ?
C4 C5 C6 118.2(4) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C7 C6 C5 121.4(4) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 121.4(4) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C9 118.7(4) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C8 C9 C4 119.5(3) . . ?
C8 C9 C1 131.3(4) . . ?
C4 C9 C1 109.0(3) . . ?
C1 C10 C11 123.4(4) . . ?
C1 C10 C12 123.3(4) . . ?
C11 C10 C12 112.7(4) . . ?
N1 C11 C10 175.5(5) . . ?
N2 C12 C10 175.5(4) . . ?
C14 C13 C2 130.3(4) . . ?
C14 C13 H13 114.8 . . ?
C2 C13 H13 114.8 . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 128.6(4) . . ?
C14 C15 H15 115.7 . . ?
C16 C15 H15 115.7 . . ?
C21 C16 C17 116.4(4) . . ?
C21 C16 C15 124.0(3) . . ?
C17 C16 C15 119.5(4) . . ?
C18 C17 C16 122.7(4) . . ?
C18 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
C17 C18 C19 120.9(4) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
N3 C19 C20 121.2(5) . . ?
N3 C19 C18 122.2(4) . . ?
C20 C19 C18 116.6(4) . . ?
C21 C20 C19 121.5(4) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C16 121.9(4) . . ?
C20 C21 H21 119.1 . . ?
C16 C21 H21 119.1 . . ?
N3 C22 C23 114.6(4) . . ?
N3 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
N3 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 C25 109.1(5) . . ?
N3 C24 H24A 109.9 . . ?
C25 C24 H24A 109.9 . . ?
N3 C24 H24B 109.9 . . ?
C25 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C3 C26 C28 124.2(4) . . ?
C3 C26 C27 123.7(4) . . ?
C28 C26 C27 112.1(3) . . ?
N4 C27 C26 176.1(4) . . ?
N5 C28 C26 175.6(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.151(5) . ?
N2 C12 1.136(5) . ?
N3 C19 1.357(6) . ?
N3 C22 1.459(7) . ?
N3 C24 1.466(8) . ?
N4 C27 1.150(5) . ?
N5 C28 1.150(5) . ?
C1 C10 1.375(6) . ?
C1 C2 1.461(5) . ?
C1 C9 1.463(5) . ?
C2 C13 1.387(5) . ?
C2 C3 1.455(5) . ?
C3 C26 1.376(5) . ?
C3 C4 1.479(5) . ?
C4 C5 1.375(5) . ?
C4 C9 1.408(5) . ?
C5 C6 1.383(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.366(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.366(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(5) . ?
C8 H8 0.9500 . ?
C10 C11 1.428(7) . ?
C10 C12 1.431(7) . ?
C13 C14 1.384(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.369(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.420(5) . ?
C15 H15 0.9500 . ?
C16 C21 1.399(6) . ?
C16 C17 1.406(5) . ?
C17 C18 1.353(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.425(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.405(6) . ?
C20 C21 1.372(6) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.495(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.538(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C28 1.425(6) . ?
C26 C27 1.427(6) . ?
