#------------------------------------------------------------------------------
#$Date: 2022-09-29 04:21:32 +0300 (Thu, 29 Sep 2022) $
#$Revision: 278262 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/55/7245583.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_7245583
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            'C25 H21 N3 O'
_chemical_formula_weight         379.45
_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   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-07-28 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.29(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.660(3)
_cell_length_b                   8.7900(18)
_cell_length_c                   16.190(3)
_cell_measurement_reflns_used    112
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.37
_cell_measurement_theta_min      2.15
_cell_volume                     2058.9(7)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Syntax P-1'
_diffrn_measurement_method       'phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1471
_diffrn_reflns_av_unetI/netI     0.1211
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2141
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        20.811
_diffrn_reflns_theta_max         20.811
_diffrn_reflns_theta_min         3.092
_exptl_absorpt_coefficient_mu    0.076
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0053(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.853
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0508
_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)+(0.0568P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1280
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1015
_reflns_number_total             2141
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra05335g3.cif
_cod_data_source_block           ROI5
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7245583
_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.
;
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
C1 C 0.3449(3) 0.0945(4) 0.9495(3) 0.0530(13) Uani 1 1 d . . . . .
C2 C 0.4075(3) 0.0963(5) 0.8867(3) 0.0592(14) Uani 1 1 d . . . . .
C3 C 0.4466(3) -0.0586(5) 0.8861(3) 0.0536(13) Uani 1 1 d . . . . .
C4 C 0.5044(3) -0.1170(5) 0.8349(3) 0.0727(16) Uani 1 1 d . . . . .
H4A H 0.524286 -0.054254 0.792582 0.080 Uiso 1 1 d R U . . .
C5 C 0.5298(3) -0.2694(6) 0.8437(3) 0.0768(16) Uani 1 1 d . . . . .
H5A H 0.571307 -0.313458 0.810189 0.080 Uiso 1 1 d R U . . .
C6 C 0.4972(4) -0.3567(5) 0.9036(4) 0.0774(17) Uani 1 1 d . . . . .
H6A H 0.515761 -0.461355 0.909948 0.080 Uiso 1 1 d R U . . .
C7 C 0.4402(3) -0.2982(5) 0.9553(3) 0.0681(15) Uani 1 1 d . . . . .
H7A H 0.416823 -0.360659 0.995794 0.080 Uiso 1 1 d R U . . .
C8 C 0.4148(3) -0.1460(4) 0.9469(3) 0.0479(13) Uani 1 1 d . . . . .
C9 C 0.3518(3) -0.0544(4) 0.9889(3) 0.0498(13) Uani 1 1 d . . . . .
C10 C 0.3108(3) -0.1030(4) 1.0531(3) 0.0589(14) Uani 1 1 d . . . . .
C11 C 0.3263(3) -0.2491(5) 1.0925(3) 0.0679(16) Uani 1 1 d . . . . .
C12 C 0.2465(5) -0.0173(5) 1.0898(4) 0.093(2) Uani 1 1 d . . . . .
C13 C 0.2904(3) 0.2143(4) 0.9634(3) 0.0600(14) Uani 1 1 d . . . . .
H13A H 0.253945 0.203230 1.007307 0.080 Uiso 1 1 d R U . . .
C14 C 0.2798(3) 0.3566(4) 0.9204(3) 0.0588(14) Uani 1 1 d . . . . .
H14A H 0.317480 0.379022 0.878693 0.080 Uiso 1 1 d R U . . .
C15 C 0.2171(3) 0.4595(5) 0.9401(3) 0.0621(15) Uani 1 1 d . . . . .
H15A H 0.185578 0.429360 0.985028 0.080 Uiso 1 1 d R U . . .
C16 C 0.1910(3) 0.6043(4) 0.9022(3) 0.0544(13) Uani 1 1 d . . . . .
C17 C 0.1203(3) 0.6883(5) 0.9298(3) 0.0639(14) Uani 1 1 d . . . . .
H17A H 0.092172 0.647312 0.974610 0.080 Uiso 1 1 d R U . . .
C18 C 0.0910(3) 0.8249(4) 0.8956(3) 0.0612(14) Uani 1 1 d . . . . .
H18A H 0.041674 0.879115 0.915023 0.080 Uiso 1 1 d R U . . .
C19 C 0.1312(3) 0.8900(5) 0.8312(3) 0.0563(13) Uani 1 1 d . . . . .
C20 C 0.2039(3) 0.8076(5) 0.8046(3) 0.0588(14) Uani 1 1 d . . . . .
H20A H 0.234150 0.851989 0.762133 0.080 Uiso 1 1 d R U . . .
C21 C 0.2315(3) 0.6687(4) 0.8380(3) 0.0575(13) Uani 1 1 d . . . . .
H21A H 0.279600 0.613875 0.817160 0.080 Uiso 1 1 d R U . . .
C22 C 0.0114(4) 1.0885(5) 0.8074(3) 0.0838(18) Uani 1 1 d . . . . .
H22A H -0.015294 1.140814 0.757240 0.080 Uiso 1 1 d R U . . .
H22B H -0.029364 1.007374 0.817130 0.080 Uiso 1 1 d R U . . .
C23 C 0.0191(4) 1.1957(5) 0.8778(4) 0.123(2) Uani 1 1 d . . . . .
H23A H -0.039760 1.237076 0.884764 0.080 Uiso 1 1 d R U . . .
H23B H 0.045450 1.142445 0.927724 0.080 Uiso 1 1 d R U . . .
H23C H 0.059610 1.276806 0.867424 0.080 Uiso 1 1 d R U . . .
C24 C 0.1580(4) 1.1150(5) 0.7445(4) 0.101(2) Uani 1 1 d . . . . .
H24A H 0.150278 1.222467 0.751405 0.080 Uiso 1 1 d R U . . .
H24B H 0.222048 1.090377 0.761605 0.080 Uiso 1 1 d R U . . .
C25 C 0.1317(4) 1.0719(5) 0.6587(4) 0.112(2) Uani 1 1 d . . . . .
H25A H 0.168027 1.125731 0.623919 0.080 Uiso 1 1 d R U . . .
H25B H 0.139897 0.964421 0.652529 0.080 Uiso 1 1 d R U . . .
H25C H 0.067687 1.097321 0.642269 0.080 Uiso 1 1 d R U . . .
N1 N 0.3346(3) -0.3628(4) 1.1280(3) 0.0858(15) Uani 1 1 d . . . . .
N2 N 0.1933(4) 0.0480(5) 1.1218(4) 0.152(3) Uani 1 1 d . . . . .
N3 N 0.1012(3) 1.0240(4) 0.7967(3) 0.0784(14) Uani 1 1 d . . . . .
O1 O 0.4242(2) 0.2029(3) 0.8425(2) 0.0863(12) 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
_geom_angle_publ_flag
C13 C1 C9 128.6(4) . . ?
C13 C1 C2 123.6(4) . . ?
C9 C1 C2 107.8(4) . . ?
O1 C2 C1 127.9(4) . . ?
O1 C2 C3 125.9(5) . . ?
C1 C2 C3 106.2(4) . . ?
C4 C3 C8 122.1(4) . . ?
C4 C3 C2 128.6(5) . . ?
C8 C3 C2 109.3(4) . . ?
C3 C4 C5 118.5(4) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 121.3 . . ?
C6 C5 C4 119.4(5) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 120.9 . . ?
C7 C6 C5 122.2(4) . . ?
C7 C6 H6A 118.9 . . ?
C5 C6 H6A 118.9 . . ?
C6 C7 C8 118.7(5) . . ?
C6 C7 H7A 121.4 . . ?
C8 C7 H7A 119.9 . . ?
C3 C8 C7 119.2(4) . . ?
C3 C8 C9 109.4(4) . . ?
C7 C8 C9 131.2(4) . . ?
C10 C9 C1 127.9(4) . . ?
C10 C9 C8 125.0(4) . . ?
C1 C9 C8 107.1(4) . . ?
C9 C10 C12 124.5(4) . . ?
C9 C10 C11 124.5(4) . . ?
C12 C10 C11 111.0(4) . . ?
N1 C11 C10 175.1(5) . . ?
N2 C12 C10 177.3(5) . . ?
C1 C13 C14 128.0(4) . . ?
C1 C13 H13A 117.1 . . ?
C14 C13 H13A 114.8 . . ?
C15 C14 C13 119.4(4) . . ?
C15 C14 H14A 121.0 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 C16 129.1(4) . . ?
C14 C15 H15A 114.7 . . ?
C16 C15 H15A 116.2 . . ?
C21 C16 C17 116.6(4) . . ?
C21 C16 C15 124.1(4) . . ?
C17 C16 C15 119.2(4) . . ?
C18 C17 C16 122.3(4) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 118.2 . . ?
C17 C18 C19 121.3(4) . . ?
C17 C18 H18A 120.6 . . ?
C19 C18 H18A 118.1 . . ?
N3 C19 C18 121.1(4) . . ?
N3 C19 C20 122.3(4) . . ?
C18 C19 C20 116.5(4) . . ?
C21 C20 C19 121.8(4) . . ?
C21 C20 H20A 120.3 . . ?
C19 C20 H20A 117.9 . . ?
C20 C21 C16 121.4(4) . . ?
C20 C21 H21A 119.7 . . ?
C16 C21 H21A 118.9 . . ?
N3 C22 C23 112.4(5) . . ?
N3 C22 H22A 109.6 . . ?
C23 C22 H22A 108.6 . . ?
N3 C22 H22B 109.0 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 108.4 . . ?
C22 C23 H23A 112.1 . . ?
C22 C23 H23B 108.1 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 108.2 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 N3 108.4(5) . . ?
C25 C24 H24A 110.8 . . ?
N3 C24 H24A 111.7 . . ?
C25 C24 H24B 108.5 . . ?
N3 C24 H24B 108.8 . . ?
H24A C24 H24B 108.5 . . ?
C24 C25 H25A 110.5 . . ?
C24 C25 H25B 110.1 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 107.8 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C19 N3 C22 121.9(4) . . ?
C19 N3 C24 121.5(4) . . ?
C22 N3 C24 116.6(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
C1 C13 1.363(5) . ?
C1 C9 1.453(5) . ?
C1 C2 1.476(5) . ?
C2 O1 1.227(4) . ?
C2 C3 1.478(5) . ?
C3 C4 1.378(5) . ?
C3 C8 1.387(5) . ?
C4 C5 1.392(5) . ?
C4 H4A 0.9597 . ?
C5 C6 1.381(6) . ?
C5 H5A 0.9596 . ?
C6 C7 1.375(6) . ?
C6 H6A 0.9598 . ?
C7 C8 1.390(5) . ?
C7 H7A 0.9597 . ?
C8 C9 1.473(5) . ?
C9 C10 1.350(5) . ?
C10 C12 1.410(6) . ?
C10 C11 1.436(6) . ?
C11 N1 1.150(5) . ?
C12 N2 1.156(6) . ?
C13 C14 1.428(5) . ?
C13 H13A 0.9596 . ?
C14 C15 1.364(5) . ?
C14 H14A 0.9597 . ?
C15 C16 1.437(5) . ?
C15 H15A 0.9596 . ?
C16 C21 1.397(5) . ?
C16 C17 1.404(5) . ?
C17 C18 1.363(5) . ?
C17 H17A 0.9596 . ?
C18 C19 1.401(5) . ?
C18 H18A 0.9596 . ?
C19 N3 1.347(5) . ?
C19 C20 1.411(5) . ?
C20 C21 1.369(5) . ?
C20 H20A 0.9597 . ?
C21 H21A 0.9596 . ?
C22 N3 1.469(5) . ?
C22 C23 1.469(6) . ?
C22 H22A 0.9597 . ?
C22 H22B 0.9598 . ?
C23 H23A 0.9595 . ?
C23 H23B 0.9597 . ?
C23 H23C 0.9597 . ?
C24 C25 1.432(6) . ?
C24 N3 1.508(6) . ?
C24 H24A 0.9598 . ?
C24 H24B 0.9596 . ?
C25 H25A 0.9597 . ?
C25 H25B 0.9599 . ?
C25 H25C 0.9596 . ?
