#------------------------------------------------------------------------------
#$Date: 2023-08-05 12:35:32 +0300 (Sat, 05 Aug 2023) $
#$Revision: 285527 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/69/7246944.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_7246944
loop_
_publ_author_name
'Sosorev, Andrey Yu'
'Ponomarev, Igor I.'
'Dominskiy, Dmitry I.'
'Lyssenko, Konstantin A.'
'Parashchuk, Olga D.'
'Trukhanov, Vasily A.'
'Konstantinov, Vladislav G.'
'Dubinets, Nikita O.'
'Paraschuk, Dmitry Yu'
_publ_section_title
;
 Structure and properties of naphthalene-diimide N-functionalized
 with stilbene.
;
_journal_issue                   29
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              19562
_journal_page_last               19575
_journal_paper_doi               10.1039/d3cp01582c
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C42 H26 N2 O4'
_chemical_formula_sum            'C42 H26 N2 O4'
_chemical_formula_weight         622.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-02-09 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.390(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.526(6)
_cell_length_b                   5.3037(18)
_cell_length_c                   23.743(6)
_cell_measurement_reflns_used    1524
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.32
_cell_measurement_theta_min      3.2
_cell_volume                     2879.4(14)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            13613
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.995
_diffrn_reflns_theta_min         1.915
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1533 before and 0.0675 after correction.
The Ratio of minimum to maximum transmission is 0.8492.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   0.979
_exptl_transmission_factor_min   0.961
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0596
_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)+(0.0702P)²+1.7715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1677
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2703
_reflns_number_total             3816
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cp01582c2.cif
_cod_data_source_block           a_a
_cod_depositor_comments          'Adding full bibliography for 7246944.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7246944
_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   0.971
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.49805(6) 0.1467(3) 0.65682(6) 0.0253(3) Uani 1 1 d . . . . .
N1 N 0.43882(6) 0.4794(3) 0.60724(7) 0.0191(3) Uani 1 1 d . . . . .
C1 C 0.50804(7) 0.3143(3) 0.56991(8) 0.0186(3) Uani 1 1 d . . . . .
O2 O 0.38055(5) 0.8136(3) 0.55717(6) 0.0252(3) Uani 1 1 d . . . . .
C2 C 0.55177(8) 0.1498(4) 0.57570(8) 0.0226(4) Uani 1 1 d . . . . .
C3 C 0.57612(8) 0.1589(4) 0.53311(9) 0.0239(4) Uani 1 1 d . . . . .
C4 C 0.55651(7) 0.3312(3) 0.48498(8) 0.0190(4) Uani 1 1 d . . . . .
C5 C 0.51224(7) 0.5045(3) 0.47843(7) 0.0167(3) Uani 1 1 d . . . . .
C6 C 0.48219(7) 0.3010(3) 0.61496(8) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.41761(7) 0.6650(3) 0.56016(8) 0.0194(4) Uani 1 1 d . . . . .
C8 C 0.41663(7) 0.4829(3) 0.65393(8) 0.0189(4) Uani 1 1 d . . . . .
C9 C 0.38028(8) 0.2920(4) 0.65553(8) 0.0215(4) Uani 1 1 d . . . . .
C10 C 0.35975(8) 0.3004(4) 0.70091(8) 0.0212(4) Uani 1 1 d . . . . .
C11 C 0.37582(7) 0.4978(3) 0.74463(8) 0.0202(4) Uani 1 1 d . . . . .
C12 C 0.41249(8) 0.6862(4) 0.74148(8) 0.0217(4) Uani 1 1 d . . . . .
C13 C 0.43263(8) 0.6808(4) 0.69590(8) 0.0218(4) Uani 1 1 d . . . . .
C14 C 0.35537(8) 0.5219(4) 0.79318(8) 0.0223(4) Uani 1 1 d . . . . .
C15 C 0.31619(8) 0.3817(4) 0.80181(8) 0.0228(4) Uani 1 1 d . . . . .
C16 C 0.29704(7) 0.4236(4) 0.85105(8) 0.0210(4) Uani 1 1 d . . . . .
C17 C 0.31637(9) 0.6266(4) 0.89303(10) 0.0316(5) Uani 1 1 d . . . . .
C18 C 0.29801(9) 0.6572(4) 0.93944(10) 0.0308(5) Uani 1 1 d . . . . .
C19 C 0.25892(8) 0.4876(4) 0.94427(9) 0.0254(4) Uani 1 1 d . . . . .
C20 C 0.23861(9) 0.2883(4) 0.90288(9) 0.0278(4) Uani 1 1 d . . . . .
C21 C 0.25788(8) 0.2554(4) 0.85704(9) 0.0250(4) Uani 1 1 d . . . . .
H2 H 0.5668(8) 0.033(4) 0.6111(9) 0.026(5) Uiso 1 1 d . . . . .
H9 H 0.3699(9) 0.154(4) 0.6249(10) 0.026(5) Uiso 1 1 d . . . . .
H10 H 0.3343(9) 0.163(4) 0.7013(9) 0.023(5) Uiso 1 1 d . . . . .
H12 H 0.4238(9) 0.828(4) 0.7720(10) 0.030(6) Uiso 1 1 d . . . . .
H19 H 0.2444(9) 0.513(4) 0.9747(9) 0.028(6) Uiso 1 1 d . . . . .
H3 H 0.6073(9) 0.050(4) 0.5386(10) 0.028(6) Uiso 1 1 d . . . . .
H21 H 0.2434(9) 0.121(4) 0.8274(9) 0.026(5) Uiso 1 1 d . . . . .
H13 H 0.4564(9) 0.815(4) 0.6931(9) 0.021(5) Uiso 1 1 d . . . . .
H14 H 0.3744(9) 0.662(4) 0.8224(10) 0.030(6) Uiso 1 1 d . . . . .
H15 H 0.2982(10) 0.237(5) 0.7746(11) 0.035(6) Uiso 1 1 d . . . . .
H18 H 0.3113(11) 0.796(6) 0.9674(12) 0.052(8) Uiso 1 1 d . . . . .
H20 H 0.2113(11) 0.168(5) 0.9055(11) 0.043(7) Uiso 1 1 d . . . . .
H17 H 0.3431(10) 0.747(5) 0.8892(10) 0.037(6) Uiso 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'
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'
H H 0.0000 0.0000 '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
C6 N1 C7 125.33(14) . . ?
C6 N1 C8 117.46(14) . . ?
C7 N1 C8 117.10(14) . . ?
C2 C1 C5 120.18(16) . 5_666 ?
C2 C1 C6 119.89(16) . . ?
C5 C1 C6 119.93(15) 5_666 . ?
C1 C2 C3 120.40(17) . . ?
C1 C2 H2 118.7(11) . . ?
C3 C2 H2 120.8(11) . . ?
C4 C3 C2 120.57(16) . . ?
C4 C3 H3 119.7(13) . . ?
C2 C3 H3 119.7(13) . . ?
C3 C4 C5 120.23(15) . . ?
C3 C4 C7 119.62(15) . 5_666 ?
C5 C4 C7 120.15(15) . 5_666 ?
C4 C5 C1 121.40(15) . 5_666 ?
C4 C5 C5 119.14(19) . 5_666 ?
C1 C5 C5 119.46(19) 5_666 5_666 ?
O1 C6 N1 121.29(15) . . ?
O1 C6 C1 121.95(15) . . ?
N1 C6 C1 116.75(14) . . ?
O2 C7 N1 121.21(15) . . ?
O2 C7 C4 122.37(16) . 5_666 ?
N1 C7 C4 116.42(14) . 5_666 ?
C9 C8 C13 121.58(16) . . ?
C9 C8 N1 120.34(15) . . ?
C13 C8 N1 118.08(15) . . ?
C8 C9 C10 119.01(17) . . ?
C8 C9 H9 119.3(12) . . ?
C10 C9 H9 121.7(12) . . ?
C9 C10 C11 120.67(16) . . ?
C9 C10 H10 117.6(12) . . ?
C11 C10 H10 121.8(12) . . ?
C12 C11 C10 118.57(15) . . ?
C12 C11 C14 117.49(16) . . ?
C10 C11 C14 123.92(16) . . ?
C13 C12 C11 121.13(17) . . ?
C13 C12 H12 119.7(12) . . ?
C11 C12 H12 119.2(12) . . ?
C8 C13 C12 119.03(17) . . ?
C8 C13 H13 120.6(12) . . ?
C12 C13 H13 120.3(12) . . ?
C15 C14 C11 128.69(18) . . ?
C15 C14 H14 118.7(12) . . ?
C11 C14 H14 112.6(12) . . ?
C14 C15 C16 125.09(18) . . ?
C14 C15 H15 120.0(13) . . ?
C16 C15 H15 114.9(13) . . ?
C17 C16 C21 117.50(16) . . ?
C17 C16 C15 123.08(17) . . ?
C21 C16 C15 119.42(17) . . ?
C16 C17 C18 121.33(18) . . ?
C16 C17 H17 118.8(13) . . ?
C18 C17 H17 119.9(14) . . ?
C19 C18 C17 120.01(19) . . ?
C19 C18 H18 119.5(15) . . ?
C17 C18 H18 120.4(16) . . ?
C20 C19 C18 119.71(17) . . ?
C20 C19 H19 119.8(14) . . ?
C18 C19 H19 120.4(14) . . ?
C19 C20 C21 120.18(18) . . ?
C19 C20 H20 120.9(14) . . ?
C21 C20 H20 118.9(14) . . ?
C20 C21 C16 121.25(18) . . ?
C20 C21 H21 121.1(12) . . ?
C16 C21 H21 117.6(12) . . ?
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
O1 C6 1.210(2) . ?
N1 C6 1.405(2) . ?
N1 C7 1.405(2) . ?
N1 C8 1.452(2) . ?
C1 C2 1.375(2) . ?
C1 C5 1.407(2) 5_666 ?
C1 C6 1.487(2) . ?
O2 C7 1.209(2) . ?
C2 C3 1.404(2) . ?
C2 H2 0.98(2) . ?
C3 C4 1.372(2) . ?
C3 H3 0.94(2) . ?
C4 C5 1.411(2) . ?
C4 C7 1.488(2) 5_666 ?
C5 C5 1.418(3) 5_666 ?
C8 C9 1.385(2) . ?
C8 C13 1.378(3) . ?
C9 C10 1.393(2) . ?
C9 H9 0.98(2) . ?
C10 C11 1.401(2) . ?
C10 H10 0.98(2) . ?
C11 C12 1.394(2) . ?
C11 C14 1.467(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.99(2) . ?
C13 H13 0.96(2) . ?
C14 C15 1.333(2) . ?
C14 H14 0.98(2) . ?
C15 C16 1.471(2) . ?
C15 H15 0.98(2) . ?
C16 C17 1.399(3) . ?
C16 C21 1.394(3) . ?
C17 C18 1.386(3) . ?
C17 H17 0.97(2) . ?
C18 C19 1.386(3) . ?
C18 H18 0.95(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.96(2) . ?
C20 C21 1.390(2) . ?
C20 H20 0.97(3) . ?
C21 H21 0.95(2) . ?
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
_geom_torsion_publ_flag
C5 C1 C2 C3 -0.7(3) 5_666 . . . ?
C6 C1 C2 C3 179.41(17) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C2 C3 C4 C7 -179.11(17) . . . 5_666 ?
C3 C4 C5 C1 179.01(17) . . . 5_666 ?
C7 C4 C5 C1 -0.7(3) 5_666 . . 5_666 ?
C3 C4 C5 C5 -1.0(3) . . . 5_666 ?
C7 C4 C5 C5 179.27(18) 5_666 . . 5_666 ?
C7 N1 C6 O1 -179.91(17) . . . . ?
C8 N1 C6 O1 4.1(2) . . . . ?
C7 N1 C6 C1 1.0(2) . . . . ?
C8 N1 C6 C1 -174.95(14) . . . . ?
C2 C1 C6 O1 -0.8(3) . . . . ?
C5 C1 C6 O1 179.36(17) 5_666 . . . ?
C2 C1 C6 N1 178.31(16) . . . . ?
C5 C1 C6 N1 -1.6(2) 5_666 . . . ?
C6 N1 C7 O2 -179.20(16) . . . . ?
C8 N1 C7 O2 -3.2(2) . . . . ?
C6 N1 C7 C4 0.4(2) . . . 5_666 ?
C8 N1 C7 C4 176.36(14) . . . 5_666 ?
C6 N1 C8 C9 -72.5(2) . . . . ?
C7 N1 C8 C9 111.20(19) . . . . ?
C6 N1 C8 C13 107.72(19) . . . . ?
C7 N1 C8 C13 -68.6(2) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
N1 C8 C9 C10 179.92(15) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C9 C10 C11 C14 179.06(17) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C14 C11 C12 C13 -178.39(16) . . . . ?
C9 C8 C13 C12 1.1(3) . . . . ?
N1 C8 C13 C12 -179.18(15) . . . . ?
C11 C12 C13 C8 -1.1(3) . . . . ?
C12 C11 C14 C15 173.01(19) . . . . ?
C10 C11 C14 C15 -5.7(3) . . . . ?
C11 C14 C15 C16 -178.30(18) . . . . ?
C14 C15 C16 C17 3.1(3) . . . . ?
C14 C15 C16 C21 -176.78(19) . . . . ?
C21 C16 C17 C18 1.0(3) . . . . ?
C15 C16 C17 C18 -178.96(19) . . . . ?
C16 C17 C18 C19 -1.2(3) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C19 C20 C21 C16 -1.1(3) . . . . ?
C17 C16 C21 C20 0.2(3) . . . . ?
C15 C16 C21 C20 -179.90(18) . . . . ?
