#------------------------------------------------------------------------------
#$Date: 2025-10-28 15:23:03 +0200 (Tue, 28 Oct 2025) $
#$Revision: 303063 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/11/7251129.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_7251129
loop_
_publ_author_name
'Femina, C.'
'Yamamoto, Norifumi'
'Ramya, N. K.'
'Sajith, Pookkottu K.'
'Thomas, Reji'
_publ_section_title
;
 Photophysical Divergence Driven by π-Spacer Variations in
 Anthracene-Cyanostilbene Architecture
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D5CP03033A
_journal_year                    2025
_chemical_compound_source        No
_chemical_formula_moiety         'C60 H60 N2 O2'
_chemical_formula_sum            'C60 H60 N2 O2'
_chemical_formula_weight         841.10
_chemical_name_systematic
(2Z,2'Z)-3,3'-(anthracene-9,10-diylbis(4,1-phenylene))bis(2-(4-(octyloxy)phenyl)acrylonitrile)
_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
_audit_update_record
;
2025-01-16 deposited with the CCDC.	2025-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                91.253(8)
_cell_angle_beta                 95.768(8)
_cell_angle_gamma                96.982(8)
_cell_formula_units_Z            1
_cell_length_a                   6.388(2)
_cell_length_b                   7.282(2)
_cell_length_c                   26.451(9)
_cell_measurement_reflns_used    2339
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.19
_cell_measurement_theta_min      2.32
_cell_volume                     1214.4(7)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker KAPPA 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  0.0858
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            25783
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.323
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_meas      1.151
_exptl_crystal_density_method    none
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             450
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate-hexane mixture'
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.016(3)
_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   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4286
_refine_ls_number_restraints     53
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0607
_refine_ls_shift/su_max          0.056
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0602P)²+0.5179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1679
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2349
_reflns_number_total             4286
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cp03033a2.cif
_cod_data_source_block           shelx
_cod_database_code               7251129
_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   0.993
_shelx_estimated_absorpt_t_max   0.997
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 0.3361(4) -0.4898(3) 0.46098(9) 0.0325(6) Uani 1 1 d . . . . .
C2 C 0.1666(4) -0.4907(3) 0.42135(10) 0.0410(7) Uani 1 1 d . . . . .
H2 H 0.179475 -0.405461 0.395829 0.049 Uiso 1 1 calc R U . . .
C3 C -0.0120(4) -0.6121(3) 0.41991(11) 0.0444(7) Uani 1 1 d . . . . .
H3 H -0.120089 -0.608782 0.393740 0.053 Uiso 1 1 calc R U . . .
C4 C -0.0349(4) -0.7434(3) 0.45790(11) 0.0439(7) Uani 1 1 d . . . . .
H4 H -0.159632 -0.824466 0.457130 0.053 Uiso 1 1 calc R U . . .
C5 C 0.1222(4) -0.7526(3) 0.49527(10) 0.0391(7) Uani 1 1 d . . . . .
H5 H 0.105430 -0.842284 0.519517 0.047 Uiso 1 1 calc R U . . .
C6 C 0.3142(4) -0.6279(3) 0.49864(10) 0.0328(6) Uani 1 1 d . . . . .
C7 C 0.5209(4) -0.3626(3) 0.46287(10) 0.0338(6) Uani 1 1 d . . . . .
C8 C 0.5313(4) -0.2107(3) 0.42577(9) 0.0342(6) Uani 1 1 d . . . . .
C9 C 0.6637(4) -0.1990(4) 0.38757(11) 0.0455(7) Uani 1 1 d . . . . .
H9 H 0.753151 -0.289338 0.384399 0.055 Uiso 1 1 calc R U . . .
C10 C 0.6668(4) -0.0563(4) 0.35383(10) 0.0465(7) Uani 1 1 d . . . . .
H10 H 0.759625 -0.051158 0.328825 0.056 Uiso 1 1 calc R U . . .
C11 C 0.5323(4) 0.0800(3) 0.35688(10) 0.0395(7) Uani 1 1 d . . . . .
C12 C 0.3973(4) 0.0648(3) 0.39479(11) 0.0445(7) Uani 1 1 d . . . . .
H12 H 0.303465 0.151943 0.397306 0.053 Uiso 1 1 calc R U . . .
C13 C 0.3976(4) -0.0747(3) 0.42871(11) 0.0443(7) Uani 1 1 d . . . . .
H13 H 0.306887 -0.078481 0.454151 0.053 Uiso 1 1 calc R U . . .
C14 C 0.5216(4) 0.2392(4) 0.32472(10) 0.0452(7) Uani 1 1 d . . . . .
H14 H 0.401288 0.297788 0.327120 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6515(4) 0.3176(4) 0.29236(10) 0.0453(7) Uani 1 1 d . . . . .
C16 C 0.8439(5) 0.2440(4) 0.28437(12) 0.0553(8) Uani 1 1 d . . . . .
C17 C 0.6165(5) 0.4894(4) 0.26487(11) 0.0476(7) Uani 1 1 d . . . . .
C18 C 0.7755(5) 0.5899(4) 0.24195(13) 0.0684(10) Uani 1 1 d . . . . .
H18 H 0.907958 0.548502 0.243218 0.082 Uiso 1 1 calc R U . . .
C19 C 0.7431(6) 0.7505(5) 0.21714(14) 0.0759(11) Uani 1 1 d . . . . .
H19 H 0.854534 0.816080 0.202527 0.091 Uiso 1 1 calc R U . . .
C20 C 0.5516(5) 0.8140(4) 0.21373(12) 0.0578(8) Uani 1 1 d . . . . .
C21 C 0.3921(5) 0.7200(5) 0.23678(13) 0.0716(10) Uani 1 1 d . . . . .
H21 H 0.261087 0.763881 0.235861 0.086 Uiso 1 1 calc R U . . .
C22 C 0.4252(5) 0.5587(5) 0.26166(14) 0.0702(10) Uani 1 1 d . . . . .
H22 H 0.313681 0.495121 0.276709 0.084 Uiso 1 1 calc R U . . .
C23 C 0.3336(6) 1.0361(5) 0.18027(14) 0.0739(10) Uani 1 1 d D U . . .
H23A H 0.288532 1.070960 0.212707 0.089 Uiso 1 1 calc R U . . .
H23B H 0.230169 0.937740 0.164450 0.089 Uiso 1 1 calc R U . . .
C24 C 0.3468(6) 1.2001(5) 0.14669(14) 0.0827(11) Uani 1 1 d D U . . .
H24A H 0.394198 1.164591 0.114584 0.099 Uiso 1 1 calc R U . . .
H24B H 0.450667 1.297635 0.162763 0.099 Uiso 1 1 calc R U . . .
C25 C 0.1358(7) 1.2727(6) 0.13677(16) 0.0996(14) Uani 1 1 d D U . . .
H25A H 0.034387 1.174888 0.119935 0.119 Uiso 1 1 calc R U . . .
H25B H 0.086738 1.301552 0.169217 0.119 Uiso 1 1 calc R U . . .
C26 C 0.1358(8) 1.4402(6) 0.10528(17) 0.1125(16) Uani 1 1 d D U . . .
H26A H 0.233446 1.539092 0.122841 0.135 Uiso 1 1 calc R U . . .
H26B H 0.190759 1.412630 0.073464 0.135 Uiso 1 1 calc R U . . .
C27 C -0.0730(9) 1.5102(8) 0.0933(2) 0.1370(19) Uani 1 1 d D U . . .
H27A H -0.164921 1.408529 0.075397 0.164 Uiso 1 1 calc R U . A 1
H27B H -0.127830 1.526187 0.125793 0.164 Uiso 1 1 calc R U . A 1
N1 N 1.0001(5) 0.1908(4) 0.27780(12) 0.0796(9) Uani 1 1 d . . . . .
O1 O 0.5347(4) 0.9734(3) 0.18793(9) 0.0780(7) Uani 1 1 d . . . . .
C28 C -0.111(3) 1.670(3) 0.0661(9) 0.164(6) Uani 0.623(14) 1 d D U P B 1
H28A H -0.060345 1.650887 0.033232 0.197 Uiso 0.623(14) 1 calc R U P B 1
H28B H -0.013646 1.769865 0.083232 0.197 Uiso 0.623(14) 1 calc R U P B 1
C29 C -0.308(3) 1.747(3) 0.0549(10) 0.185(7) Uani 0.623(14) 1 d D U P B 1
H29A H -0.407824 1.654412 0.035634 0.222 Uiso 0.623(14) 1 calc R U P B 1
H29B H -0.364070 1.769890 0.086884 0.222 Uiso 0.623(14) 1 calc R U P B 1
C30 C -0.300(3) 1.9133(18) 0.0277(6) 0.257(9) Uani 0.623(14) 1 d D U P B 1
H30A H -0.439046 1.950743 0.022660 0.385 Uiso 0.623(14) 1 calc R U P B 1
H30B H -0.205329 2.008698 0.046775 0.385 Uiso 0.623(14) 1 calc R U P B 1
H30C H -0.249242 1.892798 -0.004663 0.385 Uiso 0.623(14) 1 calc R U P B 1
C28' C -0.028(3) 1.693(3) 0.0612(10) 0.105(7) Uani 0.377(14) 1 d D . P B 2
H28C H 0.089315 1.772990 0.079201 0.126 Uiso 0.377(14) 1 calc R U P B 2
H28D H 0.015608 1.656632 0.028726 0.126 Uiso 0.377(14) 1 calc R U P B 2
C29' C -0.205(3) 1.795(3) 0.0521(19) 0.249(19) Uani 0.377(14) 1 d D . P B 2
H29C H -0.189137 1.892546 0.078397 0.298 Uiso 0.377(14) 1 calc R U P B 2
H29D H -0.191068 1.856067 0.020100 0.298 Uiso 0.377(14) 1 calc R U P B 2
C30' C -0.415(3) 1.707(5) 0.050(2) 0.38(3) Uani 0.377(14) 1 d D . P B 2
H30D H -0.512087 1.796204 0.043614 0.567 Uiso 0.377(14) 1 calc R U P B 2
H30E H -0.438455 1.613468 0.023123 0.567 Uiso 0.377(14) 1 calc R U P B 2
H30F H -0.436512 1.650185 0.081799 0.567 Uiso 0.377(14) 1 calc R U P B 2
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
C7 C1 C2 122.0(2) . . ?
C7 C1 C6 120.5(2) . . ?
C2 C1 C6 117.5(2) . . ?
C3 C2 C1 121.9(2) . . ?
C2 C3 C4 120.2(3) . . ?
C5 C4 C3 120.5(3) . . ?
C4 C5 C6 121.6(2) . . ?
C7 C6 C5 122.0(2) 2_646 . ?
C7 C6 C1 119.8(2) 2_646 . ?
C5 C6 C1 118.2(2) . . ?
C6 C7 C1 119.7(2) 2_646 . ?
C6 C7 C8 121.0(2) 2_646 . ?
C1 C7 C8 119.1(2) . . ?
C9 C8 C13 117.4(2) . . ?
C9 C8 C7 123.7(2) . . ?
C13 C8 C7 118.9(2) . . ?
C8 C9 C10 121.7(3) . . ?
C9 C10 C11 120.8(3) . . ?
C12 C11 C10 117.0(2) . . ?
C12 C11 C14 116.4(2) . . ?
C10 C11 C14 126.6(3) . . ?
C13 C12 C11 122.0(3) . . ?
C12 C13 C8 121.1(3) . . ?
C15 C14 C11 132.5(3) . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 C17 123.9(3) . . ?
C16 C15 C17 115.3(2) . . ?
N1 C16 C15 177.9(3) . . ?
C22 C17 C18 116.1(3) . . ?
C22 C17 C15 122.0(3) . . ?
C18 C17 C15 121.9(3) . . ?
C17 C18 C19 121.7(3) . . ?
C20 C19 C18 121.0(3) . . ?
C19 C20 C21 118.8(3) . . ?
C19 C20 O1 116.7(3) . . ?
C21 C20 O1 124.5(3) . . ?
C20 C21 C22 120.0(3) . . ?
C17 C22 C21 122.4(3) . . ?
O1 C23 C24 109.2(3) . . ?
C23 C24 C25 111.7(3) . . ?
C26 C25 C24 115.4(4) . . ?
C27 C26 C25 116.4(4) . . ?
C28 C27 C26 126.7(9) . . ?
C26 C27 C28' 106.4(8) . . ?
C20 O1 C23 118.3(3) . . ?
C27 C28 C29 129.0(16) . . ?
C30 C29 C28 117.2(17) . . ?
C29' C28' C27 114.8(16) . . ?
C30' C29' C28' 120.8(19) . . ?
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 C7 1.405(3) . ?
C1 C2 1.429(3) . ?
C1 C6 1.436(3) . ?
C2 C3 1.353(3) . ?
C3 C4 1.408(4) . ?
C4 C5 1.345(4) . ?
C5 C6 1.428(3) . ?
C6 C7 1.399(3) 2_646 ?
C7 C8 1.495(3) . ?
C8 C9 1.379(3) . ?
C8 C13 1.389(3) . ?
C9 C10 1.384(3) . ?
C10 C11 1.396(4) . ?
C11 C12 1.384(4) . ?
C11 C14 1.457(3) . ?
C12 C13 1.370(3) . ?
C14 C15 1.340(4) . ?
C15 C16 1.432(4) . ?
C15 C17 1.490(4) . ?
C16 N1 1.141(4) . ?
C17 C22 1.374(4) . ?
C17 C18 1.377(4) . ?
C18 C19 1.381(4) . ?
C19 C20 1.355(4) . ?
C20 C21 1.361(4) . ?
C20 O1 1.370(3) . ?
C21 C22 1.387(4) . ?
C23 O1 1.412(4) . ?
C23 C24 1.503(4) . ?
C24 C25 1.508(5) . ?
C25 C26 1.492(5) . ?
C26 C27 1.492(6) . ?
C27 C28 1.415(15) . ?
C27 C28' 1.60(2) . ?
C28 C29 1.444(16) . ?
C29 C30 1.419(10) . ?
C28' C29' 1.434(17) . ?
C29' C30' 1.410(10) . ?
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
C7 C1 C2 C3 -179.3(2) . . . . ?
C6 C1 C2 C3 2.3(4) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
C4 C5 C6 C7 -179.4(2) . . . 2_646 ?
C4 C5 C6 C1 0.4(4) . . . . ?
C7 C1 C6 C7 -0.8(4) . . . 2_646 ?
C2 C1 C6 C7 177.6(2) . . . 2_646 ?
C7 C1 C6 C5 179.4(2) . . . . ?
C2 C1 C6 C5 -2.3(3) . . . . ?
C2 C1 C7 C6 -177.5(2) . . . 2_646 ?
C6 C1 C7 C6 0.8(4) . . . 2_646 ?
C2 C1 C7 C8 6.9(3) . . . . ?
C6 C1 C7 C8 -174.8(2) . . . . ?
C6 C7 C8 C9 72.2(3) 2_646 . . . ?
C1 C7 C8 C9 -112.2(3) . . . . ?
C6 C7 C8 C13 -109.3(3) 2_646 . . . ?
C1 C7 C8 C13 66.3(3) . . . . ?
C13 C8 C9 C10 1.0(4) . . . . ?
C7 C8 C9 C10 179.5(3) . . . . ?
C8 C9 C10 C11 -1.1(4) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C9 C10 C11 C14 178.7(3) . . . . ?
C10 C11 C12 C13 1.4(4) . . . . ?
C14 C11 C12 C13 -177.5(3) . . . . ?
C11 C12 C13 C8 -1.5(4) . . . . ?
C9 C8 C13 C12 0.3(4) . . . . ?
C7 C8 C13 C12 -178.3(2) . . . . ?
C12 C11 C14 C15 164.6(3) . . . . ?
C10 C11 C14 C15 -14.3(5) . . . . ?
C11 C14 C15 C16 -0.1(5) . . . . ?
C11 C14 C15 C17 -176.3(3) . . . . ?
C14 C15 C17 C22 -14.8(5) . . . . ?
C16 C15 C17 C22 168.7(3) . . . . ?
C14 C15 C17 C18 164.0(3) . . . . ?
C16 C15 C17 C18 -12.4(4) . . . . ?
C22 C17 C18 C19 -0.2(5) . . . . ?
C15 C17 C18 C19 -179.1(3) . . . . ?
C17 C18 C19 C20 -1.0(6) . . . . ?
C18 C19 C20 C21 2.2(6) . . . . ?
C18 C19 C20 O1 -179.4(3) . . . . ?
C19 C20 C21 C22 -2.2(6) . . . . ?
O1 C20 C21 C22 179.5(3) . . . . ?
C18 C17 C22 C21 0.1(5) . . . . ?
C15 C17 C22 C21 179.0(3) . . . . ?
C20 C21 C22 C17 1.1(6) . . . . ?
O1 C23 C24 C25 179.6(3) . . . . ?
C23 C24 C25 C26 177.8(3) . . . . ?
C24 C25 C26 C27 177.7(4) . . . . ?
C25 C26 C27 C28 177.2(13) . . . . ?
C25 C26 C27 C28' 178.1(10) . . . . ?
C19 C20 O1 C23 175.3(3) . . . . ?
C21 C20 O1 C23 -6.4(5) . . . . ?
C24 C23 O1 C20 -174.0(3) . . . . ?
C26 C27 C28 C29 -178(2) . . . . ?
C27 C28 C29 C30 178(2) . . . . ?
C26 C27 C28' C29' -172(2) . . . . ?
C27 C28' C29' C30' -27(6) . . . . ?
