Synthesis and photochromic modulation of aromaticity in dinaphthylethene derivatives
Ou, Tao; Kong, Lingxu; Song, Changsen; Shang, Bingyan; Yang, Jingjing; Zuo, Jinxin; Di, Feifan; Yan, Maocai; Ding, Lin; Li, Ruiji; New Journal of Chemistry 49 (2025) 17841–17848; doi:10.1039/D5NJ03137K

data_7063995
_publ_section_title
;
 Synthesis and photochromic modulation of aromaticity in dinaphthylethene
 derivatives
;
_journal_issue                   41
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17841
_journal_page_last               17848
_journal_paper_doi               10.1039/D5NJ03137K
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         '3(C30 H22 S)'
_chemical_formula_sum            'C90 H66 S3'
_chemical_formula_weight         1243.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-31
_audit_creation_method
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_audit_update_record
;
2025-08-03 deposited with the CCDC.	2025-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.132(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5526(8)
_cell_length_b                   30.640(2)
_cell_length_c                   11.7643(10)
_cell_measurement_reflns_used    4976
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.8890
_cell_measurement_theta_min      2.2020
_cell_volume                     3323.9(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -3.00  49.00   0.50   12.57    --   20.00  54.00 -90.00  104
  2  \w     59.00 100.00   0.50   12.57    --   20.00  54.00 -90.00   82
  3  \w    -73.00  69.00   0.50   12.57    --   20.00  54.00  30.00  284
  4  \w     72.00 107.00   0.50   12.57    --   20.00  54.00  30.00   70
  5  \w    -74.00  52.00   0.50   12.57    --   20.00  54.00 150.00  252
  6  \w     67.00  98.00   0.50   12.57    --   20.00  54.00 150.00   62
  7  \w    -73.00  12.00   0.50   12.57    --   20.00  54.00 -30.00  170
  8  \w     61.00  87.00   0.50   12.57    --   20.00  54.00 -30.00   52
  9  \w     13.00  38.00   0.50   12.57    --   20.00  54.00  90.00   50
 10  \w     75.00 100.00   0.50   12.57    --   20.00  54.00  90.00   50
 11  \w    -20.00   5.00   0.50   12.57    --   20.00  54.00-180.00   50
 12  \w     62.00  87.00   0.50   12.57    --   20.00  54.00-180.00   50
 13  \w    -64.00  71.00   0.50   12.57    --   20.00  54.00  60.00  270
 14  \w    -70.00 -37.00   0.50   12.57    --   20.00  54.00-150.00   66
 15  \w     46.00  71.00   0.50   12.57    --   20.00  54.00-150.00   50
 16  \w     77.00 102.00   0.50   12.57    --   20.00  54.00-150.00   50
 17  \w    -65.00  31.00   0.50   12.57    --   20.00  54.00 163.80  192
 18  \w    -62.00 -17.00   0.50   12.57    --   20.00  54.00-120.00   90
 19  \w     46.00  73.00   0.50   12.57    --   20.00  54.00-120.00   54
 20  \w    -68.00  46.00   0.50   12.57    --   20.00  54.00   0.00  228
 21  \w     75.00 100.00   0.50   12.57    --   20.00  54.00   0.00   50
 22  \w    -69.00 -43.00   0.50   12.57    --   20.00  54.00 120.00   52
 23  \w      7.00  35.00   0.50   12.57    --   20.00  54.00 120.00   56
 24  \w    -68.00 -41.00   0.50   12.57    --   20.00  54.00 -90.00   54
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0531548000
_diffrn_orient_matrix_UB_12      -0.0166774000
_diffrn_orient_matrix_UB_13      -0.0078251000
_diffrn_orient_matrix_UB_21      0.0478596000
_diffrn_orient_matrix_UB_22      -0.0128013000
_diffrn_orient_matrix_UB_23      0.0435565000
_diffrn_orient_matrix_UB_31      -0.0282247000
_diffrn_orient_matrix_UB_32      0.0097100000
_diffrn_orient_matrix_UB_33      0.0440840000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.1343
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            67939
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.024
_diffrn_reflns_theta_min         1.793
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.141a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             1308
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1234 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     844
_refine_ls_number_reflns         18250
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.2780
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.225
_refine_ls_shift/su_mean         0.045
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0673P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.2052
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                4015
_reflns_number_total             18250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03137k2.cif
_cod_data_source_block           3a-ot__auto
_cod_depositor_comments
'Adding full bibliography for 7063994--7063997.cif.'
_cod_database_code               7063995
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C59(H59), C28(H28), C90(H90), C26(H26), C88(H88), C3(H3), C77(H77), C10(H10),
 C41(H41), C57(H57), C45(H45), C54(H54), C15(H15), C21(H21), C87(H87), C65(H65),
  C24(H24), C25(H25), C17(H17), C46(H46), C76(H76), C7(H7), C39(H39), C52(H52),
 C14(H14), C34(H34), C8(H8), C5(H5), C23(H23), C83(H83), C69(H69), C72(H72),
 C36(H36), C68(H68), C67(H67), C70(H70), C56(H56), C6(H6), C38(H38), C48(H48),
 C16(H16), C55(H55), C78(H78), C86(H86), C47(H47), C37(H37), C79(H79), C85(H85)
2.b Idealised Me refined as rotating group:
 C92(H92A,H92B,H92C), C62(H62A,H62B,H62C), C31(H31A,H31B,H31C), C61(H61A,H61B,
 H61C), C30(H30A,H30B,H30C), C93(H93A,H93B,H93C)
;
_shelx_res_checksum              87014
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.171
_oxdiff_exptl_absorpt_empirical_full_min 0.899