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_7063997
_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         'C30 H21 S'
_chemical_formula_sum            'C27 H21 Cl N3 S0.5'
_chemical_formula_weight         438.95
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-17
_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                113.27(4)
_cell_angle_beta                 102.05(4)
_cell_angle_gamma                107.42(3)
_cell_formula_units_Z            2
_cell_length_a                   10.431(4)
_cell_length_b                   11.026(4)
_cell_length_c                   11.802(6)
_cell_measurement_reflns_used    2828
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.9330
_cell_measurement_theta_min      2.1940
_cell_volume                     1103.8(11)
_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 0.989
_diffrn_measured_fraction_theta_max 0.774
_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     73.00  99.00   0.50   25.21    --   20.00  54.00 134.19   52
  2  \w    -74.00 -33.00   0.50   25.21    --   20.00  54.00  90.00   82
  3  \w    -24.00  56.00   0.50   25.21    --   20.00  54.00  90.00  160
  4  \w    -73.00   4.00   0.50   25.21    --   20.00  54.00   0.00  154
  5  \w     21.00  77.00   0.50   25.21    --   20.00  54.00   0.00  112
  6  \w    -72.00  59.00   0.50   25.21    --   20.00  54.00-150.00  262
  7  \w     75.00 101.00   0.50   25.21    --   20.00  54.00-150.00   52
  8  \w    -72.00 -44.00   0.50   25.21    --   20.00  54.00 -90.00   56
  9  \w     49.00  76.00   0.50   25.21    --   20.00  54.00 -90.00   54
 10  \w    -73.00  54.00   0.50   25.21    --   20.00  54.00-180.00  254
 11  \w     64.00  89.00   0.50   25.21    --   20.00  54.00-180.00   50
 12  \w    -66.00   7.00   0.50   25.21    --   20.00  54.00 -61.50  146
 13  \w     61.00  86.00   0.50   25.21    --   20.00  54.00 -61.50   50
 14  \w    -22.00  50.00   0.50   25.21    --   20.00  54.00  60.00  144
 15  \w    -67.00 -40.00   0.50   25.21    --   20.00  54.00 -30.00   54
 16  \w     -7.00  19.00   0.50   25.21    --   20.00  54.00 -30.00   52
 17  \w     82.00 107.00   0.50   25.21    --   20.00  54.00 -30.00   50
 18  \w    -13.00  12.00   0.50   25.21    --   20.00  54.00 120.00   50
 19  \w     49.00  76.00   0.50   25.21    --   20.00  54.00 120.00   54
 20  \w    -68.00  47.00   0.50   25.21    --   20.00  54.00 134.19  230
;
_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      -0.0243433000
_diffrn_orient_matrix_UB_12      -0.0765685000
_diffrn_orient_matrix_UB_13      -0.0378406000
_diffrn_orient_matrix_UB_21      -0.0478226000
_diffrn_orient_matrix_UB_22      -0.0012448000
_diffrn_orient_matrix_UB_23      -0.0533252000
_diffrn_orient_matrix_UB_31      0.0549600000
_diffrn_orient_matrix_UB_32      0.0109578000
_diffrn_orient_matrix_UB_33      -0.0263919000
_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  0.1070
_diffrn_reflns_av_unetI/netI     0.1091
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.774
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15617
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.774
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.104
_diffrn_reflns_theta_min         2.025
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37018
_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    1.321
_exptl_crystal_F_000             458
_refine_diff_density_max         1.172
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.349
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         5988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.349
_refine_ls_R_factor_all          0.2744
_refine_ls_R_factor_gt           0.1672
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4112
_refine_ls_wR_factor_ref         0.4725
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2653
_reflns_number_total             5988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03137k2.cif
_cod_data_source_block           ot4a__auto
_cod_depositor_comments
'Adding full bibliography for 7063994--7063997.cif.'
_cod_original_cell_volume        1103.9(9)
_cod_original_formula_sum        'C27 H21 Cl N3 S0.50'
_cod_database_code               7063997
_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:
 C3(H3), C10(H10), C6(H6), C9(H9), C14(H14), C17(H17), C21(H21), C16(H16),
 C22(H22), C5(H5), C15(H15), C4(H4), C27(H27), C28(H28), C26(H26)
2.b Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              3772
_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 4.536
_oxdiff_exptl_absorpt_empirical_full_min 0.474