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_7063996
_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         'C31 H23 N S'
_chemical_formula_sum            'C31 H23 N S'
_chemical_formula_weight         441.56
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-07-20
_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                 96.714(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.023(3)
_cell_length_b                   16.781(3)
_cell_length_c                   10.7881(17)
_cell_measurement_reflns_used    2797
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.3310
_cell_measurement_theta_min      2.0380
_cell_volume                     2341.5(8)
_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
'olex2.solve 1.5-ac6-020 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_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    -33.00  73.00   0.50   91.35    --   20.00  54.00 120.00  212
  2  \w     85.00 110.00   0.50   91.35    --   20.00  54.00 120.00   50
  3  \w    -73.00  64.00   0.50   91.35    --   20.00  54.00  30.00  274
  4  \w     67.00 106.00   0.50   91.35    --   20.00  54.00  30.00   78
  5  \w    -74.00 109.00   0.50   91.35    --   20.00  54.00 -30.00  366
  6  \w    -28.00  13.00   0.50   91.35    --   20.00  54.00  90.00   82
  7  \w     70.00  95.00   0.50   91.35    --   20.00  54.00  90.00   50
  8  \w    -52.00 -27.00   0.50   91.35    --   20.00  54.00-150.00   50
  9  \w    -16.00   9.00   0.50   91.35    --   20.00  54.00-150.00   50
 10  \w     75.00 102.00   0.50   91.35    --   20.00  54.00-150.00   54
 11  \w      9.00  34.00   0.50   91.35    --   20.00  54.00 -60.00   50
 12  \w    -65.00 -40.00   0.50   91.35    --   20.00  54.00 120.00   50
;
_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      0.0040796000
_diffrn_orient_matrix_UB_12      -0.0017392000
_diffrn_orient_matrix_UB_13      -0.0539248000
_diffrn_orient_matrix_UB_21      -0.0648681000
_diffrn_orient_matrix_UB_22      -0.0081215000
_diffrn_orient_matrix_UB_23      -0.0091465000
_diffrn_orient_matrix_UB_31      -0.0125641000
_diffrn_orient_matrix_UB_32      0.0414484000
_diffrn_orient_matrix_UB_33      -0.0039623000
_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  0.0699
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23800
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.049
_diffrn_reflns_theta_min         1.574
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59898
_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    1.253
_exptl_crystal_F_000             928
_refine_diff_density_max         3.289
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         6539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      3.967
_refine_ls_R_factor_all          0.6013
_refine_ls_R_factor_gt           0.4705
_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/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.7991
_refine_ls_wR_factor_ref         0.8406
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1680
_reflns_number_total             6539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03137k2.cif
_cod_data_source_block           2a-ot-_auto
_cod_depositor_comments
'Adding full bibliography for 7063994--7063997.cif.'
_cod_original_cell_volume        2341.4(7)
_cod_database_code               7063996
_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:
 C26(H26), C7(H7), C14(H14), C20(H20), C30(H30), C24(H24), C16(H16), C9(H9),
 C10(H10), C13(H13), C22(H22), C17(H17), C33(H33), C3(H3), C18(H18), C19(H19),
 C23(H23)
2.b Fitted pentagon refined as free rotating group:
 S2(C4,N1,C27,C28)
2.c Fitted hexagon refined as free rotating group:
 C33(C12,C3,C18,C19,C23)
2.d Naphthalene refined as free rotating group:
 C26(C7,C14,C20,C5,C8,C15,C30,C24,C21), C29(C16,C9,C11,C6,C25,C10,C13,C22,C17)
2.e Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              98096
_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 1.723
_oxdiff_exptl_absorpt_empirical_full_min 0.680