Tuning the photochromism of indeno-fused 2H-naphthopyrans using steric spirocyclic groups
Wei, Ruiqi; Zhou, Ruiyuan; Shen, Ripei; Han, Jie; New Journal of Chemistry 48 (2024) 15352–15357; doi:10.1039/D4NJ02706J

data_7063395
_publ_section_title
;
 Tuning the photochromism of indeno-fused 2H-naphthopyrans using steric
 spirocyclic groups
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15352
_journal_page_last               15357
_journal_paper_doi               10.1039/D4NJ02706J
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C54 H38 O3'
_chemical_formula_sum            'C54 H38 O3'
_chemical_formula_weight         734.84
_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             2024-06-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-06-06 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                88.277(2)
_cell_angle_beta                 72.382(2)
_cell_angle_gamma                71.540(2)
_cell_formula_units_Z            2
_cell_length_a                   11.6774(3)
_cell_length_b                   12.0992(3)
_cell_length_c                   14.8445(4)
_cell_measurement_reflns_used    17567
_cell_measurement_temperature    298(1)
_cell_measurement_theta_max      76.6130
_cell_measurement_theta_min      3.8140
_cell_volume                     1891.08(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.960
_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     19.00  92.00   0.50    0.05    --   47.40-125.00  30.00  146
  2  \w     46.00 110.00   0.50    0.05    --  105.91-125.00 -60.00  128
  3  \w     43.00 111.00   0.50    0.05    --  105.91-125.00 -30.00  136
  4  \w     19.00  84.00   0.50    0.05    --   47.40-125.00-150.00  130
  5  \w     69.00 112.00   0.50    0.05    --  105.91-125.00-180.00   86
  6  \w     74.00 101.00   0.50    0.05    --  105.91 -95.00 -60.00   54
  7  \w     68.00  94.00   0.50    0.05    --  105.91 -95.00 -30.00   52
  8  \w     42.00 108.00   0.50    0.05    --  105.91-125.00  90.00  132
  9  \w     34.00  93.00   0.50    0.05    --  105.91 -95.00   0.00  118
 10  \w     -5.00  24.00   0.50    0.05    --   47.40 -19.00-180.00   58
 11  \w     42.00  72.00   0.50    0.05    --  105.91 -61.00-180.00   60
 12  \w    -20.00  13.00   0.50    0.05    --   47.40 -61.00  -3.00   66
 13  \w     33.00  75.00   0.50    0.05    --  105.91 -61.00  -3.00   84
 14  \w     81.00 169.00   0.50    0.05    --  105.91 125.00   0.00  176
 15  \w     33.00 117.00   0.50    0.05    --   47.40  61.00 135.00  168
 16  \w    108.00 141.00   0.50    0.05    --  105.91  61.00 135.00   66
 17  \w     90.00 173.00   0.50    0.05    --  105.91  61.00  60.00  166
 18  \w    110.00 176.00   0.50    0.05    --  105.91  45.00   0.00  132
 19  \w     99.00 177.00   0.50    0.05    --  105.91  30.00 -30.00  156
 20  \w     94.00 177.00   0.50    0.05    --  105.91  45.00-180.00  166
 21  \w    -22.00  28.00   0.50    0.05    --  -47.40  19.00 120.00  100
 22  \w     -6.00  19.00   0.50    0.05    --  -47.40  61.00 135.00   50
 23  \w    -64.00 -20.00   0.50    0.05    --  -47.40  61.00 135.00   88
 24  \w   -100.00 -70.00   0.50    0.05    -- -104.50  77.00 150.00   60
 25  \w    -61.00 -35.00   0.50    0.05    -- -104.50  61.00 135.00   52
 26  \w    -68.00 -34.00   0.50    0.05    -- -104.50  61.00 120.00   68
 27  \w    -63.00 -38.00   0.50    0.05    -- -104.50  61.00   0.00   50
 28  \w    -61.00 -33.00   0.50    0.05    -- -104.50  61.00 -30.00   56
 29  \w    -63.00 -32.00   0.50    0.05    -- -104.50  61.00-120.00   62
 30  \w   -127.00-101.00   0.50    0.05    -- -104.50 146.00   0.50   52
 31  \w    -66.00 -36.00   0.50    0.05    -- -104.50 125.00  90.00   60
 32  \w    -99.00 -54.00   0.50    0.05    -- -104.50 125.00 150.00   90
 33  \w   -108.00 -38.00   0.50    0.05    -- -104.50 112.00 126.89  140
 34  \w   -171.00-107.00   0.50    0.05    -- -104.50 -45.00 -60.00  128
 35  \w   -168.00 -88.00   0.50    0.05    -- -104.50 -61.00  -3.00  160
 36  \w   -119.00 -32.00   0.50    0.05    --  -47.40 -61.00  -3.00  174
 37  \w   -172.00-146.00   0.50    0.05    -- -104.50-125.00  90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0486172000
_diffrn_orient_matrix_UB_12      0.0919745000
_diffrn_orient_matrix_UB_13      0.0315968000
_diffrn_orient_matrix_UB_21      0.0479772000
_diffrn_orient_matrix_UB_22      -0.0827294000
_diffrn_orient_matrix_UB_23      0.0712204000
_diffrn_orient_matrix_UB_31      0.1293199000
_diffrn_orient_matrix_UB_32      -0.0530221000
_diffrn_orient_matrix_UB_33      -0.0764780000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24115
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.678
_diffrn_reflns_theta_min         3.862
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0037(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         7655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0531P)^2^+0.5725P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6905
_reflns_number_total             7655
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02706j2.cif
_cod_data_source_block           p20231110d1_auto
_cod_depositor_comments          'Adding full bibliography for 7063395.cif.'
_cod_database_code               7063395
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C N O'
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.823
_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:
 C24(H24), C25(H25), C26(H26), C27(H27), C3(H3), C4(H4), C35(H35), C36(H36),
 C37(H37), C38(H38), C46(H46), C47(H47), C48(H48), C49(H49), C50(H50), C40(H40),
  C41(H41), C42(H42), C43(H43), C44(H44), C54(H54), C53(H53), C52(H52),
 C51(H51), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15), C18(H18),
 C19(H19)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              35
_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 1.916
_oxdiff_exptl_absorpt_empirical_full_min 0.589