Trace mild acid-catalysed <i>Z</i> → <i>E</i> isomerization of norbornene-fused stilbene derivatives: intelligent chiral molecular photoswitches with controllable self-recovery.
Hao, Taotao; Yang, Yongsheng; Liang, Wenting; Fan, Chunying; Wang, Xin; Wu, Wanhua; Chen, Xiaochuan; Fu, Haiyan; Chen, Hua; Yang, Cheng; Chemical science 12 (2020) 2614–2622; doi:10.1039/d0sc05213b

data_1559892
_publ_section_title
;
 Trace mild acid-catalysed <i>Z</i> \\rightarrow <i>E</i> isomerization of
 norbornene-fused stilbene derivatives: intelligent chiral molecular
 photoswitches with controllable self-recovery.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              2614
_journal_page_last               2622
_journal_paper_doi               10.1039/d0sc05213b
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C23 H24 O'
_chemical_formula_sum            'C23 H24 O'
_chemical_formula_weight         316.42
_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     direct
_audit_creation_date             2018-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-28 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                111.746(7)
_cell_angle_beta                 114.773(7)
_cell_angle_gamma                91.316(5)
_cell_formula_units_Z            2
_cell_length_a                   9.4684(6)
_cell_length_b                   10.1128(6)
_cell_length_c                   11.1589(9)
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5090
_cell_measurement_theta_min      3.5540
_cell_volume                     880.77(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -2.00   86.00   1.0000    6.6400
omega____ theta____ kappa____ phi______ frames
    -       16.8419   38.0000  -90.0000 88

  2 omega   -7.00   79.00   1.0000    6.6400
omega____ theta____ kappa____ phi______ frames
    -       16.8419   77.0000   30.0000 86

  3 omega  -23.00   86.00   1.0000    6.6400
omega____ theta____ kappa____ phi______ frames
    -       16.8419    0.0000 -150.0000 109

  4 omega  -15.00   18.00   1.0000    6.6400
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -90.0000 33

  5 omega  -42.00    1.00   1.0000    6.6400
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000  120.0000 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0338288000
_diffrn_orient_matrix_UB_12      0.0150916000
_diffrn_orient_matrix_UB_13      -0.0622757000
_diffrn_orient_matrix_UB_21      0.0426874000
_diffrn_orient_matrix_UB_22      0.0732886000
_diffrn_orient_matrix_UB_23      0.0430038000
_diffrn_orient_matrix_UB_31      0.0644867000
_diffrn_orient_matrix_UB_32      -0.0192282000
_diffrn_orient_matrix_UB_33      -0.0146763000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6849
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.986
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0552P)^2^+0.1526P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1276
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2636
_reflns_number_total             3587
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05213b2.cif
_cod_data_source_block           exp_3112
_cod_depositor_comments
;Adding full bibliography for 1559890--1559892.cif.

 Adding full bibliography for 1559890--1559892.cif.
;
_cod_original_cell_volume        880.77(12)
_cod_database_code               1559892
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              46261
_olex2_submission_special_instructions 'No special instructions were received'