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_1559891
_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_absolute_configuration unk
_chemical_formula_moiety         'C26 H25 O'
_chemical_formula_sum            'C26 H25 O'
_chemical_formula_weight         353.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-05-31
_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                90
_cell_angle_beta                 99.029(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9345(13)
_cell_length_b                   7.2394(8)
_cell_length_c                   22.679(2)
_cell_measurement_reflns_used    1082
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3060
_cell_measurement_theta_min      3.4400
_cell_volume                     1935.2(4)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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   50.00   77.00   0.9000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       17.0762   57.0000  -60.0000 30

  2 omega    7.00   84.40   0.9000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       17.0762   57.0000 -180.0000 86

  3 omega    4.00   85.00   0.9000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       17.0762   77.0000 -120.0000 90

  4 omega  -34.00   11.90   0.9000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       17.0762  -57.0000 -180.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0345150000
_diffrn_orient_matrix_UB_12      0.0021096000
_diffrn_orient_matrix_UB_13      -0.0285062000
_diffrn_orient_matrix_UB_21      0.0493523000
_diffrn_orient_matrix_UB_22      0.0019311000
_diffrn_orient_matrix_UB_23      -0.0138082000
_diffrn_orient_matrix_UB_31      0.0002236000
_diffrn_orient_matrix_UB_32      -0.0978245000
_diffrn_orient_matrix_UB_33      -0.0008870000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4757
_diffrn_reflns_point_group_measured_fraction_full 0.804
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.957
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89035
_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    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 630 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3120
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0611P)^2^+0.2259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1344
_reflns_Friedel_coverage         0.463
_reflns_Friedel_fraction_full    0.574
_reflns_Friedel_fraction_max     0.545
_reflns_number_gt                2361
_reflns_number_total             3120
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05213b2.cif
_cod_data_source_block           190531_s1_htt_447_2a
_cod_depositor_comments
;Adding full bibliography for 1559890--1559892.cif.

 Adding full bibliography for 1559890--1559892.cif.
;
_cod_database_code               1559891
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3cl1
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.975
_reflns_odcompleteness_completeness 99.81
_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:
 C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C19(H19), C21(H21),
 C22(H22), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              33333
_olex2_date_sample_data_collection 2009-06-29
_olex2_submission_special_instructions 'No special instructions were received'