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_1559890
_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 ad
_chemical_formula_moiety         'C22 H31 N2 O2 S, C4 H3 O4'
_chemical_formula_sum            'C26 H34 N2 O6 S'
_chemical_formula_weight         502.61
_chemical_name_systematic
;
(E)-4-hydroxy-4-oxo-but-2-enoate; (3-methoxy-2-thienyl)methyl-
[2-[(7R)-7-(2-pyridyl)-10-oxaspiro[4.5]decan-7-yl]ethyl]ammonium
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc10wfht
_audit_creation_date             2011-09-08
_audit_creation_method
;
  Olex2 1.1
  (compiled Sep  7 2011 21:07:27, GUI svn.r3853)
;
_audit_update_record
;
2013-07-11 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.951(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.2203(4)
_cell_length_b                   17.3233(9)
_cell_length_c                   11.9123(6)
_cell_measurement_reflns_used    3631
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.30
_cell_measurement_theta_min      6.32
_cell_volume                     1281.92(12)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XM, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'MX Optics'
_diffrn_radiation_source         microsource
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7958
_diffrn_reflns_theta_full        64.54
_diffrn_reflns_theta_max         64.54
_diffrn_reflns_theta_min         6.32
_diffrn_source_current           0.64
_diffrn_source_power             0.0285824
_diffrn_source_voltage           44.66
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.482
_exptl_absorpt_correction_T_max  0.7525
_exptl_absorpt_correction_T_min  0.6489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.0940 before and 0.0457 after correction.
The Ratio of minimum to maximum transmission is 0.8623.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4085
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1186P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1715
_reflns_number_gt                3491
_reflns_number_total             4085
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0sc05213b2.cif
_cod_data_source_block           n1290
_cod_depositor_comments
;Adding full bibliography for 1559890--1559892.cif.

 Adding full bibliography for 1559890--1559892.cif.
;
_cod_database_code               1559890
_local_nu_authors                'Dr. Amy A. Sarjeant'
_local_nu_crystal_method         'slow evaporation'
_local_nu_crystal_solvent        'methanol, t-butyl methylester'
_local_nu_labbook_chem           unknown
_local_nu_labbook_crystalization none
_local_nu_labbook_xray           NUTREV1_003
_local_nu_project_code           none
_local_nu_project_name           unknown
_local_nu_quality_factor         2
_local_nu_refine_ls_disord_occ   n.a.
_local_nu_refine_ls_disord_u     n.a.
_local_nu_refine_ls_disord_xyz   n.a.
_local_nu_refine_ls_h_carbon_u   riding
_local_nu_refine_ls_h_carbon_xyz riding
_local_nu_refine_ls_h_hetero_u   'freely refined'
_local_nu_refine_ls_h_hetero_xyz 'freely refined'
_local_nu_refine_ls_nonh_u       anisotropic
_local_nu_refine_ls_nonh_xyz     'freely refined'
_local_nunumber                  DC-0068-027C
_local_xraynumber                n1290