Reversing the stereoselectivity of intramolecular [2+2] photocycloaddition utilizing cucurbit[8]uril as a molecular flask.
Qiu, Xujun; Seibert, Jasmin; Fuhr, Olaf; Biedermann, Frank; Bräse, Stefan; Chemical communications (Cambridge, England) 60 (2024) 3267–3270; doi:10.1039/d3cc05783f

data_7132668
_publ_section_title
;
 Reversing the stereoselectivity of intramolecular [2+2]
 photocycloaddition utilizing cucurbit[8]uril as a molecular flask.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3267
_journal_page_last               3270
_journal_paper_doi               10.1039/d3cc05783f
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(Cl), 4(H2 O), C32 H26 N2'
_chemical_formula_sum            'C32 H34 Cl2 N2 O4'
_chemical_formula_weight         581.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2023-11-22 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2222(3)
_cell_length_b                   10.4342(4)
_cell_length_c                   27.3088(11)
_cell_measurement_reflns_used    30575
_cell_measurement_temperature    180
_cell_measurement_theta_max      64.27
_cell_measurement_theta_min      3.76
_cell_volume                     2912.77(18)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180
_diffrn_detector                 'Eiger R 4M'
_diffrn_detector_area_resol_mean 13.33
_diffrn_detector_type            DECTRIS
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34143
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            18886
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        53.597
_diffrn_reflns_theta_max         62.488
_diffrn_reflns_theta_min         3.946
_diffrn_source                   'Metaljet D2'
_diffrn_source_current           3.570
_diffrn_source_power             0.250
_diffrn_source_target            Ga
_diffrn_source_type              'Metaljet D2'
_diffrn_source_voltage           70
_exptl_absorpt_coefficient_mu    1.516
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.8021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.766
_refine_diff_density_min         -1.365
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 2708 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         6909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0692
_refine_ls_shift/su_max          1.790
_refine_ls_shift/su_mean         0.087
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0980P)^2^+4.0797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1833
_refine_ls_wR_factor_ref         0.1850
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                6647
_reflns_number_total             6909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05783f2.cif
_cod_data_source_block           xqr252
_cod_depositor_comments          'Adding full bibliography for 7132668.cif.'
_cod_database_code               7132668
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.851
_shelx_estimated_absorpt_t_min   0.805
_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 O(H,H) groups
2.a Free rotating group:
 O4(H4A,H4B)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11),
 C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23),
  C24(H24), C27(H27), C28(H28), C30(H30), C31(H31)
;
_shelx_res_checksum              72588
_shelx_hkl_checksum              15309
_olex2_submission_special_instructions 'No special instructions were received'