Asymmetric synthesis of complex tricyclo[3.2.2.0]nonenes from racemic norcaradienes: kinetic resolution <i>via</i> Diels-Alder reaction.
Wang, Siyuan; Zhou, Yuqiao; Xiao, Wanlong; Li, Zegong; Liu, Xiaohua; Feng, Xiaoming; Chemical science 14 (2023) 1844–1851; doi:10.1039/d2sc06490a

data_1568268
_publ_section_title
;
 Asymmetric synthesis of complex tricyclo[3.2.2.0]nonenes from racemic
 norcaradienes: kinetic resolution <i>via</i> Diels-Alder reaction.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              1844
_journal_page_last               1851
_journal_paper_doi               10.1039/d2sc06490a
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H30 O5'
_chemical_formula_sum            'C29 H30 O5'
_chemical_formula_weight         458.53
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-02 deposited with the CCDC.	2023-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.97020(10)
_cell_length_b                   9.97020(10)
_cell_length_c                   48.7176(12)
_cell_measurement_reflns_used    9409
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      3.63
_cell_volume                     4842.77(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_number            43923
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.358
_diffrn_reflns_theta_min         3.629
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  0.8731
_exptl_absorpt_correction_T_min  0.7085
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, PE'
_exptl_crystal_size_max          0.777
_exptl_crystal_size_mid          0.678
_exptl_crystal_size_min          0.348
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
; 
 Flack x determined using 1694 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       0.0048(2)
_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   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4386
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0310P)^2^+1.1658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0704
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4327
_reflns_number_total             4386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06490a2.cif
_cod_data_source_block           waf010
_cod_depositor_comments
'Adding full bibliography for 1568266--1568269.cif.'
_cod_original_cell_volume        4842.77(15)
_cod_database_code               1568268
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.618
_shelx_estimated_absorpt_t_max   0.796
_shelx_res_checksum              91015
_shelx_hkl_checksum              499