Rapid access to bicyclic δ-lactones via carbene-catalyzed activation and cascade reaction of unsaturated carboxylic esters
Fu, Zhenqian; Wu, Xingxing; Chi, Yonggui Robin; Organic Chemistry Frontiers 3 (2016) 145–; doi:10.1039/C5QO00348B

data_1553207
_publ_section_title
;
 Rapid access to bicyclic \d-lactones via carbene-catalyzed activation and
 cascade reaction of unsaturated carboxylic esters
;
_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              145
_journal_paper_doi               10.1039/C5QO00348B
_journal_volume                  3
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C36 H29 Cl O6'
_chemical_formula_weight         593.04
_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   geom
_audit_update_record
;
2015-06-04 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2154(3)
_cell_length_b                   20.2473(13)
_cell_length_c                   22.9882(17)
_cell_measurement_reflns_used    1445
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      21.7907
_cell_measurement_theta_min      2.8422
_cell_volume                     2893.0(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4464
_diffrn_reflns_theta_full        29.29
_diffrn_reflns_theta_max         29.29
_diffrn_reflns_theta_min         3.15
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.298
_refine_ls_abs_structure_details
'No quotients, so Flack parameter determined by classical intensity fit'
_refine_ls_abs_structure_Flack   0.44(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         4464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+1.0074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1167
_reflns_number_gt                3394
_reflns_number_total             4464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00348b2.cif
_cod_data_source_block           I
_cod_database_code               1553207
_shelx_res_checksum              34185
_shelx_hkl_checksum              44386