Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates with benzofuranone-derived olefins for a highly regio-, diastereo- and enantioselective synthesis of spiro-benzofuranones
Wang, De; Wang, Guo-Peng; Sun, Yao-Liang; Zhu, Shou-Fei; Wei, Yin; Zhou, Qi-Lin; Shi, Min; Chem. Sci. 6 (2015) 7319–; doi:10.1039/C5SC03135D

data_1531044
_publ_section_title
;
 Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates
 with benzofuranone-derived olefins for a highly regio-, diastereo- and
 enantioselective synthesis of spiro-benzofuranones
;
_journal_issue                   12
_journal_name_full               'Chem. Sci.'
_journal_page_first              7319
_journal_paper_doi               10.1039/C5SC03135D
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30 H22 O4'
_chemical_formula_weight         446.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2013-09-16 deposited with the CCDC.
2015-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.5560(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.07170(10)
_cell_length_b                   8.84390(10)
_cell_length_c                   19.5443(3)
_cell_measurement_reflns_used    4599
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      69.10
_cell_measurement_theta_min      4.55
_cell_volume                     1214.33(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9496
_diffrn_reflns_point_group_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.837
_diffrn_reflns_theta_min         2.275
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_refine_diff_density_max         1.215
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
; 
 Flack x determined using 1633 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.17(13)
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     161
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0746
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1932P)^2^+0.6934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2230
_refine_ls_wR_factor_ref         0.2278
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.844
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                4005
_reflns_number_total             4122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc03135d2.cif
_cod_data_source_block           cu_dm13504_0m
_cod_depositor_comments
'Adding full bibliography for 1531044--1531046.cif.'
_cod_database_code               1531044
_shelx_estimated_absorpt_t_min   0.850
_shelx_estimated_absorpt_t_max   0.904
_shelxl_version_number           2013-4
_shelx_res_checksum              84952
_shelx_hkl_checksum              76996