Enantioselective palladium-catalyzed C(sp2)‒C(sp2) σ bond activation of cyclopropenones by merging desymmetrization and (3 + 2) spiroannulation with cyclic 1,3-diketones
Zhou, Han-Qi; Gu, Xing-Wei; Zhou, Xiao-Hua; Li, Li; Ye, Fei; Yin, Guan-Wu; Xu, Zheng; Xu, Li-Wen; Chemical Science  (2021) –; doi:10.1039/D1SC04558J

data_1564782
_publ_section_title
;
 Enantioselective palladium-catalyzed C(sp2)--C(sp2) \s bond activation of
 cyclopropenones by merging desymmetrization and (3 + 2) spiroannulation
 with cyclic 1,3-diketones
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04558J
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H22 O3'
_chemical_formula_sum            'C28 H22 O3'
_chemical_formula_weight         406.45
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-08-21 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.29900(10)
_cell_length_b                   10.99710(10)
_cell_length_c                   28.3111(3)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      70.984
_cell_measurement_theta_min      4.020
_cell_volume                     2272.47(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_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  0.0355
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            19670
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.080
_diffrn_reflns_theta_min         5.093
_diffrn_source_current           0.64
_diffrn_source_power             0.028608
_diffrn_source_voltage           44.7
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1457 before and 0.0555 after correction.
The Ratio of minimum to maximum transmission is 0.5290.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1739 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4309
_refine_ls_number_restraints     261
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0715P)^2^+0.1724P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                4229
_reflns_number_total             4309
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04558j2.cif
_cod_data_source_block           mo200820b
_cod_database_code               1564782
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.888
_shelx_estimated_absorpt_t_min   0.863
_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 C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C16(H16), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27),
  C28(H28)
3.c Fitted hexagon refined as free rotating group:
 C16(C11,C12,C13,C14,C15), C23(C24,C25,C26,C27,C28)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              36851
_shelx_hkl_checksum              38982
_olex2_submission_special_instructions 'No special instructions were received'