Phosphine-catalyzed Enantioselective [3+2] Cycloadditions of -Substituted Allenoates with β-Perfluoroalkyl Enones
Zhang, Junliang; Zhou, Wei; Wang, Hua-Min; Tao, Mengna; Zhu, Chao-Ze; Lin, Tao-Yan; Chem. Sci.  (2017) –; doi:10.1039/C7SC01432E

data_1545773
_publ_section_title
;
 Phosphine-catalyzed Enantioselective [3+2] Cycloadditions of -Substituted
 Allenoates with \b-Perfluoroalkyl Enones
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC01432E
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H19 F3 O3'
_chemical_formula_sum            'C22 H19 F3 O3'
_chemical_formula_weight         388.37
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-09-11 deposited with the CCDC.
2017-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                67.7570(10)
_cell_angle_beta                 88.9110(10)
_cell_angle_gamma                87.4110(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7678(2)
_cell_length_b                   10.7305(2)
_cell_length_c                   10.8657(2)
_cell_measurement_reflns_used    4886
_cell_measurement_temperature    130
_cell_measurement_theta_max      68.707
_cell_measurement_theta_min      4.40
_cell_volume                     945.24(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      130
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7792
_diffrn_reflns_point_group_measured_fraction_full 0.675
_diffrn_reflns_point_group_measured_fraction_max 0.663
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.186
_diffrn_reflns_theta_min         4.396
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1144 before and 0.0565 after correction.
The Ratio of minimum to maximum transmission is 0.7321.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1290 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         4680
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.898
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0383
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.419
_reflns_Friedel_fraction_full    0.402
_reflns_Friedel_fraction_max     0.391
_reflns_number_gt                4568
_reflns_number_total             4680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc01432e2.cif
_cod_data_source_block           cu_dm16442_0m
_cod_depositor_comments
;

2019-02-27
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C22 H19 F3 O3)'
_cod_original_formula_sum        'C44 H38 F6 O6'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     776.74
_cod_database_code               1545773
_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.a Ternary CH refined with riding coordinates:
 C2(H2), C8(H8), C9(H9), C24(H24), C30(H30), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C29(H29), C34(H34), C35(H35), C36(H36), C37(H37),
  C38(H38), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              78093
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'