Organocatalytic enantioselective allylic alkylation of α-aryl γ-lactones: an approach to densely functionalized quaternary stereocentres.
Mando, Morgane; Grellepois, Fabienne; Riguet, Emmanuel; Chemical communications (Cambridge, England) 56 (2020) 6640–6643; doi:10.1039/d0cc02058c

data_7126535
_publ_section_title
;
 Organocatalytic enantioselective allylic alkylation of \a-aryl
 \g-lactones: an approach to densely functionalized quaternary
 stereocentres.
;
_journal_issue                   49
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6640
_journal_page_last               6643
_journal_paper_doi               10.1039/d0cc02058c
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H26 O4 S'
_chemical_formula_sum            'C20 H26 O4 S'
_chemical_formula_weight         362.47
_chemical_name_systematic        prism
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-26 deposited with the CCDC.	2020-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4331(12)
_cell_length_b                   15.335(3)
_cell_length_c                   19.485(4)
_cell_measurement_reflns_used    9570
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.504
_cell_measurement_theta_min      3.668
_cell_volume                     1922.2(7)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22927
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.590
_diffrn_reflns_theta_min         3.668
_exptl_absorpt_coefficient_mu    1.665
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0854 before and 0.0716 after correction. The Ratio of minimum to maximum transmission is 0.9037. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.308
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.074(6)
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3782
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0263
_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^)+(0.0252P)^2^+0.4483P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0637
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3668
_reflns_number_total             3782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02058c2.cif
_cod_data_source_block           cu_19er014_0m_a
_cod_depositor_comments          'Adding full bibliography for 7126535.cif.'
_cod_original_cell_volume        1922.2(6)
_cod_database_code               7126535
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.644
_shelx_estimated_absorpt_t_min   0.575
_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, All O(H) groups
2. Restrained distances
 S1B-C13 = S1B-C20B
 1.74 with sigma of 0.001
 S1A-C13 = S1A-C20A
 1.74 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C19A) = Uanis(C18A) = Uanis(C17A) = Uanis(C16A)
Uanis(C16B) = Uanis(C17B) = Uanis(C18B) = Uanis(C16A)
Uanis(C15A) = Uanis(C20B) = Uanis(C15B) = Uanis(C20A)
4. Others
 Sof(S1A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=
 Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=1-FVAR(1)
 Sof(S1B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=
 Sof(H17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 C14B(H14B), C16B(H16B), C17B(H17B), C18B(H18B), C19B(H19B), C14A(H14A),
 C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
5.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_checksum              26100
_olex2_submission_special_instructions 'No special instructions were received'