Access to chiral γ-butenolides via palladium-catalyzed asymmetric allylic C-H alkylation of 1,4-dienes.
Dai, Zhen-Yao; Wang, Pu-Sheng; Gong, Liu-Zhu; Chemical communications (Cambridge, England) 57 (2021) 6748–6751; doi:10.1039/d1cc02295d

data_7128484
_publ_section_title
;
 Access to chiral \g-butenolides via palladium-catalyzed asymmetric
 allylic C-H alkylation of 1,4-dienes.
;
_journal_issue                   55
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6748
_journal_page_last               6751
_journal_paper_doi               10.1039/d1cc02295d
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C49 H34 F12 N3 O6 P'
_chemical_formula_sum            'C49 H34 F12 N3 O6 P'
_chemical_formula_weight         1019.76
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-17 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.284(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.5180(7)
_cell_length_b                   8.3701(4)
_cell_length_c                   19.8041(11)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      53.95
_cell_measurement_theta_min      2.90
_cell_volume                     2197.5(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      169.98
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23560
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.906
_diffrn_reflns_theta_min         2.900
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.972
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1399 before and 0.0643 after correction. The Ratio of minimum to maximum transmission is 0.7826. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.364
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     640
_refine_ls_number_reflns         7351
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0638
_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          0.1576
_refine_ls_wR_factor_ref         0.1775
_reflns_Friedel_coverage         0.652
_reflns_Friedel_fraction_full    0.765
_reflns_Friedel_fraction_max     0.748
_reflns_number_gt                5579
_reflns_number_total             7351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02295d2.cif
_cod_data_source_block           20190115dzy
_cod_depositor_comments
'Adding full bibliography for 7128483--7128484.cif.'
_cod_database_code               7128484
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.868
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C13(H13A,H13B), C14(H14A,
 H14B), C15(H15A,H15B), C16(H16A,H16B), C41(H41A,H41B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C29(H29),
 C30(H30), C31(H31), C34(H34), C36(H36), C38(H38), C43(H43), C45(H45), C47(H47)
;
_shelx_res_checksum              40897
_olex2_submission_special_instructions 'No special instructions were received'