Enantioselective phosphine-catalyzed [6 + 1] annulations of α-allyl allenoates with 1,1-bisnucleophiles.
Lai, Jingxiong; Cai, Wei; Huang, You; Chemical science 15 (2024) 11515–11520; doi:10.1039/d4sc02487g

data_1571962
_publ_section_title
;
 Enantioselective phosphine-catalyzed [6 + 1] annulations of &#x3b1;-allyl
 allenoates with 1,1-bisnucleophiles.
;
_journal_issue                   29
_journal_name_full               'Chemical science'
_journal_page_first              11515
_journal_page_last               11520
_journal_paper_doi               10.1039/d4sc02487g
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C21 H25 N O6 S'
_chemical_formula_sum            'C21 H25 N O6 S'
_chemical_formula_weight         419.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-10-08 deposited with the CCDC.	2024-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                93.270(4)
_cell_angle_beta                 99.190(4)
_cell_angle_gamma                90.759(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0682(6)
_cell_length_b                   8.2714(7)
_cell_length_c                   18.0737(16)
_cell_measurement_reflns_used    8847
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      60.48
_cell_measurement_theta_min      2.16
_cell_volume                     1041.13(16)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_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            11621
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.699
_diffrn_reflns_theta_min         4.320
_diffrn_source                   MetalJet
_diffrn_source_current           2.85
_diffrn_source_power             0.1986735
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.110
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.5302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1269 before and 0.0794 after correction.
The Ratio of minimum to maximum transmission is 0.7052.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0627
_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^)+(0.0512P)^2^+1.4839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1655
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3901
_reflns_number_total             4539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02487g2.cif
_cod_data_source_block           220929_wqangz_262959_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1571962.cif.
;
_cod_database_code               1571962
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.869
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C14(H14)
1.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C10(H10A,H10B), C13(H13A,H13B), C17(H17A,H17B), C20(H20A,H20B)
1.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C6(H6), C4(H4), C7(H7), C3(H3)
1.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              7005
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU