Hydrosilylation-Promoted Furan Diels-Alder Cycloadditions with Stereoselectivity Controlled by the Silyl Group.
Liu, Zhi-Yun; Zhang, Ming; Wang, Xiao-Chen; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b11909

data_4133807
_publ_section_title
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 Hydrosilylation-Promoted Furan Diels-Alder Cycloadditions with
 Stereoselectivity Controlled by the Silyl Group.
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_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b11909
_journal_year                    2019
_chemical_formula_moiety         'C24 H39 N O3 S Si'
_chemical_formula_sum            'C24 H39 N O3 S Si'
_chemical_formula_weight         449.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
????
;
_cell_angle_alpha                90
_cell_angle_beta                 100.49(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.817(2)
_cell_length_b                   8.0550(16)
_cell_length_c                   27.107(5)
_cell_measurement_reflns_used    6257
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8784
_cell_measurement_theta_min      2.2923
_cell_volume                     2537.1(8)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            27472
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.864
_diffrn_reflns_theta_min         2.527
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       blocks
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         6038
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0655P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1308
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4412
_reflns_number_total             6038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b11909_si_002.cif
_cod_data_source_block           3b
_cod_original_cell_volume        2537.1(9)
_cod_database_code               4133807
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.961
_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. Restrained distances
 C10-C16 = C10-C16' = C16-C17 = C17-C18 = C16'-C17' = C17'-C18'
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C16 \\sim C17 \\sim C18 \\sim C16' \\sim C17' \\sim C18': within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C16')
\\sim Ueq, Uanis(C17') \\sim Ueq, Uanis(C18') \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(H10A)=Sof(C16')=Sof(H16C)=Sof(H16D)=Sof(C17')=Sof(H17C)=Sof(H17D)=
 Sof(C18')=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(H10)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=
 Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C10(H10A), C11(H11)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
 C16'(H16C,H16D), C17'(H17C,H17D), C19(H19A,H19B), C21(H21A,H21B), C23(H23A,
 H23B)
5.c Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C18(H18A,H18B,H18C), C18'(H18D,H18E,H18F), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
5.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13)
;
_shelx_res_checksum              64503
_shelx_hkl_checksum              10967
_olex2_submission_special_instructions 'No special instructions were received'