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_4133809
_publ_section_title
;
 Hydrosilylation-Promoted Furan Diels-Alder Cycloadditions with
 Stereoselectivity Controlled by the Silyl Group.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b11909
_journal_year                    2019
_chemical_formula_moiety         'C30 H42 F N O3 S Si'
_chemical_formula_sum            'C30 H42 F N O3 S Si'
_chemical_formula_weight         543.79
_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             2018-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                93.464(5)
_cell_angle_beta                 90.484(5)
_cell_angle_gamma                105.891(5)
_cell_formula_units_Z            2
_cell_length_a                   8.3949(5)
_cell_length_b                   10.5821(6)
_cell_length_c                   17.3603(9)
_cell_measurement_reflns_used    8616
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      32.6620
_cell_measurement_theta_min      2.0060
_cell_volume                     1480.07(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -115.00  65.00   1.00    4.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  35.00   1.00    4.00    --  -25.00  45.00  90.00  150
  3  \w   -115.00  35.00   1.00    4.00    --  -25.00  45.00 180.00  150
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0376616000
_diffrn_orient_matrix_UB_12      -0.0426092000
_diffrn_orient_matrix_UB_13      0.0187355000
_diffrn_orient_matrix_UB_21      -0.0762515000
_diffrn_orient_matrix_UB_22      -0.0295912000
_diffrn_orient_matrix_UB_23      0.0173217000
_diffrn_orient_matrix_UB_31      -0.0221365000
_diffrn_orient_matrix_UB_32      -0.0467593000
_diffrn_orient_matrix_UB_33      -0.0320238000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19479
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.844
_diffrn_reflns_theta_min         2.005
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       blocks
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.131
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       0.034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         9756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1596
_refine_ls_R_factor_gt           0.1227
_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^)+(0.1160P)^2^+7.6670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3349
_refine_ls_wR_factor_ref         0.3566
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6545
_reflns_number_total             9756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b11909_si_002.cif
_cod_data_source_block           4n
_cod_original_cell_volume        1480.06(15)
_cod_database_code               4133809
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.960
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C1(H1), C2(H2), C6(H6), C15(H15), C18(H18), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C11(H11), C13(H13), C14(H14), C25(H25), C26(H26), C28(H28),
 C29(H29)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.423
_oxdiff_exptl_absorpt_empirical_full_min 0.682