Anomalous Reactivity and Selectivity in the Intermolecular Diels-Alder Reactions of Multisubstituted Acyclic Dienes with Geometrical Isomers of Enals.
Zhou, Jia-Hui; Cai, Sai-Hu; Xu, Yun-He; Loh, Teck-Peng; Organic letters 18 (2016) 2355–2358; doi:10.1021/acs.orglett.6b00783

data_1543818
_publ_section_title
;
 Anomalous Reactivity and Selectivity in the Intermolecular Diels-Alder
 Reactions of Multisubstituted Acyclic Dienes with Geometrical Isomers of
 Enals.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2355
_journal_page_last               2358
_journal_paper_doi               10.1021/acs.orglett.6b00783
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C38 H48 O6 Si'
_chemical_formula_sum            'C38 H48 O6 Si'
_chemical_formula_weight         628.85
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-17
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                87.511(4)
_cell_angle_beta                 81.820(4)
_cell_angle_gamma                82.982(4)
_cell_formula_units_Z            2
_cell_length_a                   11.2348(5)
_cell_length_b                   11.3819(6)
_cell_length_c                   14.1336(6)
_cell_measurement_reflns_used    4129
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      29.0783
_cell_measurement_theta_min      3.1814
_cell_volume                     1774.90(15)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15023
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9700
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         7167
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.3623P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1460
_reflns_number_gt                5193
_reflns_number_total             7167
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00783_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1774.90(14)
_cod_database_code               1543818
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H6(0.062) H2(0.056) H3(0.049) H5(0.053) H16A(0.1) H16B(0.1)
 H16C(0.1) H17A(0.104) H17B(0.104) H17C(0.104) H4(0.06) H21A(0.053) H21B(0.053)
 H7A(0.064) H7B(0.064) H15A(0.061) H15B(0.061) H8A(0.081) H8B(0.081) H10(0.103)
 H11(0.131) H12(0.131) H13(0.114) H14(0.087) H35A(0.146) H35B(0.146)
 H35C(0.146) H34A(0.126) H34B(0.126) H34C(0.126) H37A(0.14) H37B(0.14)
 H37C(0.14) H23(0.071) H24(0.083) H25(0.084) H26(0.084) H27(0.07) H29(0.073)
 H30(0.089) H31(0.093) H32(0.089) H33(0.07) H19A(0.123) H19B(0.123) H20A(0.223)
 H20B(0.223) H20C(0.223) H19C(0.123) H19D(0.123) H20D(0.223) H20E(0.223)
 H20F(0.223)
 Fixed X: H6(0.1567) H2(0.3104) H3(0.4452) H5(0.3722) H16A(0.0527)
 H16B(0.0975) H16C(0.0319) H17A(0.2847) H17B(0.3449) H17C(0.2057) H4(0.3237)
 H21A(0.5578) H21B(0.6177) H7A(0.2377) H7B(0.2572) H15A(0.6123) H15B(0.5245)
 H8A(0.3183) H8B(0.4301) H10(0.3947) H11(0.2614) H12(0.0632) H13(-0.0009)
 H14(0.13) H35A(0.9201) H35B(0.8651) H35C(0.8593) H34A(0.707) H34B(0.6385)
 H34C(0.7789) H37A(0.6447) H37B(0.5547) H37C(0.6314) H23(0.8044) H24(0.9478)
 H25(1.0873) H26(1.0793) H27(0.933) H29(0.9188) H30(0.9287) H31(0.7598)
 H32(0.578) H33(0.5676) H19A(0.6304) H19B(0.7143) H20A(0.8269) H20B(0.8285)
 H20C(0.7437) H19C(0.8074) H19D(0.7611) H20D(0.7006) H20E(0.7749) H20F(0.6364)
 Fixed Y: H6(0.3407) H2(0.6065) H3(0.4693) H5(0.2771) H16A(0.5622)
 H16B(0.6263) H16C(0.5125) H17A(0.4811) H17B(0.5987) H17C(0.5999) H4(0.2912)
 H21A(0.1712) H21B(0.2757) H7A(0.1411) H7B(0.159) H15A(0.4589) H15B(0.5052)
 H8A(-0.0492) H8B(-0.1054) H10(-0.0953) H11(-0.1474) H12(-0.1686) H13(-0.137)
 H14(-0.0848) H35A(0.3421) H35B(0.258) H35C(0.3938) H34A(0.5371) H34B(0.5026)
 H34C(0.5068) H37A(0.2524) H37B(0.3469) H37C(0.385) H23(0.4444) H24(0.4674)
 H25(0.3107) H26(0.1286) H27(0.1029) H29(0.0734) H30(-0.1199) H31(-0.2198) H32(-
 0.1211) H33(0.0727) H19A(0.9519) H19B(0.8462) H20A(0.9544) H20B(0.8246)
 H20C(0.928) H19C(0.7851) H19D(0.871) H20D(0.9046) H20E(0.9863) H20F(0.984)
 Fixed Z: H6(0.8436) H2(0.7341) H3(0.7838) H5(0.851) H16A(0.7242) H16B(0.8063)
 H16C(0.8297) H17A(0.5717) H17B(0.5693) H17C(0.603) H4(0.6057) H21A(0.7238)
 H21B(0.667) H7A(0.8352) H7B(0.7236) H15A(0.6622) H15B(0.5876) H8A(0.862)
 H8B(0.7927) H10(0.6115) H11(0.5134) H12(0.5773) H13(0.7356) H14(0.8319)
 H35A(0.9283) H35B(1.0093) H35C(1.0269) H34A(0.9654) H34B(0.8833) H34C(0.8643)
 H37A(1.0454) H37B(0.9996) H37C(1.0749) H23(0.71) H24(0.5796) H25(0.5264)
 H26(0.6036) H27(0.7318) H29(0.9054) H30(0.9607) H31(0.9742) H32(0.9402)
 H33(0.8853) H19A(0.593) H19B(0.5414) H20A(0.6251) H20B(0.6673) H20C(0.7205)
 H19C(0.6475) H19D(0.7328) H20D(0.5467) H20E(0.5959) H20F(0.6313)
;