Asymmetric Synthesis of Indole Homo-Michael Adducts via Dynamic Kinetic Friedel–Crafts Alkylation with Cyclopropanes
Wales, Steven M.; Walker, Morgan M.; Johnson, Jeffrey S.; Organic Letters 15 (2013) 2558–; doi:10.1021/ol4010646

data_1512090
_publ_section_title
;
 Asymmetric Synthesis of Indole Homo-Michael Adducts via Dynamic Kinetic
 Friedel--Crafts Alkylation with Cyclopropanes
;
_journal_issue                   10
_journal_name_full               'Organic Letters'
_journal_page_first              2558
_journal_paper_doi               10.1021/ol4010646
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H37 N O5 Si'
_chemical_formula_sum            'C28 H37 N O5 Si'
_chemical_formula_weight         495.68
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-10-25
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Oct  4 2012 14:27:22, GUI svn.r4365)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.5580(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.5725(3)
_cell_length_b                   15.4880(6)
_cell_length_c                   11.7937(5)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.09
_cell_measurement_theta_min      3.81
_cell_volume                     1359.78(9)
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15254
_diffrn_reflns_theta_full        72.08
_diffrn_reflns_theta_max         72.08
_diffrn_reflns_theta_min         3.81
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.060
_exptl_absorpt_correction_T_max  0.8901
_exptl_absorpt_correction_T_min  0.7655
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADBAS was used for absorption correction.
wR2(int) was 0.0526 before and 0.0424 after correction.
The Ratio of minimum to maximum transmission is 0.8600.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.029(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5200
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.1337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0673
_reflns_number_gt                5120
_reflns_number_total             5200
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4010646_si_002.cif
_cod_data_source_block           x1210023
_cod_database_code               1512090
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H15 of C15, H17 of C17, H4 of C4, H3 of C3, H5 of C5, H8 of C8, H21 of C21,
  {H23A,H23B} of C23, H24 of C24, H18 of C18, H20 of C20, H2 of C2
 At 1.5 times of:
  {H28A,H28B,H28C} of C28, {H10A,H10B,H10C} of C10, {H9A,H9B,H9C} of C9,
  {H14A,H14B,H14C} of C14, {H13A,H13B,H13C} of C13, {H12A,H12B,H12C} of C12,
  {H22A,H22B,H22C} of C22, {H26A,H26B,H26C} of C26
2.a Ternary CH refined with riding coordinates:
 C15(H15), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C22(H22A,H22B,H22C), C26(H26A,H26B,H26C), C28(H28A,
 H28B,H28C)
;