Highly Regio- and Enantioselective Formal [3 + 2]-Annulation of Indoles with Electrophilic Enol Carbene Intermediates.
Jing, Changcheng; Cheng, Qing-Qing; Deng, Yongming; Arman, Hadi; Doyle, Michael P.; Organic letters 18 (2016) 4550–4553; doi:10.1021/acs.orglett.6b02192

data_1555717
_publ_section_title
;
 Highly Regio- and Enantioselective Formal [3 + 2]-Annulation of Indoles
 with Electrophilic Enol Carbene Intermediates.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4550
_journal_page_last               4553
_journal_paper_doi               10.1021/acs.orglett.6b02192
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C24 H35 Br N2 O2 Si'
_chemical_formula_sum            'C24 H35 Br N2 O2 Si'
_chemical_formula_weight         491.54
_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     direct
_audit_creation_date             2015-08-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                80.372(6)
_cell_angle_beta                 88.311(6)
_cell_angle_gamma                87.675(6)
_cell_formula_units_Z            4
_cell_length_a                   11.7811(6)
_cell_length_b                   12.1808(6)
_cell_length_c                   17.8426(13)
_cell_measurement_reflns_used    9773
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     2521.7(3)
_computing_cell_refinement
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
scan:
	Number of images: 246
	           Slice: -68.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 55.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 210
	           Slice: -125.0000 - -20.0000
	     Image width: 0.5000
	        Exp time: 55.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 102
	           Slice: -55.0000 - -4.0000
	     Image width: 0.5000
	        Exp time: 55.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 98
	           Slice: -51.0000 - -2.0000
	     Image width: 0.5000
	        Exp time: 55.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 180.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 74
	           Slice: -115.0000 - -78.0000
	     Image width: 0.5000
	        Exp time: 55.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 35.0000
	          2theta: -35.0000
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.027528
_diffrn_orient_matrix_UB_12      -0.047972
_diffrn_orient_matrix_UB_13      0.064570
_diffrn_orient_matrix_UB_21      -0.076761
_diffrn_orient_matrix_UB_22      0.002264
_diffrn_orient_matrix_UB_23      0.030898
_diffrn_orient_matrix_UB_31      -0.004861
_diffrn_orient_matrix_UB_32      -0.045439
_diffrn_orient_matrix_UB_33      -0.033643
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16794
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.048
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         3.091
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.699
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.37
_refine_diff_density_max         1.696
_refine_diff_density_min         -1.028
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         8878
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0733
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+6.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1682
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6285
_reflns_number_total             8878
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02192_si_002.cif
_cod_data_source_block           cd1357a
_cod_database_code               1555717
_shelx_estimated_absorpt_t_max   0.572
_shelx_estimated_absorpt_t_min   0.529
_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
 C46-C45
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C46) = Uanis(C48) = Uanis(C47)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C31(H31), C35(H35), C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C32(H32A,H32B), C42(H42A,H42B), C38(H38A,H38B), C14(H14A,H14B),
 C41(H41A,H41B), C39(H39A,H39B), C40(H40A,H40B), C18(H18A,H18B), C15(H15A,H15B),
  C17(H17A,H17B), C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C26(H26), C29(H29), C27(H27)
4.d Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C12(H12A,H12B,H12C), C48(H48A,H48B,H48C), C19(H19A,H19B,
 H19C), C23(H23A,H23B,H23C), C43(H43A,H43B,H43C), C24(H24A,H24B,H24C), C22(H22A,
 H22B,H22C), C20(H20A,H20B,H20C), C44(H44A,H44B,H44C), C47(H47A,H47B,H47C),
 C46(H46A,H46B,H46C)
;
_shelx_res_checksum              57834
_shelx_hkl_checksum              90506
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method
;
glass fiber
;
_olex2_submission_special_instructions 'No special instructions were received'