Electronic Nature of Ketone Directing Group as a Key To Control C-2 vs C-4 Alkenylation of Indoles.
Lanke, Veeranjaneyulu; Bettadapur, Kiran R.; Prabhu, Kandikere Ramaiah; Organic letters 18 (2016) 5496–5499; doi:10.1021/acs.orglett.6b02698

data_1555852
_publ_section_title
;
 Electronic Nature of Ketone Directing Group as a Key To Control C-2 vs
 C-4 Alkenylation of Indoles.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5496
_journal_page_last               5499
_journal_paper_doi               10.1021/acs.orglett.6b02698
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C15 H12 F3 N O3'
_chemical_formula_sum            'C15 H12 F3 N O3'
_chemical_formula_weight         311.26
_chemical_name_systematic
'(E)-methyl 3-(1-methyl-3-(2,2,2-trifluoroacetyl)-1H-indol-4-yl)acrylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-11-24 deposited with the CCDC.
2016-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.279(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.703(3)
_cell_length_b                   13.0666(14)
_cell_length_c                   8.1548(9)
_cell_measurement_reflns_used    5587
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.68
_cell_measurement_theta_min      2.60
_cell_volume                     2935.8(6)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.885
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.885
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18287
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.478
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1571 before and 0.0951 after correction.
The Ratio of minimum to maximum transmission is 0.7751.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.146
_refine_ls_abs_structure_details
;
 Flack x determined using 1093 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_coef       0.031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         5048
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.219
_refine_ls_R_factor_all          0.1606
_refine_ls_R_factor_gt           0.1282
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3334
_refine_ls_wR_factor_ref         0.3520
_reflns_Friedel_coverage         0.970
_reflns_Friedel_fraction_full    0.859
_reflns_Friedel_fraction_max     0.867
_reflns_number_gt                3037
_reflns_number_total             5048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02698_si_002.cif
_cod_data_source_block           cc
_cod_original_cell_volume        2935.9(6)
_cod_database_code               1555852
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C18(H18), C20(H20), C3(H3), C11(H11), C2(H2), C17(H17), C5(H5),
 C22(H22), C26(H26), C7(H7), C6(H6)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C27(H27A,H27B,H27C), C30(H30A,H30B,
 H30C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'