Remote C6-Selective Ruthenium-Catalyzed C–H Alkylation of Indole Derivatives via σ-Activation
Leitch, Jamie A.; McMullin, Claire L.; Mahon, Mary F.; Bhonoah, Yunas; Frost, Christopher G.; ACS Catalysis  (2017) 2616–; doi:10.1021/acscatal.7b00038

data_4514067
_publ_section_title
;
 Remote C6-Selective Ruthenium-Catalyzed C--H Alkylation of Indole
 Derivatives via \s-Activation
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2616
_journal_paper_doi               10.1021/acscatal.7b00038
_journal_year                    2017
_chemical_formula_moiety         'C24 H29 N3 O4'
_chemical_formula_sum            'C24 H29 N3 O4'
_chemical_formula_weight         423.50
_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
_audit_creation_date             2016-08-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                106.921(4)
_cell_angle_beta                 90.760(4)
_cell_angle_gamma                95.278(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2094(3)
_cell_length_b                   12.0942(5)
_cell_length_c                   13.0064(6)
_cell_measurement_reflns_used    5872
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.1700
_cell_measurement_theta_min      3.5520
_cell_volume                     1079.40(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 8.1150
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10342
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.367
_diffrn_reflns_theta_min         3.555
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.149
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0504P)^2^+0.3220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3846
_reflns_number_total             4306
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b00038_si_002.cif
_cod_data_source_block           s16cgf2-4a
_cod_database_code               4514067
_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. Others
 Fixed Sof: O4(0.45) O4A(0.55) C21(0.45) H21A(0.45) H21B(0.45) C22(0.45)
 H22A(0.45) H22B(0.45) H22C(0.45) C21A(0.55) H21C(0.55) H21D(0.55) C22A(0.55)
 H22D(0.55) H22E(0.55) H22F(0.55)
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C21(H21A,H21B), C21A(H21C,H21D)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C8(H8), C10(H10), C11(H11), C12(H12)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C22(H22A,H22B,H22C), C22A(H22D,H22E,H22F)
;
_shelx_shelxl_version_number     2014/7
_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
;