Palladium-catalyzed regioselective C–H alkynylation of indoles with bromoalkynes in water
Wu, Wanqing; Fang, Songjia; Jiang, Guangbin; Li, Meng; Jiang, Huanfeng; Organic Chemistry Frontiers 6 (2019) 2200–; doi:10.1039/C8QO01261J

data_1554555
_publ_section_title
;
 Palladium-catalyzed regioselective C--H alkynylation of indoles with
 bromoalkynes in water
;
_journal_issue                   13
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2200
_journal_paper_doi               10.1039/C8QO01261J
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C26 H31 N3 Si'
_chemical_formula_sum            'C26 H31 N3 Si'
_chemical_formula_weight         413.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-20 deposited with the CCDC.
2019-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 123.085(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   41.982(2)
_cell_length_b                   8.4505(2)
_cell_length_c                   16.3226(9)
_cell_measurement_reflns_used    10860
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.3720
_cell_measurement_theta_min      2.4630
_cell_volume                     4851.8(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -44.00  64.00   1.00    6.00    --  -11.74  77.00   0.00  108
  2  \w    -44.00  64.00   1.00    6.00    --  -11.74  77.00-120.00  108
  3  \w    -21.00  88.00   1.00    6.00    --   11.90  77.00 -90.00  109
  4  \w    -21.00  88.00   1.00    6.00    --   11.90  77.00 150.00  109
  5  \w    -20.00  -4.00   1.00    6.00    --   11.90 -99.00 150.00   16
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0190238500
_diffrn_orient_matrix_UB_12      -0.0053378500
_diffrn_orient_matrix_UB_13      -0.0408130000
_diffrn_orient_matrix_UB_21      0.0054274000
_diffrn_orient_matrix_UB_22      0.0356445000
_diffrn_orient_matrix_UB_23      -0.0299547000
_diffrn_orient_matrix_UB_31      0.0038964000
_diffrn_orient_matrix_UB_32      -0.0757934000
_diffrn_orient_matrix_UB_33      -0.0112028000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1163
_diffrn_reflns_av_unetI/netI     0.0916
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24245
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.316
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4265
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0955
_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^)+(0.1200P)^2^+21.7550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2461
_refine_ls_wR_factor_ref         0.2565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3698
_reflns_number_total             4265
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01261j2.cif
_cod_data_source_block           fsj
_cod_original_cell_volume        4851.9(5)
_cod_database_code               1554555
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.987
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C14, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C14 \\sim C15: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
4.a Rotating group:
 N3(H3A,H3B)
4.b Ternary CH refined with riding coordinates:
 C11(H11), C17(H17), C14(H14)
4.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C21(H21), C24(H24), C3(H3), C4(H4), C23(H23), C22(H22)
4.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C18(H18A,H18B,H18C), C16(H16A,H16B,
 H16C), C19(H19A,H19B,H19C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.551