The ruthenium(ii)-catalyzed C-H olefination of indoles with alkynes: the facile construction of tetrasubstituted alkenes under aqueous conditions.
Li, Ming; Yao, Tian-Yu; Sun, Sheng-Zheng; Yan, Ting-Xun; Wen, Li-Rong; Zhang, Lin-Bao; Organic & biomolecular chemistry 18 (2020) 3158–3163; doi:10.1039/d0ob00508h

data_7157428
_publ_section_title
;
 The ruthenium(ii)-catalyzed C-H olefination of indoles with alkynes: the
 facile construction of tetrasubstituted alkenes under aqueous conditions.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3158
_journal_page_last               3163
_journal_paper_doi               10.1039/d0ob00508h
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C26 H24 N2 O2'
_chemical_formula_sum            'C26 H24 N2 O2'
_chemical_formula_weight         396.47
_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
_audit_creation_date             2018-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-08 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                103.0430(10)
_cell_angle_beta                 104.128(2)
_cell_angle_gamma                92.353(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7780(2)
_cell_length_b                   10.6122(2)
_cell_length_c                   11.1756(2)
_cell_measurement_reflns_used    10250
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      75.2220
_cell_measurement_theta_min      4.2210
_cell_volume                     1089.87(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.945
_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    -86.00   3.00   0.50    0.08    --  -47.20 108.00 159.00  178
  2  \w      3.00  86.00   0.50    0.08    --   47.20-108.00  62.00  166
  3  \w   -161.00 -98.00   0.50    0.08    --  -99.00-108.00  62.00  126
  4  \w   -110.00 -26.00   0.50    0.08    --  -99.00 108.00 159.00  168
  5  \w     65.00 109.00   0.50    0.08    --  103.25-108.00  62.00   88
  6  \w     86.00 162.00   0.50    0.08    --  103.25 108.00 159.00  152
  7  \w   -102.00 -72.00   0.50    0.08    --  -47.20-125.00  90.00   60
  8  \w   -117.00 -76.00   0.50    0.08    --  -47.20-125.00-180.00   82
  9  \w    -18.00  56.00   0.50    0.08    --   47.20 -57.00  30.00  148
 10  \w    -16.00  57.00   0.50    0.08    --   47.20 -19.00  60.00  146
 11  \w    -21.00  37.00   0.50    0.08    --   47.20 -38.00 150.00  116
 12  \w   -146.00-100.00   0.50    0.08    --  -99.00 -94.00 120.00   92
 13  \w   -114.00 -78.00   0.50    0.08    --  -99.00  61.00   0.00   72
 14  \w   -101.00 -76.00   0.50    0.08    --  -99.00 -77.00 150.00   50
 15  \w   -111.00 -25.00   0.50    0.08    --  -99.00  30.00-150.00  172
 16  \w   -123.00 -71.00   0.50    0.08    --  -99.00-125.00 -60.00  104
 17  \w    -86.00 -26.00   0.50    0.08    --  -99.00 125.00 -90.00  120
 18  \w    -61.00 -27.00   0.50    0.08    --  -99.00  61.00   0.00   68
 19  \w   -162.00-110.00   0.50    0.08    --  -99.00 -77.00 150.00  104
 20  \w    -77.00 -51.00   0.50    0.08    --  -99.00  45.00  90.00   52
 21  \w   -168.00-132.00   0.50    0.08    --  -99.00-125.00 -60.00   72
 22  \w     40.00  87.00   0.50    0.08    --  103.25 -61.00  90.00   94
 23  \w    122.00 169.00   0.50    0.08    --  103.25  45.00 -30.00   94
 24  \w     75.00 122.00   0.50    0.08    --  103.25 -77.00-150.00   94
 25  \w     91.00 169.00   0.50    0.08    --  103.25  30.00  90.00  156
 26  \w     91.00 117.00   0.50    0.08    --  103.25-125.00  60.00   52
 27  \w     49.00  86.00   0.50    0.08    --  103.25-125.00  60.00   74
 28  \w     65.00  91.00   0.50    0.08    --  103.25 -94.00-150.00   52
 29  \w     31.00 114.00   0.50    0.08    --  103.25-125.00 -90.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1514368000
_diffrn_orient_matrix_UB_12      -0.0697603000
_diffrn_orient_matrix_UB_13      -0.0512767000
_diffrn_orient_matrix_UB_21      -0.0255518000
_diffrn_orient_matrix_UB_22      0.0447330000
_diffrn_orient_matrix_UB_23      0.1331167000
_diffrn_orient_matrix_UB_31      -0.0555518000
_diffrn_orient_matrix_UB_32      0.1247794000
_diffrn_orient_matrix_UB_33      -0.0335918000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12136
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.299
_diffrn_reflns_theta_min         4.206
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.201
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0513P)^2^+0.2986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4002
_reflns_number_total             4259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00508h2.cif
_cod_data_source_block           tx158
_cod_depositor_comments          'Adding full bibliography for 7157428.cif.'
_cod_database_code               7157428
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 99.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              94353
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.376
_oxdiff_exptl_absorpt_empirical_full_min 0.747