Pd-Catalyzed Cyclization and Carbene Migratory Insertion: New Approach to 3-Vinylindoles and 3-Vinylbenzofurans.
Liu, Zhenxing; Xia, Ying; Zhou, Shiyi; Wang, Long; Zhang, Yan; Wang, Jianbo; Organic letters 15 (2013) 5032–5035; doi:10.1021/ol402368h

data_1512376
_publ_section_title
;
 Pd-Catalyzed Cyclization and Carbene Migratory Insertion: New Approach to
 3-Vinylindoles and 3-Vinylbenzofurans.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5032
_journal_page_last               5035
_journal_paper_doi               10.1021/ol402368h
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C26 H18 O'
_chemical_formula_sum            'C26 H18 O'
_chemical_formula_weight         346.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-09-16
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.828(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.6916(12)
_cell_length_b                   5.7783(5)
_cell_length_c                   33.895(2)
_cell_measurement_reflns_used    3653
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.2340
_cell_measurement_theta_min      3.6690
_cell_volume                     3569.5(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.15
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.8524
_diffrn_measurement_details
;
  1 omega   38.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  178.0000 -180.0000 31

  2 omega  -20.00   15.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -99.0000 -150.0000 35

  3 omega  -33.00   35.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -38.0000 -150.0000 68

  4 omega  -38.00   39.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6392   38.0000    0.0000 77
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0217167000
_diffrn_orient_matrix_UB_12      0.0593238000
_diffrn_orient_matrix_UB_13      0.0167617000
_diffrn_orient_matrix_UB_21      0.0321225000
_diffrn_orient_matrix_UB_22      -0.0308736000
_diffrn_orient_matrix_UB_23      -0.0066329000
_diffrn_orient_matrix_UB_31      -0.0028816000
_diffrn_orient_matrix_UB_32      0.1030764000
_diffrn_orient_matrix_UB_33      -0.0116366000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            8312
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         2.937
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0068(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+1.6394P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2700
_reflns_number_total             3503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol402368h_si_003.cif
_cod_data_source_block           exp_2276
_cod_original_cell_volume        3569.5(5)
_cod_database_code               1512376
_chemical_oxdiff_formula         'C26 H17 O1'
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23),
  C25(H25), C26(H26)
;
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.985
_shelxl_version_number           2013-3