Gold-catalyzed cascade C-H/C-H cross-coupling/cyclization/alkynylation: an efficient access to 3-alkynylpyrroles.
Zhang, Shuai; Ma, Yuanhong; Lan, Jingbo; Song, Feijie; You, Jingsong; Organic & biomolecular chemistry 13 (2015) 5867–5870; doi:10.1039/c5ob00599j

data_7154476
_publ_section_title
;
 Gold-catalyzed cascade C-H/C-H cross-coupling/cyclization/alkynylation:
 an efficient access to 3-alkynylpyrroles.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5867
_journal_page_last               5870
_journal_paper_doi               10.1039/c5ob00599j
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C28 H23 N O2'
_chemical_formula_sum            'C28 H23 N O2'
_chemical_formula_weight         405.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2013-06-13
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2014-10-31 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.582(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5662(7)
_cell_length_b                   10.3707(7)
_cell_length_c                   18.8464(12)
_cell_measurement_reflns_used    3515
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4330
_cell_measurement_theta_min      2.9849
_cell_volume                     2166.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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
;
SHELXL-2012, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 15.9784
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -19.00    7.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2889  -99.0000  120.0000 26

  2 omega   -6.00   21.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2889  -99.0000  -30.0000 27

  3 omega  -34.00   23.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827  -57.0000  -30.0000 57

  4 omega  -28.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827   19.0000 -180.0000 117

  5 omega  -53.00   29.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2889   77.0000  120.0000 82
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0637706000
_diffrn_orient_matrix_UB_12      0.0063216000
_diffrn_orient_matrix_UB_13      -0.0112929000
_diffrn_orient_matrix_UB_21      0.0056206000
_diffrn_orient_matrix_UB_22      0.0623074000
_diffrn_orient_matrix_UB_23      -0.0141467000
_diffrn_orient_matrix_UB_31      -0.0022608000
_diffrn_orient_matrix_UB_32      -0.0274611000
_diffrn_orient_matrix_UB_33      -0.0348167000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11360
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.991
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0489P)^2^+0.5937P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3461
_reflns_number_total             4411
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00599j2.cif
_cod_data_source_block           0610luo40
_cod_depositor_comments
'Adding full bibliography for 7154476--7154477.cif.'
_cod_database_code               7154476
_reflns_odcompleteness_completeness 99.64
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.977
_shelx_res_checksum              18231
_shelxl_version_number           2013-2