A Copper-Catalyzed Synthesis of 3-Aroylindoles via a sp(3) C-H Bond Activation Followed by C-C and C-O Bond Formation.
Gogoi, Anupal; Guin, Srimanta; Rout, Saroj Kumar; Patel, Bhisma K.; Organic letters 15 (2013) 1802–1805; doi:10.1021/ol400692b

data_1511945
_publ_section_title
;
 A Copper-Catalyzed Synthesis of 3-Aroylindoles via a sp(3) C-H Bond
 Activation Followed by C-C and C-O Bond Formation.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1802
_journal_page_last               1805
_journal_paper_doi               10.1021/ol400692b
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C17 H15 N O'
_chemical_formula_sum            'C17 H15 N O'
_chemical_formula_weight         249.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.080(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1536(9)
_cell_length_b                   7.2700(6)
_cell_length_c                   16.7473(14)
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      0.967
_cell_measurement_theta_min      0.948
_cell_volume                     1332.67(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'ccd area decetor'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18525
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
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_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     174
_refine_ls_number_reflns         3304
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_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                1785
_reflns_number_total             3304
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400692b_si_002.cif
_cod_data_source_block           mp
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P21/n  '
_cod_database_code               1511945