Pd-catalyzed C-H carbonylation of (hetero)arenes with formates and intramolecular dehydrogenative coupling: a shortcut to indolo[3,2-c]coumarins.
Wu, Jie; Lan, Jingbo; Guo, Siyuan; You, Jingsong; Organic letters 16 (2014) 5862–5865; doi:10.1021/ol502749b

data_1518178
_publ_section_title
;
 Pd-catalyzed C-H carbonylation of (hetero)arenes with formates and
 intramolecular dehydrogenative coupling: a shortcut to
 indolo[3,2-c]coumarins.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5862
_journal_page_last               5865
_journal_paper_doi               10.1021/ol502749b
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C18.1 H12.56 N0.76 O1.51, 0.24(C16 H10 N1 O2)'
_chemical_formula_sum            'C22 H15 N O2'
_chemical_formula_weight         325.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
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_atom_sites_solution_secondary   difmap
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  Olex2 1.1
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;
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_cell_length_a                   8.4366(6)
_cell_length_b                   8.8120(6)
_cell_length_c                   11.1014(8)
_cell_measurement_reflns_used    1652
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.2640
_cell_measurement_theta_min      3.5660
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
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_diffrn_measurement_details
;
  1 omega  -25.00   18.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -99.0000  -60.0000 43

  2 omega  -22.00   14.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -99.0000  120.0000 36

  3 omega   38.00   90.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361  178.0000  -30.0000 52

  4 omega   47.00   95.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361 -178.0000  -90.0000 48

  5 omega   -6.00   85.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361   38.0000  120.0000 91

  6 omega  -39.00   63.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361  -19.0000  -90.0000 102

  7 omega  -39.00   17.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611   57.0000   90.0000 56
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0530643000
_diffrn_orient_matrix_UB_12      0.0340322000
_diffrn_orient_matrix_UB_13      -0.0456852000
_diffrn_orient_matrix_UB_21      -0.0549590000
_diffrn_orient_matrix_UB_22      0.0630698000
_diffrn_orient_matrix_UB_23      -0.0112054000
_diffrn_orient_matrix_UB_31      0.0355631000
_diffrn_orient_matrix_UB_32      0.0379991000
_diffrn_orient_matrix_UB_33      0.0439670000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6725
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.98
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             340
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_refine_ls_extinction_method     none
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_refine_ls_number_parameters     290
_refine_ls_number_reflns         3323
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_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0576
_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^)+(0.0492P)^2^+0.1494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1533
_reflns_number_gt                1931
_reflns_number_total             3323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502749b_si_003.cif
_cod_data_source_block           131204_s6_wj
_cod_depositor_comments
'Adding full bibliography for 1518178--1518179.cif.'
_cod_original_cell_volume        817.92(10)
_cod_database_code               1518178
_chemical_oxdiff_formula         c12h12n2o3
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32