Synthesis of α-carbolines via Pd-catalyzed amidation and Vilsmeier-Haack reaction of 3-acetyl-2-chloroindoles.
Kumar, Arepalli Sateesh; Nagarajan, Rajagopal; Organic letters 13 (2011) 1398–1401; doi:10.1021/ol2000827

data_1502020
_publ_section_title
;
 Synthesis of \a-carbolines via Pd-catalyzed amidation and Vilsmeier-Haack
 reaction of 3-acetyl-2-chloroindoles.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1398
_journal_page_last               1401
_journal_paper_doi               10.1021/ol2000827
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C17 H17 Cl N2 O'
_chemical_formula_sum            'C17 H17 Cl N2 O'
_chemical_formula_weight         300.78
_space_group_IT_number           2
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_cell_angle_alpha                104.17(3)
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_cell_length_a                   7.190(3)
_cell_length_b                   10.650(4)
_cell_length_c                   10.795(3)
_cell_measurement_reflns_used    1116
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.3447
_cell_measurement_theta_min      2.9679
_cell_volume                     766.0(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
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_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4859
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.9707
_exptl_absorpt_correction_T_min  0.9024
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
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_refine_ls_number_reflns         2900
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_refine_ls_R_factor_all          0.1165
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1145
_reflns_number_gt                1347
_reflns_number_total             2900
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2000827_si_002.cif
_cod_data_source_block           rn27
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502020