Brønsted Acid Mediated Alkenylation and Copper-Catalyzed Aerobic Oxidative Ring Expansion/Intramolecular Electrophilic Substitution of Indoles with Propargyl Alcohols: A Novel One-Pot Approach to Cyclopenta[c]quinolines.
Gangadhararao, G.; Uruvakilli, Anasuyamma; Swamy, K. C. Kumara; Organic letters 16 (2014) 6060–; doi:10.1021/ol502783j

data_1518288
_publ_section_title
;
 Br\/onsted Acid Mediated Alkenylation and Copper-Catalyzed Aerobic
 Oxidative Ring Expansion/Intramolecular Electrophilic Substitution of
 Indoles with Propargyl Alcohols: A Novel One-Pot Approach to
 Cyclopenta[c]quinolines.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6060
_journal_paper_doi               10.1021/ol502783j
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C32 H25 N O'
_chemical_formula_weight         439.53
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
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_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4240(16)
_cell_length_b                   9.4223(10)
_cell_length_c                   21.475(3)
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_cell_measurement_temperature    293(2)
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_cell_measurement_theta_min      3.0730
_cell_volume                     2278.7(5)
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_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
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7934
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.82
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_number         'not applicable'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90609
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0043(7)
_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   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0444P)^2^+0.3400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                2915
_reflns_number_total             4006
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502783j_si_001.cif
_cod_data_source_block           compound-4ac
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 1518287--1518289.cif.
;
_cod_original_cell_volume        2278.6(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1518288