Lewis Acid Catalyzed C-3 Alkylidenecyclopentenylation of Indoles: An Easy Access to Functionalized Indoles and Bisindoles
K. V., Radhakrishnan; Chand, S. Sarath; B. S, Sasidhar; Prakash, Praveen; P., Sasikumar; Preethalayam, Preethanuj; Jaroschik, Florian; Harakat, Dominique; Vasse, Jean-Luc; RSC Adv.  (2015) –; doi:10.1039/C5RA01107H

data_7219908
_publ_section_title
;
 Lewis Acid Catalyzed C-3 Alkylidenecyclopentenylation of Indoles: An Easy
 Access to Functionalized Indoles and Bisindoles
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA01107H
_journal_year                    2015
_chemical_formula_moiety         'C23 H29 N3 O4'
_chemical_formula_sum            'C23 H29 N3 O4'
_chemical_formula_weight         411.49
_chemical_name_systematic        sc_585_2
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc13qq0k
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-11-18 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                81.1780(10)
_cell_angle_beta                 86.5720(10)
_cell_angle_gamma                87.3920(10)
_cell_formula_units_Z            2
_cell_length_a                   8.5916(2)
_cell_length_b                   9.5191(3)
_cell_length_c                   14.2137(4)
_cell_measurement_reflns_used    6522
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.67
_cell_measurement_theta_min      2.85
_cell_volume                     1145.87(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17414
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4025
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1074P)^2^+0.1548P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1735
_reflns_number_gt                3008
_reflns_number_total             4025
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c5ra01107h2.cif
_cod_data_source_block           sc_585_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 3105 2015-03-04 15:46:00Z robertas 
;
_cod_original_sg_symbol_Hall     '-P 1  '
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               7219908