Nucleophilic addition of grignard reagents to 3-acylindoles: stereoselective synthesis of highly substituted indoline scaffolds.
Wang, Lu; Shao, Yushang; Liu, Yuanhong; Organic letters 14 (2012) 3978–3981; doi:10.1021/ol301750b

data_1508335
_publ_section_title
;
 Nucleophilic addition of grignard reagents to 3-acylindoles:
 stereoselective synthesis of highly substituted indoline scaffolds.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3978
_journal_page_last               3981
_journal_paper_doi               10.1021/ol301750b
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C30 H25 N O2'
_chemical_formula_weight         431.51
_space_group_IT_number           2
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_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_creation_method           SHELXL-97
_cell_angle_alpha                71.896(2)
_cell_angle_beta                 82.514(2)
_cell_angle_gamma                86.686(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5516(10)
_cell_length_b                   9.6932(10)
_cell_length_c                   13.1354(13)
_cell_measurement_reflns_used    2177
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.884
_cell_measurement_theta_min      4.422
_cell_volume                     1145.9(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6990
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.0897
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0886P)^2^+0.2436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1716
_reflns_number_gt                3460
_reflns_number_total             4479
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301750b_si_005.cif
_cod_data_source_block           cd21288
_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 2.4.2 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      P-1
_cod_database_code               1508335