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_1508333
_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            'C23 H19 N O2'
_chemical_formula_weight         341.39
_space_group_IT_number           14
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_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
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_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.013(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0652(8)
_cell_length_b                   10.5023(10)
_cell_length_c                   20.722(2)
_cell_measurement_reflns_used    2010
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.940
_cell_measurement_theta_min      5.523
_cell_volume                     1752.8(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0315
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_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10428
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43429
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.137
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.202
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0540P)^2^+0.4957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1256
_reflns_number_gt                2663
_reflns_number_total             3441
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301750b_si_003.cif
_cod_data_source_block           cd212248
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P2(1)/n
_cod_database_code               1508333