Asymmetric Chlorocyclization of Indole-3-yl-benzamides for the Construction of Fused Indolines.
Yin, Qin; You, Shu-Li; Organic letters 16 (2014) 2426–2429; doi:10.1021/ol5007532

data_1514347
_publ_section_title
;
 Asymmetric Chlorocyclization of Indole-3-yl-benzamides for the
 Construction of Fused Indolines.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2426
_journal_page_last               2429
_journal_paper_doi               10.1021/ol5007532
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H19 Cl N2 O3 S'
_chemical_formula_weight         438.91
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.285(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7575(7)
_cell_length_b                   22.1410(17)
_cell_length_c                   10.8356(9)
_cell_measurement_reflns_used    3899
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.958
_cell_measurement_theta_min      5.003
_cell_volume                     2100.5(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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12830
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35442
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         6550
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                5525
_reflns_number_total             6550
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5007532_si_001.cif
_cod_data_source_block           cd213233
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1514347.cif.
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1514347