Organocatalytic asymmetric synthesis of 3-chlorooxindoles bearing adjacent quaternary-tertiary centers.
Noole, Artur; Järving, Ivar; Werner, Franz; Lopp, Margus; Malkov, Andrei; Kanger, Tōnis; Organic letters 14 (2012) 4922–4925; doi:10.1021/ol302245b

data_1508659
_publ_section_title
;
 Organocatalytic asymmetric synthesis of 3-chlorooxindoles bearing
 adjacent quaternary-tertiary centers.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4922
_journal_page_last               4925
_journal_paper_doi               10.1021/ol302245b
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety
;
(C16 H12 Cl2 N2 O3)
;
_chemical_formula_sum            'C16 H12 Cl2 N2 O3'
_chemical_formula_weight         351.18
_chemical_melting_point          456
_chemical_name_common            'NOOLE 035 R4'
_chemical_name_systematic
; 
(R)-3,4-Dichloro-3-((S)-2-nitro-1-phenylethyl)indolin-2-one
;
_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                 90.798(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   8.2024(6)
_cell_length_b                   13.1986(9)
_cell_length_c                   22.0399(16)
_cell_measurement_reflns_used    6317
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.7429
_cell_measurement_theta_min      2.4078
_cell_volume                     2385.8(3)
_computing_cell_refinement       'APEX2 (Bruker, 2011); SAINT (Bruker, 2009)'
_computing_data_collection       'GIS (Bruker)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART X2S diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'XOS X-beam microfocus source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15411
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         0.92
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  0.8835
_exptl_absorpt_correction_T_min  0.7852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         8236
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0386P)^2^+0.1368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0901
_reflns_number_gt                7251
_reflns_number_total             8239
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302245b_si_002.cif
_cod_data_source_block           fw35final
_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      P12(1)1
_cod_database_code               1508659