Synthesis of highly enantioenriched all-carbon quaternary centers: conjugate additions of chiral organolithium nucleophiles to alpha,alpha-dinitrile beta,beta-disubstituted olefins.
Jang, Doo Ok; Kim, Dwight D.; Pyun, Do Kyu; Beak, Peter; Organic letters 5 (2003) 4155–4157; doi:10.1021/ol035601k

data_1507386
_publ_contact_author
; 
Peter Beak
Roger Adams Laboratory
Department of Chemistry 
University of Illinois 
600 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Synthesis of highly enantioenriched all-carbon quaternary centers:
 conjugate additions of chiral organolithium nucleophiles to
 alpha,alpha-dinitrile beta,beta-disubstituted olefins.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              4155
_journal_page_last               4157
_journal_paper_doi               10.1021/ol035601k
_journal_volume                  5
_journal_year                    2003
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H24 N2 O3 S'
_chemical_formula_sum            'C27 H24 N2 O3 S'
_chemical_formula_weight         456.54
_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
_audit_update_record
; 
2003-04-11   text and data added, srw
2003-07-16   text and data added, ddk 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.467(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.140(3)
_cell_length_b                   21.770(9)
_cell_length_c                   7.897(3)
_cell_measurement_reflns_used    880
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      23.9
_cell_measurement_theta_min      2.6
_cell_volume                     1223.8(9)
_computing_cell_refinement       'SAINT V6.22 (Bruker, 2001)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.22 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6.10 (Bruker, 2001)'
_computing_publication_material  'CIFTAB (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL V6.10 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.10 (Bruker, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  p15was
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0884
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9764
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        1.7
_diffrn_standards_interval_time  610
_diffrn_standards_number         183
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9376
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_description       platy
_exptl_crystal_F_000             480
_exptl_crystal_id                p15was
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (1 1 0) scattering planes 
roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4474
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0393P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1088
_reflns_number_gt                3258
_reflns_number_total             4474
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol035601ksi20030825_014806.cif
_cod_data_source_block           p15was
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               1507386