Chiral phosphoproline-catalyzed asymmetric Michael addition of ketones to nitroolefins: an experimental and theoretical study.
Zeng, Zhiping; Luo, Ping; Jiang, Yao; Liu, Yan; Tang, Guo; Xu, Pengxiang; Zhao, Yufen; Blackburn, G. Michael; Organic & biomolecular chemistry 9 (2011) 6973–6978; doi:10.1039/c1ob06143g

data_7152025
_publ_section_title
;
 Chiral phosphoproline-catalyzed asymmetric Michael addition of ketones
 to nitroolefins: an experimental and theoretical study.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6973
_journal_page_last               6978
_journal_paper_doi               10.1039/c1ob06143g
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C30 H33 N2 O6 P S'
_chemical_formula_sum            'C30 H33 N2 O6 P S'
_chemical_formula_weight         580.62
_chemical_name_systematic
;
(R)-(diphenylphosphoryl)((S)-1-(quinolin-8-ylsulfonyl)pyrrolidin-2-yl)methanol
;
_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                 93.010(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.494(2)
_cell_length_b                   11.250(3)
_cell_length_c                   14.974(4)
_cell_measurement_reflns_used    6006
_cell_measurement_temperature    446(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.76
_cell_volume                     1428.9(6)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      446(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scan'
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11914
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.8295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6076
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0764P)^2^+0.1466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                5630
_reflns_number_total             6076
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06143g.txt
_cod_data_source_block           5
_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.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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 
;
_cod_original_cell_volume        1429.0(6)
_cod_original_sg_symbol_H-M      p_21
_cod_database_code               7152025