Cyclic Oxonitriles: Stereodivergent Grignard Addition-Alkylations
Fraser F. Fleming; Guoqing Wei; Zhiyu Zhang; Omar W. Steward; Journal of Organic Chemistry 72 (2007) 5270–5275; doi:10.1021/jo070678y

data_4024007
_publ_contact_author_address
;
 Department of Chemistry and Biochemistry
 Duquesne University
 Pittsburgh, PA 15282 USA
;
_publ_contact_author_email       steward@duq.edu
_publ_contact_author_fax         '412 396 5683'
_publ_contact_author_name        'Dr.Omar W. Steward'
_publ_contact_author_phone       '412 396 6338'
_publ_section_title
;
 Cyclic Oxonitriles: Stereodivergent Grignard Addition-Alkylations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5270
_journal_page_last               5275
_journal_paper_doi               10.1021/jo070678y
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C20 H24 N2 O5'
_chemical_formula_sum            'C20 H24 N2 O5'
_chemical_formula_weight         372.41
_chemical_name_systematic
; 
(1R,2S,3S)3-cyano-1,2-dimethyl-3-pivaloylcyclopentyl 
4-nitrobenzoate 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'May. 22, 2006'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.738(5)
_cell_angle_beta                 97.890(5)
_cell_angle_gamma                90.954(5)
_cell_formula_units_Z            2
_cell_length_a                   7.028(3)
_cell_length_b                   10.388(4)
_cell_length_c                   13.769(5)
_cell_measurement_reflns_used    8275
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.22
_cell_measurement_theta_min      2.4
_cell_volume                     966.0(6)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Samrt Apex II'
_diffrn_measurement_method       '\f and \w 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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8275
_diffrn_reflns_theta_full        26.22
_diffrn_reflns_theta_max         26.22
_diffrn_reflns_theta_min         1.54
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         3803
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABSsheldrick, 2002'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0647
_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^)+(0.1142P)^2^+0.2313P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1857
_refine_ls_wR_factor_ref         0.2137
_reflns_number_gt                2471
_reflns_number_total             3803
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo070678ysi20070407_010240_4.cif
_cod_data_source_block           ffgw001_14k
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               4024007