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_4024005
_publ_contact_author_address
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 Department of Chemistry and Biochemistry
 Duquesne University
 Pittsburgh, PA 15282 USA
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_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
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 Cyclic Oxonitriles: Stereodivergent Grignard Addition-Alkylations
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_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         'C16 H18 N2 O4'
_chemical_formula_sum            'C16 H18 N2 O4'
_chemical_formula_weight         302.32
_chemical_melting_point          347(5)
_chemical_name_systematic
; 
 (1R,2S,3S)-3-cyano-1,2,3-trimethylcyclopentyl 4-nitrobenzoate 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'July 24, 2006'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.627(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9492(4)
_cell_length_b                   19.5923(12)
_cell_length_c                   11.7429(7)
_cell_measurement_reflns_used    11090
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.1
_cell_measurement_theta_min      2.4
_cell_volume                     1580.72(16)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Smart 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  0.1344
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11090
_diffrn_reflns_theta_full        20.54
_diffrn_reflns_theta_max         20.54
_diffrn_reflns_theta_min         2.04
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         1579
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9863
_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         1579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0745P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1254
_reflns_number_gt                1236
_reflns_number_total             1579
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070678ysi20070407_010240_2.cif
_cod_data_source_block           ffgw016_14i
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '299-395 K' was changed to '347(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024005