Benzyl 2-Cyano-3,3-Dimethyl-1-pyrrolidinecarboxylate, a Versatile Intermediate for the Synthesis of 3,3-Dimethylproline Derivatives
Jesus R. Medina; Charles W. Blackledge; Karl F. Erhard; Jeffrey M. Axten; William H. Miller; Journal of Organic Chemistry 73 (2008) 3946–3949; doi:10.1021/jo7027163

data_4023402
_publ_section_title
;
 Benzyl 2-Cyano-3,3-Dimethyl-1-pyrrolidinecarboxylate, a Versatile
 Intermediate for the Synthesis of 3,3-Dimethylproline Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3946
_journal_page_last               3949
_journal_paper_doi               10.1021/jo7027163
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H17 Br N2 O3 S, C2 H6 O'
_chemical_formula_sum            'C15 H23 Br N2 O4 S'
_chemical_formula_weight         407.32
_chemical_name_systematic
; 
(R)-1-(4-Bromo-benzenesulfonyl)-3,3-dimethyl-pyrrolidine-2-carboxylic acid 
amide
;
_space_group_IT_number           1
_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
;
'Wed Jan 17 11:15:33 2007'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.624(13)
_cell_angle_beta                 86.823(12)
_cell_angle_gamma                88.264(13)
_cell_formula_units_Z            2
_cell_length_a                   7.0483(10)
_cell_length_b                   8.2090(14)
_cell_length_c                   16.012(3)
_cell_measurement_reflns_used    12540
_cell_measurement_temperature    110
_cell_measurement_theta_max      27.9999
_cell_measurement_theta_min      3.7413
_cell_volume                     923.9(3)
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 15.9890
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      'see scan set'
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  Xcalibur3
_diffrn_measurement_method       ' phi omega scans'
_diffrn_orient_matrix_UB_11      -0.0071967293
_diffrn_orient_matrix_UB_12      -0.0614387902
_diffrn_orient_matrix_UB_13      0.0323440912
_diffrn_orient_matrix_UB_21      -0.0468200383
_diffrn_orient_matrix_UB_22      0.0567147032
_diffrn_orient_matrix_UB_23      0.0269221818
_diffrn_orient_matrix_UB_31      -0.0890456894
_diffrn_orient_matrix_UB_32      -0.0222220404
_diffrn_orient_matrix_UB_33      -0.0140929494
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19298
_diffrn_reflns_resolution_max    0.75
_diffrn_reflns_theta_full        28.12
_diffrn_reflns_theta_max         28.12
_diffrn_reflns_theta_min         3.75
_diffrn_source_current           40
_diffrn_source_power             2
_diffrn_source_voltage           50
_diffrn_standards_interval_count 2
_diffrn_standards_interval_time  50
_exptl_absorpt_coefficient_mu    2.357
_exptl_absorpt_correction_T_max  0.798
_exptl_absorpt_correction_T_min  0.476
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.4927
_exptl_crystal_size_mid          0.1724
_exptl_crystal_size_min          0.1263
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         8941
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0337P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0651
_reflns_number_gt                7677
_reflns_number_total             8941
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7027163-File001.cif
_cod_data_source_block           Compound_11
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023402
_audit_creation_method_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_cell_measurement_resolution_max 0.76
_computing_cell_refinment_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_data_collection_reference
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_data_reduction_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_jhu_crystalization_method
;
;
_jhu_crystalization_solvent      'Ethanol, Hexane'
_jhu_diffraction_detector_distance 50
_jhu_quality_factor              1