Diastereoselectivity Control of the Radical Carboazidation of Substituted Methylenecyclohexanes
Sylvaine Cren; Pascal Schär; Philippe Renaud; Kurt Schenk; Journal of Organic Chemistry 74 (2009) 2942–2946; doi:10.1021/jo900088x

data_4024469
_publ_section_title
;
Diastereoselectivity Control of the Radical Carboazidation of Substituted
Methylenecyclohexanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2942
_journal_page_last               2946
_journal_paper_doi               10.1021/jo900088x
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C13 H23 N1 O1'
_chemical_formula_sum            'C13 H23 N O'
_chemical_formula_weight         209.32
_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_author_name               'Kurt J. Schenk'
_audit_contact_author_address
;
   Kurt J. Schenk
   LCr1 - IPMC - FSB - EPFL
   Le Cubtron, Bureau 521
   Dorigny
   CH-1015 Lausanne
;
_audit_contact_author_email      Kurt.Schenk@EPFL.CH
_audit_contact_author_fax        '+41 (0)21 693 0504'
_audit_contact_author_phone      '+41 (0)21 693 0635'
_audit_creation_date             '2nd February 2008'
_audit_creation_method           'SHELXL-97 & Stoe X-Red'
_cell_angle_alpha                104.22(3)
_cell_angle_beta                 100.83(3)
_cell_angle_gamma                96.08(3)
_cell_formula_units_Z            4
_cell_length_a                   6.4933(13)
_cell_length_b                   13.379(3)
_cell_length_c                   15.515(3)
_cell_measurement_reflns_used    8621
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      29.52
_cell_measurement_theta_min      2.38
_cell_volume                     1266.8(5)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'SHELXtl (Bruker, 1996)'
_computing_publication_material  'SHELXtl (Bruker, 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_details      ' 180 frames, detector distance = 100 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8867
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.80
_diffrn_source_current           45
_diffrn_source_power             2.48
_diffrn_source_voltage           55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Stoe, X_Red32, Version 1.31 (2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelets
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.041(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0731P)^2^+0.2118P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1519
_reflns_number_gt                3289
_reflns_number_total             4596
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900088x_si_001.cif
_cod_data_source_block           PS5j
_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_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C13 H23 N1 O1'
_cod_database_code               4024469