Diastereoselective Control Through Hydrogen Bonding in the Aziridination of the Chiral Allylic Alcohols by Acetoxyaminoquinazolinone
Cakici, Murat; Karabuga, Semistan; Kilic, Hamdullah; Ulukanli, Sabri; Şahin, Ertan; Sevin, Fatma; The Journal of Organic Chemistry 74 (2009) 9452–9459; doi:10.1021/jo902092s

data_4028966
_publ_section_title
;
 Diastereoselective Control Through Hydrogen Bonding in the Aziridination
 of the Chiral Allylic Alcohols by Acetoxyaminoquinazolinone
;
_journal_issue                   24
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              9452
_journal_page_last               9459
_journal_paper_doi               10.1021/jo902092s
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C16 H21 N3 O2'
_chemical_formula_sum            'C16 H21 N3 O2'
_chemical_formula_weight         287.36
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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             2009-07-01T17:23:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                72.415(4)
_cell_angle_beta                 87.435(4)
_cell_angle_gamma                85.548(5)
_cell_formula_units_Z            2
_cell_length_a                   8.2049(2)
_cell_length_b                   8.91260(10)
_cell_length_c                   11.02020(10)
_cell_measurement_reflns_used    1783
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3678
_cell_measurement_theta_min      2.4025
_cell_volume                     765.71(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution
;
        ????
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device
;
        RAXIS conversion
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0023
_diffrn_orient_matrix_UB_12      0.0167
_diffrn_orient_matrix_UB_13      -0.1211
_diffrn_orient_matrix_UB_21      -0.114
_diffrn_orient_matrix_UB_22      -0.0302
_diffrn_orient_matrix_UB_23      0.0017
_diffrn_orient_matrix_UB_31      0.0049
_diffrn_orient_matrix_UB_32      0.0939
_diffrn_orient_matrix_UB_33      0.0152
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.054
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16471
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        26.45
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_min         2.4
_diffrn_standards_number         20
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.093
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0881P)^2^+0.0209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1645
_refine_ls_wR_factor_ref         0.1907
_reflns_number_gt                2008
_reflns_number_total             3136
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo902092ssup2.cif
_cod_data_source_block           shelxlhkilic-mcakici
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        765.71(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4028966