One-Pot Conversions of Olefins to Cyclic Carbonates and Secondary Allylic and Homoallylic Amines to Cyclic Carbamates
Stephen G. Davies; Ai M. Fletcher; Wataru Kurosawa; James A. Lee; Giovanna Poce; Paul M. Roberts; James E. Thomson; David M. Williamson; Journal of Organic Chemistry 75 (2010) 7745–7756; doi:10.1021/jo101614f

data_4025823
_publ_contact_author_address
;Department of Chemistry
Chemistry Research Laboratory
University of Oxford
Mansfield Road
Oxford
OX1 3TA, U.K.
;
_publ_contact_author_email       steve.davies@chem.ox.ac.uk
_publ_contact_author_fax         '+44 1865 275633'
_publ_contact_author_name        'Stephen G. Davies'
_publ_contact_author_phone       '+44 1865 275695'
_publ_section_title
;
 One-Pot Conversions of Olefins to Cyclic Carbonates and Secondary Allylic
 and Homoallylic Amines to Cyclic Carbamates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7745
_journal_page_last               7756
_journal_paper_doi               10.1021/jo101614f
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C14 H19 N1 O3'
_chemical_formula_sum            'C14 H19 N O3'
_chemical_formula_weight         249.31
_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
_audit_creation_date             09-09-14
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                101.4022(16)
_cell_angle_beta                 104.9826(16)
_cell_angle_gamma                90.623(2)
_cell_formula_units_Z            4
_cell_length_a                   9.6645(4)
_cell_length_b                   11.3513(4)
_cell_length_c                   12.7583(5)
_cell_measurement_reflns_used    5386
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1322.54(9)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9400
_diffrn_reflns_theta_full        25.061
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         5.162
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.50
_refine_diff_density_min         -1.33
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1635
_refine_ls_R_factor_gt           0.1331
_refine_ls_shift/su_max          0.000066
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 2.42 2.52 1.48 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1712
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1344
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3111
_reflns_number_total             5982
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.04
_oxford_diffrn_Wilson_scale      5.06
_oxford_refine_ls_r_factor_ref   0.1269
_oxford_refine_ls_scale          0.645(10)
_oxford_reflns_number_all        4285
_oxford_reflns_threshold_expression_ref I>2.5\s(I)
_oxford_structure_analysis_title '9011415 SGD260a'
_cod_data_source_file            jo101614f_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C14 H19 N1 O3'
_cod_database_code               4025823