Intramolecular Hydroamination of Aminoalkenes by Calcium and Magnesium Complexes: A Synthetic and Mechanistic Study
Mark R. Crimmin; Merle Arrowsmith; Anthony G. M. Barrett; Ian J. Casely; Michael S. Hill; Panayiotis A. Procopiou; Journal of the American Chemical Society 131 (2009) 9670–9685; doi:10.1021/ja9003377

data_4104695
_publ_section_title
;
 Intramolecular Hydroamination of Aminoalkenes by Calcium and Magnesium
 Complexes: A Synthetic and Mechanistic Study
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9670
_journal_page_last               9685
_journal_paper_doi               10.1021/ja9003377
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C11 H16 N, Cl'
_chemical_formula_sum            'C11 H16 Cl N'
_chemical_formula_weight         197.7
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2007-01-19T14:39:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9585(4)
_cell_length_b                   7.5081(4)
_cell_length_c                   18.6463(10)
_cell_measurement_reflns_used    38761
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      3.395
_cell_measurement_wavelength     0.71073
_cell_volume                     1114.18(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.98675E-2
_diffrn_orient_matrix_UB_12      -0.119564
_diffrn_orient_matrix_UB_13      -0.232524E-1
_diffrn_orient_matrix_UB_21      -0.644666E-1
_diffrn_orient_matrix_UB_22      0.448163E-1
_diffrn_orient_matrix_UB_23      -0.423421E-1
_diffrn_orient_matrix_UB_31      0.107401
_diffrn_orient_matrix_UB_32      0.378855E-1
_diffrn_orient_matrix_UB_33      -0.232948E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13647
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0692P)^2^+0.2588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1287
_reflns_number_gt                1683
_reflns_number_total             2174
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9003377_si_002.cif
_cod_data_source_block           jan407
_cod_database_code               4104695