C-Alkylation of Chiral Tropane- and Homotropane-Derived Enamines
David M. Hodgson; Andrew Charlton; Robert S. Paton; Amber L. Thompson; Journal of Organic Chemistry 78 (2013) 1508–1518; doi:10.1021/jo3025972

data_4027964
_publ_contact_author             'David M. Hodgson'
_publ_contact_author_email       david.hodgson@chem.ox.ac.uk
_publ_section_title
;
 C-Alkylation of Chiral Tropane- and Homotropane-Derived Enamines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1508
_journal_page_last               1518
_journal_paper_doi               10.1021/jo3025972
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H19 N1 O1'
_chemical_formula_sum            'C11 H19 N O'
_chemical_formula_weight         181.28
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             12-09-04
_audit_creation_method           CRYSTALS_ver_14.40
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9046(1)
_cell_length_b                   8.2614(1)
_cell_length_c                   21.5105(1)
_cell_measurement_reflns_used    37004
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     1049.29(2)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            50455
_diffrn_reflns_theta_full        76.640
_diffrn_reflns_theta_max         76.640
_diffrn_reflns_theta_min         4.110
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.11
_refine_ls_abs_structure_details 'Flack (1983), 890 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.04(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.0007193
_refine_ls_shift/su_mean         0.0000473
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.16P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0676
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0676
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                2173
_reflns_number_total             2205
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.30
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0254
_oxford_refine_ls_scale          10.7(4)
_oxford_reflns_number_all        2198
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 6441-2
_cod_data_source_file            jo3025972_si_002_3.cif
_cod_data_source_block           18-2
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C11 H19 N1 O1'
_cod_database_code               4027964
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE N   (   1,X'S) H   (  11,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) H   (  32,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) H   (  73,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) H   (  93,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) H   ( 103,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
END                                                                             
;