Asymmetric Synthesis of the Tropane Alkaloid (+)-Pseudococaine via Ring-Closing Iodoamination.
Brock, E. Anne; Davies, Stephen G.; Lee, James A.; Roberts, Paul M.; Thomson, James E.; Organic letters 14 (2012) 4278–4281; doi:10.1021/ol3020607

data_1508359
_publ_section_title
;
 Asymmetric Synthesis of the Tropane Alkaloid (+)-Pseudococaine via
 Ring-Closing Iodoamination.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4278
_journal_page_last               4281
_journal_paper_doi               10.1021/ol3020607
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H33 N1 O4'
_chemical_formula_sum            'C22 H33 N O4'
_chemical_formula_weight         375.51
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 103.0723(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5891(2)
_cell_length_b                   10.1907(2)
_cell_length_c                   20.7473(4)
_cell_measurement_reflns_used    5116
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     2180.83(7)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 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 0.989
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9654
_diffrn_reflns_theta_full        26.952
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         5.135
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9464
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         4301
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.0002219
_refine_ls_shift/su_mean         0.0000141
_refine_ls_structure_factor_coef Fsqd
_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: 
 13.2 20.0 10.2 2.75 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1095
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1095
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                3490
_reflns_number_total             5228
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.10
_oxford_diffrn_Wilson_scale      7.00
_oxford_refine_ls_r_factor_ref   0.0566
_oxford_refine_ls_scale          0.3774(6)
_oxford_reflns_number_all        4301
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            ol3020607_si_002.cif
_cod_data_source_block           13
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_formula_sum        'C22 H33 N1 O4'
_cod_database_code               1508359