Tandem semipinacol/Schmidt reaction leading to a versatile and efficient approach to azaquaternary alkaloid skeletons.
Gu, Peiming; Zhao, Yu-Ming; Tu, Yong Qiang; Ma, Yufei; Zhang, Fumin; Organic letters 8 (2006) 5271–5273; doi:10.1021/ol062116r

data_1506261
_publ_section_title
;
 Tandem semipinacol/Schmidt reaction leading to a versatile and efficient
 approach to azaquaternary alkaloid skeletons.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5271
_journal_page_last               5273
_journal_paper_doi               10.1021/ol062116r
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C12 H19 N O2'
_chemical_formula_weight         209.28
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.177(2)
_cell_length_b                   14.030(2)
_cell_length_c                   14.477(2)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    287(2)
_cell_measurement_theta_max      13.86
_cell_measurement_theta_min      6.29
_cell_volume                     2270.2(6)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      287(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
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_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3316
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        2.79
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0051(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2231
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                1140
_reflns_number_total             2231
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol062116rsi20060828_084329.cif
_cod_data_source_block           y2141
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2270.3(5)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1506261