Asymmetric synthesis of (+)-loline, a pyrrolizidine alkaloid from rye grass and tall fescue
Blakemore, Paul R.; Kim, Sung-Kee; Schulze, Volker K.; White, James D.; Yokochi, Alexandre F. T.; Journal of the Chemical Society, Perkin Transactions 1  (2001) 1831–; doi:10.1039/b103936a

data_7216881
_publ_section_title
;
 Asymmetric synthesis of (+)-loline, a pyrrolizidine alkaloid from rye
 grass and tall fescue
;
_journal_issue                   15
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1831
_journal_paper_doi               10.1039/b103936a
_journal_year                    2001
_chemical_formula_sum            'C13 H25 N O4 Si'
_chemical_formula_weight         287.43
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 98.72(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.546(1)
_cell_length_b                   6.262(1)
_cell_length_c                   35.155(3)
_cell_measurement_reflns_used    92
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      24.734
_cell_measurement_theta_min      5.093
_cell_volume                     3165.2(6)
_computing_cell_refinement       'XSCANS V2.20'
_computing_data_collection       'XSCANS V2.20'
_computing_data_reduction        'XSCANS V2.20'
_computing_molecular_graphics    'ORTEP-III for windows'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SHELXS-90
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.553
_diffrn_measured_fraction_theta_max 0.553
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            3443
_diffrn_reflns_theta_full        67.55
_diffrn_reflns_theta_max         67.55
_diffrn_reflns_theta_min         5.09
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.401
_exptl_absorpt_correction_T_max  0.9452
_exptl_absorpt_correction_T_min  0.7821
_exptl_absorpt_correction_type   Psi-scans
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0971P)^2^+1.7325P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                2866
_reflns_number_total             3006
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b103936a.txt
_cod_data_source_block           VS060299
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      C2
_cod_database_code               7216881