Synthesis of Polyhydroxylated Quinolizidines and Azaspiro[4.5]decanes from d-Xylose.
Malik, Michał; Witkowski, Grzegorz; Ceborska, Magdalena; Jarosz, Sławomir; Organic letters 15 (2013) 6214–6217; doi:10.1021/ol403063v

data_1513235
_publ_section_title
;
 Synthesis of Polyhydroxylated Quinolizidines and Azaspiro[4.5]decanes
 from d-Xylose.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6214
_journal_page_last               6217
_journal_paper_doi               10.1021/ol403063v
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C21 H26 F3 N O11'
_chemical_formula_sum            'C21 H26 F3 N O11'
_chemical_formula_weight         525.43
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.127(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3343(2)
_cell_length_b                   20.6369(4)
_cell_length_c                   7.8664(2)
_cell_measurement_temperature    100(2)
_cell_volume                     1154.63(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7691
_diffrn_reflns_theta_full        71.23
_diffrn_reflns_theta_max         71.23
_diffrn_reflns_theta_min         6.19
_exptl_absorpt_coefficient_mu    1.198
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4365
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0278
_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^)+(0.0503P)^2^+0.1808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0746
_reflns_number_gt                4293
_reflns_number_total             4365
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol403063v_si_001.cif
_cod_data_source_block           mm_1
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1513235