Tosyl esters of cinchonidine and cinchonine alkaloids: the structure–reactivity relationship in the hydrolysis to 9-epibases
Karczmarzyk, Zbigniew; Lipińska, Teodozja M.; Wysocki, Waldemar; Denisiuk, Monika; Piechocka, Katarzyna; Acta Crystallographica Section C 67 (2011) o346–o349; doi:10.1107/S0108270111027272

data_2018236
_publ_section_title
;
 Tosyl esters of cinchonidine and cinchonine alkaloids: the
 structure--reactivity relationship in the hydrolysis to 9-epibases
;
_journal_coeditor_code           YF3003
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o346
_journal_page_last               o349
_journal_paper_doi               10.1107/S0108270111027272
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C26 H28 N2 O3 S'
_chemical_formula_moiety         'C26 H28 N2 O3 S'
_chemical_formula_sum            'C26 H28 N2 O3 S'
_chemical_formula_weight         448.56
_chemical_melting_point_gt       447
_chemical_melting_point_lt       448
_chemical_name_systematic
;
<i>O</i>-Tosyl cinchonine
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8350(13)
_cell_length_b                   17.7364(16)
_cell_length_c                   18.6632(17)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.24
_cell_measurement_theta_min      9.91
_cell_volume                     2262.5(5)
_computing_cell_refinement       'KM4B8 (Ga\/ldecki <i>et al.</i>, 1996)'
_computing_data_collection       'KM4B8 (Ga\/ldecki <i>et al.</i>, 1996)'
_computing_data_reduction        'DATAPROC (Ga\/ldecki <i>et al.</i>, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare <i>et al.</i>, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Kuma KM-4 four-circle'
_diffrn_measurement_method       \w-2\q
_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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2806
_diffrn_reflns_theta_full        80.31
_diffrn_reflns_theta_max         80.31
_diffrn_reflns_theta_min         3.44
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.518
_exptl_absorpt_correction_T_max  0.847
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
(North <i>et al.</i>, 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         2723
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0509
_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^)+(0.1133P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1765
_reflns_number_gt                1710
_reflns_number_total             2723
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            yf3003.cif
_cod_data_source_block           II
_cod_database_code               2018236