Synthesis, in vitro and in vivo antimalarial assessment of sulfide, sulfone and vinyl amide-substituted 1,2,4-trioxanes prepared via thiol-olefin co-oxygenation (TOCO) of allylic alcohols.
Amewu, Richard; Gibbons, Peter; Mukhtar, Amira; Stachulski, Andrew V.; Ward, Stephen A.; Hall, Charlotte; Rimmer, Karen; Davies, Jill; Vivas, Livia; Bacsa, John; Mercer, Amy E.; Nixon, Gemma; Stocks, Paul A.; O'Neill, Paul M; Organic & biomolecular chemistry 8 (2010) 2068–2077; doi:10.1039/b924319d

data_7153299
_publ_section_title
;
 Synthesis, in vitro and in vivo antimalarial assessment of sulfide,
 sulfone and vinyl amide-substituted 1,2,4-trioxanes prepared via
 thiol-olefin co-oxygenation (TOCO) of allylic alcohols.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2068
_journal_page_last               2077
_journal_paper_doi               10.1039/b924319d
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C22 H37 N2 O4, H2 O, Cl'
_chemical_formula_sum            'C22 H39 Cl N2 O5'
_chemical_formula_weight         447.00
_chemical_name_common            RKA269
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2008-03-04 # Formatted by J.Bacsa
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.288(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.705(3)
_cell_length_b                   7.6876(13)
_cell_length_c                   16.257(3)
_cell_measurement_reflns_used    10985
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.0
_cell_volume                     2333.9(7)
_computing_cell_refinement       'SAINT v6.45a (Bruker, 2005)'
_computing_data_collection       'SMART v.5.632 (Bruker, 2005)'
_computing_data_reduction        'SAINT v6.45a (Bruker, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX detector'
_diffrn_measurement_method       '\w scans with a narrow frame width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14079
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_correction_T_min  0.9074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2007/4 (Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.771
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0730
_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^)+(0.0617P)^2^+3.6453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.1682
_reflns_number_gt                3573
_reflns_number_total             4241
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b924319d.txt
_cod_data_source_block           rka269
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7153299