Synthesis and antimalarial evaluation of amide and urea derivatives based on the thiaplakortone A natural product scaffold.
Schwartz, Brett D.; Skinner-Adams, Tina S; Andrews, Katherine T.; Coster, Mark J.; Edstein, Michael D.; MacKenzie, Donna; Charman, Susan A.; Koltun, Maria; Blundell, Scott; Campbell, Anna; Pouwer, Rebecca H.; Quinn, Ronald J.; Beattie, Karren D.; Healy, Peter C.; Davis, Rohan A.; Organic & biomolecular chemistry 13 (2015) 1558–1570; doi:10.1039/c4ob01849d

data_7154214
_publ_section_title
;
 Synthesis and antimalarial evaluation of amide and urea derivatives based
 on the thiaplakortone A natural product scaffold.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1558
_journal_page_last               1570
_journal_paper_doi               10.1039/c4ob01849d
_journal_volume                  13
_journal_year                    2015
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C12 H12 N3 O4 S, Cl, 2(H2 O)'
_chemical_formula_sum            'C12 H16 Cl N3 O6 S'
_chemical_formula_weight         365.80
_chemical_name_common            'Thiaplakortone A hydrochoride dihydrate'
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_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_update_record
;
2014-04-23 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.5655(5)
_cell_length_b                   8.3351(3)
_cell_length_c                   26.0998(10)
_cell_measurement_reflns_used    2695
_cell_measurement_temperature    223.1(3)
_cell_measurement_theta_max      31.9850
_cell_measurement_theta_min      3.6560
_cell_volume                     3168.6(2)
_computing_cell_refinement       'CrysAlis Pro'
_computing_data_collection       'CrysAlis Pro(Oxford Diffraction, 2012)'
_computing_data_reduction        'CrysAlis Pro'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009), Westrip, 2010)'
_computing_structure_refinement
'TeXSan (Molecular Structure Corporation, 2001), SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      223.1(3)
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8729
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent, 2012),
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+2.2268P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                2950
_reflns_number_total             3640
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c4ob01849d2.cif
_cod_data_source_block           1_1099rd24_RAD212
_cod_depositor_comments
'Adding full bibliography for 7154214--7154215.cif.'
_cod_database_code               7154214