Jatrophane diterpenes as inhibitors of chikungunya virus replication: structure-activity relationship and discovery of a potent lead.
Nothias-Scaglia, Louis-Félix; Retailleau, Pascal; Paolini, Julien; Pannecouque, Christophe; Neyts, Johan; Dumontet, Vincent; Roussi, Fanny; Leyssen, Pieter; Costa, Jean; Litaudon, Marc; Journal of natural products 77 (2014) 1505–1512; doi:10.1021/np500271u

data_1516619
_publ_section_title
;
 Jatrophane diterpenes as inhibitors of chikungunya virus replication:
 structure-activity relationship and discovery of a potent lead.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1505
_journal_page_last               1512
_journal_paper_doi               10.1021/np500271u
_journal_volume                  77
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C32 H44 O13'
_chemical_formula_sum            'C32 H44 O13'
_chemical_formula_weight         636.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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-2012
_cell_angle_alpha                90.00
_cell_angle_beta                 101.153(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3186(3)
_cell_length_b                   15.8687(4)
_cell_length_c                   20.1536(14)
_cell_measurement_reflns_used    8246
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      67.7
_cell_measurement_theta_min      2.2
_cell_volume                     3551.5(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-2012 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL-2012 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al, 1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0819
_diffrn_reflns_Laue_measured_fraction_full 0.928
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18543
_diffrn_reflns_point_group_measured_fraction_full 0.740
_diffrn_reflns_point_group_measured_fraction_max 0.787
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         65.089
_diffrn_reflns_theta_min         3.571
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  0.820
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1344 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.10(9)
_refine_ls_extinction_coef       0.0009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     834
_refine_ls_number_reflns         9522
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.1623
_refine_ls_R_factor_gt           0.0640
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0988P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.2267
_reflns_Friedel_coverage         0.535
_reflns_Friedel_fraction_full    0.538
_reflns_Friedel_fraction_max     0.572
_reflns_number_gt                4180
_reflns_number_total             9522
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np500271u_si_003.cif
_cod_data_source_block           Compound_2
_cod_depositor_comments
'Adding full bibliography for 1516618--1516621.cif.'
_cod_database_code               1516619
_shelxl_version_number           2012-9
_shelx_res_checksum              72853
_shelx_hkl_checksum              82684