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_1516618
_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 ad
_chemical_formula_moiety         'C35 H42 O13, 0.20(H2 O)'
_chemical_formula_sum            'C35 H42.4 O13.2'
_chemical_formula_weight         674.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2634(3)
_cell_length_b                   15.8807(5)
_cell_length_c                   21.1556(14)
_cell_measurement_reflns_used    7981
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      2.1
_cell_volume                     3784.1(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_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            35387
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.128
_diffrn_reflns_theta_min         3.480
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       stick
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1521 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6866
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4546
_reflns_number_total             6866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np500271u_si_005.cif
_cod_data_source_block           Compound_4
_cod_depositor_comments
'Adding full bibliography for 1516618--1516621.cif.'
_cod_original_formula_sum        'C35 H42.40 O13.20'
_cod_database_code               1516618
_shelx_estimated_absorpt_t_min   0.928
_shelx_estimated_absorpt_t_max   0.928
_shelxl_version_number           2012-9
_shelx_res_checksum              65555
_shelx_hkl_checksum              22598