Antimalarial and Antiproliferative Cassane Diterpenes of Caesalpinia sappan.
Ma, Guoxu; Wu, Haifeng; Chen, Deli; Zhu, Nailiang; Zhu, Yindi; Sun, Zhonghao; Li, Pengfei; Yang, Junshan; Yuan, Jingquan; Xu, Xudong; Journal of natural products 78 (2015) 2364–2371; doi:10.1021/acs.jnatprod.5b00317

data_1532487
_publ_section_title
;
 Antimalarial and Antiproliferative Cassane Diterpenes of Caesalpinia
 sappan.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2364
_journal_page_last               2371
_journal_paper_doi               10.1021/acs.jnatprod.5b00317
_journal_volume                  78
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H32 O7'
_chemical_formula_sum            'C23 H32 O7'
_chemical_formula_weight         420.48
_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
_audit_creation_date             2015-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.77200(10)
_cell_length_b                   13.5369(2)
_cell_length_c                   16.5519(2)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      67.70
_cell_measurement_theta_min      2.67
_cell_volume                     2189.53(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12537
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.062
_diffrn_reflns_theta_min         4.219
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  0.8550
_exptl_absorpt_correction_T_min  0.8075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1512 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.14(4)
_refine_ls_extinction_coef       0.0030(4)
_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   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+0.2860P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1033
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                3736
_reflns_number_total             3804
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np5b00317_si_001.cif
_cod_data_source_block           cu_20141025a_0m
_cod_depositor_comments          'Adding full bibliography for 1532487.cif.'
_cod_database_code               1532487
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.855
_shelx_estimated_absorpt_t_min   0.807
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C14(H14), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C16(H16A,H16B),
 C17(H17A,H17B), C18(H18A,H18B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C23(H23A,H23B,H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'