Antiproliferative Constituents of the Roots of Ethiopian Podocarpus falcatus and Structure Revision of 2α-Hydroxynagilactone F and Nagilactone I.
Addo, Ermias Mekuria; Chai, Hee-Byung; Hymete, Ariaya; Yeshak, Mariamawit Yonathan; Slebodnick, Carla; Kingston, David G. I.; Rakotondraibe, L. Harinantenaina; Journal of natural products 78 (2015) 827–835; doi:10.1021/np501062f

data_1518894
_publ_section_title
;
 Antiproliferative Constituents of the Roots of Ethiopian Podocarpus
 falcatus and Structure Revision of 2\a-Hydroxynagilactone F and
 Nagilactone I.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              827
_journal_page_last               835
_journal_paper_doi               10.1021/np501062f
_journal_volume                  78
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H20 O6, H2 O'
_chemical_formula_sum            'C18 H22 O7'
_chemical_formula_weight         350.35
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.13350(10)
_cell_length_b                   8.36010(10)
_cell_length_c                   26.2049(5)
_cell_measurement_reflns_used    10445
_cell_measurement_temperature    99.90(14)
_cell_measurement_theta_max      74.5450
_cell_measurement_theta_min      5.4980
_cell_volume                     1562.78(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.90(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1587
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   16.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   57.0000   30.0000 99

  2 omega  125.00  151.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  121.0000  -66.0000 26

  3 omega  104.00  150.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  179.0000   30.0000 46

  4 omega  106.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  151.0000   94.0000 25

  5 omega  105.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  179.0000   60.0000 39

  6 omega   80.00  166.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   45.0000   60.0000 86

  7 omega  148.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000    0.0000  -90.0000 26

  8 omega   82.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000   90.0000 40

  9 omega   85.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -77.0000  150.0000 38

 10 omega   66.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000   30.0000 43

 11 omega   58.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -151.0000   50.0000 25

 12 omega   41.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000   90.0000 66

 13 omega   43.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000   90.0000 32

 14 omega   29.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -77.0000   30.0000 93

 15 omega   79.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   15.0000  150.0000 52

 16 omega   32.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000    0.0000 33

 17 omega   33.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000  -90.0000 34

 18 omega   45.00   71.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000 -150.0000 26

 19 omega   35.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000 -180.0000 100

 20 omega   80.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -121.0000 -149.0000 25

 21 omega   35.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000 -120.0000 30

 22 omega   37.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -180.0000 31

 23 omega   20.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000    0.0000  -90.0000 125

 24 omega   33.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419 -151.0000   50.0000 79

 25 omega   33.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000   90.0000 43

 26 omega   29.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -77.0000  150.0000 30

 27 omega   23.00   58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000   30.0000 35

 28 omega   28.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000   30.0000 79

 29 omega   14.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419 -121.0000 -149.0000 65

 30 omega  -29.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9419  -37.0000   60.0000 98

 31 omega  -71.00  -46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  121.0000  -66.0000 25

 32 omega   35.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  179.0000   30.0000 50

 33 omega   42.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  179.0000   60.0000 45

 34 omega  -89.00  -64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  151.0000   94.0000 25

 35 omega -108.00  -80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  -99.0000  -30.0000 28

 36 omega -112.00  -87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419 -151.0000   50.0000 25

 37 omega -126.00  -80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  -99.0000  120.0000 46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0054646000
_diffrn_orient_matrix_UB_12      0.1756020000
_diffrn_orient_matrix_UB_13      -0.0178202000
_diffrn_orient_matrix_UB_21      0.0220326000
_diffrn_orient_matrix_UB_22      -0.0560379000
_diffrn_orient_matrix_UB_23      -0.0556626000
_diffrn_orient_matrix_UB_31      -0.2147712000
_diffrn_orient_matrix_UB_32      -0.0011751000
_diffrn_orient_matrix_UB_33      -0.0061667000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18271
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.877
_diffrn_reflns_theta_min         3.373
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method 'Grown from CH3OH'
_exptl_crystal_size_max          0.2002
_exptl_crystal_size_mid          0.1846
_exptl_crystal_size_min          0.0543
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1261 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0487P)^2^+0.3174P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0834
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3086
_reflns_number_total             3207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np501062f_si_003.cif
_cod_data_source_block           cs2143
_cod_depositor_comments
'Adding full bibliography for 1518892--1518894.cif.'
_cod_database_code               1518894
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C18 H20 O6 H2O'
_chemical_oxdiff_usercomment     'Yixi Liu / David Kingston (ERXR-1)'
_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
2.a Ternary CH refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_olex2_submission_original_sample_id ERXR-1
_olex2_submission_special_instructions 'No special instructions were received'