Antiproliferative and antiplasmodial dimeric phloroglucinols from Mallotus oppositifolius from the Madagascar Dry Forest (1).
Harinantenaina, Liva; Bowman, Jessica D.; Brodie, Peggy J.; Slebodnick, Carla; Callmander, Martin W.; Rakotobe, Etienne; Randrianaivo, Richard; Rasamison, Vincent E.; Gorka, Alexander; Roepe, Paul D.; Cassera, Maria B.; Kingston, David G. I.; Journal of natural products 76 (2013) 388–393; doi:10.1021/np300750q

data_1511845
_publ_section_title
;
 Antiproliferative and antiplasmodial dimeric phloroglucinols from
 Mallotus oppositifolius from the Madagascar Dry Forest (1).
;
_journal_issue                   3
_journal_name_full               'Journal of natural products'
_journal_page_first              388
_journal_page_last               393
_journal_paper_doi               10.1021/np300750q
_journal_volume                  76
_journal_year                    2013
_chemical_formula_moiety         'C21 H24 O8'
_chemical_formula_sum            'C21 H24 O8'
_chemical_formula_weight         404.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-07-14
_audit_creation_method
;
  Olex2 1.1
  (compiled Feb 15 2011 20:38:53, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.867(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4459(10)
_cell_length_b                   12.5596(9)
_cell_length_c                   16.2541(13)
_cell_measurement_reflns_used    2745
_cell_measurement_temperature    100.5
_cell_measurement_theta_max      76.1030
_cell_measurement_theta_min      3.5162
_cell_volume                     1863.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      100.5
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 10.4372
_diffrn_detector_type            'Oxford Diffraction Atlas'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
  1 omega  -48.00  -18.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6052  -17.0000   96.0000 30

  2 omega -101.00   -6.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6052  -77.0000 -120.0000 95

  3 omega  -66.00   35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6052   37.0000 -150.0000 101

  4 omega  -51.00   39.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6052   77.0000 -120.0000 90

  5 omega -101.00  -70.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6052  -54.0000  109.0000 31

  6 omega  -65.00  -13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6052  -54.0000  109.0000 52

  7 omega   45.00   73.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       39.6052   37.0000 -150.0000 28

  8 omega    1.00   29.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       39.6052   91.0000 -170.0000 28

  9 omega   13.00   39.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       39.6052   37.0000 -150.0000 26

 10 omega   63.00   94.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       39.6052 -140.0000 -144.0000 31

 11 omega  -58.00  -31.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -180.0000 27

 12 omega  -53.00  -28.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  162.0000 25

 13 omega  -56.00  -29.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  150.0000 27

 14 omega  -55.00  -28.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -74.0000   96.0000 27

 15 omega  -58.00  -31.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   90.0000 27

 16 omega  -61.00  -28.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   30.0000 33

 17 omega  -64.00  -30.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   60.0000 34

 18 omega  -55.00  -28.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 27

 19 omega  134.00  161.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 27

 20 omega   81.00  108.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 27

 21 omega   79.00  105.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 26

 22 omega   86.00  118.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  150.0000 32

 23 omega   85.00  166.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 81

 24 omega   86.00  145.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   60.0000 59

 25 omega   80.00  106.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 26

 26 omega   85.00  111.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 26

 27 omega   79.00  175.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 96

 28 omega  117.00  177.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 60

 29 omega   40.00  115.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -129.0000   28.0000 75

 30 omega   63.00  122.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -129.0000 -101.0000 59

 31 omega   79.00  105.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 26

 32 omega   93.00  118.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 25

 33 omega   79.00  105.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 26

 34 omega   85.00  112.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 27

 35 omega   95.00  165.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  125.0000 -120.0000 70

 36 omega   79.00  105.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 26

 37 omega   79.00  105.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 26

 38 omega   94.00  157.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  125.0000 -150.0000 63
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      -0.1660079000
_diffrn_orient_matrix_UB_12      -0.0058362000
_diffrn_orient_matrix_UB_13      -0.0405712000
_diffrn_orient_matrix_UB_21      -0.0277468000
_diffrn_orient_matrix_UB_22      0.0026260000
_diffrn_orient_matrix_UB_23      0.0893923000
_diffrn_orient_matrix_UB_31      -0.0066023000
_diffrn_orient_matrix_UB_32      0.1225638000
_diffrn_orient_matrix_UB_33      -0.0037045000
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15338
_diffrn_reflns_theta_full        72.50
_diffrn_reflns_theta_max         76.30
_diffrn_reflns_theta_min         4.51
_diffrn_source                   'Nova Micro-focus X-ray Source (Cu)'
_diffrn_source_target            Cu
_diffrn_source_type              'Nova Micro-focus X-ray Source (Cu)'
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_recrystallization_method
'Crystallized from methanol / ethyl acetate'
_exptl_crystal_size_max          0.2452
_exptl_crystal_size_mid          0.1217
_exptl_crystal_size_min          0.0066
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0919P)^2^+0.4875P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1695
_reflns_number_gt                2747
_reflns_number_total             3799
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np300750q_si_003.cif
_cod_data_source_block           cs1751
_cod_database_code               1511845
_chemical_oxdiff_formula         'C21 H24 O8'
_chemical_oxdiff_usercomment     'Liva/Kingston (LH-215-185-1-4-7)'
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13