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_1511844
_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         'C25 H30 O8'
_chemical_formula_sum            'C25 H30 O8'
_chemical_formula_weight         458.49
_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             2012-02-08
_audit_creation_method
;
  Olex2 1.1
  (compiled Feb 15 2011 20:38:53, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.4761(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.88614(12)
_cell_length_b                   12.34409(7)
_cell_length_c                   14.84644(13)
_cell_measurement_reflns_used    25622
_cell_measurement_temperature    100.05(10)
_cell_measurement_theta_max      76.1432
_cell_measurement_theta_min      3.1748
_cell_volume                     2212.38(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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      100.05(10)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 10.4372
_diffrn_detector_type            'Oxford Diffraction Atlas'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -71.00   32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6052   57.0000   90.0000 103

  2 omega  -71.00   32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6052   57.0000 -150.0000 103

  3 omega -124.00  -80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6052  -99.0000 -150.0000 44

  4 omega -114.00  -79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6052  -99.0000  120.0000 35

  5 omega -116.00  -79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6052  -99.0000    0.0000 37

  6 omega    8.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6052  -99.0000  -60.0000 76

  7 omega   38.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 60

  8 omega   82.00  143.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 61

  9 omega   39.00   79.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 40

 10 omega   43.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 47

 11 omega   37.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -117.0000 -163.0000 26

 12 omega   54.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 31

 13 omega   70.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 26

 14 omega  122.00  148.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 26

 15 omega   35.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  120.0000 78

 16 omega   32.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -120.0000 77

 17 omega  109.00  147.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 38

 18 omega   62.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 34

 19 omega   35.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  150.0000 57

 20 omega  148.00  174.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000  -90.0000 26

 21 omega   75.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000    0.0000 41

 22 omega   40.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 36

 23 omega  109.00  140.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000  -90.0000 31

 24 omega   82.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 94

 25 omega   70.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -117.0000 -163.0000 41

 26 omega   27.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000 -150.0000 149

 27 omega -116.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6052  -57.0000  -30.0000 104

 28 omega -120.00   -8.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6052  -77.0000 -120.0000 112

 29 omega -120.00   -8.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6052  -77.0000   60.0000 112

 30 omega -116.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6052  -57.0000  120.0000 104

 31 omega   70.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6052  162.0000   74.0000 51

 32 omega -140.00  -28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   90.0000 112

 33 omega -140.00  -28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -180.0000 112

 34 omega -140.00  -28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -30.0000 112

 35 omega   82.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -30.0000 96

 36 omega   83.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 95

 37 omega   82.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 96

 38 omega   79.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 99

 39 omega   82.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 96

 40 omega   83.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 95

 41 omega   83.00  141.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 58

 42 omega   83.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 95
;
_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      -0.0066529000
_diffrn_orient_matrix_UB_12      0.0609300000
_diffrn_orient_matrix_UB_13      -0.0923590000
_diffrn_orient_matrix_UB_21      -0.0253160000
_diffrn_orient_matrix_UB_22      -0.1073084000
_diffrn_orient_matrix_UB_23      -0.0565486000
_diffrn_orient_matrix_UB_31      -0.1249341000
_diffrn_orient_matrix_UB_32      0.0185398000
_diffrn_orient_matrix_UB_33      -0.0232252000
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0073
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37837
_diffrn_reflns_theta_full        76.34
_diffrn_reflns_theta_max         76.34
_diffrn_reflns_theta_min         3.66
_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    0.850
_exptl_absorpt_correction_T_max  1.266
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.4149
_exptl_crystal_size_mid          0.1458
_exptl_crystal_size_min          0.1287
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.9601P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                4489
_reflns_number_total             4619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np300750q_si_002.cif
_cod_data_source_block           cs1833
_cod_database_code               1511844
_chemical_oxdiff_formula         'C21 H24 O8'
_chemical_oxdiff_usercomment     'Liva/Kingston (LH-215-235-3)'