Dimericursones A and B: two unprecedented hexacyclic dimeric diterpenoids from the root barks of Jatropha curcas.
Liu, Jie-Qing; Xu, Ying; Xiao, Qin; Huang, Jin-Di; Ma, Jun-Jie; Lian, Chen-Lei; Huang, Mei-Ying; Du, Zhen-Bo; Wang, Cui-Fang; Organic & biomolecular chemistry 16 (2018) 8305–8310; doi:10.1039/c8ob02082e

data_7156417
_publ_section_title
;
 Dimericursones A and B: two unprecedented hexacyclic dimeric diterpenoids
 from the root barks of Jatropha curcas.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8305
_journal_page_last               8310
_journal_paper_doi               10.1039/c8ob02082e
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         '2(C39 H42 O3), C4 H8 O2'
_chemical_formula_sum            'C82 H92 O8'
_chemical_formula_weight         1205.55
_chemical_name_systematic        'Dimericursone B'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-29 deposited with the CCDC.
2018-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.896(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8979(3)
_cell_length_b                   22.3751(8)
_cell_length_c                   16.4276(5)
_cell_measurement_reflns_used    5248
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.5010
_cell_measurement_theta_min      4.6450
_cell_volume                     3499.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     20.00 104.00   1.00    1.00    --   36.14  57.00 -30.00   84
  2  \w     54.00  80.00   1.00    1.00    --   36.14  57.00   0.00   26
  3  \w      9.00  52.00   1.00    1.00    --   36.14 -19.00 120.00   43
  4  \w     99.00 125.00   1.00    2.50    --  108.00 -50.00 150.00   26
  5  \w     99.00 162.00   1.00    2.50    --  108.00  50.00  90.00   63
  6  \w    122.00 147.00   1.00    2.50    --  108.00  63.00  30.00   25
  7  \w     78.00 178.00   1.00    2.50    --  108.00  25.00   0.00  100
  8  \w     67.00  99.00   1.00    1.00    --   36.14  57.00-180.00   32
  9  \w     20.00  52.00   1.00    1.00    --   36.14  57.00-180.00   32
 10  \w     23.00  64.00   1.00    1.00    --   36.14  77.00-180.00   41
 11  \w     45.00 122.00   1.00    2.50    --  108.00 -50.00   0.00   77
 12  \w     44.00  99.00   1.00    2.50    --  108.00 -63.00 -60.00   55
 13  \w     38.00  76.00   1.00    2.50    --  108.00-111.00 -30.00   38
 14  \w     15.00  47.00   1.00    1.00    --   36.14 -57.00 -90.00   32
 15  \w     40.00  89.00   1.00    2.50    --  108.00 -50.00 150.00   49
 16  \w     38.00 133.00   1.00    2.50    --  108.00 -91.00 150.00   95
 17  \w     19.00  88.00   1.00    1.00    --   36.14-125.00  60.00   69
 18  \w    -14.00  12.00   1.00    1.00    --   36.14 -57.00 -90.00   26
 19  \w     26.00  77.00   1.00    1.00    --   36.14 -99.00-150.00   51
 20  \w    -27.00  57.00   1.00    1.00    --   36.14 -38.00  30.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0477791000
_diffrn_orient_matrix_UB_12      0.0635929000
_diffrn_orient_matrix_UB_13      0.0152283000
_diffrn_orient_matrix_UB_21      0.1510329000
_diffrn_orient_matrix_UB_22      0.0230337000
_diffrn_orient_matrix_UB_23      0.0121945000
_diffrn_orient_matrix_UB_31      -0.0336185000
_diffrn_orient_matrix_UB_32      0.0130088000
_diffrn_orient_matrix_UB_33      -0.0954410000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15730
_diffrn_reflns_point_group_measured_fraction_full 0.821
_diffrn_reflns_point_group_measured_fraction_max 0.794
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.790
_diffrn_reflns_theta_min         3.951
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 3021 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     869
_refine_ls_number_reflns         10882
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0731P)^2^+0.1843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1344
_reflns_Friedel_coverage         0.579
_reflns_Friedel_fraction_full    0.634
_reflns_Friedel_fraction_max     0.599
_reflns_number_gt                9425
_reflns_number_total             10882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02082e2.cif
_cod_data_source_block           exp_4971
_cod_depositor_comments
'Adding full bibliography for 7156416--7156417.cif.'
_cod_database_code               7156417
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.845
_shelx_estimated_absorpt_t_min   0.827
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H34A,H34B} of C34A, {H6BA,H6BB} of C6B, {H33B,H33C} of
  C33B, {H5BA,H5BB} of C5B, {H2A,H2B} of C2, {H9AA,H9AB} of C9A, {H8AA,H8AB} of
  C8A
 At 1.5 times of:
  All C(H,H,H) groups, {H37B,H38C} of C38B, {H2AA,H2AB} of C2A, {H1BA,H1BB}
  of C1B
2. Restrained distances
 C38A-H38A
 1 with sigma of 0.02
 C2A-H2AA
 1 with sigma of 0.02
 C38B-H37B
 1 with sigma of 0.02
 C38B-H38C
 1 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C17A(H17A), C9B(H9B), C8B(H8B), C5A(H5A), C19B(H19B), C6A(H6A), C35A(H35A),
 C4B(H4B), C32B(H32B), C4A(H4A)
3.b Secondary CH2 refined with riding coordinates:
 C33B(H33B,H33C), C34A(H34A,H34B), C6B(H6BA,H6BB), C5B(H5BA,H5BB), C9A(H9AA,
 H9AB), C8A(H8AA,H8AB), C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C11A(H11A), C28A(H28A), C28B(H28B), C15B(H15B), C21B(H21B), C22A(H22A),
 C33A(H33A), C34B(H34C)
3.d Idealised Me refined as rotating group:
 C36A(H36A,H36B,H36C), C16A(H16A,H16B,H16C), C24A(H24A,H24B,H24C), C31B(H31D,
 H31E,H31F), C36B(H36D,H36E,H36F), C16B(H16D,H16E,H16F), C31A(H31A,H31B,H31C),
 C24B(H24D,H24E,H24F), C25A(H25A,H25B,H25C), C4(H4C,H4D,H4E), C39B(H39D,H39E,
 H39F), C25B(H25D,H25E,H25F), C2B(H2BA,H2BB,H2BC), C39A(H39A,H39B,H39C),
 C1A(H1AA,H1AB,H1AC), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              88630
_olex2_date_sample_data_collection 1516521991.32
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.440
_oxdiff_exptl_absorpt_empirical_full_min 0.685