Norcrassin A, a novel C<sub>16</sub> tetranorditerpenoid, and bicrotonol A, an unusual dimeric labdane-type diterpenoid, from the roots of Croton crassifolius.
Zhang, Zhan-Xin; Wu, Pei-Qian; Li, Hui-Hong; Qi, Feng-Ming; Fei, Dong-Qing; Hu, Qiao-Ling; Liu, Ying-Hong; Huang, Xiao-Ling; Organic & biomolecular chemistry 16 (2018) 1745–1750; doi:10.1039/c7ob02991h

data_7156124
_publ_section_title
;
 Norcrassin A, a novel C<sub>16</sub> tetranorditerpenoid, and bicrotonol
 A, an unusual dimeric labdane-type diterpenoid, from the roots of Croton
 crassifolius.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1745
_journal_page_last               1750
_journal_paper_doi               10.1039/c7ob02991h
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H22 O7'
_chemical_formula_sum            'C17 H22 O7'
_chemical_formula_weight         338.35
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-02-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-10-23 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.16871(17)
_cell_length_b                   8.25025(17)
_cell_length_c                   23.3395(4)
_cell_measurement_reflns_used    4096
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5500
_cell_measurement_theta_min      5.3980
_cell_volume                     1572.94(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
  1 omega  -61.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 25

  2 omega   28.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   90.0000 41

  3 omega  -22.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   90.0000 39

  4 omega  -27.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000   90.0000 25

  5 omega   71.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   60.0000 55

  6 omega   25.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000   30.0000 61

  7 omega   50.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   38.0000    0.0000 78

  8 omega   24.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  -60.0000 26

  9 omega   33.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -90.0000 38

 10 omega   88.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -90.0000 39

 11 omega  101.00  160.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   60.0000 59

 12 omega  117.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000 -120.0000 50

 13 omega   43.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   60.0000 39

 14 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000  -90.0000 26

 15 omega  100.00  165.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   90.0000 65

 16 omega  101.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -180.0000 75

 17 omega   39.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  -30.0000 48

 18 omega  103.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  120.0000 75

 19 omega  111.00  160.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -150.0000 49

 20 omega  117.00  142.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   30.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0392503000
_diffrn_orient_matrix_UB_12      -0.1771060000
_diffrn_orient_matrix_UB_13      -0.0158631000
_diffrn_orient_matrix_UB_21      0.1036301000
_diffrn_orient_matrix_UB_22      0.0167288000
_diffrn_orient_matrix_UB_23      -0.0548117000
_diffrn_orient_matrix_UB_31      0.1526135000
_diffrn_orient_matrix_UB_32      -0.0567835000
_diffrn_orient_matrix_UB_33      0.0331684000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5337
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         3.79
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(18)
_refine_ls_extinction_coef       0.0172(17)
_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   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0818P)^2^+0.1108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                2557
_reflns_number_total             2591
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02991h2.cif
_cod_data_source_block           lhh_41
_cod_depositor_comments
'Adding full bibliography for 7156124--7156125.cif.'
_cod_database_code               7156124
_reflns_odcompleteness_completeness 95.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_date_sample_data_collection 1399340241.9
_olex2_submission_special_instructions 'No special instructions were received'