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_7156125
_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 unk
_chemical_formula_moiety         'C40 H68 O4'
_chemical_formula_sum            'C40 H68 O4'
_chemical_formula_weight         612.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                 117.810(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.0565(10)
_cell_length_b                   6.6594(2)
_cell_length_c                   26.3805(11)
_cell_measurement_reflns_used    5006
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      70.6780
_cell_measurement_theta_min      3.7840
_cell_volume                     3582.7(3)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  -75.00  -34.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  150.0000 41

  2 omega   -8.00   17.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -91.0000   79.0000 25

  3 omega  -82.00  -35.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   30.0000 47

  4 omega  -80.00  -53.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -150.0000 27

  5 omega  -53.00   20.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   99.0000   91.0000 73

  6 omega  -26.00   32.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000   60.0000 58

  7 omega  -16.00   80.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -38.0000   30.0000 96

  8 omega   -5.00   80.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000 -120.0000 85

  9 omega   -8.00   77.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  150.0000 85

 10 omega   44.00  110.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   64.0000 -116.5526 66

 11 omega  -15.00   79.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -38.0000  -90.0000 94

 12 omega   34.00  115.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000   90.0000 81

 13 omega   67.00   92.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  150.0000 25

 14 omega  120.00  178.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000  -60.0000 58

 15 omega   41.00   78.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -30.0000 37

 16 omega   39.00   65.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000 -120.0000 26

 17 omega   37.00   80.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  120.0000 43

 18 omega   88.00  176.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000 -120.0000 88

 19 omega   43.00   72.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -60.0000 29

 20 omega   49.00  102.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000   30.0000 53

 21 omega   64.00  109.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 45

 22 omega   37.00   63.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000    0.0000 26

 23 omega   91.00  116.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  150.0000 25

 24 omega   46.00   93.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000 -120.0000 47

 25 omega   56.00  115.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 59

 26 omega   72.00  139.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000   30.0000 67

 27 omega   40.00   82.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   90.0000 42

 28 omega   45.00  138.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -63.0000  150.0000 93

 29 omega   43.00  132.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -60.0000 89

 30 omega   47.00  167.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000 -150.0000 120
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0209037000
_diffrn_orient_matrix_UB_12      -0.1723825000
_diffrn_orient_matrix_UB_13      -0.0439301000
_diffrn_orient_matrix_UB_21      -0.0127782000
_diffrn_orient_matrix_UB_22      -0.1348944000
_diffrn_orient_matrix_UB_23      0.0412224000
_diffrn_orient_matrix_UB_31      -0.0714352000
_diffrn_orient_matrix_UB_32      0.0746866000
_diffrn_orient_matrix_UB_33      -0.0270654000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12075
_diffrn_reflns_theta_full        70.80
_diffrn_reflns_theta_max         70.80
_diffrn_reflns_theta_min         3.84
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72563
_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    1.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.1000
_exptl_crystal_size_mid          0.0700
_exptl_crystal_size_min          0.0400
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.248
_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   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         6729
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0713P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                5789
_reflns_number_total             6729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02991h2.cif
_cod_data_source_block           feidq_lhh_38
_cod_depositor_comments
'Adding full bibliography for 7156124--7156125.cif.'
_cod_database_code               7156125
_reflns_odcompleteness_completeness 99.94
_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:
 C5(H5), C9(H9), C12(H12), C15(H15), C25(H25), C29(H29), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,
 H11B), C14(H14A,H14B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B),
 C26(H26A,H26B), C27(H27A,H27B), C31(H31A,H31B), C32(H32A,H32B), C34(H34A,H34B)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,
 H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'