19-nor-, 20-nor-, and tetranor-Halimane-Type Furanoditerpenoids from Croton crassifolius
Wang, Rong; Fan, Run-Zhu; Ni, Fu-Qiang; Sang, Jun; Xie, Xing-Lin; Luo, Si-Yuan; Tang, Gui-Hua; Yin, Sheng; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.9b00634

data_1557201
_publ_section_title
;
 19-nor-, 20-nor-, and tetranor-Halimane-Type Furanoditerpenoids from
 Croton crassifolius
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00634
_journal_year                    2020
_chemical_formula_moiety         'C23 H28 O8'
_chemical_formula_sum            'C23 H28 O8'
_chemical_formula_weight         432.45
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.3610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.99600(10)
_cell_length_b                   12.43040(10)
_cell_length_c                   14.2341(2)
_cell_measurement_reflns_used    16143
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.4610
_cell_measurement_theta_min      3.1220
_cell_volume                     1057.83(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -65.00  26.00   0.50    0.05    --  -46.62  63.00 -51.00  182
  2  \w   -119.00 -28.00   0.50    0.05    --  -46.62 -63.00 170.00  182
  3  \w   -118.00 -27.00   0.50    0.05    -- -100.00  63.00 -51.00  182
  4  \w   -173.00 -82.00   0.50    0.05    -- -100.00 -63.00 170.00  182
  5  \w     89.00 178.00   0.50    0.05    --  107.00  63.00 -51.00  178
  6  \w     34.00 125.00   0.50    0.05    --  107.00 -63.00 170.00  182
  7  \w   -119.00 -71.00   0.50    0.05    --  -46.62-125.00 -30.00   96
  8  \w   -119.00 -71.00   0.50    0.05    --  -46.62-125.00 150.00   96
  9  \w   -122.00 -31.00   0.50    0.05    --  -46.62 -19.00   0.00  182
 10  \w   -119.00 -30.00   0.50    0.05    --  -46.62 -57.00  60.00  178
 11  \w     29.00 120.00   0.50    0.05    --   46.62  63.00 -51.00  182
 12  \w    -25.00  65.00   0.50    0.05    --   46.62 -63.00 170.00  180
 13  \w     15.00  95.00   0.50    0.05    --   46.62-125.00-180.00  160
 14  \w   -173.00 -82.00   0.50    0.05    -- -100.00 -61.00  60.00  182
 15  \w   -172.00 -85.00   0.50    0.05    -- -100.00 -45.00-180.00  174
 16  \w   -176.00 -82.00   0.50    0.05    -- -100.00 -15.00-120.00  188
 17  \w   -175.00 -84.00   0.50    0.05    -- -100.00 -30.00  60.00  182
 18  \w   -172.00 -85.00   0.50    0.05    -- -100.00 -45.00  60.00  174
 19  \w   -172.00 -85.00   0.50    0.05    -- -100.00 -45.00 120.00  174
 20  \w   -172.00 -85.00   0.50    0.05    -- -100.00 -45.00  30.00  174
 21  \w     83.00 178.00   0.50    0.05    --  107.00  77.00   0.00  190
 22  \w     31.00 125.00   0.50    0.05    --  107.00 -15.00 -60.00  188
 23  \w     34.00 109.00   0.50    0.05    --  107.00 -94.00 150.00  150
 24  \w     34.00 125.00   0.50    0.05    --  107.00 -61.00-150.00  182
 25  \w     83.00 178.00   0.50    0.05    --  107.00  77.00  90.00  190
 26  \w     34.00 117.00   0.50    0.05    --  107.00-125.00 -60.00  166
 27  \w     34.00 109.00   0.50    0.05    --  107.00 -94.00 120.00  150
 28  \w     34.00 109.00   0.50    0.05    --  107.00 -94.00   0.00  150
 29  \w     34.00 131.00   0.50    0.05    --  107.00 -77.00 -30.00  194
 30  \w     90.00 178.00   0.50    0.05    --  107.00  61.00   0.00  176
 31  \w     90.00 178.00   0.50    0.05    --  107.00  61.00  60.00  176
 32  \w   -119.00 -62.00   0.50    0.05    --  -46.62 -77.00   0.00  114
 33  \w   -119.00 -23.00   0.50    0.05    --  -46.62 -77.00 -90.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2389798000
_diffrn_orient_matrix_UB_12      -0.0458427000
_diffrn_orient_matrix_UB_13      0.0015623000
_diffrn_orient_matrix_UB_21      -0.0532032000
_diffrn_orient_matrix_UB_22      -0.0782727000
_diffrn_orient_matrix_UB_23      0.0792057000
_diffrn_orient_matrix_UB_31      -0.0802996000
_diffrn_orient_matrix_UB_32      -0.0844475000
_diffrn_orient_matrix_UB_33      -0.0742089000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2125
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18599
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.971
_diffrn_reflns_theta_max         66.971
_diffrn_reflns_theta_min         3.114
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details
;
 Flack x determined using 1452 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3738
_refine_ls_number_restraints     217
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0971
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2491
_refine_ls_wR_factor_ref         0.2545
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3570
_reflns_number_total             3738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00634_si_006.cif
_cod_data_source_block           wangr_190314_2
_cod_database_code               1557201
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.919
_shelx_estimated_absorpt_t_min   0.784
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C15) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O24) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3.a Ternary CH refined with riding coordinates:
 C4(H4), C2(H2), C12(H12), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C3(H3A,H3B), C13(H13A,H13B), C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C18(H18), C19(H19)
3.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C23(H23A,H23B,H23C), C28(H28A,H28B,
 H28C)
3.e Idealised tetrahedral OH refined as rotating group:
 O29(H29)
;
_shelx_res_checksum              98162
_shelx_hkl_checksum              21782
_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 4.180
_oxdiff_exptl_absorpt_empirical_full_min 0.121