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_1557205
_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_absolute_configuration ad
_chemical_formula_moiety         'C23 H28 O8'
_chemical_formula_sum            'C23 H28 O8'
_chemical_formula_weight         432.45
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.90190(10)
_cell_length_b                   10.29550(10)
_cell_length_c                   25.9952(4)
_cell_measurement_reflns_used    18716
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.1920
_cell_measurement_theta_min      3.3940
_cell_volume                     2114.81(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     31.00 120.00   0.50    0.05    --   46.62  53.00 -27.00  178
  2  \w   -173.00 -76.00   0.50    0.20    -- -100.00-117.00 -43.00  194
  3  \w     87.00 178.00   0.50    0.20    --  107.00  68.00 163.00  182
  4  \w   -119.00 -71.00   0.50    0.05    --  -46.62-125.00-180.00   96
  5  \w   -119.00 -71.00   0.50    0.05    --  -46.62-125.00 -30.00   96
  6  \w    -25.00  63.00   0.50    0.05    --   46.62 -57.00 -30.00  176
  7  \w   -114.00 -27.00   0.50    0.20    -- -100.00  45.00  90.00  174
  8  \w     32.00 123.00   0.50    0.20    --  107.00 -30.00   0.00  182
  9  \w     31.00 125.00   0.50    0.20    --  107.00 -15.00   0.00  188
 10  \w     34.00 109.00   0.50    0.20    --  107.00 -94.00-150.00  150
 11  \w     34.00 117.00   0.50    0.20    --  107.00-125.00  90.00  166
 12  \w     31.00 125.00   0.50    0.20    --  107.00 -15.00-180.00  188
 13  \w     93.00 178.00   0.50    0.20    --  107.00  45.00 150.00  170
 14  \w     34.00 123.00   0.50    0.20    --  107.00 -53.00-171.00  178
 15  \w   -119.00 -71.00   0.50    0.05    --  -46.62-125.00  60.00   96
 16  \w     31.00 120.00   0.50    0.05    --   46.62  57.00  60.00  178
 17  \w     23.00 120.00   0.50    0.05    --   46.62  77.00-150.00  194
 18  \w   -173.00-140.00   0.50    0.20    -- -100.00 -68.00  30.00   66
;
_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      0.0201094000
_diffrn_orient_matrix_UB_12      0.0154560000
_diffrn_orient_matrix_UB_13      -0.0586526000
_diffrn_orient_matrix_UB_21      -0.1496500000
_diffrn_orient_matrix_UB_22      0.0957803000
_diffrn_orient_matrix_UB_23      -0.0008172000
_diffrn_orient_matrix_UB_31      0.1232696000
_diffrn_orient_matrix_UB_32      0.1138834000
_diffrn_orient_matrix_UB_33      0.0086061000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            20943
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.116
_diffrn_reflns_theta_min         3.400
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71010
_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             920
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1672 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0509P)^2^+0.8917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4062
_reflns_number_total             4161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00634_si_004.cif
_cod_data_source_block           wangr_41_190419
_cod_database_code               1557205
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.919
_shelx_estimated_absorpt_t_min   0.784
_reflns_odcompleteness_completeness 99.88
_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.a Ternary CH refined with riding coordinates:
 C4(H4), C12(H12), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C13(H13A,H13B), C7(H7A,H7B), C8(H8A,H8B), C3(H3A,H3B), C9(H9A,
 H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C19(H19), C18(H18)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C28(H28A,H28B,H28C), C23(H23A,H23B,H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O30(H30)
;
_shelx_res_checksum              1208
_shelx_hkl_checksum              89053
_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 3.592
_oxdiff_exptl_absorpt_empirical_full_min 0.800