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_1557203
_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         'C21 H26 O6'
_chemical_formula_sum            'C21 H26 O6'
_chemical_formula_weight         374.42
_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             2019-05-17
_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                   8.03150(10)
_cell_length_b                   8.3527(2)
_cell_length_c                   27.8078(5)
_cell_measurement_reflns_used    12478
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      77.1990
_cell_measurement_theta_min      5.5090
_cell_volume                     1865.48(6)
_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      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_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   -123.00 -32.00   0.50    0.06    --  -46.62 -23.00 -42.00  182
  2  \w   -173.00 -70.00   0.50    0.50    -- -100.00-127.00 -98.00  206
  3  \w   -173.00 -83.00   0.50    0.50    -- -100.00-101.00 156.00  180
  4  \w   -176.00 -85.00   0.50    0.50    -- -100.00 -23.00 -42.00  182
  5  \w     34.00 110.00   0.50    0.50    --  107.00-101.00 156.00  152
  6  \w    -95.00 -11.00   0.50    0.06    --  -46.62 125.00 -90.00  168
  7  \w     15.00  95.00   0.50    0.06    --   46.62-125.00   0.00  160
  8  \w     34.00 125.00   0.50    0.50    --  107.00 -61.00 -30.00  182
  9  \w     83.00 178.00   0.50    0.50    --  107.00  77.00-120.00  190
 10  \w     34.00 125.00   0.50    0.50    --  107.00 -61.00 120.00  182
 11  \w     34.00 109.00   0.50    0.50    --  107.00 -94.00  90.00  150
 12  \w     76.00 178.00   0.50    0.50    --  107.00 125.00  30.00  204
 13  \w     32.00 123.00   0.50    0.50    --  107.00 -30.00 120.00  182
 14  \w   -119.00 -23.00   0.50    0.06    --  -46.62 -77.00  90.00  192
 15  \w   -120.00 -52.00   0.50    0.06    --  -46.62 -38.00-120.00  136
 16  \w   -119.00 -23.00   0.50    0.06    --  -46.62 -77.00-180.00  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      0.0462454000
_diffrn_orient_matrix_UB_12      0.1551835000
_diffrn_orient_matrix_UB_13      0.0268555000
_diffrn_orient_matrix_UB_21      0.0367915000
_diffrn_orient_matrix_UB_22      0.0826500000
_diffrn_orient_matrix_UB_23      -0.0483989000
_diffrn_orient_matrix_UB_31      -0.1823293000
_diffrn_orient_matrix_UB_32      0.0558313000
_diffrn_orient_matrix_UB_33      -0.0030418000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            18993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.516
_diffrn_reflns_theta_min         3.178
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74926
_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    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1502 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.5131P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                3733
_reflns_number_total             3856
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00634_si_005.cif
_cod_data_source_block           wangr_190424_2
_cod_database_code               1557203
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.795
_reflns_odcompleteness_completeness 99.95
_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:
 C11(H11), C4(H4), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B), C12(H12A,H12B), C3(H3A,H3B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C19(H19), C17(H17)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C23(H23A,H23B,H23C), C26(H26A,H26B,H26C)
2.e Idealised tetrahedral OH refined as rotating group:
 O25(H25)
;
_shelx_res_checksum              68101
_shelx_hkl_checksum              46232
_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 1.533
_oxdiff_exptl_absorpt_empirical_full_min 0.716