3,4- seco-Norclerodane Diterpenoids from the Roots of Polyalthia laui.
Yu, Zhang-Xin; Zheng, Cai-Juan; Chen, Guang-Ying; Huang, Rong-Li; Zhou, Xue-Ming; Niu, Zhi-Gang; Li, Xiao-Bao; Han, Chang-Ri; Song, Xiao-Ping; Journal of natural products 82 (2019) 27–34; doi:10.1021/acs.jnatprod.8b00243

data_1553369
_publ_section_title
;
 3,4- seco-Norclerodane Diterpenoids from the Roots of Polyalthia laui.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              27
_journal_page_last               34
_journal_paper_doi               10.1021/acs.jnatprod.8b00243
_journal_volume                  82
_journal_year                    2019
_chemical_formula_moiety         'C20 H34 O4, H2 O'
_chemical_formula_sum            'C20 H34 O5'
_chemical_formula_weight         354.47
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.22366(9)
_cell_length_b                   15.7069(2)
_cell_length_c                   17.8026(2)
_cell_measurement_reflns_used    7670
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.1790
_cell_measurement_theta_min      3.7350
_cell_volume                     2019.91(4)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -76.00  -36.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0339  125.0000  -60.0000 40

  2 omega   72.00  101.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0339  141.0000  134.0000 29

  3 omega  -27.00   70.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0339  -57.0000 -150.0000 97

  4 omega  -37.00  -11.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   61.0000    0.0000 26

  5 omega   16.00   41.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -150.0000 25

  6 omega   85.00  121.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   30.0000 36

  7 omega   17.00   69.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   30.0000 52

  8 omega   23.00   53.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  -60.0000 30

  9 omega   84.00  151.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000 -180.0000 67

 10 omega   19.00   45.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  120.0000 26

 11 omega   60.00  121.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  120.0000 61

 12 omega   24.00   95.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000   90.0000 71

 13 omega   13.00   39.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000  -60.0000 26

 14 omega   93.00  142.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000  -60.0000 49

 15 omega  130.00  167.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000   30.0000 37

 16 omega   20.00   96.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  -30.0000 76

 17 omega   85.00  111.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000   30.0000 26

 18 omega   40.00   66.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   60.0000 26

 19 omega   17.00   45.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  -60.0000 28

 20 omega   67.00   92.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  -60.0000 25

 21 omega   92.00  118.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000 -150.0000 26

 22 omega   43.00   69.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -150.0000 26

 23 omega   16.00   41.00   1.0000   77.5200
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  150.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1583280000
_diffrn_orient_matrix_UB_12      0.0270503000
_diffrn_orient_matrix_UB_13      0.0528461000
_diffrn_orient_matrix_UB_21      0.0386533000
_diffrn_orient_matrix_UB_22      -0.0941661000
_diffrn_orient_matrix_UB_23      0.0184655000
_diffrn_orient_matrix_UB_31      0.1375738000
_diffrn_orient_matrix_UB_32      -0.0047036000
_diffrn_orient_matrix_UB_33      -0.0659771000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12160
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.302
_diffrn_reflns_theta_max         67.302
_diffrn_reflns_theta_min         3.753
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79205
_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
;
;
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description
;
;
_exptl_crystal_F_000             776
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1383 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0679P)^2^+0.2632P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3425
_reflns_number_total             3628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00243_si_004.cif
_cod_data_source_block           yzx-d42
_cod_original_cell_volume        2019.90(5)
_cod_database_code               1553369
_chemical_oxdiff_formula         'C1 O1'
_reflns_odcompleteness_completeness 99.95
_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, All O(H,H) groups
2.a Free rotating group:
 O25(H25A,H25B)
2.b Ternary CH refined with riding coordinates:
 C10(H10), C2(H2), C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C8(H8A,H8B), C3(H3A,H3B), C4(H4A,H4B), C12(H12A,
 H12B)
2.d Aromatic/amide H refined with riding coordinates:
 C14(H14)
2.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C21(H21A,H21B,
 H21C), C18(H18A,H18B,H18C)
2.f Idealised tetrahedral OH refined as rotating group:
 O20(H20), O19(H19)
;
_shelx_res_checksum              92955
_shelx_hkl_checksum              61741
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'