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_1553370
_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_absolute_configuration unk
_chemical_formula_moiety         'C19 H30 O5'
_chemical_formula_sum            'C19 H30 O5'
_chemical_formula_weight         338.43
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.626(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2372(2)
_cell_length_b                   25.7913(7)
_cell_length_c                   9.2037(2)
_cell_measurement_reflns_used    8091
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.1430
_cell_measurement_theta_min      3.4060
_cell_volume                     1908.02(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   10.00  114.00   1.0000   30.8800
omega____ theta____ kappa____ phi______ frames
    -       40.0339   57.0000  -90.0000 104

  2 omega   15.00  115.00   1.0000   30.8800
omega____ theta____ kappa____ phi______ frames
    -       40.0339   38.0000   30.0000 100

  3 omega   40.00  118.00   1.0000   30.8800
omega____ theta____ kappa____ phi______ frames
    -       40.0339  172.0000 -129.0000 78

  4 omega -121.00  -63.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  125.0000 -180.0000 58

  5 omega -146.00 -120.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -45.0000 -180.0000 26

  6 omega   40.00   66.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  119.7100 26

  7 omega   75.00  122.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  -27.1648 47

  8 omega   84.00  109.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000   44.0883 25

  9 omega   35.00   69.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  150.0000 34

 10 omega   83.00  109.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -90.0000 26

 11 omega   99.00  125.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -84.0000   51.9939 26

 12 omega   63.00  103.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  -60.0000 40

 13 omega  122.00  148.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  -60.0000 26

 14 omega  132.00  170.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000 -120.0000 38

 15 omega   18.00   44.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  -27.1648 26

 16 omega   38.00   64.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -90.0000 26

 17 omega  107.00  163.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -150.0000 56

 18 omega   80.00  106.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -80.0000   36.5977 26

 19 omega   60.00  142.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 82

 20 omega   21.00   95.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000 -180.0000 74

 21 omega   77.00  123.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  150.0000 46

 22 omega   18.00   58.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -84.0000   51.9939 40

 23 omega   74.00  100.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -150.0000 26

 24 omega   65.00  167.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  150.0000 102

 25 omega   26.00   77.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -60.0000 51

 26 omega  136.00  164.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000   30.0000 28

 27 omega   78.00  115.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   60.0000 37

 28 omega   28.00   53.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  120.0000 25

 29 omega   81.00  109.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000   30.0000 28

 30 omega   26.00   51.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  120.0000 25

 31 omega   29.00   77.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   30.0000 48

 32 omega   86.00  111.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  119.7100 25

 33 omega  119.00  167.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000  120.0000 48

 34 omega   76.00  103.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000    0.0000 27

 35 omega   16.00   61.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -120.0000 45

 36 omega   23.00   49.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -150.0000 26

 37 omega   31.00  131.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  -71.8768 100

 38 omega   61.00   86.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 25

 39 omega   18.00   62.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000   44.0883 44

 40 omega   77.00  105.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 28

 41 omega   99.00  125.00   1.0000   60.5100
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000  179.3357 26
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1287673000
_diffrn_orient_matrix_UB_12      -0.0422297000
_diffrn_orient_matrix_UB_13      -0.0621592000
_diffrn_orient_matrix_UB_21      0.1104501000
_diffrn_orient_matrix_UB_22      -0.0409865000
_diffrn_orient_matrix_UB_23      0.0959150000
_diffrn_orient_matrix_UB_31      -0.0892086000
_diffrn_orient_matrix_UB_32      0.0102370000
_diffrn_orient_matrix_UB_33      0.1278919000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20920
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         3.43
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31834
_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    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         6714
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0707
_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^)+(0.1387P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1832
_refine_ls_wR_factor_ref         0.2058
_reflns_number_gt                5346
_reflns_number_total             6714
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np8b00243_si_002.cif
_cod_data_source_block           p4-2(10-11)06
_cod_original_cell_volume        1908.03(9)
_cod_database_code               1553370
_chemical_oxdiff_formula         'C1 O1'
_reflns_odcompleteness_completeness 99.89
_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:
 C24(H24), C6(H6), C4(H4A), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C30(H30A,H30B), C31(H31A,H31B), C11(H11A,H11B), C17(H17A,
 H17B), C20(H20A,H20B), C3(H3A,H3B), C28(H28A,H28B), C2(H2A,H2B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C34(H34)
2.d Tetrahedral OH refined with riding coordinates:
 O4(H4), O2(H2), O8(H8)
2.e Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C10(H10A,H10B,H10C), C37(H37A,H37B,H37C), C25(H25A,H25B,
 H25C), C44(H44A,H44B,H44C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C14(H14A,H14B,
 H14C), C33(H33A,H33B,H33C), C36(H36A,H36B,H36C)
2.f Idealised tetrahedral OH refined as rotating group:
 O10(H10)
;
_olex2_date_sample_data_collection 2017-05-21
_olex2_submission_special_instructions 'No special instructions were received'