Biomimetic syntheses of C23 terpenoids: structural revision of salyunnanin A and confirmation of hassanane
Zhang, Xun; Li, Zhongle; Yong, Huaya; Xie, Zhixiang; Organic Chemistry Frontiers 5 (2018) 3469–; doi:10.1039/C8QO00772A

data_1554407
_publ_section_title
;
 Biomimetic syntheses of C23 terpenoids: structural revision of
 salyunnanin A and confirmation of hassanane
;
_journal_issue                   23
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3469
_journal_paper_doi               10.1039/C8QO00772A
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H28 O6'
_chemical_formula_sum            'C23 H28 O6'
_chemical_formula_weight         400.45
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-18 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.259(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3005(4)
_cell_length_b                   12.1224(5)
_cell_length_c                   11.9121(6)
_cell_measurement_reflns_used    4540
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.7460
_cell_measurement_theta_min      3.6560
_cell_volume                     1017.05(9)
_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 16.0733
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
  1 omega  -85.00  -52.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -120.0000 22

  2 omega  -24.00    9.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -50.0000  150.0000 22

  3 omega  -78.00  -31.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -50.0000  150.0000 31

  4 omega   40.00   91.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  -30.0000 34

  5 omega   30.00   73.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   90.0000 29

  6 omega    1.00   35.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  -30.0000 23

  7 omega  -10.00   17.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   90.0000 18

  8 omega   37.00   64.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 18

  9 omega   36.00   61.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 17

 10 omega   51.00   88.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 25

 11 omega  128.00  170.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 28

 12 omega   38.00   68.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 20

 13 omega   84.00  169.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 57

 14 omega   44.00  101.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 38

 15 omega   38.00   90.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 35

 16 omega   73.00   98.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 17

 17 omega   36.00  159.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -60.0000 82

 18 omega   -9.00   18.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 18

 19 omega  -58.00  -16.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000    0.0000 28

 20 omega  -62.00   -2.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  125.0000  120.0000 40

 21 omega   43.00   74.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 21

 22 omega   83.00  110.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 18

 23 omega   83.00  125.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -150.0000 28

 24 omega   31.00   61.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -150.0000 20

 25 omega   90.00  132.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -180.0000 28

 26 omega   77.00  104.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 18

 27 omega  151.00  178.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   22.0000  -32.8954 18

 28 omega   86.00  113.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -120.0000 18

 29 omega   57.00  114.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 38

 30 omega   88.00  115.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 18

 31 omega   68.00   95.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  -90.0000 18

 32 omega   61.00   92.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 21

 33 omega   76.00  101.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 17

 34 omega   70.00  100.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -120.0000 20

 35 omega   34.00   85.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 34

 36 omega   81.00  108.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -90.0000 18

 37 omega   44.00   96.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 35

 38 omega  110.00  135.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 17

 39 omega   88.00  113.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 17

 40 omega   81.00  108.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -60.0000 18

 41 omega   70.00   97.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  -60.0000 18

 42 omega  102.00  129.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 18

 43 omega   64.00  101.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 25

 44 omega   97.00  122.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   22.0000  -32.8954 17

 45 omega   92.00  119.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -120.0000 18

 46 omega   68.00   95.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   22.0000  -32.8954 18
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1394083000
_diffrn_orient_matrix_UB_12      0.0302356000
_diffrn_orient_matrix_UB_13      0.1172672000
_diffrn_orient_matrix_UB_21      -0.1424610000
_diffrn_orient_matrix_UB_22      0.0857823000
_diffrn_orient_matrix_UB_23      0.0219257000
_diffrn_orient_matrix_UB_31      -0.0900556000
_diffrn_orient_matrix_UB_32      -0.0887004000
_diffrn_orient_matrix_UB_33      0.0612176000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6953
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         6.45
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69066
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0950P)^2^+0.0817P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1395
_reflns_number_gt                3291
_reflns_number_total             3388
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo00772a2.cif
_cod_data_source_block           zhangxun_0718
_cod_original_cell_volume        1017.06(9)
_cod_database_code               1554407
_reflns_odcompleteness_completeness 96.77
_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:
 C1(H1), C9(H9), C10(H10), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C23(H23A,H23B,H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_olex2_date_sample_data_collection 2018-07-18
_olex2_submission_special_instructions 'No special instructions were received'