Total synthesis of (±)-sculponeatin N.
Pan, Zhiqiang; Zheng, Cunying; Wang, Hongyu; Chen, Yanhe; Li, Yun; Cheng, Bin; Zhai, Hongbin; Organic letters 16 (2014) 216–219; doi:10.1021/ol403208g

data_1513562
_publ_section_title
;
 Total synthesis of (+-)-sculponeatin N.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              216
_journal_page_last               219
_journal_paper_doi               10.1021/ol403208g
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C12 H18 O4'
_chemical_formula_sum            'C12 H18 O4'
_chemical_formula_weight         226.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4715)
;
_cell_angle_alpha                72.646(7)
_cell_angle_beta                 84.919(7)
_cell_angle_gamma                72.923(7)
_cell_formula_units_Z            6
_cell_length_a                   9.5712(8)
_cell_length_b                   11.3652(9)
_cell_length_c                   18.3894(13)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    294.5(6)
_cell_measurement_theta_max      72.7000
_cell_measurement_theta_min      4.2470
_cell_volume                     1825.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      294.5(6)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9805
_diffrn_measured_fraction_theta_max 0.9612
_diffrn_measurement_details
;
  1 omega   22.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 38

  2 omega  -77.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   90.0000 40

  3 omega  -22.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 34

  4 omega  -66.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000   57.0000 -180.0000 49

  5 omega -108.00  -73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000  -90.0000 35

  6 omega  -96.00  -70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -135.0000  157.0000 26

  7 omega -128.00 -103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -135.0000  157.0000 25

  8 omega    1.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000  -99.0000  -30.0000 96

  9 omega   47.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   38.0000  150.0000 83

 10 omega  -49.00    7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   50.0000   30.0000 56

 11 omega   55.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -180.0000 37

 12 omega   42.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   30.0000 69

 13 omega  102.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   14.0000   84.8474 36

 14 omega  116.00  142.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  -90.0000 26

 15 omega   71.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000  -30.0000 26

 16 omega   81.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000 -180.0000 68

 17 omega   42.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  -30.0000 40

 18 omega   92.00  141.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000  -60.0000 49

 19 omega   81.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -120.0000 33

 20 omega   46.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000  -60.0000 26

 21 omega   82.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   90.0000 25

 22 omega   54.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000 -150.0000 29

 23 omega  111.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -120.0000 41

 24 omega   46.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   90.0000 45

 25 omega  100.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000  -30.0000 49

 26 omega   44.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   14.0000   84.8474 42

 27 omega   41.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000   90.0000 51

 28 omega  111.00  136.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000 -120.0000 25

 29 omega  110.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000  150.0000 25

 30 omega   58.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  -30.0000 38

 31 omega   83.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -150.0000 38

 32 omega  -74.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000    0.0000 27

 33 omega   -1.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   60.0000 27

 34 omega  -82.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 48

 35 omega   36.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   60.0000 33

 36 omega  -60.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 26

 37 omega  -92.00  -27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -38.0000  150.0000 65

 38 omega -100.00  -74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000  -60.0000 26

 39 omega   28.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   90.0000 63

 40 omega   34.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000  -99.0000 -180.0000 66

 41 omega   68.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000 -125.0000   90.0000 26

 42 omega   28.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000 -125.0000   90.0000 28

 43 omega  -49.00    9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   38.0000  -60.0000 58

 44 omega   48.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -28.0000  -28.0000 42

 45 omega   44.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000  120.0000 52

 46 omega  105.00  156.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -93.0000 -134.0778 51

 47 omega   43.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  -60.0000 73

 48 omega   79.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -150.0000 36

 49 omega   66.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -93.0000 -134.0778 26

 50 omega  153.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   16.0000  -83.9355 25

 51 omega   44.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000   30.0000 50

 52 omega  125.00  151.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000  120.0000 26

 53 omega   96.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -84.0000 -172.6270 39

 54 omega  153.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -12.0000    0.0000 25

 55 omega   56.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  -60.0000 26

 56 omega   66.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000    0.0000 26

 57 omega   85.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  120.0000 25

 58 omega  114.00  140.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000  -60.0000 26

 59 omega  109.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -150.0000 43

 60 omega   91.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000   90.0000 26

 61 omega   51.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000    0.0000 26

 62 omega   80.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000  120.0000 30

 63 omega   47.00   73.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000   30.0000 26

 64 omega   52.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -84.0000 -172.6270 31

 65 omega   65.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -30.0000  116.6987 26

 66 omega  115.00  163.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000  120.0000 48

 67 omega   86.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000    0.0000 25

 68 omega  150.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   25.0000  -30.0000 26

 69 omega   43.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000    0.0000 25

 70 omega   92.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  -60.0000 26

 71 omega   96.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000   30.0000 41

 72 omega   79.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   25.0000  -30.0000 46

 73 omega   86.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -99.0000  -66.2205 25

 74 omega  110.00  136.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000    0.0000 26

 75 omega   44.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  -30.0000 43
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0056462000
_diffrn_orient_matrix_UB_12      -0.0196397000
_diffrn_orient_matrix_UB_13      0.0863572000
_diffrn_orient_matrix_UB_21      -0.0378672000
_diffrn_orient_matrix_UB_22      -0.1279430000
_diffrn_orient_matrix_UB_23      0.0154640000
_diffrn_orient_matrix_UB_31      0.1639793000
_diffrn_orient_matrix_UB_32      -0.0718738000
_diffrn_orient_matrix_UB_33      0.0006680000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19719
_diffrn_reflns_theta_full        71.00
_diffrn_reflns_theta_max         72.12
_diffrn_reflns_theta_min         4.25
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.103(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.427
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         7123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.427
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0772
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2633
_refine_ls_wR_factor_ref         0.3268
_reflns_number_gt                6060
_reflns_number_total             7123
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403208g_si_003.cif
_cod_data_source_block           zhcy0221
_cod_original_cell_volume        1825.1(2)
_cod_database_code               1513562
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 98.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.88
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C14(H14), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B), C28(H28A,H28B), C29(H29A,H29B),
 C30(H30A,H30B), C33(H33A,H33B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C), C37(H37A,H37B,H37C)
;