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_1513564
_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         '0.5(C20 H27 O4), 0.5(C20 H28 O4)'
_chemical_formula_sum            'C20 H27.5 O4'
_chemical_formula_weight         331.92
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-11-22
_audit_creation_method
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Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4715)
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_cell_angle_alpha                90
_cell_angle_beta                 94.376(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.0862(4)
_cell_length_b                   24.1874(17)
_cell_length_c                   20.3324(13)
_cell_measurement_reflns_used    2234
_cell_measurement_temperature    294.7(3)
_cell_measurement_theta_max      28.5642
_cell_measurement_theta_min      2.9975
_cell_volume                     3474.7(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      294.7(3)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_details
;
  1 omega  -42.00   38.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492   38.0000  -90.0000 80

  2 omega  -77.00  -51.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  127.0000  151.0000 26

  3 omega  -35.00   50.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -77.0000  -60.0000 85

  4 omega  -42.00   50.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -38.0000  150.0000 92
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0071172000
_diffrn_orient_matrix_UB_12      -0.0116364000
_diffrn_orient_matrix_UB_13      0.0321203000
_diffrn_orient_matrix_UB_21      -0.0098744000
_diffrn_orient_matrix_UB_22      -0.0268519000
_diffrn_orient_matrix_UB_23      -0.0138456000
_diffrn_orient_matrix_UB_31      0.0996460000
_diffrn_orient_matrix_UB_32      -0.0018205000
_diffrn_orient_matrix_UB_33      -0.0009887000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0825
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17314
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.627
_diffrn_reflns_theta_min         3.004
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             1436
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         7856
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.0899
_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^)+(0.1331P)^2^+1.1331P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2304
_refine_ls_wR_factor_ref         0.2895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4105
_reflns_number_total             7856
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol403208g_si_005.cif
_cod_data_source_block           panzhq0115_2
_cod_original_cell_volume        3474.8(4)
_cod_original_formula_sum        'C20 H27.50 O4'
_cod_database_code               1513564
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Restrained distances
 H18A-C18
 0.94 with sigma of 0.02
 H18B-C18
 0.94 with sigma of 0.02
 O4-H4
 0.82 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C4(H4A), C6(H6), C24(H24), C26(H26), C33(H33)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C11(H11A,H11B), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B),
  C31(H31A,H31B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C40(H40A,H40B)
3.c X=CH2 refined with riding coordinates:
 C9(H9A,H9B), C29(H29A,H29B)
3.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C38(H38A,H38B,H38C), C39(H39A,H39B,
 H39C)
3.e Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_shelx_res_checksum              47062
_shelx_hkl_checksum              93162