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_1513565
_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         'C23 H36 O4 Si'
_chemical_formula_sum            'C23 H36 O4 Si'
_chemical_formula_weight         404.61
_chemical_name_systematic
;
 ? 
;
_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                70.766(8)
_cell_angle_beta                 75.194(8)
_cell_angle_gamma                77.187(8)
_cell_formula_units_Z            2
_cell_length_a                   8.4671(7)
_cell_length_b                   11.9089(11)
_cell_length_c                   12.8735(11)
_cell_measurement_reflns_used    1519
_cell_measurement_temperature    295.08(10)
_cell_measurement_theta_max      28.6079
_cell_measurement_theta_min      3.3051
_cell_volume                     1171.40(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
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      295.08(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9833
_diffrn_measurement_details
;
  1 omega  -93.00  -50.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -38.0000   60.0000 43

  2 omega   29.00   63.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000 -120.0000 34

  3 omega   36.00   71.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000   30.0000 35

  4 omega   -9.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  120.0000 104

  5 omega    5.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000 -120.0000 91

  6 omega   -6.00   76.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000    0.0000 82
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0271572000
_diffrn_orient_matrix_UB_12      -0.0587392000
_diffrn_orient_matrix_UB_13      -0.0059627000
_diffrn_orient_matrix_UB_21      0.0532109000
_diffrn_orient_matrix_UB_22      -0.0121216000
_diffrn_orient_matrix_UB_23      0.0381881000
_diffrn_orient_matrix_UB_31      -0.0641367000
_diffrn_orient_matrix_UB_32      -0.0217850000
_diffrn_orient_matrix_UB_33      0.0452846000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8420
_diffrn_reflns_theta_full        28.67
_diffrn_reflns_theta_max         28.67
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5273
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0761
_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          0.2335
_refine_ls_wR_factor_ref         0.3166
_reflns_number_gt                2917
_reflns_number_total             5273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403208g_si_004.cif
_cod_data_source_block           panzhq0115_1
_cod_original_cell_volume        1171.39(18)
_cod_database_code               1513565
_reflns_odcompleteness_completeness 99.69
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C19(H19)
3.d X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
3.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C)
;