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_1513563
_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         'C20 H28 O4'
_chemical_formula_sum            'C20 H28 O4'
_chemical_formula_weight         332.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-01
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.080(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.2790(11)
_cell_length_b                   6.5834(3)
_cell_length_c                   15.0980(7)
_cell_measurement_reflns_used    2314
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0720
_cell_measurement_theta_min      3.6950
_cell_volume                     1806.64(16)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_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      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.9029
_diffrn_measurement_details
;
  1 omega  -63.00   -6.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -57.0000  150.0000 57

  2 omega   48.00   95.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000  120.0000 47

  3 omega   44.00   94.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000 -150.0000 50

  4 omega  -12.00   99.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   19.0000  -90.0000 111
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0090350000
_diffrn_orient_matrix_UB_12      -0.0929236000
_diffrn_orient_matrix_UB_13      -0.0199859000
_diffrn_orient_matrix_UB_21      0.0377710000
_diffrn_orient_matrix_UB_22      0.0173912000
_diffrn_orient_matrix_UB_23      0.0137460000
_diffrn_orient_matrix_UB_31      -0.0035181000
_diffrn_orient_matrix_UB_32      -0.0517068000
_diffrn_orient_matrix_UB_33      0.0405779000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7775
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79840
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0630
_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^)+(0.0493P)^2^+1.1474P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1730
_reflns_number_gt                2522
_reflns_number_total             3688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403208g_si_002.cif
_cod_data_source_block           panzhq0227
_cod_original_cell_volume        1806.64(17)
_cod_database_code               1513563
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H1A,H1B} of C1, H5 of C5, {H3A,H3B} of C3, {H2A,H2B} of C2, {H12A,H12B} of
  C12, {H11A,H11B} of C11, H9 of C9, {H6A,H6B} of C6, {H20A,H20B} of C20, H13
  of C13, {H14A,H14B} of C14
 At 1.5 times of:
  H3 of O3, {H19A,H19B,H19C} of C19, {H18A,H18B,H18C} of C18
2.a Ternary CH refined with riding coordinates:
 C5(H5), C9(H9), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C11(H11A,H11B), C12(H12A,
 H12B), C14(H14A,H14B), C20(H20A,H20B)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;