Enantioselective total synthesis of (-)-walsucochin B.
Xu, Shiyan; Gu, Jixiang; Li, Huilin; Ma, Donghui; Xie, Xingang; She, Xuegong; Organic letters 16 (2014) 1996–1999; doi:10.1021/ol500553x

data_1514195
_publ_section_title
;
 Enantioselective total synthesis of (-)-walsucochin B.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1996
_journal_page_last               1999
_journal_paper_doi               10.1021/ol500553x
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C33 H41 Br O5'
_chemical_formula_sum            'C33 H41 Br O5'
_chemical_formula_weight         597.57
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-11-05
_audit_creation_method
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Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.881(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3108(4)
_cell_length_b                   21.7962(11)
_cell_length_c                   13.5496(5)
_cell_measurement_reflns_used    2819
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3710
_cell_measurement_theta_min      3.5470
_cell_volume                     3023.2(2)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
SHELX, 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 0.9976
_diffrn_measured_fraction_theta_max 0.8895
_diffrn_measurement_details
;
  1 omega  -92.00  -65.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  178.0000  -30.0000 18

  2 omega  -14.00   25.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -99.0000   90.0000 26

  3 omega    5.00   59.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -99.0000  -60.0000 36

  4 omega  -31.00   87.50   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512    0.0000  -30.0000 79
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0228300000
_diffrn_orient_matrix_UB_12      0.0278645000
_diffrn_orient_matrix_UB_13      -0.0187246000
_diffrn_orient_matrix_UB_21      -0.0002539000
_diffrn_orient_matrix_UB_22      0.0137242000
_diffrn_orient_matrix_UB_23      0.0474366000
_diffrn_orient_matrix_UB_31      0.0654206000
_diffrn_orient_matrix_UB_32      -0.0096968000
_diffrn_orient_matrix_UB_33      0.0134232000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11607
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.004
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.398
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.3100
_exptl_crystal_size_mid          0.2700
_exptl_crystal_size_min          0.2400
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+1.1663P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1523
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3481
_reflns_number_total             5940
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol500553x_si_001.cif
_cod_data_source_block           xushy0904
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-8800/cifs/1514195.cif.
;
_cod_original_cell_volume        3023.1(2)
_cod_database_code               1514195
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.76
_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.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C29(H29), C30(H30), C32(H32), C33(H33)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,
 H26B,H26C)
;
_shelx_res_checksum              72921
_shelx_hkl_checksum              93376