Total synthesis of (±)-sacidumlignans D and A through Ueno-Stork radical cyclization reaction.
Zhang, Jian-Jian; Yan, Chang-Song; Peng, Yu; Luo, Zhen-Biao; Xu, Xiao-Bo; Wang, Ya-Wen; Organic & biomolecular chemistry 11 (2013) 2498–2513; doi:10.1039/c3ob00053b

data_7152843
_publ_section_title
;
 Total synthesis of (+-)-sacidumlignans D and A through Ueno-Stork radical
 cyclization reaction.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2498
_journal_page_last               2513
_journal_paper_doi               10.1039/c3ob00053b
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C22 H24 O6'
_chemical_formula_sum            'C22 H24 O6'
_chemical_formula_weight         384.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.571(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3947(7)
_cell_length_b                   8.5143(4)
_cell_length_c                   21.6771(10)
_cell_measurement_reflns_used    1269
_cell_measurement_temperature    294.50(14)
_cell_measurement_theta_max      28.4643
_cell_measurement_theta_min      2.9471
_cell_volume                     2214.1(2)
_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
;
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    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      294.50(14)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.9753
_diffrn_measurement_details
;
1 omega -58.00 -31.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -19.3492 118.0000 88.0000 27
2 omega 54.00 91.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 57.0000 -150.0000 37
3 omega 4.00 96.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 38.0000 120.0000 92
4 omega 0.00 33.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -57.0000 -120.0000 33
5 omega -8.00 18.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -77.0000 120.0000 26
6 omega -8.00 89.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 77.0000 -30.0000 97
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0310823000
_diffrn_orient_matrix_UB_12      0.0016093000
_diffrn_orient_matrix_UB_13      0.0233401000
_diffrn_orient_matrix_UB_21      -0.0491103000
_diffrn_orient_matrix_UB_22      0.0168575000
_diffrn_orient_matrix_UB_23      -0.0240597000
_diffrn_orient_matrix_UB_31      -0.0107803000
_diffrn_orient_matrix_UB_32      -0.0815835000
_diffrn_orient_matrix_UB_33      -0.0044776000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.1028
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10782
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.95
_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  0.59743
_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 orange'
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_platon_squeeze_details
;
;
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.007(4)
_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   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4210
_refine_ls_number_restraints     168
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1775
_refine_ls_R_factor_gt           0.0973
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1668P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2672
_refine_ls_wR_factor_ref         0.3319
_reflns_number_gt                1810
_reflns_number_total             4210
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob00053b.txt
_cod_data_source_block           zhangjj1026
_cod_database_code               7152843
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32