Synthesis of Tricyclo[4,3,1,0(1,5)]decane Core of Plumisclerin A Using Pauson-Khand Annulation and SmI2-Mediated Radical Cyclization.
Chen, Ji-Peng; He, Wei; Yang, Zhen-Yu; Yao, Zhu-Jun; Organic letters 17 (2015) 3379–3381; doi:10.1021/acs.orglett.5b01563

data_1520694
_publ_section_title
;
 Synthesis of Tricyclo[4,3,1,0(1,5)]decane Core of Plumisclerin A Using
 Pauson-Khand Annulation and SmI2-Mediated Radical Cyclization.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3379
_journal_page_last               3381
_journal_paper_doi               10.1021/acs.orglett.5b01563
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C33 H27 N3 O13'
_chemical_formula_sum            'C33 H27 N3 O13'
_chemical_formula_weight         673.57
_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     direct
_audit_creation_date             2015-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                86.284(4)
_cell_angle_beta                 86.306(4)
_cell_angle_gamma                68.207(3)
_cell_formula_units_Z            2
_cell_length_a                   11.319(3)
_cell_length_b                   12.665(3)
_cell_length_c                   14.597(3)
_cell_measurement_reflns_used    5517
_cell_measurement_temperature    133
_cell_measurement_theta_max      27.540
_cell_measurement_theta_min      2.410
_cell_volume                     1937.1(8)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      133
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11856
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_min         1.939
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0889 before and 0.0539 after correction.
The Ratio of minimum to maximum transmission is 0.6758.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_description       block
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.009(3)
_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   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         6820
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0739
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1480P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2084
_refine_ls_wR_factor_ref         0.2246
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4773
_reflns_number_total             6820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01563_si_002.cif
_cod_data_source_block           mo_dm12136_0m
_cod_depositor_comments          'Adding full bibliography for 1520694.cif.'
_cod_database_code               1520694
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.966
_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
N1 \\sim O8 \\sim O9 \\sim N1' \\sim O8' \\sim O9': within 1.7A with sigma of
0.01 and sigma for terminal atoms of 0.02
N2 \\sim O11: within 1.7A with sigma of 0.001 and sigma for terminal atoms of
0.002
3. Others
 Fixed Sof: N1(0.5) O8(0.5) O9(0.5) N1'(0.5) O8'(0.5) O9'(0.5)
4.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C9(H9), C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C12(H12A,H12B)
4.c Me refined with riding coordinates:
 C10(H10A,H10B,H10C)
4.d Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25),
 C26(H26), C29(H29), C30(H30), C32(H32), C33(H33)
;
_shelx_res_checksum              31602
_shelx_hkl_checksum              34518
_olex2_submission_special_instructions 'No special instructions were received'