Stereoselective Radical Cyclization Cascades Triggered by Addition of Diverse Radicals to Alkynes To Construct 6(5)-6-5 Fused Rings.
Huang, Lin; Ye, Liu; Li, Xiao-Hua; Li, Zhong-Liang; Lin, Jin-Shun; Liu, Xin-Yuan; Organic letters 18 (2016) 5284–5287; doi:10.1021/acs.orglett.6b02599

data_1555824
_publ_section_title
;
 Stereoselective Radical Cyclization Cascades Triggered by Addition of
 Diverse Radicals to Alkynes To Construct 6(5)-6-5 Fused Rings.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5284
_journal_page_last               5287
_journal_paper_doi               10.1021/acs.orglett.6b02599
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C27 H28 O9 S'
_chemical_formula_sum            'C27 H28 O9 S'
_chemical_formula_weight         528.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                101.2240(10)
_cell_angle_beta                 93.1880(10)
_cell_angle_gamma                112.0500(10)
_cell_formula_units_Z            4
_cell_length_a                   9.7672(4)
_cell_length_b                   11.7742(4)
_cell_length_c                   24.7073(9)
_cell_measurement_reflns_used    9409
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.53
_cell_measurement_theta_min      3.68
_cell_volume                     2557.16(17)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            47166
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.632
_diffrn_reflns_theta_max         67.632
_diffrn_reflns_theta_min         1.841
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.588
_exptl_absorpt_correction_T_max  0.5207
_exptl_absorpt_correction_T_min  0.4149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0776 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.7968.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     675
_refine_ls_number_reflns         9050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0326P)^2^+1.9183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8920
_reflns_number_total             9050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02599_si_004.cif
_cod_data_source_block           cxy419_0m
_cod_database_code               1555824
_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:
 C13(H13), C8(H8), C39(H39), C41(H41)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C6(H6A,H6B), C7(H7A,H7B), C29(H29A,H29B), C38(H38A,H38B),
 C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C16(H16), C19(H19), C23(H23), C17(H17), C20(H20), C15(H15),
 C14(H14), C46(H46), C50(H50), C54(H54), C45(H45), C48(H48), C53(H53), C51(H51),
  C47(H47)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C3(H3A,H3B,H3C), C24(H24A,H24B,H24C), C1(H1A,H1B,H1C),
 C32(H32A,H32B,H32C), C55(H55A,H55B,H55C), C36(H36A,H36B,H36C), C28(H28A,H28B,
 H28C)
;
_shelx_res_checksum              12734
_shelx_hkl_checksum              95852
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'