Zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration.
Zhu, Xin-Qi; Sun, Qing; Zhang, Zhi-Xin; Zhou, Bo; Xie, Pei-Xi; Shen, Wen-Bo; Lu, Xin; Zhou, Jin-Mei; Ye, Long-Wu; Chemical communications (Cambridge, England) 54 (2018) 7435–7438; doi:10.1039/c8cc03140a

data_7121686
_publ_section_title
;
 Zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an
 unprecedented 1,2-sulfur migration.
;
_journal_issue                   54
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7435
_journal_page_last               7438
_journal_paper_doi               10.1039/c8cc03140a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety
'0.5(C23 H26 F N O2 S), 0.5(C23 H25.55 F N O2 S)'
_chemical_formula_sum            'C23 H26 F N O2 S'
_chemical_formula_weight         399.51
_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             2017-02-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2018-01-26 deposited with the CCDC.
2018-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                91.534(4)
_cell_angle_beta                 96.604(4)
_cell_angle_gamma                90.138(4)
_cell_formula_units_Z            4
_cell_length_a                   8.7586(18)
_cell_length_b                   12.203(3)
_cell_length_c                   19.973(4)
_cell_measurement_reflns_used    4275
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.06
_cell_measurement_theta_min      2.34
_cell_volume                     2119.8(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17771
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.669
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate and hexane'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         1.357
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     589
_refine_ls_number_reflns         9239
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0960
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1191P)^2^+2.0376P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2493
_refine_ls_wR_factor_ref         0.2668
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6760
_reflns_number_total             9239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03140a2.cif
_cod_data_source_block           y1103m
_cod_depositor_comments          'Adding full bibliography for 7121686.cif.'
_cod_database_code               7121686
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C27A \\sim C27: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
3. Others
 Sof(C4A)=Sof(H4Aa)=Sof(H4Ab)=Sof(C5A)=Sof(H5Aa)=Sof(H5Ab)=1-FVAR(1)
 Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5a)=Sof(H5b)=FVAR(1)
 Sof(C6A)=Sof(H6Aa)=Sof(H6Ab)=1-FVAR(2)
 Sof(C6)=Sof(H6a)=Sof(H6b)=FVAR(2)
 Sof(C28A)=Sof(H28c)=Sof(H28d)=Sof(C29A)=Sof(H29c)=Sof(H29d)=1-FVAR(3)
 Sof(C28)=Sof(H28a)=Sof(H28b)=Sof(C29)=Sof(H29a)=Sof(H29b)=FVAR(3)
 Sof(C27A)=Sof(H27c)=Sof(H27d)=1-FVAR(4)
 Sof(C27)=Sof(H27a)=Sof(H27b)=FVAR(4)
 Sof(C30A)=Sof(H30d)=Sof(H30e)=Sof(H30f)=1-FVAR(5)
 Sof(C30)=Sof(H30a)=Sof(H30b)=Sof(H30c)=FVAR(5)
 Sof(C7)=Sof(H7a)=Sof(H7b)=Sof(H7c)=1-FVAR(6)
 Sof(C7A)=Sof(H7Aa)=Sof(H7Ab)=Sof(H7Ac)=FVAR(6)
4.a Ternary CH refined with riding coordinates:
 C31(H31), C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C32(H32a,H32b), C28(H28a,H28b), C5(H5a,H5b), C29(H29a,H29b),
 C6(H6a,H6b), C4A(H4Aa,H4Ab), C5A(H5Aa,H5Ab), C6A(H6Aa,H6Ab), C28A(H28c,H28d),
 C29A(H29c,H29d), C27(H27a,H27b), C27A(H27c,H27d)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C25(H25), C2(H2a), C19(H19), C39(H39), C35(H35), C45(H45),
 C11(H11), C15(H15), C38(H38), C12(H12), C36(H36), C23(H23), C41(H41), C20(H20),
  C14(H14), C22(H22), C21(H21), C44(H44), C43(H43), C42(H42), C4(H4)
4.d Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C30(H30a,H30b,H30c), C33(H33a,H33b,H33c), C30A(H30d,H30e,
 H30f), C7A(H7Aa,H7Ab,H7Ac), C7(H7a,H7b,H7c)
;
_olex2_submission_special_instructions 'No special instructions were received'