A tellura-Baeyer–Villiger oxidation: one-step transformation of tellurophene into chiral tellurinate lactone
Wang, Shitao; Yan, Chaoxian; Zhao, Wenlong; Liu, Xiaolan; Yuan, Cheng-Shan; Zhang, Hao-Li; Shao, Xiangfeng; Chemical Science 12 (2021) 5811–5817; doi:10.1039/D1SC00397F

data_1561180
_publ_section_title
;
 A tellura-Baeyer--Villiger oxidation: one-step transformation of
 tellurophene into chiral tellurinate lactone
;
_journal_issue                   16
_journal_name_full               'Chemical Science'
_journal_page_first              5811
_journal_page_last               5817
_journal_paper_doi               10.1039/D1SC00397F
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C84 H108 O16 Se4 Te2'
_chemical_formula_sum            'C84 H108 O16 Se4 Te2'
_chemical_formula_weight         1944.74
_chemical_name_common            2SeTe-Ox
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-08-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-10-07 deposited with the CCDC.	2021-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.815(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.8279(10)
_cell_length_b                   27.9082(16)
_cell_length_c                   32.268(3)
_cell_measurement_reflns_used    9193
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      2.45
_cell_volume                     16230(2)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            81689
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.263
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.579
_exptl_absorpt_correction_T_max  0.7856
_exptl_absorpt_correction_T_min  0.4578
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   Bruker;sadabs;2016
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       block
_exptl_crystal_F_000             7840
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         3.054
_refine_diff_density_min         -2.820
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2067
_refine_ls_number_reflns         28467
_refine_ls_number_restraints     2716
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0588
_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^)+(0.0701P)^2^+86.6145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1657
_reflns_Friedel_coverage         0.000
_reflns_number_gt                19309
_reflns_number_total             28467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00397f2.cif
_cod_data_source_block           wst
_cod_depositor_comments
'Adding full bibliography for 1561180--1561185.cif.'
_cod_database_code               1561180
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.747
_shelx_estimated_absorpt_t_min   0.640
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C156-C157 = C152-C151 = C157-C155 = C151-C154 = C153-C155 = C153-C154
 1.5 with sigma of 0.02
 C146-C148
 2.45 with sigma of 0.02
 C164-C165 = C165-C166
 1.52 with sigma of 0.02
 C178-C177
 1.52 with sigma of 0.02
 C185-C171
 4 with sigma of 0.02
 C182-C177
 1.52 with sigma of 0.02
 C178-C179 = C179-C180
 1.52 with sigma of 0.02
 C170-C169
 1.52 with sigma of 0.02
 C168-C167
 1.52 with sigma of 0.02
 C145-C119
 1.52 with sigma of 0.02
 C172-C171 = C171-C169
 1.52 with sigma of 0.02
 O1D-C170
 1.45 with sigma of 0.02
 C168-C184 = C184-C185
 1.52 with sigma of 0.02
 C183-C181 = C181-C182
 1.52 with sigma of 0.02
 C175-C173 = C173-C174
 1.52 with sigma of 0.02
 C163-C164
 1.52 with sigma of 0.02
 C176-O1D
 1.45 with sigma of 0.02
 C176-C174
 1.52 with sigma of 0.02
 C164-C166
 2.483 with sigma of 0.04
 C178-C180
 2.483 with sigma of 0.04
 C172-C169
 2.483 with sigma of 0.04
 C168-C185
 2.483 with sigma of 0.04
 C175-C174
 2.483 with sigma of 0.04
 C183-C182
 2.483 with sigma of 0.04
 C147-C146 \\sim C146-C150 \\sim C148-C147 \\sim C150-C149
 with sigma of 0.02
 O1A-C156 \\sim O1A-C152
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(C135) \\sim Ueq, Uanis(C125) \\sim Ueq, Uanis(C143) \\sim Ueq,
Uanis(C142) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C158) \\sim Ueq, Uanis(O6D) \\sim Ueq, Uanis(C159) \\sim Ueq, Uanis(C160)
\\sim Ueq, Uanis(C161) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.002
Uanis(C163) \\sim Ueq, Uanis(C164) \\sim Ueq, Uanis(C165) \\sim Ueq,
Uanis(C166) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C107) \\sim Ueq, Uanis(C137) \\sim Ueq, Uanis(C144) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
Uanis(C183) \\sim Ueq, Uanis(C181) \\sim Ueq, Uanis(C182) \\sim Ueq,
Uanis(C177) \\sim Ueq, Uanis(O6A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C148) \\sim Ueq, Uanis(C147) \\sim Ueq, Uanis(C150) \\sim Ueq,
Uanis(C149) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C180) \\sim Ueq, Uanis(C179) \\sim Ueq, Uanis(C178) \\sim Ueq,
Uanis(C177) \\sim Ueq, Uanis(O6A) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C168) \\sim Ueq, Uanis(C167) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C185) \\sim Ueq, Uanis(C184) \\sim Ueq, Uanis(C168) \\sim Ueq,
Uanis(C167) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C172) \\sim Ueq, Uanis(C171) \\sim Ueq, Uanis(C169) \\sim Ueq,
Uanis(C170) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.02
Uanis(C175) \\sim Ueq, Uanis(C173) \\sim Ueq, Uanis(C174) \\sim Ueq,
Uanis(C176) \\sim Ueq, Uanis(O1D) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C152) \\sim Ueq, Uanis(C151) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C129) \\sim Ueq, Uanis(C96) \\sim Ueq, Uanis(C119) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(C129) \\sim Ueq, Uanis(C119) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O6A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C95) \\sim Ueq, Uanis(C121) \\sim Ueq, Uanis(C139) \\sim Ueq, Uanis(C138)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C145) \\sim Ueq, Uanis(C129) \\sim Ueq, Uanis(C96) \\sim Ueq, Uanis(C119)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C172) = Uanis(C171)
Uanis(C145) = Uanis(C153) = Uanis(C119)
Uanis(C146) = Uanis(C147) = Uanis(C148)
5. Rigid body (RIGU) restrains
 C163, C164, C165, C166
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C180, C179, C178, C177, O6A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C167, C168
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C172, C171, C169, C170, O1D
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C185, C184, C168, C167
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C183, C181, C182
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O1D, C176, C174, C173, C175
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(H11A)=Sof(H11B)=Sof(H13K)=Sof(H13L)=Sof(C141)=Sof(H14C)=Sof(H14D)=
 Sof(H14M)=Sof(H14N)=Sof(C147)=Sof(H14Q)=Sof(H14R)=Sof(C148)=Sof(H14S)=
 Sof(H14T)=Sof(H14U)=Sof(C151)=Sof(H15G)=Sof(H15H)=Sof(C152)=Sof(H15I)=
 Sof(H15J)=Sof(C153)=Sof(H15K)=Sof(H15L)=Sof(H15M)=Sof(C154)=Sof(H15N)=
 Sof(H15O)=Sof(H17S)=Sof(H17T)=Sof(C181)=Sof(H18I)=Sof(H18J)=Sof(C182)=
 Sof(H18K)=Sof(H18L)=Sof(C183)=Sof(H18M)=Sof(H18N)=Sof(H18O)=1-FVAR(1)
 Sof(H11C)=Sof(H11D)=Sof(H13M)=Sof(H13N)=Sof(C140)=Sof(H14A)=Sof(H14B)=
 Sof(H14O)=Sof(H14P)=Sof(C149)=Sof(H14V)=Sof(H14W)=Sof(H14X)=Sof(C150)=
 Sof(H15A)=Sof(H15B)=Sof(C155)=Sof(H15P)=Sof(H15Q)=Sof(C156)=Sof(H15R)=
 Sof(H15S)=Sof(C157)=Sof(H15T)=Sof(H15U)=Sof(C162)=Sof(H16W)=Sof(H16X)=
 Sof(H16Y)=Sof(H17Q)=Sof(H17R)=Sof(C178)=Sof(H17U)=Sof(H17V)=Sof(C179)=
 Sof(H17W)=Sof(H17X)=Sof(C180)=Sof(H18F)=Sof(H18G)=Sof(H18H)=FVAR(1)
 Sof(C163)=Sof(H16F)=Sof(H16G)=Sof(C164)=Sof(H16H)=Sof(H16I)=Sof(C165)=
 Sof(H16J)=Sof(H16K)=Sof(C166)=Sof(H16L)=Sof(H16M)=Sof(H16N)=1-FVAR(2)
 Sof(C167)=Sof(H16O)=Sof(H16P)=Sof(C168)=Sof(H16Q)=Sof(H16R)=Sof(C184)=
 Sof(H18A)=Sof(H18B)=Sof(C185)=Sof(H18C)=Sof(H18D)=Sof(H18E)=FVAR(2)
 Sof(C173)=Sof(H17H)=Sof(H17I)=Sof(C174)=Sof(H17J)=Sof(H17K)=Sof(C175)=
 Sof(H17L)=Sof(H17M)=Sof(H17N)=Sof(C176)=Sof(H17O)=Sof(H17P)=1-FVAR(3)
 Sof(C169)=Sof(H16S)=Sof(H16T)=Sof(C170)=Sof(H17A)=Sof(H17B)=Sof(C171)=
 Sof(H17C)=Sof(H17D)=Sof(C172)=Sof(H17E)=Sof(H17F)=Sof(H17G)=FVAR(3)
7.a Riding coordinates:
 C115(H11U,H11V,H11W), C130(H13T,H13U,H13V), C142(H14E,H14F,H14G), C145(H14J,
 H14K,H14L), C160(H16A,H16B), C175(H17L,H17M,H17N), C183(H18M,H18N,H18O)
7.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16U,H16V), C25(H25A,H25B), C30(H30A,H30B), C31(H31A,
 H31B), C36(H36A,H36B), C42(H42A,H42B), C50(H50A,H50B), C51(H51A,H51B),
 C63(H63A,H63B), C68(H68A,H68B), C71(H71A,H71B), C73(H73A,H73B), C74(H74A,H74B),
  C75(H75A,H75B), C78(H78A,H78B), C82(H82A,H82B), C86(H86A,H86B), C89(H89A,
 H89B), C90(H90A,H90B), C93(H93A,H93B), C95(H95A,H95B), C96(H96A,H96B),
 C97(H97A,H97B), C98(H98A,H98B), C101(H10D,H10E), C103(H10O,H10P), C104(H10Q,
 H10R), C105(H10F,H10G), C106(H10H,H10I), C107(H10S,H10T), C108(H10J,H10K),
 C109(H10U,H10V), C110(H11C,H11D), C110(H11A,H11B), C113(H11H,H11I), C114(H11J,
 H11K), C116(H11L,H11M), C118(H11N,H11O), C119(H11P,H11Q), C120(H12G,H12H),
 C121(H12I,H12J), C122(H12K,H12L), C123(H12A,H12B), C125(H12C,H12D), C126(H12P,
 H12Q), C127(H12R,H12S), C128(H12T,H12U), C129(H12E,H12F), C132(H13F,H13G),
 C134(H13M,H13N), C134(H13K,H13L), C135(H13O,H13P), C137(H13W,H13X), C139(H13Z,
 HC), C140(H14A,H14B), C141(H14C,H14D), C143(H14H,H14I), C146(H14M,H14N),
 C146(H14O,H14P), C147(H14Q,H14R), C150(H15A,H15B), C151(H15G,H15H), C152(H15I,
 H15J), C154(H15N,H15O), C155(H15P,H15Q), C156(H15R,H15S), C157(H15T,H15U),
 C158(H15C,H15D), C159(H15E,H15F), C163(H16F,H16G), C164(H16H,H16I), C165(H16J,
 H16K), C167(H16O,H16P), C168(H16Q,H16R), C169(H16S,H16T), C170(H17A,H17B),
 C171(H17C,H17D), C173(H17H,H17I), C174(H17J,H17K), C176(H17O,H17P), C177(H17Q,
 H17R), C177(H17S,H17T), C178(H17U,H17V), C179(H17W,H17X), C181(H18I,H18J),
 C182(H18K,H18L), C184(H18A,H18B)
7.c Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C56(H56A,H56B,H56C), C99(H99A,H99B,H99C), C100(H10A,H10B,
 H10C), C102(H10L,H10M,H10N), C111(H11R,H11S,H11T), C112(H11E,H11F,H11G),
 C117(H11X,H11Y,H), C124(H12M,H12N,H12O), C131(H13C,H13D,H13E), C133(H13H,H13I,
 H13J), C136(H13Q,H13R,H13S), C138(H13Y,HA,HB), C144(H14Y,HD,HE), C148(H14S,
 H14T,H14U), C149(H14V,H14W,H14X), C153(H15K,H15L,H15M), C161(H16C,H16D,H16E),
 C162(H16W,H16X,H16Y), C166(H16L,H16M,H16N), C172(H17E,H17F,H17G), C180(H18F,
 H18G,H18H), C185(H18C,H18D,H18E)
;
_shelx_res_checksum              92688
_olex2_submission_special_instructions 'No special instructions were received'