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_1561182
_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         'C98 H124 Cl2 O17 Te2'
_chemical_formula_sum            'C98 H124 Cl2 O17 Te2'
_chemical_formula_weight         1900.06
_chemical_name_common            IM-1
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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                 105.560(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   37.942(2)
_cell_length_b                   17.3698(11)
_cell_length_c                   29.2185(18)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.60
_cell_volume                     18550.6(19)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0431
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            92164
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.028
_diffrn_reflns_theta_max         25.028
_diffrn_reflns_theta_min         2.011
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0678
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0986 before and 0.0434 after correction.
The Ratio of minimum to maximum transmission is 0.7275.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             7888
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.327
_refine_diff_density_min         -2.036
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1243
_refine_ls_number_reflns         16335
_refine_ls_number_restraints     1372
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0876
_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^)+(0.1140P)^2^+137.3597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2282
_refine_ls_wR_factor_ref         0.2711
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9982
_reflns_number_total             16335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00397f2.cif
_cod_data_source_block           mo_0612_0m
_cod_depositor_comments
'Adding full bibliography for 1561180--1561185.cif.'
_cod_original_cell_volume        18550.3(19)
_cod_database_code               1561182
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.915
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, 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
 C41A-C40A = C39A-C38A
 1.54 with sigma of 0.02
 C33B-C32B = C37B-C36B
 1.56 with sigma of 0.02
 C61B-C65B
 1.47 with sigma of 0.02
 C60B-C65B
 2.411 with sigma of 0.02
 C35B-C37B
 2.5 with sigma of 0.02
 C64B-C65B
 1.5 with sigma of 0.02
 C33A-C35A
 2.5 with sigma of 0.02
 C63B-C65B
 2.476 with sigma of 0.02
 C62B-C61B
 1.5 with sigma of 0.02
 C49B-C48B
 1.58 with sigma of 0.02
 C49B-C47B
 2.5 with sigma of 0.02
 C41A-C37A = C38A-C37A
 1.56 with sigma of 0.02
 C30B-C8 = C34B-C35B
 1.56 with sigma of 0.02
 C36B-C35B
 1.5 with sigma of 0.02
 C48B-C46B
 2.5 with sigma of 0.02
 C34A-C33A
 1.56 with sigma of 0.02
 C34A-C32A
 2.5 with sigma of 0.02
 O2B-C34B = O2B-C30B
 1.45 with sigma of 0.02
 C6-C76 = C22-C76
 1.56 with sigma of 0.02
 C74-C22
 2.5 with sigma of 0.02
 C74-C6
 2.5 with sigma of 0.02
 C36A-C41A
 2.5 with sigma of 0.02
 C59B-O2A
 1.47 with sigma of 0.02
 C63B-C64B
 1.47 with sigma of 0.02
 C60B-C61B
 1.47 with sigma of 0.02
 C60B-C59B
 1.5 with sigma of 0.02
 C28B-C26B
 2.476 with sigma of 0.02
 C59B-C61B
 2.476 with sigma of 0.02
 C61B-C62B
 1.52 with sigma of 0.02
 C50B-C48B
 1.52 with sigma of 0.02
 C36A-O3A
 1.47 with sigma of 0.02
 C62B-C60B
 2.52 with sigma of 0.04
 C60B-C62B
 2.52 with sigma of 0.04
 C59B-C64B
 2.52 with sigma of 0.04
 C22-C76 \\sim C6-C76
 with sigma of 0.02
 C41A-C37A \\sim C38A-C37A
 with sigma of 0.02
 C41A-C40A \\sim C39A-C38A
 with sigma of 0.02
 O2B-C34B \\sim O2B-C30B
 with sigma of 0.02
 C56B-C55B \\sim C57B-C56B \\sim C58B-C57B
 with sigma of 0.02
 C32B-C8 \\sim C36B-C35B
 with sigma of 0.02
3. Rigid bond restraints
 C34A, C35A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C28B, C29B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C37A, C38A
 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(C32A) \\sim Ueq, Uanis(C34A) \\sim Ueq, Uanis(C35A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C59B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C62B) \\sim Ueq, Uanis(C61B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C59B, C65B, C60B, C61B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C63B, C64B, C65B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C59B, C60B, C61B, C62B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C48B, C49B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl1A, C6A'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C6A'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl1, O1B', C1B', C2B', C3B', C4B', C5B', C6B', C7B'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O7A, Cl1A, O1A', C1A', C2A', C3A', C4A', C5A', C6A', C8A'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C48B, C50B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O2A, C63B, C64B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C59B, C60B, C61B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(H59A)=Sof(H59B)=Sof(H48A)=Sof(H48B)=Sof(C63B)=Sof(H63A)=Sof(H63B)=
 Sof(C64B)=Sof(H64A)=Sof(H64B)=Sof(C65B)=Sof(H65A)=Sof(H65B)=Sof(H65C)=
 Sof(C50B)=Sof(H50A)=Sof(H50B)=Sof(H50C)=Sof(Cl1)=Sof(O1B')=Sof(C1B')=Sof(C2B')=
 Sof(C3B')=Sof(H3B')=Sof(C4B')=Sof(H4B')=Sof(C5B')=Sof(H5B')=Sof(C6B')=
 Sof(C7B')=Sof(H7B')=1-FVAR(1)
 Sof(H59C)=Sof(H59D)=Sof(H48C)=Sof(H48D)=Sof(Cl1A)=Sof(O1A')=Sof(C1A')=
 Sof(C2A')=Sof(C3A')=Sof(H3A')=Sof(C4A')=Sof(H4A')=Sof(C5A')=Sof(H5A')=
 Sof(C6A')=Sof(C8A')=Sof(H8A')=Sof(C60B)=Sof(H60A)=Sof(H60B)=Sof(C61B)=
 Sof(H61A)=Sof(H61B)=Sof(C62B)=Sof(H62A)=Sof(H62B)=Sof(H62C)=Sof(C49B)=
 Sof(H49A)=Sof(H49B)=Sof(H49C)=FVAR(1)
 Fixed Sof: H37A(0.5) H37B(0.5) H37C(0.5) H37D(0.5) H76A(0.5) H76B(0.5)
 H76C(0.5) H76D(0.5) C34B(0.5) H34C(0.5) H34D(0.5) C35B(0.5) H35D(0.5)
 H35E(0.5) C36B(0.5) H36C(0.5) H36D(0.5) C37B(0.5) H37E(0.5) H37F(0.5)
 H37G(0.5) C41A(0.5) H41D(0.5) H41E(0.5) C40A(0.5) H40C(0.5) H40D(0.5)
 H40E(0.5) C6(0.5) H6A(0.5) H6B(0.5) H6C(0.5) C30B(0.5) H30A(0.5) H30B(0.5)
 C8(0.5) H8A(0.5) H8B(0.5) C32B(0.5) H32C(0.5) H32D(0.5) C33B(0.5) H33C(0.5)
 H33D(0.5) H33E(0.5) C38A(0.5) H38C(0.5) H38D(0.5) C39A(0.5) H39C(0.5)
 H39D(0.5) H39E(0.5) C22(0.5) H22A(0.5) H22B(0.5) H22C(0.5)
7.a Riding coordinates:
 C65B(H65A,H65B,H65C), C37B(H37E,H37F,H37G), C33B(H33C,H33D,H33E)
7.b Secondary CH2 refined with riding coordinates:
 C27B(H27A,H27B), C28B(H28A,H28B), C55B(H55A,H55B), C56B(H56A,H56B), C57B(H57A,
 H57B), C51B(H51A,H51B), C52B(H52A,H52B), C47B(H47A,H47B), C32A(H32A,H32B),
 C33A(H33A,H33B), C38B(H38A,H38B), C39B(H39A,H39B), C36A(H36A,H36B), C37A(H37A,
 H37B), C37A(H37C,H37D), C70(H70A,H70B), C71(H71A,H71B), C72(H72A,H72B),
 C74(H74A,H74B), C75(H75A,H75B), C76(H76A,H76B), C76(H76C,H76D), C42B(H42A,
 H42B), C43B(H43A,H43B), C44B(H44A,H44B), C26B(H26A,H26B), C59B(H59A,H59B),
 C59B(H59C,H59D), C53B(H53A,H53B), C46B(H46A,H46B), C48B(H48C,H48D), C48B(H48A,
 H48B), C34A(H34A,H34B), C40B(H40A,H40B), C63B(H63A,H63B), C64B(H64A,H64B),
 C34B(H34C,H34D), C35B(H35D,H35E), C36B(H36C,H36D), C41A(H41D,H41E), C60B(H60A,
 H60B), C61B(H61A,H61B), C30B(H30A,H30B), C8(H8A,H8B), C32B(H32C,H32D),
 C38A(H38C,H38D)
7.c Aromatic/amide H refined with riding coordinates:
 C15A(H15A), C18A(H18A), C7A(H7A), C14A(H14A), C15B(H15B), C18B(H18B),
 C7B(H7B), C25B(H25B), C24B(H24B), C23B(H23B), C21B(H21B), C14B(H14B),
 C3A'(H3A'), C4A'(H4A'), C5A'(H5A'), C8A'(H8A'), C3B'(H3B'), C4B'(H4B'),
 C5B'(H5B'), C7B'(H7B')
7.d Fitted hexagon refined as free rotating group:
 C2A'(C3A',C4A',C5A',C6A',C8A'), C2B'(C3B',C4B',C5B',C6B',C7B')
7.e Idealised Me refined as rotating group:
 C41B(H41A,H41B,H41C), C73(H73A,H73B,H73C), C45B(H45A,H45B,H45C), C29B(H29A,
 H29B,H29C), C58B(H58A,H58B,H58C), C54B(H54A,H54B,H54C), C35A(H35A,H35B,H35C),
 C40A(H40C,H40D,H40E), C50B(H50A,H50B,H50C), C6(H6A,H6B,H6C), C62B(H62A,H62B,
 H62C), C39A(H39C,H39D,H39E), C49B(H49A,H49B,H49C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              38514
_olex2_submission_special_instructions 'No special instructions were received'