Molybdenum(V)-mediated switching of the C(sp<sup>2</sup>)-Se bond of phenylselenyl-functionalized arenes or heterocycles under mild conditions.
Zhang, Ming; Nian, Beifang; Wu, Zhibang; Guo, Jianhua; Chen, Zhuo; Yuan, Caifeng; Huang, Xuankun; Shen, Yiwen; Zhang, Hongbin; Tang, E.; Chemical communications (Cambridge, England) 59 (2023) 7599–7602; doi:10.1039/d3cc01119d

data_7131687
_publ_section_title
;
 Molybdenum(V)-mediated switching of the C(sp<sup>2</sup>)-Se bond of
 phenylselenyl-functionalized arenes or heterocycles under mild
 conditions.
;
_journal_issue                   49
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7599
_journal_page_last               7602
_journal_paper_doi               10.1039/d3cc01119d
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C18 H13 Se, Cl4 H2 Mo O2, C D Cl3'
_chemical_formula_sum            'C19 H15 Cl7 D Mo O2 Se'
_chemical_formula_weight         700.37
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2clwc7
_audit_creation_date             2022-05-24
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-27 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                103.403(5)
_cell_angle_beta                 90.813(6)
_cell_angle_gamma                98.443(5)
_cell_formula_units_Z            2
_cell_length_a                   8.2075(12)
_cell_length_b                   12.1341(16)
_cell_length_c                   13.2766(19)
_cell_measurement_reflns_used    8656
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.51
_cell_volume                     1270.7(3)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0607
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15684
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.059
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.699
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            'light green'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_description       'needle-like crystals'
_exptl_crystal_F_000             682
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.715
_refine_diff_density_min         -1.560
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4475
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0572
_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^)+(0.0740P)^2^+7.0327P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1569
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3446
_reflns_number_total             4475
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01119d2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7131687--7131688.cif.'
_cod_original_formula_sum        'C19 H15  D Cl7 Mo O2 Se'
_cod_database_code               7131687
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.774
_shelx_estimated_absorpt_t_min   0.642
_exptl_absorpt_special_details
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71098    8.210   12.137   13.289  103.359   90.760   98.467
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 C19-Cl7 = C19-Cl6 = C19-Cl8
 1.78 with sigma of 0.02
 C19-Cl7 \\sim C19-Cl6 \\sim C19-Cl8
 with sigma of 0.02
 Cl7-Cl6 \\sim Cl6-Cl8 \\sim Cl8-Cl7
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Cl6 \\sim Cl7 \\sim Cl8 \\sim C19: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
Uanis(Cl6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.005
4. Rigid body (RIGU) restrains
 Cl6, Cl7, Cl8, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Rotating group:
 O2(H2A,H2B)
5.b Ternary CH refined with riding coordinates:
 C19(D19)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C15(H15), C16(H16), C17(H17)
;
_shelx_res_checksum              12000
_shelx_hkl_checksum              14384
_olex2_submission_special_instructions 'No special instructions were received'