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#$Date: 2023-07-05 12:14:20 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284874 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/16/7131687.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7131687
loop_
_publ_author_name
'Zhang, Ming'
'Nian, Beifang'
'Wu, Zhibang'
'Guo, Jianhua'
'Chen, Zhuo'
'Yuan, Caifeng'
'Huang, Xuankun'
'Shen, Yiwen'
'Zhang, Hongbin'
'Tang, E.'
_publ_section_title
;
 Molybdenum(V)-mediated switching of the C(sp²)-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       'φ and ω 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/[σ²(Fo²)+(0.0740P)²+7.0327P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mo1 Mo 0.83120(8) 1.15898(5) 0.15283(5) 0.0375(2) Uani 1 1 d . . . . .
Cl1 Cl 0.7599(3) 1.0891(2) 0.29454(16) 0.0603(6) Uani 1 1 d . . . . .
O2 O 0.7856(6) 0.9633(4) 0.0672(4) 0.0353(10) Uani 1 1 d . . . . .
H2A H 0.878456 0.941729 0.040751 0.053 Uiso 1 1 d R U . . .
H2B H 0.717400 0.950933 0.011377 0.053 Uiso 1 1 d R U . . .
Cl3 Cl 0.5483(2) 1.13871(17) 0.10299(16) 0.0486(5) Uani 1 1 d . . . . .
Cl4 Cl 0.8957(2) 1.17675(15) -0.01975(15) 0.0453(4) Uani 1 1 d . . . . .
Cl5 Cl 1.1013(2) 1.11798(15) 0.17371(14) 0.0423(4) Uani 1 1 d . . . . .
O1 O 0.8657(7) 1.2974(4) 0.2087(5) 0.0580(15) Uani 1 1 d . . . . .
Se1 Se 0.50988(8) 0.77303(5) 0.14541(5) 0.0318(2) Uani 1 1 d . . . . .
C1 C 0.4197(8) 0.8414(5) 0.2738(5) 0.0303(14) Uani 1 1 d . . . . .
C2 C 0.4165(8) 0.7914(6) 0.3569(6) 0.0398(16) Uani 1 1 d . . . . .
H2 H 0.460977 0.722608 0.352895 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3469(10) 0.8437(7) 0.4467(6) 0.051(2) Uani 1 1 d . . . . .
H3 H 0.340365 0.810062 0.504650 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2863(11) 0.9465(7) 0.4508(6) 0.055(2) Uani 1 1 d . . . . .
H4 H 0.241687 0.983973 0.512784 0.066 Uiso 1 1 calc R U . . .
C5 C 0.2906(11) 0.9932(7) 0.3676(7) 0.056(2) Uani 1 1 d . . . . .
H5 H 0.247076 1.062445 0.371894 0.067 Uiso 1 1 calc R U . . .
C6 C 0.3573(9) 0.9423(6) 0.2761(6) 0.0447(18) Uani 1 1 d . . . . .
H6 H 0.360019 0.975049 0.217565 0.054 Uiso 1 1 calc R U . . .
C7 C 0.4021(8) 0.6165(5) 0.1223(5) 0.0337(15) Uani 1 1 d . . . . .
C8 C 0.2444(9) 0.5769(6) 0.0840(6) 0.0419(17) Uani 1 1 d . . . . .
H8 H 0.174632 0.626928 0.067797 0.050 Uiso 1 1 calc R U . . .
C9 C 0.1892(11) 0.4592(7) 0.0696(7) 0.054(2) Uani 1 1 d . . . . .
H9 H 0.079312 0.428210 0.044005 0.065 Uiso 1 1 calc R U . . .
C10 C 0.2936(11) 0.3885(7) 0.0924(6) 0.052(2) Uani 1 1 d . . . . .
H10 H 0.254735 0.308681 0.080890 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4516(11) 0.4298(6) 0.1311(6) 0.0457(18) Uani 1 1 d . . . . .
H11 H 0.521292 0.379271 0.146534 0.055 Uiso 1 1 calc R U . . .
C12 C 0.5094(9) 0.5465(5) 0.1477(5) 0.0339(15) Uani 1 1 d . . . . .
C13 C 0.6729(9) 0.6065(6) 0.1896(5) 0.0355(15) Uani 1 1 d . . . . .
C14 C 0.8016(10) 0.5580(7) 0.2239(6) 0.051(2) Uani 1 1 d . . . . .
H14 H 0.789709 0.478026 0.219781 0.061 Uiso 1 1 calc R U . . .
C15 C 0.9462(10) 0.6292(9) 0.2640(7) 0.062(2) Uani 1 1 d . . . . .
H15 H 1.032908 0.596673 0.288293 0.074 Uiso 1 1 calc R U . . .
C16 C 0.9703(9) 0.7458(8) 0.2702(7) 0.056(2) Uani 1 1 d . . . . .
H16 H 1.071563 0.792059 0.298393 0.067 Uiso 1 1 calc R U . . .
C17 C 0.8437(9) 0.7947(7) 0.2346(6) 0.0454(18) Uani 1 1 d . . . . .
H17 H 0.857649 0.874110 0.235719 0.055 Uiso 1 1 calc R U . . .
C18 C 0.6976(8) 0.7237(6) 0.1976(5) 0.0345(15) Uani 1 1 d . . . . .
Cl6 Cl 0.8102(7) 0.6955(4) 0.5106(3) 0.1417(15) Uani 1 1 d D U . . .
Cl7 Cl 0.5389(6) 0.6834(4) 0.6342(3) 0.1263(14) Uani 1 1 d D U . . .
Cl8 Cl 0.7274(6) 0.5011(3) 0.6027(3) 0.1374(16) Uani 1 1 d D U . . .
C19 C 0.7343(13) 0.6460(7) 0.6161(7) 0.096(4) Uani 1 1 d D U . . .
D19 D 0.806477 0.687101 0.678787 0.116 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/anie.202211408 2023
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Mo1 O2 82.99(12) . . ?
Cl1 Mo1 Cl3 89.52(8) . . ?
Cl1 Mo1 Cl4 164.04(8) . . ?
Cl1 Mo1 Cl5 89.00(8) . . ?
O2 Mo1 Cl3 80.58(13) . . ?
O2 Mo1 Cl4 81.06(12) . . ?
O2 Mo1 Cl5 81.34(12) . . ?
Cl3 Mo1 Cl4 88.41(7) . . ?
Cl3 Mo1 Cl5 161.90(7) . . ?
Cl5 Mo1 Cl4 88.07(7) . . ?
O1 Mo1 Cl1 99.2(2) . . ?
O1 Mo1 O2 177.8(3) . . ?
O1 Mo1 Cl3 99.6(2) . . ?
O1 Mo1 Cl4 96.8(2) . . ?
O1 Mo1 Cl5 98.4(2) . . ?
Mo1 O2 H2A 110.4 . . ?
Mo1 O2 H2B 110.7 . . ?
H2A O2 H2B 103.3 . . ?
C1 Se1 C7 101.1(3) . . ?
C18 Se1 C1 100.0(3) . . ?
C18 Se1 C7 87.0(3) . . ?
C2 C1 Se1 121.3(5) . . ?
C2 C1 C6 122.9(7) . . ?
C6 C1 Se1 115.9(5) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.5(6) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(7) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(8) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(7) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 121.5 . . ?
C5 C6 C1 117.1(7) . . ?
C5 C6 H6 121.5 . . ?
C8 C7 Se1 125.5(5) . . ?
C8 C7 C12 123.6(6) . . ?
C12 C7 Se1 110.9(5) . . ?
C7 C8 H8 121.4 . . ?
C7 C8 C9 117.2(7) . . ?
C9 C8 H8 121.4 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(8) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.9(7) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.4(7) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C13 114.9(6) . . ?
C11 C12 C7 117.8(7) . . ?
C11 C12 C13 127.3(6) . . ?
C14 C13 C12 126.8(7) . . ?
C18 C13 C12 115.1(6) . . ?
C18 C13 C14 118.1(7) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.5(8) . . ?
C15 C14 H14 120.8 . . ?
C14 C15 H15 118.5 . . ?
C14 C15 C16 122.9(7) . . ?
C16 C15 H15 118.5 . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.1(8) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 121.1 . . ?
C18 C17 C16 117.7(7) . . ?
C18 C17 H17 121.1 . . ?
C13 C18 Se1 111.9(5) . . ?
C17 C18 Se1 124.4(5) . . ?
C17 C18 C13 123.6(6) . . ?
Cl6 C19 D19 108.3 . . ?
Cl7 C19 Cl6 107.1(5) . . ?
Cl7 C19 D19 108.3 . . ?
Cl8 C19 Cl6 114.2(5) . . ?
Cl8 C19 Cl7 110.6(6) . . ?
Cl8 C19 D19 108.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mo1 Cl1 2.286(2) . ?
Mo1 O2 2.355(4) . ?
Mo1 Cl3 2.3673(19) . ?
Mo1 Cl4 2.4097(19) . ?
Mo1 Cl5 2.3680(18) . ?
Mo1 O1 1.651(5) . ?
O2 H2A 0.8926 . ?
O2 H2B 0.8928 . ?
Se1 C1 1.924(7) . ?
Se1 C7 1.927(6) . ?
Se1 C18 1.909(6) . ?
C1 C2 1.376(9) . ?
C1 C6 1.390(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.352(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.360(10) . ?
C7 C12 1.399(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.400(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(12) . ?
C10 H10 0.9500 . ?
C10 C11 1.367(12) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(10) . ?
C12 C13 1.464(10) . ?
C13 C14 1.401(10) . ?
C13 C18 1.385(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(13) . ?
C16 H16 0.9500 . ?
C16 C17 1.398(11) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(10) . ?
Cl6 C19 1.736(8) . ?
Cl7 C19 1.735(9) . ?
Cl8 C19 1.719(8) . ?
C19 D19 1.0000 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 C1 C2 C3 -178.7(6) . . . . ?
Se1 C1 C6 C5 179.7(6) . . . . ?
Se1 C7 C8 C9 178.1(6) . . . . ?
Se1 C7 C12 C11 -177.4(5) . . . . ?
Se1 C7 C12 C13 2.6(7) . . . . ?
C1 C2 C3 C4 -1.6(12) . . . . ?
C2 C1 C6 C5 0.5(11) . . . . ?
C2 C3 C4 C5 2.0(14) . . . . ?
C3 C4 C5 C6 -1.1(14) . . . . ?
C4 C5 C6 C1 -0.2(13) . . . . ?
C6 C1 C2 C3 0.4(11) . . . . ?
C7 C8 C9 C10 -0.9(12) . . . . ?
C7 C12 C13 C14 178.0(7) . . . . ?
C7 C12 C13 C18 -0.1(9) . . . . ?
C8 C7 C12 C11 1.1(10) . . . . ?
C8 C7 C12 C13 -178.9(6) . . . . ?
C8 C9 C10 C11 1.2(13) . . . . ?
C9 C10 C11 C12 -0.3(12) . . . . ?
C10 C11 C12 C7 -0.9(10) . . . . ?
C10 C11 C12 C13 179.2(7) . . . . ?
C11 C12 C13 C14 -2.1(12) . . . . ?
C11 C12 C13 C18 179.8(7) . . . . ?
C12 C7 C8 C9 -0.2(11) . . . . ?
C12 C13 C14 C15 -178.1(7) . . . . ?
C12 C13 C18 Se1 -2.4(7) . . . . ?
C12 C13 C18 C17 -179.6(6) . . . . ?
C13 C14 C15 C16 -1.0(13) . . . . ?
C14 C13 C18 Se1 179.3(5) . . . . ?
C14 C13 C18 C17 2.1(11) . . . . ?
C14 C15 C16 C17 -0.1(14) . . . . ?
C15 C16 C17 C18 2.1(12) . . . . ?
C16 C17 C18 Se1 -180.0(6) . . . . ?
C16 C17 C18 C13 -3.1(11) . . . . ?
C18 C13 C14 C15 0.0(11) . . . . ?
