#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/08/7120803.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_7120803
loop_
_publ_author_name
'Imbrich, Dominik'
'Frey, Wolfgang'
'Buchmeiser, Michael R.'
_publ_section_title
;
 N-Heterocyclic Carbene-Induced Transmethylation in Tungsten Imido
 Alkylidene Bistriflates: Unexpected Formation of an N-Heterocyclic Olefin
 Complex
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC07471A
_journal_year                    2017
_chemical_formula_moiety         'C22 H29 N2, C F3 O3 S'
_chemical_formula_sum            'C23 H29 F3 N2 O3 S'
_chemical_formula_weight         470.54
_chemical_name_systematic
; 
 compound 3 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-07-05 deposited with the CCDC.
2017-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.907(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.596(3)
_cell_length_b                   10.814(2)
_cell_length_c                   23.235(6)
_cell_measurement_reflns_used    2227
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      1.75
_cell_volume                     2662.1(11)
_computing_cell_refinement       'Bruker APEXII Software Suite, 2008'
_computing_data_collection       'Bruker APEXII Software Suite, 2008'
_computing_data_reduction        'Bruker APEXII Software Suite, 2008'
_computing_molecular_graphics    'SHELXTL-plus, XP (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'Omega + Phi Scans'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1106
_diffrn_reflns_av_sigmaI/netI    0.1547
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16999
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7339
_exptl_absorpt_correction_T_min  0.6288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_platon_squeeze_details
;
;
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4645
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1828
_refine_ls_R_factor_gt           0.0983
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0564P)²+7.4512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1981
_refine_ls_wR_factor_ref         0.2239
_reflns_number_gt                2227
_reflns_number_total             4645
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc07471a2.cif
_cod_data_source_block           buch99
_cod_original_cell_volume        2662.0(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7120803
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.51992(17) 0.95885(15) 0.77043(7) 0.0326(5) Uani 1 1 d D . .
O1 O 0.4532(5) 0.8523(4) 0.75091(19) 0.0486(13) Uani 1 1 d . A .
O2 O 0.4530(7) 1.0706(4) 0.7603(2) 0.081(2) Uani 1 1 d . A .
O3 O 0.6506(12) 0.980(2) 0.7606(17) 0.062(8) Uani 0.50 1 d PD A 1
O3A O 0.6475(11) 0.927(2) 0.7591(17) 0.060(8) Uani 0.50 1 d PD A 2
C23 C 0.5152(6) 0.9446(6) 0.8492(3) 0.0386(17) Uani 1 1 d D A .
F1 F 0.5692(4) 0.8418(4) 0.86747(16) 0.0583(13) Uani 1 1 d . . .
F2 F 0.6015(10) 1.0234(9) 0.8719(4) 0.050(3) Uani 0.50 1 d PDU A 1
F2A F 0.5339(11) 1.0443(8) 0.8783(4) 0.046(3) Uani 0.50 1 d PDU A 2
F3 F 0.3968(5) 0.9308(5) 0.86671(19) 0.0903(18) Uani 1 1 d . . .
N1 N -0.0089(5) 0.9896(4) 0.19933(19) 0.0235(12) Uani 1 1 d . . .
C1 C -0.0527(5) 1.0410(5) 0.2458(2) 0.0194(13) Uani 1 1 d . . .
N2 N 0.0040(4) 0.9989(4) 0.29334(19) 0.0203(11) Uani 1 1 d . . .
C2 C 0.0940(6) 0.9008(5) 0.2137(2) 0.0263(15) Uani 1 1 d . . .
H2A H 0.1746 0.9263 0.1964 0.032 Uiso 1 1 calc R . .
H2B H 0.0724 0.8162 0.2005 0.032 Uiso 1 1 calc R . .
C3 C 0.1015(6) 0.9076(5) 0.2793(2) 0.0251(14) Uani 1 1 d . . .
H3A H 0.0830 0.8263 0.2968 0.030 Uiso 1 1 calc R . .
H3B H 0.1860 0.9355 0.2926 0.030 Uiso 1 1 calc R . .
C4 C -0.0473(5) 1.0190(5) 0.1413(2) 0.0228(14) Uani 1 1 d . . .
C5 C -0.1350(6) 0.9440(6) 0.1137(2) 0.0293(15) Uani 1 1 d . . .
C6 C -0.1737(6) 0.9734(6) 0.0587(3) 0.0352(16) Uani 1 1 d . . .
H6 H -0.2337 0.9224 0.0392 0.042 Uiso 1 1 calc R . .
C7 C -0.1249(7) 1.0793(7) 0.0306(3) 0.0380(18) Uani 1 1 d . . .
C8 C -0.0371(6) 1.1509(6) 0.0594(3) 0.0326(16) Uani 1 1 d . . .
H8 H -0.0033 1.2211 0.0406 0.039 Uiso 1 1 calc R . .
C9 C 0.0035(6) 1.1240(6) 0.1149(3) 0.0303(15) Uani 1 1 d . . .
C10 C -0.1939(6) 0.8352(6) 0.1448(3) 0.0402(18) Uani 1 1 d . . .
H10A H -0.1271 0.7836 0.1619 0.060 Uiso 1 1 calc R . .
H10B H -0.2439 0.7859 0.1174 0.060 Uiso 1 1 calc R . .
H10C H -0.2487 0.8659 0.1753 0.060 Uiso 1 1 calc R . .
C11 C -0.1714(7) 1.1115(7) -0.0300(3) 0.054(2) Uani 1 1 d . . .
H11A H -0.2294 1.1820 -0.0282 0.081 Uiso 1 1 calc R . .
H11B H -0.2155 1.0402 -0.0468 0.081 Uiso 1 1 calc R . .
H11C H -0.0993 1.1332 -0.0539 0.081 Uiso 1 1 calc R . .
C12 C 0.0990(7) 1.2033(6) 0.1460(3) 0.0402(18) Uani 1 1 d . . .
H12A H 0.0565 1.2532 0.1751 0.060 Uiso 1 1 calc R . .
H12B H 0.1403 1.2579 0.1184 0.060 Uiso 1 1 calc R . .
H12C H 0.1624 1.1504 0.1648 0.060 Uiso 1 1 calc R . .
C13 C -0.0256(5) 1.0384(5) 0.3507(2) 0.0206(13) Uani 1 1 d . . .
C14 C -0.1244(6) 0.9797(6) 0.3803(3) 0.0311(15) Uani 1 1 d . . .
C15 C -0.1520(7) 1.0202(6) 0.4339(3) 0.0368(17) Uani 1 1 d . . .
H15 H -0.2186 0.9818 0.4542 0.044 Uiso 1 1 calc R . .
C16 C -0.0851(7) 1.1166(6) 0.4601(3) 0.0343(17) Uani 1 1 d . . .
C17 C 0.0116(7) 1.1722(6) 0.4300(3) 0.0354(17) Uani 1 1 d . . .
H17 H 0.0574 1.2380 0.4475 0.042 Uiso 1 1 calc R . .
C18 C 0.0430(6) 1.1353(5) 0.3757(3) 0.0279(15) Uani 1 1 d . . .
C19 C -0.2006(6) 0.8751(6) 0.3511(3) 0.0385(17) Uani 1 1 d . . .
H19A H -0.2393 0.8233 0.3806 0.058 Uiso 1 1 calc R . .
H19B H -0.1441 0.8245 0.3278 0.058 Uiso 1 1 calc R . .
H19C H -0.2667 0.9109 0.3263 0.058 Uiso 1 1 calc R . .
C20 C -0.1193(8) 1.1608(7) 0.5199(3) 0.056(2) Uani 1 1 d . . .
H20A H -0.0567 1.2214 0.5334 0.083 Uiso 1 1 calc R . .
H20B H -0.1202 1.0902 0.5464 0.083 Uiso 1 1 calc R . .
H20C H -0.2030 1.1994 0.5186 0.083 Uiso 1 1 calc R . .
C21 C 0.1456(6) 1.1982(5) 0.3436(3) 0.0370(17) Uani 1 1 d . . .
H21A H 0.1882 1.2582 0.3689 0.055 Uiso 1 1 calc R . .
H21B H 0.1093 1.2412 0.3101 0.055 Uiso 1 1 calc R . .
H21C H 0.2068 1.1365 0.3307 0.055 Uiso 1 1 calc R . .
C22 C -0.1518(7) 1.1367(6) 0.2465(3) 0.0345(17) Uani 1 1 d D . .
H22A H -0.197(4) 1.143(5) 0.2106(12) 0.052 Uiso 1 1 d D . .
H22B H -0.116(5) 1.215(3) 0.2544(19) 0.052 Uiso 1 1 d D . .
H22C H -0.210(4) 1.118(5) 0.2758(15) 0.052 Uiso 1 1 d D . .
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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O1 113.1(3)
O2 S1 O3A 130.4(12)
O1 S1 O3A 102.4(10)
O2 S1 O3 108.9(11)
O1 S1 O3 123.8(11)
O3A S1 O3 23.1(15)
O2 S1 C23 102.4(3)
O1 S1 C23 103.2(3)
O3A S1 C23 101.8(17)
O3 S1 C23 102.4(17)
F2A C23 F1 118.4(7)
F2A C23 F3 94.1(7)
F1 C23 F3 102.3(6)
F2A C23 F2 33.8(5)
F1 C23 F2 96.9(7)
F3 C23 F2 125.9(8)
F2A C23 S1 116.5(7)
F1 C23 S1 111.9(4)
F3 C23 S1 110.7(4)
F2 C23 S1 107.8(6)
C1 N1 C4 125.6(5)
C1 N1 C2 111.0(4)
C4 N1 C2 123.3(4)
N1 C1 N2 112.3(5)
N1 C1 C22 124.8(5)
N2 C1 C22 122.9(5)
C1 N2 C13 124.5(4)
C1 N2 C3 110.9(4)
C13 N2 C3 124.7(4)
N1 C2 C3 102.7(4)
N1 C2 H2A 111.2
C3 C2 H2A 111.2
N1 C2 H2B 111.2
C3 C2 H2B 111.2
H2A C2 H2B 109.1
N2 C3 C2 103.2(4)
N2 C3 H3A 111.1
C2 C3 H3A 111.1
N2 C3 H3B 111.1
C2 C3 H3B 111.1
H3A C3 H3B 109.1
C5 C4 C9 122.0(5)
C5 C4 N1 119.0(5)
C9 C4 N1 119.0(5)
C6 C5 C4 119.0(6)
C6 C5 C10 120.2(6)
C4 C5 C10 120.6(5)
C5 C6 C7 120.6(6)
C5 C6 H6 119.7
C7 C6 H6 119.7
C8 C7 C6 118.6(6)
C8 C7 C11 121.8(7)
C6 C7 C11 119.6(7)
C7 C8 C9 122.3(6)
C7 C8 H8 118.9
C9 C8 H8 118.9
C8 C9 C4 117.5(6)
C8 C9 C12 121.8(6)
C4 C9 C12 120.7(5)
C5 C10 H10A 109.5
C5 C10 H10B 109.5
H10A C10 H10B 109.5
C5 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C7 C11 H11A 109.5
C7 C11 H11B 109.5
H11A C11 H11B 109.5
C7 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C9 C12 H12A 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
C9 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C18 C13 C14 121.3(5)
C18 C13 N2 119.2(5)
C14 C13 N2 119.5(5)
C15 C14 C13 118.3(6)
C15 C14 C19 121.5(6)
C13 C14 C19 120.1(5)
C14 C15 C16 121.7(6)
C14 C15 H15 119.1
C16 C15 H15 119.1
C17 C16 C15 118.6(6)
C17 C16 C20 120.9(6)
C15 C16 C20 120.5(7)
C18 C17 C16 122.1(6)
C18 C17 H17 119.0
C16 C17 H17 119.0
C17 C18 C13 118.0(6)
C17 C18 C21 121.2(6)
C13 C18 C21 120.8(5)
C14 C19 H19A 109.5
C14 C19 H19B 109.5
H19A C19 H19B 109.5
C14 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C16 C20 H20A 109.5
C16 C20 H20B 109.5
H20A C20 H20B 109.5
C16 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C18 C21 H21A 109.5
C18 C21 H21B 109.5
H21A C21 H21B 109.5
C18 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C1 C22 H22A 113(4)
C1 C22 H22B 110(4)
H22A C22 H22B 107(2)
C1 C22 H22C 109(4)
H22A C22 H22C 108(3)
H22B C22 H22C 109(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.419(5)
S1 O1 1.422(5)
S1 O3A 1.423(9)
S1 O3 1.424(9)
S1 C23 1.839(7)
C23 F2A 1.286(8)
C23 F1 1.317(7)
C23 F3 1.333(8)
C23 F2 1.351(8)
N1 C1 1.306(7)
N1 C4 1.437(7)
N1 C2 1.488(7)
C1 N2 1.330(7)
C1 C22 1.474(8)
N2 C13 1.439(7)
N2 C3 1.470(7)
C2 C3 1.526(8)
C2 H2A 0.9900
C2 H2B 0.9900
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.384(8)
C4 C9 1.403(8)
C5 C6 1.373(8)
C5 C10 1.521(8)
C6 C7 1.420(9)
C6 H6 0.9500
C7 C8 1.376(9)
C7 C11 1.524(9)
C8 C9 1.383(8)
C8 H8 0.9500
C9 C12 1.502(9)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C18 1.397(8)
C13 C14 1.412(8)
C14 C15 1.357(8)
C14 C19 1.541(8)
C15 C16 1.394(9)
C15 H15 0.9500
C16 C17 1.387(9)
C16 C20 1.520(8)
C17 C18 1.367(8)
C17 H17 0.9500
C18 C21 1.493(8)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C22 H22A 0.960(16)
C22 H22B 0.95(2)
C22 H22C 0.95(2)
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
O2 S1 C23 F2A -41.9(8)
O1 S1 C23 F2A -159.6(7)
O3A S1 C23 F2A 94.5(12)
O3 S1 C23 F2A 70.9(12)
O2 S1 C23 F1 177.4(5)
O1 S1 C23 F1 59.7(5)
O3A S1 C23 F1 -46.2(10)
O3 S1 C23 F1 -69.8(11)
O2 S1 C23 F3 64.0(6)
O1 S1 C23 F3 -53.7(6)
O3A S1 C23 F3 -159.6(10)
O3 S1 C23 F3 176.9(11)
O2 S1 C23 F2 -77.2(7)
O1 S1 C23 F2 165.1(7)
O3A S1 C23 F2 59.2(11)
O3 S1 C23 F2 35.6(12)
C4 N1 C1 N2 -177.4(5)
C2 N1 C1 N2 -1.2(7)
C4 N1 C1 C22 1.4(9)
C2 N1 C1 C22 177.6(5)
N1 C1 N2 C13 -179.5(5)
C22 C1 N2 C13 1.6(9)
N1 C1 N2 C3 0.9(7)
C22 C1 N2 C3 -178.0(5)
C1 N1 C2 C3 1.0(6)
C4 N1 C2 C3 177.3(5)
C1 N2 C3 C2 -0.2(6)
C13 N2 C3 C2 -179.8(5)
N1 C2 C3 N2 -0.5(6)
C1 N1 C4 C5 -98.6(7)
C2 N1 C4 C5 85.7(7)
C1 N1 C4 C9 80.2(7)
C2 N1 C4 C9 -95.5(7)
C9 C4 C5 C6 -0.1(9)
N1 C4 C5 C6 178.7(5)
C9 C4 C5 C10 -176.4(6)
N1 C4 C5 C10 2.4(8)
C4 C5 C6 C7 -0.2(9)
C10 C5 C6 C7 176.1(6)
C5 C6 C7 C8 0.7(9)
C5 C6 C7 C11 -178.7(6)
C6 C7 C8 C9 -0.9(9)
C11 C7 C8 C9 178.5(6)
C7 C8 C9 C4 0.6(9)
C7 C8 C9 C12 -179.7(6)
C5 C4 C9 C8 -0.1(9)
N1 C4 C9 C8 -178.9(5)
C5 C4 C9 C12 -179.8(6)
N1 C4 C9 C12 1.5(8)
C1 N2 C13 C18 -93.0(7)
C3 N2 C13 C18 86.5(7)
C1 N2 C13 C14 86.0(7)
C3 N2 C13 C14 -94.4(7)
C18 C13 C14 C15 0.3(9)
N2 C13 C14 C15 -178.8(5)
C18 C13 C14 C19 178.5(5)
N2 C13 C14 C19 -0.5(8)
C13 C14 C15 C16 -0.4(9)
C19 C14 C15 C16 -178.6(6)
C14 C15 C16 C17 0.3(10)
C14 C15 C16 C20 179.3(6)
C15 C16 C17 C18 -0.1(9)
C20 C16 C17 C18 -179.1(6)
C16 C17 C18 C13 0.0(9)
C16 C17 C18 C21 178.7(6)
C14 C13 C18 C17 -0.1(9)
N2 C13 C18 C17 179.0(5)
C14 C13 C18 C21 -178.8(5)
N2 C13 C18 C21 0.2(8)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 1.000 171 47 ' '
2 0.000 0.500 0.500 33 2 ' '
3 0.500 0.000 0.500 171 47 ' '
4 0.500 1.000 1.000 33 2 ' '
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188142
