#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:42:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178578 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/88/4068829.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_4068829
loop_
_publ_author_name
'Beer, Stephan'
'Brandhorst, Kai'
'Hrib, Cristian G.'
'Wu, Xian'
'Haberlag, Birte'
'Grunenberg, Jörg'
'Jones, Peter G.'
'Tamm, Matthias'
_publ_section_title
;
 Experimental and Theoretical Investigations of Catalytic Alkyne
 Cross-Metathesis with Imidazolin-2-iminato Tungsten Alkylidyne Complexes
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1534
_journal_paper_doi               10.1021/om801119t
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C17 H19 Cl F18 O4 W'
_chemical_formula_weight         848.62
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.170(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7756(10)
_cell_length_b                   10.5201(10)
_cell_length_c                   23.197(2)
_cell_measurement_reflns_used    9738
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     2579.8(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'ω- and φ-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            46874
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    4.736
_exptl_absorpt_correction_T_max  0.5179
_exptl_absorpt_correction_T_min  0.2880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.245
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    'rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         6392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0163
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0179P)²+2.3880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0373
_refine_ls_wR_factor_ref         0.0389
_reflns_number_gt                5777
_reflns_number_total             6392
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om801119t_si_009.cif
_cod_data_source_block           9
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4068829
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
W W 0.217101(7) 0.272741(7) 0.585695(3) 0.01303(3) Uani 1 1 d .
Cl Cl 0.00281(4) 0.31887(5) 0.54404(2) 0.02148(10) Uani 1 1 d .
O1 O 0.23984(14) 0.29598(13) 0.49493(6) 0.0191(3) Uani 1 1 d .
O2 O 0.15672(14) 0.07371(14) 0.53460(7) 0.0220(3) Uani 1 1 d .
O3 O 0.17282(13) 0.18403(14) 0.65178(6) 0.0181(3) Uani 1 1 d .
O4 O 0.38110(13) 0.18518(14) 0.59302(6) 0.0168(3) Uani 1 1 d .
C1 C 0.25505(18) 0.42993(18) 0.60980(8) 0.0151(4) Uani 1 1 d .
C2 C 0.2704(2) 0.56778(19) 0.62635(9) 0.0200(4) Uani 1 1 d .
C3 C 0.3417(2) 0.5856(2) 0.68988(10) 0.0292(5) Uani 1 1 d .
H3A H 0.2956 0.5427 0.7168 0.044 Uiso 1 1 calc R
H3B H 0.3485 0.6765 0.6992 0.044 Uiso 1 1 calc R
H3C H 0.4267 0.5489 0.6942 0.044 Uiso 1 1 calc R
C4 C 0.1368(2) 0.6249(2) 0.61958(10) 0.0264(5) Uani 1 1 d .
H4A H 0.0933 0.6183 0.5785 0.040 Uiso 1 1 calc R
H4B H 0.1432 0.7146 0.6313 0.040 Uiso 1 1 calc R
H4C H 0.0889 0.5783 0.6446 0.040 Uiso 1 1 calc R
C5 C 0.3428(3) 0.6378(2) 0.58502(11) 0.0308(5) Uani 1 1 d .
H5A H 0.4220 0.5929 0.5841 0.046 Uiso 1 1 calc R
H5B H 0.3615 0.7247 0.5993 0.046 Uiso 1 1 calc R
H5C H 0.2909 0.6404 0.5454 0.046 Uiso 1 1 calc R
C6 C 0.1851(2) 0.1972(2) 0.45375(9) 0.0251(5) Uani 1 1 d .
H6A H 0.2234 0.2005 0.4183 0.030 Uiso 1 1 calc R
H6B H 0.0929 0.2109 0.4415 0.030 Uiso 1 1 calc R
C7 C 0.2096(2) 0.0706(2) 0.48268(10) 0.0263(5) Uani 1 1 d .
H7A H 0.1696 0.0025 0.4560 0.032 Uiso 1 1 calc R
H7B H 0.3017 0.0541 0.4929 0.032 Uiso 1 1 calc R
C8 C 0.2320(2) 0.4191(2) 0.46599(10) 0.0279(5) Uani 1 1 d .
H8A H 0.2587 0.4108 0.4281 0.042 Uiso 1 1 calc R
H8B H 0.2874 0.4796 0.4908 0.042 Uiso 1 1 calc R
H8C H 0.1445 0.4499 0.4595 0.042 Uiso 1 1 calc R
C9 C 0.1685(3) -0.0467(2) 0.56416(12) 0.0325(5) Uani 1 1 d .
H9A H 0.1299 -0.1131 0.5368 0.049 Uiso 1 1 calc R
H9B H 0.1254 -0.0431 0.5976 0.049 Uiso 1 1 calc R
H9C H 0.2582 -0.0662 0.5782 0.049 Uiso 1 1 calc R
C10 C 0.1310(2) 0.1730(2) 0.70359(9) 0.0210(4) Uani 1 1 d .
C11 C 0.1628(3) 0.2910(3) 0.74376(12) 0.0353(6) Uani 1 1 d .
C12 C -0.0150(2) 0.1546(3) 0.68926(12) 0.0360(6) Uani 1 1 d .
C13 C 0.1955(2) 0.0538(2) 0.73601(11) 0.0314(5) Uani 1 1 d .
C14 C 0.50985(18) 0.1960(2) 0.60923(9) 0.0169(4) Uani 1 1 d .
C15 C 0.5533(2) 0.2858(2) 0.66281(10) 0.0213(4) Uani 1 1 d .
C16 C 0.5591(2) 0.0590(2) 0.62656(10) 0.0224(4) Uani 1 1 d .
C17 C 0.5661(2) 0.2447(2) 0.55644(10) 0.0249(5) Uani 1 1 d .
F1 F 0.28534(17) 0.3004(2) 0.76388(8) 0.0559(5) Uani 1 1 d .
F2 F 0.1248(2) 0.39647(15) 0.71425(8) 0.0560(5) Uani 1 1 d .
F3 F 0.10722(19) 0.28760(16) 0.79044(7) 0.0486(4) Uani 1 1 d .
F4 F -0.04677(16) 0.0713(2) 0.64627(8) 0.0612(6) Uani 1 1 d .
F5 F -0.06005(15) 0.1147(2) 0.73548(8) 0.0517(5) Uani 1 1 d .
F6 F -0.07339(17) 0.2622(2) 0.67169(9) 0.0604(6) Uani 1 1 d .
F7 F 0.1482(2) -0.05152(15) 0.70933(8) 0.0563(5) Uani 1 1 d .
F8 F 0.31793(15) 0.05493(18) 0.73635(8) 0.0520(5) Uani 1 1 d .
F9 F 0.17996(17) 0.04628(17) 0.79129(7) 0.0487(4) Uani 1 1 d .
F10 F 0.47827(13) 0.27463(13) 0.70151(6) 0.0264(3) Uani 1 1 d .
F11 F 0.55095(13) 0.40735(13) 0.64574(6) 0.0295(3) Uani 1 1 d .
F12 F 0.67151(12) 0.26084(14) 0.69024(6) 0.0291(3) Uani 1 1 d .
F13 F 0.68430(12) 0.04752(14) 0.63134(7) 0.0348(3) Uani 1 1 d .
F14 F 0.52992(13) 0.02549(13) 0.67733(6) 0.0309(3) Uani 1 1 d .
F15 F 0.50567(13) -0.02498(13) 0.58642(6) 0.0308(3) Uani 1 1 d .
F16 F 0.55005(14) 0.15821(15) 0.51365(6) 0.0353(3) Uani 1 1 d .
F17 F 0.50788(13) 0.35023(14) 0.53406(6) 0.0304(3) Uani 1 1 d .
F18 F 0.68916(13) 0.26969(16) 0.57131(7) 0.0360(3) Uani 1 1 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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
W W -0.8490 6.8722 '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
C1 W O3 106.17(8)
C1 W O4 105.15(8)
O3 W O4 93.50(6)
C1 W O1 97.94(7)
O3 W O1 155.76(6)
O4 W O1 82.47(6)
C1 W Cl 94.86(6)
O3 W Cl 92.95(4)
O4 W Cl 156.32(4)
O1 W Cl 82.32(4)
C1 W O2 169.47(7)
O3 W O2 83.51(6)
O4 W O2 77.90(5)
O1 W O2 72.27(5)
Cl W O2 80.23(4)
C8 O1 C6 110.66(16)
C8 O1 W 122.58(12)
C6 O1 W 116.52(12)
C7 O2 C9 111.72(17)
C7 O2 W 108.51(12)
C9 O2 W 122.48(14)
C10 O3 W 155.81(14)
C14 O4 W 145.92(13)
C2 C1 W 172.64(16)
C1 C2 C3 111.90(18)
C1 C2 C5 110.35(17)
C3 C2 C5 108.67(19)
C1 C2 C4 107.27(18)
C3 C2 C4 109.55(18)
C5 C2 C4 109.06(18)
O1 C6 C7 109.15(17)
O2 C7 C6 107.11(17)
O3 C10 C11 112.86(18)
O3 C10 C13 107.49(17)
C11 C10 C13 109.2(2)
O3 C10 C12 108.32(18)
C11 C10 C12 109.0(2)
C13 C10 C12 109.96(19)
F1 C11 F2 108.0(2)
F1 C11 F3 106.9(2)
F2 C11 F3 107.4(2)
F1 C11 C10 111.3(2)
F2 C11 C10 110.5(2)
F3 C11 C10 112.6(2)
F6 C12 F4 107.3(2)
F6 C12 F5 107.0(2)
F4 C12 F5 108.6(2)
F6 C12 C10 111.1(2)
F4 C12 C10 110.3(2)
F5 C12 C10 112.3(2)
F8 C13 F7 107.8(2)
F8 C13 F9 108.0(2)
F7 C13 F9 107.0(2)
F8 C13 C10 110.43(19)
F7 C13 C10 110.7(2)
F9 C13 C10 112.8(2)
O4 C14 C17 109.85(17)
O4 C14 C15 113.63(16)
C17 C14 C15 109.01(17)
O4 C14 C16 105.62(17)
C17 C14 C16 110.00(17)
C15 C14 C16 108.64(17)
F10 C15 F12 108.11(18)
F10 C15 F11 107.86(17)
F12 C15 F11 106.91(17)
F10 C15 C14 110.97(17)
F12 C15 C14 111.84(17)
F11 C15 C14 110.96(17)
F14 C16 F15 107.52(18)
F14 C16 F13 108.16(18)
F15 C16 F13 106.89(17)
F14 C16 C14 110.33(17)
F15 C16 C14 110.69(17)
F13 C16 C14 113.03(18)
F17 C17 F18 107.87(19)
F17 C17 F16 107.20(19)
F18 C17 F16 107.88(18)
F17 C17 C14 110.86(17)
F18 C17 C14 112.46(18)
F16 C17 C14 110.37(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
W C1 1.768(2)
W O3 1.9319(14)
W O4 1.9708(14)
W O1 2.1800(14)
W Cl 2.3742(5)
W O2 2.4317(15)
O1 C8 1.454(3)
O1 C6 1.457(3)
O2 C7 1.429(3)
O2 C9 1.434(3)
O3 C10 1.368(2)
O4 C14 1.370(2)
C1 C2 1.501(3)
C2 C3 1.536(3)
C2 C5 1.536(3)
C2 C4 1.539(3)
C6 C7 1.491(3)
C10 C11 1.550(3)
C10 C13 1.555(3)
C10 C12 1.556(3)
C11 F1 1.316(3)
C11 F2 1.326(3)
C11 F3 1.336(3)
C12 F6 1.320(3)
C12 F4 1.322(3)
C12 F5 1.328(3)
C13 F8 1.317(3)
C13 F7 1.323(3)
C13 F9 1.327(3)
C14 C17 1.554(3)
C14 C15 1.559(3)
C14 C16 1.562(3)
C15 F10 1.325(2)
C15 F12 1.335(2)
C15 F11 1.337(3)
C16 F14 1.324(3)
C16 F15 1.331(3)
C16 F13 1.338(2)
C17 F17 1.330(3)
C17 F18 1.330(3)
C17 F16 1.333(3)
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
C1 W O1 C8 -22.24(17)
O3 W O1 C8 151.68(17)
O4 W O1 C8 -126.58(16)
Cl W O1 C8 71.63(15)
O2 W O1 C8 153.78(17)
C1 W O1 C6 -164.13(14)
O3 W O1 C6 9.8(2)
O4 W O1 C6 91.53(14)
Cl W O1 C6 -70.26(13)
O2 W O1 C6 11.89(13)
C1 W O2 C7 41.4(4)
O3 W O2 C7 -161.56(13)
O4 W O2 C7 -66.56(13)
O1 W O2 C7 19.30(13)
Cl W O2 C7 104.30(13)
C1 W O2 C9 173.9(4)
O3 W O2 C9 -29.05(16)
O4 W O2 C9 65.95(16)
O1 W O2 C9 151.82(17)
Cl W O2 C9 -123.19(16)
C1 W O3 C10 24.7(3)
O4 W O3 C10 131.6(3)
O1 W O3 C10 -149.0(3)
Cl W O3 C10 -71.2(3)
O2 W O3 C10 -151.0(3)
C1 W O4 C14 0.7(2)
O3 W O4 C14 -107.1(2)
O1 W O4 C14 96.9(2)
Cl W O4 C14 147.38(18)
O2 W O4 C14 170.3(2)
O3 W C1 C2 -99.1(12)
O4 W C1 C2 162.6(12)
O1 W C1 C2 78.3(12)
Cl W C1 C2 -4.6(12)
O2 W C1 C2 57.1(14)
W C1 C2 C3 139.0(12)
W C1 C2 C5 -99.9(12)
W C1 C2 C4 18.8(13)
C8 O1 C6 C7 172.76(18)
W O1 C6 C7 -41.0(2)
C9 O2 C7 C6 176.54(19)
W O2 C7 C6 -45.48(19)
O1 C6 C7 O2 57.2(2)
W O3 C10 C11 -30.9(4)
W O3 C10 C13 -151.4(3)
W O3 C10 C12 89.9(4)
O3 C10 C11 F1 -68.5(3)
C13 C10 C11 F1 50.9(3)
C12 C10 C11 F1 171.1(2)
O3 C10 C11 F2 51.4(3)
C13 C10 C11 F2 170.9(2)
C12 C10 C11 F2 -69.0(2)
O3 C10 C11 F3 171.4(2)
C13 C10 C11 F3 -69.1(3)
C12 C10 C11 F3 51.1(3)
O3 C10 C12 F6 -74.4(3)
C11 C10 C12 F6 48.8(3)
C13 C10 C12 F6 168.4(2)
O3 C10 C12 F4 44.5(3)
C11 C10 C12 F4 167.6(2)
C13 C10 C12 F4 -72.7(3)
O3 C10 C12 F5 165.8(2)
C11 C10 C12 F5 -71.1(3)
C13 C10 C12 F5 48.6(3)
O3 C10 C13 F8 47.8(3)
C11 C10 C13 F8 -74.9(2)
C12 C10 C13 F8 165.5(2)
O3 C10 C13 F7 -71.5(2)
C11 C10 C13 F7 165.8(2)
C12 C10 C13 F7 46.3(3)
O3 C10 C13 F9 168.7(2)
C11 C10 C13 F9 45.9(3)
C12 C10 C13 F9 -73.6(3)
W O4 C14 C17 -87.5(2)
W O4 C14 C15 34.9(3)
W O4 C14 C16 153.93(18)
O4 C14 C15 F10 37.0(2)
C17 C14 C15 F10 159.86(17)
C16 C14 C15 F10 -80.3(2)
O4 C14 C15 F12 157.79(17)
C17 C14 C15 F12 -79.3(2)
C16 C14 C15 F12 40.5(2)
O4 C14 C15 F11 -82.9(2)
C17 C14 C15 F11 40.0(2)
C16 C14 C15 F11 159.83(17)
O4 C14 C16 F14 -72.4(2)
C17 C14 C16 F14 169.14(17)
C15 C14 C16 F14 49.9(2)
O4 C14 C16 F15 46.5(2)
C17 C14 C16 F15 -72.0(2)
C15 C14 C16 F15 168.77(17)
O4 C14 C16 F13 166.39(17)
C17 C14 C16 F13 47.9(2)
C15 C14 C16 F13 -71.4(2)
O4 C14 C17 F17 52.6(2)
C15 C14 C17 F17 -72.6(2)
C16 C14 C17 F17 168.41(18)
O4 C14 C17 F18 173.40(18)
C15 C14 C17 F18 48.3(2)
C16 C14 C17 F18 -70.7(2)
O4 C14 C17 F16 -66.1(2)
C15 C14 C17 F16 168.81(17)
C16 C14 C17 F16 49.8(2)
