# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013
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#
# Cambridge Crystallographic Data Centre
# CCDC
#
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#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
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# fide research purposes only. It may contain copyright material
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data_orei33
_database_code_depnum_ccdc_archive 'CCDC 907721'
#TrackingRef 'orei33.cif'
_audit_update_record
;
2012-07-03 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C34 H29 F12 N O2 W'
_chemical_formula_weight 895.43
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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M P21/c
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'
_cell_length_a 10.6462(5)
_cell_length_b 15.7072(7)
_cell_length_c 19.9882(9)
_cell_angle_alpha 90.00
_cell_angle_beta 95.374(1)
_cell_angle_gamma 90.00
_cell_volume 3327.8(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9701
_cell_measurement_theta_min 2.32
_cell_measurement_theta_max 27.91
_exptl_crystal_description plates
_exptl_crystal_colour orange
_exptl_crystal_size_max 0.29
_exptl_crystal_size_mid 0.17
_exptl_crystal_size_min 0.05
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.787
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1752
_exptl_absorpt_coefficient_mu 3.571
_exptl_absorpt_correction_type numerical
_exptl_absorpt_correction_T_min 0.4230
_exptl_absorpt_correction_T_max 0.8388
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL v6.14 (Bruker 2008)'
_exptl_special_details ?
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator 'Bruker Triumph'
_diffrn_measurement_device_type 'Bruker APEX-II DUO'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 104900
_diffrn_reflns_av_R_equivalents 0.0372
_diffrn_reflns_av_sigmaI/netI 0.0154
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_theta_min 1.65
_diffrn_reflns_theta_max 27.50
_reflns_number_total 7644
_reflns_number_gt 6905
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'Bruker APEX2 (Bruker, 2008)'
_computing_cell_refinement 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT (Bruker, 2008)'
_computing_structure_solution 'Bruker SHELXTL (Bruker, 2008)'
_computing_structure_refinement 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
All H atoms were positioned geometrically ( C---H = 0.93/1.00 \%A) and allowed
to ride with U~iso~(H)= 1.2/1.5U~eq~(C).
Methyl ones were allowed to rotate around the corresponding C---C.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0228P)^2^+0.5601P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 7644
_refine_ls_number_parameters 457
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0178
_refine_ls_R_factor_gt 0.0145
_refine_ls_wR_factor_ref 0.0376
_refine_ls_wR_factor_gt 0.0369
_refine_ls_goodness_of_fit_ref 1.052
_refine_ls_restrained_S_all 1.052
_refine_ls_shift/su_max 0.005
_refine_ls_shift/su_mean 0.000
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
W1 W 0.867316(6) 0.059834(4) 0.789245(3) 0.01098(3) Uani 1 1 d . . .
F1 F 0.78316(12) -0.12082(7) 0.64411(6) 0.0318(3) Uani 1 1 d . . .
F2 F 0.83752(11) -0.20403(7) 0.72702(6) 0.0284(3) Uani 1 1 d . . .
F3 F 0.65121(12) -0.21350(7) 0.67661(6) 0.0355(3) Uani 1 1 d . . .
F4 F 0.68820(11) -0.20315(6) 0.82783(6) 0.0283(3) Uani 1 1 d . . .
F5 F 0.51131(11) -0.16251(7) 0.77700(6) 0.0323(3) Uani 1 1 d . . .
F6 F 0.60920(11) -0.08231(7) 0.85172(5) 0.0268(3) Uani 1 1 d . . .
F7 F 0.89037(11) 0.21896(7) 0.97820(5) 0.0245(2) Uani 1 1 d . . .
F8 F 1.01305(10) 0.27727(7) 0.91220(5) 0.0259(2) Uani 1 1 d . . .
F9 F 0.85345(11) 0.34668(6) 0.94124(5) 0.0253(2) Uani 1 1 d . . .
F10 F 0.90457(11) 0.33051(7) 0.79210(5) 0.0266(2) Uani 1 1 d . . .
F11 F 0.71951(10) 0.36032(6) 0.82055(5) 0.0231(2) Uani 1 1 d . . .
F12 F 0.74376(10) 0.26047(6) 0.74910(5) 0.0213(2) Uani 1 1 d . . .
O1 O 0.80666(12) -0.05696(7) 0.77930(6) 0.0152(2) Uani 1 1 d . . .
O2 O 0.88561(11) 0.16255(7) 0.84526(6) 0.0147(2) Uani 1 1 d . . .
N1 N 0.68349(14) 0.08608(8) 0.79566(7) 0.0128(3) Uani 1 1 d . . .
C1 C 0.69652(16) -0.09034(10) 0.74676(9) 0.0154(3) Uani 1 1 d . . .
C2 C 0.60949(16) -0.02348(11) 0.71090(8) 0.0134(3) Uani 1 1 d . . .
C3 C 0.60361(16) 0.05842(10) 0.73855(8) 0.0129(3) Uani 1 1 d . . .
C4 C 0.52015(16) 0.11781(10) 0.70621(8) 0.0142(3) Uani 1 1 d . . .
H4A H 0.5145 0.1732 0.7247 0.017 Uiso 1 1 calc R . .
C5 C 0.44631(16) 0.09741(11) 0.64818(8) 0.0149(3) Uani 1 1 d . . .
H5A H 0.3906 0.1389 0.6274 0.018 Uiso 1 1 calc R . .
C6 C 0.45210(16) 0.01662(11) 0.61945(8) 0.0152(3) Uani 1 1 d . . .
C7 C 0.53291(17) -0.04241(10) 0.65174(9) 0.0152(3) Uani 1 1 d . . .
H7A H 0.5367 -0.0979 0.6332 0.018 Uiso 1 1 calc R . .
C8 C 0.74233(19) -0.15814(11) 0.69805(10) 0.0231(4) Uani 1 1 d . . .
C9 C 0.62563(18) -0.13529(11) 0.8010(1) 0.0207(4) Uani 1 1 d . . .
C10 C 0.37130(18) -0.00542(11) 0.55562(9) 0.0204(4) Uani 1 1 d . . .
H10A H 0.4079 -0.0544 0.5340 0.031 Uiso 1 1 calc R . .
H10B H 0.3677 0.0435 0.5250 0.031 Uiso 1 1 calc R . .
H10C H 0.2859 -0.0196 0.5664 0.031 Uiso 1 1 calc R . .
C11 C 0.81166(17) 0.22933(10) 0.86331(8) 0.0146(3) Uani 1 1 d . . .
C12 C 0.68231(16) 0.19968(10) 0.88084(8) 0.0134(3) Uani 1 1 d . . .
C13 C 0.62419(16) 0.13086(10) 0.84558(8) 0.0126(3) Uani 1 1 d . . .
C14 C 0.50501(16) 0.10428(10) 0.86177(8) 0.0151(3) Uani 1 1 d . . .
H14A H 0.4648 0.0578 0.8381 0.018 Uiso 1 1 calc R . .
C15 C 0.44477(17) 0.14428(11) 0.91139(8) 0.0173(3) Uani 1 1 d . . .
H15A H 0.3639 0.1250 0.9213 0.021 Uiso 1 1 calc R . .
C16 C 0.50135(18) 0.21254(11) 0.94707(8) 0.0182(4) Uani 1 1 d . . .
C17 C 0.61884(17) 0.23928(11) 0.93088(8) 0.0170(4) Uani 1 1 d . . .
H17A H 0.6579 0.2862 0.9545 0.020 Uiso 1 1 calc R . .
C18 C 0.89243(18) 0.26901(11) 0.92406(9) 0.0197(4) Uani 1 1 d . . .
C19 C 0.79526(17) 0.29586(10) 0.80590(9) 0.0179(4) Uani 1 1 d . . .
C20 C 0.4356(2) 0.25693(13) 1.00104(10) 0.0282(4) Uani 1 1 d . . .
H20A H 0.4018 0.2144 1.0304 0.042 Uiso 1 1 calc R . .
H20B H 0.3664 0.2918 0.9801 0.042 Uiso 1 1 calc R . .
H20C H 0.4960 0.2934 1.0276 0.042 Uiso 1 1 calc R . .
C21 C 0.95097(16) 0.08299(11) 0.71107(8) 0.0153(3) Uani 1 1 d . . .
C22 C 1.05559(17) 0.05517(10) 0.75760(9) 0.0165(3) Uani 1 1 d . . .
C23 C 1.03247(16) 0.02676(10) 0.82561(8) 0.0149(3) Uani 1 1 d . . .
C24 C 0.94491(17) 0.11524(12) 0.63944(8) 0.0192(4) Uani 1 1 d . . .
C25 C 0.80509(18) 0.12453(13) 0.61426(9) 0.0236(4) Uani 1 1 d . . .
H25A H 0.7638 0.0688 0.6150 0.035 Uiso 1 1 calc R . .
H25B H 0.7976 0.1467 0.5682 0.035 Uiso 1 1 calc R . .
H25C H 0.7645 0.1640 0.6435 0.035 Uiso 1 1 calc R . .
C26 C 1.0067(2) 0.05156(14) 0.59467(10) 0.0348(5) Uani 1 1 d . . .
H26A H 0.9680 -0.0046 0.5987 0.052 Uiso 1 1 calc R . .
H26B H 1.0972 0.0479 0.6088 0.052 Uiso 1 1 calc R . .
H26C H 0.9944 0.0706 0.5478 0.052 Uiso 1 1 calc R . .
C27 C 1.0080(2) 0.20331(13) 0.63742(10) 0.0311(5) Uani 1 1 d . . .
H27A H 0.9695 0.2421 0.6681 0.047 Uiso 1 1 calc R . .
H27B H 0.9961 0.2260 0.5916 0.047 Uiso 1 1 calc R . .
H27C H 1.0983 0.1979 0.6513 0.047 Uiso 1 1 calc R . .
C28 C 1.19102(18) 0.06096(12) 0.74097(10) 0.0219(4) Uani 1 1 d . . .
H28A H 1.2160 0.0068 0.7218 0.033 Uiso 1 1 calc R . .
H28B H 1.2459 0.0731 0.7820 0.033 Uiso 1 1 calc R . .
H28C H 1.1989 0.1068 0.7083 0.033 Uiso 1 1 calc R . .
C29 C 1.12427(16) 0.00599(11) 0.88178(9) 0.0179(4) Uani 1 1 d . . .
C30 C 1.2231(2) -0.05203(11) 0.87643(11) 0.0259(4) Uani 1 1 d . . .
H30A H 1.2331 -0.0787 0.8346 0.031 Uiso 1 1 calc R . .
C31 C 1.3060(2) -0.07030(13) 0.93214(11) 0.0318(5) Uani 1 1 d . . .
H31A H 1.3727 -0.1097 0.9285 0.038 Uiso 1 1 calc R . .
C32 C 1.2921(2) -0.03143(14) 0.99309(11) 0.0323(5) Uani 1 1 d . . .
H32A H 1.3502 -0.0435 1.0309 0.039 Uiso 1 1 calc R . .
C33 C 1.1938(2) 0.02500(14) 0.99924(10) 0.0290(4) Uani 1 1 d . . .
H33A H 1.1839 0.0510 1.0413 0.035 Uiso 1 1 calc R . .
C34 C 1.10961(19) 0.04349(12) 0.94378(9) 0.0224(4) Uani 1 1 d . . .
H34A H 1.0418 0.0818 0.9481 0.027 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
W1 0.00886(4) 0.01295(4) 0.01103(4) -0.00068(2) 0.00047(2) -0.00042(2)
F1 0.0342(7) 0.0375(6) 0.0240(6) -0.0059(5) 0.0046(5) 0.0141(5)
F2 0.0241(6) 0.0232(5) 0.0361(6) -0.0069(5) -0.0068(5) 0.0118(5)
F3 0.0331(7) 0.0201(5) 0.0492(8) -0.0156(5) -0.0176(6) 0.0039(5)
F4 0.0253(6) 0.0200(5) 0.0391(7) 0.0129(5) 0.0000(5) 0.0036(5)
F5 0.0180(6) 0.0289(6) 0.0486(7) 0.0142(5) -0.0052(5) -0.0097(5)
F6 0.0309(7) 0.0247(5) 0.0263(6) 0.0064(4) 0.0096(5) 0.0015(5)
F7 0.0283(6) 0.0293(6) 0.0148(5) -0.0010(4) -0.0030(4) -0.0022(5)
F8 0.0185(6) 0.0310(6) 0.0278(6) -0.0097(5) -0.0002(5) -0.0081(5)
F9 0.0304(7) 0.0196(5) 0.0259(6) -0.0110(4) 0.0022(5) -0.0024(5)
F10 0.0208(6) 0.0286(6) 0.0314(6) 0.0078(5) 0.0072(5) -0.0066(5)
F11 0.0269(6) 0.0164(5) 0.0268(6) 0.0020(4) 0.0061(5) 0.0042(4)
F12 0.0274(6) 0.0221(5) 0.0142(5) 0.0016(4) 0.0008(4) -0.0009(4)
O1 0.0108(6) 0.0129(5) 0.0212(6) -0.0016(4) -0.0030(5) -0.0001(5)
O2 0.0120(6) 0.0156(5) 0.0163(6) -0.0031(5) 0.0009(5) -0.0008(5)
N1 0.0112(7) 0.0139(6) 0.0132(6) -0.0016(5) 0.0008(6) -0.0001(5)
C1 0.0128(9) 0.0125(7) 0.0202(8) -0.0010(7) -0.0022(7) 0.0005(6)
C2 0.0094(8) 0.0135(7) 0.0170(8) 0.0004(6) 0.0004(7) -0.0008(6)
C3 0.0107(8) 0.0153(7) 0.0129(7) -0.0002(6) 0.0026(6) -0.0021(6)
C4 0.0132(8) 0.0135(7) 0.0165(8) 0.0000(6) 0.0041(7) -0.0006(6)
C5 0.0125(8) 0.0178(8) 0.0146(8) 0.0047(6) 0.0020(7) 0.0013(7)
C6 0.0122(8) 0.0195(8) 0.0142(8) 0.0007(6) 0.0023(7) -0.0033(7)
C7 0.0141(9) 0.0148(7) 0.0167(8) -0.0022(6) 0.0012(7) -0.0021(6)
C8 0.0218(10) 0.0186(8) 0.0274(10) -0.0052(7) -0.0056(8) 0.0042(7)
C9 0.0157(9) 0.0156(8) 0.0298(10) 0.0062(7) -0.0027(8) -0.0008(7)
C10 0.0192(10) 0.0235(9) 0.0176(8) 0.0004(7) -0.0026(7) -0.0018(7)
C11 0.0162(9) 0.0144(7) 0.0132(8) -0.0016(6) 0.0008(7) -0.0017(6)
C12 0.0148(9) 0.0133(7) 0.0123(7) 0.0021(6) 0.0018(6) 0.0007(6)
C13 0.0132(8) 0.0132(7) 0.0114(7) 0.0022(6) 0.0017(6) 0.0029(6)
C14 0.0144(9) 0.0160(8) 0.0146(8) 0.0036(6) -0.0002(7) 0.0011(7)
C15 0.0141(9) 0.0200(8) 0.0183(8) 0.0071(7) 0.0051(7) 0.0032(7)
C16 0.0212(10) 0.0190(8) 0.0152(8) 0.0035(7) 0.0058(7) 0.0062(7)
C17 0.0214(10) 0.0152(8) 0.0143(8) -0.0001(6) 0.0020(7) 0.0024(7)
C18 0.0209(10) 0.0186(8) 0.0196(9) -0.0050(7) 0.0019(8) -0.0024(7)
C19 0.0172(9) 0.0167(8) 0.0203(8) 0.0001(7) 0.0046(7) -0.0029(7)
C20 0.0325(12) 0.0296(10) 0.0246(10) -0.0034(8) 0.0133(9) 0.0043(9)
C21 0.0123(8) 0.0188(8) 0.0150(8) -0.0030(6) 0.0026(7) -0.0017(7)
C22 0.0126(9) 0.0178(8) 0.0194(8) -0.0040(7) 0.0031(7) -0.0010(7)
C23 0.0126(9) 0.0145(7) 0.0174(8) -0.0009(6) 0.0003(7) -0.0001(6)
C24 0.0163(9) 0.0293(9) 0.0123(8) 0.0007(7) 0.0022(7) -0.0022(7)
C25 0.0191(10) 0.0366(10) 0.0146(8) 0.0041(8) -0.0001(7) -0.0018(8)
C26 0.0324(13) 0.0550(14) 0.0179(9) -0.0043(9) 0.0074(9) 0.010(1)
C27 0.0294(12) 0.0405(11) 0.0222(9) 0.0107(9) -0.0033(9) -0.0129(9)
C28 0.0114(9) 0.0298(10) 0.0249(9) 0.0013(8) 0.0039(7) 0.0008(7)
C29 0.0120(9) 0.0200(8) 0.0213(9) 0.0053(7) -0.0012(7) -0.0030(7)
C30 0.0222(11) 0.0248(9) 0.030(1) 0.0035(8) -0.0011(8) 0.0043(8)
C31 0.0215(11) 0.0311(11) 0.0419(12) 0.0142(9) -0.0024(9) 0.0069(8)
C32 0.0216(11) 0.0434(12) 0.0302(11) 0.0217(10) -0.0072(9) -0.0060(9)
C33 0.0244(11) 0.0422(11) 0.0197(9) 0.0091(9) -0.0013(8) -0.0065(9)
C34 0.0175(10) 0.0287(9) 0.0211(9) 0.0067(7) 0.0017(8) -0.0012(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
W1 C21 1.9046(16) . ?
W1 C23 1.9106(18) . ?
W1 O1 1.9489(11) . ?
W1 O2 1.9631(11) . ?
W1 N1 2.0158(14) . ?
W1 C22 2.1589(18) . ?
F1 C8 1.335(2) . ?
F2 C8 1.331(2) . ?
F3 C8 1.343(2) . ?
F4 C9 1.342(2) . ?
F5 C9 1.336(2) . ?
F6 C9 1.336(2) . ?
F7 C18 1.339(2) . ?
F8 C18 1.334(2) . ?
F9 C18 1.3435(19) . ?
F10 C19 1.337(2) . ?
F11 C19 1.3436(19) . ?
F12 C19 1.335(2) . ?
O1 C1 1.389(2) . ?
O2 C11 1.3797(19) . ?
N1 C13 1.417(2) . ?
N1 C3 1.426(2) . ?
C1 C2 1.533(2) . ?
C1 C9 1.548(2) . ?
C1 C8 1.552(2) . ?
C2 C3 1.404(2) . ?
C2 C7 1.404(2) . ?
C3 C4 1.404(2) . ?
C4 C5 1.377(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.397(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.383(2) . ?
C6 C10 1.511(2) . ?
C7 H7A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.525(2) . ?
C11 C19 1.550(2) . ?
C11 C18 1.551(2) . ?
C12 C13 1.402(2) . ?
C12 C17 1.404(2) . ?
C13 C14 1.402(2) . ?
C14 C15 1.382(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.393(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.386(2) . ?
C16 C20 1.510(2) . ?
C17 H17A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.450(3) . ?
C21 C24 1.514(2) . ?
C22 C23 1.473(2) . ?
C22 C28 1.512(2) . ?
C23 C29 1.455(2) . ?
C24 C26 1.531(3) . ?
C24 C25 1.533(3) . ?
C24 C27 1.540(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C34 1.394(3) . ?
C29 C30 1.403(3) . ?
C30 C31 1.385(3) . ?
C30 H30A 0.9500 . ?
C31 C32 1.383(3) . ?
C31 H31A 0.9500 . ?
C32 C33 1.386(3) . ?
C32 H32A 0.9500 . ?
C33 C34 1.389(3) . ?
C33 H33A 0.9500 . ?
C34 H34A 0.9500 . ?
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
C21 W1 C23 83.09(7) . . ?
C21 W1 O1 105.78(6) . . ?
C23 W1 O1 93.85(6) . . ?
C21 W1 O2 106.38(6) . . ?
C23 W1 O2 88.16(6) . . ?
O1 W1 O2 147.78(5) . . ?
C21 W1 N1 122.99(7) . . ?
C23 W1 N1 153.60(6) . . ?
O1 W1 N1 83.38(5) . . ?
O2 W1 N1 80.83(5) . . ?
C21 W1 C22 41.22(7) . . ?
C23 W1 C22 41.90(7) . . ?
O1 W1 C22 104.24(6) . . ?
O2 W1 C22 98.61(6) . . ?
N1 W1 C22 163.57(6) . . ?
C1 O1 W1 131.31(10) . . ?
C11 O2 W1 138.19(11) . . ?
C13 N1 C3 116.32(14) . . ?
C13 N1 W1 130.22(11) . . ?
C3 N1 W1 113.36(10) . . ?
O1 C1 C2 114.02(13) . . ?
O1 C1 C9 106.85(14) . . ?
C2 C1 C9 109.08(14) . . ?
O1 C1 C8 104.57(14) . . ?
C2 C1 C8 112.85(14) . . ?
C9 C1 C8 109.19(14) . . ?
C3 C2 C7 118.82(15) . . ?
C3 C2 C1 119.39(15) . . ?
C7 C2 C1 121.78(15) . . ?
C4 C3 C2 118.50(15) . . ?
C4 C3 N1 118.07(14) . . ?
C2 C3 N1 123.32(15) . . ?
C5 C4 C3 121.35(15) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C5 C6 120.94(16) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C7 C6 C5 117.82(16) . . ?
C7 C6 C10 121.38(15) . . ?
C5 C6 C10 120.79(15) . . ?
C6 C7 C2 122.54(15) . . ?
C6 C7 H7A 118.7 . . ?
C2 C7 H7A 118.7 . . ?
F2 C8 F1 107.27(15) . . ?
F2 C8 F3 106.62(14) . . ?
F1 C8 F3 107.86(15) . . ?
F2 C8 C1 111.70(15) . . ?
F1 C8 C1 110.52(14) . . ?
F3 C8 C1 112.62(16) . . ?
F6 C9 F5 106.99(15) . . ?
F6 C9 F4 106.68(15) . . ?
F5 C9 F4 106.91(14) . . ?
F6 C9 C1 110.76(13) . . ?
F5 C9 C1 112.46(15) . . ?
F4 C9 C1 112.69(15) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C12 112.18(13) . . ?
O2 C11 C19 110.28(13) . . ?
C12 C11 C19 109.54(14) . . ?
O2 C11 C18 102.83(14) . . ?
C12 C11 C18 112.89(13) . . ?
C19 C11 C18 108.93(13) . . ?
C13 C12 C17 118.71(15) . . ?
C13 C12 C11 119.03(14) . . ?
C17 C12 C11 122.26(15) . . ?
C14 C13 C12 118.67(15) . . ?
C14 C13 N1 119.17(15) . . ?
C12 C13 N1 122.14(15) . . ?
C15 C14 C13 121.41(16) . . ?
C15 C14 H14A 119.3 . . ?
C13 C14 H14A 119.3 . . ?
C14 C15 C16 120.66(16) . . ?
C14 C15 H15A 119.7 . . ?
C16 C15 H15A 119.7 . . ?
C17 C16 C15 118.04(15) . . ?
C17 C16 C20 121.02(17) . . ?
C15 C16 C20 120.93(17) . . ?
C16 C17 C12 122.50(16) . . ?
C16 C17 H17A 118.8 . . ?
C12 C17 H17A 118.8 . . ?
F8 C18 F7 106.83(15) . . ?
F8 C18 F9 106.42(14) . . ?
F7 C18 F9 107.32(13) . . ?
F8 C18 C11 111.85(14) . . ?
F7 C18 C11 110.29(14) . . ?
F9 C18 C11 113.77(15) . . ?
F12 C19 F10 106.87(13) . . ?
F12 C19 F11 106.97(15) . . ?
F10 C19 F11 106.87(13) . . ?
F12 C19 C11 110.96(13) . . ?
F10 C19 C11 112.80(15) . . ?
F11 C19 C11 112.03(13) . . ?
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 . . ?
C22 C21 C24 132.01(15) . . ?
C22 C21 W1 78.84(10) . . ?
C24 C21 W1 149.07(14) . . ?
C21 C22 C23 119.89(15) . . ?
C21 C22 C28 122.13(16) . . ?
C23 C22 C28 117.78(16) . . ?
C21 C22 W1 59.94(9) . . ?
C23 C22 W1 60.00(9) . . ?
C28 C22 W1 173.09(13) . . ?
C29 C23 C22 128.45(16) . . ?
C29 C23 W1 151.93(13) . . ?
C22 C23 W1 78.11(10) . . ?
C21 C24 C26 110.58(15) . . ?
C21 C24 C25 107.23(14) . . ?
C26 C24 C25 109.11(16) . . ?
C21 C24 C27 110.19(15) . . ?
C26 C24 C27 111.07(16) . . ?
C25 C24 C27 108.54(16) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 C28 H28A 109.5 . . ?
C22 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C22 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C34 C29 C30 119.30(17) . . ?
C34 C29 C23 117.92(16) . . ?
C30 C29 C23 122.75(17) . . ?
C31 C30 C29 119.94(19) . . ?
C31 C30 H30A 120.0 . . ?
C29 C30 H30A 120.0 . . ?
C32 C31 C30 120.3(2) . . ?
C32 C31 H31A 119.9 . . ?
C30 C31 H31A 119.9 . . ?
C31 C32 C33 120.31(19) . . ?
C31 C32 H32A 119.8 . . ?
C33 C32 H32A 119.8 . . ?
C32 C33 C34 119.92(19) . . ?
C32 C33 H33A 120.0 . . ?
C34 C33 H33A 120.0 . . ?
C33 C34 C29 120.24(18) . . ?
C33 C34 H34A 119.9 . . ?
C29 C34 H34A 119.9 . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.827
_refine_diff_density_min -0.431
_refine_diff_density_rms 0.066
data_orei34
_database_code_depnum_ccdc_archive 'CCDC 907722'
#TrackingRef 'orei34.cif'
_vrf_PLAT770_I
;
PROBLEM: Suspect C-H Bond in CIF: C31 -- H32C .. 1.43 Ang.
RESPONSE: C30-31 and C30'-C31' along with their protons and those on adjacent C atoms,
are two parts of a disorder. C31 and h32c belong to different parts of the disorder.
;
_audit_update_record
;
2012-07-03 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C33 H33 F12 N O2 W'
_chemical_formula_weight 887.45
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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M P21/c
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'
_cell_length_a 19.6072(11)
_cell_length_b 9.2537(5)
_cell_length_c 18.9077(10)
_cell_angle_alpha 90.00
_cell_angle_beta 112.5630(10)
_cell_angle_gamma 90.00
_cell_volume 3168.0(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9884
_cell_measurement_theta_min 2.25
_cell_measurement_theta_max 31.49
_exptl_crystal_description plates
_exptl_crystal_colour orange
_exptl_crystal_size_max 0.16
_exptl_crystal_size_mid 0.13
_exptl_crystal_size_min 0.01
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.861
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1744
_exptl_absorpt_coefficient_mu 3.750
_exptl_absorpt_correction_type numerical
_exptl_absorpt_correction_T_min 0.5941
_exptl_absorpt_correction_T_max 0.9529
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL v6.14 (Bruker 2008)'
_exptl_special_details ?
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator 'Bruker Triumph'
_diffrn_measurement_device_type 'Bruker APEX-II DUO'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_decay_% 0
_diffrn_reflns_number 52389
_diffrn_reflns_av_R_equivalents 0.0410
_diffrn_reflns_av_sigmaI/netI 0.0305
_diffrn_reflns_limit_h_min -25
_diffrn_reflns_limit_h_max 25
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_theta_min 2.17
_diffrn_reflns_theta_max 27.50
_reflns_number_total 7274
_reflns_number_gt 6082
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'Bruker APEX2 (Bruker, 2008)'
_computing_cell_refinement 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT (Bruker, 2008)'
_computing_structure_solution 'Bruker SHELXTL (Bruker, 2008)'
_computing_structure_refinement 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
All H atoms were positioned geometrically ( C---H = 0.93/1.00 \%A) and allowed
to ride with U~iso~(H)= 1.2/1.5U~eq~(C).
Methyl ones were allowed to rotate around the corresponding C---C.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0261P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 7274
_refine_ls_number_parameters 446
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0297
_refine_ls_R_factor_gt 0.0209
_refine_ls_wR_factor_ref 0.0462
_refine_ls_wR_factor_gt 0.0448
_refine_ls_goodness_of_fit_ref 0.962
_refine_ls_restrained_S_all 0.962
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
W1 W 0.247806(6) 0.077468(10) 0.271440(6) 0.01267(3) Uani 1 1 d . . .
F1 F 0.08263(9) -0.22230(17) 0.19915(9) 0.0259(4) Uani 1 1 d . . .
F2 F 0.01460(9) -0.04228(17) 0.20115(10) 0.0266(4) Uani 1 1 d . . .
F3 F 0.02101(8) -0.22594(17) 0.27334(9) 0.0254(4) Uani 1 1 d . . .
F4 F 0.03881(9) 0.06890(17) 0.33855(9) 0.0270(4) Uani 1 1 d . . .
F5 F 0.09206(9) -0.10273(16) 0.41642(9) 0.0260(4) Uani 1 1 d . . .
F6 F 0.15212(9) 0.08997(16) 0.41417(9) 0.0260(4) Uani 1 1 d . . .
F7 F 0.39970(9) 0.45132(15) 0.38261(9) 0.0210(3) Uani 1 1 d . . .
F8 F 0.43972(8) 0.35938(16) 0.30159(8) 0.0194(3) Uani 1 1 d . . .
F9 F 0.50884(8) 0.35765(16) 0.42138(9) 0.0213(3) Uani 1 1 d . . .
F10 F 0.47736(9) 0.07767(16) 0.31828(9) 0.0238(3) Uani 1 1 d . . .
F11 F 0.51874(8) 0.07416(16) 0.44152(9) 0.0203(3) Uani 1 1 d . . .
F12 F 0.42570(8) -0.05774(14) 0.37539(9) 0.0198(3) Uani 1 1 d . . .
O1 O 0.14992(9) 0.03973(18) 0.27335(10) 0.0158(4) Uani 1 1 d . . .
O2 O 0.34002(9) 0.18949(17) 0.31168(10) 0.0135(4) Uani 1 1 d . . .
N1 N 0.28329(11) 0.0166(2) 0.38255(12) 0.0126(4) Uani 1 1 d . . .
C1 C 0.12813(14) -0.0717(3) 0.30937(15) 0.0160(5) Uani 1 1 d . . .
C2 C 0.18982(14) -0.1802(3) 0.35087(15) 0.0150(5) Uani 1 1 d . . .
C3 C 0.26171(14) -0.1283(3) 0.39069(14) 0.0128(5) Uani 1 1 d . . .
C4 C 0.31601(14) -0.2263(3) 0.43492(15) 0.0170(5) Uani 1 1 d . . .
H4A H 0.3643 -0.1922 0.4644 0.020 Uiso 1 1 calc R . .
C5 C 0.30022(15) -0.3715(3) 0.43617(15) 0.0172(6) Uani 1 1 d . . .
H5A H 0.3376 -0.4353 0.4674 0.021 Uiso 1 1 calc R . .
C6 C 0.23064(15) -0.4261(3) 0.39257(16) 0.0194(5) Uani 1 1 d . . .
C7 C 0.17576(15) -0.3286(3) 0.35247(16) 0.0184(6) Uani 1 1 d . . .
H7A H 0.1271 -0.3633 0.3252 0.022 Uiso 1 1 calc R . .
C8 C 0.06084(15) -0.1416(3) 0.24524(16) 0.0205(6) Uani 1 1 d . . .
C9 C 0.10205(14) -0.0031(3) 0.36993(16) 0.0179(6) Uani 1 1 d . . .
C10 C 0.21606(17) -0.5868(3) 0.38531(18) 0.0268(6) Uani 1 1 d . . .
H10A H 0.1628 -0.6043 0.3681 0.040 Uiso 1 1 calc R . .
H10B H 0.2416 -0.6330 0.4352 0.040 Uiso 1 1 calc R . .
H10C H 0.2343 -0.6273 0.3480 0.040 Uiso 1 1 calc R . .
C11 C 0.40302(13) 0.1943(2) 0.37770(14) 0.0119(5) Uani 1 1 d . . .
C12 C 0.38632(13) 0.1823(2) 0.45028(14) 0.0122(5) Uani 1 1 d . . .
C13 C 0.32904(14) 0.0903(3) 0.44961(14) 0.0132(5) Uani 1 1 d . . .
C14 C 0.31685(14) 0.0747(3) 0.51783(15) 0.0167(5) Uani 1 1 d . . .
H14A H 0.2782 0.0135 0.5183 0.020 Uiso 1 1 calc R . .
C15 C 0.35973(15) 0.1462(3) 0.58395(15) 0.0182(6) Uani 1 1 d . . .
H15A H 0.3502 0.1328 0.6292 0.022 Uiso 1 1 calc R . .
C16 C 0.41666(15) 0.2375(3) 0.58558(15) 0.0180(5) Uani 1 1 d . . .
C17 C 0.42874(14) 0.2537(3) 0.51809(14) 0.0157(5) Uani 1 1 d . . .
H17A H 0.4674 0.3158 0.5181 0.019 Uiso 1 1 calc R . .
C18 C 0.43871(14) 0.3415(3) 0.37136(15) 0.0158(5) Uani 1 1 d . . .
C19 C 0.45721(14) 0.0713(3) 0.37858(14) 0.0150(5) Uani 1 1 d . . .
C20 C 0.46593(18) 0.3116(3) 0.65839(16) 0.0287(7) Uani 1 1 d . . .
H20A H 0.4805 0.2423 0.7008 0.043 Uiso 1 1 calc R . .
H20B H 0.4392 0.3921 0.6695 0.043 Uiso 1 1 calc R . .
H20C H 0.5101 0.3484 0.6521 0.043 Uiso 1 1 calc R . .
C21 C 0.25296(15) -0.0436(3) 0.19177(15) 0.0176(6) Uani 1 1 d . . .
C22 C 0.22203(14) 0.0869(3) 0.14997(15) 0.0186(5) Uani 1 1 d . . .
C23 C 0.20919(14) 0.2132(3) 0.19065(15) 0.0180(6) Uani 1 1 d . . .
C24 C 0.27815(16) -0.1836(3) 0.16781(16) 0.0215(6) Uani 1 1 d . . .
C25 C 0.21675(17) -0.2544(3) 0.09918(17) 0.0304(7) Uani 1 1 d . . .
H25A H 0.2060 -0.1941 0.0536 0.046 Uiso 1 1 calc R . .
H25B H 0.1721 -0.2642 0.1103 0.046 Uiso 1 1 calc R . .
H25C H 0.2330 -0.3502 0.0899 0.046 Uiso 1 1 calc R . .
C26 C 0.34643(16) -0.1553(3) 0.14883(18) 0.0294(7) Uani 1 1 d . . .
H26A H 0.3867 -0.1187 0.1945 0.044 Uiso 1 1 calc R . .
H26B H 0.3343 -0.0836 0.1077 0.044 Uiso 1 1 calc R . .
H26C H 0.3618 -0.2456 0.1322 0.044 Uiso 1 1 calc R . .
C27 C 0.29984(17) -0.2871(3) 0.23602(16) 0.0262(7) Uani 1 1 d . . .
H27A H 0.3383 -0.2425 0.2805 0.039 Uiso 1 1 calc R . .
H27B H 0.3187 -0.3773 0.2232 0.039 Uiso 1 1 calc R . .
H27C H 0.2565 -0.3079 0.2481 0.039 Uiso 1 1 calc R . .
C28 C 0.19839(16) 0.1014(3) 0.06394(16) 0.0284(7) Uani 1 1 d . A .
H28A H 0.2272 0.0332 0.0460 0.034 Uiso 1 1 calc R . .
H28B H 0.2091 0.2006 0.0515 0.034 Uiso 1 1 calc R . .
C29 C 0.11484(18) 0.0698(4) 0.02153(19) 0.0410(8) Uani 1 1 d . . .
H29A H 0.1065 -0.0350 0.0251 0.049 Uiso 0.628(6) 1 calc PR A 1
H29B H 0.1005 0.0935 -0.0333 0.049 Uiso 0.628(6) 1 calc PR A 1
H29C H 0.1078 0.0291 -0.0292 0.049 Uiso 0.372(6) 1 d PR A 2
H29D H 0.1015 -0.0070 0.0504 0.049 Uiso 0.372(6) 1 d PR A 2
C30 C 0.0600(3) 0.1599(6) 0.0545(3) 0.0292(13) Uiso 0.628(6) 1 d P A 1
H30A H 0.0084 0.1298 0.0250 0.035 Uiso 0.628(6) 1 calc PR A 1
H30B H 0.0724 0.1316 0.1085 0.035 Uiso 0.628(6) 1 calc PR A 1
C31 C 0.0644(3) 0.3253(5) 0.0506(3) 0.0296(14) Uiso 0.628(6) 1 d P A 1
H31A H 0.0918 0.3528 0.0182 0.036 Uiso 0.628(6) 1 calc PR A 1
H31B H 0.0140 0.3663 0.0274 0.036 Uiso 0.628(6) 1 calc PR A 1
C30' C 0.0664(5) 0.1767(9) 0.0101(5) 0.030(2) Uiso 0.372(6) 1 d P A 2
H30C H 0.0191 0.1487 -0.0310 0.036 Uiso 0.372(6) 1 calc PR A 2
H30D H 0.0850 0.2638 -0.0072 0.036 Uiso 0.372(6) 1 calc PR A 2
C31' C 0.0532(4) 0.2126(9) 0.0823(5) 0.024(2) Uiso 0.372(6) 1 d P A 2
H31C H 0.0711 0.1320 0.1193 0.028 Uiso 0.372(6) 1 calc PR A 2
H31D H -0.0005 0.2238 0.0693 0.028 Uiso 0.372(6) 1 calc PR A 2
C32 C 0.1017(2) 0.3825(5) 0.1272(2) 0.0528(11) Uani 1 1 d . . .
H32A H 0.0817 0.3346 0.1621 0.063 Uiso 0.628(6) 1 calc PR A 1
H32B H 0.0909 0.4871 0.1268 0.063 Uiso 0.628(6) 1 calc PR A 1
H32C H 0.0876 0.4611 0.0888 0.063 Uiso 0.372(6) 1 d PR A 2
H32D H 0.0865 0.4111 0.1695 0.063 Uiso 0.372(6) 1 d PR A 2
C33 C 0.18549(17) 0.3609(3) 0.15847(19) 0.0328(8) Uani 1 1 d . A .
H33A H 0.2032 0.3783 0.1167 0.039 Uiso 1 1 calc R . .
H33B H 0.2091 0.4334 0.1990 0.039 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
W1 0.01532(5) 0.01094(5) 0.01158(5) 0.00111(5) 0.00496(4) -0.00113(4)
F1 0.0290(9) 0.0257(9) 0.0228(9) -0.0082(7) 0.0098(8) -0.0058(7)
F2 0.0190(8) 0.0262(9) 0.0274(9) 0.0033(7) 0.0011(7) -0.0009(7)
F3 0.0219(8) 0.0225(8) 0.0323(10) -0.0009(7) 0.0111(8) -0.0080(7)
F4 0.0228(8) 0.0283(9) 0.0309(9) 0.0039(8) 0.0114(8) 0.0119(7)
F5 0.0340(9) 0.0231(9) 0.0296(9) 0.0071(7) 0.0219(8) 0.0049(7)
F6 0.0250(8) 0.0237(9) 0.0313(9) -0.0121(7) 0.0131(8) -0.0035(7)
F7 0.0308(9) 0.0116(8) 0.0263(9) 0.0009(6) 0.0171(8) 0.0007(6)
F8 0.0289(9) 0.0174(7) 0.0162(8) -0.0001(6) 0.0136(7) -0.0060(7)
F9 0.0197(8) 0.0204(8) 0.0208(8) -0.0014(7) 0.0047(7) -0.0080(6)
F10 0.0345(9) 0.0252(8) 0.0199(8) 0.0035(7) 0.0194(8) 0.0082(7)
F11 0.0177(8) 0.0213(8) 0.0198(8) 0.0004(7) 0.0047(7) 0.0032(7)
F12 0.0238(8) 0.0100(7) 0.0279(9) -0.0020(6) 0.0125(7) 0.0002(6)
O1 0.0159(9) 0.0140(9) 0.0177(10) 0.0054(7) 0.0065(8) 0.0002(7)
O2 0.0162(9) 0.0138(9) 0.0102(9) 0.0006(7) 0.0047(8) -0.0027(7)
N1 0.0172(11) 0.0095(10) 0.0110(11) 0.0019(8) 0.0054(9) -0.0018(8)
C1 0.0174(12) 0.0116(12) 0.0195(13) -0.0007(11) 0.0077(11) -0.0024(10)
C2 0.0182(13) 0.0128(12) 0.0172(14) 0.0024(10) 0.0103(12) 0.0019(10)
C3 0.0177(13) 0.0106(11) 0.0125(13) 0.0004(10) 0.0087(11) 0.0009(10)
C4 0.0171(13) 0.0198(13) 0.0159(13) 0.0029(11) 0.0084(11) 0.0037(11)
C5 0.0249(15) 0.0141(12) 0.0172(14) 0.0049(11) 0.0132(12) 0.0082(11)
C6 0.0302(15) 0.0115(12) 0.0235(14) 0.0013(12) 0.0181(13) 0.0011(12)
C7 0.0222(14) 0.0138(13) 0.0231(15) -0.0012(11) 0.0129(13) -0.0013(11)
C8 0.0186(14) 0.0181(13) 0.0241(15) 0.0016(12) 0.0074(12) -0.0020(11)
C9 0.0178(14) 0.0150(14) 0.0222(15) 0.0022(11) 0.0091(12) 0.0025(10)
C10 0.0399(17) 0.0125(13) 0.0348(17) 0.0012(13) 0.0218(15) 0.0012(13)
C11 0.0134(12) 0.0105(12) 0.0115(12) -0.0009(10) 0.0047(11) -0.0005(9)
C12 0.0155(12) 0.0090(11) 0.0125(13) 0.0004(10) 0.0057(11) 0.0032(9)
C13 0.0162(12) 0.0105(12) 0.0131(12) 0.0019(10) 0.0057(10) 0.0041(10)
C14 0.0185(13) 0.0164(12) 0.0182(13) 0.0042(12) 0.0105(11) 0.0036(11)
C15 0.0267(15) 0.0178(13) 0.0139(13) 0.0034(11) 0.0119(12) 0.0054(11)
C16 0.0297(15) 0.0109(12) 0.0139(13) -0.0009(10) 0.0089(12) 0.0044(11)
C17 0.0230(14) 0.0082(12) 0.0156(13) 0.0009(10) 0.0071(11) 0.0013(10)
C18 0.0198(14) 0.0144(13) 0.0141(13) 0.0005(10) 0.0076(12) -0.0023(10)
C19 0.0188(13) 0.0144(12) 0.0142(12) 0.0007(11) 0.0090(11) -0.0008(11)
C20 0.050(2) 0.0197(15) 0.0162(15) -0.0040(12) 0.0121(15) -0.0048(13)
C21 0.0206(14) 0.0193(14) 0.0145(13) -0.0028(11) 0.0085(11) -0.0061(11)
C22 0.0169(13) 0.0246(14) 0.0126(13) 0.0038(12) 0.0036(11) -0.0067(11)
C23 0.0152(13) 0.0197(13) 0.0183(14) 0.0043(11) 0.0055(12) -0.0024(10)
C24 0.0258(15) 0.0218(14) 0.0190(15) -0.0067(12) 0.0110(13) -0.0032(11)
C25 0.0347(17) 0.0302(17) 0.0283(17) -0.0140(14) 0.0142(15) -0.0091(14)
C26 0.0295(17) 0.0360(18) 0.0263(17) -0.0058(14) 0.0149(14) -0.0040(14)
C27 0.0371(17) 0.0195(14) 0.0275(16) -0.0057(12) 0.0186(15) -0.0023(12)
C28 0.0279(16) 0.0397(19) 0.0142(14) 0.0038(13) 0.0043(13) -0.0102(13)
C29 0.0316(18) 0.056(2) 0.0226(17) 0.0038(16) -0.0040(14) -0.0159(17)
C32 0.040(2) 0.087(3) 0.031(2) 0.0104(19) 0.0136(18) 0.037(2)
C33 0.0383(19) 0.0302(16) 0.0387(19) 0.0204(15) 0.0243(17) 0.0119(14)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
W1 C23 1.897(3) . ?
W1 C21 1.911(3) . ?
W1 O1 1.9648(17) . ?
W1 O2 1.9664(16) . ?
W1 N1 2.023(2) . ?
W1 C22 2.156(3) . ?
F1 C8 1.336(3) . ?
F2 C8 1.335(3) . ?
F3 C8 1.349(3) . ?
F4 C9 1.330(3) . ?
F5 C9 1.339(3) . ?
F6 C9 1.332(3) . ?
F7 C18 1.337(3) . ?
F8 C18 1.337(3) . ?
F9 C18 1.345(3) . ?
F10 C19 1.343(3) . ?
F11 C19 1.331(3) . ?
F12 C19 1.335(3) . ?
O1 C1 1.390(3) . ?
O2 C11 1.379(3) . ?
N1 C13 1.416(3) . ?
N1 C3 1.432(3) . ?
C1 C2 1.536(4) . ?
C1 C8 1.550(4) . ?
C1 C9 1.558(3) . ?
C2 C7 1.403(3) . ?
C2 C3 1.403(3) . ?
C3 C4 1.404(3) . ?
C4 C5 1.381(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.390(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.386(4) . ?
C6 C10 1.511(4) . ?
C7 H7A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.532(3) . ?
C11 C19 1.553(3) . ?
C11 C18 1.557(3) . ?
C12 C17 1.398(3) . ?
C12 C13 1.405(3) . ?
C13 C14 1.406(3) . ?
C14 C15 1.379(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.391(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.392(3) . ?
C16 C20 1.509(4) . ?
C17 H17A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.443(4) . ?
C21 C24 1.516(4) . ?
C22 C23 1.473(4) . ?
C22 C28 1.517(4) . ?
C23 C33 1.496(4) . ?
C24 C27 1.530(4) . ?
C24 C26 1.536(4) . ?
C24 C25 1.538(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.550(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30' 1.330(9) . ?
C29 C30 1.659(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 H29C 0.9900 . ?
C29 H29D 0.9900 . ?
C30 C31 1.536(7) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.449(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 H32C 1.4334 . ?
C30' C31' 1.521(12) . ?
C30' H30C 0.9900 . ?
C30' H30D 0.9900 . ?
C31' C32 1.865(9) . ?
C31' H31C 0.9900 . ?
C31' H31D 0.9900 . ?
C32 C33 1.531(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 H32C 0.9900 . ?
C32 H32D 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
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
C23 W1 C21 83.04(11) . . ?
C23 W1 O1 92.39(9) . . ?
C21 W1 O1 104.95(9) . . ?
C23 W1 O2 89.20(9) . . ?
C21 W1 O2 107.16(9) . . ?
O1 W1 O2 147.80(7) . . ?
C23 W1 N1 153.22(10) . . ?
C21 W1 N1 123.66(10) . . ?
O1 W1 N1 83.14(8) . . ?
O2 W1 N1 81.16(7) . . ?
C23 W1 C22 42.03(11) . . ?
C21 W1 C22 41.01(10) . . ?
O1 W1 C22 101.27(9) . . ?
O2 W1 C22 101.29(8) . . ?
N1 W1 C22 164.62(9) . . ?
C1 O1 W1 128.81(15) . . ?
C11 O2 W1 137.59(14) . . ?
C13 N1 C3 117.82(19) . . ?
C13 N1 W1 130.02(15) . . ?
C3 N1 W1 111.98(15) . . ?
O1 C1 C2 113.9(2) . . ?
O1 C1 C8 104.8(2) . . ?
C2 C1 C8 113.2(2) . . ?
O1 C1 C9 107.9(2) . . ?
C2 C1 C9 107.9(2) . . ?
C8 C1 C9 108.9(2) . . ?
C7 C2 C3 119.2(2) . . ?
C7 C2 C1 121.9(2) . . ?
C3 C2 C1 118.8(2) . . ?
C2 C3 C4 118.3(2) . . ?
C2 C3 N1 122.7(2) . . ?
C4 C3 N1 118.7(2) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C7 C6 C5 117.9(2) . . ?
C7 C6 C10 120.7(3) . . ?
C5 C6 C10 121.3(2) . . ?
C6 C7 C2 122.1(3) . . ?
C6 C7 H7A 119.0 . . ?
C2 C7 H7A 119.0 . . ?
F2 C8 F1 106.7(2) . . ?
F2 C8 F3 106.7(2) . . ?
F1 C8 F3 108.2(2) . . ?
F2 C8 C1 111.8(2) . . ?
F1 C8 C1 110.7(2) . . ?
F3 C8 C1 112.4(2) . . ?
F4 C9 F6 107.0(2) . . ?
F4 C9 F5 106.9(2) . . ?
F6 C9 F5 106.9(2) . . ?
F4 C9 C1 112.9(2) . . ?
F6 C9 C1 110.8(2) . . ?
F5 C9 C1 111.9(2) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C12 112.54(19) . . ?
O2 C11 C19 110.95(19) . . ?
C12 C11 C19 108.54(19) . . ?
O2 C11 C18 103.38(19) . . ?
C12 C11 C18 112.90(19) . . ?
C19 C11 C18 108.41(19) . . ?
C17 C12 C13 119.1(2) . . ?
C17 C12 C11 122.1(2) . . ?
C13 C12 C11 118.7(2) . . ?
C12 C13 C14 118.1(2) . . ?
C12 C13 N1 122.0(2) . . ?
C14 C13 N1 120.0(2) . . ?
C15 C14 C13 121.6(2) . . ?
C15 C14 H14A 119.2 . . ?
C13 C14 H14A 119.2 . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15A 119.5 . . ?
C16 C15 H15A 119.5 . . ?
C15 C16 C17 117.5(2) . . ?
C15 C16 C20 121.6(2) . . ?
C17 C16 C20 120.8(2) . . ?
C16 C17 C12 122.6(2) . . ?
C16 C17 H17A 118.7 . . ?
C12 C17 H17A 118.7 . . ?
F8 C18 F7 106.8(2) . . ?
F8 C18 F9 106.37(19) . . ?
F7 C18 F9 107.2(2) . . ?
F8 C18 C11 111.2(2) . . ?
F7 C18 C11 110.6(2) . . ?
F9 C18 C11 114.3(2) . . ?
F11 C19 F12 107.6(2) . . ?
F11 C19 F10 107.29(19) . . ?
F12 C19 F10 106.39(19) . . ?
F11 C19 C11 112.2(2) . . ?
F12 C19 C11 110.62(19) . . ?
F10 C19 C11 112.4(2) . . ?
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 . . ?
C22 C21 C24 131.9(2) . . ?
C22 C21 W1 78.64(15) . . ?
C24 C21 W1 149.1(2) . . ?
C21 C22 C23 119.9(2) . . ?
C21 C22 C28 123.6(2) . . ?
C23 C22 C28 116.5(2) . . ?
C21 C22 W1 60.35(14) . . ?
C23 C22 W1 59.54(13) . . ?
C28 C22 W1 175.2(2) . . ?
C22 C23 C33 127.0(2) . . ?
C22 C23 W1 78.44(15) . . ?
C33 C23 W1 154.0(2) . . ?
C21 C24 C27 107.5(2) . . ?
C21 C24 C26 109.7(2) . . ?
C27 C24 C26 108.6(2) . . ?
C21 C24 C25 112.2(2) . . ?
C27 C24 C25 108.6(2) . . ?
C26 C24 C25 110.2(2) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 C28 C29 111.4(2) . . ?
C22 C28 H28A 109.3 . . ?
C29 C28 H28A 109.3 . . ?
C22 C28 H28B 109.3 . . ?
C29 C28 H28B 109.3 . . ?
H28A C28 H28B 108.0 . . ?
C30' C29 C28 119.4(5) . . ?
C30' C29 C30 33.1(4) . . ?
C28 C29 C30 114.8(3) . . ?
C30' C29 H29A 127.8 . . ?
C28 C29 H29A 108.6 . . ?
C30 C29 H29A 108.6 . . ?
C30' C29 H29B 76.6 . . ?
C28 C29 H29B 108.6 . . ?
C30 C29 H29B 108.6 . . ?
H29A C29 H29B 107.5 . . ?
C30' C29 H29C 107.5 . . ?
C28 C29 H29C 107.5 . . ?
C30 C29 H29C 133.3 . . ?
H29A C29 H29C 74.2 . . ?
H29B C29 H29C 36.0 . . ?
C30' C29 H29D 107.5 . . ?
C28 C29 H29D 107.5 . . ?
C30 C29 H29D 78.9 . . ?
H29A C29 H29D 34.3 . . ?
H29B C29 H29D 135.1 . . ?
H29C C29 H29D 107.0 . . ?
C31 C30 C29 115.3(4) . . ?
C31 C30 H30A 108.5 . . ?
C29 C30 H30A 108.5 . . ?
C31 C30 H30B 108.5 . . ?
C29 C30 H30B 108.5 . . ?
H30A C30 H30B 107.5 . . ?
C32 C31 C30 109.4(4) . . ?
C32 C31 H31A 109.8 . . ?
C30 C31 H31A 109.8 . . ?
C32 C31 H31B 109.8 . . ?
C30 C31 H31B 109.8 . . ?
H31A C31 H31B 108.2 . . ?
C32 C31 H32C 40.2 . . ?
C30 C31 H32C 149.5 . . ?
H31A C31 H32C 86.7 . . ?
H31B C31 H32C 87.6 . . ?
C29 C30' C31' 112.0(7) . . ?
C29 C30' H30C 109.2 . . ?
C31' C30' H30C 109.2 . . ?
C29 C30' H30D 109.2 . . ?
C31' C30' H30D 109.2 . . ?
H30C C30' H30D 107.9 . . ?
C30' C31' C32 111.1(5) . . ?
C30' C31' H31C 109.4 . . ?
C32 C31' H31C 109.4 . . ?
C30' C31' H31D 109.4 . . ?
C32 C31' H31D 109.4 . . ?
H31C C31' H31D 108.0 . . ?
C31 C32 C33 113.2(3) . . ?
C31 C32 C31' 42.5(3) . . ?
C33 C32 C31' 110.5(3) . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32A 108.9 . . ?
C31' C32 H32A 70.3 . . ?
C31 C32 H32B 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C31' C32 H32B 138.6 . . ?
H32A C32 H32B 107.8 . . ?
C31 C32 H32C 69.0 . . ?
C33 C32 H32C 109.6 . . ?
C31' C32 H32C 109.6 . . ?
H32A C32 H32C 138.3 . . ?
H32B C32 H32C 43.7 . . ?
C31 C32 H32D 135.4 . . ?
C33 C32 H32D 109.6 . . ?
C31' C32 H32D 109.6 . . ?
H32A C32 H32D 42.7 . . ?
H32B C32 H32D 67.4 . . ?
H32C C32 H32D 108.1 . . ?
C23 C33 C32 113.3(3) . . ?
C23 C33 H33A 108.9 . . ?
C32 C33 H33A 108.9 . . ?
C23 C33 H33B 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 1.338
_refine_diff_density_min -0.787
_refine_diff_density_rms 0.089
data_orei35
_database_code_depnum_ccdc_archive 'CCDC 907723'
#TrackingRef 'orei35.cif'
_audit_update_record
;
2012-07-03 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C32 H33 F12 N O2 W'
_chemical_formula_weight 875.44
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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M P21/c
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'
_cell_length_a 17.6465(14)
_cell_length_b 9.8689(8)
_cell_length_c 19.5331(16)
_cell_angle_alpha 90.00
_cell_angle_beta 104.391(1)
_cell_angle_gamma 90.00
_cell_volume 3295.0(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9867
_cell_measurement_theta_min 2.33
_cell_measurement_theta_max 32.62
_exptl_crystal_description plates
_exptl_crystal_colour brown
_exptl_crystal_size_max 0.19
_exptl_crystal_size_mid 0.09
_exptl_crystal_size_min 0.02
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.765
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1720
_exptl_absorpt_coefficient_mu 3.604
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.5475
_exptl_absorpt_correction_T_max 0.9314
_exptl_absorpt_process_details 'multiscan (SADABS, Blessing 1995)'
_exptl_special_details ?
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator 'Bruker Triumph'
_diffrn_measurement_device_type 'Bruker APEX-II DUO'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_decay_% 0
_diffrn_reflns_number 59838
_diffrn_reflns_av_R_equivalents 0.0320
_diffrn_reflns_av_sigmaI/netI 0.0191
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_theta_min 2.15
_diffrn_reflns_theta_max 27.50
_reflns_number_total 7570
_reflns_number_gt 6697
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'Bruker APEX2 (Bruker, 2008)'
_computing_cell_refinement 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT (Bruker, 2008)'
_computing_structure_solution 'Bruker SHELXTL (Bruker, 2008)'
_computing_structure_refinement 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
The W center is disordered and was refined in two positions with their site
occupation factors dependently refine to 0.930(1) and 0.070(1), for the major
and minor parts respectively. It is worth noting here that the major W center
is symmetrically coordinated to the C21/C23 atoms while W2 is asymmetrically
coordinated to them; 1.882(3)/1.908(3) \%A for W1 compared to2.387(6)/1.768(4)
\%A.
All H atoms were positioned geometrically ( C---H = 0.93/1.00 \%A) and allowed
to ride with U~iso~(H)= 1.2/1.5U~eq~(C).
Methyl ones were allowed to rotate around the corresponding C---C.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0212P)^2^+3.4670P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 7570
_refine_ls_number_parameters 441
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0276
_refine_ls_R_factor_gt 0.0220
_refine_ls_wR_factor_ref 0.0496
_refine_ls_wR_factor_gt 0.0482
_refine_ls_goodness_of_fit_ref 1.089
_refine_ls_restrained_S_all 1.089
_refine_ls_shift/su_max 0.005
_refine_ls_shift/su_mean 0.000
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
W1 W 0.261255(7) 0.113739(12) 0.811763(14) 0.01504(6) Uani 0.9304(12) 1 d P A 1
W2 W 0.26779(15) 0.1030(3) 0.8412(3) 0.0382(8) Uiso 0.0696(12) 1 d P A 2
F1 F 0.12235(10) 0.09632(17) 0.97631(8) 0.0324(4) Uani 1 1 d . A .
F2 F 0.08088(10) 0.27054(16) 0.91227(9) 0.0340(4) Uani 1 1 d . A .
F3 F 0.00216(9) 0.10696(17) 0.91612(9) 0.0319(4) Uani 1 1 d . A .
F4 F 0.06590(9) 0.05453(18) 0.72726(8) 0.0302(4) Uani 1 1 d . A .
F5 F 0.02483(10) 0.22881(16) 0.77325(9) 0.0332(4) Uani 1 1 d . A .
F6 F -0.02673(9) 0.03340(17) 0.78007(8) 0.0314(4) Uani 1 1 d . A .
F7 F 0.41208(10) 0.05060(19) 0.68993(10) 0.0403(4) Uani 1 1 d . A .
F8 F 0.49533(10) 0.0483(2) 0.79091(10) 0.0417(4) Uani 1 1 d . A .
F9 F 0.48651(10) -0.1236(2) 0.72217(11) 0.0450(5) Uani 1 1 d . A .
F10 F 0.36519(10) -0.23178(17) 0.87116(9) 0.0330(4) Uani 1 1 d . A .
F11 F 0.43859(10) -0.30439(18) 0.80637(11) 0.0444(5) Uani 1 1 d . A .
F12 F 0.47939(11) -0.1458(2) 0.88188(11) 0.0522(6) Uani 1 1 d . A .
O1 O 0.17148(10) 0.13624(17) 0.85287(9) 0.0206(4) Uani 1 1 d . . .
O2 O 0.36064(10) 0.02234(18) 0.81619(9) 0.0228(4) Uani 1 1 d . . .
N1 N 0.21824(12) -0.0767(2) 0.79621(11) 0.0177(4) Uani 1 1 d . . .
C1 C 0.10289(14) 0.0680(3) 0.85264(13) 0.0184(5) Uani 1 1 d . A .
C2 C 0.11545(14) -0.0845(2) 0.86260(12) 0.0173(5) Uani 1 1 d . . .
C3 C 0.17115(14) -0.1484(3) 0.83335(12) 0.0182(5) Uani 1 1 d . A .
C4 C 0.17994(15) -0.2893(3) 0.84141(13) 0.0222(5) Uani 1 1 d . . .
H4 H 0.2169 -0.3344 0.8215 0.027 Uiso 1 1 calc R A .
C5 C 0.13622(15) -0.3640(3) 0.87761(13) 0.0232(5) Uani 1 1 d . A .
H5 H 0.1433 -0.4593 0.8818 0.028 Uiso 1 1 calc R . .
C6 C 0.08212(15) -0.3015(3) 0.90784(13) 0.0221(5) Uani 1 1 d . . .
C7 C 0.07222(14) -0.1628(3) 0.89921(12) 0.0205(5) Uani 1 1 d . A .
H7 H 0.0346 -0.1190 0.9189 0.025 Uiso 1 1 calc R . .
C8 C 0.07569(16) 0.1359(3) 0.91440(14) 0.0242(6) Uani 1 1 d . . .
C9 C 0.04052(15) 0.0969(3) 0.78243(14) 0.0231(5) Uani 1 1 d . . .
C10 C 0.03580(17) -0.3822(3) 0.94906(15) 0.0301(6) Uani 1 1 d . A .
H10A H -0.0008 -0.3222 0.9647 0.045 Uiso 1 1 calc R . .
H10B H 0.0716 -0.4232 0.9904 0.045 Uiso 1 1 calc R . .
H10C H 0.0066 -0.4537 0.9189 0.045 Uiso 1 1 calc R . .
C11 C 0.38002(15) -0.0856(3) 0.77900(14) 0.0224(5) Uani 1 1 d . A .
C12 C 0.31078(14) -0.1465(3) 0.72448(14) 0.0209(5) Uani 1 1 d . . .
C13 C 0.23564(14) -0.1429(2) 0.73701(13) 0.0186(5) Uani 1 1 d . A .
C14 C 0.17381(15) -0.1999(3) 0.68582(13) 0.0219(5) Uani 1 1 d . . .
H14 H 0.1227 -0.1992 0.6934 0.026 Uiso 1 1 calc R A .
C15 C 0.18522(16) -0.2570(3) 0.62462(14) 0.0251(6) Uani 1 1 d . A .
H15 H 0.1419 -0.2947 0.5911 0.030 Uiso 1 1 calc R . .
C16 C 0.25916(16) -0.2604(3) 0.61123(14) 0.0254(6) Uani 1 1 d . . .
C17 C 0.32066(16) -0.2063(3) 0.66231(14) 0.0250(6) Uani 1 1 d . A .
H17 H 0.3718 -0.2100 0.6548 0.030 Uiso 1 1 calc R . .
C18 C 0.44433(16) -0.0281(3) 0.74514(17) 0.0327(7) Uani 1 1 d . . .
C19 C 0.41657(16) -0.1933(3) 0.83482(16) 0.0310(6) Uani 1 1 d . . .
C20 C 0.27189(18) -0.3167(3) 0.54311(15) 0.0339(7) Uani 1 1 d . A .
H20A H 0.2334 -0.3882 0.5255 0.051 Uiso 1 1 calc R . .
H20B H 0.3248 -0.3544 0.5517 0.051 Uiso 1 1 calc R . .
H20C H 0.2657 -0.2440 0.5079 0.051 Uiso 1 1 calc R . .
C21 C 0.25094(15) 0.2400(3) 0.73785(14) 0.0237(5) Uani 1 1 d . . .
C22 C 0.29451(16) 0.3188(3) 0.79783(15) 0.0276(6) Uani 1 1 d . A .
C23 C 0.31657(15) 0.2579(3) 0.86769(14) 0.0250(6) Uani 1 1 d . . .
C24 C 0.21884(17) 0.2786(3) 0.66144(15) 0.0298(6) Uani 1 1 d . A .
C25 C 0.19223(19) 0.1468(3) 0.62069(15) 0.0367(7) Uani 1 1 d . . .
H25A H 0.1710 0.1675 0.5705 0.055 Uiso 1 1 calc R A .
H25B H 0.1517 0.1034 0.6395 0.055 Uiso 1 1 calc R . .
H25C H 0.2370 0.0854 0.6261 0.055 Uiso 1 1 calc R . .
C26 C 0.14794(18) 0.3727(3) 0.65535(16) 0.0355(7) Uani 1 1 d . . .
H26A H 0.1266 0.3976 0.6057 0.053 Uiso 1 1 calc R A .
H26B H 0.1644 0.4547 0.6834 0.053 Uiso 1 1 calc R . .
H26C H 0.1077 0.3256 0.6730 0.053 Uiso 1 1 calc R . .
C27 C 0.2805(2) 0.3456(4) 0.62916(18) 0.0425(8) Uani 1 1 d . . .
H27A H 0.2569 0.3679 0.5795 0.064 Uiso 1 1 calc R A .
H27B H 0.3243 0.2831 0.6321 0.064 Uiso 1 1 calc R . .
H27C H 0.2995 0.4287 0.6553 0.064 Uiso 1 1 calc R . .
C28 C 0.32010(18) 0.4628(3) 0.78797(18) 0.0348(7) Uani 1 1 d . . .
H28A H 0.3672 0.4609 0.7700 0.052 Uiso 1 1 calc R A .
H28B H 0.3314 0.5104 0.8334 0.052 Uiso 1 1 calc R . .
H28C H 0.2782 0.5101 0.7541 0.052 Uiso 1 1 calc R . .
C29 C 0.36308(18) 0.3070(3) 0.93811(16) 0.0354(7) Uani 1 1 d . A .
C30 C 0.3195(2) 0.4179(4) 0.9680(2) 0.0589(11) Uani 1 1 d . . .
H30A H 0.3521 0.4492 1.0134 0.088 Uiso 1 1 calc R A .
H30B H 0.2703 0.3813 0.9747 0.088 Uiso 1 1 calc R . .
H30C H 0.3084 0.4941 0.9348 0.088 Uiso 1 1 calc R . .
C31 C 0.4448(2) 0.3544(4) 0.9343(2) 0.0562(10) Uani 1 1 d . . .
H31A H 0.4737 0.3872 0.9808 0.084 Uiso 1 1 calc R A .
H31B H 0.4398 0.4278 0.8997 0.084 Uiso 1 1 calc R . .
H31C H 0.4732 0.2784 0.9200 0.084 Uiso 1 1 calc R . .
C32 C 0.3717(2) 0.1810(4) 0.98587(17) 0.0511(9) Uani 1 1 d . . .
H32A H 0.4023 0.2044 1.0335 0.077 Uiso 1 1 calc R A .
H32B H 0.3986 0.1093 0.9664 0.077 Uiso 1 1 calc R . .
H32C H 0.3198 0.1492 0.9881 0.077 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
W1 0.01389(6) 0.01339(6) 0.01788(11) 0.00185(5) 0.00400(4) -0.00089(4)
F1 0.0388(9) 0.037(1) 0.0209(7) -0.0059(7) 0.0066(7) 0.0014(8)
F2 0.0411(10) 0.0196(8) 0.0476(10) -0.0056(7) 0.0231(8) 0.0008(7)
F3 0.0278(8) 0.0313(9) 0.0431(9) -0.0026(8) 0.0212(7) 0.0014(7)
F4 0.0297(9) 0.0397(10) 0.0205(7) 0.0048(7) 0.0045(6) 0.0074(7)
F5 0.0326(9) 0.0244(9) 0.0413(9) 0.0118(7) 0.0069(7) 0.0091(7)
F6 0.0184(8) 0.0387(10) 0.0344(9) 0.0102(7) 0.0015(6) -0.0030(7)
F7 0.0351(10) 0.0421(11) 0.0466(10) 0.0085(9) 0.0157(8) -0.0119(8)
F8 0.0218(9) 0.0460(11) 0.0588(12) -0.0086(9) 0.0129(8) -0.0148(8)
F9 0.0227(9) 0.0528(12) 0.0658(12) -0.0142(10) 0.0232(8) -0.0039(8)
F10 0.0317(9) 0.0306(9) 0.0344(9) 0.0086(7) 0.0038(7) 0.0029(7)
F11 0.0324(10) 0.0258(10) 0.0772(14) 0.0029(9) 0.0180(9) 0.0121(8)
F12 0.0297(10) 0.0406(11) 0.0695(13) 0.0115(10) -0.0192(9) -0.0034(8)
O1 0.0176(8) 0.0176(9) 0.0284(9) -0.0016(7) 0.0088(7) -0.0011(7)
O2 0.0165(9) 0.0191(9) 0.0316(10) -0.0008(8) 0.0039(7) 0.0003(7)
N1 0.0153(10) 0.0153(10) 0.0242(10) 0.0000(8) 0.0079(8) -0.0004(8)
C1 0.0160(12) 0.0181(12) 0.0219(12) 0.001(1) 0.0062(9) 0.0008(10)
C2 0.0169(11) 0.0175(13) 0.0159(11) 0.0013(9) 0.0010(9) 0.0000(9)
C3 0.0157(11) 0.0185(13) 0.0196(11) 0.0011(9) 0.0030(9) -0.0019(9)
C4 0.0204(13) 0.0188(13) 0.0279(13) 0.0014(10) 0.0069(10) 0.0018(10)
C5 0.0258(13) 0.0170(14) 0.0259(12) 0.0042(10) 0.0046(10) -0.001(1)
C6 0.0213(13) 0.0230(14) 0.0214(12) 0.0033(10) 0.0042(10) -0.0048(10)
C7 0.0195(12) 0.0234(13) 0.0187(11) 0.0003(10) 0.0048(9) -0.0003(10)
C8 0.0246(13) 0.0212(15) 0.0287(13) -0.0014(11) 0.0102(11) 0.0017(11)
C9 0.0208(12) 0.0216(14) 0.0272(13) 0.0066(10) 0.0064(10) 0.0033(10)
C10 0.0353(15) 0.0268(15) 0.0318(14) 0.0050(12) 0.0150(12) -0.0044(13)
C11 0.0159(12) 0.0185(14) 0.0339(14) -0.0001(10) 0.0083(10) -0.0001(10)
C12 0.0168(12) 0.0167(13) 0.0297(13) 0.0019(10) 0.007(1) 0.0005(10)
C13 0.0179(12) 0.0138(12) 0.0251(12) 0.0029(9) 0.0069(9) 0.0003(9)
C14 0.0170(12) 0.0211(13) 0.0282(13) 0.0018(10) 0.0068(10) -0.0014(10)
C15 0.0245(14) 0.0244(14) 0.0259(13) -0.0002(11) 0.0052(11) -0.0041(11)
C16 0.0301(14) 0.0210(14) 0.0273(13) 0.0015(11) 0.0112(11) 0.0000(11)
C17 0.0223(13) 0.0232(14) 0.0333(14) 0.0024(11) 0.0141(11) 0.0013(11)
C18 0.0193(14) 0.0344(17) 0.0468(17) -0.0033(14) 0.0129(12) -0.0052(12)
C19 0.0174(13) 0.0246(15) 0.0473(17) 0.0023(13) 0.0010(12) 0.0020(11)
C20 0.0401(17) 0.0356(17) 0.0290(14) -0.0031(13) 0.0143(13) -0.0002(14)
C21 0.0226(13) 0.0210(13) 0.0297(13) 0.0057(11) 0.0107(11) 0.0047(11)
C22 0.0210(13) 0.0246(15) 0.0411(15) 0.0026(12) 0.0151(12) 0.0032(11)
C23 0.0194(13) 0.0243(14) 0.0319(14) -0.0034(11) 0.0076(11) -0.0018(11)
C24 0.0312(15) 0.0307(16) 0.0309(14) 0.0107(12) 0.0142(12) 0.0089(12)
C25 0.0405(17) 0.0426(19) 0.0274(14) 0.0066(13) 0.0091(12) 0.0073(14)
C26 0.0360(16) 0.0384(18) 0.0344(15) 0.0126(13) 0.0132(13) 0.0103(14)
C27 0.0451(19) 0.046(2) 0.0431(18) 0.0141(15) 0.0237(15) 0.0061(16)
C28 0.0348(16) 0.0215(15) 0.0533(19) -0.0008(13) 0.0210(14) -0.0022(12)
C29 0.0304(16) 0.0391(19) 0.0336(15) -0.0072(13) 0.0022(12) -0.0037(13)
C30 0.065(3) 0.071(3) 0.0394(19) -0.0227(19) 0.0100(18) 0.003(2)
C31 0.0357(19) 0.068(3) 0.059(2) -0.012(2) -0.0001(16) -0.0170(18)
C32 0.043(2) 0.072(3) 0.0317(17) 0.0037(17) -0.0045(14) -0.0069(19)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
W1 C21 1.882(3) . ?
W1 C23 1.908(3) . ?
W1 O2 1.9549(17) . ?
W1 O1 1.9587(17) . ?
W1 N1 2.022(2) . ?
W1 C22 2.144(3) . ?
W2 C23 1.768(4) . ?
W2 O1 1.800(3) . ?
W2 O2 1.989(3) . ?
W2 N1 2.074(3) . ?
W2 C22 2.383(5) . ?
W2 C21 2.387(6) . ?
F1 C8 1.341(3) . ?
F2 C8 1.334(3) . ?
F3 C8 1.337(3) . ?
F4 C9 1.333(3) . ?
F5 C9 1.334(3) . ?
F6 C9 1.332(3) . ?
F7 C18 1.336(4) . ?
F8 C18 1.333(3) . ?
F9 C18 1.345(3) . ?
F10 C19 1.338(3) . ?
F11 C19 1.330(3) . ?
F12 C19 1.337(3) . ?
O1 C1 1.384(3) . ?
O2 C11 1.380(3) . ?
N1 C3 1.420(3) . ?
N1 C13 1.426(3) . ?
C1 C2 1.527(3) . ?
C1 C8 1.556(3) . ?
C1 C9 1.557(3) . ?
C2 C7 1.400(3) . ?
C2 C3 1.403(3) . ?
C3 C4 1.403(4) . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(4) . ?
C6 C10 1.510(3) . ?
C7 H7 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.530(4) . ?
C11 C19 1.544(4) . ?
C11 C18 1.556(4) . ?
C12 C17 1.400(4) . ?
C12 C13 1.407(3) . ?
C13 C14 1.401(3) . ?
C14 C15 1.381(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(4) . ?
C16 C20 1.510(4) . ?
C17 H17 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.456(4) . ?
C21 C24 1.508(4) . ?
C22 C23 1.453(4) . ?
C22 C28 1.517(4) . ?
C23 C29 1.496(4) . ?
C24 C27 1.536(4) . ?
C24 C25 1.536(4) . ?
C24 C26 1.539(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.533(5) . ?
C29 C31 1.535(5) . ?
C29 C32 1.539(5) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
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
C21 W1 C23 83.30(12) . . ?
C21 W1 O2 104.73(9) . . ?
C23 W1 O2 89.61(10) . . ?
C21 W1 O1 107.80(9) . . ?
C23 W1 O1 91.81(9) . . ?
O2 W1 O1 147.39(8) . . ?
C21 W1 N1 122.65(10) . . ?
C23 W1 N1 154.02(10) . . ?
O2 W1 N1 82.92(8) . . ?
O1 W1 N1 81.68(8) . . ?
C21 W1 C22 41.79(11) . . ?
C23 W1 C22 41.52(11) . . ?
O2 W1 C22 99.81(9) . . ?
O1 W1 C22 102.70(8) . . ?
N1 W1 C22 164.43(10) . . ?
C23 W2 O1 102.23(16) . . ?
C23 W2 O2 92.69(15) . . ?
O1 W2 O2 164.89(18) . . ?
C23 W2 N1 170.7(3) . . ?
O1 W2 N1 84.13(12) . . ?
O2 W2 N1 80.77(12) . . ?
C23 W2 C22 37.41(14) . . ?
O1 W2 C22 99.12(15) . . ?
O2 W2 C22 91.27(16) . . ?
N1 W2 C22 135.5(3) . . ?
C23 W2 C21 72.92(18) . . ?
O1 W2 C21 94.62(19) . . ?
O2 W2 C21 87.46(18) . . ?
N1 W2 C21 100.1(2) . . ?
C22 W2 C21 35.55(12) . . ?
C1 O1 W2 139.76(18) . . ?
C1 O1 W1 137.67(15) . . ?
W2 O1 W1 16.71(16) . . ?
C11 O2 W1 132.08(16) . . ?
C11 O2 W2 139.98(18) . . ?
W1 O2 W2 16.54(14) . . ?
C3 N1 C13 117.2(2) . . ?
C3 N1 W1 129.19(16) . . ?
C13 N1 W1 113.54(15) . . ?
C3 N1 W2 116.6(2) . . ?
C13 N1 W2 125.63(19) . . ?
W1 N1 W2 15.89(14) . . ?
O1 C1 C2 112.3(2) . . ?
O1 C1 C8 103.1(2) . . ?
C2 C1 C8 112.9(2) . . ?
O1 C1 C9 109.9(2) . . ?
C2 C1 C9 109.9(2) . . ?
C8 C1 C9 108.5(2) . . ?
C7 C2 C3 119.1(2) . . ?
C7 C2 C1 121.9(2) . . ?
C3 C2 C1 119.0(2) . . ?
C4 C3 C2 117.9(2) . . ?
C4 C3 N1 119.2(2) . . ?
C2 C3 N1 122.8(2) . . ?
C5 C4 C3 121.7(2) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 117.9(2) . . ?
C7 C6 C10 121.2(2) . . ?
C5 C6 C10 120.9(2) . . ?
C6 C7 C2 122.6(2) . . ?
C6 C7 H7 118.7 . . ?
C2 C7 H7 118.7 . . ?
F2 C8 F3 106.7(2) . . ?
F2 C8 F1 106.7(2) . . ?
F3 C8 F1 107.3(2) . . ?
F2 C8 C1 111.6(2) . . ?
F3 C8 C1 114.6(2) . . ?
F1 C8 C1 109.6(2) . . ?
F6 C9 F4 107.5(2) . . ?
F6 C9 F5 107.5(2) . . ?
F4 C9 F5 107.3(2) . . ?
F6 C9 C1 111.9(2) . . ?
F4 C9 C1 110.4(2) . . ?
F5 C9 C1 112.0(2) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C12 114.2(2) . . ?
O2 C11 C19 105.9(2) . . ?
C12 C11 C19 110.0(2) . . ?
O2 C11 C18 104.2(2) . . ?
C12 C11 C18 112.8(2) . . ?
C19 C11 C18 109.3(2) . . ?
C17 C12 C13 119.2(2) . . ?
C17 C12 C11 121.3(2) . . ?
C13 C12 C11 119.6(2) . . ?
C14 C13 C12 117.8(2) . . ?
C14 C13 N1 118.4(2) . . ?
C12 C13 N1 123.7(2) . . ?
C15 C14 C13 121.8(2) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 117.3(2) . . ?
C17 C16 C20 121.0(2) . . ?
C15 C16 C20 121.7(3) . . ?
C16 C17 C12 122.9(2) . . ?
C16 C17 H17 118.5 . . ?
C12 C17 H17 118.5 . . ?
F8 C18 F7 107.1(2) . . ?
F8 C18 F9 106.4(2) . . ?
F7 C18 F9 107.4(2) . . ?
F8 C18 C11 111.3(2) . . ?
F7 C18 C11 110.2(2) . . ?
F9 C18 C11 114.1(2) . . ?
F11 C19 F12 107.3(2) . . ?
F11 C19 F10 107.1(2) . . ?
F12 C19 F10 106.9(3) . . ?
F11 C19 C11 112.7(2) . . ?
F12 C19 C11 111.9(2) . . ?
F10 C19 C11 110.5(2) . . ?
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 . . ?
C22 C21 C24 130.9(2) . . ?
C22 C21 W1 78.78(16) . . ?
C24 C21 W1 150.2(2) . . ?
C22 C21 W2 72.07(17) . . ?
C24 C21 W2 156.6(2) . . ?
W1 C21 W2 7.04(7) . . ?
C23 C22 C21 120.0(2) . . ?
C23 C22 C28 119.2(3) . . ?
C21 C22 C28 120.8(3) . . ?
C23 C22 W1 60.53(15) . . ?
C21 C22 W1 59.43(14) . . ?
C28 C22 W1 178.6(2) . . ?
C23 C22 W2 47.66(18) . . ?
C21 C22 W2 72.38(19) . . ?
C28 C22 W2 166.8(2) . . ?
W1 C22 W2 13.10(11) . . ?
C22 C23 C29 133.4(3) . . ?
C22 C23 W2 94.9(3) . . ?
C29 C23 W2 131.7(3) . . ?
C22 C23 W1 77.96(17) . . ?
C29 C23 W1 148.6(2) . . ?
W2 C23 W1 17.25(17) . . ?
C21 C24 C27 112.6(3) . . ?
C21 C24 C25 106.9(2) . . ?
C27 C24 C25 108.0(2) . . ?
C21 C24 C26 109.1(2) . . ?
C27 C24 C26 110.7(2) . . ?
C25 C24 C26 109.4(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 C28 H28A 109.5 . . ?
C22 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C22 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C23 C29 C30 111.6(3) . . ?
C23 C29 C31 111.2(3) . . ?
C30 C29 C31 111.5(3) . . ?
C23 C29 C32 104.2(3) . . ?
C30 C29 C32 109.2(3) . . ?
C31 C29 C32 108.8(3) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.866
_refine_diff_density_min -0.821
_refine_diff_density_rms 0.076
data_orei36
_database_code_depnum_ccdc_archive 'CCDC 907724'
#TrackingRef 'orei36.cif'
_audit_update_record
;
2012-07-12 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C29 H31 F12 N O3 W'
_chemical_formula_weight 853.40
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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M P21/n
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'
_cell_length_a 11.4139(18)
_cell_length_b 9.5278(15)
_cell_length_c 28.609(5)
_cell_angle_alpha 90.00
_cell_angle_beta 97.389(3)
_cell_angle_gamma 90.00
_cell_volume 3085.4(8)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9869
_cell_measurement_theta_min 2.25
_cell_measurement_theta_max 33.47
_exptl_crystal_description plates
_exptl_crystal_colour blue
_exptl_crystal_size_max 0.42
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.02
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.837
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1672
_exptl_absorpt_coefficient_mu 3.849
_exptl_absorpt_correction_type numerical
_exptl_absorpt_correction_T_min 0.2954
_exptl_absorpt_correction_T_max 0.9201
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL v6.14 (Bruker 2008)'
_exptl_special_details ?
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator 'Bruker Triumph'
_diffrn_measurement_device_type 'Bruker APEX-II DUO'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 43295
_diffrn_reflns_av_R_equivalents 0.0459
_diffrn_reflns_av_sigmaI/netI 0.0264
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -37
_diffrn_reflns_limit_l_max 37
_diffrn_reflns_theta_min 1.85
_diffrn_reflns_theta_max 27.50
_reflns_number_total 7092
_reflns_number_gt 5724
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'Bruker APEX2 (Bruker, 2008)'
_computing_cell_refinement 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT (Bruker, 2008)'
_computing_structure_solution 'Bruker SHELXTL (Bruker, 2008)'
_computing_structure_refinement 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
The C28 unit is disordered and was refined in two parts (against the minor part
C28?). Their site occupation factors were fxed at 50% ratio after refined to
this value.
All H atoms were positioned geometrically ( C---H = 0.93/1.00 \%A) and allowed
to ride with U~iso~(H)= 1.2/1.5U~eq~(C).
Methyl ones were allowed to rotate around the corresponding C---C.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0177P)^2^+3.3570P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 7092
_refine_ls_number_parameters 412
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0350
_refine_ls_R_factor_gt 0.0242
_refine_ls_wR_factor_ref 0.0496
_refine_ls_wR_factor_gt 0.0473
_refine_ls_goodness_of_fit_ref 1.056
_refine_ls_restrained_S_all 1.056
_refine_ls_shift/su_max 0.003
_refine_ls_shift/su_mean 0.000
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
W1 W 0.254217(9) 1.002212(12) 0.357227(3) 0.01109(4) Uani 1 1 d . A .
F1 F -0.01691(15) 0.93368(19) 0.42915(6) 0.0249(4) Uani 1 1 d . A .
F2 F -0.09861(14) 0.88401(19) 0.35939(6) 0.0244(4) Uani 1 1 d . A .
F3 F -0.09892(14) 0.73240(18) 0.41460(6) 0.0221(4) Uani 1 1 d . A .
F4 F -0.01447(16) 0.65220(19) 0.31933(6) 0.0252(4) Uani 1 1 d . A .
F5 F 0.03300(16) 0.53150(16) 0.38239(6) 0.0234(4) Uani 1 1 d . A .
F6 F 0.16673(15) 0.59728(18) 0.34082(6) 0.0236(4) Uani 1 1 d . A .
F7 F 0.53196(15) 0.97863(17) 0.25999(5) 0.0217(4) Uani 1 1 d . A .
F8 F 0.54395(15) 1.18702(17) 0.28873(6) 0.0202(4) Uani 1 1 d . A .
F9 F 0.69080(14) 1.04617(18) 0.30305(6) 0.0203(4) Uani 1 1 d . A .
F10 F 0.58965(17) 1.20770(17) 0.38261(6) 0.0250(4) Uani 1 1 d . A .
F11 F 0.69463(14) 1.02172(18) 0.39569(6) 0.0212(4) Uani 1 1 d . A .
F12 F 0.53031(15) 1.04093(18) 0.42410(5) 0.0189(4) Uani 1 1 d . A .
O1 O 0.12250(16) 0.8710(2) 0.35215(6) 0.0130(4) Uani 1 1 d . . .
O2 O 0.40226(16) 1.0487(2) 0.33423(6) 0.0133(4) Uani 1 1 d . . .
O3 O 0.15929(17) 1.1282(2) 0.30448(7) 0.0177(4) Uani 1 1 d . . .
N1 N 0.34469(19) 0.8401(2) 0.38890(8) 0.0111(5) Uani 1 1 d . . .
C1 C 0.0874(2) 0.7769(3) 0.38458(9) 0.0123(5) Uani 1 1 d . A .
C2 C 0.1784(2) 0.7498(3) 0.42815(9) 0.0119(5) Uani 1 1 d . . .
C3 C 0.2994(2) 0.7754(3) 0.42765(9) 0.0110(5) Uani 1 1 d . A .
C4 C 0.3782(2) 0.7388(3) 0.46744(9) 0.0138(6) Uani 1 1 d . . .
H4 H 0.4603 0.7554 0.4674 0.017 Uiso 1 1 calc R A .
C5 C 0.3396(3) 0.6796(3) 0.50639(9) 0.0148(6) Uani 1 1 d . A .
H5 H 0.3952 0.6559 0.5328 0.018 Uiso 1 1 calc R . .
C6 C 0.2201(3) 0.6538(3) 0.50772(9) 0.0154(6) Uani 1 1 d . . .
C7 C 0.1421(2) 0.6892(3) 0.46846(9) 0.0138(6) Uani 1 1 d . A .
H7 H 0.0603 0.6717 0.4689 0.017 Uiso 1 1 calc R . .
C8 C -0.0329(3) 0.8312(3) 0.39729(10) 0.0172(6) Uani 1 1 d . . .
C9 C 0.0671(3) 0.6385(3) 0.35691(10) 0.0172(6) Uani 1 1 d . . .
C10 C 0.1781(3) 0.5899(4) 0.55068(10) 0.0236(7) Uani 1 1 d . A .
H10A H 0.1747 0.6625 0.5747 0.035 Uiso 1 1 calc R . .
H10B H 0.2329 0.5158 0.5632 0.035 Uiso 1 1 calc R . .
H10C H 0.0992 0.5497 0.5421 0.035 Uiso 1 1 calc R . .
C11 C 0.5172(2) 1.0001(3) 0.34172(9) 0.0123(5) Uani 1 1 d . A .
C12 C 0.5214(2) 0.8391(3) 0.34680(9) 0.0113(5) Uani 1 1 d . . .
C13 C 0.4359(2) 0.7689(3) 0.36987(9) 0.0119(5) Uani 1 1 d . A .
C14 C 0.4446(2) 0.6221(3) 0.37337(9) 0.0144(6) Uani 1 1 d . . .
H14 H 0.3875 0.5722 0.3882 0.017 Uiso 1 1 calc R A .
C15 C 0.5331(3) 0.5482(3) 0.3560(1) 0.0167(6) Uani 1 1 d . A .
H15 H 0.5358 0.4489 0.3592 0.020 Uiso 1 1 calc R . .
C16 C 0.6184(2) 0.6156(3) 0.33392(10) 0.0169(6) Uani 1 1 d . . .
C17 C 0.6109(2) 0.7610(3) 0.33008(10) 0.0151(6) Uani 1 1 d . A .
H17 H 0.6692 0.8093 0.3154 0.018 Uiso 1 1 calc R . .
C18 C 0.5726(2) 1.0532(3) 0.29822(10) 0.0155(6) Uani 1 1 d . . .
C19 C 0.5836(2) 1.0677(3) 0.38657(10) 0.0148(6) Uani 1 1 d . . .
C20 C 0.7151(3) 0.5346(3) 0.31471(12) 0.0247(7) Uani 1 1 d . A .
H20A H 0.7751 0.5071 0.3407 0.037 Uiso 1 1 calc R . .
H20B H 0.7514 0.5936 0.2925 0.037 Uiso 1 1 calc R . .
H20C H 0.6816 0.4504 0.2984 0.037 Uiso 1 1 calc R . .
C21 C 0.2363(2) 1.1017(3) 0.40738(9) 0.0128(5) Uani 1 1 d . . .
C22 C 0.2411(3) 1.1896(3) 0.45084(10) 0.0161(6) Uani 1 1 d . A .
C23 C 0.2936(3) 1.1016(4) 0.49332(10) 0.0270(7) Uani 1 1 d . . .
H23A H 0.2966 1.1580 0.5221 0.040 Uiso 1 1 calc R A .
H23B H 0.3736 1.0716 0.4890 0.040 Uiso 1 1 calc R . .
H23C H 0.2440 1.0188 0.4961 0.040 Uiso 1 1 calc R . .
C24 C 0.1174(3) 1.2400(3) 0.45791(11) 0.0232(7) Uani 1 1 d . . .
H24A H 0.1221 1.2973 0.4865 0.035 Uiso 1 1 calc R A .
H24B H 0.0664 1.1587 0.4610 0.035 Uiso 1 1 calc R . .
H24C H 0.0844 1.2963 0.4307 0.035 Uiso 1 1 calc R . .
C25 C 0.3202(3) 1.3175(3) 0.44543(12) 0.0256(7) Uani 1 1 d . . .
H25A H 0.3238 1.3763 0.4737 0.038 Uiso 1 1 calc R A .
H25B H 0.2874 1.3720 0.4178 0.038 Uiso 1 1 calc R . .
H25C H 0.4000 1.2856 0.4414 0.038 Uiso 1 1 calc R . .
C26 C 0.0890(3) 1.2526(3) 0.31352(11) 0.0239(7) Uani 1 1 d . A .
H26A H 0.0885 1.3192 0.2869 0.029 Uiso 1 1 calc R . .
H26B H 0.1261 1.3002 0.3425 0.029 Uiso 1 1 calc R . .
C27 C -0.0347(3) 1.2141(4) 0.31926(16) 0.0429(10) Uani 1 1 d . . .
H27A H -0.0789 1.2990 0.3253 0.064 Uiso 1 1 calc R A .
H27B H -0.0345 1.1494 0.3459 0.064 Uiso 1 1 calc R . .
H27C H -0.0722 1.1687 0.2904 0.064 Uiso 1 1 calc R . .
C28 C 0.1156(7) 1.0644(8) 0.2583(2) 0.0287(15) Uiso 0.50 1 d P A 1
H28A H 0.0337 1.0308 0.2590 0.034 Uiso 0.50 1 calc PR A 1
H28B H 0.1137 1.1371 0.2335 0.034 Uiso 0.50 1 calc PR A 1
C28' C 0.1660(6) 1.1005(7) 0.2542(2) 0.0223(14) Uiso 0.50 1 d P A 2
H28C H 0.2306 1.1567 0.2436 0.027 Uiso 0.50 1 calc PR A 2
H28D H 0.0910 1.1290 0.2353 0.027 Uiso 0.50 1 calc PR A 2
C29 C 0.1877(3) 0.9493(4) 0.24659(13) 0.0354(8) Uiso 1 1 d . . .
H29A H 0.1557 0.9114 0.2157 0.053 Uiso 0.50 1 calc PR A 1
H29B H 0.1879 0.8756 0.2705 0.053 Uiso 0.50 1 calc PR A 1
H29C H 0.2686 0.9822 0.2455 0.053 Uiso 0.50 1 calc PR A 1
H29D H 0.1917 0.9323 0.2130 0.053 Uiso 0.50 1 calc PR A 2
H29E H 0.1231 0.8939 0.2567 0.053 Uiso 0.50 1 calc PR A 2
H29F H 0.2625 0.9216 0.2650 0.053 Uiso 0.50 1 calc PR A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
W1 0.01040(5) 0.01105(5) 0.01185(5) 0.00291(5) 0.00152(3) 0.00097(5)
F1 0.0217(9) 0.0235(9) 0.0308(10) -0.0098(8) 0.0076(8) 0.0031(8)
F2 0.0126(8) 0.0329(10) 0.0272(9) 0.0087(8) 0.0009(7) 0.0043(8)
F3 0.0140(8) 0.0272(10) 0.0266(9) 0.0050(8) 0.0081(7) -0.0045(7)
F4 0.0261(10) 0.0292(10) 0.0179(9) -0.0048(8) -0.0065(7) -0.0055(8)
F5 0.0314(10) 0.0131(9) 0.0259(9) -0.0003(7) 0.0045(8) -0.0083(7)
F6 0.0221(9) 0.0230(9) 0.0271(9) -0.0100(8) 0.0086(8) -0.0002(8)
F7 0.0308(10) 0.0223(10) 0.0124(7) -0.0012(7) 0.0043(7) -0.0074(8)
F8 0.0256(10) 0.0147(8) 0.0210(9) 0.0060(7) 0.0061(7) -0.0034(7)
F9 0.0141(8) 0.0246(9) 0.0239(9) 0.0027(7) 0.0086(7) -0.0039(7)
F10 0.0416(11) 0.0109(8) 0.0208(9) -0.0007(7) -0.0027(8) -0.0045(8)
F11 0.0136(8) 0.0286(10) 0.0203(8) -0.0016(7) -0.0020(6) -0.0008(7)
F12 0.0215(9) 0.0243(9) 0.0114(8) 0.0000(7) 0.0037(7) -0.0002(7)
O1 0.0105(9) 0.0159(10) 0.0122(9) 0.0049(8) 0.0001(7) -0.0029(8)
O2 0.0084(9) 0.0153(9) 0.0169(9) 0.0062(8) 0.0040(7) 0.0016(7)
O3 0.0185(10) 0.0187(10) 0.0153(10) 0.0033(8) -0.0002(8) 0.0054(9)
N1 0.0116(11) 0.0103(11) 0.0119(11) 0.0033(9) 0.0037(9) 0.0023(9)
C1 0.0131(13) 0.0129(13) 0.0114(13) 0.0005(11) 0.0028(10) -0.0021(11)
C2 0.0121(13) 0.0120(13) 0.0115(13) -0.0023(11) 0.0011(11) 0.0000(11)
C3 0.0159(14) 0.0074(12) 0.0103(12) 0.0008(10) 0.0043(11) 0.0011(11)
C4 0.0129(14) 0.0144(13) 0.0140(13) 0.0017(11) 0.0015(11) -0.0003(11)
C5 0.0178(14) 0.0139(13) 0.0114(13) 0.0003(11) -0.0027(11) -0.0007(11)
C6 0.0203(15) 0.0161(14) 0.0105(13) -0.0002(11) 0.0040(11) -0.0025(12)
C7 0.0136(14) 0.0132(13) 0.0153(13) -0.0007(11) 0.0043(11) -0.0024(11)
C8 0.0158(15) 0.0180(14) 0.0183(14) 0.0019(12) 0.0037(12) -0.0019(12)
C9 0.0169(14) 0.0170(14) 0.0177(14) -0.0015(12) 0.0024(12) -0.0029(12)
C10 0.0225(16) 0.0325(18) 0.0161(15) 0.0071(13) 0.0040(12) -0.0046(14)
C11 0.0096(11) 0.0139(12) 0.0132(11) 0.0010(13) 0.0012(9) -0.0008(13)
C12 0.0116(13) 0.0115(13) 0.0107(12) -0.0006(10) 0.0004(10) -0.0013(10)
C13 0.0108(13) 0.0131(13) 0.0116(13) 0.0001(10) 0.0007(10) 0.0003(10)
C14 0.0137(14) 0.0150(14) 0.0148(13) 0.0019(11) 0.0030(11) -0.0006(11)
C15 0.0173(15) 0.0123(12) 0.0200(14) 0.0022(11) 0.0008(12) 0.0029(11)
C16 0.0144(14) 0.0166(14) 0.0195(14) -0.0030(12) 0.0019(11) 0.0024(12)
C17 0.0133(14) 0.0162(14) 0.0161(14) -0.0008(11) 0.0034(11) -0.0020(11)
C18 0.0130(14) 0.0167(13) 0.0170(14) 0.0013(11) 0.0024(11) -0.0033(11)
C19 0.0160(14) 0.0127(14) 0.0152(14) 0.0005(11) 0.0006(11) -0.0010(11)
C20 0.0210(16) 0.0194(16) 0.0353(18) -0.0029(13) 0.0099(14) 0.0047(12)
C21 0.0123(13) 0.0089(12) 0.0177(13) 0.0042(11) 0.0037(11) 0.0011(11)
C22 0.0172(15) 0.0134(14) 0.0178(14) -0.0001(11) 0.0030(12) 0.0002(11)
C23 0.038(2) 0.0273(17) 0.0137(14) -0.0014(13) -0.0020(13) 0.0065(15)
C24 0.0233(17) 0.0231(16) 0.0244(16) -0.0034(13) 0.0077(13) 0.0015(13)
C25 0.0282(18) 0.0198(16) 0.0303(17) -0.0071(14) 0.0095(14) -0.0041(14)
C26 0.0237(17) 0.0178(15) 0.0293(17) 0.0050(13) 0.0001(13) 0.0106(13)
C27 0.0221(19) 0.032(2) 0.074(3) 0.001(2) 0.0071(19) 0.0053(16)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
W1 C21 1.754(3) . ?
W1 O2 1.9419(18) . ?
W1 O1 1.9462(18) . ?
W1 N1 2.008(2) . ?
W1 O3 2.1144(19) . ?
F1 C8 1.332(3) . ?
F2 C8 1.335(3) . ?
F3 C8 1.340(3) . ?
F4 C9 1.335(3) . ?
F5 C9 1.340(3) . ?
F6 C9 1.339(3) . ?
F7 C18 1.336(3) . ?
F8 C18 1.336(3) . ?
F9 C18 1.340(3) . ?
F10 C19 1.341(3) . ?
F11 C19 1.335(3) . ?
F12 C19 1.325(3) . ?
O1 C1 1.385(3) . ?
O2 C11 1.382(3) . ?
O3 C26 1.473(3) . ?
O3 C28' 1.474(6) . ?
O3 C28 1.481(7) . ?
N1 C13 1.409(3) . ?
N1 C3 1.422(3) . ?
C1 C2 1.538(4) . ?
C1 C9 1.540(4) . ?
C1 C8 1.554(4) . ?
C2 C7 1.399(4) . ?
C2 C3 1.405(4) . ?
C3 C4 1.401(4) . ?
C4 C5 1.371(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(4) . ?
C6 C10 1.505(4) . ?
C7 H7 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.541(4) . ?
C11 C19 1.544(4) . ?
C11 C18 1.551(4) . ?
C12 C17 1.397(4) . ?
C12 C13 1.414(4) . ?
C13 C14 1.406(4) . ?
C14 C15 1.375(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(4) . ?
C16 C20 1.507(4) . ?
C17 H17 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.494(4) . ?
C22 C24 1.530(4) . ?
C22 C23 1.534(4) . ?
C22 C25 1.536(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.488(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.437(8) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28' C29 1.483(7) . ?
C28' H28C 0.9900 . ?
C28' H28D 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C29 H29D 0.9800 . ?
C29 H29E 0.9800 . ?
C29 H29F 0.9800 . ?
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
C21 W1 O2 110.62(11) . . ?
C21 W1 O1 103.76(10) . . ?
O2 W1 O1 144.97(8) . . ?
C21 W1 N1 98.87(11) . . ?
O2 W1 N1 84.79(8) . . ?
O1 W1 N1 83.51(9) . . ?
C21 W1 O3 100.02(10) . . ?
O2 W1 O3 90.97(8) . . ?
O1 W1 O3 89.50(8) . . ?
N1 W1 O3 160.94(8) . . ?
C1 O1 W1 130.73(16) . . ?
C11 O2 W1 136.15(16) . . ?
C26 O3 C28' 114.4(3) . . ?
C26 O3 C28 111.0(3) . . ?
C28' O3 C28 27.1(3) . . ?
C26 O3 W1 124.91(17) . . ?
C28' O3 W1 120.6(3) . . ?
C28 O3 W1 119.1(3) . . ?
C13 N1 C3 117.0(2) . . ?
C13 N1 W1 123.92(17) . . ?
C3 N1 W1 117.86(17) . . ?
O1 C1 C2 115.4(2) . . ?
O1 C1 C9 104.3(2) . . ?
C2 C1 C9 108.3(2) . . ?
O1 C1 C8 106.4(2) . . ?
C2 C1 C8 113.0(2) . . ?
C9 C1 C8 109.0(2) . . ?
C7 C2 C3 118.4(2) . . ?
C7 C2 C1 119.8(2) . . ?
C3 C2 C1 121.6(2) . . ?
C4 C3 C2 118.6(2) . . ?
C4 C3 N1 118.8(2) . . ?
C2 C3 N1 122.7(2) . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 117.8(2) . . ?
C7 C6 C10 121.5(3) . . ?
C5 C6 C10 120.7(3) . . ?
C6 C7 C2 122.8(3) . . ?
C6 C7 H7 118.6 . . ?
C2 C7 H7 118.6 . . ?
F1 C8 F2 107.0(2) . . ?
F1 C8 F3 107.2(2) . . ?
F2 C8 F3 106.3(2) . . ?
F1 C8 C1 110.9(2) . . ?
F2 C8 C1 110.9(2) . . ?
F3 C8 C1 114.1(2) . . ?
F4 C9 F6 106.7(2) . . ?
F4 C9 F5 106.9(2) . . ?
F6 C9 F5 106.4(2) . . ?
F4 C9 C1 111.9(2) . . ?
F6 C9 C1 110.5(2) . . ?
F5 C9 C1 114.0(2) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C12 111.5(2) . . ?
O2 C11 C19 110.1(2) . . ?
C12 C11 C19 109.3(2) . . ?
O2 C11 C18 104.1(2) . . ?
C12 C11 C18 112.9(2) . . ?
C19 C11 C18 108.9(2) . . ?
C17 C12 C13 119.1(2) . . ?
C17 C12 C11 120.9(2) . . ?
C13 C12 C11 120.0(2) . . ?
C14 C13 N1 120.0(2) . . ?
C14 C13 C12 117.2(2) . . ?
N1 C13 C12 122.8(2) . . ?
C15 C14 C13 122.2(3) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 C16 121.3(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 117.3(3) . . ?
C15 C16 C20 121.3(3) . . ?
C17 C16 C20 121.4(3) . . ?
C16 C17 C12 122.9(3) . . ?
C16 C17 H17 118.5 . . ?
C12 C17 H17 118.5 . . ?
F8 C18 F7 106.9(2) . . ?
F8 C18 F9 106.6(2) . . ?
F7 C18 F9 107.3(2) . . ?
F8 C18 C11 111.1(2) . . ?
F7 C18 C11 110.4(2) . . ?
F9 C18 C11 114.2(2) . . ?
F12 C19 F11 107.5(2) . . ?
F12 C19 F10 107.1(2) . . ?
F11 C19 F10 106.6(2) . . ?
F12 C19 C11 111.4(2) . . ?
F11 C19 C11 112.2(2) . . ?
F10 C19 C11 111.7(2) . . ?
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 . . ?
C22 C21 W1 171.2(2) . . ?
C21 C22 C24 110.5(2) . . ?
C21 C22 C23 108.8(2) . . ?
C24 C22 C23 109.9(2) . . ?
C21 C22 C25 108.7(2) . . ?
C24 C22 C25 109.2(2) . . ?
C23 C22 C25 109.8(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C26 C27 111.5(3) . . ?
O3 C26 H26A 109.3 . . ?
C27 C26 H26A 109.3 . . ?
O3 C26 H26B 109.3 . . ?
C27 C26 H26B 109.3 . . ?
H26A C26 H26B 108.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 O3 112.6(5) . . ?
C29 C28 H28A 109.1 . . ?
O3 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
O3 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
O3 C28' C29 110.3(4) . . ?
O3 C28' H28C 109.6 . . ?
C29 C28' H28C 109.6 . . ?
O3 C28' H28D 109.6 . . ?
C29 C28' H28D 109.6 . . ?
H28C C28' H28D 108.1 . . ?
C28 C29 C28' 27.4(3) . . ?
C28 C29 H29A 109.5 . . ?
C28' C29 H29A 116.1 . . ?
C28 C29 H29B 109.5 . . ?
C28' C29 H29B 125.3 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
C28' C29 H29C 82.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C29 H29D 117.0 . . ?
C28' C29 H29D 109.5 . . ?
H29A C29 H29D 27.9 . . ?
H29B C29 H29D 124.8 . . ?
H29C C29 H29D 81.9 . . ?
C28 C29 H29E 82.4 . . ?
C28' C29 H29E 109.5 . . ?
H29A C29 H29E 82.0 . . ?
H29B C29 H29E 48.9 . . ?
H29C C29 H29E 158.3 . . ?
H29D C29 H29E 109.5 . . ?
C28 C29 H29F 124.5 . . ?
C28' C29 H29F 109.5 . . ?
H29A C29 H29F 125.6 . . ?
H29B C29 H29F 60.6 . . ?
H29C C29 H29F 48.9 . . ?
H29D C29 H29F 109.5 . . ?
H29E C29 H29F 109.5 . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 1.537
_refine_diff_density_min -0.767
_refine_diff_density_rms 0.089