# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Ekkehardt Hahn' 'Volker Langenhahn' 'Tania Pape' _publ_contact_author_name 'Ekkehardt Hahn' _publ_contact_author_address ; Institut fur Anorganische und Analytische Chemie Westfalische Wilhelms Universitat Muenster Wilhelm Klemm-Strasse 8 M\"unster D-48149 GERMANY ; _publ_contact_author_email FEHAHN@UNI-MUENSTER.DE _publ_requested_journal 'Chemical Communications' _publ_section_title ; Template synthesis of tungsten complexes with saturated N-heterocyclic carbene ligands ; data_sad_a _database_code_depnum_ccdc_archive 'CCDC 280981' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H6 N2 O5 W' _chemical_formula_weight 394.00 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' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6670(10) _cell_length_b 8.5579(12) _cell_length_c 10.1724(15) _cell_angle_alpha 94.486(3) _cell_angle_beta 106.524(3) _cell_angle_gamma 100.679(3) _cell_volume 541.48(14) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 1 _cell_measurement_theta_max 22.5 _exptl_crystal_description 'transparent prism' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 10.674 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1420 _exptl_absorpt_correction_T_max 0.4467 _exptl_absorpt_process_details ; Corrections were done with the SADABS program, utilizing the none merged raw data obtained from the integration process. Integration and final cell refinement were done with SAINT. SADABS reports ratio of Tmin/Tmax = 0.326087 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean 80 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6155 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 30.03 _reflns_number_total 3109 _reflns_number_gt 2977 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker AXS, 2000)' _computing_cell_refinement 'SAINT (Bruker AXS, 2000)' _computing_data_reduction 'SAINT,SADABS (Bruker AXS, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565 ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0332P)^2^+0.0000P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0168(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3109 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.002 _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 W W 0.12544(2) 0.676994(16) 0.786072(14) 0.01504(9) Uani 1 1 d . . . C1 C -0.0395(7) 0.4195(6) 0.7377(4) 0.0175(8) Uani 1 1 d . . . N1 N -0.2401(6) 0.3594(5) 0.6601(5) 0.0270(9) Uani 1 1 d . . . H1 H -0.3278 0.4206 0.6234 0.032 Uiso 1 1 calc R . . C2 C -0.3053(8) 0.1844(6) 0.6400(6) 0.0302(10) Uani 1 1 d . . . H2A H -0.3448 0.1395 0.5411 0.036 Uiso 1 1 calc R . . H2B H -0.4271 0.1481 0.6757 0.036 Uiso 1 1 calc R . . C3 C -0.1028(9) 0.1385(6) 0.7248(6) 0.0368(12) Uani 1 1 d . . . H3A H -0.1276 0.0829 0.8024 0.044 Uiso 1 1 calc R . . H3B H -0.0487 0.0689 0.6667 0.044 Uiso 1 1 calc R . . N2 N 0.0459(7) 0.2952(5) 0.7756(5) 0.0292(9) Uani 1 1 d . . . H2 H 0.1798 0.3059 0.8268 0.035 Uiso 1 1 calc R . . C4 C 0.3077(7) 0.6348(6) 0.9734(5) 0.0196(8) Uani 1 1 d . . . O4 O 0.4109(6) 0.6155(5) 1.0780(4) 0.0286(8) Uani 1 1 d . . . C5 C 0.3396(7) 0.6240(6) 0.6942(5) 0.0209(8) Uani 1 1 d . . . O5 O 0.4632(6) 0.5981(6) 0.6403(4) 0.0331(9) Uani 1 1 d . . . C6 C -0.0911(7) 0.7391(6) 0.8759(5) 0.0222(9) Uani 1 1 d . . . O6 O -0.2094(6) 0.7812(6) 0.9247(4) 0.0340(9) Uani 1 1 d . . . C7 C -0.0639(7) 0.7223(6) 0.6034(5) 0.0220(8) Uani 1 1 d . . . O7 O -0.1720(7) 0.7544(6) 0.5052(4) 0.0384(10) Uani 1 1 d . . . C8 C 0.2855(7) 0.9052(6) 0.8262(5) 0.0224(8) Uani 1 1 d . . . O8 O 0.3797(7) 1.0374(5) 0.8454(4) 0.0386(9) Uani 1 1 d . . . 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 W 0.01774(11) 0.00975(11) 0.01669(11) 0.00226(6) 0.00432(7) 0.00201(6) C1 0.0223(18) 0.015(2) 0.0156(18) 0.0037(15) 0.0055(15) 0.0039(15) N1 0.0247(17) 0.017(2) 0.033(2) 0.0052(16) 0.0000(16) 0.0040(15) C2 0.031(2) 0.017(2) 0.037(3) 0.0039(19) 0.006(2) -0.0022(18) C3 0.052(3) 0.013(2) 0.036(3) 0.0043(19) 0.003(2) 0.002(2) N2 0.0304(19) 0.0149(19) 0.036(2) 0.0069(16) -0.0023(17) 0.0065(15) C4 0.0217(18) 0.014(2) 0.020(2) -0.0017(16) 0.0038(15) 0.0008(15) O4 0.0362(18) 0.0194(18) 0.0236(17) 0.0042(13) -0.0005(14) 0.0043(14) C5 0.0221(18) 0.017(2) 0.021(2) 0.0043(16) 0.0029(16) 0.0028(16) O5 0.0297(17) 0.043(2) 0.0298(19) 0.0027(17) 0.0112(15) 0.0140(17) C6 0.0255(19) 0.017(2) 0.021(2) 0.0057(16) 0.0035(16) 0.0018(16) O6 0.0334(18) 0.042(2) 0.0297(19) -0.0005(17) 0.0143(15) 0.0111(17) C7 0.0264(19) 0.016(2) 0.024(2) 0.0025(16) 0.0085(17) 0.0039(16) O7 0.046(2) 0.042(3) 0.0276(19) 0.0129(18) 0.0050(17) 0.016(2) C8 0.0269(19) 0.011(2) 0.027(2) 0.0003(16) 0.0062(17) 0.0003(16) O8 0.046(2) 0.0194(19) 0.042(2) 0.0034(16) 0.0101(18) -0.0060(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 W C8 1.993(5) . ? W C5 2.012(5) . ? W C7 2.039(5) . ? W C6 2.040(5) . ? W C4 2.047(4) . ? W C1 2.221(5) . ? C1 N1 1.326(6) . ? C1 N2 1.330(6) . ? N1 C2 1.461(6) . ? C2 C3 1.519(7) . ? C3 N2 1.468(7) . ? C4 O4 1.134(6) . ? C5 O5 1.155(6) . ? C6 O6 1.139(6) . ? C7 O7 1.140(6) . ? C8 O8 1.160(6) . ? 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 C8 W C5 88.52(19) . . ? C8 W C7 89.81(19) . . ? C5 W C7 90.97(18) . . ? C8 W C6 89.71(19) . . ? C5 W C6 177.74(15) . . ? C7 W C6 87.62(18) . . ? C8 W C4 89.96(19) . . ? C5 W C4 91.31(18) . . ? C7 W C4 177.70(14) . . ? C6 W C4 90.09(18) . . ? C8 W C1 177.08(15) . . ? C5 W C1 88.59(18) . . ? C7 W C1 90.65(18) . . ? C6 W C1 93.19(18) . . ? C4 W C1 89.68(17) . . ? N1 C1 N2 106.6(4) . . ? N1 C1 W 126.5(3) . . ? N2 C1 W 126.8(3) . . ? C1 N1 C2 115.2(4) . . ? N1 C2 C3 101.6(4) . . ? N2 C3 C2 102.4(4) . . ? C1 N2 C3 114.1(4) . . ? O4 C4 W 178.3(4) . . ? O5 C5 W 177.9(4) . . ? O6 C6 W 176.6(4) . . ? O7 C7 W 176.3(4) . . ? O8 C8 W 177.8(4) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 3.870 _refine_diff_density_min -3.117 _refine_diff_density_rms 0.240 data_sad _database_code_depnum_ccdc_archive 'CCDC 280982' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 N2 O5 W' _chemical_formula_weight 474.12 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' 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 P2(1)/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 11.181(5) _cell_length_b 10.629(5) _cell_length_c 13.731(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.519(8) _cell_angle_gamma 90.00 _cell_volume 1572.3(12) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 1 _cell_measurement_theta_max 22.5 _exptl_crystal_description 'transparent prism' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.003 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 7.370 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1947 _exptl_absorpt_correction_T_max 0.7095 _exptl_absorpt_process_details ; Corrections were done with the SADABS program, utilizing the none merged raw data obtained from the integration process. Integration and final cell refinement were done with SAINT. SADABS reports ratio of Tmin/Tmax = 0.489291 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean 80 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17607 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 30.12 _reflns_number_total 4579 _reflns_number_gt 4084 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker AXS, 2000)' _computing_cell_refinement 'SAINT (Bruker AXS, 2000)' _computing_data_reduction 'SAINT,SADABS (Bruker AXS, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565 ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0000P)^2^+0.8416P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4579 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0624 _refine_ls_wR_factor_gt 0.0606 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.002 _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 W W 0.804091(10) 0.810451(9) 0.045510(8) 0.01550(5) Uani 1 1 d . . . C1 C 0.8155(3) 0.5982(3) 0.0346(2) 0.0157(5) Uani 1 1 d . . . N1 N 0.8885(2) 0.5203(2) 0.10453(19) 0.0195(5) Uani 1 1 d . . . C2 C 0.8858(3) 0.3896(3) 0.0679(2) 0.0230(6) Uani 1 1 d . . . H2A H 0.8810 0.3286 0.1212 0.028 Uiso 1 1 calc R . . H2B H 0.9596 0.3706 0.0436 0.028 Uiso 1 1 calc R . . C3 C 0.7686(3) 0.3886(2) -0.0178(2) 0.0223(6) Uani 1 1 d . . . H3A H 0.7797 0.3404 -0.0765 0.027 Uiso 1 1 calc R . . H3B H 0.6979 0.3529 0.0038 0.027 Uiso 1 1 calc R . . N2 N 0.7506(2) 0.5248(2) -0.04135(18) 0.0187(5) Uani 1 1 d . . . C4 C 0.9912(3) 0.5554(3) 0.1887(2) 0.0244(6) Uani 1 1 d . . . H4A H 0.9832 0.6452 0.2051 0.029 Uiso 1 1 calc R . . H4B H 1.0698 0.5450 0.1693 0.029 Uiso 1 1 calc R . . C5 C 0.9960(3) 0.4776(3) 0.2800(2) 0.0251(6) Uani 1 1 d . . . H5 H 0.9279 0.4814 0.3090 0.030 Uiso 1 1 calc R . . C6 C 1.0900(4) 0.4039(3) 0.3223(3) 0.0350(8) Uani 1 1 d . . . H6A H 1.1591 0.3984 0.2947 0.042 Uiso 1 1 calc R . . H6B H 1.0886 0.3561 0.3805 0.042 Uiso 1 1 calc R . . C7 C 0.6548(3) 0.5604(3) -0.1306(2) 0.0208(6) Uani 1 1 d . . . H7A H 0.6709 0.5186 -0.1903 0.025 Uiso 1 1 calc R . . H7B H 0.6585 0.6524 -0.1405 0.025 Uiso 1 1 calc R . . C8 C 0.5275(3) 0.5258(3) -0.1242(2) 0.0247(6) Uani 1 1 d . . . H8 H 0.4960 0.5671 -0.0748 0.030 Uiso 1 1 calc R . . C9 C 0.4564(4) 0.4420(3) -0.1824(3) 0.0394(9) Uani 1 1 d . . . H9A H 0.4851 0.3990 -0.2325 0.047 Uiso 1 1 calc R . . H9B H 0.3763 0.4243 -0.1744 0.047 Uiso 1 1 calc R . . C10 C 0.7904(3) 0.7904(3) 0.1902(3) 0.0218(6) Uani 1 1 d . . . C11 C 0.9905(3) 0.8344(3) 0.0954(3) 0.0229(6) Uani 1 1 d . . . C12 C 0.8162(4) 0.8299(3) -0.0981(3) 0.0249(7) Uani 1 1 d . . . C13 C 0.6158(3) 0.8109(2) -0.0034(3) 0.0230(7) Uani 1 1 d . . . C14 C 0.7939(3) 0.9976(3) 0.0576(2) 0.0233(6) Uani 1 1 d . . . O10 O 0.7820(3) 0.7809(3) 0.2707(2) 0.0380(6) Uani 1 1 d . . . O11 O 1.0944(2) 0.8562(3) 0.1237(2) 0.0372(6) Uani 1 1 d . . . O12 O 0.8222(3) 0.8429(3) -0.1799(2) 0.0431(7) Uani 1 1 d . . . O13 O 0.5096(3) 0.8187(2) -0.0306(3) 0.0406(7) Uani 1 1 d . . . O14 O 0.7891(3) 1.1051(2) 0.0652(2) 0.0364(6) Uani 1 1 d . . . 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 W 0.01811(8) 0.01101(7) 0.01762(7) 0.00005(4) 0.00520(5) -0.00079(4) C1 0.0173(13) 0.0131(12) 0.0188(13) 0.0029(9) 0.0085(11) -0.0029(9) N1 0.0183(12) 0.0129(10) 0.0236(12) -0.0006(9) -0.0008(10) 0.0003(9) C2 0.0242(15) 0.0137(11) 0.0292(16) 0.0003(11) 0.0037(13) 0.0010(11) C3 0.0254(15) 0.0119(11) 0.0293(15) -0.0042(11) 0.0067(13) -0.0007(11) N2 0.0230(13) 0.0128(10) 0.0195(11) -0.0006(8) 0.0046(10) 0.0005(9) C4 0.0219(14) 0.0208(13) 0.0256(14) 0.0024(12) -0.0024(12) -0.0011(12) C5 0.0220(15) 0.0281(14) 0.0239(15) -0.0021(12) 0.0040(12) -0.0026(12) C6 0.037(2) 0.0339(18) 0.0284(17) 0.0098(14) -0.0007(15) 0.0018(15) C7 0.0251(15) 0.0193(12) 0.0178(12) -0.0020(11) 0.0054(11) -0.0023(12) C8 0.0224(15) 0.0233(14) 0.0283(16) 0.0025(12) 0.0067(13) 0.0009(12) C9 0.0301(18) 0.0329(18) 0.048(2) 0.0013(16) -0.0010(16) -0.0068(15) C10 0.0205(15) 0.0195(13) 0.0256(15) -0.0036(11) 0.0065(12) -0.0069(11) C11 0.0260(17) 0.0190(12) 0.0260(15) -0.0050(11) 0.0112(13) -0.0013(12) C12 0.0331(19) 0.0152(12) 0.0285(17) -0.0013(11) 0.0117(14) -0.0029(12) C13 0.0240(17) 0.0196(14) 0.0256(16) -0.0024(11) 0.0071(13) 0.0006(11) C14 0.0272(17) 0.0208(14) 0.0229(15) -0.0004(11) 0.0083(13) -0.0009(11) O10 0.0440(16) 0.0478(14) 0.0249(12) 0.0005(11) 0.0140(12) -0.0105(13) O11 0.0219(13) 0.0401(14) 0.0488(16) -0.0084(12) 0.0082(11) -0.0077(11) O12 0.072(2) 0.0336(12) 0.0303(14) 0.0054(11) 0.0256(14) -0.0051(14) O13 0.0250(14) 0.0435(16) 0.0508(18) -0.0022(12) 0.0058(13) 0.0032(11) O14 0.0519(17) 0.0148(10) 0.0399(14) -0.0024(9) 0.0079(13) 0.0049(10) _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 W C14 2.002(3) . ? W C12 2.023(4) . ? W C11 2.029(4) . ? W C13 2.031(4) . ? W C10 2.044(4) . ? W C1 2.266(3) . ? C1 N2 1.349(4) . ? C1 N1 1.362(4) . ? N1 C4 1.444(4) . ? N1 C2 1.475(4) . ? C2 C3 1.508(4) . ? C3 N2 1.485(3) . ? N2 C7 1.446(4) . ? C4 C5 1.490(4) . ? C5 C6 1.314(5) . ? C7 C8 1.495(4) . ? C8 C9 1.313(5) . ? C10 O10 1.138(4) . ? C11 O11 1.145(4) . ? C12 O12 1.151(4) . ? C13 O13 1.149(4) . ? C14 O14 1.150(4) . ? 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 C14 W C12 89.97(12) . . ? C14 W C11 85.61(13) . . ? C12 W C11 89.19(14) . . ? C14 W C13 87.03(12) . . ? C12 W C13 90.64(14) . . ? C11 W C13 172.63(12) . . ? C14 W C10 90.12(12) . . ? C12 W C10 179.55(12) . . ? C11 W C10 91.26(13) . . ? C13 W C10 88.92(14) . . ? C14 W C1 179.03(11) . . ? C12 W C1 91.00(11) . . ? C11 W C1 94.38(11) . . ? C13 W C1 92.99(10) . . ? C10 W C1 88.91(11) . . ? N2 C1 N1 106.8(2) . . ? N2 C1 W 126.8(2) . . ? N1 C1 W 126.34(19) . . ? C1 N1 C4 127.3(2) . . ? C1 N1 C2 112.2(2) . . ? C4 N1 C2 117.1(2) . . ? N1 C2 C3 102.0(2) . . ? N2 C3 C2 101.6(2) . . ? C1 N2 C7 128.8(2) . . ? C1 N2 C3 112.5(2) . . ? C7 N2 C3 117.8(2) . . ? N1 C4 C5 111.8(3) . . ? C6 C5 C4 123.2(3) . . ? N2 C7 C8 112.7(2) . . ? C9 C8 C7 124.1(3) . . ? O10 C10 W 179.1(3) . . ? O11 C11 W 175.6(3) . . ? O12 C12 W 178.8(3) . . ? O13 C13 W 176.0(2) . . ? O14 C14 W 179.3(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 30.12 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.894 _refine_diff_density_min -1.851 _refine_diff_density_rms 0.164