# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # 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. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mop _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 Mo N2 O6' _chemical_formula_weight 428.25 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' Mo Mo -1.6832 0.6857 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.4688(4) _cell_length_b 10.5106(4) _cell_length_c 9.4600(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.987(2) _cell_angle_gamma 90.00 _cell_volume 1685.43(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9948 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.62 _exptl_crystal_description C2/c _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.688 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.814 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8877 _exptl_absorpt_correction_T_max 0.9605 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12587 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.64 _reflns_number_total 1953 _reflns_number_gt 1858 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Ortep 3v2' _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^)+(0.0231P)^2^+1.4806P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1953 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0218 _refine_ls_R_factor_gt 0.0203 _refine_ls_wR_factor_ref 0.0544 _refine_ls_wR_factor_gt 0.0535 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.000 _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 Mo1 Mo 0.5000 0.709599(18) 0.2500 0.03669(8) Uani 1 2 d S . . O1 O 0.42563(10) 0.80686(14) 0.26640(19) 0.0623(4) Uani 1 1 d . . . O3 O 0.47872(7) 0.66518(12) 0.03955(12) 0.0411(3) Uani 1 1 d . . . O2 O 0.41616(7) 0.54423(12) 0.21542(11) 0.0394(3) Uani 1 1 d . . . N1 N 0.42273(8) 0.57455(14) -0.01073(14) 0.0385(3) Uani 1 1 d . . . H1 H 0.4074 0.5585 -0.1024 0.046 Uiso 1 1 calc R . . C1 C 0.39304(9) 0.51307(16) 0.08248(16) 0.0343(3) Uani 1 1 d . . . C2 C 0.33259(11) 0.4123(2) 0.02818(19) 0.0464(4) Uani 1 1 d . . . H2A H 0.3423 0.3748 -0.0596 0.056 Uiso 1 1 calc R . . H2B H 0.2807 0.4511 0.0028 0.056 Uiso 1 1 calc R . . C3 C 0.33332(10) 0.30913(18) 0.1382(2) 0.0418(4) Uani 1 1 d . . . C4 C 0.27686(13) 0.3063(2) 0.2193(2) 0.0565(5) Uani 1 1 d . . . H4 H 0.2372 0.3675 0.2037 0.068 Uiso 1 1 calc R . . C5 C 0.27929(18) 0.2135(3) 0.3224(3) 0.0800(9) Uani 1 1 d . . . H5 H 0.2408 0.2114 0.3751 0.096 Uiso 1 1 calc R . . C6 C 0.33746(19) 0.1249(3) 0.3479(3) 0.0936(11) Uani 1 1 d . . . H6 H 0.3400 0.0645 0.4207 0.112 Uiso 1 1 calc R . . C7 C 0.39245(17) 0.1243(3) 0.2665(4) 0.0917(10) Uani 1 1 d . . . H7 H 0.4313 0.0619 0.2819 0.110 Uiso 1 1 calc R . . C8 C 0.39031(14) 0.2166(2) 0.1612(3) 0.0649(6) Uani 1 1 d . . . H8 H 0.4277 0.2158 0.1059 0.078 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 Mo1 0.04469(13) 0.02829(11) 0.03720(12) 0.000 0.01011(9) 0.000 O1 0.0682(10) 0.0485(8) 0.0702(10) -0.0075(7) 0.0166(8) 0.0175(7) O3 0.0473(7) 0.0437(7) 0.0326(6) 0.0093(5) 0.0103(5) 0.0013(5) O2 0.0501(7) 0.0428(7) 0.0248(5) -0.0030(5) 0.0085(5) -0.0099(5) N1 0.0424(8) 0.0472(8) 0.0241(6) 0.0016(6) 0.0043(5) 0.0049(6) C1 0.0374(8) 0.0370(8) 0.0267(7) -0.0006(6) 0.0042(6) 0.0060(6) C2 0.0468(10) 0.0537(11) 0.0335(8) -0.0053(8) -0.0004(7) -0.0066(8) C3 0.0390(9) 0.0459(10) 0.0373(9) -0.0079(7) 0.0030(7) -0.0111(7) C4 0.0494(11) 0.0704(14) 0.0505(11) -0.0149(10) 0.0138(9) -0.0161(10) C5 0.0808(18) 0.110(2) 0.0507(13) -0.0078(14) 0.0180(13) -0.0528(17) C6 0.090(2) 0.096(2) 0.0767(18) 0.0339(16) -0.0141(15) -0.0565(18) C7 0.0668(16) 0.0615(16) 0.136(3) 0.0322(17) 0.0022(17) -0.0096(13) C8 0.0516(12) 0.0548(13) 0.0910(18) 0.0092(12) 0.0224(12) -0.0029(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 Mo1 O1 1.6894(14) 2_655 ? Mo1 O1 1.6894(14) . ? Mo1 O3 1.9904(12) 2_655 ? Mo1 O3 1.9904(12) . ? Mo1 O2 2.2454(12) . ? Mo1 O2 2.2454(12) 2_655 ? O3 N1 1.3659(19) . ? O2 C1 1.2675(18) . ? N1 C1 1.298(2) . ? N1 H1 0.8600 . ? C1 C2 1.496(2) . ? C2 C3 1.501(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C8 1.371(3) . ? C3 C4 1.388(3) . ? C4 C5 1.373(4) . ? C4 H4 0.9300 . ? C5 C6 1.356(4) . ? C5 H5 0.9300 . ? C6 C7 1.369(5) . ? C6 H6 0.9300 . ? C7 C8 1.384(4) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? 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 O1 Mo1 O1 105.52(12) 2_655 . ? O1 Mo1 O3 105.78(7) 2_655 2_655 ? O1 Mo1 O3 90.68(7) . 2_655 ? O1 Mo1 O3 90.68(7) 2_655 . ? O1 Mo1 O3 105.78(7) . . ? O3 Mo1 O3 152.87(7) 2_655 . ? O1 Mo1 O2 160.74(7) 2_655 . ? O1 Mo1 O2 89.59(6) . . ? O3 Mo1 O2 85.51(5) 2_655 . ? O3 Mo1 O2 73.45(4) . . ? O1 Mo1 O2 89.59(6) 2_655 2_655 ? O1 Mo1 O2 160.74(7) . 2_655 ? O3 Mo1 O2 73.45(4) 2_655 2_655 ? O3 Mo1 O2 85.51(5) . 2_655 ? O2 Mo1 O2 78.55(7) . 2_655 ? N1 O3 Mo1 117.18(9) . . ? C1 O2 Mo1 112.63(10) . . ? C1 N1 O3 118.73(13) . . ? C1 N1 H1 120.6 . . ? O3 N1 H1 120.6 . . ? O2 C1 N1 117.49(15) . . ? O2 C1 C2 123.55(15) . . ? N1 C1 C2 118.94(14) . . ? C1 C2 C3 112.72(14) . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C8 C3 C4 118.9(2) . . ? C8 C3 C2 120.43(18) . . ? C4 C3 C2 120.69(19) . . ? C5 C4 C3 120.2(2) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 120.5(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.0(3) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C7 C8 120.1(3) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C3 C8 C7 120.2(2) . . ? C3 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.64 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.232 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 795762' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # 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. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_wop _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 N2 O6 W' _chemical_formula_weight 516.16 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.4365(16) _cell_length_b 10.5304(16) _cell_length_c 9.4876(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.276(2) _cell_angle_gamma 90.00 _cell_volume 1688.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4363 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.13 _exptl_crystal_description Cubic _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.031 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 6.878 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4252 _exptl_absorpt_correction_T_max 0.7705 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5789 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1489 _reflns_number_gt 1450 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART APEX II (Bruker,2010)' _computing_cell_refinement 'SMART APEX II' _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Ortep 3v2' _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^)+(0.0264P)^2^+1.1470P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1489 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0182 _refine_ls_R_factor_gt 0.0174 _refine_ls_wR_factor_ref 0.0450 _refine_ls_wR_factor_gt 0.0446 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _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 0.0000 -0.208711(16) 0.2500 0.03524(9) Uani 1 2 d S . . O1 O -0.07560(19) -0.3070(2) 0.2647(4) 0.0585(8) Uani 1 1 d . . . O2 O 0.08323(12) -0.0430(2) 0.2848(2) 0.0352(5) Uani 1 1 d . . . O3 O 0.02117(13) -0.1648(2) 0.4593(2) 0.0368(5) Uani 1 1 d . . . N1 N 0.07776(15) -0.0746(3) 0.5105(3) 0.0344(6) Uani 1 1 d . . . H1 H 0.0935 -0.0594 0.6021 0.041 Uiso 1 1 calc R . . C1 C 0.10719(17) -0.0125(3) 0.4178(3) 0.0308(6) Uani 1 1 d . . . C2 C 0.1683(2) 0.0881(3) 0.4717(4) 0.0416(8) Uani 1 1 d . . . H2A H 0.1592 0.1254 0.5596 0.050 Uiso 1 1 calc R . . H2B H 0.2203 0.0489 0.4965 0.050 Uiso 1 1 calc R . . C3 C 0.1674(2) 0.1907(3) 0.3628(4) 0.0381(8) Uani 1 1 d . . . C4 C 0.1104(3) 0.2852(4) 0.3402(6) 0.0592(12) Uani 1 1 d . . . H4 H 0.0735 0.2870 0.3961 0.071 Uiso 1 1 calc R . . C5 C 0.1083(3) 0.3760(5) 0.2359(7) 0.0866(17) Uani 1 1 d . . . H5 H 0.0695 0.4387 0.2217 0.104 Uiso 1 1 calc R . . C6 C 0.1615(3) 0.3765(6) 0.1526(6) 0.0869(18) Uani 1 1 d . . . H6 H 0.1584 0.4373 0.0804 0.104 Uiso 1 1 calc R . . C7 C 0.2194(4) 0.2869(5) 0.1764(5) 0.0771(18) Uani 1 1 d . . . H7 H 0.2571 0.2887 0.1220 0.093 Uiso 1 1 calc R . . C8 C 0.2232(2) 0.1927(4) 0.2803(5) 0.0516(10) Uani 1 1 d . . . H8 H 0.2628 0.1314 0.2947 0.062 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 0.04239(13) 0.02740(12) 0.03599(13) 0.000 0.00978(8) 0.000 O1 0.0656(18) 0.0450(16) 0.0651(19) 0.0082(13) 0.0168(15) -0.0172(13) O2 0.0437(11) 0.0387(13) 0.0223(11) -0.0026(9) 0.0066(9) -0.0105(10) O3 0.0428(12) 0.0374(12) 0.0301(11) 0.0097(10) 0.0086(9) 0.0026(10) N1 0.0387(13) 0.0410(15) 0.0206(13) 0.0038(11) 0.0018(10) 0.0058(12) C1 0.0329(15) 0.0336(16) 0.0231(15) -0.0008(13) 0.0016(12) 0.0054(13) C2 0.0425(17) 0.048(2) 0.0288(17) -0.0053(14) -0.0021(13) -0.0069(15) C3 0.0333(16) 0.0412(19) 0.0349(18) -0.0092(14) -0.0006(14) -0.0118(14) C4 0.044(2) 0.049(3) 0.085(3) 0.006(2) 0.017(2) -0.0026(17) C5 0.058(3) 0.057(3) 0.131(5) 0.031(3) -0.001(3) -0.007(2) C6 0.080(3) 0.084(4) 0.077(3) 0.033(3) -0.019(3) -0.051(3) C7 0.084(4) 0.103(5) 0.046(3) -0.014(3) 0.018(3) -0.059(3) C8 0.045(2) 0.064(3) 0.045(2) -0.0166(19) 0.0103(17) -0.0146(17) _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 O1 1.709(3) 2 ? W1 O1 1.709(3) . ? W1 O3 1.983(2) . ? W1 O3 1.983(2) 2 ? W1 O2 2.242(2) . ? W1 O2 2.242(2) 2 ? O2 C1 1.270(3) . ? O3 N1 1.369(3) . ? N1 C1 1.298(4) . ? N1 H1 0.8600 . ? C1 C2 1.500(4) . ? C2 C3 1.493(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.385(5) . ? C3 C8 1.392(5) . ? C4 C5 1.370(7) . ? C4 H4 0.9300 . ? C5 C6 1.360(8) . ? C5 H5 0.9300 . ? C6 C7 1.359(8) . ? C6 H6 0.9300 . ? C7 C8 1.389(7) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? 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 O1 W1 O1 105.4(2) 2 . ? O1 W1 O3 105.44(13) 2 . ? O1 W1 O3 90.95(13) . . ? O1 W1 O3 90.95(13) 2 2 ? O1 W1 O3 105.44(13) . 2 ? O3 W1 O3 153.02(13) . 2 ? O1 W1 O2 89.96(12) 2 . ? O1 W1 O2 160.78(12) . . ? O3 W1 O2 73.57(8) . . ? O3 W1 O2 85.38(8) 2 . ? O1 W1 O2 160.78(12) 2 2 ? O1 W1 O2 89.95(12) . 2 ? O3 W1 O2 85.38(8) . 2 ? O3 W1 O2 73.57(8) 2 2 ? O2 W1 O2 77.74(12) . 2 ? C1 O2 W1 112.67(19) . . ? N1 O3 W1 117.16(17) . . ? C1 N1 O3 118.7(2) . . ? C1 N1 H1 120.7 . . ? O3 N1 H1 120.7 . . ? O2 C1 N1 117.3(3) . . ? O2 C1 C2 123.3(3) . . ? N1 C1 C2 119.4(3) . . ? C3 C2 C1 112.9(3) . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C8 118.5(4) . . ? C4 C3 C2 120.8(3) . . ? C8 C3 C2 120.7(3) . . ? C5 C4 C3 120.3(4) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 121.4(5) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C7 C6 C5 119.2(5) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C8 121.1(5) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C7 C8 C3 119.5(4) . . ? C7 C8 H8 120.2 . . ? C3 C8 H8 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 W1 O2 C1 -100.2(2) 2 . . . ? O1 W1 O2 C1 43.4(4) . . . . ? O3 W1 O2 C1 5.9(2) . . . . ? O3 W1 O2 C1 168.9(2) 2 . . . ? O2 W1 O2 C1 94.7(2) 2 . . . ? O1 W1 O3 N1 78.2(2) 2 . . . ? O1 W1 O3 N1 -175.5(2) . . . . ? O3 W1 O3 N1 -47.26(17) 2 . . . ? O2 W1 O3 N1 -7.08(18) . . . . ? O2 W1 O3 N1 -85.64(19) 2 . . . ? W1 O3 N1 C1 8.2(3) . . . . ? W1 O2 C1 N1 -3.7(3) . . . . ? W1 O2 C1 C2 174.8(2) . . . . ? O3 N1 C1 O2 -2.4(4) . . . . ? O3 N1 C1 C2 179.1(3) . . . . ? O2 C1 C2 C3 30.3(4) . . . . ? N1 C1 C2 C3 -151.2(3) . . . . ? C1 C2 C3 C4 77.8(4) . . . . ? C1 C2 C3 C8 -101.4(4) . . . . ? C8 C3 C4 C5 1.9(6) . . . . ? C2 C3 C4 C5 -177.4(4) . . . . ? C3 C4 C5 C6 -0.3(8) . . . . ? C4 C5 C6 C7 -1.8(8) . . . . ? C5 C6 C7 C8 2.3(7) . . . . ? C6 C7 C8 C3 -0.7(6) . . . . ? C4 C3 C8 C7 -1.4(6) . . . . ? C2 C3 C8 C7 177.9(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.491 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 878566'