# 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_fm02B811_C2C _database_code_depnum_ccdc_archive 'CCDC 893974' #TrackingRef 'fm02B811_C2C.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H5 Cl3 O3 W' _chemical_formula_weight 427.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 25.582(7) _cell_length_b 10.818(3) _cell_length_c 18.629(5) _cell_angle_alpha 90.00 _cell_angle_beta 123.914(3) _cell_angle_gamma 90.00 _cell_volume 4278(2) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3016 _cell_measurement_theta_min 2.232 _cell_measurement_theta_max 26.664 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3136 _exptl_absorpt_coefficient_mu 11.524 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1958 _exptl_absorpt_correction_T_max 0.2768 _exptl_absorpt_process_details ? _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 graphite _diffrn_measurement_device_type 'CCD area detector' _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 14605 _diffrn_reflns_av_R_equivalents 0.0864 _diffrn_reflns_av_sigmaI/netI 0.0814 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3789 _reflns_number_gt 2836 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0509P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3789 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 C1 C 0.0670(5) 0.7708(9) 0.3593(7) 0.026(2) Uani 1 1 d . . . H1 H 0.0357 0.7187 0.3556 0.031 Uiso 1 1 calc R . . C2 C 0.0992(5) 0.8572(9) 0.4339(7) 0.023(2) Uani 1 1 d . . . C3 C 0.1467(5) 0.9350(9) 0.4424(6) 0.024(2) Uani 1 1 d . . . C4 C 0.1767(5) 1.0163(9) 0.5131(7) 0.024(2) Uani 1 1 d . . . H4 H 0.2085 1.0705 0.5204 0.029 Uiso 1 1 calc R . . C5 C 0.1602(5) 1.0175(9) 0.5710(8) 0.034(3) Uani 1 1 d . . . H5 H 0.1817 1.0716 0.6194 0.041 Uiso 1 1 calc R . . C6 C 0.1136(5) 0.9427(10) 0.5613(7) 0.035(3) Uani 1 1 d . . . H6 H 0.1025 0.9462 0.6021 0.042 Uiso 1 1 calc R . . C7 C 0.0829(5) 0.8630(9) 0.4930(7) 0.031(3) Uani 1 1 d . . . H7 H 0.0503 0.8116 0.4862 0.037 Uiso 1 1 calc R . . C11 C 0.0806(5) 0.4796(9) 0.2698(7) 0.031(3) Uani 1 1 d . . . H11 H 0.0580 0.5345 0.2221 0.037 Uiso 1 1 calc R . . C12 C 0.1261(5) 0.3985(9) 0.2719(7) 0.028(2) Uani 1 1 d . . . C13 C 0.1620(5) 0.3128(9) 0.3390(7) 0.026(2) Uani 1 1 d . . . C14 C 0.2031(5) 0.2331(9) 0.3354(7) 0.030(3) Uani 1 1 d . . . H14 H 0.2262 0.1733 0.3796 0.036 Uiso 1 1 calc R . . C15 C 0.2098(5) 0.2413(9) 0.2681(7) 0.028(3) Uani 1 1 d . . . H15 H 0.2385 0.1878 0.2663 0.033 Uiso 1 1 calc R . . C16 C 0.1756(5) 0.3266(9) 0.2019(8) 0.032(3) Uani 1 1 d . . . H16 H 0.1818 0.3326 0.1563 0.039 Uiso 1 1 calc R . . C17 C 0.1336(5) 0.4007(9) 0.2025(7) 0.030(3) Uani 1 1 d . . . H17 H 0.1086 0.4554 0.1554 0.035 Uiso 1 1 calc R . . Cl1 Cl 0.05710(13) 1.0007(2) 0.21422(19) 0.0343(7) Uani 1 1 d . . . Cl2 Cl 0.20647(13) 0.6949(2) 0.34863(18) 0.0323(6) Uani 1 1 d . . . Cl3 Cl 0.09103(13) 0.7547(2) 0.15351(17) 0.0312(6) Uani 1 1 d . . . Cl4 Cl 0.02924(14) 0.2518(3) 0.3717(2) 0.0455(8) Uani 1 1 d . . . Cl5 Cl 0.18298(12) 0.5490(3) 0.49862(18) 0.0342(7) Uani 1 1 d . . . Cl6 Cl 0.04980(13) 0.5079(3) 0.47054(18) 0.0345(7) Uani 1 1 d . . . O1 O 0.1927(3) 0.9489(6) 0.2681(4) 0.0250(16) Uani 1 1 d . . . O2 O 0.0764(3) 0.7594(6) 0.3023(4) 0.0269(16) Uani 1 1 d . . . O3 O 0.1651(3) 0.9340(6) 0.3878(5) 0.0279(17) Uani 1 1 d . . . O4 O 0.1509(4) 0.3042(7) 0.5467(5) 0.0344(19) Uani 1 1 d . . . O5 O 0.0690(3) 0.4826(6) 0.3255(5) 0.0253(16) Uani 1 1 d . . . O6 O 0.1567(3) 0.3056(6) 0.4078(5) 0.0293(17) Uani 1 1 d . . . W1 W 0.142663(19) 0.86680(4) 0.28178(3) 0.02290(15) Uani 1 1 d . . . W2 W 0.114548(19) 0.38061(4) 0.45226(3) 0.02528(16) 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 C1 0.022(5) 0.030(5) 0.024(6) 0.008(4) 0.012(5) 0.002(4) C2 0.022(5) 0.025(5) 0.024(5) 0.003(4) 0.014(5) 0.006(4) C3 0.018(5) 0.025(5) 0.021(5) 0.003(4) 0.005(5) 0.002(4) C4 0.024(6) 0.023(5) 0.027(6) 0.001(4) 0.016(5) 0.000(4) C5 0.034(7) 0.021(5) 0.038(7) -0.006(5) 0.015(6) -0.003(5) C6 0.046(8) 0.030(6) 0.036(7) -0.011(5) 0.028(6) 0.004(5) C7 0.028(6) 0.031(5) 0.035(7) 0.002(5) 0.019(5) 0.000(5) C11 0.026(6) 0.032(6) 0.017(6) 0.003(4) 0.002(5) -0.001(5) C12 0.029(6) 0.030(5) 0.021(6) -0.009(4) 0.012(5) -0.008(5) C13 0.016(5) 0.033(5) 0.023(6) -0.003(4) 0.008(5) -0.005(4) C14 0.026(6) 0.027(5) 0.033(6) -0.004(5) 0.013(5) -0.006(5) C15 0.022(5) 0.022(5) 0.043(7) -0.011(5) 0.020(5) -0.007(4) C16 0.042(7) 0.029(5) 0.035(7) -0.008(5) 0.027(6) -0.007(5) C17 0.034(6) 0.027(5) 0.019(6) -0.005(4) 0.010(5) -0.006(5) Cl1 0.0299(15) 0.0343(14) 0.0374(16) 0.0048(12) 0.0180(13) 0.0077(11) Cl2 0.0321(15) 0.0308(13) 0.0351(16) 0.0070(11) 0.0194(13) 0.0043(11) Cl3 0.0352(15) 0.0354(14) 0.0249(14) -0.0051(11) 0.0179(12) -0.0036(12) Cl4 0.0345(16) 0.0399(16) 0.0460(18) -0.0037(13) 0.0125(15) -0.0109(13) Cl5 0.0216(13) 0.0429(15) 0.0312(15) -0.0004(12) 0.0104(12) -0.0041(12) Cl6 0.0287(15) 0.0467(16) 0.0308(15) 0.0007(12) 0.0182(13) 0.0031(12) O1 0.025(4) 0.028(4) 0.026(4) 0.000(3) 0.017(3) -0.001(3) O2 0.026(4) 0.036(4) 0.019(4) -0.006(3) 0.013(3) -0.007(3) O3 0.035(4) 0.029(4) 0.025(4) -0.005(3) 0.021(4) -0.007(3) O4 0.028(4) 0.043(4) 0.033(5) 0.002(3) 0.018(4) 0.004(3) O5 0.024(4) 0.031(4) 0.020(4) 0.003(3) 0.013(3) 0.003(3) O6 0.028(4) 0.037(4) 0.023(4) 0.006(3) 0.014(3) 0.012(3) W1 0.0220(3) 0.0255(2) 0.0227(3) 0.00032(17) 0.0133(2) 0.00044(17) W2 0.0207(3) 0.0319(3) 0.0220(3) 0.00269(17) 0.0111(2) 0.00087(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 C1 O2 1.217(13) . ? C1 C2 1.485(14) . ? C1 H1 0.9500 . ? C2 C7 1.379(15) . ? C2 C3 1.412(15) . ? C3 O3 1.340(13) . ? C3 C4 1.403(14) . ? C4 C5 1.359(16) . ? C4 H4 0.9500 . ? C5 C6 1.368(16) . ? C5 H5 0.9500 . ? C6 C7 1.365(15) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C11 O5 1.227(13) . ? C11 C12 1.441(16) . ? C11 H11 0.9500 . ? C12 C13 1.408(15) . ? C12 C17 1.410(15) . ? C13 O6 1.364(13) . ? C13 C14 1.389(15) . ? C14 C15 1.362(16) . ? C14 H14 0.9500 . ? C15 C16 1.391(15) . ? C15 H15 0.9500 . ? C16 C17 1.345(16) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? Cl1 W1 2.324(3) . ? Cl2 W1 2.325(3) . ? Cl3 W1 2.325(3) . ? Cl4 W2 2.303(3) . ? Cl5 W2 2.333(3) . ? Cl6 W2 2.321(3) . ? O1 W1 1.690(7) . ? O2 W1 2.257(7) . ? O3 W1 1.869(7) . ? O4 W2 1.678(8) . ? O5 W2 2.254(7) . ? O6 W2 1.872(7) . ? 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 O2 C1 C2 127.2(10) . . ? O2 C1 H1 116.4 . . ? C2 C1 H1 116.4 . . ? C7 C2 C3 120.4(10) . . ? C7 C2 C1 121.3(10) . . ? C3 C2 C1 118.2(10) . . ? O3 C3 C4 118.5(9) . . ? O3 C3 C2 123.7(9) . . ? C4 C3 C2 117.8(10) . . ? C5 C4 C3 120.1(10) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 121.5(10) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C7 C6 C5 120.2(12) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C2 120.0(11) . . ? C6 C7 H7 120.0 . . ? C2 C7 H7 120.0 . . ? O5 C11 C12 124.4(10) . . ? O5 C11 H11 117.8 . . ? C12 C11 H11 117.8 . . ? C13 C12 C17 118.1(10) . . ? C13 C12 C11 122.8(10) . . ? C17 C12 C11 119.1(10) . . ? O6 C13 C14 118.9(9) . . ? O6 C13 C12 120.9(9) . . ? C14 C13 C12 120.2(11) . . ? C15 C14 C13 119.4(10) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 121.3(10) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C17 C16 C15 120.0(11) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C12 121.0(10) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? C1 O2 W1 128.8(7) . . ? C3 O3 W1 140.8(6) . . ? C11 O5 W2 130.2(7) . . ? C13 O6 W2 140.8(6) . . ? O1 W1 O3 98.2(3) . . ? O1 W1 O2 178.9(3) . . ? O3 W1 O2 80.7(3) . . ? O1 W1 Cl1 98.9(2) . . ? O3 W1 Cl1 88.3(2) . . ? O2 W1 Cl1 80.97(19) . . ? O1 W1 Cl3 99.4(2) . . ? O3 W1 Cl3 162.3(2) . . ? O2 W1 Cl3 81.71(19) . . ? Cl1 W1 Cl3 86.87(10) . . ? O1 W1 Cl2 97.8(2) . . ? O3 W1 Cl2 92.0(2) . . ? O2 W1 Cl2 82.34(19) . . ? Cl1 W1 Cl2 163.02(10) . . ? Cl3 W1 Cl2 87.69(10) . . ? O4 W2 O6 97.6(3) . . ? O4 W2 O5 177.9(3) . . ? O6 W2 O5 80.6(3) . . ? O4 W2 Cl4 98.9(3) . . ? O6 W2 Cl4 91.1(2) . . ? O5 W2 Cl4 82.28(19) . . ? O4 W2 Cl6 99.3(3) . . ? O6 W2 Cl6 163.1(2) . . ? O5 W2 Cl6 82.5(2) . . ? Cl4 W2 Cl6 87.73(12) . . ? O4 W2 Cl5 97.7(3) . . ? O6 W2 Cl5 90.2(2) . . ? O5 W2 Cl5 81.24(19) . . ? Cl4 W2 Cl5 163.02(10) . . ? Cl6 W2 Cl5 86.09(10) . . ? 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 O2 C1 C2 C7 178.3(10) . . . . ? O2 C1 C2 C3 -0.9(16) . . . . ? C7 C2 C3 O3 179.7(9) . . . . ? C1 C2 C3 O3 -1.1(14) . . . . ? C7 C2 C3 C4 0.7(14) . . . . ? C1 C2 C3 C4 179.9(9) . . . . ? O3 C3 C4 C5 -178.4(9) . . . . ? C2 C3 C4 C5 0.7(14) . . . . ? C3 C4 C5 C6 -1.6(16) . . . . ? C4 C5 C6 C7 1.0(17) . . . . ? C5 C6 C7 C2 0.4(17) . . . . ? C3 C2 C7 C6 -1.3(16) . . . . ? C1 C2 C7 C6 179.5(10) . . . . ? O5 C11 C12 C13 0.5(17) . . . . ? O5 C11 C12 C17 177.8(10) . . . . ? C17 C12 C13 O6 -179.7(9) . . . . ? C11 C12 C13 O6 -2.3(16) . . . . ? C17 C12 C13 C14 -0.4(15) . . . . ? C11 C12 C13 C14 177.0(9) . . . . ? O6 C13 C14 C15 -178.5(9) . . . . ? C12 C13 C14 C15 2.2(15) . . . . ? C13 C14 C15 C16 -1.2(15) . . . . ? C14 C15 C16 C17 -1.8(16) . . . . ? C15 C16 C17 C12 3.7(16) . . . . ? C13 C12 C17 C16 -2.6(16) . . . . ? C11 C12 C17 C16 179.9(10) . . . . ? C2 C1 O2 W1 -2.5(15) . . . . ? C4 C3 O3 W1 -172.1(7) . . . . ? C2 C3 O3 W1 8.9(16) . . . . ? C12 C11 O5 W2 4.5(15) . . . . ? C14 C13 O6 W2 178.7(8) . . . . ? C12 C13 O6 W2 -2.0(17) . . . . ? C3 O3 W1 O1 170.8(10) . . . . ? C3 O3 W1 O2 -9.1(10) . . . . ? C3 O3 W1 Cl1 72.0(10) . . . . ? C3 O3 W1 Cl3 -2.3(16) . . . . ? C3 O3 W1 Cl2 -91.0(10) . . . . ? C1 O2 W1 O1 0(16) . . . . ? C1 O2 W1 O3 5.5(8) . . . . ? C1 O2 W1 Cl1 -84.3(8) . . . . ? C1 O2 W1 Cl3 -172.4(9) . . . . ? C1 O2 W1 Cl2 98.8(8) . . . . ? C13 O6 W2 O4 -174.3(10) . . . . ? C13 O6 W2 O5 4.6(10) . . . . ? C13 O6 W2 Cl4 86.6(10) . . . . ? C13 O6 W2 Cl6 0.8(17) . . . . ? C13 O6 W2 Cl5 -76.5(10) . . . . ? C11 O5 W2 O4 25(9) . . . . ? C11 O5 W2 O6 -5.7(9) . . . . ? C11 O5 W2 Cl4 -98.1(9) . . . . ? C11 O5 W2 Cl6 173.2(9) . . . . ? C11 O5 W2 Cl5 86.0(9) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.303 _refine_diff_density_min -1.429 _refine_diff_density_rms 0.282 data_fm11D511_CC _database_code_depnum_ccdc_archive 'CCDC 893975' #TrackingRef 'fm11D511_CC.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H7 Cl4 O3 W' _chemical_formula_weight 428.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc 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' _cell_length_a 10.2279(18) _cell_length_b 8.4464(15) _cell_length_c 12.946(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.452(2) _cell_angle_gamma 90.00 _cell_volume 1054.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2008 _cell_measurement_theta_min 3.206 _cell_measurement_theta_max 27.7145 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.700 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 11.932 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2362 _exptl_absorpt_correction_T_max 0.3536 _exptl_absorpt_process_details ? _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 graphite _diffrn_measurement_device_type 'CCD area detector' _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 3908 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0717 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2015 _reflns_number_gt 1918 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0115P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.014(15) _refine_ls_number_reflns 2015 _refine_ls_number_parameters 119 _refine_ls_number_restraints 63 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0733 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.979 _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 C4 C 0.364(2) -0.1102(17) 0.3888(16) 0.034(4) Uani 0.71(4) 1 d PDU A 1 H4A H 0.4304 -0.1505 0.3552 0.051 Uiso 0.71(4) 1 calc PR A 1 H4B H 0.2702 -0.1439 0.3451 0.051 Uiso 0.71(4) 1 calc PR A 1 H4C H 0.3874 -0.1522 0.4633 0.051 Uiso 0.71(4) 1 calc PR A 1 C4' C 0.437(5) -0.085(4) 0.434(4) 0.035(7) Uani 0.29(4) 1 d PDU A 2 H4'1 H 0.4969 -0.1162 0.3925 0.053 Uiso 0.29(4) 1 calc PR A 2 H4'2 H 0.3663 -0.1671 0.4268 0.053 Uiso 0.29(4) 1 calc PR A 2 H4'3 H 0.4924 -0.0726 0.5116 0.053 Uiso 0.29(4) 1 calc PR A 2 C1 C 0.3703(14) 0.0610(15) 0.3927(9) 0.041(2) Uani 1 1 d DU . . H1 H 0.4673 0.0935 0.4353 0.050 Uiso 1 1 calc R A 1 C2 C 0.2719(13) 0.1401(12) 0.4437(9) 0.031(2) Uani 1 1 d U A . C3 C 0.1839(14) 0.1630(12) 0.5908(10) 0.032(3) Uani 1 1 d U A . H3A H 0.1845 0.1026 0.6556 0.048 Uiso 1 1 calc R . . H3B H 0.0881 0.1773 0.5422 0.048 Uiso 1 1 calc R . . H3C H 0.2267 0.2667 0.6135 0.048 Uiso 1 1 calc R . . Cl1 Cl 0.1360(3) 0.5520(3) 0.2704(3) 0.0400(7) Uani 1 1 d . . . Cl4 Cl 0.0370(3) 0.2137(3) 0.1527(2) 0.0363(7) Uani 1 1 d . . . Cl2 Cl 0.2925(3) 0.3796(4) 0.0921(2) 0.0356(6) Uani 1 1 d . . . Cl3 Cl 0.4581(3) 0.4486(4) 0.3557(2) 0.0433(8) Uani 1 1 d . . . O1 O 0.3319(8) 0.1335(8) 0.2877(5) 0.0255(15) Uani 1 1 d U A . O2 O 0.2164(7) 0.2624(9) 0.4034(6) 0.0242(15) Uani 1 1 d U . . O3 O 0.2622(8) 0.0766(8) 0.5325(5) 0.0337(17) Uani 1 1 d U . . W1 W 0.25078(5) 0.32709(4) 0.25035(4) 0.02224(12) Uani 1 1 d . A . 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 C4 0.044(8) 0.033(7) 0.026(7) 0.009(5) 0.014(6) 0.009(6) C4' 0.038(10) 0.040(10) 0.029(10) 0.005(8) 0.012(7) 0.004(8) C1 0.055(5) 0.045(5) 0.018(4) 0.002(4) 0.003(4) 0.011(5) C2 0.047(5) 0.027(4) 0.014(4) 0.001(3) 0.005(4) 0.007(4) C3 0.041(7) 0.031(6) 0.027(6) 0.004(5) 0.016(5) 0.005(5) Cl1 0.0566(19) 0.0297(14) 0.0483(18) 0.0113(13) 0.0367(16) 0.0133(13) Cl4 0.0266(15) 0.0439(16) 0.0329(16) 0.0081(13) 0.0027(12) -0.0032(12) Cl2 0.0434(18) 0.0421(16) 0.0263(15) -0.0001(13) 0.0182(13) -0.0021(14) Cl3 0.0433(18) 0.0531(19) 0.0307(16) -0.0006(14) 0.0087(13) -0.0192(15) O1 0.033(4) 0.031(4) 0.011(3) 0.000(3) 0.004(3) 0.007(3) O2 0.030(4) 0.022(4) 0.021(4) 0.006(3) 0.008(3) 0.000(3) O3 0.053(5) 0.030(4) 0.016(4) 0.005(3) 0.010(3) 0.007(3) W1 0.02297(19) 0.02568(18) 0.01980(18) 0.0019(2) 0.00946(13) 0.0018(3) _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 C4 C1 1.448(18) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C4' C1 1.43(2) . ? C4' H4'1 0.9800 . ? C4' H4'2 0.9800 . ? C4' H4'3 0.9800 . ? C1 O1 1.421(13) . ? C1 C2 1.529(16) . ? C1 H1 1.0000 . ? C2 O2 1.210(12) . ? C2 O3 1.302(12) . ? C3 O3 1.464(13) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? Cl1 W1 2.292(3) . ? Cl4 W1 2.336(3) . ? Cl2 W1 2.271(3) . ? Cl3 W1 2.342(3) . ? O1 W1 1.824(7) . ? O2 W1 2.194(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 C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C1 C4' H4'1 109.5 . . ? C1 C4' H4'2 109.5 . . ? H4'1 C4' H4'2 109.5 . . ? C1 C4' H4'3 109.5 . . ? H4'1 C4' H4'3 109.5 . . ? H4'2 C4' H4'3 109.5 . . ? O1 C1 C4' 133(2) . . ? O1 C1 C4 113.7(11) . . ? C4' C1 C4 33(2) . . ? O1 C1 C2 102.3(9) . . ? C4' C1 C2 121.0(19) . . ? C4 C1 C2 115.1(12) . . ? O1 C1 H1 108.5 . . ? C4' C1 H1 76.6 . . ? C4 C1 H1 108.5 . . ? C2 C1 H1 108.5 . . ? O2 C2 O3 124.7(10) . . ? O2 C2 C1 117.9(9) . . ? O3 C2 C1 117.2(9) . . ? O3 C3 H3A 109.5 . . ? O3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? O3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 O1 W1 126.6(6) . . ? C2 O2 W1 114.1(6) . . ? C2 O3 C3 117.7(8) . . ? O1 W1 O2 74.5(3) . . ? O1 W1 Cl2 102.0(2) . . ? O2 W1 Cl2 176.5(2) . . ? O1 W1 Cl1 156.5(2) . . ? O2 W1 Cl1 82.1(2) . . ? Cl2 W1 Cl1 101.39(11) . . ? O1 W1 Cl4 92.1(2) . . ? O2 W1 Cl4 89.1(2) . . ? Cl2 W1 Cl4 90.87(11) . . ? Cl1 W1 Cl4 88.78(12) . . ? O1 W1 Cl3 89.7(2) . . ? O2 W1 Cl3 88.3(2) . . ? Cl2 W1 Cl3 91.94(11) . . ? Cl1 W1 Cl3 88.25(12) . . ? Cl4 W1 Cl3 176.26(11) . . ? 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 C1 C2 O2 -18.1(14) . . . . ? C4' C1 C2 O2 -178(3) . . . . ? C4 C1 C2 O2 -142.0(14) . . . . ? O1 C1 C2 O3 166.8(10) . . . . ? C4' C1 C2 O3 7(3) . . . . ? C4 C1 C2 O3 43.0(18) . . . . ? C4' C1 O1 W1 -178(3) . . . . ? C4 C1 O1 W1 149.8(12) . . . . ? C2 C1 O1 W1 25.1(13) . . . . ? O3 C2 O2 W1 -177.9(9) . . . . ? C1 C2 O2 W1 7.5(13) . . . . ? O2 C2 O3 C3 -3.0(17) . . . . ? C1 C2 O3 C3 171.7(10) . . . . ? C1 O1 W1 O2 -18.1(9) . . . . ? C1 O1 W1 Cl2 162.1(9) . . . . ? C1 O1 W1 Cl1 -14.8(13) . . . . ? C1 O1 W1 Cl4 -106.6(9) . . . . ? C1 O1 W1 Cl3 70.1(9) . . . . ? C2 O2 W1 O1 4.5(8) . . . . ? C2 O2 W1 Cl2 8(4) . . . . ? C2 O2 W1 Cl1 -174.2(8) . . . . ? C2 O2 W1 Cl4 96.9(8) . . . . ? C2 O2 W1 Cl3 -85.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.693 _refine_diff_density_min -1.726 _refine_diff_density_rms 0.183 data_fm2605b9_C2C _database_code_depnum_ccdc_archive 'CCDC 893976' #TrackingRef 'fm2605b9_C2C.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H5 Cl4 O3 W' _chemical_formula_weight 414.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 18.305(4) _cell_length_b 9.7756(19) _cell_length_c 12.088(2) _cell_angle_alpha 90.00 _cell_angle_beta 120.147(2) _cell_angle_gamma 90.00 _cell_volume 1870.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5026 _cell_measurement_theta_min 2.4485 _cell_measurement_theta_max 28.407 _exptl_crystal_description cube _exptl_crystal_colour red _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.945 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 13.450 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2221 _exptl_absorpt_correction_T_max 0.2547 _exptl_absorpt_process_details ? _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 graphite _diffrn_measurement_device_type 'CCD area detector' _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 7541 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2039 _reflns_number_gt 1979 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0111P)^2^+34.1802P] 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 2039 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0291 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0616 _refine_ls_wR_factor_gt 0.0613 _refine_ls_goodness_of_fit_ref 1.244 _refine_ls_restrained_S_all 1.244 _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 C1 C 0.3143(4) 0.2051(7) 0.2169(6) 0.0252(13) Uani 1 1 d . . . H1A H 0.3454 0.2668 0.1900 0.030 Uiso 1 1 calc R . . H1B H 0.3449 0.1170 0.2448 0.030 Uiso 1 1 calc R . . C2 C 0.3059(4) 0.2684(6) 0.3229(6) 0.0207(12) Uani 1 1 d . . . C3 C 0.3681(4) 0.3408(7) 0.5371(6) 0.0266(14) Uani 1 1 d . . . H3A H 0.4243 0.3450 0.6137 0.040 Uiso 1 1 calc R . . H3B H 0.3310 0.2835 0.5544 0.040 Uiso 1 1 calc R . . H3C H 0.3444 0.4332 0.5141 0.040 Uiso 1 1 calc R . . Cl1 Cl 0.05506(10) 0.39424(15) 0.15898(17) 0.0272(3) Uani 1 1 d . . . Cl2 Cl 0.04523(12) 0.2154(2) -0.0977(2) 0.0429(4) Uani 1 1 d . . . Cl3 Cl 0.17656(10) 0.46972(15) 0.04475(15) 0.0237(3) Uani 1 1 d . . . Cl4 Cl 0.09852(10) 0.07128(15) 0.17467(15) 0.0246(3) Uani 1 1 d . . . O1 O 0.2303(3) 0.1844(4) 0.1149(4) 0.0244(9) Uani 1 1 d . . . O2 O 0.2349(2) 0.3041(4) 0.3002(4) 0.0184(8) Uani 1 1 d . . . O3 O 0.3747(3) 0.2819(4) 0.4312(4) 0.0234(9) Uani 1 1 d . . . W1 W 0.134588(16) 0.26539(2) 0.10061(3) 0.02179(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 C1 0.025(3) 0.027(3) 0.035(4) 0.003(3) 0.023(3) 0.006(3) C2 0.018(3) 0.013(3) 0.033(3) 0.007(2) 0.014(3) 0.001(2) C3 0.022(3) 0.032(3) 0.029(3) 0.000(3) 0.015(3) -0.001(3) Cl1 0.0254(7) 0.0199(7) 0.0489(10) -0.0040(6) 0.0280(7) -0.0002(6) Cl2 0.0366(10) 0.0517(11) 0.0480(11) -0.0089(9) 0.0268(9) -0.0081(8) Cl3 0.0264(7) 0.0201(7) 0.0317(8) 0.0018(6) 0.0198(7) -0.0011(6) Cl4 0.0276(8) 0.0172(7) 0.0354(8) -0.0028(6) 0.0205(7) -0.0035(6) O1 0.025(2) 0.019(2) 0.039(3) -0.0013(19) 0.024(2) 0.0020(17) O2 0.018(2) 0.020(2) 0.023(2) -0.0025(16) 0.0147(18) -0.0010(16) O3 0.019(2) 0.024(2) 0.033(2) 0.0063(18) 0.017(2) 0.0045(17) W1 0.02226(14) 0.01606(13) 0.03662(15) -0.00223(10) 0.02190(11) -0.00033(9) _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 C1 O1 1.422(8) . ? C1 C2 1.499(9) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O2 1.236(7) . ? C2 O3 1.289(8) . ? C3 O3 1.464(8) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? Cl1 W1 2.2881(14) . ? Cl2 W1 2.173(2) . ? Cl3 W1 2.3574(15) . ? Cl4 W1 2.3306(15) . ? O1 W1 1.849(4) . ? O2 W1 2.211(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 O1 C1 C2 105.6(5) . . ? O1 C1 H1A 110.6 . . ? C2 C1 H1A 110.6 . . ? O1 C1 H1B 110.6 . . ? C2 C1 H1B 110.6 . . ? H1A C1 H1B 108.7 . . ? O2 C2 O3 125.4(6) . . ? O2 C2 C1 118.3(6) . . ? O3 C2 C1 116.3(5) . . ? O3 C3 H3A 109.5 . . ? O3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? O3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 O1 W1 125.5(4) . . ? C2 O2 W1 113.5(4) . . ? C2 O3 C3 117.4(5) . . ? O1 W1 Cl2 99.20(15) . . ? O1 W1 O2 75.09(17) . . ? Cl2 W1 O2 174.27(11) . . ? O1 W1 Cl1 157.86(15) . . ? Cl2 W1 Cl1 102.75(7) . . ? O2 W1 Cl1 82.97(11) . . ? O1 W1 Cl4 93.04(14) . . ? Cl2 W1 Cl4 92.25(7) . . ? O2 W1 Cl4 87.74(11) . . ? Cl1 W1 Cl4 89.02(5) . . ? O1 W1 Cl3 87.72(14) . . ? Cl2 W1 Cl3 92.72(7) . . ? O2 W1 Cl3 87.47(11) . . ? Cl1 W1 Cl3 88.35(5) . . ? Cl4 W1 Cl3 174.78(6) . . ? 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 C1 C2 O2 -8.2(7) . . . . ? O1 C1 C2 O3 172.3(5) . . . . ? C2 C1 O1 W1 16.3(7) . . . . ? O3 C2 O2 W1 179.0(4) . . . . ? C1 C2 O2 W1 -0.5(6) . . . . ? O2 C2 O3 C3 1.8(8) . . . . ? C1 C2 O3 C3 -178.8(5) . . . . ? C1 O1 W1 Cl2 167.0(4) . . . . ? C1 O1 W1 O2 -13.4(4) . . . . ? C1 O1 W1 Cl1 -5.3(7) . . . . ? C1 O1 W1 Cl4 -100.2(5) . . . . ? C1 O1 W1 Cl3 74.6(5) . . . . ? C2 O2 W1 O1 6.9(4) . . . . ? C2 O2 W1 Cl2 10.7(14) . . . . ? C2 O2 W1 Cl1 -170.0(4) . . . . ? C2 O2 W1 Cl4 100.7(4) . . . . ? C2 O2 W1 Cl3 -81.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.291 _refine_diff_density_min -2.059 _refine_diff_density_rms 0.168 data_fm020811_PNMA _database_code_depnum_ccdc_archive 'CCDC 893977' #TrackingRef 'fm020811_PNMA.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 Cl4 O2 W' _chemical_formula_weight 461.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 20.190(14) _cell_length_b 7.212(5) _cell_length_c 8.608(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1253.5(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1952 _cell_measurement_theta_min 2.572 _cell_measurement_theta_max 26.3765 _exptl_crystal_description plate _exptl_crystal_colour pale-green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 10.043 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2651 _exptl_absorpt_correction_T_max 0.3787 _exptl_absorpt_process_details ? _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 graphite _diffrn_measurement_device_type 'CCD area detecor' _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 8205 _diffrn_reflns_av_R_equivalents 0.0834 _diffrn_reflns_av_sigmaI/netI 0.0686 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1330 _reflns_number_gt 1117 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^+0.2126P] 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 1330 _refine_ls_number_parameters 86 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0812 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 C1 C 0.3569(5) 0.2500 1.0173(11) 0.029(2) Uani 1 2 d S . . H1A H 0.3173 0.2997 0.9666 0.044 Uiso 0.50 1 calc PR . . H1B H 0.3683 0.3274 1.1070 0.044 Uiso 0.50 1 calc PR . . H1C H 0.3483 0.1229 1.0521 0.044 Uiso 0.50 1 calc PR . . C2 C 0.4133(5) 0.2500 0.9048(9) 0.0198(19) Uani 1 2 d S . . C3 C 0.4822(5) 0.2500 0.9580(11) 0.026(2) Uani 1 2 d S . . C4 C 0.5315(5) 0.2500 0.8447(10) 0.030(2) Uani 1 2 d S . . H4 H 0.5201 0.2500 0.7376 0.036 Uiso 1 2 calc SR . . C5 C 0.5968(6) 0.2500 0.8898(12) 0.035(2) Uani 1 2 d S . . H5 H 0.6307 0.2500 0.8132 0.042 Uiso 1 2 calc SR . . C6 C 0.6137(6) 0.2500 1.0437(11) 0.035(2) Uani 1 2 d S . . H6 H 0.6589 0.2500 1.0739 0.042 Uiso 1 2 calc SR . . C7 C 0.5654(5) 0.2500 1.1522(11) 0.031(2) Uani 1 2 d S . . H7 H 0.5774 0.2500 1.2589 0.037 Uiso 1 2 calc SR . . C8 C 0.4981(6) 0.2500 1.1118(10) 0.030(2) Uani 1 2 d S . . H8 H 0.4646 0.2500 1.1894 0.036 Uiso 1 2 calc SR . . Cl1 Cl 0.27980(10) 0.0258(3) 0.6820(2) 0.0412(5) Uani 1 1 d . . . Cl2 Cl 0.41230(11) 0.0265(3) 0.47414(19) 0.0425(5) Uani 1 1 d . . . O1 O 0.2920(4) 0.2500 0.3903(7) 0.0349(17) Uani 1 2 d S . . O2 O 0.4018(3) 0.2500 0.7624(6) 0.0253(15) Uani 1 2 d S . . W1 W 0.338397(19) 0.2500 0.55210(4) 0.02250(16) Uani 1 2 d S . . 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 C1 0.033(6) 0.037(6) 0.019(4) 0.000 0.004(4) 0.000 C2 0.027(5) 0.018(4) 0.015(4) 0.000 -0.001(4) 0.000 C3 0.015(5) 0.020(4) 0.045(6) 0.000 -0.002(4) 0.000 C4 0.047(7) 0.028(5) 0.014(4) 0.000 0.005(4) 0.000 C5 0.040(7) 0.032(5) 0.032(5) 0.000 0.000(5) 0.000 C6 0.043(7) 0.027(5) 0.035(6) 0.000 -0.013(5) 0.000 C7 0.041(7) 0.030(5) 0.022(5) 0.000 -0.020(5) 0.000 C8 0.052(7) 0.020(5) 0.018(4) 0.000 -0.004(4) 0.000 Cl1 0.0435(12) 0.0453(11) 0.0350(9) 0.0090(8) -0.0051(8) -0.0169(9) Cl2 0.0573(14) 0.0453(11) 0.0249(9) -0.0052(7) 0.0027(8) 0.0183(10) O1 0.036(5) 0.046(4) 0.024(3) 0.000 -0.009(3) 0.000 O2 0.023(4) 0.037(4) 0.016(3) 0.000 0.000(3) 0.000 W1 0.0272(3) 0.0252(2) 0.0151(2) 0.000 -0.00396(15) 0.000 _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 C1 C2 1.494(12) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O2 1.247(9) . ? C2 C3 1.465(13) . ? C3 C8 1.363(13) . ? C3 C4 1.393(13) . ? C4 C5 1.375(14) . ? C4 H4 0.9500 . ? C5 C6 1.368(14) . ? C5 H5 0.9500 . ? C6 C7 1.349(15) . ? C6 H6 0.9500 . ? C7 C8 1.403(14) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? Cl1 W1 2.295(2) . ? Cl2 W1 2.297(2) . ? O1 W1 1.679(7) . ? O2 W1 2.217(6) . ? W1 Cl1 2.295(2) 7_565 ? W1 Cl2 2.297(2) 7_565 ? 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C3 119.0(8) . . ? O2 C2 C1 119.7(8) . . ? C3 C2 C1 121.4(8) . . ? C8 C3 C4 120.8(9) . . ? C8 C3 C2 121.8(9) . . ? C4 C3 C2 117.3(9) . . ? C5 C4 C3 119.1(9) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C6 C5 C4 120.8(10) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C7 C6 C5 119.4(11) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 121.9(9) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C3 C8 C7 118.0(10) . . ? C3 C8 H8 121.0 . . ? C7 C8 H8 121.0 . . ? C2 O2 W1 155.5(6) . . ? O1 W1 O2 178.7(3) . . ? O1 W1 Cl1 96.68(19) . 7_565 ? O2 W1 Cl1 84.23(13) . 7_565 ? O1 W1 Cl1 96.68(19) . . ? O2 W1 Cl1 84.23(13) . . ? Cl1 W1 Cl1 89.61(11) 7_565 . ? O1 W1 Cl2 96.92(19) . 7_565 ? O2 W1 Cl2 82.16(13) . 7_565 ? Cl1 W1 Cl2 89.01(9) 7_565 7_565 ? Cl1 W1 Cl2 166.39(7) . 7_565 ? O1 W1 Cl2 96.92(19) . . ? O2 W1 Cl2 82.16(13) . . ? Cl1 W1 Cl2 166.39(7) 7_565 . ? Cl1 W1 Cl2 89.01(9) . . ? Cl2 W1 Cl2 89.16(12) 7_565 . ? 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 O2 C2 C3 C8 180.000(2) . . . . ? C1 C2 C3 C8 0.000(3) . . . . ? O2 C2 C3 C4 0.000(3) . . . . ? C1 C2 C3 C4 180.000(2) . . . . ? C8 C3 C4 C5 0.000(3) . . . . ? C2 C3 C4 C5 180.000(2) . . . . ? C3 C4 C5 C6 0.000(3) . . . . ? C4 C5 C6 C7 0.000(3) . . . . ? C5 C6 C7 C8 0.000(3) . . . . ? C4 C3 C8 C7 0.000(3) . . . . ? C2 C3 C8 C7 180.000(2) . . . . ? C6 C7 C8 C3 0.000(3) . . . . ? C3 C2 O2 W1 180.000(2) . . . . ? C1 C2 O2 W1 0.000(3) . . . . ? C2 O2 W1 O1 180.000(16) . . . . ? C2 O2 W1 Cl1 45.10(6) . . . 7_565 ? C2 O2 W1 Cl1 -45.10(6) . . . . ? C2 O2 W1 Cl2 134.88(6) . . . 7_565 ? C2 O2 W1 Cl2 -134.88(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.017 _refine_diff_density_min -1.390 _refine_diff_density_rms 0.203 data_fm100511_P21N _database_code_depnum_ccdc_archive 'CCDC 893978' #TrackingRef 'fm100511_P21N.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 Cl6 N2 O W' _chemical_formula_weight 649.87 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 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 14.390(10) _cell_length_b 9.985(7) _cell_length_c 16.622(11) _cell_angle_alpha 90.00 _cell_angle_beta 110.196(9) _cell_angle_gamma 90.00 _cell_volume 2241(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1133 _cell_measurement_theta_min 2.3105 _cell_measurement_theta_max 22.1675 _exptl_crystal_description needle _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.926 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_absorpt_coefficient_mu 5.877 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4014 _exptl_absorpt_correction_T_max 0.5641 _exptl_absorpt_process_details ? _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 graphite _diffrn_measurement_device_type 'CCD area detector' _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 11489 _diffrn_reflns_av_R_equivalents 0.1656 _diffrn_reflns_av_sigmaI/netI 0.2029 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3877 _reflns_number_gt 1904 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0831P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3877 _refine_ls_number_parameters 238 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.1739 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.1873 _refine_ls_wR_factor_gt 0.1478 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.947 _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 0.87998(6) 0.36703(6) 0.12652(6) 0.0368(3) Uani 1 1 d . . . Cl1 Cl 0.7496(4) 0.2823(5) 0.0100(3) 0.0539(15) Uani 1 1 d . . . Cl2 Cl 0.9871(4) 0.2443(4) 0.0798(4) 0.0528(15) Uani 1 1 d . . . Cl3 Cl 0.8657(4) 0.1856(4) 0.2107(3) 0.0434(13) Uani 1 1 d . . . Cl4 Cl 1.0125(4) 0.4552(5) 0.2355(3) 0.0508(14) Uani 1 1 d . . . Cl5 Cl 0.7672(4) 0.4799(4) 0.1718(4) 0.0484(14) Uani 1 1 d . . . Cl6 Cl 0.8925(4) 0.5486(4) 0.0417(4) 0.0476(14) Uani 1 1 d . . . C1 C 0.7147(13) 0.9702(17) -0.0965(12) 0.042(5) Uani 1 1 d U . . H1A H 0.6601 0.9442 -0.0773 0.063 Uiso 1 1 calc R . . H1B H 0.7126 0.9157 -0.1461 0.063 Uiso 1 1 calc R . . H1C H 0.7082 1.0650 -0.1127 0.063 Uiso 1 1 calc R . . C2 C 0.8121(14) 0.9480(15) -0.0248(13) 0.036(4) Uani 1 1 d U . . O1 O 0.8902(9) 0.9740(11) -0.0341(8) 0.038(3) Uani 1 1 d . . . C3 C 0.8894(12) 0.8674(15) 0.1214(11) 0.029(4) Uani 1 1 d U . . C4 C 0.8829(13) 0.8140(15) 0.2007(12) 0.037(5) Uani 1 1 d U . . H4A H 0.8133 0.7974 0.1935 0.056 Uiso 1 1 calc R . . H4B H 0.9109 0.8787 0.2471 0.056 Uiso 1 1 calc R . . H4C H 0.9200 0.7298 0.2150 0.056 Uiso 1 1 calc R . . C5 C 0.7117(14) 0.8598(18) 0.0560(13) 0.044(4) Uani 1 1 d U . . C6 C 0.6685(15) 0.7360(18) 0.0235(13) 0.047(4) Uani 1 1 d U . . H6 H 0.7010 0.6727 -0.0004 0.056 Uiso 1 1 calc R . . C7 C 0.5746(15) 0.712(2) 0.0283(14) 0.059(4) Uani 1 1 d U . . H7 H 0.5428 0.6288 0.0074 0.070 Uiso 1 1 calc R . . C8 C 0.5271(16) 0.803(2) 0.0619(14) 0.060(4) Uani 1 1 d U . . H8 H 0.4635 0.7808 0.0634 0.072 Uiso 1 1 calc R . . C9 C 0.6634(14) 0.9544(18) 0.0883(13) 0.044(4) Uani 1 1 d U . . H9 H 0.6935 1.0388 0.1071 0.053 Uiso 1 1 calc R . . C10 C 1.0709(13) 0.8815(14) 0.1911(12) 0.035(3) Uani 1 1 d U . . C11 C 1.1379(14) 0.7844(17) 0.1850(12) 0.042(4) Uani 1 1 d U . . H11 H 1.1209 0.7225 0.1388 0.050 Uiso 1 1 calc R . . C12 C 1.2321(14) 0.7821(17) 0.2504(12) 0.044(4) Uani 1 1 d U . . H12 H 1.2803 0.7209 0.2454 0.052 Uiso 1 1 calc R . . C13 C 1.2565(14) 0.8633(16) 0.3199(13) 0.045(4) Uani 1 1 d U . . H13 H 1.3191 0.8575 0.3645 0.054 Uiso 1 1 calc R . . C14 C 1.1840(14) 0.9572(16) 0.3226(13) 0.044(4) Uani 1 1 d U . . H14 H 1.1988 1.0175 0.3696 0.053 Uiso 1 1 calc R . . C15 C 1.0930(14) 0.9635(16) 0.2589(13) 0.041(4) Uani 1 1 d U . . H15 H 1.0453 1.0265 0.2630 0.049 Uiso 1 1 calc R . . C16 C 0.5676(15) 0.924(2) 0.0934(14) 0.056(4) Uani 1 1 d U . . H16 H 0.5341 0.9861 0.1175 0.067 Uiso 1 1 calc R . . N1 N 0.8076(10) 0.8927(11) 0.0515(9) 0.025(3) Uani 1 1 d . . . N2 N 0.9779(11) 0.8963(11) 0.1202(9) 0.031(4) Uani 1 1 d D . . H2 H 0.987(13) 0.921(16) 0.074(6) 0.037 Uiso 1 1 d 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 W1 0.0413(5) 0.0183(3) 0.0558(6) -0.0016(4) 0.0230(4) -0.0026(3) Cl1 0.063(4) 0.041(2) 0.050(4) 0.005(2) 0.009(3) -0.015(2) Cl2 0.060(4) 0.029(2) 0.084(5) -0.004(2) 0.044(3) 0.002(2) Cl3 0.056(3) 0.0227(19) 0.058(4) 0.006(2) 0.028(3) 0.0037(19) Cl4 0.052(3) 0.048(3) 0.054(4) -0.008(2) 0.020(3) -0.012(2) Cl5 0.052(3) 0.024(2) 0.086(4) 0.008(2) 0.045(3) 0.0036(19) Cl6 0.053(3) 0.027(2) 0.073(4) 0.005(2) 0.034(3) -0.0021(19) C1 0.035(10) 0.037(9) 0.064(13) 0.012(9) 0.028(9) -0.007(7) C2 0.035(10) 0.022(8) 0.069(13) -0.003(8) 0.042(10) 0.004(7) O1 0.030(8) 0.043(7) 0.048(9) 0.004(6) 0.021(7) -0.002(5) C3 0.025(9) 0.026(7) 0.035(10) 0.011(8) 0.010(8) -0.010(8) C4 0.039(10) 0.019(7) 0.055(12) 0.002(8) 0.017(9) -0.005(7) C5 0.040(8) 0.043(7) 0.052(8) 0.005(7) 0.020(7) 0.002(6) C6 0.044(8) 0.042(7) 0.057(8) 0.008(7) 0.020(7) -0.008(6) C7 0.049(8) 0.057(8) 0.067(9) 0.008(7) 0.017(8) -0.015(7) C8 0.047(9) 0.066(8) 0.068(9) 0.008(8) 0.021(8) -0.004(7) C9 0.041(8) 0.050(7) 0.052(8) 0.006(7) 0.028(7) 0.003(6) C10 0.037(7) 0.021(6) 0.049(8) 0.001(6) 0.019(7) 0.006(6) C11 0.047(8) 0.033(6) 0.050(8) 0.004(6) 0.023(7) 0.012(6) C12 0.048(8) 0.037(6) 0.053(9) 0.007(6) 0.027(7) 0.013(6) C13 0.051(8) 0.032(6) 0.056(8) 0.002(6) 0.026(7) 0.004(6) C14 0.043(8) 0.030(6) 0.062(9) -0.003(6) 0.023(7) -0.001(6) C15 0.038(7) 0.030(6) 0.059(9) -0.005(6) 0.023(7) 0.006(6) C16 0.044(8) 0.065(8) 0.064(9) 0.006(7) 0.024(7) 0.003(7) N1 0.030(8) 0.016(6) 0.035(9) 0.004(6) 0.020(7) 0.002(5) N2 0.045(10) 0.011(6) 0.033(10) -0.003(6) 0.009(8) 0.008(6) _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 Cl2 2.304(5) . ? W1 Cl4 2.304(5) . ? W1 Cl5 2.305(5) . ? W1 Cl1 2.340(5) . ? W1 Cl6 2.341(5) . ? W1 Cl3 2.342(5) . ? C1 C2 1.51(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O1 1.214(19) . ? C2 N1 1.41(2) . ? C3 N2 1.31(2) . ? C3 N1 1.36(2) . ? C3 C4 1.45(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C9 1.39(3) . ? C5 C6 1.41(2) . ? C5 N1 1.44(2) . ? C6 C7 1.40(3) . ? C6 H6 0.9500 . ? C7 C8 1.37(3) . ? C7 H7 0.9500 . ? C8 C16 1.37(3) . ? C8 H8 0.9500 . ? C9 C16 1.44(3) . ? C9 H9 0.9500 . ? C10 C15 1.34(2) . ? C10 C11 1.40(2) . ? C10 N2 1.45(2) . ? C11 C12 1.42(2) . ? C11 H11 0.9500 . ? C12 C13 1.35(2) . ? C12 H12 0.9500 . ? C13 C14 1.41(2) . ? C13 H13 0.9500 . ? C14 C15 1.37(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N2 H2 0.87(2) . ? 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 Cl2 W1 Cl4 90.0(2) . . ? Cl2 W1 Cl5 176.90(16) . . ? Cl4 W1 Cl5 92.38(19) . . ? Cl2 W1 Cl1 88.1(2) . . ? Cl4 W1 Cl1 176.56(19) . . ? Cl5 W1 Cl1 89.6(2) . . ? Cl2 W1 Cl6 90.54(18) . . ? Cl4 W1 Cl6 87.86(19) . . ? Cl5 W1 Cl6 91.57(17) . . ? Cl1 W1 Cl6 89.28(18) . . ? Cl2 W1 Cl3 89.82(17) . . ? Cl4 W1 Cl3 92.60(18) . . ? Cl5 W1 Cl3 88.05(16) . . ? Cl1 W1 Cl3 90.27(17) . . ? Cl6 W1 Cl3 179.41(18) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 N1 122.2(18) . . ? O1 C2 C1 121.0(18) . . ? N1 C2 C1 116.8(15) . . ? N2 C3 N1 120.3(15) . . ? N2 C3 C4 117.4(15) . . ? N1 C3 C4 122.2(15) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C9 C5 C6 122.3(19) . . ? C9 C5 N1 118.7(16) . . ? C6 C5 N1 118.9(17) . . ? C7 C6 C5 116.0(19) . . ? C7 C6 H6 122.0 . . ? C5 C6 H6 122.0 . . ? C8 C7 C6 122(2) . . ? C8 C7 H7 118.8 . . ? C6 C7 H7 118.8 . . ? C7 C8 C16 123(2) . . ? C7 C8 H8 118.7 . . ? C16 C8 H8 118.7 . . ? C5 C9 C16 120.0(18) . . ? C5 C9 H9 120.0 . . ? C16 C9 H9 120.0 . . ? C15 C10 C11 121.1(17) . . ? C15 C10 N2 120.3(15) . . ? C11 C10 N2 118.5(15) . . ? C10 C11 C12 117.2(17) . . ? C10 C11 H11 121.4 . . ? C12 C11 H11 121.4 . . ? C13 C12 C11 122.9(17) . . ? C13 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? C12 C13 C14 116.5(18) . . ? C12 C13 H13 121.8 . . ? C14 C13 H13 121.8 . . ? C15 C14 C13 121.6(18) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C10 C15 C14 120.5(17) . . ? C10 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C8 C16 C9 117(2) . . ? C8 C16 H16 121.6 . . ? C9 C16 H16 121.6 . . ? C3 N1 C2 123.1(14) . . ? C3 N1 C5 118.3(14) . . ? C2 N1 C5 118.6(14) . . ? C3 N2 C10 126.3(15) . . ? C3 N2 H2 122(10) . . ? C10 N2 H2 112(10) . . ? 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 C9 C5 C6 C7 -2(3) . . . . ? N1 C5 C6 C7 -178.7(17) . . . . ? C5 C6 C7 C8 1(3) . . . . ? C6 C7 C8 C16 0(3) . . . . ? C6 C5 C9 C16 3(3) . . . . ? N1 C5 C9 C16 179.9(16) . . . . ? C15 C10 C11 C12 -4(3) . . . . ? N2 C10 C11 C12 173.1(16) . . . . ? C10 C11 C12 C13 4(3) . . . . ? C11 C12 C13 C14 -3(3) . . . . ? C12 C13 C14 C15 1(3) . . . . ? C11 C10 C15 C14 3(3) . . . . ? N2 C10 C15 C14 -174.5(16) . . . . ? C13 C14 C15 C10 -1(3) . . . . ? C7 C8 C16 C9 1(3) . . . . ? C5 C9 C16 C8 -3(3) . . . . ? N2 C3 N1 C2 1(2) . . . . ? C4 C3 N1 C2 178.1(14) . . . . ? N2 C3 N1 C5 -179.6(14) . . . . ? C4 C3 N1 C5 -3(2) . . . . ? O1 C2 N1 C3 2(2) . . . . ? C1 C2 N1 C3 -180.0(14) . . . . ? O1 C2 N1 C5 -177.6(14) . . . . ? C1 C2 N1 C5 1(2) . . . . ? C9 C5 N1 C3 88(2) . . . . ? C6 C5 N1 C3 -95(2) . . . . ? C9 C5 N1 C2 -93(2) . . . . ? C6 C5 N1 C2 84(2) . . . . ? N1 C3 N2 C10 176.5(13) . . . . ? C4 C3 N2 C10 -1(2) . . . . ? C15 C10 N2 C3 -71(2) . . . . ? C11 C10 N2 C3 111.9(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.87(2) 1.92(14) 2.558(18) 129(15) . N2 H2 O1 0.87(2) 2.33(12) 3.03(2) 138(15) 3_775 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 2.301 _refine_diff_density_min -1.677 _refine_diff_density_rms 0.240 data_fm230112_PNMA _database_code_depnum_ccdc_archive 'CCDC 893979' #TrackingRef 'fm230112_PNMA.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H19 Cl6 N2 O2 W' _chemical_formula_weight 595.82 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 19.219(4) _cell_length_b 29.661(6) _cell_length_c 13.226(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7540(3) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9989 _cell_measurement_theta_min 2.228 _cell_measurement_theta_max 25.4515 _exptl_crystal_description needle _exptl_crystal_colour orange-brown _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.100 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4560 _exptl_absorpt_coefficient_mu 6.981 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3505 _exptl_absorpt_correction_T_max 0.5419 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 72771 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 25.66 _reflns_number_total 7274 _reflns_number_gt 6189 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0246P)^2^+23.1337P] 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 461 _refine_ls_number_restraints 342 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0668 _refine_ls_wR_factor_gt 0.0626 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.019 _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 0.181881(9) 0.490354(7) 0.787508(13) 0.02857(6) Uani 1 1 d . . . W2 W 0.168301(15) 0.2500 0.28167(2) 0.03439(8) Uani 1 2 d S . . W3 W 0.381645(15) 0.2500 0.81472(2) 0.02984(8) Uani 1 2 d S . . Cl1 Cl 0.13158(7) 0.48829(6) 0.62968(9) 0.0536(4) Uani 1 1 d . . . Cl2 Cl 0.27079(6) 0.53638(5) 0.72858(9) 0.0396(3) Uani 1 1 d . . . Cl3 Cl 0.24811(7) 0.42682(5) 0.74877(12) 0.0531(4) Uani 1 1 d . . . Cl4 Cl 0.22868(6) 0.49036(5) 0.94793(9) 0.0376(3) Uani 1 1 d . . . Cl5 Cl 0.09281(6) 0.44289(5) 0.84381(9) 0.0393(3) Uani 1 1 d . . . Cl6 Cl 0.11744(6) 0.55357(5) 0.83022(10) 0.0416(3) Uani 1 1 d . . . Cl7 Cl 0.27524(11) 0.2500 0.36413(16) 0.0602(6) Uani 1 2 d S . . Cl8 Cl 0.11076(10) 0.2500 0.43726(13) 0.0453(5) Uani 1 2 d S . . Cl9 Cl 0.16734(8) 0.32752(5) 0.28298(11) 0.0519(4) Uani 1 1 d . . . Cl10 Cl 0.06145(10) 0.2500 0.19838(13) 0.0421(4) Uani 1 2 d S . . Cl11 Cl 0.22492(10) 0.2500 0.12670(14) 0.0464(5) Uani 1 2 d S . . Cl12 Cl 0.50006(10) 0.2500 0.77679(16) 0.0497(5) Uani 1 2 d S . . Cl13 Cl 0.35647(9) 0.2500 0.64324(14) 0.0447(5) Uani 1 2 d S . . Cl14 Cl 0.38290(11) 0.32788(5) 0.81310(16) 0.0729(5) Uani 1 1 d . . . Cl15 Cl 0.40807(14) 0.2500 0.98518(17) 0.0744(8) Uani 1 2 d S . . Cl16 Cl 0.26412(11) 0.2500 0.85033(17) 0.0630(6) Uani 1 2 d S . . C11 C 0.1328(3) 0.37198(17) 0.5287(4) 0.0360(11) Uani 1 1 d U . . C12 C 0.0953(3) 0.3448(2) 0.6069(4) 0.0486(14) Uani 1 1 d U . . H12A H 0.0648 0.3219 0.5753 0.058 Uiso 1 1 calc R . . H12B H 0.0670 0.3643 0.6516 0.058 Uiso 1 1 calc R . . C13 C 0.1545(4) 0.3229(2) 0.6647(5) 0.0673(18) Uani 1 1 d U . . H13A H 0.1600 0.3370 0.7320 0.081 Uiso 1 1 calc R . . H13B H 0.1455 0.2903 0.6740 0.081 Uiso 1 1 calc R . . C14 C 0.2186(3) 0.3301(2) 0.6017(5) 0.0533(15) Uani 1 1 d U . . H14A H 0.2581 0.3400 0.6444 0.064 Uiso 1 1 calc R . . H14B H 0.2318 0.3020 0.5660 0.064 Uiso 1 1 calc R . . C15 C 0.2493(3) 0.3864(2) 0.4656(5) 0.0548(16) Uani 1 1 d U . . H15A H 0.2960 0.3753 0.4818 0.082 Uiso 1 1 calc R . . H15B H 0.2476 0.4191 0.4757 0.082 Uiso 1 1 calc R . . H15C H 0.2384 0.3793 0.3949 0.082 Uiso 1 1 calc R . . O1 O 0.10477(19) 0.39909(13) 0.4663(3) 0.0424(9) Uani 1 1 d U . . H1 H 0.0628 0.4029 0.4819 0.064 Uiso 1 1 calc R . . N1 N 0.1993(2) 0.36499(15) 0.5304(3) 0.0401(10) Uani 1 1 d U . . C21 C 0.4459(3) 0.37595(17) 0.0867(4) 0.0367(11) Uani 1 1 d U . . C22 C 0.4779(3) 0.3440(2) 0.1602(5) 0.0499(14) Uani 1 1 d U . . H22A H 0.5130 0.3594 0.2027 0.060 Uiso 1 1 calc R . . H22B H 0.5004 0.3184 0.1247 0.060 Uiso 1 1 calc R . . C23 C 0.4167(3) 0.3278(2) 0.2236(5) 0.0569(16) Uani 1 1 d U . . H23A H 0.4176 0.2946 0.2305 0.068 Uiso 1 1 calc R . . H23B H 0.4183 0.3415 0.2919 0.068 Uiso 1 1 calc R . . C24 C 0.3522(3) 0.3429(2) 0.1674(5) 0.0507(14) Uani 1 1 d U . . H24A H 0.3292 0.3170 0.1339 0.061 Uiso 1 1 calc R . . H24B H 0.3187 0.3575 0.2139 0.061 Uiso 1 1 calc R . . C25 C 0.3326(3) 0.4011(2) 0.0279(5) 0.0563(17) Uani 1 1 d U . . H25A H 0.2841 0.3949 0.0462 0.084 Uiso 1 1 calc R . . H25B H 0.3403 0.3926 -0.0429 0.084 Uiso 1 1 calc R . . H25C H 0.3422 0.4333 0.0365 0.084 Uiso 1 1 calc R . . O2 O 0.47851(19) 0.40137(13) 0.0255(3) 0.0442(9) Uani 1 1 d U . . N2 N 0.3787(2) 0.37510(15) 0.0927(3) 0.0363(10) Uani 1 1 d U . . C31 C 0.0673(3) 0.3715(2) 0.0427(4) 0.0505(14) Uani 1 1 d U . . C32 C 0.1449(3) 0.3783(2) 0.0420(5) 0.0581(16) Uani 1 1 d U . . H32A H 0.1652 0.3713 0.1090 0.070 Uiso 1 1 calc R . . H32B H 0.1569 0.4097 0.0236 0.070 Uiso 1 1 calc R . . C33 C 0.1709(4) 0.3454(2) -0.0378(6) 0.0670(18) Uani 1 1 d U . . H33A H 0.2119 0.3284 -0.0132 0.080 Uiso 1 1 calc R . . H33B H 0.1834 0.3613 -0.1010 0.080 Uiso 1 1 calc R . . C34 C 0.1089(4) 0.3138(2) -0.0546(6) 0.0746(19) Uani 1 1 d U . . H34A H 0.1018 0.3081 -0.1276 0.090 Uiso 1 1 calc R . . H34B H 0.1162 0.2847 -0.0197 0.090 Uiso 1 1 calc R . . C35 C -0.0186(4) 0.3201(2) -0.0248(5) 0.070(2) Uani 1 1 d U . . H35A H -0.0186 0.2934 -0.0683 0.105 Uiso 1 1 calc R . . H35B H -0.0476 0.3436 -0.0554 0.105 Uiso 1 1 calc R . . H35C H -0.0373 0.3122 0.0418 0.105 Uiso 1 1 calc R . . O3 O 0.0234(2) 0.3935(2) 0.0880(3) 0.0822(16) Uani 1 1 d U . . N3 N 0.0519(3) 0.33663(16) -0.0137(4) 0.0511(12) Uani 1 1 d U . . C41 C 0.0631(6) 0.4954(3) 0.1833(6) 0.0297(18) Uani 0.570(5) 1 d PDU A 1 C42 C 0.0506(4) 0.4710(3) 0.2809(6) 0.0327(17) Uani 0.570(5) 1 d PDU A 1 H42A H 0.0798 0.4436 0.2856 0.039 Uiso 0.570(5) 1 calc PR A 1 H42B H 0.0011 0.4623 0.2877 0.039 Uiso 0.570(5) 1 calc PR A 1 C43 C 0.0711(11) 0.5057(4) 0.3618(9) 0.034(2) Uani 0.570(5) 1 d PDU A 1 H43A H 0.1187 0.4999 0.3871 0.041 Uiso 0.570(5) 1 calc PR A 1 H43B H 0.0383 0.5048 0.4195 0.041 Uiso 0.570(5) 1 calc PR A 1 C44 C 0.0674(5) 0.5513(3) 0.3069(6) 0.0350(18) Uani 0.570(5) 1 d PDU A 1 H44A H 0.0224 0.5665 0.3199 0.042 Uiso 0.570(5) 1 calc PR A 1 H44B H 0.1057 0.5715 0.3286 0.042 Uiso 0.570(5) 1 calc PR A 1 C45 C 0.0830(5) 0.5732(4) 0.1204(7) 0.033(2) Uani 0.570(5) 1 d PDU A 1 H45A H 0.0902 0.6029 0.1510 0.050 Uiso 0.570(5) 1 calc PR A 1 H45B H 0.0412 0.5739 0.0781 0.050 Uiso 0.570(5) 1 calc PR A 1 H45C H 0.1234 0.5654 0.0788 0.050 Uiso 0.570(5) 1 calc PR A 1 O4 O 0.0622(5) 0.4795(3) 0.0939(5) 0.044(2) Uani 0.570(5) 1 d PDU A 1 H4 H 0.0610 0.4512 0.0964 0.066 Uiso 0.570(5) 1 calc PR A 1 N4 N 0.0744(4) 0.5393(3) 0.2006(5) 0.0334(17) Uani 0.570(5) 1 d PDU A 1 C51 C 0.0605(8) 0.4793(3) 0.2101(8) 0.031(2) Uani 0.430(5) 1 d PDU A 2 C52 C 0.0611(10) 0.4995(4) 0.1046(10) 0.037(3) Uani 0.430(5) 1 d PDU A 2 H52A H 0.0140 0.4991 0.0744 0.045 Uiso 0.430(5) 1 calc PR A 2 H52B H 0.0934 0.4829 0.0597 0.045 Uiso 0.430(5) 1 calc PR A 2 C53 C 0.0862(7) 0.5479(4) 0.1218(9) 0.036(2) Uani 0.430(5) 1 d PDU A 2 H53A H 0.0588 0.5695 0.0808 0.043 Uiso 0.430(5) 1 calc PR A 2 H53B H 0.1360 0.5510 0.1041 0.043 Uiso 0.430(5) 1 calc PR A 2 C54 C 0.0743(7) 0.5560(4) 0.2367(8) 0.033(2) Uani 0.430(5) 1 d PDU A 2 H54A H 0.1145 0.5719 0.2670 0.039 Uiso 0.430(5) 1 calc PR A 2 H54B H 0.0318 0.5741 0.2482 0.039 Uiso 0.430(5) 1 calc PR A 2 C55 C 0.0646(14) 0.5023(7) 0.3879(9) 0.031(4) Uani 0.430(5) 1 d PDU A 2 H55A H 0.0706 0.5305 0.4255 0.047 Uiso 0.430(5) 1 calc PR A 2 H55B H 0.1021 0.4814 0.4057 0.047 Uiso 0.430(5) 1 calc PR A 2 H55C H 0.0197 0.4888 0.4053 0.047 Uiso 0.430(5) 1 calc PR A 2 O5 O 0.0538(4) 0.4388(3) 0.2337(6) 0.034(2) Uani 0.430(5) 1 d PDU A 2 H5 H 0.0150 0.4350 0.2619 0.051 Uiso 0.430(5) 1 calc PR A 2 N5 N 0.0669(5) 0.5115(3) 0.2796(6) 0.0290(16) Uani 0.430(5) 1 d PDU 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 0.01868(10) 0.04364(13) 0.02338(10) -0.00010(8) 0.00020(7) -0.00132(8) W2 0.02900(15) 0.04724(19) 0.02692(15) 0.000 0.00520(11) 0.000 W3 0.02925(15) 0.02567(15) 0.03459(15) 0.000 -0.00074(12) 0.000 Cl1 0.0429(8) 0.0932(12) 0.0248(6) 0.0028(7) -0.0071(6) -0.0201(8) Cl2 0.0243(6) 0.0623(9) 0.0322(6) 0.0062(6) 0.0009(5) -0.0088(6) Cl3 0.0399(8) 0.0540(9) 0.0656(9) -0.0163(8) 0.0128(7) 0.0041(7) Cl4 0.0302(6) 0.0540(8) 0.0286(6) 0.0058(6) -0.0063(5) -0.0026(6) Cl5 0.0269(6) 0.0529(8) 0.0379(7) 0.0034(6) 0.0009(5) -0.0080(6) Cl6 0.0257(6) 0.0469(8) 0.0522(8) 0.0012(6) -0.0031(6) 0.0039(6) Cl7 0.0318(10) 0.1019(19) 0.0468(12) 0.000 -0.0047(9) 0.000 Cl8 0.0435(11) 0.0647(13) 0.0276(9) 0.000 0.0090(8) 0.000 Cl9 0.0476(8) 0.0468(9) 0.0614(9) -0.0062(7) 0.0163(7) -0.0097(7) Cl10 0.0345(10) 0.0588(12) 0.0329(9) 0.000 -0.0016(7) 0.000 Cl11 0.0430(11) 0.0606(13) 0.0355(10) 0.000 0.0159(8) 0.000 Cl12 0.0275(9) 0.0626(14) 0.0590(13) 0.000 -0.0069(9) 0.000 Cl13 0.0284(9) 0.0655(13) 0.0403(10) 0.000 -0.0024(8) 0.000 Cl14 0.0888(13) 0.0269(8) 0.1029(14) -0.0105(8) 0.0014(11) 0.0059(8) Cl15 0.0732(17) 0.113(2) 0.0368(11) 0.000 -0.0104(11) 0.000 Cl16 0.0361(11) 0.1017(19) 0.0513(12) 0.000 0.0133(10) 0.000 C11 0.038(3) 0.029(3) 0.040(3) -0.005(2) -0.005(2) 0.000(2) C12 0.057(3) 0.043(3) 0.046(3) -0.002(3) 0.005(3) -0.005(3) C13 0.077(4) 0.061(4) 0.064(4) 0.019(3) -0.021(3) -0.026(3) C14 0.063(4) 0.043(3) 0.054(3) -0.004(3) -0.023(3) 0.003(3) C15 0.039(3) 0.067(4) 0.058(4) 0.000(3) -0.004(3) -0.008(3) O1 0.033(2) 0.042(2) 0.053(2) 0.0030(18) -0.0088(17) 0.0004(17) N1 0.036(2) 0.041(3) 0.043(2) -0.002(2) -0.0083(19) -0.004(2) C21 0.033(3) 0.031(3) 0.046(3) 0.001(2) 0.004(2) 0.004(2) C22 0.039(3) 0.042(3) 0.068(4) 0.015(3) -0.003(3) -0.001(2) C23 0.050(3) 0.052(3) 0.068(4) 0.024(3) 0.011(3) 0.005(3) C24 0.039(3) 0.049(3) 0.063(3) 0.005(3) 0.011(3) -0.005(3) C25 0.034(3) 0.081(5) 0.054(4) 0.003(3) 0.003(3) 0.020(3) O2 0.034(2) 0.045(2) 0.054(2) 0.0084(18) 0.0074(17) 0.0066(17) N2 0.029(2) 0.042(2) 0.038(2) 0.0008(19) 0.0027(18) 0.0053(18) C31 0.056(3) 0.056(3) 0.040(3) -0.001(3) -0.009(3) 0.006(3) C32 0.051(3) 0.064(4) 0.059(4) 0.006(3) -0.006(3) 0.009(3) C33 0.060(4) 0.047(4) 0.094(4) 0.005(3) 0.010(3) 0.013(3) C34 0.078(4) 0.046(4) 0.099(5) -0.002(3) 0.022(4) 0.001(3) C35 0.072(5) 0.062(4) 0.076(5) 0.010(4) -0.013(4) -0.024(4) O3 0.043(3) 0.146(5) 0.058(3) -0.033(3) 0.003(2) 0.010(3) N3 0.059(3) 0.037(3) 0.057(3) 0.005(2) 0.005(2) -0.004(2) C41 0.016(3) 0.046(4) 0.027(4) -0.003(3) 0.000(3) 0.001(4) C42 0.025(3) 0.043(4) 0.030(4) -0.001(3) -0.002(3) -0.002(3) C43 0.029(4) 0.044(5) 0.030(5) -0.003(4) 0.002(5) -0.003(4) C44 0.029(3) 0.046(4) 0.030(4) -0.003(3) -0.001(3) -0.004(3) C45 0.012(4) 0.060(6) 0.028(4) 0.017(5) -0.003(3) -0.002(5) O4 0.032(4) 0.060(5) 0.039(4) -0.003(4) -0.005(3) -0.005(5) N4 0.020(3) 0.052(4) 0.028(4) 0.001(3) 0.001(3) 0.000(3) C51 0.019(4) 0.048(5) 0.025(4) 0.000(4) -0.001(4) 0.001(4) C52 0.027(4) 0.054(6) 0.032(5) 0.001(5) 0.000(4) 0.003(5) C53 0.018(4) 0.053(5) 0.036(5) 0.001(5) 0.001(4) 0.002(5) C54 0.022(4) 0.051(5) 0.025(5) 0.003(4) 0.004(4) 0.003(4) C55 0.032(7) 0.041(7) 0.020(7) 0.000(5) 0.000(7) 0.002(6) O5 0.026(4) 0.035(5) 0.040(5) -0.003(4) 0.002(3) -0.002(3) N5 0.021(3) 0.042(3) 0.024(3) -0.002(3) -0.001(3) -0.002(3) _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 Cl1 2.3013(13) . ? W1 Cl4 2.3046(12) . ? W1 Cl6 2.3171(14) . ? W1 Cl2 2.3219(13) . ? W1 Cl3 2.3311(15) . ? W1 Cl5 2.3383(13) . ? W2 Cl9 2.2993(16) . ? W2 Cl9 2.2993(16) 7_565 ? W2 Cl11 2.3207(18) . ? W2 Cl7 2.327(2) . ? W2 Cl10 2.3305(19) . ? W2 Cl8 2.3362(18) . ? W3 Cl16 2.307(2) . ? W3 Cl14 2.3102(16) 7_565 ? W3 Cl14 2.3102(16) . ? W3 Cl15 2.311(2) . ? W3 Cl13 2.3190(19) . ? W3 Cl12 2.330(2) . ? C11 O1 1.272(6) . ? C11 N1 1.295(7) . ? C11 C12 1.497(7) . ? C12 C13 1.517(9) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.502(9) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N1 1.449(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N1 1.435(7) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? O1 H1 0.8400 . ? C21 O2 1.271(6) . ? C21 N2 1.295(6) . ? C21 C22 1.491(7) . ? C22 C23 1.521(8) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.513(8) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 N2 1.466(7) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N2 1.455(7) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C31 O3 1.221(7) . ? C31 N3 1.310(7) . ? C31 C32 1.506(9) . ? C32 C33 1.521(9) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.531(10) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 N3 1.396(8) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 N3 1.448(8) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C41 O4 1.273(9) . ? C41 N4 1.339(10) . ? C41 C42 1.499(10) . ? C42 C43 1.536(12) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.538(12) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 N4 1.457(8) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 N4 1.471(9) . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? O4 H4 0.8400 . ? C51 O5 1.245(10) . ? C51 N5 1.334(10) . ? C51 C52 1.519(12) . ? C52 C53 1.531(13) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 C54 1.556(12) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 N5 1.442(10) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C55 N5 1.459(11) . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? O5 H5 0.8400 . ? 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 Cl1 W1 Cl4 177.59(5) . . ? Cl1 W1 Cl6 91.04(6) . . ? Cl4 W1 Cl6 89.09(5) . . ? Cl1 W1 Cl2 91.16(5) . . ? Cl4 W1 Cl2 91.25(4) . . ? Cl6 W1 Cl2 89.97(5) . . ? Cl1 W1 Cl3 90.49(6) . . ? Cl4 W1 Cl3 89.39(5) . . ? Cl6 W1 Cl3 178.47(5) . . ? Cl2 W1 Cl3 89.98(5) . . ? Cl1 W1 Cl5 88.01(5) . . ? Cl4 W1 Cl5 89.58(5) . . ? Cl6 W1 Cl5 91.05(5) . . ? Cl2 W1 Cl5 178.70(5) . . ? Cl3 W1 Cl5 89.03(5) . . ? Cl9 W2 Cl9 178.74(7) . 7_565 ? Cl9 W2 Cl11 90.60(4) . . ? Cl9 W2 Cl11 90.60(4) 7_565 . ? Cl9 W2 Cl7 90.21(4) . . ? Cl9 W2 Cl7 90.21(4) 7_565 . ? Cl11 W2 Cl7 89.99(7) . . ? Cl9 W2 Cl10 89.80(4) . . ? Cl9 W2 Cl10 89.80(4) 7_565 . ? Cl11 W2 Cl10 89.75(7) . . ? Cl7 W2 Cl10 179.74(7) . . ? Cl9 W2 Cl8 89.40(4) . . ? Cl9 W2 Cl8 89.40(4) 7_565 . ? Cl11 W2 Cl8 179.71(7) . . ? Cl7 W2 Cl8 90.30(7) . . ? Cl10 W2 Cl8 89.96(7) . . ? Cl16 W3 Cl14 90.70(5) . 7_565 ? Cl16 W3 Cl14 90.70(5) . . ? Cl14 W3 Cl14 178.40(11) 7_565 . ? Cl16 W3 Cl15 90.92(9) . . ? Cl14 W3 Cl15 90.39(5) 7_565 . ? Cl14 W3 Cl15 90.39(5) . . ? Cl16 W3 Cl13 89.74(7) . . ? Cl14 W3 Cl13 89.61(5) 7_565 . ? Cl14 W3 Cl13 89.61(5) . . ? Cl15 W3 Cl13 179.35(8) . . ? Cl16 W3 Cl12 179.35(8) . . ? Cl14 W3 Cl12 89.30(5) 7_565 . ? Cl14 W3 Cl12 89.30(5) . . ? Cl15 W3 Cl12 89.74(9) . . ? Cl13 W3 Cl12 89.61(7) . . ? O1 C11 N1 122.1(5) . . ? O1 C11 C12 125.8(5) . . ? N1 C11 C12 112.1(5) . . ? C11 C12 C13 102.6(5) . . ? C11 C12 H12A 111.2 . . ? C13 C12 H12A 111.2 . . ? C11 C12 H12B 111.2 . . ? C13 C12 H12B 111.2 . . ? H12A C12 H12B 109.2 . . ? C14 C13 C12 105.9(5) . . ? C14 C13 H13A 110.5 . . ? C12 C13 H13A 110.5 . . ? C14 C13 H13B 110.5 . . ? C12 C13 H13B 110.5 . . ? H13A C13 H13B 108.7 . . ? N1 C14 C13 104.7(5) . . ? N1 C14 H14A 110.8 . . ? C13 C14 H14A 110.8 . . ? N1 C14 H14B 110.8 . . ? C13 C14 H14B 110.8 . . ? H14A C14 H14B 108.9 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 O1 H1 109.5 . . ? C11 N1 C15 125.4(5) . . ? C11 N1 C14 112.2(5) . . ? C15 N1 C14 122.3(5) . . ? O2 C21 N2 122.9(5) . . ? O2 C21 C22 126.1(5) . . ? N2 C21 C22 111.0(5) . . ? C21 C22 C23 104.0(5) . . ? C21 C22 H22A 111.0 . . ? C23 C22 H22A 111.0 . . ? C21 C22 H22B 111.0 . . ? C23 C22 H22B 111.0 . . ? H22A C22 H22B 109.0 . . ? C24 C23 C22 105.7(5) . . ? C24 C23 H23A 110.6 . . ? C22 C23 H23A 110.6 . . ? C24 C23 H23B 110.6 . . ? C22 C23 H23B 110.6 . . ? H23A C23 H23B 108.7 . . ? N2 C24 C23 103.8(5) . . ? N2 C24 H24A 111.0 . . ? C23 C24 H24A 111.0 . . ? N2 C24 H24B 111.0 . . ? C23 C24 H24B 111.0 . . ? H24A C24 H24B 109.0 . . ? N2 C25 H25A 109.5 . . ? N2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C21 N2 C25 124.1(5) . . ? C21 N2 C24 113.6(4) . . ? C25 N2 C24 122.1(5) . . ? O3 C31 N3 123.0(6) . . ? O3 C31 C32 128.0(6) . . ? N3 C31 C32 108.9(6) . . ? C31 C32 C33 104.2(5) . . ? C31 C32 H32A 110.9 . . ? C33 C32 H32A 110.9 . . ? C31 C32 H32B 110.9 . . ? C33 C32 H32B 110.9 . . ? H32A C32 H32B 108.9 . . ? C32 C33 C34 103.7(6) . . ? C32 C33 H33A 111.0 . . ? C34 C33 H33A 111.0 . . ? C32 C33 H33B 111.0 . . ? C34 C33 H33B 111.0 . . ? H33A C33 H33B 109.0 . . ? N3 C34 C33 105.0(6) . . ? N3 C34 H34A 110.7 . . ? C33 C34 H34A 110.7 . . ? N3 C34 H34B 110.7 . . ? C33 C34 H34B 110.7 . . ? H34A C34 H34B 108.8 . . ? N3 C35 H35A 109.5 . . ? N3 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N3 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C31 N3 C34 115.2(6) . . ? C31 N3 C35 122.4(6) . . ? C34 N3 C35 122.1(6) . . ? O4 C41 N4 121.4(8) . . ? O4 C41 C42 128.2(9) . . ? N4 C41 C42 110.4(7) . . ? C41 C42 C43 103.6(7) . . ? C41 C42 H42A 111.0 . . ? C43 C42 H42A 111.0 . . ? C41 C42 H42B 111.0 . . ? C43 C42 H42B 111.0 . . ? H42A C42 H42B 109.0 . . ? C42 C43 C44 104.4(9) . . ? C42 C43 H43A 110.9 . . ? C44 C43 H43A 110.9 . . ? C42 C43 H43B 110.9 . . ? C44 C43 H43B 110.9 . . ? H43A C43 H43B 108.9 . . ? N4 C44 C43 103.6(8) . . ? N4 C44 H44A 111.0 . . ? C43 C44 H44A 111.0 . . ? N4 C44 H44B 111.0 . . ? C43 C44 H44B 111.0 . . ? H44A C44 H44B 109.0 . . ? N4 C45 H45A 109.5 . . ? N4 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? N4 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C41 N4 C44 112.9(7) . . ? C41 N4 C45 124.0(8) . . ? C44 N4 C45 122.6(8) . . ? O5 C51 N5 121.9(10) . . ? O5 C51 C52 127.7(10) . . ? N5 C51 C52 110.4(9) . . ? C51 C52 C53 103.7(10) . . ? C51 C52 H52A 111.0 . . ? C53 C52 H52A 111.0 . . ? C51 C52 H52B 111.0 . . ? C53 C52 H52B 111.0 . . ? H52A C52 H52B 109.0 . . ? C52 C53 C54 104.1(10) . . ? C52 C53 H53A 110.9 . . ? C54 C53 H53A 110.9 . . ? C52 C53 H53B 110.9 . . ? C54 C53 H53B 110.9 . . ? H53A C53 H53B 109.0 . . ? N5 C54 C53 105.0(9) . . ? N5 C54 H54A 110.8 . . ? C53 C54 H54A 110.8 . . ? N5 C54 H54B 110.8 . . ? C53 C54 H54B 110.8 . . ? H54A C54 H54B 108.8 . . ? N5 C55 H55A 109.5 . . ? N5 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? N5 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C51 O5 H5 109.5 . . ? C51 N5 C54 113.2(8) . . ? C51 N5 C55 122.6(11) . . ? C54 N5 C55 124.1(11) . . ? 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 C11 C12 C13 -174.6(5) . . . . ? N1 C11 C12 C13 5.5(6) . . . . ? C11 C12 C13 C14 -12.9(7) . . . . ? C12 C13 C14 N1 15.6(7) . . . . ? O1 C11 N1 C15 0.8(8) . . . . ? C12 C11 N1 C15 -179.3(5) . . . . ? O1 C11 N1 C14 -175.2(5) . . . . ? C12 C11 N1 C14 4.8(6) . . . . ? C13 C14 N1 C11 -13.0(6) . . . . ? C13 C14 N1 C15 170.9(5) . . . . ? O2 C21 C22 C23 171.9(6) . . . . ? N2 C21 C22 C23 -7.7(7) . . . . ? C21 C22 C23 C24 12.9(7) . . . . ? C22 C23 C24 N2 -13.4(7) . . . . ? O2 C21 N2 C25 3.1(9) . . . . ? C22 C21 N2 C25 -177.3(5) . . . . ? O2 C21 N2 C24 179.3(5) . . . . ? C22 C21 N2 C24 -1.1(7) . . . . ? C23 C24 N2 C21 9.4(7) . . . . ? C23 C24 N2 C25 -174.3(5) . . . . ? O3 C31 C32 C33 -172.6(7) . . . . ? N3 C31 C32 C33 8.3(7) . . . . ? C31 C32 C33 C34 -15.1(7) . . . . ? C32 C33 C34 N3 16.9(8) . . . . ? O3 C31 N3 C34 -176.1(7) . . . . ? C32 C31 N3 C34 3.0(8) . . . . ? O3 C31 N3 C35 -2.0(10) . . . . ? C32 C31 N3 C35 177.1(5) . . . . ? C33 C34 N3 C31 -13.0(8) . . . . ? C33 C34 N3 C35 172.9(6) . . . . ? O4 C41 C42 C43 170.5(13) . . . . ? N4 C41 C42 C43 -11.4(13) . . . . ? C41 C42 C43 C44 20.4(14) . . . . ? C42 C43 C44 N4 -22.2(14) . . . . ? O4 C41 N4 C44 175.0(10) . . . . ? C42 C41 N4 C44 -3.3(12) . . . . ? O4 C41 N4 C45 3.2(16) . . . . ? C42 C41 N4 C45 -175.1(8) . . . . ? C43 C44 N4 C41 16.4(13) . . . . ? C43 C44 N4 C45 -171.6(10) . . . . ? O5 C51 C52 C53 -168.4(14) . . . . ? N5 C51 C52 C53 13.0(18) . . . . ? C51 C52 C53 C54 -18.2(16) . . . . ? C52 C53 C54 N5 17.8(15) . . . . ? O5 C51 N5 C54 179.9(12) . . . . ? C52 C51 N5 C54 -1.5(17) . . . . ? O5 C51 N5 C55 -2(2) . . . . ? C52 C51 N5 C55 177.0(16) . . . . ? C53 C54 N5 C51 -10.6(14) . . . . ? C53 C54 N5 C55 171.0(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.84 1.62 2.430(5) 159.9 6_556 O4 H4 O3 0.84 1.86 2.660(10) 157.9 . O5 H5 Cl6 0.84 2.84 3.404(8) 126.0 5_566 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.66 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.981 _refine_diff_density_min -0.753 _refine_diff_density_rms 0.112 data_fm250509_P2121 _database_code_depnum_ccdc_archive 'CCDC 893980' #TrackingRef 'fm250509_P2121.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H7 Cl4 N O2 W' _chemical_formula_weight 414.75 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.3608(4) _cell_length_b 9.9793(7) _cell_length_c 16.0433(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1018.37(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5121 _cell_measurement_theta_min 2.4035 _cell_measurement_theta_max 28.667 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 12.347 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2427 _exptl_absorpt_correction_T_max 0.3437 _exptl_absorpt_process_details ? _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 graphite _diffrn_measurement_device_type 'CCD area detector' _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 7238 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 27.99 _reflns_number_total 2384 _reflns_number_gt 2320 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0188P)^2^+0.4556P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.619(7) _refine_ls_number_reflns 2384 _refine_ls_number_parameters 104 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0174 _refine_ls_R_factor_gt 0.0166 _refine_ls_wR_factor_ref 0.0386 _refine_ls_wR_factor_gt 0.0383 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 C1 C 0.7995(7) 0.8946(4) 0.7229(3) 0.0151(9) Uani 1 1 d D . . H1 H 0.692(5) 0.870(4) 0.759(2) 0.018 Uiso 1 1 d D . . C2 C 0.9024(7) 0.9551(4) 0.5827(2) 0.0195(9) Uani 1 1 d . . . H2A H 0.8341 0.9612 0.5281 0.029 Uiso 1 1 calc R . . H2B H 1.0186 0.8908 0.5799 0.029 Uiso 1 1 calc R . . H2C H 0.9568 1.0433 0.5986 0.029 Uiso 1 1 calc R . . C3 C 0.5346(7) 0.8868(5) 0.6166(3) 0.0248(11) Uani 1 1 d . . . H3A H 0.5261 0.9041 0.5566 0.037 Uiso 1 1 calc R . . H3B H 0.4385 0.9471 0.6462 0.037 Uiso 1 1 calc R . . H3C H 0.4949 0.7937 0.6279 0.037 Uiso 1 1 calc R . . Cl1 Cl 0.89908(16) 1.12214(10) 0.87875(7) 0.0201(2) Uani 1 1 d . . . Cl2 Cl 0.85286(17) 0.80245(11) 0.91699(7) 0.0207(2) Uani 1 1 d . . . Cl3 Cl 1.31450(15) 0.75088(11) 0.83449(7) 0.0190(2) Uani 1 1 d . . . Cl4 Cl 1.35874(16) 1.06951(10) 0.79698(7) 0.0216(2) Uani 1 1 d . . . N1 N 0.7485(5) 0.9100(3) 0.6452(2) 0.0139(8) Uani 1 1 d . . . O1 O 0.9845(4) 0.9124(3) 0.7493(2) 0.0156(6) Uani 1 1 d . . . O2 O 1.2332(5) 0.9621(3) 0.9658(2) 0.0240(8) Uani 1 1 d . . . W1 W 1.12341(2) 0.938558(15) 0.870907(9) 0.01265(5) 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 C1 0.019(2) 0.0098(19) 0.017(2) -0.0009(17) 0.0025(17) 0.0000(15) C2 0.023(2) 0.020(2) 0.0153(19) 0.0022(17) 0.0024(17) 0.001(2) C3 0.018(2) 0.034(3) 0.023(3) 0.002(2) -0.005(2) -0.0011(19) Cl1 0.0198(5) 0.0174(4) 0.0232(5) -0.0005(4) 0.0014(5) 0.0054(4) Cl2 0.0186(5) 0.0220(5) 0.0216(5) 0.0038(4) 0.0047(5) -0.0017(5) Cl3 0.0184(5) 0.0149(5) 0.0237(5) 0.0001(4) 0.0042(4) 0.0026(4) Cl4 0.0167(4) 0.0160(4) 0.0320(5) 0.0021(4) 0.0033(4) -0.0046(5) N1 0.0136(15) 0.0121(18) 0.016(2) -0.0014(14) -0.0011(13) -0.0013(13) O1 0.0142(13) 0.0183(17) 0.0142(15) 0.0001(12) 0.0010(11) -0.0010(12) O2 0.0241(15) 0.029(2) 0.0189(16) -0.0051(15) -0.0066(13) 0.0034(14) W1 0.01231(7) 0.01326(7) 0.01237(7) -0.00080(6) -0.00080(7) 0.00069(7) _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 C1 O1 1.263(5) . ? C1 N1 1.297(6) . ? C1 H1 0.931(10) . ? C2 N1 1.471(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 N1 1.455(5) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? Cl1 W1 2.3256(10) . ? Cl2 W1 2.3136(11) . ? Cl3 W1 2.3079(10) . ? Cl4 W1 2.3141(10) . ? O1 W1 2.157(3) . ? O2 W1 1.691(3) . ? 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 C1 N1 122.6(4) . . ? O1 C1 H1 121(3) . . ? N1 C1 H1 117(3) . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 N1 C3 121.2(4) . . ? C1 N1 C2 121.6(4) . . ? C3 N1 C2 117.1(4) . . ? C1 O1 W1 134.6(3) . . ? O2 W1 O1 178.93(15) . . ? O2 W1 Cl3 97.06(11) . . ? O1 W1 Cl3 83.61(9) . . ? O2 W1 Cl2 95.80(12) . . ? O1 W1 Cl2 85.02(8) . . ? Cl3 W1 Cl2 89.78(4) . . ? O2 W1 Cl4 96.64(12) . . ? O1 W1 Cl4 82.53(8) . . ? Cl3 W1 Cl4 89.30(4) . . ? Cl2 W1 Cl4 167.54(4) . . ? O2 W1 Cl1 95.48(11) . . ? O1 W1 Cl1 83.84(8) . . ? Cl3 W1 Cl1 167.45(4) . . ? Cl2 W1 Cl1 89.36(4) . . ? Cl4 W1 Cl1 88.84(4) . . ? 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 C1 N1 C3 179.2(4) . . . . ? O1 C1 N1 C2 -2.6(7) . . . . ? N1 C1 O1 W1 164.7(3) . . . . ? C1 O1 W1 O2 -110(7) . . . . ? C1 O1 W1 Cl3 121.5(4) . . . . ? C1 O1 W1 Cl2 31.1(4) . . . . ? C1 O1 W1 Cl4 -148.4(4) . . . . ? C1 O1 W1 Cl1 -58.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.838 _refine_diff_density_min -0.674 _refine_diff_density_rms 0.123