# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Alessia Bacchi' _publ_contact_author_address ; Parma I-43100 ; _publ_contact_author_email alessia.bacchi@unipr.it loop_ _publ_author_name 'Alessia Bacchi' 'Giulia Cantoni' 'Michele Chierotti' 'Alberto Girlando' 'Roberto Gobetto' ; G.Lapadula ; 'Paolo Pelagatti' 'Angelo Sironi' 'Matteo Zecchini' data_1-H2O-P21/c _database_code_depnum_ccdc_archive 'CCDC 798688' #TrackingRef '- cec2010-spec-bacchi-rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H21 Cl2 N O3 Ru' _chemical_formula_weight 447.31 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' Cl Cl 0.1484 0.1585 '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' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.725(1) _cell_length_b 15.839(2) _cell_length_c 7.4203(7) _cell_angle_alpha 90.00 _cell_angle_beta 84.225(2) _cell_angle_gamma 90.00 _cell_volume 1838.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 1.155 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.578637 _exptl_absorpt_correction_T_max 0.746071 _exptl_absorpt_process_details 'symmetry related measurements (SAINT-SADABS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS CCD diffractometer' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.2 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5637 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 30.59 _reflns_number_total 5637 _reflns_number_gt 4851 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _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^)+(0.0494P)^2^+0.0831P] 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 5637 _refine_ls_number_parameters 223 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0852 _refine_ls_wR_factor_gt 0.0767 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.144 _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 Ru Ru -0.343027(9) 0.057561(8) 0.117405(18) 0.03057(6) Uani 1 1 d . . . Cl1 Cl -0.41316(3) 0.15812(3) -0.06045(8) 0.04671(13) Uani 1 1 d D . . Cl2 Cl -0.28716(3) -0.00403(3) -0.16936(6) 0.04756(13) Uani 1 1 d . . . N N -0.24100(9) 0.14628(9) 0.0877(2) 0.0338(3) Uani 1 1 d . . . O1 O 0.01846(12) 0.31102(13) -0.1135(3) 0.0747(6) Uani 1 1 d D . . O2 O -0.06433(16) 0.40868(14) 0.0265(4) 0.1017(9) Uani 1 1 d . . . O3 O 0.09718(18) 0.44455(15) -0.2342(4) 0.0981(9) Uani 1 1 d D . . C1 C -0.25710(12) 0.22803(12) 0.1315(3) 0.0372(4) Uani 1 1 d . . . H1 H -0.3116 0.2430 0.1816 0.045 Uiso 1 1 calc R . . C2 C -0.19565(13) 0.28988(12) 0.1043(3) 0.0403(4) Uani 1 1 d . . . H2 H -0.2084 0.3454 0.1374 0.048 Uiso 1 1 calc R . . C3 C -0.11514(13) 0.26874(13) 0.0278(3) 0.0416(4) Uani 1 1 d . . . C4 C -0.09683(13) 0.18434(14) -0.0093(3) 0.0445(5) Uani 1 1 d . . . H4 H -0.0421 0.1678 -0.0547 0.053 Uiso 1 1 calc R . . C5 C -0.16132(12) 0.12553(13) 0.0224(3) 0.0408(4) Uani 1 1 d . . . H5 H -0.1489 0.0691 -0.0026 0.049 Uiso 1 1 calc R . . C6 C -0.05085(16) 0.33708(16) -0.0175(4) 0.0575(6) Uani 1 1 d . . . C7 C -0.51364(16) 0.13782(16) 0.3648(4) 0.0603(6) Uani 1 1 d . . . H7A H -0.5093 0.1746 0.2614 0.090 Uiso 1 1 calc RD . . H7B H -0.5050 0.1698 0.4714 0.090 Uiso 1 1 calc R . . H7C H -0.5693 0.1124 0.3791 0.090 Uiso 1 1 calc R . . C8 C -0.31793(15) -0.05798(12) 0.2682(3) 0.0429(5) Uani 1 1 d . . . C9 C -0.39965(14) -0.06391(11) 0.1967(3) 0.0410(4) Uani 1 1 d . . . H9 H -0.4108 -0.1102 0.1256 0.049 Uiso 1 1 calc R . . C10 C -0.46205(13) -0.00253(13) 0.2310(3) 0.0406(4) Uani 1 1 d . . . H10 H -0.5143 -0.0088 0.1840 0.049 Uiso 1 1 calc R . . C11 C -0.44739(14) 0.07057(12) 0.3379(3) 0.0427(5) Uani 1 1 d . . . C12 C -0.36799(14) 0.07613(14) 0.4084(3) 0.0438(5) Uani 1 1 d . . . H12 H -0.3569 0.1223 0.4800 0.053 Uiso 1 1 calc R . . C13 C -0.30455(14) 0.01350(14) 0.3735(3) 0.0440(4) Uani 1 1 d . . . H13 H -0.2525 0.0198 0.4216 0.053 Uiso 1 1 calc R . . C14 C -0.25379(17) -0.12786(16) 0.2272(4) 0.0611(6) Uani 1 1 d . . . H14 H -0.2578 -0.1457 0.1018 0.073 Uiso 1 1 calc R . . C15 C -0.2792(3) -0.2033(2) 0.3488(6) 0.1074(14) Uani 1 1 d . . . H15A H -0.2742 -0.1884 0.4727 0.161 Uiso 1 1 calc R . . H15B H -0.2422 -0.2500 0.3150 0.161 Uiso 1 1 calc R . . H15C H -0.3373 -0.2187 0.3353 0.161 Uiso 1 1 calc R . . C16 C -0.1613(2) -0.1026(2) 0.2422(6) 0.1021(13) Uani 1 1 d . . . H16A H -0.1486 -0.0517 0.1749 0.153 Uiso 1 1 calc R . . H16B H -0.1240 -0.1469 0.1941 0.153 Uiso 1 1 calc R . . H16C H -0.1531 -0.0934 0.3671 0.153 Uiso 1 1 calc R . . H1W H 0.089(4) 0.488(2) -0.144(6) 0.18(2) Uiso 1 1 d D . . H2W H 0.1562(10) 0.438(2) -0.237(8) 0.21(3) Uiso 1 1 d D . . H1O H 0.052(2) 0.3543(19) -0.146(6) 0.130(15) 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 Ru 0.03064(9) 0.03130(9) 0.02905(9) 0.00120(5) 0.00050(6) -0.00579(5) Cl1 0.0406(3) 0.0451(3) 0.0556(3) 0.0154(2) -0.0103(2) -0.0079(2) Cl2 0.0521(3) 0.0546(3) 0.0341(2) -0.0069(2) 0.0049(2) -0.0049(2) N 0.0319(7) 0.0335(7) 0.0354(7) -0.0003(6) 0.0001(6) -0.0039(6) O1 0.0506(10) 0.0719(13) 0.0970(15) -0.0005(11) 0.0159(10) -0.0266(9) O2 0.1011(17) 0.0516(12) 0.142(2) -0.0182(13) 0.0402(16) -0.0377(12) O3 0.0856(18) 0.0842(18) 0.115(2) -0.0040(14) 0.0390(16) -0.0368(12) C1 0.0338(9) 0.0380(9) 0.0388(9) -0.0021(8) 0.0004(7) -0.0026(7) C2 0.0470(11) 0.0344(9) 0.0393(10) -0.0018(8) -0.0041(8) -0.0066(8) C3 0.0389(10) 0.0455(11) 0.0403(10) 0.0003(8) -0.0032(8) -0.0142(8) C4 0.0319(9) 0.0501(11) 0.0500(11) -0.0043(9) 0.0026(8) -0.0063(8) C5 0.0345(9) 0.0364(9) 0.0504(11) -0.0032(8) 0.0010(8) -0.0019(7) C6 0.0522(13) 0.0576(14) 0.0613(14) 0.0011(11) 0.0016(11) -0.0254(11) C7 0.0508(13) 0.0521(13) 0.0724(17) 0.0029(12) 0.0216(11) 0.0026(10) C8 0.0492(12) 0.0423(11) 0.0363(10) 0.0099(8) 0.0000(9) 0.0011(8) C9 0.0511(12) 0.0322(9) 0.0386(10) 0.0040(7) 0.0002(9) -0.0109(8) C10 0.0375(10) 0.0398(10) 0.0430(10) 0.0066(8) 0.0028(8) -0.0111(8) C11 0.0447(11) 0.0396(10) 0.0403(10) 0.0039(8) 0.0124(9) -0.0066(8) C12 0.0521(12) 0.0468(11) 0.0308(9) -0.0048(8) 0.0034(8) -0.0123(9) C13 0.0448(11) 0.0569(12) 0.0306(9) 0.0036(9) -0.0042(8) -0.0052(9) C14 0.0690(16) 0.0557(14) 0.0565(14) 0.0119(11) 0.0037(12) 0.0192(12) C15 0.125(3) 0.0642(19) 0.123(3) 0.041(2) 0.036(2) 0.040(2) C16 0.063(2) 0.094(3) 0.147(4) 0.023(2) -0.002(2) 0.0282(18) _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 Ru N 2.1275(15) . ? Ru C13 2.167(2) . ? Ru C12 2.176(2) . ? Ru C9 2.1761(18) . ? Ru C10 2.1914(19) . ? Ru C8 2.2011(19) . ? Ru C11 2.207(2) . ? Ru Cl1 2.4057(5) . ? Ru Cl2 2.4238(5) . ? N C5 1.338(2) . ? N C1 1.353(2) . ? O1 C6 1.308(3) . ? O2 C6 1.193(3) . ? C1 C2 1.377(3) . ? C2 C3 1.376(3) . ? C3 C4 1.389(3) . ? C3 C6 1.496(3) . ? C4 C5 1.380(3) . ? C7 C11 1.489(3) . ? C8 C13 1.404(3) . ? C8 C9 1.442(3) . ? C8 C14 1.508(3) . ? C9 C10 1.387(3) . ? C10 C11 1.435(3) . ? C11 C12 1.404(3) . ? C12 C13 1.412(3) . ? C14 C16 1.523(4) . ? C14 C15 1.526(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 N Ru C13 91.68(7) . . ? N Ru C12 94.14(7) . . ? C13 Ru C12 37.95(8) . . ? N Ru C9 153.60(7) . . ? C13 Ru C9 67.72(8) . . ? C12 Ru C9 79.81(8) . . ? N Ru C10 158.86(7) . . ? C13 Ru C10 79.96(8) . . ? C12 Ru C10 67.36(8) . . ? C9 Ru C10 37.02(8) . . ? N Ru C8 115.46(7) . . ? C13 Ru C8 37.48(8) . . ? C12 Ru C8 68.39(8) . . ? C9 Ru C8 38.45(8) . . ? C10 Ru C8 68.48(8) . . ? N Ru C11 120.78(7) . . ? C13 Ru C11 68.42(9) . . ? C12 Ru C11 37.36(8) . . ? C9 Ru C11 68.20(8) . . ? C10 Ru C11 38.08(8) . . ? C8 Ru C11 81.88(8) . . ? N Ru Cl1 83.60(4) . . ? C13 Ru Cl1 151.42(6) . . ? C12 Ru Cl1 114.08(6) . . ? C9 Ru Cl1 122.41(6) . . ? C10 Ru Cl1 94.46(6) . . ? C8 Ru Cl1 160.86(6) . . ? C11 Ru Cl1 89.84(6) . . ? N Ru Cl2 88.40(4) . . ? C13 Ru Cl2 122.13(6) . . ? C12 Ru Cl2 159.89(6) . . ? C9 Ru Cl2 89.08(6) . . ? C10 Ru Cl2 112.52(6) . . ? C8 Ru Cl2 92.51(6) . . ? C11 Ru Cl2 149.89(6) . . ? Cl1 Ru Cl2 86.02(2) . . ? C5 N C1 117.90(16) . . ? C5 N Ru 122.96(13) . . ? C1 N Ru 119.11(12) . . ? N C1 C2 122.30(18) . . ? C3 C2 C1 119.37(18) . . ? C2 C3 C4 118.68(17) . . ? C2 C3 C6 119.3(2) . . ? C4 C3 C6 122.0(2) . . ? C5 C4 C3 118.80(19) . . ? N C5 C4 122.77(19) . . ? O2 C6 O1 124.4(2) . . ? O2 C6 C3 121.9(2) . . ? O1 C6 C3 113.7(2) . . ? C13 C8 C9 116.52(19) . . ? C13 C8 C14 124.7(2) . . ? C9 C8 C14 118.8(2) . . ? C13 C8 Ru 69.95(11) . . ? C9 C8 Ru 69.83(11) . . ? C14 C8 Ru 131.17(16) . . ? C10 C9 C8 121.83(19) . . ? C10 C9 Ru 72.09(11) . . ? C8 C9 Ru 71.72(11) . . ? C9 C10 C11 121.1(2) . . ? C9 C10 Ru 70.89(11) . . ? C11 C10 Ru 71.56(11) . . ? C12 C11 C10 117.06(19) . . ? C12 C11 C7 122.8(2) . . ? C10 C11 C7 120.1(2) . . ? C12 C11 Ru 70.09(12) . . ? C10 C11 Ru 70.35(11) . . ? C7 C11 Ru 128.61(15) . . ? C11 C12 C13 121.72(19) . . ? C11 C12 Ru 72.55(12) . . ? C13 C12 Ru 70.70(11) . . ? C8 C13 C12 121.7(2) . . ? C8 C13 Ru 72.57(12) . . ? C12 C13 Ru 71.35(12) . . ? C8 C14 C16 114.6(2) . . ? C8 C14 C15 109.0(2) . . ? C16 C14 C15 110.9(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.59 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.579 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.111 #===END data_1alpha_P21/n _database_code_depnum_ccdc_archive 'CCDC 798689' #TrackingRef '- cec2010-spec-bacchi-rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H19 Cl2 N O2 Ru' _chemical_formula_weight 429.29 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' Cl Cl 0.1484 0.1585 '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' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.0199(9) _cell_length_b 7.2739(4) _cell_length_c 15.4998(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.452(5) _cell_angle_gamma 90.00 _cell_volume 1685.74(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.252 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 1. _exptl_absorpt_process_details 'symmetry related measurements (SAINT-SADABS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS CCD diffractometer' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 8.2 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22625 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4186 _reflns_number_gt 3408 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR2004 (Altomare et al., 2004)' _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^)+(0.0554P)^2^+0.0965P] 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 4186 _refine_ls_number_parameters 206 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 Ru Ru 0.413930(13) -0.17966(3) 0.212111(14) 0.02791(9) Uani 1 1 d . . . Cl1 Cl 0.44768(5) 0.04932(10) 0.32401(5) 0.04218(18) Uani 1 1 d . . . Cl2 Cl 0.39425(5) 0.07468(10) 0.11191(5) 0.04198(18) Uani 1 1 d . . . N N 0.55351(15) -0.1697(3) 0.19703(15) 0.0298(5) Uani 1 1 d . . . O1 O 0.86734(15) -0.1133(4) 0.11366(16) 0.0561(6) Uani 1 1 d . . . O2 O 0.87907(15) -0.2942(3) 0.23053(19) 0.0548(7) Uani 1 1 d D . . C1 C 0.58693(19) -0.1216(4) 0.12303(18) 0.0345(6) Uani 1 1 d . . . H1 H 0.5477 -0.0832 0.0764 0.041 Uiso 1 1 calc R . . C2 C 0.67736(19) -0.1269(4) 0.11344(18) 0.0347(6) Uani 1 1 d . . . H2 H 0.6983 -0.0907 0.0615 0.042 Uiso 1 1 calc R . . C3 C 0.73659(18) -0.1863(3) 0.18160(19) 0.0328(6) Uani 1 1 d . . . C4 C 0.70199(19) -0.2381(4) 0.25798(19) 0.0355(6) Uani 1 1 d . . . H4 H 0.7398 -0.2808 0.3047 0.043 Uiso 1 1 calc R . . C5 C 0.61133(19) -0.2257(4) 0.26395(19) 0.0358(6) Uani 1 1 d . . . H5 H 0.5891 -0.2571 0.3160 0.043 Uiso 1 1 calc R . . C6 C 0.83469(19) -0.1934(4) 0.1710(2) 0.0368(6) Uani 1 1 d . . . C7 C 0.32907(19) -0.3560(4) 0.12376(19) 0.0342(6) Uani 1 1 d . . . C8 C 0.27553(18) -0.2661(4) 0.1831(2) 0.0370(6) Uani 1 1 d . . . H8 H 0.2254 -0.1999 0.1613 0.044 Uiso 1 1 calc R . . C9 C 0.29670(19) -0.2754(4) 0.2727(2) 0.0399(7) Uani 1 1 d . . . H9 H 0.2610 -0.2144 0.3093 0.048 Uiso 1 1 calc R . . C10 C 0.3723(2) -0.3773(4) 0.30873(19) 0.0397(7) Uani 1 1 d . . . C11 C 0.4240(2) -0.4678(4) 0.2506(2) 0.0396(7) Uani 1 1 d . . . H11 H 0.4734 -0.5363 0.2724 0.047 Uiso 1 1 calc R . . C12 C 0.40277(18) -0.4570(4) 0.1595(2) 0.0372(6) Uani 1 1 d . . . H12 H 0.4385 -0.5183 0.1230 0.045 Uiso 1 1 calc R . . C13 C 0.3986(3) -0.3826(6) 0.4052(2) 0.0621(10) Uani 1 1 d . . . H13A H 0.4463 -0.4695 0.4175 0.093 Uiso 1 1 calc R . . H13B H 0.3480 -0.4190 0.4346 0.093 Uiso 1 1 calc R . . H13C H 0.4183 -0.2629 0.4248 0.093 Uiso 1 1 calc R . . C14 C 0.3033(2) -0.3368(4) 0.0272(2) 0.0433(7) Uani 1 1 d . . . H14 H 0.2823 -0.2107 0.0161 0.052 Uiso 1 1 calc R . . C15 C 0.2252(2) -0.4670(6) 0.0016(2) 0.0633(10) Uani 1 1 d . . . H15A H 0.1777 -0.4436 0.0374 0.095 Uiso 1 1 calc R . . H15B H 0.2449 -0.5919 0.0093 0.095 Uiso 1 1 calc R . . H15C H 0.2039 -0.4470 -0.0581 0.095 Uiso 1 1 calc R . . C16 C 0.3814(2) -0.3722(6) -0.0282(2) 0.0591(9) Uani 1 1 d . . . H16A H 0.4027 -0.4957 -0.0190 0.089 Uiso 1 1 calc R . . H16B H 0.4291 -0.2874 -0.0119 0.089 Uiso 1 1 calc R . . H16C H 0.3612 -0.3554 -0.0883 0.089 Uiso 1 1 calc R . . H1O H 0.9356(14) -0.310(6) 0.228(3) 0.099(18) 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 Ru 0.02401(13) 0.02545(13) 0.03534(14) 0.00088(8) 0.00846(9) 0.00024(8) Cl1 0.0375(4) 0.0426(4) 0.0486(4) -0.0121(3) 0.0155(3) -0.0085(3) Cl2 0.0429(4) 0.0338(4) 0.0497(4) 0.0101(3) 0.0066(3) 0.0042(3) N 0.0270(11) 0.0286(11) 0.0353(12) 0.0008(9) 0.0103(9) 0.0002(9) O1 0.0393(12) 0.0746(16) 0.0575(15) 0.0115(13) 0.0211(11) -0.0019(12) O2 0.0296(12) 0.0607(15) 0.0765(18) 0.0222(12) 0.0184(12) 0.0129(11) C1 0.0308(14) 0.0389(15) 0.0344(15) 0.0029(12) 0.0067(11) 0.0014(12) C2 0.0325(14) 0.0374(14) 0.0360(15) 0.0010(12) 0.0128(12) 0.0003(12) C3 0.0284(14) 0.0306(14) 0.0405(15) -0.0022(11) 0.0097(11) -0.0004(11) C4 0.0313(14) 0.0356(14) 0.0397(16) 0.0036(12) 0.0037(12) 0.0044(12) C5 0.0324(15) 0.0402(15) 0.0360(15) 0.0048(12) 0.0098(12) 0.0016(12) C6 0.0296(14) 0.0349(15) 0.0470(17) -0.0052(12) 0.0101(13) 0.0004(11) C7 0.0308(14) 0.0293(13) 0.0433(16) -0.0023(11) 0.0078(12) -0.0048(11) C8 0.0253(14) 0.0347(14) 0.0520(18) -0.0015(13) 0.0086(12) -0.0015(11) C9 0.0321(15) 0.0409(16) 0.0498(18) -0.0031(13) 0.0204(13) -0.0070(12) C10 0.0438(17) 0.0340(14) 0.0430(17) 0.0077(12) 0.0122(14) -0.0088(13) C11 0.0379(16) 0.0244(13) 0.0571(19) 0.0070(13) 0.0085(13) 0.0007(12) C12 0.0340(14) 0.0247(13) 0.0546(18) -0.0050(13) 0.0126(13) -0.0009(11) C13 0.077(3) 0.064(2) 0.046(2) 0.0128(18) 0.0073(18) -0.013(2) C14 0.0431(17) 0.0441(17) 0.0427(17) -0.0033(13) 0.0048(14) -0.0044(13) C15 0.055(2) 0.087(3) 0.048(2) -0.0109(19) 0.0030(17) -0.024(2) C16 0.053(2) 0.079(3) 0.047(2) -0.0038(18) 0.0131(17) -0.0073(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ru N 2.133(2) . ? Ru C12 2.177(3) . ? Ru C8 2.177(3) . ? Ru C11 2.180(3) . ? Ru C9 2.187(3) . ? Ru C7 2.194(3) . ? Ru C10 2.208(3) . ? Ru Cl2 2.4155(7) . ? Ru Cl1 2.4233(7) . ? N C1 1.341(3) . ? N C5 1.351(4) . ? O1 C6 1.206(4) . ? O2 C6 1.310(4) . ? C1 C2 1.381(4) . ? C2 C3 1.384(4) . ? C3 C4 1.389(4) . ? C3 C6 1.499(4) . ? C4 C5 1.377(4) . ? C7 C12 1.399(4) . ? C7 C8 1.436(4) . ? C7 C14 1.516(4) . ? C8 C9 1.396(4) . ? C9 C10 1.425(4) . ? C10 C11 1.407(4) . ? C10 C13 1.510(4) . ? C11 C12 1.420(5) . ? C14 C15 1.531(4) . ? C14 C16 1.540(5) . ? 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 N Ru C12 91.84(9) . . ? N Ru C8 156.41(10) . . ? C12 Ru C8 67.48(11) . . ? N Ru C11 91.10(9) . . ? C12 Ru C11 38.04(12) . . ? C8 Ru C11 79.58(11) . . ? N Ru C9 153.89(11) . . ? C12 Ru C9 80.16(11) . . ? C8 Ru C9 37.32(11) . . ? C11 Ru C9 67.30(11) . . ? N Ru C7 118.06(10) . . ? C12 Ru C7 37.33(10) . . ? C8 Ru C7 38.35(11) . . ? C11 Ru C7 68.30(11) . . ? C9 Ru C7 68.79(11) . . ? N Ru C10 116.16(10) . . ? C12 Ru C10 68.52(11) . . ? C8 Ru C10 68.04(11) . . ? C11 Ru C10 37.40(11) . . ? C9 Ru C10 37.83(12) . . ? C7 Ru C10 81.83(11) . . ? N Ru Cl2 87.99(6) . . ? C12 Ru Cl2 117.96(8) . . ? C8 Ru Cl2 91.86(8) . . ? C11 Ru Cl2 155.96(9) . . ? C9 Ru Cl2 117.77(9) . . ? C7 Ru Cl2 91.03(8) . . ? C10 Ru Cl2 155.41(9) . . ? N Ru Cl1 85.07(6) . . ? C12 Ru Cl1 155.31(8) . . ? C8 Ru Cl1 118.48(8) . . ? C11 Ru Cl1 117.41(9) . . ? C9 Ru Cl1 91.93(8) . . ? C7 Ru Cl1 156.66(8) . . ? C10 Ru Cl1 90.88(8) . . ? Cl2 Ru Cl1 86.46(3) . . ? C1 N C5 118.0(2) . . ? C1 N Ru 123.65(19) . . ? C5 N Ru 118.19(18) . . ? N C1 C2 122.4(3) . . ? C1 C2 C3 119.6(3) . . ? C2 C3 C4 118.0(3) . . ? C2 C3 C6 119.6(3) . . ? C4 C3 C6 122.3(3) . . ? C5 C4 C3 119.5(3) . . ? N C5 C4 122.4(3) . . ? O1 C6 O2 125.1(3) . . ? O1 C6 C3 122.5(3) . . ? O2 C6 C3 112.5(3) . . ? C12 C7 C8 117.1(3) . . ? C12 C7 C14 123.9(3) . . ? C8 C7 C14 119.0(3) . . ? C12 C7 Ru 70.66(16) . . ? C8 C7 Ru 70.20(16) . . ? C14 C7 Ru 129.9(2) . . ? C9 C8 C7 121.8(3) . . ? C9 C8 Ru 71.71(17) . . ? C7 C8 Ru 71.45(16) . . ? C8 C9 C10 120.8(3) . . ? C8 C9 Ru 70.97(16) . . ? C10 C9 Ru 71.90(16) . . ? C11 C10 C9 117.4(3) . . ? C11 C10 C13 120.9(3) . . ? C9 C10 C13 121.7(3) . . ? C11 C10 Ru 70.22(16) . . ? C9 C10 Ru 70.27(16) . . ? C13 C10 Ru 128.6(2) . . ? C10 C11 C12 121.7(3) . . ? C10 C11 Ru 72.38(16) . . ? C12 C11 Ru 70.84(15) . . ? C7 C12 C11 121.2(3) . . ? C7 C12 Ru 72.01(16) . . ? C11 C12 Ru 71.13(15) . . ? C7 C14 C15 108.5(3) . . ? C7 C14 C16 113.5(3) . . ? C15 C14 C16 111.0(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.430 _refine_diff_density_min -0.781 _refine_diff_density_rms 0.095 #===END data_1beta _database_code_depnum_ccdc_archive 'CCDC 798690' #TrackingRef '- cec2010-spec-bacchi-rev.cif' _chemical_name_systematic ; [(eta6-p-cymene)Ru(II)Cl2(isonicotinic acid)] ; _chemical_name_common '((eta6-p-cymene)Ru(ii)Cl2(isonicotinic acid))' _chemical_formula_moiety 'C16 H19 Cl2 N O2 Ru' _chemical_formula_structural 'C16 H19 Cl2 N O2 Ru' _chemical_formula_analytical 'Ru Cl2 (C10 H14) (C6 O2 H5)' _chemical_formula_sum 'C16 H19 Cl2 N O2 Ru' _chemical_formula_weight 429.29 _chemical_melting_point ? _chemical_compound_source 'Phase transition' 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' Cl Cl 0.1484 0.1585 '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' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' # 4.2 POWDER SPECIMEN AND CRYSTAL DATA _space_group_crystal_system monoclinic _space_group_name_H-M_alt P21/c _space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz '-x, -y, -z' '-x, y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' 'x, y, z' _cell_length_a 14.7083(10) _cell_length_b 15.0887(10) _cell_length_c 7.72552(49) _cell_angle_alpha 90 _cell_angle_beta 98.0506(40) _cell_angle_gamma 90 _cell_volume 1697.62(20) _cell_formula_units_Z 4 _cell_measurement_temperature 373 _pd_calibration_special_details ; ? ; _cell_special_details ; ? ; _exptl_crystal_density_diffrn ? _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 ? # The next three fields give the specimen dimensions in mm. # The equatorial plane contains the incident and diffracted beam. _pd_spec_size_axial 15 # perpendicular to # equatorial plane _pd_spec_size_equat 20 # parallel to # scattering vector # in transmission _pd_spec_size_thick 0.02 # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting ; packed powder pellet ; _pd_spec_mount_mode reflection # options are reflection # or transmission _pd_spec_shape flat_sheet # options are cylinder # flat_sheet or irregular _pd_char_particle_morphology ? _pd_char_colour yellow # use ICDD colour descriptions # The next four fields are normally only needed for transmission experiments. _exptl_absorpt_coefficient_mu 10.4 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? # 4.3 EXPERIMENTAL DATA _exptl_special_details ; ? ; # This following item is used to identify the equipment used to record the # powder pattern when the diffractogram was measured at a laboratory # other than the authors home institution e.g. when neutron or synchrotron # radiation is used. _pd_instr_location ; ? ; _diffrn_ambient_temperature 373 _diffrn_source_target Cu _diffrn_source_type 'sealed X-ray tube' _diffrn_measurement_device_type 'Bruker AXS D8 Advance' _diffrn_detector_type ; Bruker Lynxeye linear position sensitive detector ; _pd_meas_scan_method cont # options are step or cont # tof or fixed or # disp (= dispersive) _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. loop_ _diffrn_radiation_type ; CuK\a1 1.54056 CuK\a2 1.54439 ; _diffrn_radiation_wavelength 1.54056 _diffrn_radiation_monochromator 'nickel filter' # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 5001 _pd_meas_2theta_range_min 5 _pd_meas_2theta_range_max 90 _pd_meas_2theta_range_inc 0.02 # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec ? _pd_instr_dist_spec/detc ? _pd_meas_2theta_fixed ? # The following fields are used to identify the programs used. _computing_data_collection ? _computing_cell_refinement TOPAS-R _computing_data_reduction ? _computing_structure_solution TOPAS-R _computing_structure_refinement TOPAS-R _computing_molecular_graphics ? _computing_publication_material TOPAS-R # 4.4 REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; The use of a rigid body description for the p-cymene-Ru(II) fragment does not allow the derivation of statistically meaningful s.u.'s for its atoms. Only center of mass (X, Y, Z) and rotational angles (RX, RY, RZ) s.u.'s are available. TX1, TY1, TZ1 -0.7488(2), 0.07998(3), -0.16377(5) RX1, RY1, RZ1 -291.3(2), 242.9(2), 296.7(2) The rigid body describing the isonicotinic acid TX2, TY2, TZ2 0.1906(4), 0.1160(4), 0.675(3) RX2, RY2, RZ2 -244.2(3), 88.4(3), 30.7(3) ; # The next three items are given as text _pd_proc_ls_profile_function 'fundamental parameters approach' _pd_proc_ls_background_function 'Chebychev polynomial' _pd_proc_ls_pref_orient_corr ? _pd_proc_ls_prof_R_factor 0.051 _pd_proc_ls_prof_wR_factor 0.068 _pd_proc_ls_prof_wR_expected 0.029 _refine_special_details ; ? ; _refine_ls_structure_factor_coef Inet _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 1/[Y~i~] _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_parameters ? _refine_ls_number_restraints ? _refine_ls_number_constraints ? _refine_ls_goodness_of_fit_all 2.34 # The above item is CHI squared _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? _refine_ls_shift/su_max .01 _refine_ls_shift/su_mean ? # The following four items apply to angular dispersive measurements. # 2theta minimum maximum and increment (in degrees) are for the # intensities used in the refinement. _pd_proc_2theta_range_min 4 _pd_proc_2theta_range_max 90 _pd_proc_2theta_range_inc 0.02 loop_ _pd_proc_wavelength 1.540562 1.544390 _pd_block_diffractogram_id ? # The id used for the block # containing the powder # pattern profile (section 11). # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions ? _pd_proc_info_data_reduction ? # 4.5 ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv Cl1 Cl 4 -0.88047(69) 0.36289(45) 0.98161(78) 1 7.92(16) Cl2 Cl 4 -0.74346(73) -0.48157(83) -0.9943(16) 1 7.92(16) Ru Ru 4 -0.8204879 0.04881162 -0.2684779 1 7.92(16) C8 C 4 -0.7976407 -0.0413075 -0.04188232 1 9.92(16) C9 C 4 -0.8771951 -0.06896679 -0.1612419 1 9.92(16) C10 C 4 -0.9493363 -0.01141339 -0.2146936 1 9.92(16) C11 C 4 -0.9469094 0.07887594 -0.1560383 1 9.92(16) C12 C 4 -0.8698518 0.1061466 -0.04094386 1 9.92(16) C13 C 4 -0.7963919 0.04707177 0.01524713 1 9.92(16) H10 H 4 -1.000057 -0.03170735 -0.2898725 1 9.92(16) H12 H 4 -0.8666895 0.1642152 -0.0003571752 1 9.92(16) H9 H 4 -0.8801006 -0.1268344 -0.203193 1 9.92(16) H13 H 4 -0.7462495 0.06745609 0.09178804 1 9.92(16) C14 C 4 -0.723189 -0.1084479 0.0124278 1 9.92(16) C15 C 4 -0.6465182 -0.09497683 -0.09811492 1 9.92(16) C16 C 4 -0.7578723 -0.2054311 0.003334986 1 9.92(16) H14 H 4 -0.6978672 -0.09608416 0.1342464 1 9.92(16) H15A H 4 -0.6693128 -0.1067509 -0.2184705 1 9.92(16) H15B H 4 -0.5968763 -0.1346941 -0.05952105 1 9.92(16) H15C H 4 -0.6249897 -0.03496559 -0.08613483 1 9.92(16) H16A H 4 -0.81274 -0.2095813 0.05701389 1 9.92(16) H16B H 4 -0.7115057 -0.2432941 0.06386596 1 9.92(16) H16C H 4 -0.7708578 -0.2235685 -0.1166915 1 9.92(16) C7 C 4 -1.023608 0.140201 -0.2246031 1 9.92(16) H7A H 4 -1.024078 0.1486101 -0.3478301 1 9.92(16) H7B H 4 -1.014804 0.1962803 -0.1659314 1 9.92(16) H7C H 4 -1.080985 0.1149701 -0.2037732 1 9.92(16) N N 4 0.2767715 0.1533907 0.7653497 1 9.92(16) C1 C 4 0.3641983 0.1429449 0.7348624 1 9.92(16) H1 H 4 0.3837846 0.08694296 0.7057603 1 9.92(16) C2 C 4 0.425737 0.2129682 0.7455476 1 9.92(16) H2 H 4 0.4855236 0.2039424 0.7227819 1 9.92(16) C3 C 4 0.3979367 0.2955434 0.7900479 1 9.92(16) C4 C 4 0.3061941 0.3080917 0.8136186 1 9.92(16) H4 H 4 0.2846286 0.3640548 0.8378724 1 9.92(16) C5 C 4 0.2484256 0.2353697 0.8001694 1 9.92(16) H5 H 4 0.1874741 0.2435521 0.8157995 1 9.92(16) C6 C 4 0.4667147 0.3687444 0.8182259 1 9.92(16) O1 O 4 0.5436952 0.3460925 0.9160615 1 9.92(16) O2 O 4 0.453026 0.4399921 0.7519057 1 9.92(16) H1O H 4 0.601736 0.3714603 0.9488624 1 9.92(16)