# 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_cc2c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H12 Cl4 Mo O2' _chemical_formula_weight 329.88 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' Mo Mo -1.6832 0.6857 '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 7.5238(17) _cell_length_b 11.9246(17) _cell_length_c 12.347(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.869(3) _cell_angle_gamma 90.00 _cell_volume 1065.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4595 _cell_measurement_theta_min 3.2925 _cell_measurement_theta_max 28.671 _exptl_crystal_description prism _exptl_crystal_colour orange-green _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.056 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 2.189 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7209 _exptl_absorpt_correction_T_max 0.7792 _exptl_absorpt_process_details ; Data were corrected for Lorentz polarization and absorption effects (empirical absorption correction SADABS). R(int) = 0.1232 (selected reflections only, before parameter refinement) R(int) = 0.0357 (selected reflections only, after parameter refinement) ; _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 4843 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0156 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 25.02 _reflns_number_total 936 _reflns_number_gt 915 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1996)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0721P)^2^+31.6120P] 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 SHELXL _refine_ls_extinction_coef 0.0125(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 936 _refine_ls_number_parameters 54 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1604 _refine_ls_wR_factor_gt 0.1596 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.7648(11) 0.1544(8) 0.1316(7) 0.0351(19) Uani 1 1 d . . . H1A H 0.7328 0.1345 0.0516 0.053 Uiso 1 1 calc R . . H1B H 0.8432 0.0956 0.1758 0.053 Uiso 1 1 calc R . . H1C H 0.8316 0.2258 0.1434 0.053 Uiso 1 1 calc R . . C2 C 0.4858(11) 0.2557(7) 0.1086(7) 0.038(2) Uani 1 1 d . . . H2A H 0.5575 0.3254 0.1213 0.057 Uiso 1 1 calc R . . H2B H 0.3770 0.2641 0.1370 0.057 Uiso 1 1 calc R . . H2C H 0.4461 0.2394 0.0277 0.057 Uiso 1 1 calc R . . Cl1 Cl 0.6019(4) -0.0971(3) 0.1579(2) 0.0679(9) Uani 1 1 d . . . Cl2 Cl 0.2154(2) 0.04380(15) 0.11317(15) 0.0254(5) Uani 1 1 d . . . Mo1 Mo 0.5000 0.02086(8) 0.2500 0.0421(5) Uani 1 2 d S . . O1 O 0.5988(7) 0.1648(4) 0.1670(4) 0.0266(11) 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 0.032(4) 0.044(5) 0.029(4) 0.000(3) 0.008(3) -0.012(4) C2 0.030(4) 0.030(4) 0.045(5) 0.015(4) -0.005(3) -0.005(3) Cl1 0.0507(16) 0.088(2) 0.0626(17) -0.0147(15) 0.0118(13) -0.0057(15) Cl2 0.0168(9) 0.0261(9) 0.0287(10) -0.0031(7) -0.0015(7) -0.0030(6) Mo1 0.0229(7) 0.0151(6) 0.0691(9) 0.000 -0.0200(5) 0.000 O1 0.019(2) 0.026(3) 0.031(3) 0.005(2) -0.001(2) -0.003(2) _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 1.436(10) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O1 1.443(9) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? Cl1 Mo1 2.083(3) . ? Cl2 Mo1 2.3526(17) . ? Mo1 Cl1 2.083(3) 2_655 ? Mo1 O1 2.228(5) . ? Mo1 O1 2.228(5) 2_655 ? Mo1 Cl2 2.3526(17) 2_655 ? 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 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 H2A 109.5 . . ? O1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? O1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? Cl1 Mo1 Cl1 95.05(19) 2_655 . ? Cl1 Mo1 O1 172.04(17) 2_655 . ? Cl1 Mo1 O1 92.85(17) . . ? Cl1 Mo1 O1 92.85(17) 2_655 2_655 ? Cl1 Mo1 O1 172.04(17) . 2_655 ? O1 Mo1 O1 79.3(3) . 2_655 ? Cl1 Mo1 Cl2 94.87(9) 2_655 2_655 ? Cl1 Mo1 Cl2 94.14(9) . 2_655 ? O1 Mo1 Cl2 83.59(13) . 2_655 ? O1 Mo1 Cl2 86.13(13) 2_655 2_655 ? Cl1 Mo1 Cl2 94.14(9) 2_655 . ? Cl1 Mo1 Cl2 94.87(9) . . ? O1 Mo1 Cl2 86.13(13) . . ? O1 Mo1 Cl2 83.59(13) 2_655 . ? Cl2 Mo1 Cl2 166.64(10) 2_655 . ? C1 O1 C2 110.8(6) . . ? C1 O1 Mo1 120.0(5) . . ? C2 O1 Mo1 125.7(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 Cl1 Mo1 O1 C1 140.6(9) 2_655 . . . ? Cl1 Mo1 O1 C1 -32.5(5) . . . . ? O1 Mo1 O1 C1 148.7(6) 2_655 . . . ? Cl2 Mo1 O1 C1 61.4(5) 2_655 . . . ? Cl2 Mo1 O1 C1 -127.1(5) . . . . ? Cl1 Mo1 O1 C2 -62.4(13) 2_655 . . . ? Cl1 Mo1 O1 C2 124.5(6) . . . . ? O1 Mo1 O1 C2 -54.3(5) 2_655 . . . ? Cl2 Mo1 O1 C2 -141.6(6) 2_655 . . . ? Cl2 Mo1 O1 C2 29.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.976 _refine_diff_density_min -2.150 _refine_diff_density_rms 0.182 _database_code_depnum_ccdc_archive 'CCDC 943840' ####################################################################### # # 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_p2121 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H10 Cl4 Mo2 O5' _chemical_formula_weight 459.79 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' Mo Mo -1.6832 0.6857 '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 9.390(3) _cell_length_b 11.420(3) _cell_length_c 12.617(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1352.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9895 _cell_measurement_theta_min 2.4055 _cell_measurement_theta_max 28.5035 _exptl_crystal_description prism _exptl_crystal_colour brown-orange _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 2.636 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6075 _exptl_absorpt_correction_T_max 0.7092 _exptl_absorpt_process_details ; Data were corrected for Lorentz polarization and absorption effects (empirical absorption correction SADABS). R(int) = 0.1718 (selected reflections only, before parameter refinement) R(int) = 0.0823 (selected reflections only, after parameter refinement) ; _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 12028 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2659 _reflns_number_gt 2625 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1996)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0252P)^2^+1.5004P] 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 0.92(6) _refine_ls_number_reflns 2659 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0252 _refine_ls_wR_factor_ref 0.0641 _refine_ls_wR_factor_gt 0.0640 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _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 C3 C 0.2571(5) 0.3750(4) 1.0773(4) 0.0284(10) Uani 1 1 d . . . H3A H 0.3430 0.4201 1.0943 0.043 Uiso 1 1 calc R . . H3B H 0.2818 0.3111 1.0288 0.043 Uiso 1 1 calc R . . H3C H 0.2167 0.3425 1.1426 0.043 Uiso 1 1 calc R . . C4 C -0.1144(5) 0.5984(4) 0.7711(4) 0.0298(11) Uani 1 1 d . . . H4A H -0.2104 0.5654 0.7762 0.045 Uiso 1 1 calc R . . H4B H -0.0702 0.5732 0.7045 0.045 Uiso 1 1 calc R . . H4C H -0.1200 0.6841 0.7726 0.045 Uiso 1 1 calc R . . C5 C 0.0182(5) 0.6432(5) 1.1632(3) 0.0293(10) Uani 1 1 d . . . H5A H 0.0238 0.7278 1.1755 0.044 Uiso 1 1 calc R . . H5B H 0.1096 0.6069 1.1813 0.044 Uiso 1 1 calc R . . H5C H -0.0571 0.6096 1.2076 0.044 Uiso 1 1 calc R . . Cl1 Cl 0.16005(11) 0.76528(9) 0.84492(8) 0.0228(2) Uani 1 1 d . . . Cl2 Cl -0.28901(11) 0.45739(10) 0.95740(10) 0.0286(2) Uani 1 1 d . . . Cl3 Cl 0.34657(12) 0.65001(10) 1.03053(10) 0.0316(3) Uani 1 1 d . . . Cl4 Cl -0.08739(13) 0.33921(11) 1.13262(9) 0.0295(3) Uani 1 1 d . . . Mo1 Mo 0.16859(3) 0.57632(3) 0.91641(3) 0.01640(10) Uani 1 1 d . . . Mo2 Mo -0.04286(3) 0.42929(3) 0.96909(2) 0.01538(10) Uani 1 1 d . . . O1 O 0.2580(4) 0.5001(3) 0.8260(3) 0.0290(7) Uani 1 1 d . . . O2 O -0.0098(3) 0.3165(3) 0.8902(2) 0.0232(7) Uani 1 1 d . . . O3 O 0.1548(3) 0.4501(2) 1.0279(2) 0.0190(6) Uani 1 1 d . . . O4 O -0.0296(3) 0.5580(3) 0.8593(2) 0.0195(6) Uani 1 1 d . . . O5 O -0.0140(3) 0.6211(3) 1.0519(2) 0.0192(6) Uani 1 1 d . . . H5 H -0.0858 0.6782 1.0244 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C3 0.028(2) 0.024(2) 0.033(2) 0.0071(19) -0.004(2) 0.009(2) C4 0.029(2) 0.031(3) 0.029(2) 0.010(2) -0.0104(19) -0.009(2) C5 0.032(3) 0.036(3) 0.019(2) -0.0119(19) -0.0078(18) 0.010(2) Cl1 0.0211(5) 0.0188(5) 0.0286(5) 0.0063(4) 0.0007(4) -0.0022(4) Cl2 0.0149(5) 0.0343(6) 0.0366(6) 0.0064(5) -0.0011(4) -0.0028(4) Cl3 0.0251(5) 0.0282(6) 0.0415(6) 0.0092(5) -0.0143(5) -0.0112(5) Cl4 0.0305(6) 0.0347(6) 0.0232(5) 0.0104(5) 0.0068(4) 0.0033(5) Mo1 0.01311(16) 0.01600(17) 0.02010(17) 0.00171(14) 0.00072(12) -0.00061(14) Mo2 0.01523(16) 0.01546(17) 0.01545(16) 0.00039(13) 0.00060(12) -0.00202(14) O1 0.0262(17) 0.0265(16) 0.0344(17) -0.0010(13) 0.0075(14) -0.0005(14) O2 0.0282(17) 0.0187(15) 0.0227(16) -0.0049(11) 0.0036(12) -0.0068(13) O3 0.0170(13) 0.0165(14) 0.0234(14) 0.0027(11) -0.0001(12) 0.0024(11) O4 0.0189(14) 0.0222(15) 0.0174(13) 0.0050(11) -0.0026(11) -0.0015(13) O5 0.0185(14) 0.0208(14) 0.0183(15) -0.0041(11) -0.0060(11) 0.0062(12) _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 C3 O3 1.431(5) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 O4 1.444(5) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 O5 1.458(5) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? Cl1 Mo1 2.3401(12) . ? Cl2 Mo2 2.3381(12) . ? Cl3 Mo1 2.3609(12) . ? Cl4 Mo2 2.3431(12) . ? Mo1 O1 1.662(3) . ? Mo1 O4 2.007(3) . ? Mo1 O3 2.018(3) . ? Mo1 O5 2.475(3) . ? Mo1 Mo2 2.6839(7) . ? Mo2 O2 1.658(3) . ? Mo2 O3 2.013(3) . ? Mo2 O4 2.024(3) . ? Mo2 O5 2.442(3) . ? O5 H5 1.0000 . ? 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 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 . . ? O4 C4 H4A 109.5 . . ? O4 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O4 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O5 C5 H5A 109.5 . . ? O5 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O5 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O1 Mo1 O4 99.67(15) . . ? O1 Mo1 O3 97.86(14) . . ? O4 Mo1 O3 96.68(12) . . ? O1 Mo1 Cl1 103.63(12) . . ? O4 Mo1 Cl1 85.75(9) . . ? O3 Mo1 Cl1 157.66(9) . . ? O1 Mo1 Cl3 104.32(13) . . ? O4 Mo1 Cl3 155.86(9) . . ? O3 Mo1 Cl3 82.82(9) . . ? Cl1 Mo1 Cl3 86.02(4) . . ? O1 Mo1 O5 158.79(14) . . ? O4 Mo1 O5 68.09(11) . . ? O3 Mo1 O5 67.77(11) . . ? Cl1 Mo1 O5 92.97(7) . . ? Cl3 Mo1 O5 89.74(8) . . ? O1 Mo1 Mo2 102.49(12) . . ? O4 Mo1 Mo2 48.52(8) . . ? O3 Mo1 Mo2 48.17(8) . . ? Cl1 Mo1 Mo2 130.31(3) . . ? Cl3 Mo1 Mo2 126.56(4) . . ? O5 Mo1 Mo2 56.34(7) . . ? O2 Mo2 O3 98.08(14) . . ? O2 Mo2 O4 98.18(13) . . ? O3 Mo2 O4 96.31(11) . . ? O2 Mo2 Cl2 104.71(12) . . ? O3 Mo2 Cl2 156.70(9) . . ? O4 Mo2 Cl2 85.29(9) . . ? O2 Mo2 Cl4 102.77(11) . . ? O3 Mo2 Cl4 83.79(9) . . ? O4 Mo2 Cl4 158.84(9) . . ? Cl2 Mo2 Cl4 86.53(4) . . ? O2 Mo2 O5 158.98(13) . . ? O3 Mo2 O5 68.54(10) . . ? O4 Mo2 O5 68.55(11) . . ? Cl2 Mo2 O5 90.77(7) . . ? Cl4 Mo2 O5 92.11(8) . . ? O2 Mo2 Mo1 101.48(11) . . ? O3 Mo2 Mo1 48.34(8) . . ? O4 Mo2 Mo1 47.97(8) . . ? Cl2 Mo2 Mo1 129.04(4) . . ? Cl4 Mo2 Mo1 128.66(3) . . ? O5 Mo2 Mo1 57.51(7) . . ? C3 O3 Mo2 135.2(3) . . ? C3 O3 Mo1 133.5(3) . . ? Mo2 O3 Mo1 83.49(11) . . ? C4 O4 Mo1 139.0(3) . . ? C4 O4 Mo2 136.5(3) . . ? Mo1 O4 Mo2 83.51(11) . . ? C5 O5 Mo2 126.1(3) . . ? C5 O5 Mo1 123.8(3) . . ? Mo2 O5 Mo1 66.16(7) . . ? C5 O5 H5 111.2 . . ? Mo2 O5 H5 111.2 . . ? Mo1 O5 H5 111.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Mo1 Mo2 O2 -1.23(17) . . . . ? O4 Mo1 Mo2 O2 90.71(16) . . . . ? O3 Mo1 Mo2 O2 -90.65(16) . . . . ? Cl1 Mo1 Mo2 O2 119.06(12) . . . . ? Cl3 Mo1 Mo2 O2 -119.88(12) . . . . ? O5 Mo1 Mo2 O2 -179.84(14) . . . . ? O1 Mo1 Mo2 O3 89.41(16) . . . . ? O4 Mo1 Mo2 O3 -178.65(15) . . . . ? Cl1 Mo1 Mo2 O3 -150.29(12) . . . . ? Cl3 Mo1 Mo2 O3 -29.24(12) . . . . ? O5 Mo1 Mo2 O3 -89.20(14) . . . . ? O1 Mo1 Mo2 O4 -91.94(17) . . . . ? O3 Mo1 Mo2 O4 178.65(15) . . . . ? Cl1 Mo1 Mo2 O4 28.35(12) . . . . ? Cl3 Mo1 Mo2 O4 149.41(12) . . . . ? O5 Mo1 Mo2 O4 89.45(14) . . . . ? O1 Mo1 Mo2 Cl2 -121.12(13) . . . . ? O4 Mo1 Mo2 Cl2 -29.18(12) . . . . ? O3 Mo1 Mo2 Cl2 149.47(12) . . . . ? Cl1 Mo1 Mo2 Cl2 -0.83(6) . . . . ? Cl3 Mo1 Mo2 Cl2 120.23(6) . . . . ? O5 Mo1 Mo2 Cl2 60.27(9) . . . . ? O1 Mo1 Mo2 Cl4 115.59(13) . . . . ? O4 Mo1 Mo2 Cl4 -152.47(12) . . . . ? O3 Mo1 Mo2 Cl4 26.18(12) . . . . ? Cl1 Mo1 Mo2 Cl4 -124.11(6) . . . . ? Cl3 Mo1 Mo2 Cl4 -3.06(6) . . . . ? O5 Mo1 Mo2 Cl4 -63.02(9) . . . . ? O1 Mo1 Mo2 O5 178.61(15) . . . . ? O4 Mo1 Mo2 O5 -89.45(14) . . . . ? O3 Mo1 Mo2 O5 89.20(14) . . . . ? Cl1 Mo1 Mo2 O5 -61.10(9) . . . . ? Cl3 Mo1 Mo2 O5 59.96(9) . . . . ? O2 Mo2 O3 C3 -52.0(4) . . . . ? O4 Mo2 O3 C3 -151.2(4) . . . . ? Cl2 Mo2 O3 C3 116.0(4) . . . . ? Cl4 Mo2 O3 C3 50.1(4) . . . . ? O5 Mo2 O3 C3 144.8(4) . . . . ? Mo1 Mo2 O3 C3 -150.2(4) . . . . ? O2 Mo2 O3 Mo1 98.21(13) . . . . ? O4 Mo2 O3 Mo1 -1.01(11) . . . . ? Cl2 Mo2 O3 Mo1 -93.7(2) . . . . ? Cl4 Mo2 O3 Mo1 -159.72(9) . . . . ? O5 Mo2 O3 Mo1 -64.99(10) . . . . ? O1 Mo1 O3 C3 51.4(4) . . . . ? O4 Mo1 O3 C3 152.1(4) . . . . ? Cl1 Mo1 O3 C3 -112.8(4) . . . . ? Cl3 Mo1 O3 C3 -52.2(4) . . . . ? O5 Mo1 O3 C3 -144.8(4) . . . . ? Mo2 Mo1 O3 C3 151.1(4) . . . . ? O1 Mo1 O3 Mo2 -99.75(14) . . . . ? O4 Mo1 O3 Mo2 1.02(11) . . . . ? Cl1 Mo1 O3 Mo2 96.1(2) . . . . ? Cl3 Mo1 O3 Mo2 156.71(9) . . . . ? O5 Mo1 O3 Mo2 64.04(10) . . . . ? O1 Mo1 O4 C4 -71.0(4) . . . . ? O3 Mo1 O4 C4 -170.2(4) . . . . ? Cl1 Mo1 O4 C4 32.1(4) . . . . ? Cl3 Mo1 O4 C4 102.4(4) . . . . ? O5 Mo1 O4 C4 127.0(4) . . . . ? Mo2 Mo1 O4 C4 -169.2(5) . . . . ? O1 Mo1 O4 Mo2 98.17(14) . . . . ? O3 Mo1 O4 Mo2 -1.02(11) . . . . ? Cl1 Mo1 O4 Mo2 -158.71(9) . . . . ? Cl3 Mo1 O4 Mo2 -88.3(2) . . . . ? O5 Mo1 O4 Mo2 -63.78(10) . . . . ? O2 Mo2 O4 C4 71.6(4) . . . . ? O3 Mo2 O4 C4 170.7(4) . . . . ? Cl2 Mo2 O4 C4 -32.6(4) . . . . ? Cl4 Mo2 O4 C4 -100.2(4) . . . . ? O5 Mo2 O4 C4 -125.3(4) . . . . ? Mo1 Mo2 O4 C4 169.7(5) . . . . ? O2 Mo2 O4 Mo1 -98.11(14) . . . . ? O3 Mo2 O4 Mo1 1.02(11) . . . . ? Cl2 Mo2 O4 Mo1 157.67(9) . . . . ? Cl4 Mo2 O4 Mo1 90.1(2) . . . . ? O5 Mo2 O4 Mo1 64.98(10) . . . . ? O2 Mo2 O5 C5 -115.1(4) . . . . ? O3 Mo2 O5 C5 -62.2(3) . . . . ? O4 Mo2 O5 C5 -168.5(3) . . . . ? Cl2 Mo2 O5 C5 106.9(3) . . . . ? Cl4 Mo2 O5 C5 20.3(3) . . . . ? Mo1 Mo2 O5 C5 -115.5(3) . . . . ? O2 Mo2 O5 Mo1 0.4(4) . . . . ? O3 Mo2 O5 Mo1 53.39(10) . . . . ? O4 Mo2 O5 Mo1 -52.95(9) . . . . ? Cl2 Mo2 O5 Mo1 -137.58(5) . . . . ? Cl4 Mo2 O5 Mo1 135.87(5) . . . . ? O1 Mo1 O5 C5 114.9(5) . . . . ? O4 Mo1 O5 C5 172.5(3) . . . . ? O3 Mo1 O5 C5 65.1(3) . . . . ? Cl1 Mo1 O5 C5 -103.3(3) . . . . ? Cl3 Mo1 O5 C5 -17.3(3) . . . . ? Mo2 Mo1 O5 C5 118.7(3) . . . . ? O1 Mo1 O5 Mo2 -3.7(4) . . . . ? O4 Mo1 O5 Mo2 53.85(10) . . . . ? O3 Mo1 O5 Mo2 -53.60(9) . . . . ? Cl1 Mo1 O5 Mo2 138.06(5) . . . . ? Cl3 Mo1 O5 Mo2 -135.94(5) . . . . ? 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 O5 H5 Cl3 1.00 2.17 3.103(3) 153.6 4_467 O5 H5 Cl1 1.00 2.97 3.570(3) 119.3 4_467 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.095 _refine_diff_density_min -0.648 _refine_diff_density_rms 0.112 _database_code_depnum_ccdc_archive 'CCDC 943838' ####################################################################### # # 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_p21c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H8 Cl3 Mo O3' _chemical_formula_weight 282.37 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' Mo Mo -1.6832 0.6857 '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)/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 13.933(4) _cell_length_b 5.5881(16) _cell_length_c 11.777(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.954(3) _cell_angle_gamma 90.00 _cell_volume 861.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4586 _cell_measurement_theta_min 3.111 _cell_measurement_theta_max 28.5035 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.176 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 2.395 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6209 _exptl_absorpt_correction_T_max 0.7304 _exptl_absorpt_process_details ; Data were corrected for Lorentz polarization and absorption effects (empirical absorption correction SADABS). R(int) = 0.1394 (selected reflections only, before parameter refinement) R(int) = 0.0402 (selected reflections only, after parameter refinement) ; _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 6548 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 26.99 _reflns_number_total 1871 _reflns_number_gt 1773 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1996)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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. The following restraints were applied (given as SHELXL lines): DFIX 0.89 0.02 O3 H3 O2 H2 ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+1.1368P] 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 1871 _refine_ls_number_parameters 88 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0250 _refine_ls_R_factor_gt 0.0230 _refine_ls_wR_factor_ref 0.0568 _refine_ls_wR_factor_gt 0.0559 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.137 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mo1 Mo 0.227485(16) 0.17710(4) 0.309389(19) 0.01422(8) Uani 1 1 d . . . Cl1 Cl 0.35379(5) 0.03943(12) 0.48528(6) 0.02066(15) Uani 1 1 d . . . Cl2 Cl 0.13403(5) 0.42012(12) 0.14437(6) 0.02004(15) Uani 1 1 d . . . Cl3 Cl 0.30613(5) -0.03081(12) 0.18864(6) 0.01863(14) Uani 1 1 d . . . O1 O 0.13654(15) -0.0186(4) 0.30247(18) 0.0244(4) Uani 1 1 d . . . O2 O 0.18844(14) 0.4246(4) 0.42044(17) 0.0203(4) Uani 1 1 d D . . H2 H 0.223(2) 0.426(6) 0.4956(18) 0.030 Uiso 1 1 d D . . O3 O 0.34526(14) 0.4658(3) 0.32379(18) 0.0201(4) Uani 1 1 d D . . H3 H 0.323(3) 0.590(5) 0.282(3) 0.030 Uiso 1 1 d D . . C2 C 0.0858(2) 0.5037(6) 0.4066(3) 0.0225(6) Uani 1 1 d . . . H2A H 0.0886 0.6195 0.4701 0.034 Uiso 1 1 calc R . . H2B H 0.0445 0.3657 0.4129 0.034 Uiso 1 1 calc R . . H2C H 0.0550 0.5792 0.3273 0.034 Uiso 1 1 calc R . . C3 C 0.4519(2) 0.4502(5) 0.3370(3) 0.0222(6) Uani 1 1 d . . . H3A H 0.4799 0.6116 0.3391 0.033 Uiso 1 1 calc R . . H3B H 0.4591 0.3617 0.2686 0.033 Uiso 1 1 calc R . . H3C H 0.4890 0.3665 0.4124 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mo1 0.01103(12) 0.01871(13) 0.01359(13) 0.00108(8) 0.00507(9) -0.00007(8) Cl1 0.0179(3) 0.0265(3) 0.0166(3) 0.0042(3) 0.0046(2) 0.0040(2) Cl2 0.0183(3) 0.0249(3) 0.0158(3) 0.0024(3) 0.0042(2) 0.0034(2) Cl3 0.0195(3) 0.0208(3) 0.0172(3) 0.0002(2) 0.0083(2) 0.0030(2) O1 0.0178(10) 0.0295(11) 0.0259(11) 0.0037(9) 0.0074(8) -0.0040(8) O2 0.0146(9) 0.0309(11) 0.0160(9) -0.0013(8) 0.0060(8) 0.0047(8) O3 0.0139(9) 0.0197(10) 0.0290(11) 0.0043(8) 0.0102(8) 0.0012(7) C2 0.0139(12) 0.0325(15) 0.0250(14) 0.0034(12) 0.0114(11) 0.0061(11) C3 0.0141(12) 0.0300(15) 0.0242(14) 0.0008(12) 0.0087(11) -0.0018(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mo1 O1 1.654(2) . ? Mo1 O2 2.099(2) . ? Mo1 O3 2.2658(19) . ? Mo1 Cl1 2.3434(8) . ? Mo1 Cl2 2.3642(8) . ? Mo1 Cl3 2.3741(8) . ? O2 C2 1.452(3) . ? O2 H2 0.852(18) . ? O3 C3 1.442(3) . ? O3 H3 0.845(18) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mo1 O2 96.27(9) . . ? O1 Mo1 O3 175.66(9) . . ? O2 Mo1 O3 79.59(8) . . ? O1 Mo1 Cl1 99.10(7) . . ? O2 Mo1 Cl1 86.66(6) . . ? O3 Mo1 Cl1 82.03(5) . . ? O1 Mo1 Cl2 98.13(7) . . ? O2 Mo1 Cl2 86.93(6) . . ? O3 Mo1 Cl2 80.46(5) . . ? Cl1 Mo1 Cl2 162.17(3) . . ? O1 Mo1 Cl3 98.59(8) . . ? O2 Mo1 Cl3 165.13(6) . . ? O3 Mo1 Cl3 85.57(5) . . ? Cl1 Mo1 Cl3 90.45(3) . . ? Cl2 Mo1 Cl3 91.49(3) . . ? C2 O2 Mo1 125.82(17) . . ? C2 O2 H2 108(2) . . ? Mo1 O2 H2 118(2) . . ? C3 O3 Mo1 131.14(17) . . ? C3 O3 H3 105(2) . . ? Mo1 O3 H3 116(2) . . ? O2 C2 H2A 109.5 . . ? O2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? O2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? 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 . . ? 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 Mo1 O2 C2 -44.3(2) . . . . ? O3 Mo1 O2 C2 134.4(2) . . . . ? Cl1 Mo1 O2 C2 -143.1(2) . . . . ? Cl2 Mo1 O2 C2 53.5(2) . . . . ? Cl3 Mo1 O2 C2 137.8(2) . . . . ? O1 Mo1 O3 C3 157.4(11) . . . . ? O2 Mo1 O3 C3 140.0(2) . . . . ? Cl1 Mo1 O3 C3 52.0(2) . . . . ? Cl2 Mo1 O3 C3 -131.4(2) . . . . ? Cl3 Mo1 O3 C3 -39.1(2) . . . . ? 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 O2 H2 Cl3 0.852(18) 2.25(2) 3.079(2) 165(3) 4_566 O3 H3 Cl3 0.845(18) 2.36(2) 3.186(2) 165(3) 1_565 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.537 _refine_diff_density_min -1.085 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 943839' ####################################################################### # # 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_pnma _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H12 Cl4 Mo O2' _chemical_formula_weight 341.89 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' Mo Mo -1.6832 0.6857 '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 11.1285(8) _cell_length_b 8.9787(7) _cell_length_c 11.7001(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1169.07(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3739 _cell_measurement_theta_min 2.526 _cell_measurement_theta_max 25.615 _exptl_crystal_description plate _exptl_crystal_colour bright-orange _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.942 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 1.999 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7404 _exptl_absorpt_correction_T_max 0.8251 _exptl_absorpt_process_details ; Data were corrected for Lorentz polarization and absorption effects (empirical absorption correction SADABS). R(int) = 0.0868 (selected reflections only, before parameter refinement) R(int) = 0.0420 (selected reflections only, after parameter refinement) ; _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 11125 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1120 _reflns_number_gt 1007 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1996)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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. The following restraints were applied (given as SHELXL lines): simu .01 c1 > c5 simu .01 $cl isor .01 cl1 > c5 dfix 1.43 .01 c1 o1 o1 c2 c4 o2 o2 c5 dfix 1.53 .01 c2 c4 c2 c3 ; _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^+48.6585P] 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 1120 _refine_ls_number_parameters 101 _refine_ls_number_restraints 108 _refine_ls_R_factor_all 0.1023 _refine_ls_R_factor_gt 0.0954 _refine_ls_wR_factor_ref 0.2055 _refine_ls_wR_factor_gt 0.2021 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.194 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mo1 Mo 0.73615(14) 0.2500 0.50415(14) 0.0327(5) Uani 1 2 d S . . Cl1 Cl 0.6303(6) 0.2500 0.6728(5) 0.090(3) Uani 1 2 d SU A . Cl2 Cl 0.8344(5) 0.2500 0.3275(4) 0.0410(12) Uani 1 2 d SU A . Cl3 Cl 0.6137(15) 0.4402(16) 0.4474(11) 0.054(3) Uani 0.50 1 d PU A -1 Cl4 Cl 0.8755(9) 0.3955(12) 0.5837(8) 0.065(2) Uani 0.50 1 d PU A -1 C1 C 0.898(3) 0.026(4) 0.651(2) 0.049(7) Uani 0.50 1 d PDU A -1 H1A H 0.9385 0.1205 0.6666 0.073 Uiso 0.50 1 calc PR A -1 H1B H 0.9580 -0.0532 0.6420 0.073 Uiso 0.50 1 calc PR A -1 H1C H 0.8449 0.0010 0.7154 0.073 Uiso 0.50 1 calc PR A -1 O1 O 0.8281(17) 0.038(2) 0.5485(16) 0.042(4) Uani 0.50 1 d PDU A -1 C2 C 0.753(2) -0.087(2) 0.528(2) 0.053(5) Uani 0.50 1 d PDU A -1 H2 H 0.6963 -0.1032 0.5929 0.063 Uiso 0.50 1 calc PR A -1 C3 C 0.830(3) -0.226(4) 0.508(3) 0.066(8) Uani 0.50 1 d PDU A -1 H3A H 0.8820 -0.2421 0.5742 0.099 Uiso 0.50 1 calc PR A -1 H3B H 0.8790 -0.2123 0.4393 0.099 Uiso 0.50 1 calc PR A -1 H3C H 0.7773 -0.3129 0.4977 0.099 Uiso 0.50 1 calc PR A -1 C4 C 0.683(3) -0.060(4) 0.417(2) 0.051(5) Uani 0.50 1 d PDU A -1 H4A H 0.7384 -0.0559 0.3510 0.062 Uiso 0.50 1 calc PR A -1 H4B H 0.6247 -0.1422 0.4038 0.062 Uiso 0.50 1 calc PR A -1 O2 O 0.621(4) 0.078(4) 0.430(3) 0.054(7) Uani 0.50 1 d PDU A -1 C5 C 0.545(3) 0.119(4) 0.336(3) 0.057(7) Uani 0.50 1 d PDU A -1 H5A H 0.4997 0.2093 0.3563 0.086 Uiso 0.50 1 calc PR A -1 H5B H 0.4889 0.0381 0.3194 0.086 Uiso 0.50 1 calc PR A -1 H5C H 0.5944 0.1394 0.2684 0.086 Uiso 0.50 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mo1 0.0317(8) 0.0397(9) 0.0268(8) 0.000 0.0050(7) 0.000 Cl1 0.060(4) 0.174(8) 0.035(3) 0.000 0.010(3) 0.000 Cl2 0.039(2) 0.051(3) 0.033(2) 0.000 0.013(2) 0.000 Cl3 0.060(5) 0.054(6) 0.047(5) 0.011(5) 0.001(4) 0.016(5) Cl4 0.072(5) 0.058(5) 0.063(5) 0.001(5) 0.003(4) -0.004(5) C1 0.053(9) 0.047(10) 0.047(9) 0.002(8) -0.008(8) 0.004(8) O1 0.042(7) 0.039(7) 0.045(7) 0.003(6) -0.004(6) -0.004(6) C2 0.055(7) 0.048(7) 0.056(7) 0.004(6) -0.004(6) -0.004(6) C3 0.067(10) 0.064(12) 0.066(10) -0.002(9) -0.007(8) 0.003(9) C4 0.050(7) 0.051(8) 0.053(7) 0.000(6) -0.002(6) -0.006(6) O2 0.058(9) 0.051(9) 0.051(9) 0.003(7) -0.003(7) -0.010(7) C5 0.059(10) 0.061(11) 0.052(10) 0.001(8) -0.006(8) -0.003(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mo1 O2 2.19(5) . ? Mo1 O2 2.19(5) 7_565 ? Mo1 O1 2.22(2) 7_565 ? Mo1 O1 2.22(2) . ? Mo1 Cl4 2.231(10) . ? Mo1 Cl4 2.231(10) 7_565 ? Mo1 Cl3 2.283(16) 7_565 ? Mo1 Cl3 2.283(16) . ? Mo1 Cl1 2.299(6) . ? Mo1 Cl2 2.339(5) . ? C1 O1 1.437(10) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O1 C2 1.427(10) . ? C2 C3 1.529(10) . ? C2 C4 1.530(10) . ? C2 H2 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 O2 1.428(10) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? O2 C5 1.432(10) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Mo1 O2 89.8(14) . 7_565 ? O2 Mo1 O1 165.3(9) . 7_565 ? O2 Mo1 O1 76.1(9) 7_565 7_565 ? O2 Mo1 O1 76.1(9) . . ? O2 Mo1 O1 165.3(9) 7_565 . ? O1 Mo1 O1 117.8(10) 7_565 . ? O2 Mo1 Cl4 170.6(8) . . ? O2 Mo1 Cl4 99.2(8) 7_565 . ? O1 Mo1 Cl4 23.2(5) 7_565 . ? O1 Mo1 Cl4 94.8(6) . . ? O2 Mo1 Cl4 99.2(8) . 7_565 ? O2 Mo1 Cl4 170.6(8) 7_565 7_565 ? O1 Mo1 Cl4 94.8(6) 7_565 7_565 ? O1 Mo1 Cl4 23.2(5) . 7_565 ? Cl4 Mo1 Cl4 71.7(6) . 7_565 ? O2 Mo1 Cl3 6.7(14) . 7_565 ? O2 Mo1 Cl3 93.6(6) 7_565 7_565 ? O1 Mo1 Cl3 169.5(6) 7_565 7_565 ? O1 Mo1 Cl3 72.7(6) . 7_565 ? Cl4 Mo1 Cl3 166.9(4) . 7_565 ? Cl4 Mo1 Cl3 95.7(4) 7_565 7_565 ? O2 Mo1 Cl3 93.6(6) . . ? O2 Mo1 Cl3 6.7(14) 7_565 . ? O1 Mo1 Cl3 72.7(6) 7_565 . ? O1 Mo1 Cl3 169.5(6) . . ? Cl4 Mo1 Cl3 95.7(4) . . ? Cl4 Mo1 Cl3 166.9(4) 7_565 . ? Cl3 Mo1 Cl3 96.8(7) 7_565 . ? O2 Mo1 Cl1 92.4(12) . . ? O2 Mo1 Cl1 92.4(12) 7_565 . ? O1 Mo1 Cl1 92.0(5) 7_565 . ? O1 Mo1 Cl1 92.0(5) . . ? Cl4 Mo1 Cl1 89.9(3) . . ? Cl4 Mo1 Cl1 89.9(3) 7_565 . ? Cl3 Mo1 Cl1 86.8(4) 7_565 . ? Cl3 Mo1 Cl1 86.8(4) . . ? O2 Mo1 Cl2 85.5(12) . . ? O2 Mo1 Cl2 85.5(12) 7_565 . ? O1 Mo1 Cl2 89.5(5) 7_565 . ? O1 Mo1 Cl2 89.5(5) . . ? Cl4 Mo1 Cl2 92.5(3) . . ? Cl4 Mo1 Cl2 92.5(3) 7_565 . ? Cl3 Mo1 Cl2 91.3(4) 7_565 . ? Cl3 Mo1 Cl2 91.3(4) . . ? Cl1 Mo1 Cl2 177.0(2) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 O1 C1 113(2) . . ? C2 O1 Mo1 111.5(14) . . ? C1 O1 Mo1 120.9(19) . . ? O1 C2 C3 110(2) . . ? O1 C2 C4 109(2) . . ? C3 C2 C4 107(2) . . ? O1 C2 H2 110.5 . . ? C3 C2 H2 110.5 . . ? C4 C2 H2 110.5 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O2 C4 C2 107(2) . . ? O2 C4 H4A 110.3 . . ? C2 C4 H4A 110.3 . . ? O2 C4 H4B 110.3 . . ? C2 C4 H4B 110.3 . . ? H4A C4 H4B 108.5 . . ? C4 O2 C5 116(3) . . ? C4 O2 Mo1 112(3) . . ? C5 O2 Mo1 118(3) . . ? O2 C5 H5A 109.5 . . ? O2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? 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 Mo1 O1 C2 -12(2) . . . . ? O2 Mo1 O1 C2 -28(6) 7_565 . . . ? O1 Mo1 O1 C2 173.1(13) 7_565 . . . ? Cl4 Mo1 O1 C2 169.7(17) . . . . ? Cl4 Mo1 O1 C2 165(3) 7_565 . . . ? Cl3 Mo1 O1 C2 -6.3(16) 7_565 . . . ? Cl3 Mo1 O1 C2 -4(5) . . . . ? Cl1 Mo1 O1 C2 79.7(17) . . . . ? Cl2 Mo1 O1 C2 -97.8(17) . . . . ? O2 Mo1 O1 C1 -150(2) . . . . ? O2 Mo1 O1 C1 -165(5) 7_565 . . . ? O1 Mo1 O1 C1 36(2) 7_565 . . . ? Cl4 Mo1 O1 C1 32(2) . . . . ? Cl4 Mo1 O1 C1 27.4(18) 7_565 . . . ? Cl3 Mo1 O1 C1 -144(2) 7_565 . . . ? Cl3 Mo1 O1 C1 -141(3) . . . . ? Cl1 Mo1 O1 C1 -58(2) . . . . ? Cl2 Mo1 O1 C1 125(2) . . . . ? C1 O1 C2 C3 -64(3) . . . . ? Mo1 O1 C2 C3 155.5(18) . . . . ? C1 O1 C2 C4 180(2) . . . . ? Mo1 O1 C2 C4 39(3) . . . . ? O1 C2 C4 O2 -55(4) . . . . ? C3 C2 C4 O2 -174(3) . . . . ? C2 C4 O2 C5 -177(3) . . . . ? C2 C4 O2 Mo1 44(3) . . . . ? O2 Mo1 O2 C4 157.4(18) 7_565 . . . ? O1 Mo1 O2 C4 142(3) 7_565 . . . ? O1 Mo1 O2 C4 -19(3) . . . . ? Cl4 Mo1 O2 C4 -6(10) . . . . ? Cl4 Mo1 O2 C4 -20(3) 7_565 . . . ? Cl3 Mo1 O2 C4 -78(9) 7_565 . . . ? Cl3 Mo1 O2 C4 163(3) . . . . ? Cl1 Mo1 O2 C4 -110(3) . . . . ? Cl2 Mo1 O2 C4 72(3) . . . . ? O2 Mo1 O2 C5 20(4) 7_565 . . . ? O1 Mo1 O2 C5 5(8) 7_565 . . . ? O1 Mo1 O2 C5 -156(3) . . . . ? Cl4 Mo1 O2 C5 -144(5) . . . . ? Cl4 Mo1 O2 C5 -158(3) 7_565 . . . ? Cl3 Mo1 O2 C5 144(13) 7_565 . . . ? Cl3 Mo1 O2 C5 25(3) . . . . ? Cl1 Mo1 O2 C5 112(3) . . . . ? Cl2 Mo1 O2 C5 -66(3) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.931 _refine_diff_density_min -1.816 _refine_diff_density_rms 0.245 _database_code_depnum_ccdc_archive 'CCDC 943837' ####################################################################### # # 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_pca21 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H9 Cl4 Mo O3' _chemical_formula_weight 342.85 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' Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 13.339(2) _cell_length_b 6.5492(12) _cell_length_c 12.360(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1079.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6381 _cell_measurement_theta_min 2.2465 _cell_measurement_theta_max 28.675 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 2.171 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6585 _exptl_absorpt_correction_T_max 0.7366 _exptl_absorpt_process_details ; Data were corrected for Lorentz polarization and absorption effects (empirical absorption correction SADABS). R(int) = 0.1716 (selected reflections only, before parameter refinement) R(int) = 0.0723 (selected reflections only, after parameter refinement) ; _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 7795 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.99 _reflns_number_total 2519 _reflns_number_gt 2495 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1996)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0267P)^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 0.01(5) _refine_ls_number_reflns 2519 _refine_ls_number_parameters 109 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0237 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0565 _refine_ls_wR_factor_gt 0.0564 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.6494(2) 0.3411(4) 0.2359(2) 0.0241(6) Uani 1 1 d . . . H1A H 0.5855 0.2796 0.2145 0.036 Uiso 1 1 calc R . . H1B H 0.6933 0.2356 0.2661 0.036 Uiso 1 1 calc R . . H1C H 0.6815 0.4024 0.1724 0.036 Uiso 1 1 calc R . . C2 C 0.72505(18) 0.5923(4) 0.3516(2) 0.0177(5) Uani 1 1 d . . . H2A H 0.7546 0.6721 0.2915 0.021 Uiso 1 1 calc R . . H2B H 0.7737 0.4861 0.3737 0.021 Uiso 1 1 calc R . . C3 C 0.7017(2) 0.7293(4) 0.4450(2) 0.0182(5) Uani 1 1 d . . . H3A H 0.6752 0.6490 0.5065 0.022 Uiso 1 1 calc R . . H3B H 0.7629 0.8020 0.4690 0.022 Uiso 1 1 calc R . . C4 C 0.5955(2) 1.0100(4) 0.4901(2) 0.0209(6) Uani 1 1 d . . . H4A H 0.5752 0.9309 0.5547 0.025 Uiso 1 1 calc R . . H4B H 0.5368 1.0897 0.4651 0.025 Uiso 1 1 calc R . . Cl2 Cl 0.40533(4) 0.99060(10) 0.30029(6) 0.02276(14) Uani 1 1 d . . . Cl3 Cl 0.69533(6) 1.17918(10) 0.52435(6) 0.02430(15) Uani 1 1 d . . . Cl4 Cl 0.60356(5) 0.84738(9) 0.15665(5) 0.01636(12) Uani 1 1 d . . . Cl5 Cl 0.45311(5) 0.59753(10) 0.46718(5) 0.02153(14) Uani 1 1 d . . . Mo1 Mo 0.505561(13) 0.70105(3) 0.29379(3) 0.01256(7) Uani 1 1 d . . . O1 O 0.43692(14) 0.5379(3) 0.22166(16) 0.0195(4) Uani 1 1 d . . . O2 O 0.63154(12) 0.4983(3) 0.31705(14) 0.0147(4) Uani 1 1 d . . . O3 O 0.62681(14) 0.8742(3) 0.40691(15) 0.0147(4) 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 0.0326(16) 0.0196(12) 0.0202(15) -0.0071(11) -0.0034(12) 0.0077(11) C2 0.0101(11) 0.0222(12) 0.0207(14) 0.0008(10) -0.0028(10) 0.0012(9) C3 0.0179(13) 0.0205(11) 0.0163(14) 0.0003(10) -0.0071(10) 0.0017(9) C4 0.0194(13) 0.0245(13) 0.0187(14) -0.0114(11) 0.0007(11) -0.0004(9) Cl2 0.0211(3) 0.0268(3) 0.0204(3) -0.0032(3) -0.0012(3) 0.0102(2) Cl3 0.0335(4) 0.0191(3) 0.0203(3) -0.0038(3) -0.0077(3) -0.0042(2) Cl4 0.0200(3) 0.0171(2) 0.0120(3) 0.0008(2) 0.0024(2) -0.0007(2) Cl5 0.0168(3) 0.0358(3) 0.0119(3) 0.0039(3) 0.0012(2) -0.0047(2) Mo1 0.01166(11) 0.01616(11) 0.00984(11) -0.00033(10) -0.00020(9) 0.00012(6) O1 0.0178(9) 0.0225(9) 0.0183(9) 0.0005(8) -0.0009(8) -0.0049(7) O2 0.0141(8) 0.0160(8) 0.0140(10) -0.0018(6) -0.0012(7) 0.0023(6) O3 0.0153(8) 0.0182(8) 0.0106(8) -0.0043(7) -0.0009(7) 0.0013(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 O2 1.457(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O2 1.455(3) . ? C2 C3 1.494(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O3 1.456(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O3 1.422(3) . ? C4 Cl3 1.784(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? Cl2 Mo1 2.3216(7) . ? Cl4 Mo1 2.3453(7) . ? Cl5 Mo1 2.3541(8) . ? Mo1 O1 1.6659(19) . ? Mo1 O2 2.1610(17) . ? Mo1 O3 2.4199(19) . ? 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 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C3 107.6(2) . . ? O2 C2 H2A 110.2 . . ? C3 C2 H2A 110.2 . . ? O2 C2 H2B 110.2 . . ? C3 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? O3 C3 C2 106.5(2) . . ? O3 C3 H3A 110.4 . . ? C2 C3 H3A 110.4 . . ? O3 C3 H3B 110.4 . . ? C2 C3 H3B 110.4 . . ? H3A C3 H3B 108.6 . . ? O3 C4 Cl3 109.94(18) . . ? O3 C4 H4A 109.7 . . ? Cl3 C4 H4A 109.7 . . ? O3 C4 H4B 109.7 . . ? Cl3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? O1 Mo1 O2 95.99(8) . . ? O1 Mo1 Cl2 103.06(7) . . ? O2 Mo1 Cl2 160.93(5) . . ? O1 Mo1 Cl4 100.47(7) . . ? O2 Mo1 Cl4 85.05(5) . . ? Cl2 Mo1 Cl4 90.70(3) . . ? O1 Mo1 Cl5 97.99(7) . . ? O2 Mo1 Cl5 86.16(5) . . ? Cl2 Mo1 Cl5 91.87(3) . . ? Cl4 Mo1 Cl5 160.27(3) . . ? O1 Mo1 O3 167.70(8) . . ? O2 Mo1 O3 72.02(6) . . ? Cl2 Mo1 O3 88.98(5) . . ? Cl4 Mo1 O3 81.58(5) . . ? Cl5 Mo1 O3 78.91(5) . . ? C2 O2 C1 111.1(2) . . ? C2 O2 Mo1 116.46(15) . . ? C1 O2 Mo1 118.03(16) . . ? C4 O3 C3 112.1(2) . . ? C4 O3 Mo1 120.95(15) . . ? C3 O3 Mo1 109.89(14) . . ? 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 O3 -57.3(2) . . . . ? C3 C2 O2 C1 -172.2(2) . . . . ? C3 C2 O2 Mo1 48.7(2) . . . . ? O1 Mo1 O2 C2 163.38(16) . . . . ? Cl2 Mo1 O2 C2 -14.4(3) . . . . ? Cl4 Mo1 O2 C2 63.34(15) . . . . ? Cl5 Mo1 O2 C2 -98.97(15) . . . . ? O3 Mo1 O2 C2 -19.39(15) . . . . ? O1 Mo1 O2 C1 27.22(19) . . . . ? Cl2 Mo1 O2 C1 -150.54(17) . . . . ? Cl4 Mo1 O2 C1 -72.82(17) . . . . ? Cl5 Mo1 O2 C1 124.87(18) . . . . ? O3 Mo1 O2 C1 -155.56(19) . . . . ? Cl3 C4 O3 C3 69.0(2) . . . . ? Cl3 C4 O3 Mo1 -158.88(11) . . . . ? C2 C3 O3 C4 178.0(2) . . . . ? C2 C3 O3 Mo1 40.5(2) . . . . ? O1 Mo1 O3 C4 -132.8(4) . . . . ? O2 Mo1 O3 C4 -145.90(19) . . . . ? Cl2 Mo1 O3 C4 35.74(18) . . . . ? Cl4 Mo1 O3 C4 126.60(18) . . . . ? Cl5 Mo1 O3 C4 -56.36(18) . . . . ? O1 Mo1 O3 C3 0.2(5) . . . . ? O2 Mo1 O3 C3 -12.83(15) . . . . ? Cl2 Mo1 O3 C3 168.80(15) . . . . ? Cl4 Mo1 O3 C3 -100.34(15) . . . . ? Cl5 Mo1 O3 C3 76.70(15) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.501 _refine_diff_density_min -1.307 _refine_diff_density_rms 0.128 _database_code_depnum_ccdc_archive 'CCDC 943836'