# Electronic Supplementary Material (ESI) for RSC Advances # 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_pnma _database_code_depnum_ccdc_archive 'CCDC 913341' #TrackingRef 'fm230112b_PNMA.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H22 Cl7 Mo N2 O3' _chemical_formula_weight 574.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 18.729(3) _cell_length_b 14.865(3) _cell_length_c 7.6628(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2133.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6262 _cell_measurement_theta_min 2.175 _cell_measurement_theta_max 28.5635 _exptl_crystal_description prism _exptl_crystal_colour pale-green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1148 _exptl_absorpt_coefficient_mu 1.504 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7735 _exptl_absorpt_correction_T_max 0.8520 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14718 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2410 _reflns_number_gt 2208 _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 'ORTEPIII (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^)+(0.0240P)^2^+1.0628P] 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 2410 _refine_ls_number_parameters 124 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0550 _refine_ls_wR_factor_gt 0.0534 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.064 _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 0.31794(10) -0.02113(12) 0.1580(2) 0.0209(4) Uani 1 1 d . . . C2 C 0.38392(10) -0.07216(14) 0.2015(3) 0.0253(4) Uani 1 1 d . . . H2A H 0.3958 -0.1131 0.1038 0.030 Uiso 1 1 calc R . . H2B H 0.3752 -0.1094 0.3065 0.030 Uiso 1 1 calc R . . C3 C 0.44710(11) -0.00948(14) 0.2354(3) 0.0307(5) Uani 1 1 d . . . H3A H 0.4862 -0.0435 0.2920 0.037 Uiso 1 1 calc R . . H3B H 0.4651 0.0146 0.1233 0.037 Uiso 1 1 calc R . . C4 C 0.42414(10) 0.06772(13) 0.3525(3) 0.0243(4) Uani 1 1 d . . . H4A H 0.4058 0.0436 0.4642 0.029 Uiso 1 1 calc R . . H4B H 0.4658 0.1066 0.3783 0.029 Uiso 1 1 calc R . . C5 C 0.36662(10) 0.12263(13) 0.2639(3) 0.0243(4) Uani 1 1 d . . . H5A H 0.3442 0.1633 0.3503 0.029 Uiso 1 1 calc R . . H5B H 0.3884 0.1601 0.1713 0.029 Uiso 1 1 calc R . . C8 C 0.42431(15) 0.2500 0.7168(4) 0.0286(6) Uani 1 2 d S . . H8A H 0.4729 0.2500 0.7677 0.034 Uiso 1 2 calc SR . . H8B H 0.4292 0.2500 0.5882 0.034 Uiso 1 2 calc SR . . Cl1 Cl 0.21241(3) 0.2500 0.46452(8) 0.01937(13) Uani 1 2 d S . . Cl2 Cl 0.03015(3) 0.2500 0.40822(9) 0.02223(14) Uani 1 2 d S . . Cl3 Cl 0.22687(3) 0.2500 0.02291(8) 0.02246(14) Uani 1 2 d S . . Cl4 Cl 0.13053(2) 0.09158(3) 0.22038(6) 0.02181(11) Uani 1 1 d . . . Cl5 Cl 0.37914(3) 0.15165(4) 0.78250(7) 0.03328(13) Uani 1 1 d . . . Mo1 Mo 0.118772(10) 0.2500 0.18670(3) 0.01554(7) Uani 1 2 d S . . N2 N 0.31163(9) 0.06412(11) 0.1867(2) 0.0244(4) Uani 1 1 d D . . H2 H 0.2713(9) 0.0894(14) 0.157(3) 0.029 Uiso 1 1 d D . . O1 O 0.06389(10) 0.2500 0.0169(3) 0.0268(4) Uani 1 2 d S . . O2 O 0.26249(7) -0.06128(10) 0.0905(2) 0.0314(3) Uani 1 1 d D . . H3 H 0.2733(13) -0.1135(12) 0.072(4) 0.047 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 C1 0.0193(9) 0.0237(9) 0.0198(9) -0.0029(7) 0.0028(7) -0.0003(7) C2 0.0302(11) 0.0221(10) 0.0235(10) -0.0063(8) -0.0043(8) 0.0061(8) C3 0.0217(10) 0.0349(11) 0.0354(12) -0.0101(9) -0.0063(9) 0.0077(8) C4 0.0242(10) 0.0266(10) 0.0221(9) -0.0027(8) -0.0009(8) -0.0009(8) C5 0.0219(9) 0.0206(10) 0.0303(11) -0.0029(8) 0.0009(8) -0.0030(7) C8 0.0205(14) 0.0404(17) 0.0249(15) 0.000 0.0038(11) 0.000 Cl1 0.0211(3) 0.0170(3) 0.0200(3) 0.000 -0.0025(2) 0.000 Cl2 0.0170(3) 0.0238(3) 0.0258(3) 0.000 0.0058(3) 0.000 Cl3 0.0187(3) 0.0280(3) 0.0207(3) 0.000 0.0047(2) 0.000 Cl4 0.0202(2) 0.0161(2) 0.0291(2) -0.00434(17) 0.00009(18) -0.00117(15) Cl5 0.0348(3) 0.0290(3) 0.0360(3) -0.0049(2) 0.0057(2) 0.0006(2) Mo1 0.01289(12) 0.01696(12) 0.01677(12) 0.000 -0.00034(8) 0.000 N2 0.0174(8) 0.0207(8) 0.0351(9) -0.0051(7) -0.0027(7) 0.0026(6) O1 0.0229(10) 0.0339(11) 0.0234(10) 0.000 -0.0050(8) 0.000 O2 0.0205(7) 0.0250(7) 0.0487(9) -0.0146(7) -0.0015(6) 0.0005(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.291(2) . ? C1 O2 1.305(2) . ? C1 C2 1.488(3) . ? C2 C3 1.528(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.519(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.512(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N2 1.472(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C8 Cl5 1.7624(16) 7_565 ? C8 Cl5 1.7624(16) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? Cl1 Mo1 2.7582(7) . ? Cl2 Mo1 2.3741(7) . ? Cl3 Mo1 2.3820(7) . ? Cl4 Mo1 2.3792(6) . ? Mo1 O1 1.6584(19) . ? Mo1 Cl4 2.3792(6) 7_565 ? N2 H2 0.874(15) . ? O2 H3 0.814(16) . ? 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 N2 C1 O2 116.33(17) . . ? N2 C1 C2 122.56(17) . . ? O2 C1 C2 121.11(17) . . ? C1 C2 C3 111.73(17) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 109.99(16) . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3B 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C3 110.16(16) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? N2 C5 C4 111.09(16) . . ? N2 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? N2 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? Cl5 C8 Cl5 112.09(15) 7_565 . ? Cl5 C8 H8A 109.2 7_565 . ? Cl5 C8 H8A 109.2 . . ? Cl5 C8 H8B 109.2 7_565 . ? Cl5 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? O1 Mo1 Cl2 97.34(7) . . ? O1 Mo1 Cl4 98.192(12) . 7_565 ? Cl2 Mo1 Cl4 89.263(12) . 7_565 ? O1 Mo1 Cl4 98.192(12) . . ? Cl2 Mo1 Cl4 89.263(12) . . ? Cl4 Mo1 Cl4 163.60(2) 7_565 . ? O1 Mo1 Cl3 96.50(7) . . ? Cl2 Mo1 Cl3 166.15(2) . . ? Cl4 Mo1 Cl3 88.768(12) 7_565 . ? Cl4 Mo1 Cl3 88.768(12) . . ? O1 Mo1 Cl1 178.82(7) . . ? Cl2 Mo1 Cl1 83.84(3) . . ? Cl4 Mo1 Cl1 81.803(12) 7_565 . ? Cl4 Mo1 Cl1 81.803(12) . . ? Cl3 Mo1 Cl1 82.32(2) . . ? C1 N2 C5 125.74(17) . . ? C1 N2 H2 117.1(15) . . ? C5 N2 H2 117.1(15) . . ? C1 O2 H3 107.9(18) . . ? 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 N2 C1 C2 C3 -15.2(3) . . . . ? O2 C1 C2 C3 165.87(18) . . . . ? C1 C2 C3 C4 45.2(2) . . . . ? C2 C3 C4 C5 -61.8(2) . . . . ? C3 C4 C5 N2 45.9(2) . . . . ? O2 C1 N2 C5 179.08(18) . . . . ? C2 C1 N2 C5 0.1(3) . . . . ? C4 C5 N2 C1 -15.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 Cl4 0.874(15) 2.682(18) 3.4260(18) 143.7(19) . N2 H2 Cl3 0.874(15) 2.728(19) 3.4249(17) 137.7(18) . O2 H3 Cl1 0.814(16) 2.207(17) 3.0037(14) 166(3) 2_554 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.483 _refine_diff_density_min -0.616 _refine_diff_density_rms 0.067 ####################################################################### # # 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_p2n _database_code_depnum_ccdc_archive 'CCDC 913342' #TrackingRef 'fm271210b_P2N.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H29 Cl5 Mo N3 O4' _chemical_formula_weight 588.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 9.2987(8) _cell_length_b 11.7668(10) _cell_length_c 22.2829(18) _cell_angle_alpha 90.00 _cell_angle_beta 101.2620(10) _cell_angle_gamma 90.00 _cell_volume 2391.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8875 _cell_measurement_theta_min 2.2455 _cell_measurement_theta_max 28.4065 _exptl_crystal_description plate _exptl_crystal_colour bright-green _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1196 _exptl_absorpt_coefficient_mu 1.132 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8136 _exptl_absorpt_correction_T_max 0.8668 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20830 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5226 _reflns_number_gt 4649 _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 'ORTEPIII (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^)+(0.0249P)^2^+1.1685P] 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 5226 _refine_ls_number_parameters 282 _refine_ls_number_restraints 119 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0555 _refine_ls_wR_factor_gt 0.0531 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.012 _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 Mo1 Mo 0.839865(17) 0.204014(13) 0.582428(7) 0.01366(5) Uani 1 1 d . . . Cl1 Cl 0.84040(5) 0.13216(4) 0.68311(2) 0.02053(10) Uani 1 1 d . . . Cl2 Cl 1.05168(5) 0.31771(4) 0.62126(2) 0.01880(10) Uani 1 1 d . . . Cl3 Cl 0.81052(5) 0.30661(4) 0.48747(2) 0.01972(10) Uani 1 1 d . . . Cl4 Cl 0.59958(5) 0.12790(4) 0.55082(2) 0.02400(11) Uani 1 1 d . . . O1 O 0.92994(14) 0.09460(11) 0.56029(6) 0.0213(3) Uani 1 1 d . . . O12 O 0.72646(14) 0.35275(11) 0.60965(6) 0.0200(3) Uani 1 1 d . . . C11 C 0.6236(2) 0.38486(15) 0.63544(8) 0.0165(4) Uani 1 1 d U . . C12 C 0.5452(2) 0.49326(17) 0.61407(9) 0.0248(4) Uani 1 1 d U . . H12A H 0.5233 0.4939 0.5688 0.030 Uiso 1 1 calc R . . H12B H 0.6115 0.5579 0.6279 0.030 Uiso 1 1 calc R . . C13 C 0.4023(2) 0.51094(19) 0.63701(10) 0.0276(5) Uani 1 1 d U . . H13A H 0.3703 0.5911 0.6309 0.033 Uiso 1 1 calc R . . H13B H 0.3244 0.4618 0.6138 0.033 Uiso 1 1 calc R . . C14 C 0.4279(2) 0.48143(17) 0.70429(9) 0.0248(4) Uani 1 1 d U . . H14A H 0.5078 0.5292 0.7271 0.030 Uiso 1 1 calc R . . H14B H 0.3379 0.4971 0.7204 0.030 Uiso 1 1 calc R . . C15 C 0.4680(2) 0.35832(19) 0.71343(10) 0.0305(5) Uani 1 1 d U . . H15A H 0.5017 0.3429 0.7576 0.037 Uiso 1 1 calc R . . H15B H 0.3805 0.3108 0.6985 0.037 Uiso 1 1 calc R . . N1 N 0.58556(19) 0.32796(15) 0.68011(8) 0.0246(4) Uani 1 1 d D . . H1 H 0.633(2) 0.2673(16) 0.6902(10) 0.030 Uiso 1 1 d D . . O22 O 0.55188(18) 0.78926(14) 0.64206(7) 0.0350(4) Uani 1 1 d D . . H22 H 0.606(3) 0.776(2) 0.6759(9) 0.053 Uiso 1 1 d D . . C21 C 0.4700(2) 0.87889(17) 0.64351(9) 0.0211(4) Uani 1 1 d U B . C22 C 0.4920(2) 0.95428(16) 0.69779(8) 0.0203(4) Uani 1 1 d U . . H22A H 0.5967 0.9763 0.7084 0.024 Uiso 1 1 calc R A 1 H22B H 0.4682 0.9116 0.7329 0.024 Uiso 1 1 calc R A 1 C23 C 0.3996(3) 1.0604(3) 0.68802(16) 0.0244(7) Uani 0.751(4) 1 d PU B 1 H23A H 0.4484 1.1180 0.6665 0.029 Uiso 0.751(4) 1 calc PR B 1 H23B H 0.3897 1.0922 0.7281 0.029 Uiso 0.751(4) 1 calc PR B 1 C24 C 0.2484(3) 1.0343(2) 0.65046(12) 0.0239(7) Uani 0.751(4) 1 d PU B 1 H24A H 0.1873 1.1038 0.6459 0.029 Uiso 0.751(4) 1 calc PR B 1 H24B H 0.1996 0.9760 0.6715 0.029 Uiso 0.751(4) 1 calc PR B 1 C23' C 0.3506(12) 1.0345(9) 0.6931(5) 0.0244(7) Uani 0.25 1 d PU B 2 H23C H 0.2665 0.9892 0.7010 0.029 Uiso 0.249(4) 1 calc PR B 2 H23D H 0.3709 1.0950 0.7245 0.029 Uiso 0.249(4) 1 calc PR B 2 C24' C 0.3135(9) 1.0864(7) 0.6316(4) 0.0213(17) Uani 0.249(4) 1 d PU B 2 H24C H 0.4003 1.1250 0.6214 0.026 Uiso 0.249(4) 1 calc PR B 2 H24D H 0.2340 1.1429 0.6299 0.026 Uiso 0.249(4) 1 calc PR B 2 C25 C 0.2644(2) 0.99067(18) 0.58722(9) 0.0260(4) Uani 1 1 d U . . H25A H 0.1684 0.9635 0.5644 0.031 Uiso 1 1 calc R B 1 H25B H 0.2984 1.0529 0.5635 0.031 Uiso 1 1 calc R B 1 N2 N 0.37127(19) 0.89712(15) 0.59537(7) 0.0253(4) Uani 1 1 d D B . H2 H 0.367(3) 0.8514(17) 0.5653(9) 0.030 Uiso 1 1 d D . . O32 O -0.06916(16) 0.39343(12) 0.33598(6) 0.0239(3) Uani 1 1 d D . . H32 H -0.113(3) 0.3435(18) 0.3120(10) 0.036 Uiso 1 1 d D . . C31 C 0.0260(2) 0.35279(16) 0.38180(8) 0.0182(4) Uani 1 1 d U . . C32 C 0.0612(2) 0.22910(16) 0.38619(9) 0.0213(4) Uani 1 1 d U . . H32A H 0.1162 0.2090 0.3539 0.026 Uiso 1 1 calc R . . H32B H -0.0316 0.1854 0.3784 0.026 Uiso 1 1 calc R . . C33 C 0.1515(2) 0.19367(16) 0.44831(9) 0.0233(4) Uani 1 1 d U . . H33A H 0.0856 0.1827 0.4777 0.028 Uiso 1 1 calc R . . H33B H 0.2010 0.1205 0.4440 0.028 Uiso 1 1 calc R . . C34 C 0.2659(2) 0.28360(16) 0.47275(9) 0.0225(4) Uani 1 1 d U . . H34A H 0.3210 0.2601 0.5134 0.027 Uiso 1 1 calc R . . H34B H 0.3363 0.2905 0.4449 0.027 Uiso 1 1 calc R . . C35 C 0.1939(2) 0.39733(16) 0.47809(8) 0.0199(4) Uani 1 1 d U . . H35A H 0.1403 0.3950 0.5123 0.024 Uiso 1 1 calc R . . H35B H 0.2701 0.4570 0.4872 0.024 Uiso 1 1 calc R . . N3 N 0.09126(18) 0.42576(13) 0.42098(7) 0.0180(3) Uani 1 1 d D . . H3 H 0.071(2) 0.4944(14) 0.4143(9) 0.022 Uiso 1 1 d D . . Cl5 Cl 0.7500 0.70758(6) 0.7500 0.02748(15) Uani 1 2 d S . . Cl6 Cl 0.7500 0.23795(6) 0.2500 0.02626(15) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mo1 0.01316(9) 0.01341(8) 0.01502(8) 0.00007(6) 0.00422(6) 0.00044(6) Cl1 0.0216(2) 0.0222(2) 0.0180(2) 0.00524(17) 0.00431(18) 0.00068(18) Cl2 0.0162(2) 0.0181(2) 0.0218(2) 0.00033(17) 0.00295(18) -0.00241(17) Cl3 0.0232(2) 0.0205(2) 0.0163(2) 0.00234(17) 0.00577(18) 0.00085(18) Cl4 0.0175(2) 0.0294(3) 0.0241(2) 0.0013(2) 0.00170(19) -0.00608(19) O1 0.0214(7) 0.0180(7) 0.0254(7) -0.0021(6) 0.0068(6) 0.0010(5) O12 0.0201(7) 0.0183(7) 0.0244(7) -0.0001(5) 0.0111(6) 0.0021(5) C11 0.0161(9) 0.0162(9) 0.0173(8) -0.0040(7) 0.0039(7) -0.0019(7) C12 0.0239(11) 0.0257(10) 0.0280(10) 0.0082(8) 0.0128(9) 0.0072(8) C13 0.0230(11) 0.0287(11) 0.0346(11) 0.0104(9) 0.0141(9) 0.0085(9) C14 0.0220(11) 0.0277(11) 0.0279(10) -0.0032(9) 0.0127(9) 0.0039(8) C15 0.0323(12) 0.0350(12) 0.0302(11) 0.0106(9) 0.0211(10) 0.0112(10) N1 0.0266(10) 0.0218(9) 0.0295(9) 0.0086(7) 0.0155(8) 0.0109(7) O22 0.0359(10) 0.0380(9) 0.0267(8) -0.0092(7) -0.0048(7) 0.0211(7) C21 0.0187(10) 0.0250(10) 0.0198(9) -0.0006(8) 0.0040(8) 0.0026(8) C22 0.0171(10) 0.0229(10) 0.0194(9) -0.0038(8) -0.0002(8) -0.0012(8) C23 0.0243(19) 0.0180(16) 0.0282(13) -0.0058(12) -0.0012(13) 0.0000(12) C24 0.0215(15) 0.0219(14) 0.0271(14) -0.0014(11) 0.0015(11) 0.0050(11) C23' 0.0243(19) 0.0180(16) 0.0282(13) -0.0058(12) -0.0012(13) 0.0000(12) C24' 0.018(3) 0.018(3) 0.028(3) -0.002(3) 0.005(3) 0.006(3) C25 0.0242(11) 0.0240(10) 0.0260(10) -0.0004(8) -0.0044(8) 0.0057(9) N2 0.0283(10) 0.0272(9) 0.0185(8) -0.0064(7) -0.0002(7) 0.0075(8) O32 0.0261(8) 0.0201(7) 0.0230(7) -0.0002(6) -0.0014(6) 0.0003(6) C31 0.0172(10) 0.0196(9) 0.0198(9) 0.0034(8) 0.0084(8) 0.0005(8) C32 0.0240(11) 0.0161(9) 0.0243(10) -0.0004(8) 0.0057(8) -0.0010(8) C33 0.0264(11) 0.0170(9) 0.0274(10) 0.0046(8) 0.0077(9) 0.0020(8) C34 0.0200(10) 0.0249(10) 0.0225(9) 0.0046(8) 0.0037(8) 0.0026(8) C35 0.0196(10) 0.0213(10) 0.0187(9) 0.0000(8) 0.0033(8) -0.0006(8) N3 0.0207(9) 0.0133(7) 0.0201(8) 0.0015(6) 0.0046(7) 0.0007(7) Cl5 0.0229(4) 0.0260(4) 0.0299(4) 0.000 -0.0038(3) 0.000 Cl6 0.0264(4) 0.0204(3) 0.0290(4) 0.000 -0.0021(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mo1 O1 1.6625(13) . ? Mo1 O12 2.1892(12) . ? Mo1 Cl4 2.3824(5) . ? Mo1 Cl1 2.3965(5) . ? Mo1 Cl2 2.3984(5) . ? Mo1 Cl3 2.4049(5) . ? O12 C11 1.266(2) . ? C11 N1 1.304(2) . ? C11 C12 1.500(3) . ? C12 C13 1.528(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.512(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.500(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N1 1.480(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? N1 H1 0.846(16) . ? O22 C21 1.305(2) . ? O22 H22 0.835(17) . ? C21 N2 1.287(3) . ? C21 C22 1.482(3) . ? C22 C23 1.507(4) . ? C22 C23' 1.606(11) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.521(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.534(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C23' C24' 1.479(15) . ? C23' H23C 0.9900 . ? C23' H23D 0.9900 . ? C24' C25 1.509(8) . ? C24' H24C 0.9900 . ? C24' H24D 0.9900 . ? C25 N2 1.471(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N2 H2 0.854(15) . ? O32 C31 1.304(2) . ? O32 H32 0.843(16) . ? C31 N3 1.289(2) . ? C31 C32 1.491(3) . ? C32 C33 1.530(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.523(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.511(3) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 N3 1.472(2) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? N3 H3 0.836(15) . ? 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 O12 177.66(6) . . ? O1 Mo1 Cl4 96.83(5) . . ? O12 Mo1 Cl4 84.70(4) . . ? O1 Mo1 Cl1 95.48(5) . . ? O12 Mo1 Cl1 86.31(4) . . ? Cl4 Mo1 Cl1 88.538(17) . . ? O1 Mo1 Cl2 96.50(5) . . ? O12 Mo1 Cl2 81.96(4) . . ? Cl4 Mo1 Cl2 166.666(17) . . ? Cl1 Mo1 Cl2 90.436(17) . . ? O1 Mo1 Cl3 96.02(5) . . ? O12 Mo1 Cl3 82.21(4) . . ? Cl4 Mo1 Cl3 89.421(17) . . ? Cl1 Mo1 Cl3 168.480(17) . . ? Cl2 Mo1 Cl3 88.940(17) . . ? C11 O12 Mo1 144.28(12) . . ? O12 C11 N1 122.32(17) . . ? O12 C11 C12 118.24(16) . . ? N1 C11 C12 119.44(16) . . ? C11 C12 C13 114.20(16) . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C14 C13 C12 108.78(17) . . ? C14 C13 H13A 109.9 . . ? C12 C13 H13A 109.9 . . ? C14 C13 H13B 109.9 . . ? C12 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C15 C14 C13 110.07(17) . . ? C15 C14 H14A 109.6 . . ? C13 C14 H14A 109.6 . . ? C15 C14 H14B 109.6 . . ? C13 C14 H14B 109.6 . . ? H14A C14 H14B 108.2 . . ? N1 C15 C14 110.72(16) . . ? N1 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C11 N1 C15 126.56(17) . . ? C11 N1 H1 115.6(15) . . ? C15 N1 H1 117.8(15) . . ? C21 O22 H22 112(2) . . ? N2 C21 O22 116.04(17) . . ? N2 C21 C22 122.89(18) . . ? O22 C21 C22 121.07(17) . . ? C21 C22 C23 113.20(19) . . ? C21 C22 C23' 108.6(4) . . ? C23 C22 C23' 21.1(3) . . ? C21 C22 H22A 108.9 . . ? C23 C22 H22A 108.9 . . ? C23' C22 H22A 128.0 . . ? C21 C22 H22B 108.9 . . ? C23 C22 H22B 108.9 . . ? C23' C22 H22B 92.4 . . ? H22A C22 H22B 107.8 . . ? C22 C23 C24 110.6(2) . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C23 C24 C25 109.2(2) . . ? C23 C24 H24A 109.8 . . ? C25 C24 H24A 109.8 . . ? C23 C24 H24B 109.8 . . ? C25 C24 H24B 109.8 . . ? H24A C24 H24B 108.3 . . ? C24' C23' C22 110.0(7) . . ? C24' C23' H23C 109.7 . . ? C22 C23' H23C 109.7 . . ? C24' C23' H23D 109.7 . . ? C22 C23' H23D 109.7 . . ? H23C C23' H23D 108.2 . . ? C23' C24' C25 106.6(7) . . ? C23' C24' H24C 110.4 . . ? C25 C24' H24C 110.4 . . ? C23' C24' H24D 110.4 . . ? C25 C24' H24D 110.4 . . ? H24C C24' H24D 108.6 . . ? N2 C25 C24' 111.5(3) . . ? N2 C25 C24 108.74(17) . . ? C24' C25 C24 38.7(3) . . ? N2 C25 H25A 109.9 . . ? C24' C25 H25A 134.8 . . ? C24 C25 H25A 109.9 . . ? N2 C25 H25B 109.9 . . ? C24' C25 H25B 73.2 . . ? C24 C25 H25B 109.9 . . ? H25A C25 H25B 108.3 . . ? C21 N2 C25 125.67(17) . . ? C21 N2 H2 117.7(16) . . ? C25 N2 H2 116.6(16) . . ? C31 O32 H32 114.1(17) . . ? N3 C31 O32 116.34(17) . . ? N3 C31 C32 122.53(18) . . ? O32 C31 C32 121.06(17) . . ? C31 C32 C33 113.58(16) . . ? C31 C32 H32A 108.9 . . ? C33 C32 H32A 108.9 . . ? C31 C32 H32B 108.9 . . ? C33 C32 H32B 108.9 . . ? H32A C32 H32B 107.7 . . ? C34 C33 C32 110.84(16) . . ? C34 C33 H33A 109.5 . . ? C32 C33 H33A 109.5 . . ? C34 C33 H33B 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 108.1 . . ? C35 C34 C33 110.75(16) . . ? C35 C34 H34A 109.5 . . ? C33 C34 H34A 109.5 . . ? C35 C34 H34B 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 108.1 . . ? N3 C35 C34 110.82(15) . . ? N3 C35 H35A 109.5 . . ? C34 C35 H35A 109.5 . . ? N3 C35 H35B 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 108.1 . . ? C31 N3 C35 125.04(16) . . ? C31 N3 H3 117.5(15) . . ? C35 N3 H3 117.4(15) . . ? 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 O12 C11 173.8(14) . . . . ? Cl4 Mo1 O12 C11 42.8(2) . . . . ? Cl1 Mo1 O12 C11 -46.1(2) . . . . ? Cl2 Mo1 O12 C11 -137.1(2) . . . . ? Cl3 Mo1 O12 C11 132.9(2) . . . . ? Mo1 O12 C11 N1 32.5(3) . . . . ? Mo1 O12 C11 C12 -148.45(17) . . . . ? O12 C11 C12 C13 166.67(18) . . . . ? N1 C11 C12 C13 -14.3(3) . . . . ? C11 C12 C13 C14 44.6(2) . . . . ? C12 C13 C14 C15 -62.8(2) . . . . ? C13 C14 C15 N1 49.1(2) . . . . ? O12 C11 N1 C15 179.6(2) . . . . ? C12 C11 N1 C15 0.6(3) . . . . ? C14 C15 N1 C11 -18.5(3) . . . . ? N2 C21 C22 C23 -6.6(3) . . . . ? O22 C21 C22 C23 173.1(2) . . . . ? N2 C21 C22 C23' 15.4(5) . . . . ? O22 C21 C22 C23' -164.8(4) . . . . ? C21 C22 C23 C24 38.4(3) . . . . ? C23' C22 C23 C24 -43.1(13) . . . . ? C22 C23 C24 C25 -62.0(3) . . . . ? C21 C22 C23' C24' -48.6(8) . . . . ? C23 C22 C23' C24' 57.9(12) . . . . ? C22 C23' C24' C25 66.8(8) . . . . ? C23' C24' C25 N2 -51.3(7) . . . . ? C23' C24' C25 C24 42.2(6) . . . . ? C23 C24 C25 N2 51.9(3) . . . . ? C23 C24 C25 C24' -49.4(5) . . . . ? O22 C21 N2 C25 178.32(19) . . . . ? C22 C21 N2 C25 -1.9(3) . . . . ? C24' C25 N2 C21 19.8(4) . . . . ? C24 C25 N2 C21 -21.5(3) . . . . ? N3 C31 C32 C33 14.2(2) . . . . ? O32 C31 C32 C33 -168.87(16) . . . . ? C31 C32 C33 C34 -38.8(2) . . . . ? C32 C33 C34 C35 57.5(2) . . . . ? C33 C34 C35 N3 -49.6(2) . . . . ? O32 C31 N3 C35 175.29(16) . . . . ? C32 C31 N3 C35 -7.7(3) . . . . ? C34 C35 N3 C31 25.6(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 N1 H1 Cl1 0.846(16) 2.529(18) 3.2964(17) 151(2) . O22 H22 Cl5 0.835(17) 2.076(18) 2.8935(15) 166(3) . N2 H2 Cl4 0.854(15) 2.68(2) 3.3342(17) 134.8(19) 3_666 N2 H2 Cl3 0.854(15) 2.609(19) 3.2853(18) 137.0(19) 3_666 O32 H32 Cl6 0.843(16) 2.095(17) 2.9303(15) 171(2) 1_455 N3 H3 Cl2 0.836(15) 2.541(16) 3.3579(17) 166(2) 3_666 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.492 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.065