# 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_1 # ======================================================================= _audit_creation_method 'SHELXL-97, manual editing plus enCIFer' _audit_creation_date '01 October 2013' # ======================================================================= _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H18 N3, Cl' _chemical_formula_sum 'C13 H18 Cl N3' _chemical_formula_weight 251.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 11.7600(7) _cell_length_b 11.1632(6) _cell_length_c 10.6280(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.648(3) _cell_angle_gamma 90.00 _cell_volume 1379.37(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8906 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 27.84 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9670 _exptl_absorpt_correction_T_max 0.9744 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1997) ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Kappa CCD APEX II' _diffrn_measurement_method '\w / \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 33917 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 29.13 _reflns_number_total 3697 _reflns_number_gt 2768 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'APEX2 (Bruker, 2006)' _computing_data_reduction 'SAINT+ (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' #============================================================================== # REFINEMENT DATA #============================================================================== _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^)+(0.0560P)^2^+0.6778P] 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 3697 _refine_ls_number_parameters 176 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1139 _refine_ls_wR_factor_gt 0.1009 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 #============================================================================== # ATOMIC COORDINATES #============================================================================== 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 Cl1 Cl 0.18485(3) 0.93340(3) 0.01268(4) 0.02536(12) Uani 1 1 d . . . N1 N 0.15129(11) 0.35436(13) 0.33501(13) 0.0273(3) Uani 1 1 d D . . H1 H 0.1761(16) 0.4191(13) 0.3883(16) 0.041 Uiso 1 1 d D . . N2 N 0.41777(11) 0.26135(13) 0.23174(14) 0.0305(3) Uani 1 1 d . A . N3 N 0.51986(11) 0.31541(14) 0.26362(14) 0.0337(3) Uani 1 1 d . . . C1 C 0.03753(13) 0.33068(17) 0.32168(17) 0.0326(4) Uani 1 1 d . . . H1A H -0.0105 0.3767 0.3674 0.039 Uiso 1 1 calc R . . C2 C -0.00895(14) 0.24089(17) 0.24286(18) 0.0360(4) Uani 1 1 d . . . H2 H -0.0891 0.2247 0.2322 0.043 Uiso 1 1 calc R . . C3 C 0.06378(14) 0.17374(17) 0.17846(17) 0.0350(4) Uani 1 1 d . . . H3 H 0.0334 0.1104 0.1238 0.042 Uiso 1 1 calc R . . C4 C 0.17995(14) 0.19887(16) 0.19383(16) 0.0310(4) Uani 1 1 d . . . H4 H 0.2294 0.1526 0.1501 0.037 Uiso 1 1 calc R . . C5 C 0.22469(13) 0.29199(14) 0.27342(14) 0.0257(3) Uani 1 1 d . A . C6 C 0.34547(12) 0.32617(15) 0.29131(15) 0.0260(3) Uani 1 1 d . . . C7 C 0.40199(13) 0.42212(16) 0.35982(16) 0.0314(4) Uani 1 1 d . A . H7 H 0.3700 0.4807 0.4090 0.038 Uiso 1 1 calc R . . C8 C 0.51414(14) 0.41175(18) 0.33929(17) 0.0368(4) Uani 1 1 d . A . H8 H 0.5761 0.4628 0.3722 0.044 Uiso 1 1 calc R . . C9 C 0.62050(15) 0.27037(19) 0.2119(2) 0.0449(5) Uani 0.704(7) 1 d P A -1 H9A H 0.6149 0.1821 0.2038 0.054 Uiso 0.704(7) 1 calc PR A -1 H9B H 0.6908 0.2892 0.2723 0.054 Uiso 0.704(7) 1 calc PR A -1 C10 C 0.6312(2) 0.3226(2) 0.0859(3) 0.0624(7) Uani 0.704(7) 1 d P A -1 H10A H 0.5558 0.3215 0.0300 0.075 Uiso 0.704(7) 1 calc PR A -1 H10B H 0.6870 0.2762 0.0445 0.075 Uiso 0.704(7) 1 calc PR A -1 C11 C 0.6740(3) 0.4549(3) 0.1104(3) 0.0449(10) Uani 0.704(7) 1 d P A -1 H11A H 0.6113 0.5038 0.1364 0.054 Uiso 0.704(7) 1 calc PR A -1 H11B H 0.7395 0.4560 0.1809 0.054 Uiso 0.704(7) 1 calc PR A -1 C12 C 0.7117(4) 0.5097(4) -0.0087(4) 0.0597(12) Uani 0.704(7) 1 d P A -1 H12A H 0.7210 0.5973 0.0030 0.072 Uiso 0.704(7) 1 calc PR A -1 H12B H 0.6513 0.4957 -0.0827 0.072 Uiso 0.704(7) 1 calc PR A -1 C13 C 0.8256(2) 0.4554(3) -0.0358(3) 0.0777(9) Uani 0.704(7) 1 d P A -1 H13A H 0.8469 0.4916 -0.1129 0.117 Uiso 0.704(7) 1 calc PR A -1 H13B H 0.8165 0.3687 -0.0480 0.117 Uiso 0.704(7) 1 calc PR A -1 H13C H 0.8861 0.4712 0.0363 0.117 Uiso 0.704(7) 1 calc PR A -1 C9' C 0.62050(15) 0.27037(19) 0.2119(2) 0.0449(5) Uani 0.296(7) 1 d P A -2 H9C H 0.6149 0.1821 0.2038 0.054 Uiso 0.296(7) 1 calc PR A -2 H9D H 0.6908 0.2892 0.2723 0.054 Uiso 0.296(7) 1 calc PR A -2 C10' C 0.6312(2) 0.3226(2) 0.0859(3) 0.0624(7) Uani 0.296(7) 1 d P A -2 H10C H 0.5773 0.2734 0.0266 0.075 Uiso 0.296(7) 1 calc PR A -2 H10D H 0.7088 0.2967 0.0722 0.075 Uiso 0.296(7) 1 calc PR A -2 C11' C 0.6196(7) 0.4500(7) 0.0226(7) 0.052(3) Uani 0.296(7) 1 d P A -2 H11C H 0.5918 0.4449 -0.0699 0.063 Uiso 0.296(7) 1 calc PR A -2 H11D H 0.5675 0.5023 0.0630 0.063 Uiso 0.296(7) 1 calc PR A -2 C12' C 0.7423(12) 0.4933(9) 0.0490(13) 0.070(3) Uani 0.296(7) 1 d P A -2 H12C H 0.7404 0.5820 0.0487 0.084 Uiso 0.296(7) 1 calc PR A -2 H12D H 0.7740 0.4682 0.1366 0.084 Uiso 0.296(7) 1 calc PR A -2 C13' C 0.8256(2) 0.4554(3) -0.0358(3) 0.0777(9) Uani 0.296(7) 1 d P A -2 H13D H 0.9002 0.4935 -0.0077 0.117 Uiso 0.296(7) 1 calc PR A -2 H13E H 0.7970 0.4796 -0.1234 0.117 Uiso 0.296(7) 1 calc PR A -2 H13F H 0.8345 0.3681 -0.0319 0.117 Uiso 0.296(7) 1 calc PR A -2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01864(17) 0.0236(2) 0.0336(2) 0.00361(16) 0.00333(13) -0.00101(14) N1 0.0225(6) 0.0278(7) 0.0317(7) -0.0069(6) 0.0048(5) -0.0006(5) N2 0.0208(6) 0.0303(8) 0.0400(8) -0.0066(6) 0.0038(5) 0.0006(5) N3 0.0184(6) 0.0394(9) 0.0430(8) -0.0116(7) 0.0037(6) 0.0012(6) C1 0.0223(7) 0.0369(10) 0.0395(9) -0.0066(7) 0.0078(6) -0.0001(7) C2 0.0213(7) 0.0408(10) 0.0455(10) -0.0060(8) 0.0039(7) -0.0058(7) C3 0.0293(8) 0.0336(10) 0.0410(9) -0.0101(8) 0.0011(7) -0.0060(7) C4 0.0262(7) 0.0300(9) 0.0366(8) -0.0091(7) 0.0040(6) -0.0006(7) C5 0.0223(7) 0.0260(8) 0.0283(7) -0.0019(6) 0.0025(6) 0.0014(6) C6 0.0202(7) 0.0295(9) 0.0279(7) -0.0048(6) 0.0021(6) 0.0010(6) C7 0.0229(7) 0.0387(10) 0.0327(8) -0.0133(7) 0.0041(6) -0.0022(7) C8 0.0223(7) 0.0462(11) 0.0414(9) -0.0176(8) 0.0034(7) -0.0046(7) C9 0.0210(8) 0.0474(12) 0.0672(13) -0.0206(10) 0.0100(8) 0.0030(7) C10 0.0657(14) 0.0457(13) 0.0886(17) -0.0067(12) 0.0528(14) 0.0097(11) C11 0.063(2) 0.0399(17) 0.0357(17) 0.0005(12) 0.0185(15) 0.0036(14) C12 0.078(3) 0.057(3) 0.049(2) 0.017(2) 0.027(2) 0.016(2) C13 0.0678(17) 0.097(2) 0.0748(18) 0.0300(16) 0.0319(14) 0.0060(15) C9' 0.0210(8) 0.0474(12) 0.0672(13) -0.0206(10) 0.0100(8) 0.0030(7) C10' 0.0657(14) 0.0457(13) 0.0886(17) -0.0067(12) 0.0528(14) 0.0097(11) C11' 0.060(5) 0.066(5) 0.035(4) 0.003(3) 0.019(3) 0.030(4) C12' 0.104(9) 0.031(5) 0.067(7) 0.004(5) -0.008(7) -0.008(5) C13' 0.0678(17) 0.097(2) 0.0748(18) 0.0300(16) 0.0319(14) 0.0060(15) _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. ; #============================================================================== # GEOMETRY #============================================================================== 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 N1 C1 1.3501(19) . ? N1 C5 1.352(2) . ? N1 H1 0.937(9) . ? N2 N3 1.3409(18) . ? N2 C6 1.345(2) . ? N3 C8 1.351(2) . ? N3 C9 1.467(2) . ? C1 C2 1.367(2) . ? C1 H1A 0.9500 . ? C2 C3 1.392(3) . ? C2 H2 0.9500 . ? C3 C4 1.380(2) . ? C3 H3 0.9500 . ? C4 C5 1.393(2) . ? C4 H4 0.9500 . ? C5 C6 1.455(2) . ? C6 C7 1.405(2) . ? C7 C8 1.374(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.483(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.569(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.530(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.536(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C11' C12' 1.508(15) . ? C11' H11C 0.9900 . ? C11' H11D 0.9900 . ? C12' H12C 0.9900 . ? C12' H12D 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 122.89(14) . . ? C1 N1 H1 115.3(12) . . ? C5 N1 H1 121.8(12) . . ? N3 N2 C6 104.14(13) . . ? N2 N3 C8 112.70(13) . . ? N2 N3 C9 119.55(14) . . ? C8 N3 C9 127.69(14) . . ? N1 C1 C2 120.44(15) . . ? N1 C1 H1A 119.8 . . ? C2 C1 H1A 119.8 . . ? C1 C2 C3 118.53(15) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 120.18(16) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.03(15) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? N1 C5 C4 117.91(14) . . ? N1 C5 C6 118.90(14) . . ? C4 C5 C6 123.18(14) . . ? N2 C6 C7 111.77(13) . . ? N2 C6 C5 118.11(14) . . ? C7 C6 C5 130.09(14) . . ? C8 C7 C6 104.13(14) . . ? C8 C7 H7 127.9 . . ? C6 C7 H7 127.9 . . ? N3 C8 C7 107.26(14) . . ? N3 C8 H8 126.4 . . ? C7 C8 H8 126.4 . . ? N3 C9 C10 112.71(17) . . ? N3 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? N3 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 C11 106.8(2) . . ? C9 C10 H10A 110.4 . . ? C11 C10 H10A 110.4 . . ? C9 C10 H10B 110.4 . . ? C11 C10 H10B 110.4 . . ? H10A C10 H10B 108.6 . . ? C12 C11 C10 111.4(3) . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C13 111.5(3) . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12' C11' H11C 111.6 . . ? C12' C11' H11D 111.6 . . ? H11C C11' H11D 109.4 . . ? C11' C12' H12C 107.4 . . ? C11' C12' H12D 107.4 . . ? H12C C12' H12D 106.9 . . ? 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 C6 N2 N3 C8 -0.7(2) . . . . ? C6 N2 N3 C9 -178.21(16) . . . . ? C5 N1 C1 C2 -0.4(3) . . . . ? N1 C1 C2 C3 0.9(3) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C1 N1 C5 C4 -0.5(2) . . . . ? C1 N1 C5 C6 178.42(15) . . . . ? C3 C4 C5 N1 0.8(3) . . . . ? C3 C4 C5 C6 -178.04(16) . . . . ? N3 N2 C6 C7 0.64(19) . . . . ? N3 N2 C6 C5 178.55(14) . . . . ? N1 C5 C6 N2 178.43(15) . . . . ? C4 C5 C6 N2 -2.7(2) . . . . ? N1 C5 C6 C7 -4.1(3) . . . . ? C4 C5 C6 C7 174.77(17) . . . . ? N2 C6 C7 C8 -0.4(2) . . . . ? C5 C6 C7 C8 -177.99(17) . . . . ? N2 N3 C8 C7 0.4(2) . . . . ? C9 N3 C8 C7 177.74(18) . . . . ? C6 C7 C8 N3 0.0(2) . . . . ? N2 N3 C9 C10 86.6(2) . . . . ? C8 N3 C9 C10 -90.5(2) . . . . ? N3 C9 C10 C11 74.3(2) . . . . ? C9 C10 C11 C12 168.3(3) . . . . ? C10 C11 C12 C13 -71.9(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 N1 H1 Cl1 0.937(9) 2.104(11) 3.0184(14) 164.7(17) 4_576 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.539 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.050 #============================================================================== # END #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 964290' ####################################################################### # # 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_2 # ======================================================================= _audit_creation_method 'SHELXL-97, manual editing plus enCIFer' _audit_creation_date '01 October 2013' # ======================================================================= _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H17 Cl2 Mo N3 O2' _chemical_formula_sum 'C13 H17 Cl2 Mo N3 O2' _chemical_formula_weight 414.14 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' #============================================================================== # CRYSTAL DATA #============================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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' '-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 8.4532(5) _cell_length_b 11.4651(8) _cell_length_c 32.826(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3181.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2356 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 26.62 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.729 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 1.167 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9023 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1997) ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Kappa CCD APEX II' _diffrn_measurement_method '\w / \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 18097 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.0773 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 29.13 _reflns_number_total 4252 _reflns_number_gt 2734 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'APEX2 (Bruker, 2006)' _computing_data_reduction 'SAINT+ (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' #============================================================================= # REFINEMENT DATA #============================================================================= _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^)+(0.0361P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4252 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0898 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.0927 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 #============================================================================= # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS #============================================================================= 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 1.17275(3) 0.05115(3) 0.399671(10) 0.01701(9) Uani 1 1 d . . . Cl1 Cl 1.13716(10) -0.05077(9) 0.46206(3) 0.0242(2) Uani 1 1 d . . . Cl2 Cl 1.11044(12) 0.16320(8) 0.34118(3) 0.0258(2) Uani 1 1 d . . . O1 O 1.3198(3) 0.1391(2) 0.41713(9) 0.0258(6) Uani 1 1 d . . . O2 O 1.2646(3) -0.0585(2) 0.37499(8) 0.0243(6) Uani 1 1 d . . . N1 N 0.8571(3) -0.1088(2) 0.36593(10) 0.0172(7) Uani 1 1 d . . . N2 N 0.9191(3) -0.0189(2) 0.38723(9) 0.0149(7) Uani 1 1 d . . . N3 N 0.9825(3) 0.1727(2) 0.42964(10) 0.0166(7) Uani 1 1 d . . . C1 C 0.6980(4) -0.1025(3) 0.36507(11) 0.0194(8) Uani 1 1 d . . . H1 H 0.6291 -0.1558 0.3518 0.023 Uiso 1 1 calc R . . C2 C 0.6527(4) -0.0056(3) 0.38679(12) 0.0195(8) Uani 1 1 d . . . H2 H 0.5481 0.0216 0.3915 0.023 Uiso 1 1 calc R . . C3 C 0.7940(4) 0.0443(3) 0.40049(11) 0.0158(7) Uani 1 1 d . . . C4 C 0.8269(4) 0.1461(3) 0.42533(11) 0.0174(7) Uani 1 1 d . . . C5 C 0.7094(4) 0.2140(3) 0.44358(12) 0.0186(8) Uani 1 1 d . . . H5 H 0.6008 0.1950 0.4401 0.022 Uiso 1 1 calc R . . C6 C 0.7534(5) 0.3087(3) 0.46668(12) 0.0240(8) Uani 1 1 d . . . H6 H 0.6752 0.3558 0.4794 0.029 Uiso 1 1 calc R . . C7 C 0.9113(5) 0.3348(3) 0.47132(12) 0.0222(9) Uani 1 1 d . . . H7 H 0.9433 0.3993 0.4875 0.027 Uiso 1 1 calc R . . C8 C 1.0227(5) 0.2658(3) 0.45214(12) 0.0216(9) Uani 1 1 d . . . H8 H 1.1315 0.2850 0.4550 0.026 Uiso 1 1 calc R . . C9 C 0.9579(5) -0.1946(3) 0.34519(12) 0.0218(9) Uani 1 1 d . . . H9A H 0.8975 -0.2678 0.3414 0.026 Uiso 1 1 calc R . . H9B H 1.0504 -0.2122 0.3626 0.026 Uiso 1 1 calc R . . C10 C 1.0157(4) -0.1518(3) 0.30393(12) 0.0225(9) Uani 1 1 d . . . H10A H 1.0693 -0.0758 0.3077 0.027 Uiso 1 1 calc R . . H10B H 1.0950 -0.2077 0.2934 0.027 Uiso 1 1 calc R . . C11 C 0.8855(5) -0.1376(4) 0.27236(12) 0.0273(9) Uani 1 1 d . . . H11A H 0.8052 -0.0829 0.2832 0.033 Uiso 1 1 calc R . . H11B H 0.8333 -0.2140 0.2683 0.033 Uiso 1 1 calc R . . C12 C 0.9418(5) -0.0927(4) 0.23114(13) 0.0296(10) Uani 1 1 d . . . H12A H 0.8550 -0.1015 0.2111 0.035 Uiso 1 1 calc R . . H12B H 1.0315 -0.1414 0.2218 0.035 Uiso 1 1 calc R . . C13 C 0.9941(6) 0.0353(4) 0.23201(15) 0.0440(12) Uani 1 1 d . . . H13A H 0.9039 0.0847 0.2393 0.066 Uiso 1 1 calc R . . H13B H 1.0338 0.0577 0.2051 0.066 Uiso 1 1 calc R . . H13C H 1.0783 0.0452 0.2523 0.066 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 0.00932(14) 0.01859(14) 0.02312(17) -0.00219(16) 0.00080(13) -0.00022(14) Cl1 0.0213(5) 0.0268(4) 0.0245(5) 0.0023(5) -0.0006(4) 0.0060(4) Cl2 0.0263(5) 0.0244(5) 0.0265(6) 0.0047(5) 0.0034(4) -0.0010(4) O1 0.0169(14) 0.0264(14) 0.0341(17) -0.0048(13) -0.0011(12) -0.0038(12) O2 0.0189(14) 0.0242(13) 0.0297(16) -0.0043(13) 0.0028(11) 0.0020(13) N1 0.0158(17) 0.0163(14) 0.0195(17) -0.0032(14) 0.0004(12) -0.0054(12) N2 0.0119(16) 0.0146(14) 0.0181(17) -0.0003(12) 0.0024(12) -0.0006(12) N3 0.0112(16) 0.0153(14) 0.0234(18) 0.0019(14) 0.0017(13) 0.0008(12) C1 0.017(2) 0.0250(18) 0.0161(19) 0.0028(17) -0.0004(15) -0.0067(16) C2 0.011(2) 0.0268(19) 0.021(2) 0.0033(17) -0.0006(14) -0.0015(15) C3 0.0116(18) 0.0198(16) 0.0161(17) 0.0052(18) 0.0014(14) -0.0006(14) C4 0.0129(17) 0.0211(17) 0.0180(19) 0.0032(16) -0.0003(15) 0.0009(16) C5 0.011(2) 0.0246(19) 0.020(2) 0.0007(17) 0.0002(14) 0.0038(15) C6 0.029(2) 0.0230(18) 0.021(2) 0.0043(18) 0.0046(19) 0.0117(17) C7 0.028(2) 0.0151(17) 0.023(2) -0.0052(17) -0.0006(17) 0.0025(16) C8 0.024(2) 0.0201(18) 0.021(2) -0.0018(17) -0.0022(16) 0.0015(16) C9 0.023(2) 0.0164(17) 0.026(2) -0.0054(17) -0.0023(17) 0.0016(16) C10 0.022(2) 0.0262(19) 0.019(2) -0.0021(18) 0.0017(16) 0.0018(17) C11 0.018(2) 0.037(2) 0.027(2) 0.000(2) 0.0008(17) -0.0027(19) C12 0.023(2) 0.043(2) 0.023(2) -0.003(2) -0.0002(17) 0.0005(19) C13 0.054(3) 0.040(3) 0.038(3) 0.012(2) 0.006(2) -0.002(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. ; #============================================================================= # GEOMETRY #============================================================================= 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 1.685(3) . ? Mo1 O1 1.700(2) . ? Mo1 N2 2.326(3) . ? Mo1 N3 2.344(3) . ? Mo1 Cl2 2.3694(11) . ? Mo1 Cl1 2.3769(10) . ? N1 C1 1.347(4) . ? N1 N2 1.352(4) . ? N1 C9 1.468(4) . ? N2 C3 1.353(4) . ? N3 C8 1.342(4) . ? N3 C4 1.358(4) . ? C1 C2 1.375(5) . ? C1 H1 0.9500 . ? C2 C3 1.399(5) . ? C2 H2 0.9500 . ? C3 C4 1.451(5) . ? C4 C5 1.397(5) . ? C5 C6 1.375(5) . ? C5 H5 0.9500 . ? C6 C7 1.377(5) . ? C6 H6 0.9500 . ? C7 C8 1.381(5) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.521(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.520(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.524(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.533(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 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 O1 105.54(12) . . ? O2 Mo1 N2 94.75(11) . . ? O1 Mo1 N2 159.71(11) . . ? O2 Mo1 N3 164.00(11) . . ? O1 Mo1 N3 90.42(11) . . ? N2 Mo1 N3 69.29(10) . . ? O2 Mo1 Cl2 96.73(10) . . ? O1 Mo1 Cl2 96.54(10) . . ? N2 Mo1 Cl2 80.79(8) . . ? N3 Mo1 Cl2 82.26(8) . . ? O2 Mo1 Cl1 96.08(9) . . ? O1 Mo1 Cl1 95.38(10) . . ? N2 Mo1 Cl1 82.24(8) . . ? N3 Mo1 Cl1 81.01(8) . . ? Cl2 Mo1 Cl1 159.48(4) . . ? C1 N1 N2 110.9(3) . . ? C1 N1 C9 127.3(3) . . ? N2 N1 C9 121.7(3) . . ? N1 N2 C3 105.8(3) . . ? N1 N2 Mo1 135.4(2) . . ? C3 N2 Mo1 118.6(2) . . ? C8 N3 C4 118.7(3) . . ? C8 N3 Mo1 122.0(2) . . ? C4 N3 Mo1 119.2(2) . . ? N1 C1 C2 108.1(3) . . ? N1 C1 H1 126.0 . . ? C2 C1 H1 126.0 . . ? C1 C2 C3 105.1(3) . . ? C1 C2 H2 127.5 . . ? C3 C2 H2 127.5 . . ? N2 C3 C2 110.2(3) . . ? N2 C3 C4 117.5(3) . . ? C2 C3 C4 132.3(3) . . ? N3 C4 C5 121.3(3) . . ? N3 C4 C3 115.1(3) . . ? C5 C4 C3 123.6(3) . . ? C6 C5 C4 118.9(3) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 119.7(4) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C8 119.1(4) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? N3 C8 C7 122.3(4) . . ? N3 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? N1 C9 C10 112.5(3) . . ? N1 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N1 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 114.1(3) . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C12 114.6(3) . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C11 C12 C13 113.4(4) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 C1 N1 N2 C3 0.9(4) . . . . ? C9 N1 N2 C3 177.5(3) . . . . ? C1 N1 N2 Mo1 -173.2(3) . . . . ? C9 N1 N2 Mo1 3.4(5) . . . . ? O2 Mo1 N2 N1 -4.2(3) . . . . ? O1 Mo1 N2 N1 175.8(3) . . . . ? N3 Mo1 N2 N1 177.0(3) . . . . ? Cl2 Mo1 N2 N1 91.8(3) . . . . ? Cl1 Mo1 N2 N1 -99.7(3) . . . . ? O2 Mo1 N2 C3 -177.7(3) . . . . ? O1 Mo1 N2 C3 2.3(5) . . . . ? N3 Mo1 N2 C3 3.5(2) . . . . ? Cl2 Mo1 N2 C3 -81.6(2) . . . . ? Cl1 Mo1 N2 C3 86.8(2) . . . . ? O2 Mo1 N3 C8 172.8(4) . . . . ? O1 Mo1 N3 C8 -3.2(3) . . . . ? N2 Mo1 N3 C8 177.2(3) . . . . ? Cl2 Mo1 N3 C8 -99.7(3) . . . . ? Cl1 Mo1 N3 C8 92.2(3) . . . . ? O2 Mo1 N3 C4 -4.9(6) . . . . ? O1 Mo1 N3 C4 179.1(3) . . . . ? N2 Mo1 N3 C4 -0.5(2) . . . . ? Cl2 Mo1 N3 C4 82.5(3) . . . . ? Cl1 Mo1 N3 C4 -85.6(3) . . . . ? N2 N1 C1 C2 -0.4(4) . . . . ? C9 N1 C1 C2 -176.8(3) . . . . ? N1 C1 C2 C3 -0.2(4) . . . . ? N1 N2 C3 C2 -1.0(4) . . . . ? Mo1 N2 C3 C2 174.3(2) . . . . ? N1 N2 C3 C4 178.7(3) . . . . ? Mo1 N2 C3 C4 -6.1(4) . . . . ? C1 C2 C3 N2 0.7(4) . . . . ? C1 C2 C3 C4 -178.8(4) . . . . ? C8 N3 C4 C5 0.4(5) . . . . ? Mo1 N3 C4 C5 178.2(3) . . . . ? C8 N3 C4 C3 179.9(3) . . . . ? Mo1 N3 C4 C3 -2.3(4) . . . . ? N2 C3 C4 N3 5.5(5) . . . . ? C2 C3 C4 N3 -175.0(4) . . . . ? N2 C3 C4 C5 -175.0(3) . . . . ? C2 C3 C4 C5 4.5(6) . . . . ? N3 C4 C5 C6 -0.7(5) . . . . ? C3 C4 C5 C6 179.8(3) . . . . ? C4 C5 C6 C7 0.1(6) . . . . ? C5 C6 C7 C8 0.8(6) . . . . ? C4 N3 C8 C7 0.6(5) . . . . ? Mo1 N3 C8 C7 -177.1(3) . . . . ? C6 C7 C8 N3 -1.2(6) . . . . ? C1 N1 C9 C10 94.1(4) . . . . ? N2 N1 C9 C10 -81.8(4) . . . . ? N1 C9 C10 C11 -66.8(4) . . . . ? C9 C10 C11 C12 179.0(3) . . . . ? C10 C11 C12 C13 -70.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.541 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.125 #============================================================================= # END #============================================================================= _database_code_depnum_ccdc_archive 'CCDC 964291'