# Electronic Supplementary Material (ESI) for CrystEngComm # 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 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H6 Cd F2 N2 O4' _chemical_formula_weight 392.59 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 '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 10.8861(8) _cell_length_b 10.2944(8) _cell_length_c 14.3534(8) _cell_angle_alpha 90.00 _cell_angle_beta 120.868(4) _cell_angle_gamma 90.00 _cell_volume 1380.68(17) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4669 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 30.52 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.889 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 1.621 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6251 _exptl_absorpt_correction_T_max 0.7169 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 6902 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2437 _reflns_number_gt 2289 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+4.1280P] 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 2437 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 Cd1 Cd 0.67672(3) 0.61497(3) 0.59406(2) 0.02274(13) Uani 1 1 d . . . F1 F 0.8428(7) 0.3501(6) 0.3233(4) 0.1152(18) Uani 1 1 d . . . F2 F 0.2291(6) 0.5041(6) -0.0386(4) 0.123(2) Uani 1 1 d . . . O1 O 1.1561(4) 0.1245(3) 0.7066(3) 0.0411(8) Uani 1 1 d . . . O2 O 1.1319(4) 0.2589(3) 0.8152(3) 0.0416(8) Uani 1 1 d . . . O3 O 0.6025(3) 0.7035(3) 0.4283(2) 0.0361(7) Uani 1 1 d . . . O4 O 0.5726(5) 0.4364(4) 0.6219(3) 0.0506(10) Uani 1 1 d . . . N1 N 0.8093(4) 0.4635(4) 0.5600(3) 0.0306(8) Uani 1 1 d . . . N2 N 0.5246(4) 0.7507(4) 0.6194(3) 0.0292(8) Uani 1 1 d . . . C1 C 1.0991(4) 0.2212(4) 0.7229(4) 0.0300(9) Uani 1 1 d . . . C2 C 0.9894(4) 0.2985(4) 0.6271(3) 0.0279(9) Uani 1 1 d . . . C3 C 0.9066(5) 0.3895(4) 0.6410(4) 0.0290(9) Uani 1 1 d . . . H3 H 0.9191 0.3997 0.7097 0.035 Uiso 1 1 calc R . . C4 C 0.7932(5) 0.4470(5) 0.4614(4) 0.0314(9) Uani 1 1 d . . . H4 H 0.7258 0.4982 0.4047 0.038 Uiso 1 1 calc R . . C5 C 0.8700(5) 0.3592(5) 0.4389(4) 0.0321(10) Uani 1 1 d . . . C6 C 0.9689(5) 0.2835(4) 0.5236(4) 0.0328(10) Uani 1 1 d . . . H6 H 1.0221 0.2222 0.5116 0.039 Uiso 1 1 calc R . . C7 C 0.4992(5) 0.6391(4) 0.3571(4) 0.0273(9) Uani 1 1 d . . . C8 C 0.4652(4) 0.6520(4) 0.2420(3) 0.0240(8) Uani 1 1 d . . . C9 C 0.3611(5) 0.5775(4) 0.1588(3) 0.0280(9) Uani 1 1 d . . . H9 H 0.3060 0.5205 0.1727 0.034 Uiso 1 1 calc R . . C10 C 0.3385(5) 0.5874(4) 0.0543(4) 0.0308(9) Uani 1 1 d . . . C11 C 0.4244(5) 0.8245(4) 0.5401(3) 0.0313(10) Uani 1 1 d . . . H11 H 0.4114 0.8163 0.4711 0.038 Uiso 1 1 calc R . . C12 C 0.5451(4) 0.7633(4) 0.7193(3) 0.0270(9) Uani 1 1 d . . . H12 H 0.6155 0.7134 0.7753 0.032 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 Cd1 0.0258(2) 0.0253(2) 0.01988(19) -0.00008(11) 0.01372(15) 0.00078(11) F1 0.129(5) 0.148(5) 0.088(4) -0.011(3) 0.070(4) -0.003(4) F2 0.134(5) 0.113(4) 0.090(4) -0.022(3) 0.035(3) -0.034(4) O1 0.0381(19) 0.0382(19) 0.044(2) 0.0030(14) 0.0194(17) 0.0112(14) O2 0.0416(18) 0.043(2) 0.0297(17) 0.0020(14) 0.0109(15) 0.0100(15) O3 0.0384(17) 0.0469(19) 0.0215(15) 0.0008(14) 0.0143(14) -0.0008(15) O4 0.078(3) 0.046(2) 0.047(2) 0.0017(17) 0.046(2) -0.017(2) N1 0.0333(19) 0.0307(19) 0.0317(19) 0.0044(16) 0.0195(16) 0.0060(16) N2 0.0312(18) 0.036(2) 0.0221(17) 0.0017(15) 0.0151(15) 0.0069(16) C1 0.024(2) 0.028(2) 0.036(2) 0.0024(19) 0.0141(19) -0.0010(17) C2 0.025(2) 0.028(2) 0.030(2) -0.0016(17) 0.0128(18) -0.0014(17) C3 0.033(2) 0.029(2) 0.027(2) -0.0001(17) 0.0167(19) 0.0007(17) C4 0.031(2) 0.039(2) 0.027(2) 0.0035(19) 0.0168(18) 0.0054(19) C5 0.030(2) 0.039(2) 0.030(2) -0.0023(19) 0.018(2) -0.0017(19) C6 0.030(2) 0.033(2) 0.040(2) -0.002(2) 0.021(2) 0.0032(19) C7 0.035(2) 0.027(2) 0.025(2) 0.0045(17) 0.020(2) 0.0069(18) C8 0.026(2) 0.026(2) 0.021(2) 0.0025(16) 0.0127(17) 0.0016(17) C9 0.030(2) 0.026(2) 0.029(2) 0.0032(18) 0.0158(18) -0.0026(17) C10 0.035(2) 0.028(2) 0.025(2) -0.0016(18) 0.0129(19) -0.0013(19) C11 0.038(2) 0.037(2) 0.0191(19) -0.0003(18) 0.0154(18) 0.003(2) C12 0.029(2) 0.031(2) 0.022(2) 0.0010(17) 0.0134(17) 0.0054(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O3 2.274(3) . ? Cd1 O4 2.299(3) . ? Cd1 N2 2.333(3) . ? Cd1 O2 2.334(3) 2_756 ? Cd1 N1 2.340(4) . ? Cd1 O1 2.483(4) 2_756 ? Cd1 C1 2.734(4) 2_756 ? F1 C5 1.531(7) . ? F2 C10 1.517(6) . ? O1 C1 1.257(5) . ? O1 Cd1 2.483(4) 2_746 ? O2 C1 1.243(6) . ? O2 Cd1 2.334(3) 2_746 ? O3 C7 1.253(6) . ? O4 C7 1.244(6) 3_666 ? N1 C3 1.338(6) . ? N1 C4 1.344(6) . ? N2 C11 1.337(6) . ? N2 C12 1.340(5) . ? C1 C2 1.505(6) . ? C1 Cd1 2.734(4) 2_746 ? C2 C3 1.384(6) . ? C2 C6 1.393(6) . ? C3 H3 0.9300 . ? C4 C5 1.378(6) . ? C4 H4 0.9300 . ? C5 C6 1.379(7) . ? C6 H6 0.9300 . ? C7 O4 1.244(6) 3_666 ? C7 C8 1.503(6) . ? C8 C9 1.382(6) . ? C8 C12 1.384(6) 4_575 ? C9 C10 1.394(6) . ? C9 H9 0.9300 . ? C10 C11 1.391(7) 4_575 ? C11 C10 1.391(7) 4_576 ? C11 H11 0.9300 . ? C12 C8 1.384(6) 4_576 ? C12 H12 0.9300 . ? 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 Cd1 O4 124.04(13) . . ? O3 Cd1 N2 91.32(12) . . ? O4 Cd1 N2 89.96(14) . . ? O3 Cd1 O2 93.78(12) . 2_756 ? O4 Cd1 O2 142.08(13) . 2_756 ? N2 Cd1 O2 91.99(13) . 2_756 ? O3 Cd1 N1 88.56(12) . . ? O4 Cd1 N1 85.15(14) . . ? N2 Cd1 N1 174.01(13) . . ? O2 Cd1 N1 93.99(13) 2_756 . ? O3 Cd1 O1 147.85(11) . 2_756 ? O4 Cd1 O1 88.10(12) . 2_756 ? N2 Cd1 O1 87.49(12) . 2_756 ? O2 Cd1 O1 54.19(11) 2_756 2_756 ? N1 Cd1 O1 95.79(12) . 2_756 ? O3 Cd1 C1 120.51(13) . 2_756 ? O4 Cd1 C1 115.44(13) . 2_756 ? N2 Cd1 C1 88.04(13) . 2_756 ? O2 Cd1 C1 26.94(12) 2_756 2_756 ? N1 Cd1 C1 97.18(13) . 2_756 ? O1 Cd1 C1 27.35(12) 2_756 2_756 ? C1 O1 Cd1 87.5(3) . 2_746 ? C1 O2 Cd1 94.8(3) . 2_746 ? C7 O3 Cd1 109.3(3) . . ? C7 O4 Cd1 165.5(4) 3_666 . ? C3 N1 C4 117.4(4) . . ? C3 N1 Cd1 119.7(3) . . ? C4 N1 Cd1 122.9(3) . . ? C11 N2 C12 118.1(4) . . ? C11 N2 Cd1 122.8(3) . . ? C12 N2 Cd1 118.9(3) . . ? O2 C1 O1 123.1(4) . . ? O2 C1 C2 117.9(4) . . ? O1 C1 C2 119.0(4) . . ? O2 C1 Cd1 58.3(2) . 2_746 ? O1 C1 Cd1 65.1(2) . 2_746 ? C2 C1 Cd1 171.2(3) . 2_746 ? C3 C2 C6 118.0(4) . . ? C3 C2 C1 119.8(4) . . ? C6 C2 C1 122.2(4) . . ? N1 C3 C2 122.9(4) . . ? N1 C3 H3 118.5 . . ? C2 C3 H3 118.5 . . ? N1 C4 C5 124.2(4) . . ? N1 C4 H4 117.9 . . ? C5 C4 H4 117.9 . . ? C4 C5 C6 117.2(4) . . ? C4 C5 F1 119.4(4) . . ? C6 C5 F1 123.4(4) . . ? C5 C6 C2 120.2(4) . . ? C5 C6 H6 119.9 . . ? C2 C6 H6 119.9 . . ? O4 C7 O3 123.1(4) 3_666 . ? O4 C7 C8 119.4(4) 3_666 . ? O3 C7 C8 117.5(4) . . ? C9 C8 C12 118.8(4) . 4_575 ? C9 C8 C7 122.1(4) . . ? C12 C8 C7 119.0(4) 4_575 . ? C8 C9 C10 120.2(4) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 116.4(4) 4_575 . ? C11 C10 F2 121.6(4) 4_575 . ? C9 C10 F2 122.0(4) . . ? N2 C11 C10 124.2(4) . 4_576 ? N2 C11 H11 117.9 . . ? C10 C11 H11 117.9 4_576 . ? N2 C12 C8 122.2(4) . 4_576 ? N2 C12 H12 118.9 . . ? C8 C12 H12 118.9 4_576 . ? 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 O4 Cd1 O3 C7 -0.7(3) . . . . ? N2 Cd1 O3 C7 -91.5(3) . . . . ? O2 Cd1 O3 C7 176.4(3) 2_756 . . . ? N1 Cd1 O3 C7 82.5(3) . . . . ? O1 Cd1 O3 C7 -178.9(3) 2_756 . . . ? C1 Cd1 O3 C7 180.0(3) 2_756 . . . ? O3 Cd1 O4 C7 -98.7(14) . . . 3_666 ? N2 Cd1 O4 C7 -7.2(14) . . . 3_666 ? O2 Cd1 O4 C7 86.0(14) 2_756 . . 3_666 ? N1 Cd1 O4 C7 176.3(14) . . . 3_666 ? O1 Cd1 O4 C7 80.3(14) 2_756 . . 3_666 ? C1 Cd1 O4 C7 80.6(14) 2_756 . . 3_666 ? O3 Cd1 N1 C3 167.6(3) . . . . ? O4 Cd1 N1 C3 -68.0(3) . . . . ? O2 Cd1 N1 C3 73.9(3) 2_756 . . . ? O1 Cd1 N1 C3 19.5(3) 2_756 . . . ? C1 Cd1 N1 C3 47.0(3) 2_756 . . . ? O3 Cd1 N1 C4 -12.0(4) . . . . ? O4 Cd1 N1 C4 112.3(4) . . . . ? O2 Cd1 N1 C4 -105.7(4) 2_756 . . . ? O1 Cd1 N1 C4 -160.1(3) 2_756 . . . ? C1 Cd1 N1 C4 -132.6(4) 2_756 . . . ? O3 Cd1 N2 C11 10.0(4) . . . . ? O4 Cd1 N2 C11 -114.1(4) . . . . ? O2 Cd1 N2 C11 103.8(4) 2_756 . . . ? O1 Cd1 N2 C11 157.8(4) 2_756 . . . ? C1 Cd1 N2 C11 130.5(4) 2_756 . . . ? O3 Cd1 N2 C12 -164.7(3) . . . . ? O4 Cd1 N2 C12 71.2(3) . . . . ? O2 Cd1 N2 C12 -70.9(3) 2_756 . . . ? O1 Cd1 N2 C12 -16.9(3) 2_756 . . . ? C1 Cd1 N2 C12 -44.2(3) 2_756 . . . ? Cd1 O2 C1 O1 7.2(5) 2_746 . . . ? Cd1 O2 C1 C2 -170.8(3) 2_746 . . . ? Cd1 O1 C1 O2 -6.7(4) 2_746 . . . ? Cd1 O1 C1 C2 171.2(3) 2_746 . . . ? O2 C1 C2 C3 -13.9(6) . . . . ? O1 C1 C2 C3 168.1(4) . . . . ? O2 C1 C2 C6 165.0(4) . . . . ? O1 C1 C2 C6 -13.1(6) . . . . ? C4 N1 C3 C2 0.0(6) . . . . ? Cd1 N1 C3 C2 -179.7(3) . . . . ? C6 C2 C3 N1 -0.4(7) . . . . ? C1 C2 C3 N1 178.5(4) . . . . ? C3 N1 C4 C5 0.0(7) . . . . ? Cd1 N1 C4 C5 179.7(4) . . . . ? N1 C4 C5 C6 0.4(7) . . . . ? N1 C4 C5 F1 -179.5(5) . . . . ? C4 C5 C6 C2 -0.8(7) . . . . ? F1 C5 C6 C2 179.1(5) . . . . ? C3 C2 C6 C5 0.8(7) . . . . ? C1 C2 C6 C5 -178.1(4) . . . . ? Cd1 O3 C7 O4 17.8(5) . . . 3_666 ? Cd1 O3 C7 C8 -160.3(3) . . . . ? O4 C7 C8 C9 -3.5(7) 3_666 . . . ? O3 C7 C8 C9 174.7(4) . . . . ? O4 C7 C8 C12 179.6(4) 3_666 . . 4_575 ? O3 C7 C8 C12 -2.2(6) . . . 4_575 ? C12 C8 C9 C10 0.5(7) 4_575 . . . ? C7 C8 C9 C10 -176.4(4) . . . . ? C8 C9 C10 C11 -0.5(7) . . . 4_575 ? C8 C9 C10 F2 177.8(5) . . . . ? C12 N2 C11 C10 -0.8(7) . . . 4_576 ? Cd1 N2 C11 C10 -175.6(4) . . . 4_576 ? C11 N2 C12 C8 0.9(6) . . . 4_576 ? Cd1 N2 C12 C8 175.9(3) . . . 4_576 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.624 _refine_diff_density_min -1.136 _refine_diff_density_rms 0.135 _database_code_depnum_ccdc_archive 'CCDC 942322' ####################################################################### # # 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 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H6 Cd F2 N2 O4' _chemical_formula_weight 392.59 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 '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 15.1219(8) _cell_length_b 9.4338(5) _cell_length_c 9.0516(5) _cell_angle_alpha 90.00 _cell_angle_beta 113.6880(10) _cell_angle_gamma 90.00 _cell_volume 1182.48(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2774 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 30.44 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 2.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 1.892 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5827 _exptl_absorpt_correction_T_max 0.6809 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 2948 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1053 _reflns_number_gt 1030 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0191P)^2^+2.6697P] 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 1053 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0185 _refine_ls_R_factor_gt 0.0180 _refine_ls_wR_factor_ref 0.0439 _refine_ls_wR_factor_gt 0.0435 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 Cd1 Cd 0.5000 0.38181(2) 0.7500 0.01972(10) Uani 1 2 d S . . F1 F 0.10625(15) 0.4206(3) -0.1880(2) 0.0741(8) Uani 1 1 d . . . O1 O 0.37659(12) 0.3579(2) 0.4966(2) 0.0315(4) Uani 1 1 d . . . O2 O 0.41856(12) 0.4354(2) 0.3012(2) 0.0328(4) Uani 1 1 d . . . N1 N 0.10014(14) 0.2636(2) 0.1672(2) 0.0279(5) Uani 1 1 d . . . C1 C 0.35974(17) 0.3893(2) 0.3531(3) 0.0217(5) Uani 1 1 d . . . C2 C 0.25720(17) 0.3633(2) 0.2302(3) 0.0223(5) Uani 1 1 d . . . C3 C 0.2292(2) 0.4104(3) 0.0731(3) 0.0332(6) Uani 1 1 d . . . H3 H 0.2714 0.4598 0.0403 0.040 Uiso 1 1 calc R . . C4 C 0.1362(2) 0.3808(3) -0.0321(3) 0.0407(8) Uani 1 1 d . . . C5 C 0.07332(19) 0.3091(3) 0.0156(3) 0.0371(7) Uani 1 1 d . . . H5 H 0.0107 0.2918 -0.0590 0.044 Uiso 1 1 calc R . . C6 C 0.19101(17) 0.2907(3) 0.2709(3) 0.0264(5) Uani 1 1 d . . . H6 H 0.2106 0.2586 0.3765 0.032 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 Cd1 0.01176(14) 0.02836(16) 0.01825(14) 0.000 0.00519(10) 0.000 F1 0.0540(12) 0.1145(18) 0.0287(9) 0.0300(11) -0.0095(9) -0.0430(12) O1 0.0179(9) 0.0534(12) 0.0198(9) 0.0005(8) 0.0040(7) -0.0059(8) O2 0.0203(9) 0.0419(11) 0.0365(10) 0.0058(9) 0.0119(8) -0.0072(8) N1 0.0190(10) 0.0372(12) 0.0233(11) 0.0024(9) 0.0041(9) -0.0061(9) C1 0.0158(12) 0.0253(12) 0.0225(13) -0.0011(9) 0.0061(10) -0.0007(9) C2 0.0182(12) 0.0261(13) 0.0217(12) -0.0019(10) 0.0070(10) -0.0024(10) C3 0.0286(14) 0.0414(16) 0.0269(14) 0.0048(11) 0.0084(12) -0.0113(12) C4 0.0354(16) 0.0545(19) 0.0222(14) 0.0126(12) 0.0010(12) -0.0147(13) C5 0.0230(13) 0.0492(17) 0.0270(14) 0.0094(12) -0.0025(11) -0.0119(12) C6 0.0200(12) 0.0360(14) 0.0205(12) 0.0037(10) 0.0053(10) -0.0040(10) _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 Cd1 O2 2.2723(18) 5_666 ? Cd1 O2 2.2723(18) 6_566 ? Cd1 O1 2.3140(17) . ? Cd1 O1 2.3140(17) 2_656 ? Cd1 N1 2.376(2) 8_556 ? Cd1 N1 2.376(2) 7_556 ? F1 C4 1.350(3) . ? O1 C1 1.255(3) . ? O2 C1 1.240(3) . ? O2 Cd1 2.2723(18) 5_666 ? N1 C5 1.336(3) . ? N1 C6 1.341(3) . ? N1 Cd1 2.376(2) 7_556 ? C1 C2 1.522(3) . ? C2 C6 1.380(3) . ? C2 C3 1.384(4) . ? C3 C4 1.374(4) . ? C3 H3 0.9300 . ? C4 C5 1.370(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? 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 Cd1 O2 81.27(10) 5_666 6_566 ? O2 Cd1 O1 99.16(6) 5_666 . ? O2 Cd1 O1 89.35(7) 6_566 . ? O2 Cd1 O1 89.35(7) 5_666 2_656 ? O2 Cd1 O1 99.16(6) 6_566 2_656 ? O1 Cd1 O1 168.82(10) . 2_656 ? O2 Cd1 N1 84.69(7) 5_666 8_556 ? O2 Cd1 N1 165.58(8) 6_566 8_556 ? O1 Cd1 N1 89.64(7) . 8_556 ? O1 Cd1 N1 83.91(6) 2_656 8_556 ? O2 Cd1 N1 165.58(7) 5_666 7_556 ? O2 Cd1 N1 84.69(7) 6_566 7_556 ? O1 Cd1 N1 83.91(7) . 7_556 ? O1 Cd1 N1 89.64(7) 2_656 7_556 ? N1 Cd1 N1 109.50(11) 8_556 7_556 ? C1 O1 Cd1 138.64(16) . . ? C1 O2 Cd1 150.88(18) . 5_666 ? C5 N1 C6 117.4(2) . . ? C5 N1 Cd1 122.71(16) . 7_556 ? C6 N1 Cd1 119.55(16) . 7_556 ? O2 C1 O1 126.7(2) . . ? O2 C1 C2 117.1(2) . . ? O1 C1 C2 116.2(2) . . ? C6 C2 C3 118.6(2) . . ? C6 C2 C1 121.4(2) . . ? C3 C2 C1 120.0(2) . . ? C4 C3 C2 116.9(2) . . ? C4 C3 H3 121.5 . . ? C2 C3 H3 121.5 . . ? F1 C4 C5 118.9(2) . . ? F1 C4 C3 119.2(3) . . ? C5 C4 C3 121.9(3) . . ? N1 C5 C4 121.3(2) . . ? N1 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? N1 C6 C2 123.9(2) . . ? N1 C6 H6 118.1 . . ? C2 C6 H6 118.1 . . ? 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 Cd1 O1 C1 21.1(3) 5_666 . . . ? O2 Cd1 O1 C1 102.2(3) 6_566 . . . ? O1 Cd1 O1 C1 -118.1(3) 2_656 . . . ? N1 Cd1 O1 C1 -63.5(3) 8_556 . . . ? N1 Cd1 O1 C1 -173.1(3) 7_556 . . . ? Cd1 O2 C1 O1 -85.2(4) 5_666 . . . ? Cd1 O2 C1 C2 97.0(4) 5_666 . . . ? Cd1 O1 C1 O2 9.7(4) . . . . ? Cd1 O1 C1 C2 -172.42(17) . . . . ? O2 C1 C2 C6 169.1(2) . . . . ? O1 C1 C2 C6 -9.0(4) . . . . ? O2 C1 C2 C3 -9.7(4) . . . . ? O1 C1 C2 C3 172.3(2) . . . . ? C6 C2 C3 C4 0.0(4) . . . . ? C1 C2 C3 C4 178.8(3) . . . . ? C2 C3 C4 F1 -178.0(3) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? C6 N1 C5 C4 0.0(4) . . . . ? Cd1 N1 C5 C4 -173.4(2) 7_556 . . . ? F1 C4 C5 N1 178.0(3) . . . . ? C3 C4 C5 N1 -0.5(5) . . . . ? C5 N1 C6 C2 0.6(4) . . . . ? Cd1 N1 C6 C2 174.2(2) 7_556 . . . ? C3 C2 C6 N1 -0.6(4) . . . . ? C1 C2 C6 N1 -179.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.717 _refine_diff_density_min -0.527 _refine_diff_density_rms 0.094 _database_code_depnum_ccdc_archive 'CCDC 942323' ####################################################################### # # 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_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Cd Cl F N2 O3' _chemical_formula_weight 361.04 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' F F 0.0171 0.0103 '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' Cd Cd -0.8075 1.2024 '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 13.9287(15) _cell_length_b 12.7175(14) _cell_length_c 6.9109(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.088(2) _cell_angle_gamma 90.00 _cell_volume 1219.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3869 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 30.20 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.967 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 2.019 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6017 _exptl_absorpt_correction_T_max 0.6882 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 6148 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2158 _reflns_number_gt 1945 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0180P)^2^+0.6638P] 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 2158 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0210 _refine_ls_R_factor_gt 0.0178 _refine_ls_wR_factor_ref 0.0418 _refine_ls_wR_factor_gt 0.0405 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 Cd1 Cd 0.220482(11) 1.160286(12) 0.15423(2) 0.02389(7) Uani 1 1 d . . . Cl1 Cl 0.32459(4) 1.29443(5) -0.02078(8) 0.02947(14) Uani 1 1 d . . . F1 F 0.21561(14) 0.83135(17) 0.6780(3) 0.1011(10) Uani 1 1 d . . . O1 O -0.12651(12) 0.90156(13) 0.1183(2) 0.0344(4) Uani 1 1 d . . . O2 O -0.09438(12) 0.75943(14) 0.3042(3) 0.0428(5) Uani 1 1 d . . . O3 O 0.32348(13) 1.02413(13) 0.0910(3) 0.0379(4) Uani 1 1 d . . . N1 N 0.14339(14) 1.02320(15) 0.3193(3) 0.0291(4) Uani 1 1 d . . . N2 N 0.40548(15) 0.93718(16) -0.1259(3) 0.0381(5) Uani 1 1 d . . . C1 C -0.07653(17) 0.84893(18) 0.2408(4) 0.0279(5) Uani 1 1 d . . . C2 C 0.01960(16) 0.89291(18) 0.3230(3) 0.0265(5) Uani 1 1 d . . . C3 C 0.0737(2) 0.8396(2) 0.4681(4) 0.0427(7) Uani 1 1 d . . . H3 H 0.0515 0.7772 0.5186 0.051 Uiso 1 1 calc R . . C4 C 0.1602(2) 0.8804(2) 0.5351(5) 0.0514(8) Uani 1 1 d . . . C5 C 0.19416(19) 0.9714(2) 0.4593(4) 0.0427(7) Uani 1 1 d . . . H5 H 0.2541 0.9972 0.5074 0.051 Uiso 1 1 calc R . . C6 C 0.05728(16) 0.98527(18) 0.2544(3) 0.0276(5) Uani 1 1 d . . . H6 H 0.0207 1.0225 0.1583 0.033 Uiso 1 1 calc R . . C7 C 0.35816(17) 1.01904(19) -0.0668(4) 0.0331(6) Uani 1 1 d . . . H7 H 0.3504 1.0767 -0.1493 0.040 Uiso 1 1 calc R . . C8 C 0.4460(2) 0.9368(3) -0.3127(4) 0.0548(8) Uani 1 1 d . . . H8A H 0.4123 0.8865 -0.3970 0.082 Uiso 1 1 calc R . . H8B H 0.5130 0.9183 -0.2944 0.082 Uiso 1 1 calc R . . H8C H 0.4395 1.0055 -0.3699 0.082 Uiso 1 1 calc R . . C9 C 0.4147(2) 0.8424(2) -0.0095(5) 0.0603(9) Uani 1 1 d . . . H9A H 0.4016 0.8582 0.1214 0.090 Uiso 1 1 calc R . . H9B H 0.4791 0.8154 -0.0097 0.090 Uiso 1 1 calc R . . H9C H 0.3697 0.7907 -0.0629 0.090 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 Cd1 0.02107(10) 0.02266(10) 0.02767(11) -0.00093(7) 0.00070(7) 0.00079(7) Cl1 0.0290(3) 0.0297(3) 0.0290(3) 0.0043(2) -0.0013(2) -0.0022(2) F1 0.0711(15) 0.0962(17) 0.124(2) 0.0750(15) -0.0600(14) -0.0388(12) O1 0.0323(10) 0.0354(10) 0.0338(10) -0.0016(8) -0.0065(8) -0.0054(8) O2 0.0321(10) 0.0391(10) 0.0562(12) 0.0100(9) -0.0022(9) -0.0149(8) O3 0.0394(10) 0.0370(10) 0.0379(11) 0.0007(8) 0.0068(8) 0.0126(8) N1 0.0261(11) 0.0272(10) 0.0332(11) 0.0026(9) -0.0027(9) -0.0056(9) N2 0.0348(12) 0.0344(12) 0.0454(14) -0.0074(10) 0.0049(10) 0.0048(10) C1 0.0260(13) 0.0310(13) 0.0275(13) -0.0064(11) 0.0074(10) -0.0057(10) C2 0.0251(12) 0.0288(12) 0.0257(12) -0.0030(10) 0.0027(10) -0.0046(10) C3 0.0384(16) 0.0396(15) 0.0486(17) 0.0155(13) -0.0054(13) -0.0139(12) C4 0.0424(17) 0.0494(17) 0.0577(19) 0.0274(15) -0.0220(14) -0.0102(14) C5 0.0293(14) 0.0431(15) 0.0529(18) 0.0114(14) -0.0112(13) -0.0101(12) C6 0.0255(13) 0.0296(12) 0.0273(12) 0.0002(10) 0.0005(10) -0.0013(10) C7 0.0297(13) 0.0305(13) 0.0385(15) -0.0014(11) -0.0010(11) 0.0041(11) C8 0.0421(18) 0.070(2) 0.0528(19) -0.0166(16) 0.0108(15) 0.0098(15) C9 0.065(2) 0.0360(17) 0.080(3) 0.0048(16) 0.0076(19) 0.0169(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. ; 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 Cd1 O2 2.2015(16) 2 ? Cd1 O3 2.3149(16) . ? Cd1 O1 2.3329(17) 3_575 ? Cd1 N1 2.3898(19) . ? Cd1 Cl1 2.6052(6) . ? Cd1 Cl1 2.6270(6) 4_586 ? Cl1 Cd1 2.6270(6) 4_585 ? F1 C4 1.351(3) . ? O1 C1 1.243(3) . ? O1 Cd1 2.3329(16) 3_575 ? O2 C1 1.253(3) . ? O2 Cd1 2.2015(16) 2_545 ? O3 C7 1.232(3) . ? N1 C5 1.322(3) . ? N1 C6 1.333(3) . ? N2 C7 1.316(3) . ? N2 C9 1.449(3) . ? N2 C8 1.454(3) . ? C1 C2 1.514(3) . ? C2 C3 1.379(4) . ? C2 C6 1.387(3) . ? C3 C4 1.354(4) . ? C3 H3 0.9300 . ? C4 C5 1.372(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? 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 Cd1 O3 165.47(7) 2 . ? O2 Cd1 O1 84.34(7) 2 3_575 ? O3 Cd1 O1 84.73(6) . 3_575 ? O2 Cd1 N1 87.60(7) 2 . ? O3 Cd1 N1 81.76(7) . . ? O1 Cd1 N1 84.02(6) 3_575 . ? O2 Cd1 Cl1 99.72(5) 2 . ? O3 Cd1 Cl1 91.28(5) . . ? O1 Cd1 Cl1 98.13(4) 3_575 . ? N1 Cd1 Cl1 172.52(5) . . ? O2 Cd1 Cl1 98.58(5) 2 4_586 ? O3 Cd1 Cl1 91.21(5) . 4_586 ? O1 Cd1 Cl1 172.67(4) 3_575 4_586 ? N1 Cd1 Cl1 89.37(5) . 4_586 ? Cl1 Cd1 Cl1 88.028(17) . 4_586 ? Cd1 Cl1 Cd1 104.64(2) . 4_585 ? C1 O1 Cd1 127.49(15) . 3_575 ? C1 O2 Cd1 138.73(17) . 2_545 ? C7 O3 Cd1 120.29(16) . . ? C5 N1 C6 118.2(2) . . ? C5 N1 Cd1 118.61(16) . . ? C6 N1 Cd1 122.15(16) . . ? C7 N2 C9 120.5(2) . . ? C7 N2 C8 121.5(2) . . ? C9 N2 C8 117.9(2) . . ? O1 C1 O2 127.7(2) . . ? O1 C1 C2 118.7(2) . . ? O2 C1 C2 113.6(2) . . ? C3 C2 C6 117.8(2) . . ? C3 C2 C1 120.0(2) . . ? C6 C2 C1 122.2(2) . . ? C4 C3 C2 118.2(2) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? F1 C4 C3 120.4(2) . . ? F1 C4 C5 118.3(2) . . ? C3 C4 C5 121.3(3) . . ? N1 C5 C4 121.3(2) . . ? N1 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? N1 C6 C2 123.2(2) . . ? N1 C6 H6 118.4 . . ? C2 C6 H6 118.4 . . ? O3 C7 N2 124.2(2) . . ? O3 C7 H7 117.9 . . ? N2 C7 H7 117.9 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 Cd1 Cl1 Cd1 -62.32(5) 2 . . 4_585 ? O3 Cd1 Cl1 Cd1 108.14(5) . . . 4_585 ? O1 Cd1 Cl1 Cd1 23.29(5) 3_575 . . 4_585 ? Cl1 Cd1 Cl1 Cd1 -160.69(2) 4_586 . . 4_585 ? O2 Cd1 O3 C7 99.8(3) 2 . . . ? O1 Cd1 O3 C7 58.47(19) 3_575 . . . ? N1 Cd1 O3 C7 143.18(19) . . . . ? Cl1 Cd1 O3 C7 -39.58(18) . . . . ? Cl1 Cd1 O3 C7 -127.63(18) 4_586 . . . ? O2 Cd1 N1 C5 -132.3(2) 2 . . . ? O3 Cd1 N1 C5 57.6(2) . . . . ? O1 Cd1 N1 C5 143.1(2) 3_575 . . . ? Cl1 Cd1 N1 C5 -33.7(2) 4_586 . . . ? O2 Cd1 N1 C6 59.37(18) 2 . . . ? O3 Cd1 N1 C6 -110.70(18) . . . . ? O1 Cd1 N1 C6 -25.18(18) 3_575 . . . ? Cl1 Cd1 N1 C6 157.99(18) 4_586 . . . ? Cd1 O1 C1 O2 -35.7(3) 3_575 . . . ? Cd1 O1 C1 C2 142.13(16) 3_575 . . . ? Cd1 O2 C1 O1 -26.5(4) 2_545 . . . ? Cd1 O2 C1 C2 155.63(18) 2_545 . . . ? O1 C1 C2 C3 175.8(2) . . . . ? O2 C1 C2 C3 -6.1(3) . . . . ? O1 C1 C2 C6 -5.7(3) . . . . ? O2 C1 C2 C6 172.4(2) . . . . ? C6 C2 C3 C4 0.1(4) . . . . ? C1 C2 C3 C4 178.7(3) . . . . ? C2 C3 C4 F1 179.6(3) . . . . ? C2 C3 C4 C5 -1.0(5) . . . . ? C6 N1 C5 C4 0.7(4) . . . . ? Cd1 N1 C5 C4 -168.0(2) . . . . ? F1 C4 C5 N1 -180.0(3) . . . . ? C3 C4 C5 N1 0.6(5) . . . . ? C5 N1 C6 C2 -1.7(4) . . . . ? Cd1 N1 C6 C2 166.62(17) . . . . ? C3 C2 C6 N1 1.3(4) . . . . ? C1 C2 C6 N1 -177.3(2) . . . . ? Cd1 O3 C7 N2 -169.59(19) . . . . ? C9 N2 C7 O3 3.9(4) . . . . ? C8 N2 C7 O3 -179.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.399 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 942324' ####################################################################### # # 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_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H6 Cd Cl2 N2 O4' _chemical_formula_weight 425.49 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' Cd Cd -0.8075 1.2024 '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 11.1319(6) _cell_length_b 9.9512(5) _cell_length_c 14.2568(6) _cell_angle_alpha 90.00 _cell_angle_beta 120.015(3) _cell_angle_gamma 90.00 _cell_volume 1367.51(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3526 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 28.60 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 2.067 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 2.003 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5666 _exptl_absorpt_correction_T_max 0.6670 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 6799 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2412 _reflns_number_gt 2128 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0198P)^2^+0.5191P] 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 2412 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0233 _refine_ls_R_factor_gt 0.0191 _refine_ls_wR_factor_ref 0.0445 _refine_ls_wR_factor_gt 0.0430 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 Cd1 Cd 0.816144(17) 0.879708(18) 0.403038(13) 0.02880(7) Uani 1 1 d . . . Cl1 Cl 0.33476(8) 0.65468(9) -0.19566(6) 0.0561(2) Uani 1 1 d . . . Cl2 Cl 1.27846(8) 0.49494(8) 0.55294(5) 0.05255(19) Uani 1 1 d . . . O1 O 0.6278(2) 0.74164(19) 0.30999(15) 0.0464(5) Uani 1 1 d . . . O2 O 0.6606(2) 0.87362(19) 0.20150(16) 0.0501(5) Uani 1 1 d . . . O3 O 0.90441(18) 0.8047(2) 0.57347(13) 0.0422(5) Uani 1 1 d . . . O4 O 0.9142(2) 1.0641(2) 0.37382(16) 0.0561(6) Uani 1 1 d . . . N1 N 0.3120(2) 0.5346(2) 0.05803(16) 0.0344(5) Uani 1 1 d . . . N2 N 0.9691(2) 0.7430(2) 0.37935(16) 0.0362(5) Uani 1 1 d . . . C1 C 0.5997(3) 0.7790(3) 0.2175(2) 0.0366(6) Uani 1 1 d . . . C2 C 0.4894(2) 0.7022(2) 0.1222(2) 0.0327(6) Uani 1 1 d . . . C3 C 0.4682(3) 0.7203(3) 0.0189(2) 0.0382(6) Uani 1 1 d . . . H3 H 0.5196 0.7829 0.0053 0.046 Uiso 1 1 calc R . . C4 C 0.3687(3) 0.6428(3) -0.0634(2) 0.0363(6) Uani 1 1 d . . . C5 C 0.2936(3) 0.5509(3) -0.0411(2) 0.0362(6) Uani 1 1 d . . . H5 H 0.2277 0.4985 -0.0973 0.043 Uiso 1 1 calc R . . C6 C 0.4098(3) 0.6087(2) 0.1383(2) 0.0353(6) Uani 1 1 d . . . H6 H 0.4247 0.5967 0.2081 0.042 Uiso 1 1 calc R . . C7 C 1.0093(3) 0.8665(2) 0.6443(2) 0.0328(6) Uani 1 1 d . . . C8 C 1.0377(2) 0.8520(2) 0.75909(19) 0.0295(5) Uani 1 1 d . . . C9 C 0.9539(3) 0.7300(2) 0.28053(19) 0.0339(6) Uani 1 1 d . . . H9 H 0.8839 0.7784 0.2237 0.041 Uiso 1 1 calc R . . C10 C 1.0687(3) 0.6711(3) 0.4602(2) 0.0382(6) Uani 1 1 d . . . H10 H 1.0794 0.6775 0.5291 0.046 Uiso 1 1 calc R . . C11 C 1.1556(3) 0.5879(3) 0.44446(19) 0.0355(6) Uani 1 1 d . . . C12 C 1.1422(3) 0.9236(3) 0.84361(19) 0.0335(6) Uani 1 1 d . . . H12 H 1.2019 0.9781 0.8325 0.040 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 Cd1 0.03099(11) 0.03478(12) 0.02299(10) -0.00012(7) 0.01526(8) 0.00191(8) Cl1 0.0590(5) 0.0822(6) 0.0362(4) 0.0077(4) 0.0307(4) -0.0014(4) Cl2 0.0584(4) 0.0543(4) 0.0315(4) 0.0107(3) 0.0124(3) 0.0205(4) O1 0.0462(11) 0.0473(12) 0.0343(10) -0.0015(9) 0.0114(9) -0.0085(9) O2 0.0448(11) 0.0500(13) 0.0508(12) -0.0023(9) 0.0203(10) -0.0169(10) O3 0.0441(11) 0.0572(12) 0.0235(9) 0.0001(8) 0.0155(9) -0.0018(10) O4 0.0873(15) 0.0535(12) 0.0489(12) 0.0023(10) 0.0501(12) -0.0190(12) N1 0.0365(11) 0.0390(13) 0.0320(11) -0.0017(9) 0.0203(10) -0.0058(10) N2 0.0403(12) 0.0452(13) 0.0265(11) 0.0004(9) 0.0192(10) 0.0108(11) C1 0.0309(13) 0.0327(15) 0.0424(16) -0.0007(12) 0.0156(12) 0.0027(12) C2 0.0297(13) 0.0326(14) 0.0337(14) 0.0027(11) 0.0142(11) 0.0018(11) C3 0.0363(14) 0.0370(15) 0.0434(16) 0.0053(12) 0.0214(13) -0.0015(12) C4 0.0365(14) 0.0456(16) 0.0312(14) 0.0037(12) 0.0204(12) 0.0021(13) C5 0.0350(14) 0.0441(16) 0.0317(14) -0.0033(12) 0.0183(12) -0.0045(12) C6 0.0364(14) 0.0367(15) 0.0299(13) 0.0003(11) 0.0142(12) -0.0008(12) C7 0.0392(14) 0.0335(14) 0.0271(13) 0.0022(11) 0.0175(12) 0.0068(12) C8 0.0317(13) 0.0331(14) 0.0254(12) 0.0027(10) 0.0156(11) 0.0022(11) C9 0.0357(14) 0.0400(15) 0.0262(13) 0.0032(11) 0.0156(11) 0.0067(12) C10 0.0452(15) 0.0474(16) 0.0228(13) -0.0014(11) 0.0176(12) 0.0040(13) C11 0.0376(14) 0.0376(15) 0.0262(13) 0.0035(11) 0.0122(12) 0.0060(12) C12 0.0356(14) 0.0343(14) 0.0317(14) 0.0008(11) 0.0177(12) -0.0058(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 Cd1 O3 2.2445(17) . ? Cd1 O4 2.2776(19) . ? Cd1 O1 2.2938(18) . ? Cd1 N2 2.332(2) . ? Cd1 N1 2.347(2) 2_655 ? Cd1 O2 2.506(2) . ? Cd1 C1 2.726(3) . ? Cl1 C4 1.732(3) . ? Cl2 C11 1.733(2) . ? O1 C1 1.250(3) . ? O2 C1 1.247(3) . ? O3 C7 1.257(3) . ? O4 C7 1.220(3) 3_776 ? N1 C5 1.333(3) . ? N1 C6 1.339(3) . ? N1 Cd1 2.347(2) 2_645 ? N2 C10 1.339(3) . ? N2 C9 1.339(3) . ? C1 C2 1.506(3) . ? C2 C6 1.381(3) . ? C2 C3 1.382(3) . ? C3 C4 1.377(4) . ? C3 H3 0.9300 . ? C4 C5 1.379(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O4 1.220(3) 3_776 ? C7 C8 1.511(3) . ? C8 C12 1.383(3) . ? C8 C9 1.384(3) 4_576 ? C9 C8 1.384(3) 4_575 ? C9 H9 0.9300 . ? C10 C11 1.374(4) . ? C10 H10 0.9300 . ? C11 C12 1.374(3) 4_575 ? C12 C11 1.374(3) 4_576 ? C12 H12 0.9300 . ? 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 Cd1 O4 118.40(7) . . ? O3 Cd1 O1 101.85(7) . . ? O4 Cd1 O1 139.46(7) . . ? O3 Cd1 N2 90.39(7) . . ? O4 Cd1 N2 89.57(8) . . ? O1 Cd1 N2 95.11(7) . . ? O3 Cd1 N1 87.19(7) . 2_655 ? O4 Cd1 N1 85.27(8) . 2_655 ? O1 Cd1 N1 92.42(7) . 2_655 ? N2 Cd1 N1 172.42(7) . 2_655 ? O3 Cd1 O2 155.56(7) . . ? O4 Cd1 O2 85.95(7) . . ? O1 Cd1 O2 54.19(6) . . ? N2 Cd1 O2 87.46(7) . . ? N1 Cd1 O2 97.69(7) 2_655 . ? O3 Cd1 C1 128.60(8) . . ? O4 Cd1 C1 113.01(8) . . ? O1 Cd1 C1 27.11(7) . . ? N2 Cd1 C1 90.00(7) . . ? N1 Cd1 C1 97.13(7) 2_655 . ? O2 Cd1 C1 27.15(7) . . ? C1 O1 Cd1 96.09(16) . . ? C1 O2 Cd1 86.30(16) . . ? C7 O3 Cd1 115.75(16) . . ? C7 O4 Cd1 160.7(2) 3_776 . ? C5 N1 C6 117.9(2) . . ? C5 N1 Cd1 122.80(17) . 2_645 ? C6 N1 Cd1 119.33(16) . 2_645 ? C10 N2 C9 117.9(2) . . ? C10 N2 Cd1 122.53(16) . . ? C9 N2 Cd1 119.48(16) . . ? O2 C1 O1 123.1(2) . . ? O2 C1 C2 119.4(2) . . ? O1 C1 C2 117.5(2) . . ? O2 C1 Cd1 66.55(14) . . ? O1 C1 Cd1 56.79(13) . . ? C2 C1 Cd1 171.11(18) . . ? C6 C2 C3 118.9(2) . . ? C6 C2 C1 119.5(2) . . ? C3 C2 C1 121.6(2) . . ? C4 C3 C2 118.1(2) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? C3 C4 C5 119.8(2) . . ? C3 C4 Cl1 122.2(2) . . ? C5 C4 Cl1 118.0(2) . . ? N1 C5 C4 122.4(2) . . ? N1 C5 H5 118.8 . . ? C4 C5 H5 118.8 . . ? N1 C6 C2 122.9(2) . . ? N1 C6 H6 118.5 . . ? C2 C6 H6 118.5 . . ? O4 C7 O3 125.0(2) 3_776 . ? O4 C7 C8 119.5(2) 3_776 . ? O3 C7 C8 115.5(2) . . ? C12 C8 C9 118.6(2) . 4_576 ? C12 C8 C7 121.6(2) . . ? C9 C8 C7 119.8(2) 4_576 . ? N2 C9 C8 123.1(2) . 4_575 ? N2 C9 H9 118.5 . . ? C8 C9 H9 118.5 4_575 . ? N2 C10 C11 121.9(2) . . ? N2 C10 H10 119.0 . . ? C11 C10 H10 119.0 . . ? C10 C11 C12 120.3(2) . 4_575 ? C10 C11 Cl2 118.78(19) . . ? C12 C11 Cl2 120.9(2) 4_575 . ? C11 C12 C8 118.2(2) 4_576 . ? C11 C12 H12 120.9 4_576 . ? C8 C12 H12 120.9 . . ? 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 O3 Cd1 O1 C1 -171.40(15) . . . . ? O4 Cd1 O1 C1 15.4(2) . . . . ? N2 Cd1 O1 C1 -79.93(16) . . . . ? N1 Cd1 O1 C1 100.96(16) 2_655 . . . ? O2 Cd1 O1 C1 3.22(14) . . . . ? O3 Cd1 O2 C1 9.6(3) . . . . ? O4 Cd1 O2 C1 -175.30(16) . . . . ? O1 Cd1 O2 C1 -3.21(14) . . . . ? N2 Cd1 O2 C1 94.95(16) . . . . ? N1 Cd1 O2 C1 -90.64(15) 2_655 . . . ? O4 Cd1 O3 C7 -3.1(2) . . . . ? O1 Cd1 O3 C7 -178.09(17) . . . . ? N2 Cd1 O3 C7 86.60(18) . . . . ? N1 Cd1 O3 C7 -86.21(18) 2_655 . . . ? O2 Cd1 O3 C7 171.32(16) . . . . ? C1 Cd1 O3 C7 176.91(16) . . . . ? O3 Cd1 O4 C7 88.9(6) . . . 3_776 ? O1 Cd1 O4 C7 -98.7(6) . . . 3_776 ? N2 Cd1 O4 C7 -1.3(6) . . . 3_776 ? N1 Cd1 O4 C7 173.1(6) 2_655 . . 3_776 ? O2 Cd1 O4 C7 -88.8(6) . . . 3_776 ? C1 Cd1 O4 C7 -91.2(6) . . . 3_776 ? O3 Cd1 N2 C10 -5.6(2) . . . . ? O4 Cd1 N2 C10 112.7(2) . . . . ? O1 Cd1 N2 C10 -107.6(2) . . . . ? O2 Cd1 N2 C10 -161.3(2) . . . . ? C1 Cd1 N2 C10 -134.2(2) . . . . ? O3 Cd1 N2 C9 171.17(19) . . . . ? O4 Cd1 N2 C9 -70.44(19) . . . . ? O1 Cd1 N2 C9 69.23(19) . . . . ? O2 Cd1 N2 C9 15.52(19) . . . . ? C1 Cd1 N2 C9 42.57(19) . . . . ? Cd1 O2 C1 O1 5.7(3) . . . . ? Cd1 O2 C1 C2 -172.6(2) . . . . ? Cd1 O1 C1 O2 -6.3(3) . . . . ? Cd1 O1 C1 C2 172.05(18) . . . . ? O3 Cd1 C1 O2 -174.94(13) . . . . ? O4 Cd1 C1 O2 5.09(17) . . . . ? O1 Cd1 C1 O2 174.3(3) . . . . ? N2 Cd1 C1 O2 -84.44(15) . . . . ? N1 Cd1 C1 O2 92.96(15) 2_655 . . . ? O3 Cd1 C1 O1 10.79(19) . . . . ? O4 Cd1 C1 O1 -169.19(15) . . . . ? N2 Cd1 C1 O1 101.28(16) . . . . ? N1 Cd1 C1 O1 -81.32(16) 2_655 . . . ? O2 Cd1 C1 O1 -174.3(3) . . . . ? O2 C1 C2 C6 -171.9(2) . . . . ? O1 C1 C2 C6 9.7(4) . . . . ? O2 C1 C2 C3 9.9(4) . . . . ? O1 C1 C2 C3 -168.5(2) . . . . ? C6 C2 C3 C4 -0.5(4) . . . . ? C1 C2 C3 C4 177.7(2) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C2 C3 C4 Cl1 -179.02(19) . . . . ? C6 N1 C5 C4 -1.6(4) . . . . ? Cd1 N1 C5 C4 179.57(19) 2_645 . . . ? C3 C4 C5 N1 0.9(4) . . . . ? Cl1 C4 C5 N1 -179.9(2) . . . . ? C5 N1 C6 C2 1.3(4) . . . . ? Cd1 N1 C6 C2 -179.83(18) 2_645 . . . ? C3 C2 C6 N1 -0.3(4) . . . . ? C1 C2 C6 N1 -178.5(2) . . . . ? Cd1 O3 C7 O4 -20.4(3) . . . 3_776 ? Cd1 O3 C7 C8 158.95(15) . . . . ? O4 C7 C8 C12 5.1(4) 3_776 . . . ? O3 C7 C8 C12 -174.3(2) . . . . ? O4 C7 C8 C9 -177.9(2) 3_776 . . 4_576 ? O3 C7 C8 C9 2.8(3) . . . 4_576 ? C10 N2 C9 C8 -1.2(4) . . . 4_575 ? Cd1 N2 C9 C8 -178.12(18) . . . 4_575 ? C9 N2 C10 C11 1.2(4) . . . . ? Cd1 N2 C10 C11 178.1(2) . . . . ? N2 C10 C11 C12 0.0(4) . . . 4_575 ? N2 C10 C11 Cl2 -178.2(2) . . . . ? C9 C8 C12 C11 -1.5(4) 4_576 . . 4_576 ? C7 C8 C12 C11 175.6(2) . . . 4_576 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.269 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 942325' ####################################################################### # # 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_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Cd Cl2 N2 O6' _chemical_formula_weight 461.52 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' Cd Cd -0.8075 1.2024 '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 5.6741(14) _cell_length_b 9.260(2) _cell_length_c 15.044(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.330(8) _cell_angle_gamma 90.00 _cell_volume 765.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3002 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 30.36 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 2.001 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 1.806 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5470 _exptl_absorpt_correction_T_max 0.6134 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 3807 _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1350 _reflns_number_gt 1246 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0213P)^2^+0.3745P] 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 0.0214(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1350 _refine_ls_number_parameters 107 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0180 _refine_ls_R_factor_gt 0.0161 _refine_ls_wR_factor_ref 0.0439 _refine_ls_wR_factor_gt 0.0426 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 Cd1 Cd 1.0000 0.5000 1.0000 0.02027(11) Uani 1 2 d S . . Cl1 Cl 0.35853(12) 1.00772(6) 0.87545(4) 0.03940(16) Uani 1 1 d . . . O1 O 0.8322(2) 0.91115(15) 0.61329(9) 0.0274(3) Uani 1 1 d . . . O2 O 1.1280(3) 0.75798(19) 0.67811(11) 0.0440(4) Uani 1 1 d . . . O3 O 1.3386(3) 0.64093(16) 1.05062(10) 0.0333(3) Uani 1 1 d . . . H3A H 1.4816 0.6079 1.0711 0.040 Uiso 1 1 d R . . H3B H 1.2854 0.6901 1.0893 0.040 Uiso 1 1 d R . . N1 N 0.8365(3) 0.69152(18) 0.89924(10) 0.0271(4) Uani 1 1 d . . . C1 C 0.9434(4) 0.8293(2) 0.67755(13) 0.0256(4) Uani 1 1 d . . . C2 C 0.8398(3) 0.8193(2) 0.76076(12) 0.0230(4) Uani 1 1 d . . . C3 C 0.9222(4) 0.7111(2) 0.82467(13) 0.0266(4) Uani 1 1 d . . . H3 H 1.0429 0.6492 0.8153 0.032 Uiso 1 1 calc R . . C4 C 0.6667(4) 0.7828(2) 0.91294(13) 0.0288(4) Uani 1 1 d . . . H4 H 0.6052 0.7706 0.9643 0.035 Uiso 1 1 calc R . . C5 C 0.5801(4) 0.8944(2) 0.85323(13) 0.0266(4) Uani 1 1 d . . . C6 C 0.6653(4) 0.9140(2) 0.77561(13) 0.0259(4) Uani 1 1 d . . . H6 H 0.6069 0.9886 0.7347 0.031 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 Cd1 0.02499(14) 0.02219(14) 0.01529(14) 0.00124(7) 0.00817(8) 0.00234(7) Cl1 0.0455(4) 0.0408(3) 0.0355(3) 0.0026(2) 0.0169(3) 0.0172(2) O1 0.0309(7) 0.0335(8) 0.0196(7) 0.0059(6) 0.0102(6) -0.0033(6) O2 0.0453(9) 0.0533(11) 0.0418(9) 0.0191(8) 0.0269(8) 0.0161(8) O3 0.0281(7) 0.0417(9) 0.0323(8) -0.0064(7) 0.0119(6) -0.0039(6) N1 0.0352(9) 0.0282(9) 0.0202(8) 0.0052(7) 0.0112(7) 0.0044(7) C1 0.0294(11) 0.0262(10) 0.0238(10) 0.0008(8) 0.0115(8) -0.0045(8) C2 0.0270(10) 0.0233(10) 0.0196(9) 0.0031(8) 0.0074(8) -0.0025(8) C3 0.0306(11) 0.0275(11) 0.0240(10) 0.0028(8) 0.0112(8) 0.0023(9) C4 0.0369(11) 0.0316(11) 0.0219(10) 0.0040(8) 0.0145(8) 0.0025(9) C5 0.0303(10) 0.0275(10) 0.0229(9) -0.0012(8) 0.0086(8) 0.0041(8) C6 0.0319(11) 0.0247(10) 0.0206(9) 0.0045(8) 0.0054(8) 0.0012(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 Cd1 O3 2.2913(15) 3_767 ? Cd1 O3 2.2913(15) . ? Cd1 O1 2.3003(13) 2_746 ? Cd1 O1 2.3004(13) 4_576 ? Cd1 N1 2.3680(16) 3_767 ? Cd1 N1 2.3680(16) . ? Cl1 C5 1.733(2) . ? O1 C1 1.267(2) . ? O1 Cd1 2.3003(13) 2_756 ? O2 C1 1.237(2) . ? O3 H3A 0.8501 . ? O3 H3B 0.8501 . ? N1 C4 1.335(3) . ? N1 C3 1.341(2) . ? C1 C2 1.512(3) . ? C2 C6 1.381(3) . ? C2 C3 1.387(3) . ? C3 H3 0.9300 . ? C4 C5 1.378(3) . ? C4 H4 0.9300 . ? C5 C6 1.382(3) . ? C6 H6 0.9300 . ? 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 Cd1 O3 180.00(5) 3_767 . ? O3 Cd1 O1 90.96(5) 3_767 2_746 ? O3 Cd1 O1 89.04(5) . 2_746 ? O3 Cd1 O1 89.04(5) 3_767 4_576 ? O3 Cd1 O1 90.96(5) . 4_576 ? O1 Cd1 O1 180.000(1) 2_746 4_576 ? O3 Cd1 N1 87.11(6) 3_767 3_767 ? O3 Cd1 N1 92.89(6) . 3_767 ? O1 Cd1 N1 92.18(5) 2_746 3_767 ? O1 Cd1 N1 87.82(5) 4_576 3_767 ? O3 Cd1 N1 92.89(6) 3_767 . ? O3 Cd1 N1 87.11(6) . . ? O1 Cd1 N1 87.82(5) 2_746 . ? O1 Cd1 N1 92.18(5) 4_576 . ? N1 Cd1 N1 180.000(1) 3_767 . ? C1 O1 Cd1 124.06(12) . 2_756 ? Cd1 O3 H3A 124.2 . . ? Cd1 O3 H3B 97.0 . . ? H3A O3 H3B 114.4 . . ? C4 N1 C3 117.92(17) . . ? C4 N1 Cd1 123.95(12) . . ? C3 N1 Cd1 118.12(13) . . ? O2 C1 O1 125.84(17) . . ? O2 C1 C2 117.66(18) . . ? O1 C1 C2 116.49(17) . . ? C6 C2 C3 118.59(17) . . ? C6 C2 C1 122.44(17) . . ? C3 C2 C1 118.97(17) . . ? N1 C3 C2 123.22(18) . . ? N1 C3 H3 118.4 . . ? C2 C3 H3 118.4 . . ? N1 C4 C5 121.92(17) . . ? N1 C4 H4 119.0 . . ? C5 C4 H4 119.0 . . ? C4 C5 C6 120.44(18) . . ? C4 C5 Cl1 119.17(14) . . ? C6 C5 Cl1 120.38(15) . . ? C2 C6 C5 117.90(18) . . ? C2 C6 H6 121.1 . . ? C5 C6 H6 121.1 . . ? 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 O3 Cd1 N1 C4 76.45(17) 3_767 . . . ? O3 Cd1 N1 C4 -103.55(17) . . . . ? O1 Cd1 N1 C4 167.31(17) 2_746 . . . ? O1 Cd1 N1 C4 -12.69(17) 4_576 . . . ? O3 Cd1 N1 C3 -104.69(15) 3_767 . . . ? O3 Cd1 N1 C3 75.31(15) . . . . ? O1 Cd1 N1 C3 -13.83(15) 2_746 . . . ? O1 Cd1 N1 C3 166.17(15) 4_576 . . . ? Cd1 O1 C1 O2 -18.4(3) 2_756 . . . ? Cd1 O1 C1 C2 161.36(12) 2_756 . . . ? O2 C1 C2 C6 167.1(2) . . . . ? O1 C1 C2 C6 -12.6(3) . . . . ? O2 C1 C2 C3 -13.0(3) . . . . ? O1 C1 C2 C3 167.25(19) . . . . ? C4 N1 C3 C2 -1.3(3) . . . . ? Cd1 N1 C3 C2 179.79(15) . . . . ? C6 C2 C3 N1 1.7(3) . . . . ? C1 C2 C3 N1 -178.19(19) . . . . ? C3 N1 C4 C5 -0.1(3) . . . . ? Cd1 N1 C4 C5 178.79(15) . . . . ? N1 C4 C5 C6 1.0(3) . . . . ? N1 C4 C5 Cl1 179.68(16) . . . . ? C3 C2 C6 C5 -0.7(3) . . . . ? C1 C2 C6 C5 179.14(18) . . . . ? C4 C5 C6 C2 -0.5(3) . . . . ? Cl1 C5 C6 C2 -179.21(15) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.301 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 942326' ####################################################################### # # 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_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Cd Cl2 N2 O3' _chemical_formula_weight 377.49 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' Cd Cd -0.8075 1.2024 '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 14.1516(6) _cell_length_b 12.6704(6) _cell_length_c 7.0376(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.6150(10) _cell_angle_gamma 90.00 _cell_volume 1259.38(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3634 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 29.71 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.991 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 2.154 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5456 _exptl_absorpt_correction_T_max 0.6486 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 6350 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2233 _reflns_number_gt 2027 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0183P)^2^+0.7175P] 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 2233 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0223 _refine_ls_R_factor_gt 0.0194 _refine_ls_wR_factor_ref 0.0446 _refine_ls_wR_factor_gt 0.0434 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.719897(12) -0.159040(13) 0.15210(2) 0.02245(7) Uani 1 1 d . . . Cl1 Cl 0.70469(7) 0.17415(8) 0.73591(16) 0.0785(3) Uani 1 1 d . . . Cl2 Cl 0.82006(4) -0.20512(5) 0.47039(9) 0.02891(14) Uani 1 1 d . . . O1 O 0.37380(12) 0.09604(15) 0.1102(3) 0.0343(4) Uani 1 1 d . . . O2 O 0.40077(13) 0.23664(15) 0.2981(3) 0.0412(5) Uani 1 1 d . . . O3 O 0.82408(13) -0.02436(15) 0.0902(3) 0.0365(4) Uani 1 1 d . . . N1 N 0.63920(14) -0.02337(16) 0.3143(3) 0.0267(5) Uani 1 1 d . . . N2 N 0.91037(16) 0.06012(18) -0.1225(3) 0.0380(6) Uani 1 1 d . . . C1 C 0.42002(17) 0.1472(2) 0.2348(4) 0.0259(6) Uani 1 1 d . . . C2 C 0.51239(17) 0.10238(19) 0.3202(3) 0.0246(5) Uani 1 1 d . . . C3 C 0.55940(19) 0.1523(2) 0.4724(4) 0.0324(6) Uani 1 1 d . . . H3 H 0.5335 0.2119 0.5261 0.039 Uiso 1 1 calc R . . C4 C 0.64454(19) 0.1134(2) 0.5437(4) 0.0347(6) Uani 1 1 d . . . C5 C 0.68332(18) 0.0262(2) 0.4609(4) 0.0326(6) Uani 1 1 d . . . H5 H 0.7419 0.0014 0.5090 0.039 Uiso 1 1 calc R . . C6 C 0.55472(17) 0.01345(19) 0.2471(4) 0.0263(5) Uani 1 1 d . . . H6 H 0.5229 -0.0222 0.1468 0.032 Uiso 1 1 calc R . . C7 C 0.85810(18) -0.0183(2) -0.0673(4) 0.0338(6) Uani 1 1 d . . . H7 H 0.8457 -0.0734 -0.1526 0.041 Uiso 1 1 calc R . . C8 C 0.9266(2) 0.1526(2) -0.0035(6) 0.0567(9) Uani 1 1 d . . . H8A H 0.8840 0.2078 -0.0467 0.085 Uiso 1 1 calc R . . H8B H 0.9907 0.1760 -0.0111 0.085 Uiso 1 1 calc R . . H8C H 0.9157 0.1351 0.1260 0.085 Uiso 1 1 calc R . . C9 C 0.9464(2) 0.0610(3) -0.3116(5) 0.0587(10) Uani 1 1 d . . . H9A H 0.9331 -0.0055 -0.3729 0.088 Uiso 1 1 calc R . . H9B H 1.0136 0.0725 -0.3011 0.088 Uiso 1 1 calc R . . H9C H 0.9164 0.1167 -0.3856 0.088 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 Cd1 0.01919(11) 0.02215(11) 0.02588(11) 0.00061(7) 0.00041(7) -0.00063(7) Cl1 0.0596(5) 0.0825(7) 0.0873(7) -0.0551(6) -0.0433(5) 0.0320(5) Cl2 0.0275(3) 0.0304(3) 0.0283(3) 0.0049(3) -0.0026(3) -0.0024(3) O1 0.0306(10) 0.0386(11) 0.0324(10) 0.0005(9) -0.0077(8) 0.0070(9) O2 0.0315(10) 0.0374(11) 0.0537(13) -0.0091(10) -0.0040(9) 0.0157(9) O3 0.0355(11) 0.0351(11) 0.0393(11) 0.0012(9) 0.0051(9) -0.0105(9) N1 0.0246(11) 0.0267(11) 0.0283(11) 0.0001(9) -0.0006(9) 0.0060(9) N2 0.0319(13) 0.0335(13) 0.0489(15) 0.0070(11) 0.0058(11) -0.0035(11) C1 0.0233(13) 0.0301(15) 0.0249(13) 0.0052(11) 0.0060(11) 0.0046(11) C2 0.0232(13) 0.0255(13) 0.0251(13) 0.0028(10) 0.0010(10) 0.0028(11) C3 0.0317(15) 0.0301(15) 0.0352(15) -0.0065(12) 0.0015(12) 0.0094(12) C4 0.0286(14) 0.0372(15) 0.0372(16) -0.0097(13) -0.0080(12) 0.0049(12) C5 0.0244(13) 0.0331(15) 0.0394(16) -0.0034(12) -0.0056(12) 0.0067(12) C6 0.0257(13) 0.0279(13) 0.0250(13) 0.0018(11) 0.0002(10) 0.0033(11) C7 0.0268(14) 0.0311(15) 0.0429(17) 0.0059(12) -0.0026(12) -0.0001(12) C8 0.049(2) 0.0382(18) 0.082(3) 0.0010(17) -0.0014(19) -0.0103(15) C9 0.048(2) 0.070(2) 0.059(2) 0.0205(18) 0.0137(17) -0.0086(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O2 2.2049(17) 2_645 ? Cd1 O3 2.3144(17) . ? Cd1 O1 2.3439(17) 3_655 ? Cd1 N1 2.393(2) . ? Cd1 Cl2 2.6145(6) 4 ? Cd1 Cl2 2.6396(6) . ? Cl1 C4 1.733(3) . ? Cl2 Cd1 2.6145(6) 4_556 ? O1 C1 1.243(3) . ? O1 Cd1 2.3439(17) 3_655 ? O2 C1 1.253(3) . ? O2 Cd1 2.2049(17) 2_655 ? O3 C7 1.238(3) . ? N1 C5 1.329(3) . ? N1 C6 1.342(3) . ? N2 C7 1.313(3) . ? N2 C8 1.450(4) . ? N2 C9 1.455(4) . ? C1 C2 1.514(3) . ? C2 C3 1.379(4) . ? C2 C6 1.390(3) . ? C3 C4 1.367(4) . ? C3 H3 0.9300 . ? C4 C5 1.379(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? 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 Cd1 O3 168.78(7) 2_645 . ? O2 Cd1 O1 85.65(7) 2_645 3_655 ? O3 Cd1 O1 86.34(7) . 3_655 ? O2 Cd1 N1 87.54(7) 2_645 . ? O3 Cd1 N1 83.62(7) . . ? O1 Cd1 N1 82.40(7) 3_655 . ? O2 Cd1 Cl2 97.61(6) 2_645 4 ? O3 Cd1 Cl2 91.26(5) . 4 ? O1 Cd1 Cl2 97.83(5) 3_655 4 ? N1 Cd1 Cl2 174.85(5) . 4 ? O2 Cd1 Cl2 96.45(5) 2_645 . ? O3 Cd1 Cl2 90.48(5) . . ? O1 Cd1 Cl2 172.09(5) 3_655 . ? N1 Cd1 Cl2 90.05(5) . . ? Cl2 Cd1 Cl2 89.470(17) 4 . ? Cd1 Cl2 Cd1 106.38(2) 4_556 . ? C1 O1 Cd1 128.63(16) . 3_655 ? C1 O2 Cd1 141.82(18) . 2_655 ? C7 O3 Cd1 120.14(18) . . ? C5 N1 C6 118.3(2) . . ? C5 N1 Cd1 119.65(16) . . ? C6 N1 Cd1 121.54(17) . . ? C7 N2 C8 120.8(3) . . ? C7 N2 C9 120.9(3) . . ? C8 N2 C9 118.0(3) . . ? O1 C1 O2 127.3(2) . . ? O1 C1 C2 119.1(2) . . ? O2 C1 C2 113.6(2) . . ? C3 C2 C6 117.5(2) . . ? C3 C2 C1 119.9(2) . . ? C6 C2 C1 122.6(2) . . ? C4 C3 C2 119.4(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 119.9(2) . . ? C3 C4 Cl1 120.3(2) . . ? C5 C4 Cl1 119.8(2) . . ? N1 C5 C4 121.8(2) . . ? N1 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? N1 C6 C2 123.2(2) . . ? N1 C6 H6 118.4 . . ? C2 C6 H6 118.4 . . ? O3 C7 N2 124.8(3) . . ? O3 C7 H7 117.6 . . ? N2 C7 H7 117.6 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 Cd1 Cl2 Cd1 -0.54(6) 2_645 . . 4_556 ? O3 Cd1 Cl2 Cd1 170.61(5) . . . 4_556 ? N1 Cd1 Cl2 Cd1 86.99(5) . . . 4_556 ? Cl2 Cd1 Cl2 Cd1 -98.14(3) 4 . . 4_556 ? O2 Cd1 O3 C7 -102.2(4) 2_645 . . . ? O1 Cd1 O3 C7 -57.7(2) 3_655 . . . ? N1 Cd1 O3 C7 -140.5(2) . . . . ? Cl2 Cd1 O3 C7 40.07(19) 4 . . . ? Cl2 Cd1 O3 C7 129.55(19) . . . . ? O2 Cd1 N1 C5 126.1(2) 2_645 . . . ? O3 Cd1 N1 C5 -60.84(19) . . . . ? O1 Cd1 N1 C5 -148.0(2) 3_655 . . . ? Cl2 Cd1 N1 C5 29.64(19) . . . . ? O2 Cd1 N1 C6 -62.37(19) 2_645 . . . ? O3 Cd1 N1 C6 110.71(19) . . . . ? O1 Cd1 N1 C6 23.56(18) 3_655 . . . ? Cl2 Cd1 N1 C6 -158.82(18) . . . . ? Cd1 O1 C1 O2 31.3(4) 3_655 . . . ? Cd1 O1 C1 C2 -146.28(17) 3_655 . . . ? Cd1 O2 C1 O1 29.2(5) 2_655 . . . ? Cd1 O2 C1 C2 -153.1(2) 2_655 . . . ? O1 C1 C2 C3 -173.0(2) . . . . ? O2 C1 C2 C3 9.1(3) . . . . ? O1 C1 C2 C6 9.2(4) . . . . ? O2 C1 C2 C6 -168.7(2) . . . . ? C6 C2 C3 C4 0.3(4) . . . . ? C1 C2 C3 C4 -177.5(2) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C2 C3 C4 Cl1 -179.6(2) . . . . ? C6 N1 C5 C4 -0.1(4) . . . . ? Cd1 N1 C5 C4 171.7(2) . . . . ? C3 C4 C5 N1 -1.3(4) . . . . ? Cl1 C4 C5 N1 179.4(2) . . . . ? C5 N1 C6 C2 1.7(4) . . . . ? Cd1 N1 C6 C2 -169.93(18) . . . . ? C3 C2 C6 N1 -1.8(4) . . . . ? C1 C2 C6 N1 175.9(2) . . . . ? Cd1 O3 C7 N2 173.19(19) . . . . ? C8 N2 C7 O3 -4.9(4) . . . . ? C9 N2 C7 O3 -179.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.330 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 942327' ####################################################################### # # 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_942328 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13.50 H12 Cd Cl2 N2 O5.50' _chemical_formula_weight 473.55 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' Cd Cd -0.8075 1.2024 '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 15.2423(8) _cell_length_b 17.1026(8) _cell_length_c 15.0777(7) _cell_angle_alpha 90.00 _cell_angle_beta 120.3120(10) _cell_angle_gamma 90.00 _cell_volume 3393.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2847 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 27.16 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.854 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1864 _exptl_absorpt_coefficient_mu 1.631 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6581 _exptl_absorpt_correction_T_max 0.7363 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 8614 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3002 _reflns_number_gt 2468 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0376P)^2^+8.0424P] 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 3002 _refine_ls_number_parameters 231 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0786 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.076 _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 Cd1 Cd 0.13541(2) 0.131426(18) 0.78620(2) 0.03095(12) Uani 1 1 d . . . Cl1 Cl 0.36848(9) 0.36433(8) 0.70284(9) 0.0516(3) Uani 1 1 d . . . Cl2 Cl 0.45578(11) -0.10280(11) 0.86020(10) 0.0749(5) Uani 1 1 d . . . O1 O 0.4248(2) 0.28701(18) 1.1340(2) 0.0416(7) Uani 1 1 d . . . O2 O 0.5550(2) 0.32940(19) 1.1192(2) 0.0411(7) Uani 1 1 d . . . O3 O 0.2196(2) -0.07509(19) 0.4496(2) 0.0439(8) Uani 1 1 d . . . O4 O 0.0979(3) 0.0089(2) 0.4294(2) 0.0512(9) Uani 1 1 d . . . O5 O 0.0000 0.0510(2) 0.7500 0.0335(9) Uani 1 2 d S . . H5A H 0.0246 0.0268 0.8069 0.050 Uiso 1 1 d R . . N1 N 0.2636(3) 0.2216(2) 0.8328(2) 0.0351(8) Uani 1 1 d . . . N2 N 0.2208(3) 0.0408(2) 0.7366(2) 0.0364(8) Uani 1 1 d . . . C1 C 0.4674(3) 0.3026(2) 1.0840(3) 0.0330(9) Uani 1 1 d . . . C2 C 0.4060(3) 0.2876(2) 0.9697(3) 0.0306(9) Uani 1 1 d . . . C3 C 0.4232(3) 0.3271(3) 0.8990(3) 0.0345(10) Uani 1 1 d . . . H3 H 0.4776 0.3614 0.9207 0.041 Uiso 1 1 calc R . . C4 C 0.3576(3) 0.3138(3) 0.7964(3) 0.0361(10) Uani 1 1 d . . . C5 C 0.2791(3) 0.2605(3) 0.7658(3) 0.0370(10) Uani 1 1 d . . . H5 H 0.2359 0.2516 0.6960 0.044 Uiso 1 1 calc R . . C6 C 0.3257(3) 0.2355(3) 0.9337(3) 0.0335(9) Uani 1 1 d . . . H6 H 0.3142 0.2091 0.9809 0.040 Uiso 1 1 calc R . . C7 C 0.1777(3) -0.0298(3) 0.4823(3) 0.0339(10) Uani 1 1 d . . . C8 C 0.2276(3) -0.0207(3) 0.5976(3) 0.0332(9) Uani 1 1 d . . . C9 C 0.1839(3) 0.0300(3) 0.6367(3) 0.0360(10) Uani 1 1 d . . . H9 H 0.1260 0.0576 0.5906 0.043 Uiso 1 1 calc R . . C10 C 0.3033(3) 0.0006(3) 0.8028(3) 0.0407(11) Uani 1 1 d . . . H10 H 0.3297 0.0075 0.8730 0.049 Uiso 1 1 calc R . . C11 C 0.3502(3) -0.0511(3) 0.7695(3) 0.0410(11) Uani 1 1 d . . . C12 C 0.3126(3) -0.0630(3) 0.6663(3) 0.0394(10) Uani 1 1 d . . . H12 H 0.3434 -0.0982 0.6433 0.047 Uiso 1 1 calc R . . O6 O 0.5438(8) 0.1400(6) 0.7701(10) 0.199(5) Uani 0.75 1 d PDU . 1 C13 C 0.5512(11) 0.1333(10) 0.8625(12) 0.150(6) Uani 0.75 1 d PDU . 1 C14 C 0.6347(11) 0.1736(9) 0.9418(10) 0.159(6) Uani 0.75 1 d PDU A 1 O6' O 0.515(3) 0.114(2) 0.886(2) 0.153(12) Uani 0.25 1 d PU B 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 Cd1 0.02790(18) 0.0402(2) 0.02319(17) -0.00338(13) 0.01172(13) -0.00408(14) Cl1 0.0528(7) 0.0658(8) 0.0374(6) 0.0082(6) 0.0237(6) -0.0123(6) Cl2 0.0606(9) 0.1033(12) 0.0468(7) 0.0184(8) 0.0167(7) 0.0435(9) O1 0.0485(18) 0.0499(19) 0.0307(15) -0.0073(14) 0.0232(15) -0.0030(15) O2 0.0348(17) 0.0505(19) 0.0287(15) -0.0047(14) 0.0091(13) -0.0107(15) O3 0.0436(18) 0.056(2) 0.0295(15) -0.0087(15) 0.0165(14) 0.0048(16) O4 0.055(2) 0.064(2) 0.0238(16) -0.0028(15) 0.0120(15) 0.0150(18) O5 0.032(2) 0.035(2) 0.026(2) 0.000 0.0096(17) 0.000 N1 0.0338(19) 0.043(2) 0.0251(18) -0.0063(16) 0.0127(15) -0.0084(16) N2 0.036(2) 0.045(2) 0.0242(18) -0.0032(16) 0.0117(16) 0.0032(17) C1 0.036(2) 0.029(2) 0.026(2) -0.0036(18) 0.0102(19) 0.0021(19) C2 0.029(2) 0.035(2) 0.027(2) -0.0021(18) 0.0136(18) 0.0037(18) C3 0.031(2) 0.038(2) 0.033(2) -0.0029(19) 0.0148(19) -0.0030(19) C4 0.036(2) 0.044(3) 0.030(2) 0.0015(19) 0.0190(19) -0.001(2) C5 0.033(2) 0.052(3) 0.022(2) -0.0030(19) 0.0111(18) -0.004(2) C6 0.033(2) 0.040(2) 0.027(2) -0.0009(18) 0.0143(19) -0.0008(19) C7 0.036(2) 0.037(2) 0.027(2) -0.0041(19) 0.0146(19) -0.005(2) C8 0.034(2) 0.037(2) 0.026(2) -0.0036(18) 0.0139(19) -0.0034(19) C9 0.034(2) 0.041(3) 0.026(2) 0.0012(19) 0.0107(19) 0.004(2) C10 0.040(3) 0.053(3) 0.028(2) 0.002(2) 0.016(2) 0.005(2) C11 0.033(2) 0.051(3) 0.032(2) 0.009(2) 0.012(2) 0.011(2) C12 0.037(2) 0.044(3) 0.037(2) -0.002(2) 0.018(2) 0.004(2) O6 0.196(10) 0.189(8) 0.224(9) -0.012(8) 0.114(8) -0.014(6) C13 0.137(9) 0.145(10) 0.168(10) 0.005(8) 0.077(8) 0.016(7) C14 0.157(9) 0.168(10) 0.149(9) 0.004(7) 0.075(7) 0.007(8) O6' 0.177(15) 0.165(15) 0.140(14) 0.005(9) 0.098(10) -0.010(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O2 2.275(3) 8_455 ? Cd1 N1 2.303(3) . ? Cd1 O5 2.305(2) . ? Cd1 O1 2.313(3) 7_557 ? Cd1 O3 2.335(3) 6_556 ? Cd1 N2 2.375(3) . ? Cl1 C4 1.732(4) . ? Cl2 C11 1.738(4) . ? O1 C1 1.247(5) . ? O1 Cd1 2.313(3) 7_557 ? O2 C1 1.249(5) . ? O2 Cd1 2.275(3) 8_556 ? O3 C7 1.252(5) . ? O3 Cd1 2.335(3) 6 ? O4 C7 1.255(5) . ? O5 Cd1 2.305(2) 2_556 ? O5 H5A 0.8500 . ? N1 C5 1.327(5) . ? N1 C6 1.347(5) . ? N2 C9 1.329(5) . ? N2 C10 1.335(5) . ? C1 C2 1.511(5) . ? C2 C6 1.384(6) . ? C2 C3 1.395(6) . ? C3 C4 1.372(6) . ? C3 H3 0.9300 . ? C4 C5 1.385(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.513(5) . ? C8 C12 1.386(6) . ? C8 C9 1.392(6) . ? C9 H9 0.9300 . ? C10 C11 1.381(6) . ? C10 H10 0.9300 . ? C11 C12 1.376(6) . ? C12 H12 0.9300 . ? O6 O6 1.15(2) 2_656 ? O6 C13 1.344(9) . ? O6 C13 1.79(2) 2_656 ? C13 C14 1.410(9) . ? C13 O6 1.79(2) 2_656 ? 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 Cd1 N1 92.32(11) 8_455 . ? O2 Cd1 O5 89.77(8) 8_455 . ? N1 Cd1 O5 172.87(11) . . ? O2 Cd1 O1 105.35(11) 8_455 7_557 ? N1 Cd1 O1 86.31(12) . 7_557 ? O5 Cd1 O1 86.57(10) . 7_557 ? O2 Cd1 O3 172.46(11) 8_455 6_556 ? N1 Cd1 O3 91.41(11) . 6_556 ? O5 Cd1 O3 87.31(8) . 6_556 ? O1 Cd1 O3 81.42(11) 7_557 6_556 ? O2 Cd1 N2 85.33(11) 8_455 . ? N1 Cd1 N2 91.02(12) . . ? O5 Cd1 N2 95.94(11) . . ? O1 Cd1 N2 169.07(11) 7_557 . ? O3 Cd1 N2 88.05(11) 6_556 . ? C1 O1 Cd1 130.5(3) . 7_557 ? C1 O2 Cd1 116.2(3) . 8_556 ? C7 O3 Cd1 123.6(3) . 6 ? Cd1 O5 Cd1 106.71(16) 2_556 . ? Cd1 O5 H5A 114.5 2_556 . ? Cd1 O5 H5A 99.5 . . ? C5 N1 C6 118.6(4) . . ? C5 N1 Cd1 123.6(3) . . ? C6 N1 Cd1 117.9(3) . . ? C9 N2 C10 118.5(4) . . ? C9 N2 Cd1 117.5(3) . . ? C10 N2 Cd1 124.0(3) . . ? O1 C1 O2 126.3(4) . . ? O1 C1 C2 116.2(4) . . ? O2 C1 C2 117.5(4) . . ? C6 C2 C3 118.9(4) . . ? C6 C2 C1 118.2(4) . . ? C3 C2 C1 122.8(4) . . ? C4 C3 C2 118.1(4) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? C3 C4 C5 120.0(4) . . ? C3 C4 Cl1 121.4(3) . . ? C5 C4 Cl1 118.6(3) . . ? N1 C5 C4 122.2(4) . . ? N1 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? N1 C6 C2 122.3(4) . . ? N1 C6 H6 118.8 . . ? C2 C6 H6 118.8 . . ? O3 C7 O4 126.8(4) . . ? O3 C7 C8 117.1(4) . . ? O4 C7 C8 116.1(4) . . ? C12 C8 C9 118.4(4) . . ? C12 C8 C7 122.9(4) . . ? C9 C8 C7 118.7(4) . . ? N2 C9 C8 123.2(4) . . ? N2 C9 H9 118.4 . . ? C8 C9 H9 118.4 . . ? N2 C10 C11 121.5(4) . . ? N2 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C12 C11 C10 120.7(4) . . ? C12 C11 Cl2 120.4(4) . . ? C10 C11 Cl2 118.9(3) . . ? C11 C12 C8 117.8(4) . . ? C11 C12 H12 121.1 . . ? C8 C12 H12 121.1 . . ? O6 O6 C13 90.9(18) 2_656 . ? O6 O6 C13 48.8(10) 2_656 2_656 ? C13 O6 C13 138.7(11) . 2_656 ? O6 C13 C14 113.8(10) . . ? C14 C13 O6 142.4(13) . 2_656 ? 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 Cd1 O5 Cd1 -68.28(8) 8_455 . . 2_556 ? O1 Cd1 O5 Cd1 37.11(7) 7_557 . . 2_556 ? O3 Cd1 O5 Cd1 118.68(8) 6_556 . . 2_556 ? N2 Cd1 O5 Cd1 -153.56(8) . . . 2_556 ? O2 Cd1 N1 C5 -13.5(4) 8_455 . . . ? O1 Cd1 N1 C5 -118.8(4) 7_557 . . . ? O3 Cd1 N1 C5 159.9(4) 6_556 . . . ? N2 Cd1 N1 C5 71.9(3) . . . . ? O2 Cd1 N1 C6 166.3(3) 8_455 . . . ? O1 Cd1 N1 C6 61.1(3) 7_557 . . . ? O3 Cd1 N1 C6 -20.2(3) 6_556 . . . ? N2 Cd1 N1 C6 -108.3(3) . . . . ? O2 Cd1 N2 C9 -13.4(3) 8_455 . . . ? N1 Cd1 N2 C9 -105.7(3) . . . . ? O5 Cd1 N2 C9 75.8(3) . . . . ? O1 Cd1 N2 C9 178.6(5) 7_557 . . . ? O3 Cd1 N2 C9 162.9(3) 6_556 . . . ? O2 Cd1 N2 C10 166.4(4) 8_455 . . . ? N1 Cd1 N2 C10 74.1(4) . . . . ? O5 Cd1 N2 C10 -104.3(3) . . . . ? O1 Cd1 N2 C10 -1.6(8) 7_557 . . . ? O3 Cd1 N2 C10 -17.2(4) 6_556 . . . ? Cd1 O1 C1 O2 70.2(6) 7_557 . . . ? Cd1 O1 C1 C2 -109.6(4) 7_557 . . . ? Cd1 O2 C1 O1 -8.9(6) 8_556 . . . ? Cd1 O2 C1 C2 170.9(3) 8_556 . . . ? O1 C1 C2 C6 -21.4(5) . . . . ? O2 C1 C2 C6 158.8(4) . . . . ? O1 C1 C2 C3 155.0(4) . . . . ? O2 C1 C2 C3 -24.8(6) . . . . ? C6 C2 C3 C4 1.8(6) . . . . ? C1 C2 C3 C4 -174.6(4) . . . . ? C2 C3 C4 C5 -2.2(6) . . . . ? C2 C3 C4 Cl1 176.2(3) . . . . ? C6 N1 C5 C4 0.8(7) . . . . ? Cd1 N1 C5 C4 -179.4(3) . . . . ? C3 C4 C5 N1 0.9(7) . . . . ? Cl1 C4 C5 N1 -177.5(3) . . . . ? C5 N1 C6 C2 -1.2(6) . . . . ? Cd1 N1 C6 C2 178.9(3) . . . . ? C3 C2 C6 N1 -0.1(6) . . . . ? C1 C2 C6 N1 176.5(4) . . . . ? Cd1 O3 C7 O4 -20.7(6) 6 . . . ? Cd1 O3 C7 C8 159.0(3) 6 . . . ? O3 C7 C8 C12 -3.5(6) . . . . ? O4 C7 C8 C12 176.2(4) . . . . ? O3 C7 C8 C9 179.1(4) . . . . ? O4 C7 C8 C9 -1.2(6) . . . . ? C10 N2 C9 C8 -0.7(7) . . . . ? Cd1 N2 C9 C8 179.2(3) . . . . ? C12 C8 C9 N2 1.2(7) . . . . ? C7 C8 C9 N2 178.7(4) . . . . ? C9 N2 C10 C11 0.2(7) . . . . ? Cd1 N2 C10 C11 -179.6(3) . . . . ? N2 C10 C11 C12 -0.3(7) . . . . ? N2 C10 C11 Cl2 -178.8(3) . . . . ? C10 C11 C12 C8 0.8(7) . . . . ? Cl2 C11 C12 C8 179.3(4) . . . . ? C9 C8 C12 C11 -1.2(6) . . . . ? C7 C8 C12 C11 -178.6(4) . . . . ? O6 O6 C13 C14 -144.9(14) 2_656 . . . ? C13 O6 C13 C14 -156.2(14) 2_656 . . . ? C13 O6 C13 O6 -11(2) 2_656 . . 2_656 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.786 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 942328'