# 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 Cl2 N2 Ni O2 S2 Se' _chemical_formula_sum 'C10 H16 Cl2 N2 Ni O2 S2 Se' _chemical_formula_weight 468.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.5377(11) _cell_length_b 13.1086(17) _cell_length_c 14.4617(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1618.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 753 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 32.63 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.924 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 4.036 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.3773 _exptl_absorpt_correction_T_max 0.7938 _exptl_absorpt_process_details SADABS _exptl_special_details ; A crystal of suitable size and quality was chosen, mounted in Paratone oil on a MiTeGen polymer loop, and placed in the cold stream of the diffractometer. Data were collected on a Bruker Apex2 instrument with MoK(alpha) radiaiton using 0.5 degree omega and phi scans to ensure complete coverage. Unit cell parameters were determined from at least 50 frames. Data were corrected by SADABS 2008.4 program. The structure was solved in the orthorhombic space group P2(1) 2(1) 2(1). ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14668 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0594 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 33.98 _reflns_number_total 6049 _reflns_number_gt 5264 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WINGX (Farrugia, 1999)' _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.011(6) _refine_ls_number_reflns 6049 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0524 _refine_ls_wR_factor_gt 0.0496 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_restrained_S_all 0.901 _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 Se1 Se 0.06068(2) 0.888802(14) 0.751766(17) 0.01137(5) Uani 1 1 d . . . Ni1 Ni -0.00659(3) 1.137631(17) 0.75848(2) 0.00770(6) Uani 1 1 d . . . Cl1 Cl -0.18364(7) 1.19458(4) 0.64008(4) 0.01082(10) Uani 1 1 d . . . Cl2 Cl 0.16125(7) 1.08157(4) 0.88001(4) 0.01219(11) Uani 1 1 d . . . O3 O -0.1877(2) 1.17111(10) 0.85035(10) 0.0116(3) Uani 1 1 d . . . O5 O 0.1643(2) 1.09919(10) 0.66368(10) 0.0114(3) Uani 1 1 d . . . N8 N -0.0867(2) 0.98535(11) 0.74409(13) 0.0095(3) Uani 1 1 d . . . N10 N -0.0790(2) 0.78896(12) 0.73565(12) 0.0091(4) Uani 1 1 d . . . C18 C -0.2258(3) 0.94066(14) 0.73439(14) 0.0090(4) Uani 1 1 d . . . C19 C -0.2217(3) 0.83007(14) 0.72934(13) 0.0082(4) Uani 1 1 d . . . C20 C -0.3721(3) 0.99296(14) 0.73259(15) 0.0118(4) Uani 1 1 d . . . H20 H -0.3760 1.0638 0.7357 0.014 Uiso 1 1 calc R . . C28 C -0.5013(3) 0.82765(16) 0.72031(15) 0.0136(4) Uani 1 1 d . . . H28 H -0.5951 0.7919 0.7156 0.016 Uiso 1 1 calc R . . C29 C -0.3647(3) 0.77529(15) 0.72141(15) 0.0112(4) Uani 1 1 d . . . H29 H -0.3644 0.7045 0.7170 0.013 Uiso 1 1 calc R . . C30 C -0.5051(3) 0.93753(15) 0.72626(15) 0.0135(4) Uani 1 1 d . . . H30 H -0.6012 0.9709 0.7257 0.016 Uiso 1 1 calc R . . S2 S 0.19998(7) 1.16781(4) 0.58038(4) 0.01007(11) Uani 1 1 d . . . S1 S -0.19215(8) 1.14589(4) 0.95362(4) 0.01371(11) Uani 1 1 d . . . C43 C 0.1028(3) 1.11140(17) 0.48441(16) 0.0156(5) Uani 1 1 d . . . H43A H 0.1322 1.0409 0.4798 0.023 Uiso 1 1 calc R . . H43B H 0.1323 1.1464 0.4288 0.023 Uiso 1 1 calc R . . H43C H -0.0084 1.1165 0.4929 0.023 Uiso 1 1 calc R . . C42 C 0.3955(3) 1.13455(16) 0.55055(16) 0.0146(5) Uani 1 1 d . . . H42A H 0.4656 1.1585 0.5977 0.022 Uiso 1 1 calc R . . H42B H 0.4224 1.1655 0.4925 0.022 Uiso 1 1 calc R . . H42C H 0.4039 1.0617 0.5454 0.022 Uiso 1 1 calc R . . C41 C -0.3859(3) 1.18114(18) 0.98528(18) 0.0221(6) Uani 1 1 d . . . H41A H -0.3944 1.2542 0.9861 0.033 Uiso 1 1 calc R . . H41B H -0.4092 1.1547 1.0456 0.033 Uiso 1 1 calc R . . H41C H -0.4586 1.1537 0.9412 0.033 Uiso 1 1 calc R . . C50 C -0.2151(3) 1.01133(15) 0.96207(17) 0.0175(5) Uani 1 1 d . . . H50A H -0.3018 0.9901 0.9244 0.026 Uiso 1 1 calc R . . H50B H -0.2346 0.9930 1.0253 0.026 Uiso 1 1 calc R . . H50C H -0.1213 0.9783 0.9410 0.026 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 Se1 0.00611(10) 0.00700(8) 0.02102(11) -0.00026(9) -0.00117(10) 0.00013(7) Ni1 0.00701(13) 0.00641(10) 0.00968(12) 0.00049(9) 0.00008(11) 0.00028(9) Cl1 0.0098(3) 0.0108(2) 0.0119(2) 0.00178(17) -0.0014(2) 0.0000(2) Cl2 0.0104(3) 0.0123(2) 0.0139(2) 0.00317(18) -0.0031(2) 0.0000(2) O3 0.0105(9) 0.0135(7) 0.0108(7) 0.0015(6) 0.0032(6) 0.0028(7) O5 0.0115(9) 0.0098(7) 0.0129(7) 0.0025(5) 0.0040(6) 0.0002(6) N8 0.0068(9) 0.0072(7) 0.0145(9) 0.0006(7) 0.0006(8) 0.0016(6) N10 0.0068(9) 0.0092(7) 0.0114(9) -0.0005(6) 0.0003(7) -0.0012(6) C18 0.0085(11) 0.0091(8) 0.0094(10) 0.0017(7) -0.0005(8) -0.0018(7) C19 0.0094(11) 0.0074(8) 0.0076(9) 0.0011(7) 0.0011(7) 0.0005(7) C20 0.0112(12) 0.0092(8) 0.0151(11) 0.0009(7) 0.0017(9) 0.0021(8) C28 0.0072(12) 0.0161(10) 0.0177(10) 0.0010(8) -0.0003(9) -0.0028(9) C29 0.0099(12) 0.0094(9) 0.0143(10) 0.0000(7) -0.0005(9) -0.0006(8) C30 0.0075(12) 0.0139(10) 0.0190(11) 0.0013(7) 0.0010(9) 0.0028(8) S2 0.0095(3) 0.0102(2) 0.0105(2) 0.00040(18) 0.0010(2) -0.0003(2) S1 0.0108(3) 0.0197(3) 0.0106(2) -0.0016(2) -0.0001(2) -0.0012(2) C43 0.0119(12) 0.0194(10) 0.0157(11) -0.0053(9) 0.0006(9) -0.0031(10) C42 0.0087(12) 0.0201(11) 0.0151(11) 0.0004(8) 0.0018(9) -0.0017(9) C41 0.0196(15) 0.0301(13) 0.0166(12) -0.0033(10) 0.0075(11) 0.0035(11) C50 0.0157(14) 0.0215(11) 0.0154(11) 0.0072(9) 0.0013(10) -0.0015(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 Se1 N10 1.7857(17) . ? Se1 N8 1.7883(16) . ? Ni1 O5 2.0646(16) . ? Ni1 O3 2.0853(17) . ? Ni1 N10 2.1157(16) 3_556 ? Ni1 N8 2.1204(16) . ? Ni1 Cl2 2.3839(6) . ? Ni1 Cl1 2.4028(7) . ? O3 S1 1.5300(16) . ? O5 S2 1.5341(15) . ? N8 C18 1.332(3) . ? N10 C19 1.336(3) . ? N10 Ni1 2.1157(16) 3_546 ? C18 C20 1.425(3) . ? C18 C19 1.452(2) . ? C19 C29 1.421(3) . ? C20 C30 1.351(3) . ? C20 H20 0.9300 . ? C28 C29 1.353(3) . ? C28 C30 1.443(3) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? S2 C43 1.778(2) . ? S2 C42 1.778(2) . ? S1 C41 1.777(3) . ? S1 C50 1.779(2) . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 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 N10 Se1 N8 92.33(8) . . ? O5 Ni1 O3 176.84(7) . . ? O5 Ni1 N10 90.66(6) . 3_556 ? O3 Ni1 N10 91.89(6) . 3_556 ? O5 Ni1 N8 86.17(6) . . ? O3 Ni1 N8 91.23(6) . . ? N10 Ni1 N8 176.43(7) 3_556 . ? O5 Ni1 Cl2 89.40(5) . . ? O3 Ni1 Cl2 92.34(5) . . ? N10 Ni1 Cl2 92.98(5) 3_556 . ? N8 Ni1 Cl2 88.63(5) . . ? O5 Ni1 Cl1 92.71(5) . . ? O3 Ni1 Cl1 85.54(5) . . ? N10 Ni1 Cl1 87.39(5) 3_556 . ? N8 Ni1 Cl1 91.12(5) . . ? Cl2 Ni1 Cl1 177.86(2) . . ? S1 O3 Ni1 126.51(10) . . ? S2 O5 Ni1 121.24(9) . . ? C18 N8 Se1 108.83(12) . . ? C18 N8 Ni1 135.42(13) . . ? Se1 N8 Ni1 115.66(9) . . ? C19 N10 Se1 108.81(12) . . ? C19 N10 Ni1 134.11(13) . 3_546 ? Se1 N10 Ni1 116.84(9) . 3_546 ? N8 C18 C20 124.88(17) . . ? N8 C18 C19 115.03(19) . . ? C20 C18 C19 120.0(2) . . ? N10 C19 C29 125.84(17) . . ? N10 C19 C18 114.92(19) . . ? C29 C19 C18 119.2(2) . . ? C30 C20 C18 118.63(18) . . ? C30 C20 H20 120.7 . . ? C18 C20 H20 120.7 . . ? C29 C28 C30 121.7(2) . . ? C29 C28 H28 119.2 . . ? C30 C28 H28 119.2 . . ? C28 C29 C19 119.01(18) . . ? C28 C29 H29 120.5 . . ? C19 C29 H29 120.5 . . ? C20 C30 C28 121.4(2) . . ? C20 C30 H30 119.3 . . ? C28 C30 H30 119.3 . . ? O5 S2 C43 106.05(10) . . ? O5 S2 C42 103.47(10) . . ? C43 S2 C42 98.42(11) . . ? O3 S1 C41 102.62(11) . . ? O3 S1 C50 106.50(10) . . ? C41 S1 C50 97.90(12) . . ? S2 C43 H43A 109.5 . . ? S2 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? S2 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? S2 C42 H42A 109.5 . . ? S2 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? S2 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? S1 C41 H41A 109.5 . . ? S1 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? S1 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? S1 C50 H50A 109.5 . . ? S1 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? S1 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.569 _refine_diff_density_min -0.597 _refine_diff_density_rms 0.103 _iucr_refine_instructions_details ; TITL ll02 in P2(1)2(1)2(1) CELL 0.71073 8.5377 13.1086 14.4617 90.000 90.000 90.000 ZERR 6.00 0.0011 0.0017 0.0018 0.000 0.000 0.000 LATT -1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H N CL NI SE O S UNIT 40 64 8 8 4 4 8 8 TEMP 100.00 SIZE 0.060 0.060 0.300 L.S. 4 BOND FMAP 2 PLAN 20 WGHT 0.100000 FVAR 0.11597 SE1 6 0.939373 0.111207 0.248262 11.00000 0.00616 0.00677 = 0.02122 -0.00026 -0.00131 0.00023 NI1 5 1.006621 -0.137624 0.241504 11.00000 0.00653 0.00607 = 0.00947 0.00050 -0.00012 0.00034 CL1 4 1.183713 -0.194591 0.359916 11.00000 0.01028 0.01102 = 0.01163 0.00183 -0.00150 0.00017 CL2 4 0.838700 -0.081536 0.120018 11.00000 0.01041 0.01208 = 0.01404 0.00270 -0.00326 0.00013 O3 7 1.187243 -0.171305 0.149608 11.00000 0.01023 0.01456 = 0.00923 0.00097 0.00226 0.00357 O5 7 0.835704 -0.098905 0.336244 11.00000 0.01327 0.01128 = 0.01246 0.00224 0.00555 0.00105 N8 3 1.086746 0.014451 0.256035 11.00000 0.00663 0.00747 = 0.01472 0.00050 0.00007 0.00141 N10 3 1.078689 0.211080 0.264409 11.00000 0.00564 0.00888 = 0.01321 0.00012 -0.00032 -0.00003 C18 1 1.225134 0.059826 0.265347 11.00000 0.00979 0.00854 = 0.01195 0.00271 -0.00147 -0.00179 C19 1 1.221621 0.169958 0.270975 11.00000 0.01175 0.00453 = 0.00965 0.00178 0.00089 0.00049 C20 1 1.372160 0.006298 0.266963 11.00000 0.00968 0.00997 = 0.01769 0.00069 0.00141 0.00250 AFIX 43 H20A 2 1.375745 -0.064505 0.263485 11.00000 -1.20000 AFIX 0 C28 1 1.501597 0.171999 0.279515 11.00000 0.00910 0.01630 = 0.01768 0.00026 -0.00021 -0.00299 AFIX 43 H28A 2 1.595588 0.207571 0.283612 11.00000 -1.20000 AFIX 0 C29 1 1.365034 0.225291 0.279194 11.00000 0.00823 0.00887 = 0.01565 0.00036 -0.00121 -0.00129 AFIX 43 H29A 2 1.364989 0.296022 0.284200 11.00000 -1.20000 AFIX 0 C30 1 1.505785 0.062273 0.273726 11.00000 0.00631 0.01147 = 0.01992 0.00215 0.00069 0.00199 AFIX 43 H30A 2 1.601989 0.029012 0.274636 11.00000 -1.20000 AFIX 0 S2 8 0.800158 -0.167687 0.419644 11.00000 0.00987 0.01023 = 0.01083 0.00027 0.00083 -0.00038 S1 8 1.192134 -0.145874 0.046395 11.00000 0.01081 0.01964 = 0.01064 -0.00153 -0.00019 -0.00139 C43 1 0.896754 -0.111114 0.515767 11.00000 0.01210 0.02115 = 0.01558 -0.00639 0.00058 -0.00182 AFIX 33 H43A 2 1.007551 -0.122250 0.510653 11.00000 -1.50000 H43B 2 0.858982 -0.141393 0.571946 11.00000 -1.50000 H43C 2 0.875875 -0.039159 0.516593 11.00000 -1.50000 AFIX 0 C42 1 0.604443 -0.134113 0.449498 11.00000 0.01021 0.01853 = 0.01715 0.00034 0.00347 -0.00218 AFIX 33 H42A 2 0.533953 -0.159512 0.403187 11.00000 -1.50000 H42B 2 0.595544 -0.061216 0.453088 11.00000 -1.50000 H42C 2 0.578342 -0.163514 0.508311 11.00000 -1.50000 AFIX 0 C41 1 1.386333 -0.180840 0.013932 11.00000 0.01800 0.03321 = 0.01841 -0.00385 0.00734 0.00226 AFIX 33 H41A 2 1.395698 -0.253820 0.014000 11.00000 -1.50000 H41B 2 1.459502 -0.152311 0.057199 11.00000 -1.50000 H41C 2 1.408353 -0.155214 -0.046879 11.00000 -1.50000 AFIX 0 C50 1 1.215084 -0.011105 0.039115 11.00000 0.01761 0.01805 = 0.01787 0.00709 0.00181 -0.00194 AFIX 33 H50A 2 1.117910 0.021537 0.054607 11.00000 -1.50000 H50B 2 1.244744 0.007292 -0.022707 11.00000 -1.50000 H50C 2 1.294972 0.010516 0.081520 11.00000 -1.50000 HKLF 4 REM ll02 in P2(1)2(1)2(1) REM R1 = 0.0584 for 5264 Fo > 4sig(Fo) and 0.0675 for all 6049 data REM 181 parameters refined using 0 restraints END WGHT 0.0461 12.3469 REM Highest difference peak 1.748, deepest hole -0.830, 1-sigma level 0.137 Q1 1 1.0214 0.0736 0.2319 11.00000 0.05 0.66 Q2 1 1.2046 0.1205 0.2653 11.00000 0.05 0.62 Q3 1 0.9755 0.1782 0.2628 11.00000 0.05 0.61 Q4 1 0.9609 0.0478 0.2354 11.00000 0.05 0.56 Q5 1 1.3196 0.1927 0.2885 11.00000 0.05 0.55 Q6 1 0.8429 0.1020 0.2588 11.00000 0.05 0.51 Q7 1 0.7587 -0.1140 0.3815 11.00000 0.05 0.50 Q8 1 0.8585 -0.1154 0.3904 11.00000 0.05 0.50 Q9 1 1.1182 -0.0546 0.1160 11.00000 0.05 0.50 Q10 1 0.9837 0.2395 0.2601 11.00000 0.05 0.49 Q11 1 1.0138 -0.1920 0.2357 11.00000 0.05 0.49 Q12 1 1.2814 -0.1804 0.0095 11.00000 0.05 0.49 Q13 1 0.7857 -0.0992 0.4176 11.00000 0.05 0.49 Q14 1 1.2703 0.1180 0.2677 11.00000 0.05 0.48 Q15 1 1.2691 -0.1565 0.3393 11.00000 0.05 0.48 Q16 1 1.0776 -0.1848 0.3318 11.00000 0.05 0.48 Q17 1 1.2415 0.2163 0.2662 11.00000 0.05 0.48 Q18 1 1.2849 -0.1404 0.0375 11.00000 0.05 0.48 Q19 1 1.1734 -0.2167 0.0375 11.00000 0.05 0.46 Q20 1 1.1605 -0.2555 0.4119 11.00000 0.05 0.45 ; _database_code_depnum_ccdc_archive 'CCDC 932441' ####################################################################### # # 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_llco_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 Cl2 Co N2 O2 S2 Se' _chemical_formula_weight 469.16 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' S S 0.1246 0.1234 '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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _space_group_name_H-M_alt 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.5078(8) _cell_length_b 13.3811(12) _cell_length_c 14.3894(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1638.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6035 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 32.83 _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.902 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 3.851 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.2168 _exptl_absorpt_correction_T_max 0.8019 _exptl_absorpt_process_details SADABS _exptl_special_details ; A crystal of suitable size and quality was chosen, mounted in Paratone oil on a MiTeGen polymer loop, and placed in the cold stream of the diffractometer. Data were collected on a Bruker Apex2 instrument with MoK(alpha) radiaiton using 0.5 degree omega and phi scans to ensure complete coverage. Unit cell parameters were determined from at least 50 frames. Data were corrected by SADABS 2008.4 program. The structure was solved in the orthorhombic space group P 21 21 21. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21854 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 32.84 _reflns_number_total 6035 _reflns_number_gt 5458 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0089P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.000(6) _refine_ls_number_reflns 6035 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0264 _refine_ls_R_factor_gt 0.0206 _refine_ls_wR_factor_ref 0.0380 _refine_ls_wR_factor_gt 0.0369 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.004 _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 Co1 Co 0.49292(2) 1.137559(13) 0.760099(16) 0.00822(4) Uani 1 1 d . . . Se1 Se 0.558168(18) 0.888543(10) 0.758390(12) 0.01134(4) Uani 1 1 d . . . Cl1 Cl 0.66543(5) 1.08242(3) 0.88317(3) 0.01332(8) Uani 1 1 d . . . Cl2 Cl 0.30956(5) 1.19448(3) 0.64129(3) 0.01135(7) Uani 1 1 d . . . S1 S 0.69831(5) 1.16793(3) 0.57910(3) 0.01082(8) Uani 1 1 d . . . S2 S 0.30365(5) 1.14522(3) 0.95883(3) 0.01441(8) Uani 1 1 d . . . O1 O 0.66126(14) 1.09933(7) 0.66195(8) 0.0125(2) Uani 1 1 d . . . O2 O 0.31435(15) 1.17254(7) 0.85590(8) 0.0128(2) Uani 1 1 d . . . N1 N 0.41116(14) 0.98375(8) 0.74857(10) 0.0104(3) Uani 1 1 d . . . N2 N 0.41885(14) 0.79080(8) 0.73874(10) 0.0097(3) Uani 1 1 d . . . C1 C 0.27174(17) 0.94001(9) 0.73573(11) 0.0087(3) Uani 1 1 d . . . C2 C 0.27578(17) 0.83145(10) 0.73024(11) 0.0089(3) Uani 1 1 d . . . C3 C 0.12499(19) 0.99100(10) 0.73230(12) 0.0121(3) Uani 1 1 d . . . H3 H 0.122(2) 1.0654(11) 0.7369(12) 0.012(4) Uiso 1 1 d . . . C4 C 0.1321(2) 0.77745(11) 0.71956(12) 0.0117(3) Uani 1 1 d . . . H4 H 0.136(2) 0.7062(13) 0.7121(13) 0.017(5) Uiso 1 1 d . . . C5 C -0.0090(2) 0.93624(11) 0.72298(12) 0.0140(3) Uani 1 1 d . . . H5 H -0.1070(19) 0.9697(11) 0.7193(12) 0.006(4) Uiso 1 1 d . . . C6 C -0.0048(2) 0.82905(11) 0.71646(12) 0.0136(3) Uani 1 1 d . . . H6A H -0.106(2) 0.7940(13) 0.7097(14) 0.023(5) Uiso 1 1 d . . . C7 C 0.8948(2) 1.13444(12) 0.54866(13) 0.0146(3) Uani 1 1 d . . . H7C H 0.918(2) 1.1663(13) 0.4925(13) 0.013(5) Uiso 1 1 d . . . H7B H 0.897(2) 1.0605(14) 0.5434(14) 0.029(6) Uiso 1 1 d . . . H7A H 0.961(3) 1.1546(14) 0.5950(16) 0.030(6) Uiso 1 1 d . . . C8 C 0.6000(2) 1.11388(13) 0.48183(12) 0.0153(3) Uani 1 1 d . . . H8C H 0.633(2) 1.0404(12) 0.4798(12) 0.008(4) Uiso 1 1 d . . . H8B H 0.492(2) 1.1242(13) 0.4929(15) 0.025(6) Uiso 1 1 d . . . H8A H 0.631(2) 1.1519(13) 0.4276(14) 0.025(5) Uiso 1 1 d . . . C9 C 0.2813(2) 1.01234(13) 0.96449(14) 0.0183(4) Uani 1 1 d . . . H9C H 0.192(2) 0.9919(12) 0.9270(14) 0.021(5) Uiso 1 1 d . . . H9B H 0.381(3) 0.9852(14) 0.9483(16) 0.036(6) Uiso 1 1 d . . . H9A H 0.265(3) 0.9952(14) 1.0299(15) 0.031(6) Uiso 1 1 d . . . C10 C 0.1063(2) 1.17815(15) 0.98831(15) 0.0223(4) Uani 1 1 d . . . H10C H 0.103(2) 1.2490(16) 0.9904(16) 0.028(6) Uiso 1 1 d . . . H10B H 0.085(3) 1.1503(14) 1.0534(16) 0.037(6) Uiso 1 1 d . . . H10A H 0.035(3) 1.1459(13) 0.9401(15) 0.026(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.00752(9) 0.00675(8) 0.01037(10) 0.00071(7) 0.00030(8) 0.00031(6) Se1 0.00690(7) 0.00668(6) 0.02045(9) -0.00028(6) -0.00137(7) 0.00011(5) Cl1 0.01191(19) 0.01277(15) 0.0153(2) 0.00345(14) -0.00310(16) -0.00060(14) Cl2 0.01013(18) 0.01086(15) 0.01306(19) 0.00142(13) -0.00148(15) -0.00016(14) S1 0.01057(19) 0.00991(15) 0.0120(2) 0.00041(14) 0.00129(16) -0.00039(14) S2 0.0126(2) 0.01879(18) 0.0119(2) -0.00100(15) -0.00016(16) -0.00111(15) O1 0.0136(6) 0.0114(5) 0.0125(6) 0.0034(4) 0.0023(5) 0.0016(4) O2 0.0124(6) 0.0133(5) 0.0126(6) 0.0025(4) 0.0031(5) 0.0030(5) N1 0.0082(6) 0.0078(5) 0.0151(7) 0.0004(5) 0.0006(6) 0.0014(4) N2 0.0091(6) 0.0080(5) 0.0119(7) -0.0005(5) 0.0002(6) -0.0006(4) C1 0.0089(7) 0.0090(6) 0.0083(7) 0.0004(5) 0.0009(6) -0.0002(5) C2 0.0091(7) 0.0088(6) 0.0087(7) 0.0001(5) 0.0009(6) -0.0002(5) C3 0.0112(7) 0.0113(6) 0.0137(8) 0.0018(6) 0.0012(7) 0.0011(5) C4 0.0115(8) 0.0100(6) 0.0136(9) -0.0014(6) 0.0000(6) -0.0018(6) C5 0.0101(8) 0.0150(7) 0.0168(9) 0.0014(6) 0.0002(7) 0.0019(6) C6 0.0094(8) 0.0144(7) 0.0171(9) 0.0002(6) -0.0006(7) -0.0030(6) C7 0.0090(8) 0.0194(8) 0.0153(9) 0.0024(7) 0.0016(7) -0.0005(6) C8 0.0134(8) 0.0179(7) 0.0146(9) -0.0031(7) 0.0008(7) -0.0027(7) C9 0.0168(10) 0.0223(8) 0.0157(9) 0.0069(7) 0.0013(8) -0.0016(7) C10 0.0178(10) 0.0309(10) 0.0183(10) -0.0022(8) 0.0064(8) 0.0047(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Co1 O1 2.0754(12) . ? Co1 O2 2.1042(12) . ? Co1 N1 2.1788(11) . ? Co1 N2 2.1837(11) 3_656 ? Co1 Cl1 2.4155(5) . ? Co1 Cl2 2.4365(5) . ? Se1 N2 1.7876(12) . ? Se1 N1 1.7909(11) . ? S1 O1 1.5373(12) . ? S1 C8 1.7837(18) . ? S1 C7 1.7850(18) . ? S2 O2 1.5283(12) . ? S2 C10 1.787(2) . ? S2 C9 1.7900(18) . ? N1 C1 1.3355(18) . ? N2 C2 1.3388(18) . ? N2 Co1 2.1837(11) 3_646 ? C1 C3 1.424(2) . ? C1 C2 1.4553(18) . ? C2 C4 1.428(2) . ? C3 C5 1.362(2) . ? C3 H3 0.997(15) . ? C4 C6 1.355(2) . ? C4 H4 0.961(17) . ? C5 C6 1.438(2) . ? C5 H5 0.948(16) . ? C6 H6A 0.982(19) . ? C7 H7C 0.934(19) . ? C7 H7B 0.993(18) . ? C7 H7A 0.92(2) . ? C8 H8C 1.022(16) . ? C8 H8B 0.95(2) . ? C8 H8A 0.97(2) . ? C9 H9C 0.97(2) . ? C9 H9B 0.95(2) . ? C9 H9A 0.98(2) . ? C10 H10C 0.95(2) . ? C10 H10B 1.02(2) . ? C10 H10A 1.02(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O2 177.29(5) . . ? O1 Co1 N1 86.31(4) . . ? O2 Co1 N1 91.69(5) . . ? O1 Co1 N2 89.97(5) . 3_656 ? O2 Co1 N2 91.96(4) . 3_656 ? N1 Co1 N2 175.82(6) . 3_656 ? O1 Co1 Cl1 90.25(3) . . ? O2 Co1 Cl1 91.51(4) . . ? N1 Co1 Cl1 87.78(4) . . ? N2 Co1 Cl1 94.15(4) 3_656 . ? O1 Co1 Cl2 92.37(4) . . ? O2 Co1 Cl2 85.86(3) . . ? N1 Co1 Cl2 92.14(4) . . ? N2 Co1 Cl2 86.10(4) 3_656 . ? Cl1 Co1 Cl2 177.368(17) . . ? N2 Se1 N1 92.57(5) . . ? O1 S1 C8 105.68(8) . . ? O1 S1 C7 103.44(7) . . ? C8 S1 C7 98.33(9) . . ? O2 S2 C10 103.12(9) . . ? O2 S2 C9 106.74(8) . . ? C10 S2 C9 97.71(10) . . ? S1 O1 Co1 121.47(6) . . ? S2 O2 Co1 128.66(7) . . ? C1 N1 Se1 108.63(9) . . ? C1 N1 Co1 135.08(9) . . ? Se1 N1 Co1 116.29(6) . . ? C2 N2 Se1 108.67(9) . . ? C2 N2 Co1 134.00(9) . 3_646 ? Se1 N2 Co1 117.25(6) . 3_646 ? N1 C1 C3 125.01(12) . . ? N1 C1 C2 115.09(13) . . ? C3 C1 C2 119.82(13) . . ? N2 C2 C4 125.62(12) . . ? N2 C2 C1 114.96(13) . . ? C4 C2 C1 119.39(13) . . ? C5 C3 C1 118.67(13) . . ? C5 C3 H3 121.6(10) . . ? C1 C3 H3 119.7(10) . . ? C6 C4 C2 118.79(13) . . ? C6 C4 H4 122.4(11) . . ? C2 C4 H4 118.8(11) . . ? C3 C5 C6 121.49(16) . . ? C3 C5 H5 119.2(10) . . ? C6 C5 H5 119.3(10) . . ? C4 C6 C5 121.84(16) . . ? C4 C6 H6A 120.7(11) . . ? C5 C6 H6A 117.5(11) . . ? S1 C7 H7C 107.2(12) . . ? S1 C7 H7B 106.8(12) . . ? H7C C7 H7B 112.6(16) . . ? S1 C7 H7A 109.1(14) . . ? H7C C7 H7A 111.4(17) . . ? H7B C7 H7A 109.6(17) . . ? S1 C8 H8C 106.6(10) . . ? S1 C8 H8B 105.4(13) . . ? H8C C8 H8B 114.2(15) . . ? S1 C8 H8A 107.1(12) . . ? H8C C8 H8A 114.1(14) . . ? H8B C8 H8A 108.8(17) . . ? S2 C9 H9C 109.8(10) . . ? S2 C9 H9B 105.8(12) . . ? H9C C9 H9B 117.0(17) . . ? S2 C9 H9A 107.0(12) . . ? H9C C9 H9A 111.0(18) . . ? H9B C9 H9A 105.7(18) . . ? S2 C10 H10C 106.2(13) . . ? S2 C10 H10B 107.2(13) . . ? H10C C10 H10B 109.2(18) . . ? S2 C10 H10A 107.0(12) . . ? H10C C10 H10A 115.4(17) . . ? H10B C10 H10A 111.3(17) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 32.84 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.493 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.075 _iucr_refine_instructions_details ; TITL LLCo_0m in P2(1)2(1)2(1) CELL 0.71073 8.5078 13.3811 14.3894 90.000 90.000 90.000 ZERR 4.00 0.0008 0.0012 0.0013 0.000 0.000 0.000 LATT -1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H N O S CL CO SE UNIT 40 64 8 8 8 8 4 4 TEMP 100.00 SIZE 0.06 0.153 0.572 L.S. 10 BOND $H FMAP 2 PLAN 3 acta TWIN -1 0 0 0 -1 0 0 0 -1 WGHT 0.008900 BASF 0.15395 FVAR 0.11283 CO1 7 0.492922 1.137559 0.760099 11.00000 0.00752 0.00675 = 0.01037 0.00071 0.00030 0.00031 SE1 8 0.558168 0.888543 0.758390 11.00000 0.00690 0.00668 = 0.02045 -0.00028 -0.00137 0.00011 CL1 6 0.665425 1.082420 0.883172 11.00000 0.01191 0.01277 = 0.01527 0.00345 -0.00310 -0.00060 CL2 6 0.309559 1.194476 0.641287 11.00000 0.01013 0.01086 = 0.01306 0.00142 -0.00148 -0.00016 S1 5 0.698311 1.167927 0.579097 11.00000 0.01057 0.00991 = 0.01197 0.00041 0.00129 -0.00039 S2 5 0.303648 1.145215 0.958833 11.00000 0.01260 0.01879 = 0.01185 -0.00100 -0.00016 -0.00111 O1 4 0.661259 1.099331 0.661953 11.00000 0.01355 0.01144 = 0.01247 0.00340 0.00228 0.00163 O2 4 0.314348 1.172541 0.855900 11.00000 0.01239 0.01331 = 0.01258 0.00250 0.00312 0.00295 N1 3 0.411158 0.983752 0.748567 11.00000 0.00824 0.00782 = 0.01508 0.00043 0.00057 0.00143 N2 3 0.418850 0.790800 0.738739 11.00000 0.00908 0.00803 = 0.01191 -0.00048 0.00023 -0.00056 C1 1 0.271738 0.940014 0.735730 11.00000 0.00888 0.00902 = 0.00830 0.00040 0.00087 -0.00023 C2 1 0.275777 0.831448 0.730241 11.00000 0.00913 0.00877 = 0.00868 0.00006 0.00092 -0.00020 C3 1 0.124991 0.990997 0.732299 11.00000 0.01124 0.01127 = 0.01373 0.00184 0.00117 0.00107 H3 2 0.122336 1.065355 0.736869 11.00000 0.01241 C4 1 0.132140 0.777455 0.719561 11.00000 0.01147 0.00998 = 0.01359 -0.00140 -0.00001 -0.00175 H4 2 0.136489 0.706155 0.712052 11.00000 0.01715 C5 1 -0.009013 0.936237 0.722981 11.00000 0.01015 0.01502 = 0.01683 0.00141 0.00021 0.00185 H5 2 -0.107046 0.969713 0.719338 11.00000 0.00609 C6 1 -0.004808 0.829054 0.716460 11.00000 0.00939 0.01440 = 0.01714 0.00015 -0.00061 -0.00297 H6A 2 -0.105529 0.794016 0.709705 11.00000 0.02281 C7 1 0.894767 1.134444 0.548665 11.00000 0.00898 0.01943 = 0.01528 0.00238 0.00162 -0.00055 H7C 2 0.917980 1.166306 0.492547 11.00000 0.01337 H7B 2 0.897273 1.060503 0.543425 11.00000 0.02854 H7A 2 0.961382 1.154550 0.595013 11.00000 0.02957 C8 1 0.599984 1.113878 0.481833 11.00000 0.01338 0.01792 = 0.01463 -0.00307 0.00085 -0.00270 H8C 2 0.632645 1.040404 0.479810 11.00000 0.00786 H8B 2 0.491677 1.124221 0.492931 11.00000 0.02548 H8A 2 0.630715 1.151873 0.427551 11.00000 0.02510 C9 1 0.281255 1.012344 0.964489 11.00000 0.01676 0.02235 = 0.01573 0.00690 0.00130 -0.00157 H9C 2 0.192001 0.991888 0.927037 11.00000 0.02125 H9B 2 0.380839 0.985237 0.948259 11.00000 0.03578 H9A 2 0.265224 0.995179 1.029876 11.00000 0.03105 C10 1 0.106304 1.178151 0.988311 11.00000 0.01784 0.03091 = 0.01829 -0.00222 0.00642 0.00469 H10C 2 0.103351 1.248989 0.990425 11.00000 0.02826 H10B 2 0.084771 1.150307 1.053366 11.00000 0.03700 H10A 2 0.035208 1.145948 0.940078 11.00000 0.02618 HKLF 4 REM LLCo_0m in P2(1)2(1)2(1) REM R1 = 0.0206 for 5458 Fo > 4sig(Fo) and 0.0264 for all 6035 data REM 246 parameters refined using 0 restraints END WGHT 0.0084 0.0000 REM Highest difference peak 0.493, deepest hole -0.493, 1-sigma level 0.075 Q1 1 0.4476 1.1772 0.7606 11.00000 0.05 0.49 Q2 1 0.2616 0.8818 0.7317 11.00000 0.05 0.45 Q3 1 -0.0125 0.8835 0.7206 11.00000 0.05 0.42 ; _database_code_depnum_ccdc_archive 'CCDC 932442' ####################################################################### # # 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_twin5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 Cl2 Fe N2 O2 S2 Se' _chemical_formula_sum 'C10 H16 Cl2 Fe N2 O2 S2 Se' _chemical_formula_weight 466.08 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' S S 0.1246 0.1234 '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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _space_group_name_H-M_alt 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.4810(6) _cell_length_b 13.4884(9) _cell_length_c 14.3386(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1640.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 598 _cell_measurement_theta_min 27.76 _cell_measurement_theta_max 2.79 _exptl_crystal_description rod _exptl_crystal_colour green _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.887 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 3.719 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.3824 _exptl_absorpt_correction_T_max 0.8966 _exptl_absorpt_process_details SADABS _exptl_special_details ; A crystal of suitable size and quality was chosen, mounted in Paratone oil on a MiTeGen polymer loop, and placed in the cold stream of the diffractometer. Data were collected on a Bruker Apex2 instrument with MoK(alpha) radiaiton using 0.5 degree omega and phi scans to ensure complete coverage. Unit cell parameters were determined from at least 50 frames. Data were corrected by SADABS 2008.4 program. The structure was solved in the orthorhombic space group P 21 21 21. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _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 2743 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 30.11 _reflns_number_total 2743 _reflns_number_gt 2520 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0131P)^2^+7.0859P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.475(14) _refine_ls_number_reflns 2743 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0761 _refine_ls_wR_factor_gt 0.0732 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 Se1 Se 0.94290(6) 0.61002(3) 0.23904(4) 0.01156(11) Uani 1 1 d . . . N1 N 1.0898(5) 0.5152(3) 0.2500(3) 0.0110(8) Uani 1 1 d . . . N2 N 1.0820(5) 0.7072(3) 0.2614(3) 0.0112(8) Uani 1 1 d . . . Fe1 Fe 1.00885(8) 0.36063(5) 0.23780(5) 0.00876(13) Uani 1 1 d . . . Cl2 Cl 1.19594(15) 0.30278(9) 0.35831(8) 0.0121(2) Uani 1 1 d . . . Cl1 Cl 0.83167(15) 0.41705(9) 0.11318(9) 0.0140(2) Uani 1 1 d . . . S2 S 0.80215(15) 0.33040(9) 0.42078(9) 0.0111(2) Uani 1 1 d . . . S1 S 1.19977(16) 0.35466(10) 0.03881(9) 0.0149(2) Uani 1 1 d . . . O3 O 0.8384(4) 0.3961(3) 0.3366(2) 0.0134(7) Uani 1 1 d . . . O4 O 1.1890(5) 0.3287(3) 0.1427(3) 0.0141(7) Uani 1 1 d . . . C5 C 1.2246(6) 0.6662(3) 0.2708(3) 0.0088(8) Uani 1 1 d . . . C6 C 1.2303(6) 0.5593(3) 0.2632(4) 0.0109(9) Uani 1 1 d . . . C7 C 1.3765(6) 0.5083(4) 0.2683(4) 0.0130(9) Uani 1 1 d . . . H5 H 1.3807 0.4395 0.2650 0.016 Uiso 1 1 calc R . . C10 C 1.3686(6) 0.7202(4) 0.2818(4) 0.0134(10) Uani 1 1 d . . . H8 H 1.3680 0.7889 0.2862 0.016 Uiso 1 1 calc R . . C1 C 0.6062(6) 0.3638(4) 0.4513(4) 0.0153(10) Uani 1 1 d . . . H1C H 0.5987 0.4346 0.4566 0.023 Uiso 1 1 calc R . . H1B H 0.5790 0.3338 0.5098 0.023 Uiso 1 1 calc R . . H1A H 0.5349 0.3410 0.4039 0.023 Uiso 1 1 calc R . . C8 C 1.5098(6) 0.5629(4) 0.2782(4) 0.0147(10) Uani 1 1 d . . . H6 H 1.6065 0.5305 0.2803 0.018 Uiso 1 1 calc R . . C9 C 1.5066(6) 0.6688(4) 0.2855(3) 0.0133(9) Uani 1 1 d . . . H7 H 1.6008 0.7031 0.2930 0.016 Uiso 1 1 calc R . . C3 C 1.3982(7) 0.3226(5) 0.0105(4) 0.0241(13) Uani 1 1 d . . . H3C H 1.4687 0.3543 0.0535 0.036 Uiso 1 1 calc R . . H3B H 1.4217 0.3442 -0.0518 0.036 Uiso 1 1 calc R . . H3A H 1.4109 0.2520 0.0145 0.036 Uiso 1 1 calc R . . C2 C 0.9018(6) 0.3855(4) 0.5169(4) 0.0171(10) Uani 1 1 d . . . H2C H 1.0134 0.3766 0.5097 0.026 Uiso 1 1 calc R . . H2B H 0.8677 0.3546 0.5737 0.026 Uiso 1 1 calc R . . H2A H 0.8780 0.4551 0.5190 0.026 Uiso 1 1 calc R . . C4 C 1.2181(7) 0.4862(4) 0.0336(4) 0.0184(11) Uani 1 1 d . . . H4C H 1.1207 0.5162 0.0527 0.028 Uiso 1 1 calc R . . H4B H 1.2420 0.5059 -0.0292 0.028 Uiso 1 1 calc R . . H4A H 1.3013 0.5073 0.0743 0.028 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 Se1 0.0072(2) 0.00751(17) 0.0199(2) -0.00006(19) -0.00114(19) 0.00046(17) N1 0.013(2) 0.0058(15) 0.015(2) 0.0002(15) 0.0016(18) -0.0002(13) N2 0.0100(19) 0.0097(16) 0.0137(19) 0.0019(16) -0.0043(17) -0.0001(14) Fe1 0.0079(3) 0.0076(3) 0.0108(3) 0.0003(2) 0.0012(3) 0.0000(2) Cl2 0.0101(5) 0.0128(5) 0.0134(5) 0.0012(4) -0.0023(4) -0.0008(4) Cl1 0.0119(5) 0.0135(5) 0.0166(5) 0.0040(4) -0.0027(5) -0.0003(4) S2 0.0103(5) 0.0100(5) 0.0129(5) 0.0008(4) 0.0003(5) 0.0004(4) S1 0.0121(6) 0.0194(6) 0.0132(5) -0.0015(5) 0.0001(5) -0.0013(5) O3 0.0112(17) 0.0137(16) 0.0152(17) 0.0014(14) 0.0037(14) 0.0019(15) O4 0.0148(18) 0.0146(16) 0.0130(16) 0.0012(14) 0.0033(15) 0.0026(15) C5 0.009(2) 0.0103(19) 0.0073(19) 0.0022(17) 0.0007(17) 0.0010(16) C6 0.010(2) 0.011(2) 0.011(2) 0.0012(18) 0.0039(19) -0.0001(16) C7 0.011(2) 0.014(2) 0.014(2) 0.002(2) -0.001(2) 0.0019(17) C10 0.016(2) 0.010(2) 0.014(2) -0.0022(18) 0.003(2) 0.0009(18) C1 0.009(2) 0.019(2) 0.017(2) 0.003(2) 0.0008(19) -0.001(2) C8 0.011(2) 0.016(2) 0.018(2) 0.0054(19) 0.002(2) 0.0039(19) C9 0.010(2) 0.014(2) 0.016(2) -0.0007(17) -0.0038(19) -0.0001(18) C3 0.017(3) 0.035(3) 0.021(3) -0.005(2) 0.009(2) 0.004(2) C2 0.018(3) 0.017(2) 0.015(2) -0.006(2) 0.0002(19) -0.002(2) C4 0.021(3) 0.019(2) 0.016(3) 0.005(2) 0.001(2) -0.001(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Se1 N1 1.792(4) . ? Se1 N2 1.793(4) . ? N1 C6 1.345(6) . ? N1 Fe1 2.202(4) . ? N2 C5 1.337(6) . ? N2 Fe1 2.208(4) 3_755 ? Fe1 O3 2.080(4) . ? Fe1 O4 2.093(4) . ? Fe1 N2 2.208(4) 3_745 ? Fe1 Cl1 2.4556(14) . ? Fe1 Cl2 2.4724(14) . ? S2 O3 1.529(4) . ? S2 C1 1.777(5) . ? S2 C2 1.779(5) . ? S1 O4 1.532(4) . ? S1 C4 1.782(5) . ? S1 C3 1.784(6) . ? C5 C10 1.431(7) . ? C5 C6 1.447(6) . ? C6 C7 1.419(7) . ? C7 C8 1.357(7) . ? C7 H5 0.9300 . ? C10 C9 1.361(7) . ? C10 H8 0.9300 . ? C1 H1C 0.9600 . ? C1 H1B 0.9600 . ? C1 H1A 0.9600 . ? C8 C9 1.431(7) . ? C8 H6 0.9300 . ? C9 H7 0.9300 . ? C3 H3C 0.9600 . ? C3 H3B 0.9600 . ? C3 H3A 0.9600 . ? C2 H2C 0.9600 . ? C2 H2B 0.9600 . ? C2 H2A 0.9600 . ? C4 H4C 0.9600 . ? C4 H4B 0.9600 . ? C4 H4A 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 N1 Se1 N2 92.81(17) . . ? C6 N1 Se1 108.2(3) . . ? C6 N1 Fe1 134.9(3) . . ? Se1 N1 Fe1 116.9(2) . . ? C5 N2 Se1 108.1(3) . . ? C5 N2 Fe1 134.7(3) . 3_755 ? Se1 N2 Fe1 117.2(2) . 3_755 ? O3 Fe1 O4 177.03(17) . . ? O3 Fe1 N1 86.82(15) . . ? O4 Fe1 N1 91.08(15) . . ? O3 Fe1 N2 88.26(15) . 3_745 ? O4 Fe1 N2 93.76(15) . 3_745 ? N1 Fe1 N2 174.66(17) . 3_745 ? O3 Fe1 Cl1 89.94(11) . . ? O4 Fe1 Cl1 92.07(11) . . ? N1 Fe1 Cl1 87.42(12) . . ? N2 Fe1 Cl1 94.64(11) 3_745 . ? O3 Fe1 Cl2 92.45(11) . . ? O4 Fe1 Cl2 85.54(11) . . ? N1 Fe1 Cl2 92.49(11) . . ? N2 Fe1 Cl2 85.66(11) 3_745 . ? Cl1 Fe1 Cl2 177.60(5) . . ? O3 S2 C1 103.6(2) . . ? O3 S2 C2 105.9(2) . . ? C1 S2 C2 98.5(3) . . ? O4 S1 C4 105.9(2) . . ? O4 S1 C3 102.8(3) . . ? C4 S1 C3 98.6(3) . . ? S2 O3 Fe1 122.9(2) . . ? S1 O4 Fe1 129.0(2) . . ? N2 C5 C10 124.9(4) . . ? N2 C5 C6 115.8(4) . . ? C10 C5 C6 119.2(4) . . ? N1 C6 C7 124.6(4) . . ? N1 C6 C5 114.9(4) . . ? C7 C6 C5 120.5(4) . . ? C8 C7 C6 118.1(4) . . ? C8 C7 H5 121.0 . . ? C6 C7 H5 121.0 . . ? C9 C10 C5 118.6(4) . . ? C9 C10 H8 120.7 . . ? C5 C10 H8 120.7 . . ? S2 C1 H1C 109.5 . . ? S2 C1 H1B 109.5 . . ? H1C C1 H1B 109.5 . . ? S2 C1 H1A 109.5 . . ? H1C C1 H1A 109.5 . . ? H1B C1 H1A 109.5 . . ? C7 C8 C9 122.2(5) . . ? C7 C8 H6 118.9 . . ? C9 C8 H6 118.9 . . ? C10 C9 C8 121.4(5) . . ? C10 C9 H7 119.3 . . ? C8 C9 H7 119.3 . . ? S1 C3 H3C 109.5 . . ? S1 C3 H3B 109.5 . . ? H3C C3 H3B 109.5 . . ? S1 C3 H3A 109.5 . . ? H3C C3 H3A 109.5 . . ? H3B C3 H3A 109.5 . . ? S2 C2 H2C 109.5 . . ? S2 C2 H2B 109.5 . . ? H2C C2 H2B 109.5 . . ? S2 C2 H2A 109.5 . . ? H2C C2 H2A 109.5 . . ? H2B C2 H2A 109.5 . . ? S1 C4 H4C 109.5 . . ? S1 C4 H4B 109.5 . . ? H4C C4 H4B 109.5 . . ? S1 C4 H4A 109.5 . . ? H4C C4 H4A 109.5 . . ? H4B C4 H4A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.11 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.098 _refine_diff_density_min -1.401 _refine_diff_density_rms 0.149 _iucr_refine_instructions_details ; TITL twin4 in P2(1)2(1)2(1) CELL 0.71073 8.4810 13.4884 14.3386 90.000 90.000 90.000 ZERR 4.00 0.0006 0.0009 0.0011 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H N O S CL FE SE UNIT 40 64 8 8 8 8 4 4 MERG 2 FMAP 2 PLAN 20 SIZE 0.03 0.09 0.32 ACTA BOND $H L.S. 8 TEMP 100.00 WGHT 0.013100 7.085900 BASF 0.13200 FVAR 0.39130 SE1 8 0.942897 0.610021 0.239041 11.00000 0.00723 0.00751 = 0.01994 -0.00006 -0.00114 0.00046 N1 3 1.089751 0.515207 0.249990 11.00000 0.01259 0.00579 = 0.01451 0.00023 0.00164 -0.00021 N2 3 1.081987 0.707230 0.261358 11.00000 0.01000 0.00975 = 0.01371 0.00187 -0.00426 -0.00006 FE1 7 1.008847 0.360633 0.237799 11.00000 0.00790 0.00760 = 0.01077 0.00028 0.00119 0.00003 CL2 6 1.195936 0.302782 0.358314 11.00000 0.01012 0.01278 = 0.01342 0.00120 -0.00231 -0.00082 CL1 6 0.831667 0.417046 0.113183 11.00000 0.01189 0.01352 = 0.01663 0.00404 -0.00273 -0.00035 S2 5 0.802146 0.330397 0.420775 11.00000 0.01026 0.01003 = 0.01294 0.00083 0.00030 0.00040 S1 5 1.199771 0.354664 0.038808 11.00000 0.01209 0.01936 = 0.01317 -0.00153 0.00008 -0.00134 O3 4 0.838385 0.396141 0.336606 11.00000 0.01122 0.01375 = 0.01519 0.00139 0.00373 0.00186 O4 4 1.189014 0.328737 0.142651 11.00000 0.01475 0.01463 = 0.01301 0.00115 0.00325 0.00262 C5 1 1.224641 0.666158 0.270773 11.00000 0.00894 0.01026 = 0.00726 0.00218 0.00070 0.00103 C6 1 1.230265 0.559254 0.263185 11.00000 0.01022 0.01127 = 0.01126 0.00124 0.00388 -0.00006 C7 1 1.376458 0.508322 0.268319 11.00000 0.01059 0.01404 = 0.01434 0.00201 -0.00146 0.00187 AFIX 43 H5 2 1.380743 0.439518 0.264993 11.00000 -1.20000 AFIX 0 C10 1 1.368650 0.720163 0.281755 11.00000 0.01619 0.00993 = 0.01408 -0.00215 0.00260 0.00087 AFIX 43 H8 2 1.368000 0.788947 0.286216 11.00000 -1.20000 AFIX 0 C1 1 0.606159 0.363801 0.451284 11.00000 0.00942 0.01919 = 0.01741 0.00317 0.00085 -0.00129 AFIX 137 H1C 2 0.598718 0.434592 0.456618 11.00000 -1.50000 H1B 2 0.578960 0.333832 0.509841 11.00000 -1.50000 H1A 2 0.534911 0.341026 0.403874 11.00000 -1.50000 AFIX 0 C8 1 1.509832 0.562947 0.278224 11.00000 0.01058 0.01551 = 0.01791 0.00540 0.00152 0.00392 AFIX 43 H6 2 1.606547 0.530529 0.280329 11.00000 -1.20000 AFIX 0 C9 1 1.506639 0.668764 0.285538 11.00000 0.00975 0.01393 = 0.01623 -0.00068 -0.00377 -0.00012 AFIX 43 H7 2 1.600849 0.703136 0.293036 11.00000 -1.20000 AFIX 0 C3 1 1.398193 0.322579 0.010493 11.00000 0.01663 0.03450 = 0.02109 -0.00534 0.00918 0.00400 AFIX 137 H3C 2 1.468725 0.354271 0.053544 11.00000 -1.50000 H3B 2 1.421659 0.344217 -0.051761 11.00000 -1.50000 H3A 2 1.410946 0.251986 0.014463 11.00000 -1.50000 AFIX 0 C2 1 0.901799 0.385513 0.516863 11.00000 0.01838 0.01738 = 0.01541 -0.00577 0.00025 -0.00220 AFIX 137 H2C 2 1.013444 0.376581 0.509707 11.00000 -1.50000 H2B 2 0.867713 0.354640 0.573720 11.00000 -1.50000 H2A 2 0.878012 0.455059 0.519011 11.00000 -1.50000 AFIX 0 C4 1 1.218079 0.486189 0.033560 11.00000 0.02072 0.01882 = 0.01573 0.00532 0.00072 -0.00145 AFIX 137 H4C 2 1.120717 0.516247 0.052711 11.00000 -1.50000 H4B 2 1.242035 0.505877 -0.029199 11.00000 -1.50000 H4A 2 1.301346 0.507282 0.074344 11.00000 -1.50000 HKLF 5 REM twin4 in P2(1)2(1)2(1) REM R1 = 0.0366 for 2520 Fo > 4sig(Fo) and 0.0431 for all 2743 data REM 186 parameters refined using 0 restraints END WGHT 0.0130 7.0949 REM Highest difference peak 1.098, deepest hole -1.401, 1-sigma level 0.149 Q1 1 0.9933 0.5783 0.2174 11.00000 0.05 1.10 Q2 1 0.8975 0.5770 0.2644 11.00000 0.05 1.02 Q3 1 0.8990 0.6417 0.2155 11.00000 0.05 1.00 Q4 1 0.9857 0.6436 0.2643 11.00000 0.05 0.97 Q5 1 1.0735 0.6448 0.2590 11.00000 0.05 0.75 Q6 1 1.0239 0.6551 0.1904 11.00000 0.05 0.70 Q7 1 0.8384 0.2946 0.4498 11.00000 0.05 0.69 Q8 1 1.1512 0.2740 0.3324 11.00000 0.05 0.63 Q9 1 1.0028 0.4175 0.2236 11.00000 0.05 0.61 Q10 1 1.0783 0.3984 0.2958 11.00000 0.05 0.57 Q11 1 1.3961 0.3666 -0.1146 11.00000 0.05 0.56 Q12 1 1.2221 0.6133 0.2674 11.00000 0.05 0.55 Q13 1 1.2461 0.3253 0.3340 11.00000 0.05 0.55 Q14 1 0.8862 0.3975 0.1473 11.00000 0.05 0.53 Q15 1 0.9549 0.4584 0.3807 11.00000 0.05 0.53 Q16 1 0.9827 0.5845 0.1652 11.00000 0.05 0.52 Q17 1 1.1410 0.3341 0.0149 11.00000 0.05 0.52 Q18 1 0.9893 0.7223 0.2614 11.00000 0.05 0.51 Q19 1 0.7585 0.3039 0.3969 11.00000 0.05 0.51 Q20 1 0.6780 0.4231 0.3385 11.00000 0.05 0.50 ; _database_code_depnum_ccdc_archive 'CCDC 932443' ####################################################################### # # 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_twin5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 Cd0.50 Cl N2 Se' _chemical_formula_sum 'C6 H4 Cd0.50 Cl N2 Se' _chemical_formula_weight 274.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 '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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.7767(17) _cell_length_b 9.284(4) _cell_length_c 10.824(5) _cell_angle_alpha 78.814(7) _cell_angle_beta 82.416(8) _cell_angle_gamma 82.514(7) _cell_volume 366.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 451 _cell_measurement_theta_min 3.22 _cell_measurement_theta_max 26.23 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.002 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 258 _exptl_absorpt_coefficient_mu 6.808 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6855 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details twinabs _exptl_special_details ; A crystal of suitable size and quality was chosen, mounted in Paratone oil on a MiTeGen polymer loop, and placed in the cold stream of the diffractometer. Data were collected on a Bruker Apex2 instrument with MoK(alpha) radiation using 0.5 degree omega and phi scans to ensure complete coverage. Unit cell parameters were determined from at least 50 frames. Data were corrected by SADABS 2008.4 program. The structure was solved in the triclinic space group P-1. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 1495 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1056 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 26.46 _reflns_number_total 1495 _reflns_number_gt 959 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0740P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1495 _refine_ls_number_parameters 102 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1061 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1481 _refine_ls_wR_factor_gt 0.1273 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.971 _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 N1 N 0.142(2) 0.8933(11) 0.3109(8) 0.015(2) Uani 1 1 d . . . Cl1 Cl -0.5118(8) 1.1736(3) 0.3915(3) 0.0177(7) Uani 1 1 d . . . Se2 Se 0.3394(3) 1.01051(14) 0.17169(10) 0.0177(4) Uani 1 1 d . . . N2 N 0.351(3) 0.8742(12) 0.0773(8) 0.021(2) Uani 1 1 d . . . C6 C 0.055(3) 0.5102(14) 0.1852(10) 0.018(3) Uani 1 1 d U . . H6 H 0.042(4) 0.427(12) 0.159(4) 0.022 Uiso 1 1 calc R . . C1 C 0.096(3) 0.7688(14) 0.2788(11) 0.019(3) Uani 1 1 d U . . C2 C -0.054(3) 0.6462(14) 0.3607(11) 0.020(3) Uani 1 1 d . . . H2 H -0.151(10) 0.6515(15) 0.465(11) 0.024 Uiso 1 1 calc R . . C5 C 0.219(3) 0.7558(13) 0.1464(11) 0.018(3) Uani 1 1 d . . . C4 C 0.200(3) 0.6240(14) 0.1037(11) 0.023(3) Uani 1 1 d . . . H4 H 0.272(12) 0.6159(19) 0.033(11) 0.027 Uiso 1 1 calc R . . C3 C -0.079(3) 0.5259(15) 0.3143(11) 0.024(3) Uani 1 1 d . . . H3 H -0.180(16) 0.454(11) 0.363(7) 0.028 Uiso 1 1 calc R . . Cd2 Cd 0.0000 1.0000 0.5000 0.0169(4) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.012(5) 0.021(6) 0.013(5) -0.005(4) -0.002(4) -0.001(4) Cl1 0.0194(15) 0.0195(16) 0.0135(13) -0.0001(11) -0.0032(11) -0.0032(12) Se2 0.0186(7) 0.0230(8) 0.0108(6) -0.0018(5) -0.0013(5) -0.0017(6) N2 0.024(6) 0.029(6) 0.010(5) -0.004(4) -0.008(4) 0.002(5) C6 0.021(5) 0.020(5) 0.016(5) -0.004(4) -0.012(4) 0.000(4) C1 0.010(5) 0.023(6) 0.021(5) 0.002(4) -0.006(4) 0.005(4) C2 0.020(7) 0.025(7) 0.015(6) 0.003(5) -0.009(5) -0.002(5) C5 0.019(6) 0.018(7) 0.015(5) -0.002(5) -0.005(5) 0.004(5) C4 0.022(7) 0.034(8) 0.014(6) -0.008(6) -0.009(5) 0.000(6) C3 0.027(7) 0.026(8) 0.018(6) -0.007(6) -0.003(5) 0.002(6) Cd2 0.0176(7) 0.0224(8) 0.0108(6) -0.0024(5) -0.0012(5) -0.0032(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.308(15) . ? N1 Se2 1.814(9) . ? N1 Cd2 2.412(9) . ? Cl1 Cd2 2.601(3) . ? Cl1 Cd2 2.616(3) 1_455 ? Se2 N2 1.768(9) . ? N2 C5 1.319(15) . ? C6 C4 1.364(17) . ? C6 C3 1.451(15) . ? C6 H6 0.8836 . ? C1 C2 1.430(16) . ? C1 C5 1.471(16) . ? C2 C3 1.329(17) . ? C2 H2 1.1527 . ? C5 C4 1.403(16) . ? C4 H4 0.7887 . ? C3 H3 0.8637 . ? Cd2 N1 2.412(9) 2_576 ? Cd2 Cl1 2.601(3) 2_576 ? Cd2 Cl1 2.616(3) 1_655 ? Cd2 Cl1 2.616(3) 2_476 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 Se2 108.1(8) . . ? C1 N1 Cd2 135.5(8) . . ? Se2 N1 Cd2 116.3(4) . . ? Cd2 Cl1 Cd2 92.75(10) . 1_455 ? N2 Se2 N1 92.2(4) . . ? C5 N2 Se2 109.7(8) . . ? C4 C6 C3 120.2(12) . . ? C4 C6 H6 119.9 . . ? C3 C6 H6 119.9 . . ? N1 C1 C2 126.1(11) . . ? N1 C1 C5 115.5(11) . . ? C2 C1 C5 118.4(11) . . ? C3 C2 C1 119.0(11) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? N2 C5 C4 125.3(11) . . ? N2 C5 C1 114.4(11) . . ? C4 C5 C1 120.3(12) . . ? C6 C4 C5 119.2(11) . . ? C6 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C2 C3 C6 122.9(13) . . ? C2 C3 H3 118.6 . . ? C6 C3 H3 118.6 . . ? N1 Cd2 N1 180.000(2) 2_576 . ? N1 Cd2 Cl1 91.4(2) 2_576 . ? N1 Cd2 Cl1 88.6(2) . . ? N1 Cd2 Cl1 88.6(2) 2_576 2_576 ? N1 Cd2 Cl1 91.4(2) . 2_576 ? Cl1 Cd2 Cl1 180.00(12) . 2_576 ? N1 Cd2 Cl1 96.1(2) 2_576 1_655 ? N1 Cd2 Cl1 83.9(2) . 1_655 ? Cl1 Cd2 Cl1 92.75(10) . 1_655 ? Cl1 Cd2 Cl1 87.25(10) 2_576 1_655 ? N1 Cd2 Cl1 83.9(2) 2_576 2_476 ? N1 Cd2 Cl1 96.1(2) . 2_476 ? Cl1 Cd2 Cl1 87.25(10) . 2_476 ? Cl1 Cd2 Cl1 92.75(10) 2_576 2_476 ? Cl1 Cd2 Cl1 180.000(1) 1_655 2_476 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.46 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.575 _refine_diff_density_min -1.768 _refine_diff_density_rms 0.298 _iucr_refine_instructions_details ; TITL twin4 in P-1 CELL 0.71073 3.7767 9.2839 10.8240 78.814 82.416 82.514 ZERR 2.00 0.0017 0.0041 0.0047 0.007 0.008 0.007 LATT 1 SFAC C H N CL SE CD UNIT 12 8 4 2 2 1 MERG 2 FMAP 2 PLAN 20 SIZE 0.00 0.05 0.06 BOND $H L.S. 10 TEMP 100.00 acta isor 0.008 c1 c6 WGHT 0.074000 BASF 0.36591 FVAR 0.89324 N1 3 0.142026 0.893321 0.310905 11.00000 0.01246 0.02127 = 0.01299 -0.00454 -0.00219 -0.00072 CL1 4 -0.511828 1.173630 0.391537 11.00000 0.01944 0.01954 = 0.01351 -0.00011 -0.00320 -0.00320 SE2 5 0.339442 1.010514 0.171687 11.00000 0.01856 0.02304 = 0.01081 -0.00179 -0.00130 -0.00172 N2 3 0.350805 0.874168 0.077259 11.00000 0.02398 0.02946 = 0.01021 -0.00422 -0.00834 0.00223 C6 1 0.054598 0.510158 0.185172 11.00000 0.02085 0.02018 = 0.01602 -0.00379 -0.01206 -0.00024 AFIX 44 H6 2 0.041927 0.426567 0.159278 11.00000 -1.20000 AFIX 0 C1 1 0.095601 0.768847 0.278846 11.00000 0.00971 0.02322 = 0.02128 0.00223 -0.00638 0.00468 C2 1 -0.054124 0.646170 0.360727 11.00000 0.02015 0.02477 = 0.01536 0.00334 -0.00945 -0.00198 AFIX 44 H2 2 -0.151375 0.651543 0.465411 11.00000 -1.20000 AFIX 0 C5 1 0.219347 0.755759 0.146415 11.00000 0.01894 0.01849 = 0.01509 -0.00152 -0.00476 0.00370 C4 1 0.200074 0.624016 0.103654 11.00000 0.02158 0.03444 = 0.01444 -0.00822 -0.00900 -0.00001 AFIX 44 H4 2 0.272497 0.615891 0.033317 11.00000 -1.20000 AFIX 0 C3 1 -0.079436 0.525911 0.314311 11.00000 0.02694 0.02649 = 0.01773 -0.00688 -0.00347 0.00165 AFIX 44 H3 2 -0.180079 0.453991 0.363162 11.00000 -1.20000 AFIX 0 MOLE 1 CD2 6 0.000000 1.000000 0.500000 10.50000 0.01755 0.02243 = 0.01082 -0.00241 -0.00123 -0.00324 HKLF 5 REM twin4 in P-1 REM R1 = 0.0600 for 959 Fo > 4sig(Fo) and 0.1061 for all 1495 data REM 102 parameters refined using 12 restraints END WGHT 0.0733 0.0000 REM Highest difference peak 1.575, deepest hole -1.768, 1-sigma level 0.298 Q1 1 0.2114 0.9310 0.5341 11.00000 0.05 1.58 Q2 1 0.4042 1.1034 0.1750 11.00000 0.05 1.28 Q3 1 0.5542 0.9572 0.1949 11.00000 0.05 1.24 Q4 1 0.6555 0.9036 0.2577 11.00000 0.05 1.14 Q5 1 0.5927 0.9994 0.1257 11.00000 0.05 1.11 Q6 1 0.1602 1.0299 0.2440 11.00000 0.05 1.10 Q7 1 0.2222 0.9836 0.4474 11.00000 0.05 1.09 Q8 1 0.0991 1.1012 0.4806 11.00000 0.05 1.07 Q9 1 -0.3408 1.1149 0.4121 11.00000 0.05 1.05 Q10 1 -0.6613 1.1412 0.3768 11.00000 0.05 0.92 Q11 1 -0.2780 0.7308 0.5170 11.00000 0.05 0.91 Q12 1 -0.3382 0.6983 0.5539 11.00000 0.05 0.90 Q13 1 0.5942 0.7649 0.0409 11.00000 0.05 0.89 Q14 1 -0.5065 0.4029 0.2594 11.00000 0.05 0.89 Q15 1 -0.3960 0.4041 0.4358 11.00000 0.05 0.88 Q16 1 -0.8546 1.1815 0.4355 11.00000 0.05 0.87 Q17 1 0.3676 0.8821 0.1639 11.00000 0.05 0.86 Q18 1 -0.2228 0.7107 0.1383 11.00000 0.05 0.86 Q19 1 -0.9656 1.2113 0.3518 11.00000 0.05 0.85 Q20 1 0.1016 0.5162 0.2669 11.00000 0.05 0.81 ; _database_code_depnum_ccdc_archive 'CCDC 932444' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Cl2 Mn N4 Se2' _chemical_formula_sum 'C12 H8 Cl2 Mn N4 Se2' _chemical_formula_weight 491.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.7203(10) _cell_length_b 9.278(2) _cell_length_c 10.769(3) _cell_angle_alpha 80.055(4) _cell_angle_beta 81.254(4) _cell_angle_gamma 83.353(4) _cell_volume 360.37(16) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4837 _cell_measurement_theta_min 0.5957 _cell_measurement_theta_max 0.7457 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 235 _exptl_absorpt_coefficient_mu 6.332 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.2797 _exptl_absorpt_correction_T_max 0.7025 _exptl_absorpt_process_details SADABS _exptl_special_details ; A crystal of suitable size and quality was chosen, mounted in Paratone oil on a MiTeGen polymer loop, and placed in the cold stream of the diffractometer. Data were collected on a Bruker Apex2 instrument with MoK(alpha) radiaiton using 0.5 degree omega and phi scans to ensure complete coverage. Unit cell parameters were determined from at least 50 frames. Data were corrected by SADABS 2008.4 program. The structure was solved in the triclinic space group P-1. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4125 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 2 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 26.33 _reflns_number_total 1447 _reflns_number_gt 1267 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WINGX (Farrugia, 1999)' _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.0318P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0098(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1447 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0311 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0618 _refine_ls_wR_factor_gt 0.0595 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 Mn1 Mn 0.0000 0.0000 0.5000 0.01218(17) Uani 1 2 d S . . Se1 Se 0.33900(7) 0.01059(3) 0.17506(3) 0.01392(13) Uani 1 1 d . . . Cl1 Cl 0.49890(18) 0.16624(8) 0.39767(7) 0.01400(19) Uani 1 1 d . . . N1 N 0.1393(6) -0.1043(3) 0.3152(2) 0.0130(6) Uani 1 1 d . . . N2 N 0.3509(6) -0.1270(3) 0.0774(2) 0.0158(6) Uani 1 1 d . . . C1 C 0.1955(8) -0.3788(4) 0.1042(3) 0.0201(7) Uani 1 1 d . . . H1 H 0.2783 -0.3883 0.0199 0.024 Uiso 1 1 calc R . . C2 C 0.0537(8) -0.4913(4) 0.1859(3) 0.0207(8) Uani 1 1 d . . . H2 H 0.0412 -0.5795 0.1574 0.025 Uiso 1 1 calc R . . C3 C -0.0775(8) -0.4782(4) 0.3149(3) 0.0193(7) Uani 1 1 d . . . H3 H -0.1798 -0.5575 0.3678 0.023 Uiso 1 1 calc R . . C4 C -0.0590(8) -0.3543(3) 0.3636(3) 0.0161(7) Uani 1 1 d . . . H4 H -0.1438 -0.3492 0.4487 0.019 Uiso 1 1 calc R . . C5 C 0.0927(7) -0.2321(3) 0.2820(3) 0.0136(7) Uani 1 1 d . . . C6 C 0.2168(7) -0.2444(3) 0.1494(3) 0.0143(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0121(3) 0.0128(4) 0.0119(4) -0.0036(3) 0.0001(3) -0.0018(3) Se1 0.01591(18) 0.0145(2) 0.0113(2) -0.00314(13) 0.00039(12) -0.00277(12) Cl1 0.0150(4) 0.0120(4) 0.0149(4) -0.0024(3) -0.0004(3) -0.0030(3) N1 0.0127(12) 0.0158(15) 0.0105(13) -0.0042(11) 0.0004(10) -0.0013(10) N2 0.0160(13) 0.0201(15) 0.0120(14) -0.0060(12) -0.0008(10) -0.0001(11) C1 0.0237(16) 0.0199(19) 0.0189(18) -0.0094(15) -0.0045(14) 0.0000(14) C2 0.0229(16) 0.0141(18) 0.028(2) -0.0103(16) -0.0073(14) -0.0008(14) C3 0.0171(15) 0.0154(18) 0.025(2) 0.0002(15) -0.0055(14) -0.0018(13) C4 0.0182(15) 0.0153(18) 0.0140(17) -0.0013(14) -0.0012(12) -0.0005(13) C5 0.0093(13) 0.0170(18) 0.0151(17) -0.0058(14) -0.0031(12) 0.0030(12) C6 0.0146(14) 0.0154(18) 0.0132(17) -0.0037(14) -0.0036(12) 0.0023(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 N1 2.324(2) . ? Mn1 N1 2.324(2) 2_556 ? Mn1 Cl1 2.5379(8) 2_656 ? Mn1 Cl1 2.5379(8) 1_455 ? Mn1 Cl1 2.5480(8) . ? Mn1 Cl1 2.5480(8) 2_556 ? Se1 N2 1.782(2) . ? Se1 N1 1.804(3) . ? Cl1 Mn1 2.5379(8) 1_655 ? N1 C5 1.333(4) . ? N2 C6 1.323(4) . ? C1 C2 1.346(5) . ? C1 C6 1.429(4) . ? C1 H1 0.9300 . ? C2 C3 1.421(5) . ? C2 H2 0.9300 . ? C3 C4 1.356(4) . ? C3 H3 0.9300 . ? C4 C5 1.425(4) . ? C4 H4 0.9300 . ? C5 C6 1.453(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Mn1 N1 180.000(1) . 2_556 ? N1 Mn1 Cl1 91.62(7) . 2_656 ? N1 Mn1 Cl1 88.38(7) 2_556 2_656 ? N1 Mn1 Cl1 88.38(7) . 1_455 ? N1 Mn1 Cl1 91.62(7) 2_556 1_455 ? Cl1 Mn1 Cl1 180.0 2_656 1_455 ? N1 Mn1 Cl1 84.65(6) . . ? N1 Mn1 Cl1 95.35(6) 2_556 . ? Cl1 Mn1 Cl1 85.98(3) 2_656 . ? Cl1 Mn1 Cl1 94.02(3) 1_455 . ? N1 Mn1 Cl1 95.35(6) . 2_556 ? N1 Mn1 Cl1 84.65(6) 2_556 2_556 ? Cl1 Mn1 Cl1 94.02(3) 2_656 2_556 ? Cl1 Mn1 Cl1 85.98(3) 1_455 2_556 ? Cl1 Mn1 Cl1 180.00(3) . 2_556 ? N2 Se1 N1 92.93(12) . . ? Mn1 Cl1 Mn1 94.02(3) 1_655 . ? C5 N1 Se1 107.8(2) . . ? C5 N1 Mn1 135.5(2) . . ? Se1 N1 Mn1 116.64(12) . . ? C6 N2 Se1 108.1(2) . . ? C2 C1 C6 118.9(3) . . ? C2 C1 H1 120.6 . . ? C6 C1 H1 120.6 . . ? C1 C2 C3 121.3(3) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C4 C3 C2 122.4(3) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C3 C4 C5 118.8(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 C4 126.4(3) . . ? N1 C5 C6 115.0(3) . . ? C4 C5 C6 118.7(3) . . ? N2 C6 C1 123.9(3) . . ? N2 C6 C5 116.2(3) . . ? C1 C6 C5 119.9(3) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.33 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.548 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.110 _iucr_refine_instruction_details ; REM TRY 2 FINAL CC 71.92 TIME 0 SECS REM Fragments: 9 REM TITL BSeDMn_0m in P-1 CELL 0.71073 3.7203 9.2784 10.7695 80.055 81.254 83.353 ZERR 1.00 0.0010 0.0024 0.0028 0.004 0.004 0.004 LATT 1 SFAC C H N O S CL MN SE UNIT 10 16 2 2 2 2 1 1 TEMP 100.00 SIZE 0.060 0.100 0.270 L.S. 4 BOND FMAP 2 PLAN 2 WGHT 0.036000 EXTI 0.009711 FVAR 0.25645 MN1 7 0.000000 0.000000 0.500000 10.50000 0.01208 0.01282 = 0.01185 -0.00363 0.00012 -0.00183 SE1 8 0.339012 0.010585 0.175057 11.00000 0.01591 0.01452 = 0.01136 -0.00315 0.00039 -0.00276 CL1 6 0.498910 0.166237 0.397665 11.00000 0.01499 0.01204 = 0.01491 -0.00234 -0.00035 -0.00298 N1 3 0.139206 -0.104401 0.315243 11.00000 0.01255 0.01584 = 0.01040 -0.00415 0.00054 -0.00141 N2 3 0.351116 -0.127031 0.077382 11.00000 0.01595 0.02019 = 0.01201 -0.00589 -0.00080 -0.00013 C1 1 0.195725 -0.378844 0.104022 11.00000 0.02294 0.01949 = 0.02003 -0.00878 -0.00483 0.00003 H1 2 0.292354 -0.384494 0.009188 11.00000 0.04192 C2 1 0.054157 -0.491412 0.185916 11.00000 0.02289 0.01411 = 0.02848 -0.00985 -0.00722 -0.00119 H2 2 0.030749 -0.583856 0.157943 11.00000 0.01653 C3 1 -0.077555 -0.477917 0.314821 11.00000 0.01778 0.01489 = 0.02606 0.00001 -0.00602 -0.00179 H3 2 -0.167259 -0.557133 0.360220 11.00000 0.02764 C4 1 -0.059107 -0.354342 0.363581 11.00000 0.01832 0.01498 = 0.01469 -0.00133 -0.00156 -0.00056 H4 2 -0.138152 -0.345287 0.449292 11.00000 0.03101 C5 1 0.092497 -0.232146 0.282028 11.00000 0.00914 0.01733 = 0.01513 -0.00581 -0.00292 0.00310 C6 1 0.216904 -0.244534 0.149340 11.00000 0.01467 0.01520 = 0.01315 -0.00370 -0.00364 0.00241 HKLF 4 REM BSeDMn_0m in P-1 REM R1 = 0.0254 for 1267 Fo > 4sig(Fo) and 0.0310 for all 1447 data REM 114 parameters refined using 0 restraints END WGHT 0.0332 0.0000 REM Highest difference peak 0.542, deepest hole -0.441, 1-sigma level 0.110 Q1 1 0.5618 0.0268 0.1750 11.00000 0.05 0.54 Q2 1 0.2357 -0.2431 0.2269 11.00000 0.05 0.47 ; _database_code_depnum_ccdc_archive 'CCDC 932445'