# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_safin273_2 _database_code_depnum_ccdc_archive 'CCDC 911407' #TrackingRef 'web_deposit_cif_file_1_DamirSafin_1355235524.[Co2L2].cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H72 Co2 N8 O8 P4 S8' _chemical_formula_sum 'C36 H72 Co2 N8 O8 P4 S8' _chemical_formula_weight 1243.24 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' Co Co 0.3494 0.9721 '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' P P 0.1023 0.0942 '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 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 10.2715(14) _cell_length_b 10.7122(13) _cell_length_c 14.188(3) _cell_angle_alpha 91.162(13) _cell_angle_beta 92.255(14) _cell_angle_gamma 101.349(11) _cell_volume 1528.8(4) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1803 _cell_measurement_theta_min 2.3763 _cell_measurement_theta_max 22.4127 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 650 _exptl_absorpt_coefficient_mu 0.968 _exptl_absorpt_correction_T_min 0.94981 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; In the crystal structure the isopropyl groups show high termal motion. This is on on hand related to the measurement conditions (room temperature) as well to the dynamic nature of these groups (free rotation around the ether bond. Distance restraints were applied to the CH-CH3 bonds in the isopropyl groups as the free rotation of these isopropyl groups caused a shortening of the bond lengths. No constraints were applied to the thermal ellipsoids. ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku UltraX 18 rotating anode' _diffrn_radiation_monochromator 'Xenocs Fox3D mirror' _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '140 images, \D\F 1.2\% ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6947 _diffrn_reflns_av_R_equivalents 0.0735 _diffrn_reflns_av_sigmaI/netI 0.0954 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 22.46 _reflns_number_total 3771 _reflns_number_gt 2479 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0577P)^2^+1.3040P] 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 3771 _refine_ls_number_parameters 306 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0989 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1535 _refine_ls_wR_factor_gt 0.1326 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.996 _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 Co1 Co 0.06660(6) -0.21863(6) 0.24647(4) 0.0595(2) Uani 1 1 d . . . S2 S 0.27661(13) -0.17233(14) 0.18770(11) 0.0823(5) Uani 1 1 d . . . P3 P 0.32330(12) 0.01207(14) 0.22586(9) 0.0628(4) Uani 1 1 d . . . O4 O 0.4768(3) 0.0466(4) 0.2417(3) 0.0955(14) Uani 1 1 d . . . C5 C 0.5430(5) 0.0100(6) 0.3221(5) 0.139(3) Uani 1 1 d D . . H5 H 0.4772 -0.0456 0.3585 0.167 Uiso 1 1 calc R . . C6 C 0.6083(8) 0.1169(8) 0.3841(6) 0.237(5) Uani 1 1 d D . . H6A H 0.6714 0.1743 0.3494 0.355 Uiso 1 1 calc R . . H6B H 0.6534 0.0854 0.4363 0.355 Uiso 1 1 calc R . . H6C H 0.5428 0.1611 0.4073 0.355 Uiso 1 1 calc R . . C7 C 0.6390(7) -0.0679(9) 0.2867(6) 0.229(5) Uani 1 1 d D . . H7A H 0.7085 -0.0138 0.2549 0.343 Uiso 1 1 calc R . . H7B H 0.5928 -0.1334 0.2435 0.343 Uiso 1 1 calc R . . H7C H 0.6767 -0.1061 0.3390 0.343 Uiso 1 1 calc R . . O8 O 0.2984(3) 0.0992(3) 0.1430(2) 0.0766(11) Uani 1 1 d . . . C9 C 0.3189(5) 0.0702(6) 0.0441(4) 0.109(2) Uani 1 1 d D . . H9 H 0.3485 -0.0111 0.0385 0.131 Uiso 1 1 calc R . . C10 C 0.1872(7) 0.0612(9) -0.0065(5) 0.187(4) Uani 1 1 d D . . H10A H 0.1656 0.1443 -0.0090 0.280 Uiso 1 1 calc R . . H10B H 0.1203 0.0054 0.0264 0.280 Uiso 1 1 calc R . . H10C H 0.1909 0.0280 -0.0695 0.280 Uiso 1 1 calc R . . C11 C 0.4221(8) 0.1746(8) 0.0122(6) 0.206(4) Uani 1 1 d D . . H11A H 0.3895 0.2527 0.0134 0.308 Uiso 1 1 calc R . . H11B H 0.4441 0.1558 -0.0510 0.308 Uiso 1 1 calc R . . H11C H 0.5001 0.1835 0.0534 0.308 Uiso 1 1 calc R . . N12 N 0.2642(3) 0.0645(4) 0.3166(3) 0.0622(12) Uani 1 1 d . . . C13 C 0.1394(4) 0.0649(4) 0.3356(3) 0.0567(13) Uani 1 1 d . . . S14 S 0.00246(11) -0.03006(12) 0.27550(9) 0.0646(4) Uani 1 1 d . . . N15 N 0.1154(3) 0.1427(4) 0.4040(3) 0.0591(11) Uani 1 1 d . . . C16 C 0.2230(4) 0.2256(4) 0.4587(3) 0.0650(15) Uani 1 1 d . . . H16A H 0.3064 0.2250 0.4290 0.078 Uiso 1 1 calc R . . H16B H 0.2294 0.1929 0.5216 0.078 Uiso 1 1 calc R . . C17 C 0.2011(4) 0.3613(5) 0.4659(3) 0.0647(15) Uani 1 1 d . . . H17A H 0.2698 0.4122 0.5071 0.078 Uiso 1 1 calc R . . H17B H 0.2058 0.3985 0.4040 0.078 Uiso 1 1 calc R . . N18 N 0.0714(3) 0.3609(4) 0.5032(3) 0.0586(11) Uani 1 1 d . . . C19 C -0.0329(4) 0.2875(4) 0.4415(3) 0.0622(14) Uani 1 1 d . . . H19A H -0.0278 0.3218 0.3788 0.075 Uiso 1 1 calc R . . H19B H -0.1191 0.2925 0.4652 0.075 Uiso 1 1 calc R . . C20 C -0.0167(4) 0.1509(4) 0.4375(3) 0.0607(14) Uani 1 1 d . . . H20A H -0.0269 0.1155 0.4998 0.073 Uiso 1 1 calc R . . H20B H -0.0851 0.1016 0.3952 0.073 Uiso 1 1 calc R . . C21 C 0.0584(5) 0.3883(4) 0.5953(3) 0.0584(13) Uani 1 1 d . . . S22 S -0.10288(12) 0.35423(13) 0.63809(9) 0.0648(4) Uani 1 1 d . . . N23 N 0.1648(4) 0.4373(4) 0.6460(3) 0.0650(12) Uani 1 1 d . . . P24 P 0.17421(13) 0.46898(13) 0.75678(9) 0.0634(4) Uani 1 1 d . . . S25 S 0.12008(14) 0.32350(13) 0.84137(10) 0.0746(4) Uani 1 1 d . . . O26 O 0.1021(3) 0.5822(3) 0.7769(2) 0.0740(10) Uani 1 1 d . . . C27 C 0.0514(5) 0.6126(5) 0.8679(4) 0.106(2) Uani 1 1 d D . . H27 H 0.0376 0.5372 0.9070 0.127 Uiso 1 1 calc R . . C28 C -0.0767(7) 0.6533(9) 0.8489(6) 0.223(4) Uani 1 1 d D . . H28A H -0.0600 0.7403 0.8298 0.335 Uiso 1 1 calc R . . H28B H -0.1263 0.6460 0.9052 0.335 Uiso 1 1 calc R . . H28C H -0.1268 0.6001 0.7995 0.335 Uiso 1 1 calc R . . C29 C 0.1482(9) 0.7153(9) 0.9152(6) 0.301(6) Uani 1 1 d D . . H29A H 0.2115 0.6796 0.9521 0.452 Uiso 1 1 calc R . . H29B H 0.1031 0.7640 0.9557 0.452 Uiso 1 1 calc R . . H29C H 0.1935 0.7697 0.8688 0.452 Uiso 1 1 calc R . . O30 O 0.3228(3) 0.5308(3) 0.7803(2) 0.0817(12) Uani 1 1 d . . . C31 C 0.4295(5) 0.4630(6) 0.7652(4) 0.112(2) Uani 1 1 d D . . H31 H 0.3908 0.3743 0.7471 0.134 Uiso 1 1 calc R . . C32 C 0.5108(7) 0.5216(10) 0.6879(5) 0.223(5) Uani 1 1 d D . . H32A H 0.5742 0.5942 0.7123 0.334 Uiso 1 1 calc R . . H32B H 0.4541 0.5479 0.6400 0.334 Uiso 1 1 calc R . . H32C H 0.5569 0.4605 0.6612 0.334 Uiso 1 1 calc R . . C33 C 0.5091(8) 0.4655(9) 0.8542(5) 0.195(4) Uani 1 1 d D . . H33A H 0.5572 0.5506 0.8680 0.292 Uiso 1 1 calc R . . H33B H 0.5706 0.4093 0.8481 0.292 Uiso 1 1 calc R . . H33C H 0.4512 0.4382 0.9045 0.292 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 Co1 0.0700(4) 0.0502(4) 0.0605(4) 0.0066(3) 0.0125(3) 0.0145(3) S2 0.0858(8) 0.0651(9) 0.1019(10) 0.0056(8) 0.0389(7) 0.0225(7) P3 0.0577(7) 0.0704(9) 0.0617(8) 0.0015(7) 0.0086(6) 0.0150(6) O4 0.0585(19) 0.135(3) 0.091(3) -0.009(2) 0.0038(18) 0.017(2) C5 0.066(4) 0.234(9) 0.124(6) -0.025(6) 0.004(4) 0.046(5) C6 0.125(6) 0.349(14) 0.229(9) -0.144(9) -0.070(6) 0.062(8) C7 0.167(6) 0.325(11) 0.233(11) -0.023(9) -0.046(7) 0.159(6) O8 0.095(2) 0.072(2) 0.067(2) 0.0068(18) 0.0132(18) 0.0257(18) C9 0.158(5) 0.114(5) 0.074(4) 0.023(4) 0.038(4) 0.062(4) C10 0.272(9) 0.173(8) 0.121(6) 0.015(6) -0.067(7) 0.071(7) C11 0.261(8) 0.182(9) 0.178(7) 0.053(7) 0.137(6) 0.026(8) N12 0.051(2) 0.072(3) 0.065(2) -0.009(2) 0.0070(18) 0.0158(19) C13 0.069(3) 0.051(3) 0.054(3) 0.004(2) 0.003(2) 0.021(2) S14 0.0575(7) 0.0596(8) 0.0782(9) -0.0093(7) -0.0005(6) 0.0174(6) N15 0.052(2) 0.058(2) 0.066(2) -0.012(2) 0.0025(18) 0.0071(19) C16 0.060(3) 0.069(3) 0.069(3) -0.003(3) 0.005(2) 0.018(2) C17 0.071(3) 0.062(3) 0.060(3) -0.005(3) 0.020(2) 0.006(3) N18 0.065(2) 0.054(2) 0.059(2) 0.005(2) 0.0137(19) 0.0161(18) C19 0.069(3) 0.074(3) 0.050(3) 0.006(3) -0.002(2) 0.031(2) C20 0.059(3) 0.060(3) 0.067(3) -0.001(3) 0.011(2) 0.020(2) C21 0.087(3) 0.043(3) 0.052(3) 0.010(2) 0.017(2) 0.025(2) S22 0.0737(7) 0.0667(8) 0.0594(8) 0.0106(7) 0.0132(6) 0.0239(6) N23 0.072(2) 0.060(3) 0.058(2) -0.003(2) 0.011(2) 0.001(2) P24 0.0785(8) 0.0533(8) 0.0565(8) 0.0007(7) 0.0052(7) 0.0083(7) S25 0.0947(9) 0.0589(9) 0.0675(9) 0.0104(7) -0.0028(7) 0.0089(7) O26 0.109(2) 0.059(2) 0.059(2) -0.0025(17) 0.0160(18) 0.0246(18) C27 0.190(5) 0.073(4) 0.067(4) -0.002(3) 0.028(4) 0.050(4) C28 0.232(7) 0.312(10) 0.172(8) -0.074(7) 0.029(6) 0.171(7) C29 0.239(11) 0.396(13) 0.231(8) -0.241(8) 0.022(8) -0.009(11) O30 0.080(2) 0.074(2) 0.085(3) -0.008(2) 0.0003(19) 0.001(2) C31 0.086(4) 0.096(5) 0.144(6) -0.025(4) 0.005(4) -0.002(4) C32 0.135(6) 0.345(15) 0.197(9) 0.034(9) 0.085(6) 0.054(8) C33 0.177(7) 0.235(11) 0.184(9) 0.030(8) -0.044(7) 0.078(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 S22 2.2787(15) 2_556 ? Co1 S14 2.2794(15) . ? Co1 S2 2.3090(15) . ? Co1 S25 2.3237(15) 2_556 ? S2 P3 1.997(2) . ? P3 O4 1.553(3) . ? P3 O8 1.560(4) . ? P3 N12 1.583(4) . ? O4 C5 1.406(7) . ? C5 C6 1.465(7) . ? C5 C7 1.505(7) . ? C5 H5 0.9800 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? O8 C9 1.462(6) . ? C9 C11 1.474(7) . ? C9 C10 1.492(7) . ? C9 H9 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N12 C13 1.321(5) . ? C13 N15 1.329(6) . ? C13 S14 1.746(4) . ? N15 C16 1.460(5) . ? N15 C20 1.473(5) . ? C16 C17 1.517(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N18 1.452(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? N18 C21 1.350(5) . ? N18 C19 1.449(5) . ? C19 C20 1.504(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 N23 1.297(5) . ? C21 S22 1.760(5) . ? S22 Co1 2.2787(15) 2_556 ? N23 P24 1.597(4) . ? P24 O30 1.560(3) . ? P24 O26 1.567(4) . ? P24 S25 1.9914(19) . ? S25 Co1 2.3237(15) 2_556 ? O26 C27 1.465(6) . ? C27 C29 1.461(7) . ? C27 C28 1.482(7) . ? C27 H27 0.9800 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? O30 C31 1.449(7) . ? C31 C33 1.474(7) . ? C31 C32 1.479(7) . ? C31 H31 0.9800 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 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 S22 Co1 S14 123.42(6) 2_556 . ? S22 Co1 S2 99.52(6) 2_556 . ? S14 Co1 S2 107.50(5) . . ? S22 Co1 S25 105.86(5) 2_556 2_556 ? S14 Co1 S25 99.16(5) . 2_556 ? S2 Co1 S25 123.40(6) . 2_556 ? P3 S2 Co1 98.42(7) . . ? O4 P3 O8 102.2(2) . . ? O4 P3 N12 106.0(2) . . ? O8 P3 N12 107.0(2) . . ? O4 P3 S2 107.06(18) . . ? O8 P3 S2 111.88(15) . . ? N12 P3 S2 120.99(16) . . ? C5 O4 P3 122.5(3) . . ? O4 C5 C6 114.0(6) . . ? O4 C5 C7 106.4(5) . . ? C6 C5 C7 112.5(6) . . ? O4 C5 H5 107.9 . . ? C6 C5 H5 107.9 . . ? C7 C5 H5 107.9 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 O8 P3 123.7(3) . . ? O8 C9 C11 106.7(5) . . ? O8 C9 C10 105.9(5) . . ? C11 C9 C10 113.5(6) . . ? O8 C9 H9 110.2 . . ? C11 C9 H9 110.2 . . ? C10 C9 H9 110.2 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 N12 P3 129.8(3) . . ? N12 C13 N15 118.6(4) . . ? N12 C13 S14 124.0(3) . . ? N15 C13 S14 117.4(3) . . ? C13 S14 Co1 104.66(16) . . ? C13 N15 C16 121.6(4) . . ? C13 N15 C20 125.8(4) . . ? C16 N15 C20 112.5(4) . . ? N15 C16 C17 111.8(4) . . ? N15 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? N15 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? N18 C17 C16 109.1(4) . . ? N18 C17 H17A 109.9 . . ? C16 C17 H17A 109.9 . . ? N18 C17 H17B 109.9 . . ? C16 C17 H17B 109.9 . . ? H17A C17 H17B 108.3 . . ? C21 N18 C19 124.7(4) . . ? C21 N18 C17 121.1(4) . . ? C19 N18 C17 110.7(4) . . ? N18 C19 C20 109.2(4) . . ? N18 C19 H19A 109.8 . . ? C20 C19 H19A 109.8 . . ? N18 C19 H19B 109.8 . . ? C20 C19 H19B 109.8 . . ? H19A C19 H19B 108.3 . . ? N15 C20 C19 110.2(4) . . ? N15 C20 H20A 109.6 . . ? C19 C20 H20A 109.6 . . ? N15 C20 H20B 109.6 . . ? C19 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? N23 C21 N18 118.2(4) . . ? N23 C21 S22 124.6(3) . . ? N18 C21 S22 117.2(3) . . ? C21 S22 Co1 98.43(16) . 2_556 ? C21 N23 P24 126.8(3) . . ? O30 P24 O26 102.24(19) . . ? O30 P24 N23 105.5(2) . . ? O26 P24 N23 109.1(2) . . ? O30 P24 S25 108.99(16) . . ? O26 P24 S25 112.81(14) . . ? N23 P24 S25 116.98(16) . . ? P24 S25 Co1 98.21(7) . 2_556 ? C27 O26 P24 125.4(3) . . ? C29 C27 O26 108.7(5) . . ? C29 C27 C28 110.7(6) . . ? O26 C27 C28 107.7(5) . . ? C29 C27 H27 109.9 . . ? O26 C27 H27 109.9 . . ? C28 C27 H27 109.9 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C31 O30 P24 122.1(3) . . ? O30 C31 C33 108.8(5) . . ? O30 C31 C32 109.6(6) . . ? C33 C31 C32 111.9(6) . . ? O30 C31 H31 108.8 . . ? C33 C31 H31 108.8 . . ? C32 C31 H31 108.8 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 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 S22 Co1 S2 P3 -113.78(7) 2_556 . . . ? S14 Co1 S2 P3 15.89(9) . . . . ? S25 Co1 S2 P3 129.96(8) 2_556 . . . ? Co1 S2 P3 O4 151.07(16) . . . . ? Co1 S2 P3 O8 -97.70(15) . . . . ? Co1 S2 P3 N12 29.74(19) . . . . ? O8 P3 O4 C5 167.0(4) . . . . ? N12 P3 O4 C5 55.2(5) . . . . ? S2 P3 O4 C5 -75.2(4) . . . . ? P3 O4 C5 C6 -113.7(6) . . . . ? P3 O4 C5 C7 121.7(5) . . . . ? O4 P3 O8 C9 79.2(4) . . . . ? N12 P3 O8 C9 -169.7(3) . . . . ? S2 P3 O8 C9 -35.0(4) . . . . ? P3 O8 C9 C11 -118.7(5) . . . . ? P3 O8 C9 C10 120.0(5) . . . . ? O4 P3 N12 C13 176.3(4) . . . . ? O8 P3 N12 C13 67.8(5) . . . . ? S2 P3 N12 C13 -61.9(5) . . . . ? P3 N12 C13 N15 -162.4(4) . . . . ? P3 N12 C13 S14 17.1(6) . . . . ? N12 C13 S14 Co1 37.4(4) . . . . ? N15 C13 S14 Co1 -143.2(3) . . . . ? S22 Co1 S14 C13 67.81(17) 2_556 . . . ? S2 Co1 S14 C13 -46.75(17) . . . . ? S25 Co1 S14 C13 -176.21(16) 2_556 . . . ? N12 C13 N15 C16 -0.7(7) . . . . ? S14 C13 N15 C16 179.8(3) . . . . ? N12 C13 N15 C20 -176.8(4) . . . . ? S14 C13 N15 C20 3.7(6) . . . . ? C13 N15 C16 C17 131.8(4) . . . . ? C20 N15 C16 C17 -51.7(5) . . . . ? N15 C16 C17 N18 54.4(5) . . . . ? C16 C17 N18 C21 99.3(5) . . . . ? C16 C17 N18 C19 -60.7(5) . . . . ? C21 N18 C19 C20 -96.0(5) . . . . ? C17 N18 C19 C20 63.1(5) . . . . ? C13 N15 C20 C19 -130.4(5) . . . . ? C16 N15 C20 C19 53.2(5) . . . . ? N18 C19 C20 N15 -58.0(5) . . . . ? C19 N18 C21 N23 169.4(4) . . . . ? C17 N18 C21 N23 12.4(6) . . . . ? C19 N18 C21 S22 -10.5(6) . . . . ? C17 N18 C21 S22 -167.5(3) . . . . ? N23 C21 S22 Co1 -58.4(4) . . . 2_556 ? N18 C21 S22 Co1 121.5(3) . . . 2_556 ? N18 C21 N23 P24 -175.9(3) . . . . ? S22 C21 N23 P24 4.0(7) . . . . ? C21 N23 P24 O30 -177.8(4) . . . . ? C21 N23 P24 O26 -68.7(5) . . . . ? C21 N23 P24 S25 60.9(5) . . . . ? O30 P24 S25 Co1 -160.97(15) . . . 2_556 ? O26 P24 S25 Co1 86.20(15) . . . 2_556 ? N23 P24 S25 Co1 -41.54(19) . . . 2_556 ? O30 P24 O26 C27 -89.6(4) . . . . ? N23 P24 O26 C27 159.1(3) . . . . ? S25 P24 O26 C27 27.3(4) . . . . ? P24 O26 C27 C29 98.8(6) . . . . ? P24 O26 C27 C28 -141.2(5) . . . . ? O26 P24 O30 C31 -175.4(4) . . . . ? N23 P24 O30 C31 -61.3(4) . . . . ? S25 P24 O30 C31 65.0(4) . . . . ? P24 O30 C31 C33 -125.6(5) . . . . ? P24 O30 C31 C32 111.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 22.46 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.439 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.065 data_safin262-1 _database_code_depnum_ccdc_archive 'CCDC 911408' #TrackingRef 'web_deposit_cif_file_0_DamirSafin_1355235524.1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H36 N2 O4 P2 S2' _chemical_formula_sum 'C16 H36 N2 O4 P2 S2' _chemical_formula_weight 446.53 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' P P 0.1023 0.0942 '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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 17.7793(5) _cell_length_b 7.9981(2) _cell_length_c 17.2729(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.163(3) _cell_angle_gamma 90.00 _cell_volume 2455.70(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5325 _cell_measurement_theta_min 2.2869 _cell_measurement_theta_max 29.8405 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.368 _exptl_absorpt_correction_T_min 0.97985 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku UltraX 18 rotating anode' _diffrn_radiation_monochromator 'Xenocs Fox3D mirror' _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '180 images, \D\F 1.0\% ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11873 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 29.91 _reflns_number_total 3286 _reflns_number_gt 2639 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0499P)^2^+2.3682P] 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 3286 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 S1 S 0.15882(3) 0.35650(6) 0.22070(3) 0.02982(13) Uani 1 1 d . . . P2 P 0.13145(2) 0.24303(5) 0.12612(2) 0.02115(12) Uani 1 1 d . . . O3 O 0.11012(7) 0.05218(15) 0.13504(7) 0.0254(3) Uani 1 1 d . . . C4 C 0.15950(11) -0.0602(2) 0.18067(11) 0.0288(4) Uani 1 1 d . . . H4 H 0.2040 0.0041 0.2008 0.035 Uiso 1 1 calc R . . C5 C 0.11557(15) -0.1249(3) 0.24753(14) 0.0480(6) Uani 1 1 d . . . H5A H 0.1013 -0.0314 0.2808 0.072 Uiso 1 1 calc R . . H5B H 0.1466 -0.2040 0.2775 0.072 Uiso 1 1 calc R . . H5C H 0.0702 -0.1817 0.2280 0.072 Uiso 1 1 calc R . . C6 C 0.18593(14) -0.1972(3) 0.12797(13) 0.0418(5) Uani 1 1 d . . . H6A H 0.1424 -0.2594 0.1075 0.063 Uiso 1 1 calc R . . H6B H 0.2191 -0.2733 0.1571 0.063 Uiso 1 1 calc R . . H6C H 0.2135 -0.1481 0.0850 0.063 Uiso 1 1 calc R . . O7 O 0.05929(7) 0.31120(16) 0.08157(7) 0.0259(3) Uani 1 1 d . . . C8 C -0.01345(10) 0.3254(2) 0.11990(11) 0.0281(4) Uani 1 1 d . . . H8 H -0.0078 0.2871 0.1748 0.034 Uiso 1 1 calc R . . C9 C -0.06724(14) 0.2124(4) 0.07725(17) 0.0643(8) Uani 1 1 d . . . H9A H -0.0737 0.2514 0.0237 0.096 Uiso 1 1 calc R . . H9B H -0.1159 0.2137 0.1028 0.096 Uiso 1 1 calc R . . H9C H -0.0472 0.0982 0.0773 0.096 Uiso 1 1 calc R . . C10 C -0.03511(16) 0.5064(3) 0.11846(18) 0.0611(8) Uani 1 1 d . . . H10A H 0.0029 0.5718 0.1471 0.092 Uiso 1 1 calc R . . H10B H -0.0841 0.5203 0.1427 0.092 Uiso 1 1 calc R . . H10C H -0.0383 0.5454 0.0647 0.092 Uiso 1 1 calc R . . N11 N 0.19717(8) 0.24614(17) 0.05988(8) 0.0222(3) Uani 1 1 d . . . C12 C 0.18023(10) 0.1660(2) -0.01547(10) 0.0263(4) Uani 1 1 d . . . H12A H 0.1537 0.2461 -0.0501 0.032 Uiso 1 1 calc R . . H12B H 0.1470 0.0683 -0.0079 0.032 Uiso 1 1 calc R . . C13 C 0.25268(10) 0.1101(2) -0.05210(11) 0.0251(3) Uani 1 1 d . . . H13A H 0.2773 0.0235 -0.0194 0.030 Uiso 1 1 calc R . . H13B H 0.2416 0.0610 -0.1037 0.030 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 S1 0.0315(3) 0.0325(2) 0.0256(2) -0.00569(17) 0.00313(17) -0.00252(18) P2 0.0185(2) 0.0222(2) 0.0229(2) -0.00100(15) 0.00300(15) 0.00097(15) O3 0.0228(6) 0.0245(6) 0.0289(6) 0.0015(5) -0.0001(5) -0.0015(5) C4 0.0314(9) 0.0232(9) 0.0316(10) 0.0033(7) -0.0022(7) 0.0013(7) C5 0.0607(16) 0.0448(13) 0.0390(13) 0.0116(9) 0.0125(11) 0.0032(11) C6 0.0554(14) 0.0310(10) 0.0393(12) 0.0027(8) 0.0047(10) 0.0117(10) O7 0.0204(6) 0.0333(7) 0.0242(6) 0.0029(5) 0.0046(5) 0.0052(5) C8 0.0196(8) 0.0386(10) 0.0263(9) 0.0040(7) 0.0053(6) 0.0039(7) C9 0.0301(12) 0.109(2) 0.0535(16) -0.0214(15) 0.0035(11) -0.0190(14) C10 0.0602(17) 0.0478(14) 0.077(2) 0.0214(12) 0.0405(14) 0.0282(12) N11 0.0203(7) 0.0216(7) 0.0249(7) -0.0057(5) 0.0052(5) -0.0026(5) C12 0.0226(8) 0.0302(9) 0.0261(9) -0.0075(6) 0.0024(6) -0.0051(7) C13 0.0255(8) 0.0210(8) 0.0290(9) -0.0060(6) 0.0067(6) -0.0035(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 S1 P2 1.9228(6) . ? P2 O7 1.5796(13) . ? P2 O3 1.5811(13) . ? P2 N11 1.6520(15) . ? O3 C4 1.474(2) . ? C4 C5 1.499(3) . ? C4 C6 1.506(3) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? O7 C8 1.469(2) . ? C8 C10 1.498(3) . ? C8 C9 1.498(3) . ? C8 H8 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? N11 C13 1.463(2) 7 ? N11 C12 1.476(2) . ? C12 C13 1.514(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N11 1.463(2) 7 ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 P2 O3 100.76(7) . . ? O7 P2 N11 103.67(7) . . ? O3 P2 N11 104.86(7) . . ? O7 P2 S1 116.10(5) . . ? O3 P2 S1 115.46(5) . . ? N11 P2 S1 114.27(6) . . ? C4 O3 P2 119.97(11) . . ? O3 C4 C5 107.97(17) . . ? O3 C4 C6 108.08(15) . . ? C5 C4 C6 112.84(17) . . ? O3 C4 H4 109.3 . . ? C5 C4 H4 109.3 . . ? C6 C4 H4 109.3 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 O7 P2 121.40(11) . . ? O7 C8 C10 107.19(16) . . ? O7 C8 C9 106.91(17) . . ? C10 C8 C9 114.4(2) . . ? O7 C8 H8 109.4 . . ? C10 C8 H8 109.4 . . ? C9 C8 H8 109.4 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C13 N11 C12 111.98(13) 7 . ? C13 N11 P2 121.09(11) 7 . ? C12 N11 P2 118.00(11) . . ? N11 C12 C13 109.67(14) . . ? N11 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? N11 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? N11 C13 C12 109.36(13) 7 . ? N11 C13 H13A 109.8 7 . ? C12 C13 H13A 109.8 . . ? N11 C13 H13B 109.8 7 . ? C12 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O7 P2 O3 C4 -174.33(12) . . . . ? N11 P2 O3 C4 78.25(14) . . . . ? S1 P2 O3 C4 -48.43(14) . . . . ? P2 O3 C4 C5 117.77(16) . . . . ? P2 O3 C4 C6 -119.87(15) . . . . ? O3 P2 O7 C8 70.38(14) . . . . ? N11 P2 O7 C8 178.73(13) . . . . ? S1 P2 O7 C8 -55.10(14) . . . . ? P2 O7 C8 C10 118.86(19) . . . . ? P2 O7 C8 C9 -118.02(19) . . . . ? O7 P2 N11 C13 93.61(14) . . . 7 ? O3 P2 N11 C13 -161.12(13) . . . 7 ? S1 P2 N11 C13 -33.71(15) . . . 7 ? O7 P2 N11 C12 -51.04(14) . . . . ? O3 P2 N11 C12 54.23(14) . . . . ? S1 P2 N11 C12 -178.36(11) . . . . ? C13 N11 C12 C13 58.4(2) 7 . . . ? P2 N11 C12 C13 -153.90(12) . . . . ? N11 C12 C13 N11 -56.8(2) . . . 7 ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.370 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.064 data_safin262 _database_code_depnum_ccdc_archive 'CCDC 911409' #TrackingRef 'web_deposit_cif_file_2_DamirSafin_1355235524.2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H12 N2, 2(C2 H3 O2)' _chemical_formula_sum 'C8 H18 N2 O4' _chemical_formula_weight 206.24 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' _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 5.7855(3) _cell_length_b 7.0039(11) _cell_length_c 7.4459(11) _cell_angle_alpha 117.795(16) _cell_angle_beta 100.317(9) _cell_angle_gamma 90.118(9) _cell_volume 261.32(6) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2246 _cell_measurement_theta_min 3.1525 _cell_measurement_theta_max 25.6183 _exptl_crystal_description plate _exptl_crystal_colour colour _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 112 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_min 0.97985 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; Twinning, HKLF 5 file created with platon TWINROTMAT ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku UltraX 18 rotating anode' _diffrn_radiation_monochromator 'Xenocs Fox3D mirror' _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '180 images, \D\F 1.5\% ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 913 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.70 _reflns_number_total 913 _reflns_number_gt 898 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0217P)^2^+0.2673P] 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 913 _refine_ls_number_parameters 66 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.194 _refine_ls_restrained_S_all 1.194 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0301(4) 0.3477(4) 0.6762(4) 0.0246(5) Uani 1 1 d . . . H1A H -0.0453 0.4966 0.7000 0.037 Uiso 1 1 calc R . . H1B H 0.0548 0.3504 0.8038 0.037 Uiso 1 1 calc R . . H1C H -0.1875 0.2705 0.6357 0.037 Uiso 1 1 calc R . . C2 C 0.1054(4) 0.2327(4) 0.5047(3) 0.0173(5) Uani 1 1 d . . . O3 O 0.3266(3) 0.2483(3) 0.5564(2) 0.0248(4) Uani 1 1 d . . . O4 O -0.0071(3) 0.1313(3) 0.3204(2) 0.0238(4) Uani 1 1 d . . . C5 C 0.4344(5) -0.1501(4) 0.0692(4) 0.0213(5) Uani 1 1 d . . . H5A H 0.2600 -0.1671 0.0278 0.026 Uiso 1 1 calc R . . H5B H 0.4803 -0.2417 0.1359 0.026 Uiso 1 1 calc R . . N6 N 0.5176(3) 0.0798(3) 0.2174(3) 0.0188(5) Uani 1 1 d . . . H6A H 0.6786 0.0931 0.2619 0.023 Uiso 1 1 calc R . . H6B H 0.4493 0.1237 0.3312 0.023 Uiso 1 1 calc R . . C7 C 0.4576(5) 0.2219(4) 0.1208(4) 0.0208(5) Uani 1 1 d . . . H7A H 0.5179 0.3740 0.2223 0.025 Uiso 1 1 calc R . . H7B H 0.2839 0.2151 0.0806 0.025 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 C1 0.0242(14) 0.0250(13) 0.0241(12) 0.0099(11) 0.0085(10) 0.0038(11) C2 0.0184(12) 0.0157(10) 0.0191(11) 0.0095(9) 0.0033(8) 0.0009(9) O3 0.0167(9) 0.0354(10) 0.0181(8) 0.0097(8) 0.0025(6) 0.0013(8) O4 0.0168(9) 0.0310(9) 0.0187(8) 0.0086(8) 0.0016(6) 0.0001(7) C5 0.0194(13) 0.0240(12) 0.0215(12) 0.0119(10) 0.0034(9) 0.0010(10) N6 0.0143(10) 0.0261(11) 0.0139(8) 0.0078(8) 0.0027(7) 0.0019(8) C7 0.0191(14) 0.0180(11) 0.0215(12) 0.0062(10) 0.0041(10) 0.0038(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 C1 C2 1.515(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O4 1.257(3) . ? C2 O3 1.258(3) . ? C5 N6 1.480(3) . ? C5 C7 1.516(3) 2_655 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? N6 C7 1.486(3) . ? N6 H6A 0.9200 . ? N6 H6B 0.9200 . ? C7 C5 1.516(3) 2_655 ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O4 C2 O3 123.8(2) . . ? O4 C2 C1 118.9(2) . . ? O3 C2 C1 117.31(19) . . ? N6 C5 C7 109.6(2) . 2_655 ? N6 C5 H5A 109.8 . . ? C7 C5 H5A 109.8 2_655 . ? N6 C5 H5B 109.8 . . ? C7 C5 H5B 109.8 2_655 . ? H5A C5 H5B 108.2 . . ? C5 N6 C7 111.35(17) . . ? C5 N6 H6A 109.4 . . ? C7 N6 H6A 109.4 . . ? C5 N6 H6B 109.4 . . ? C7 N6 H6B 109.4 . . ? H6A N6 H6B 108.0 . . ? N6 C7 C5 110.19(19) . 2_655 ? N6 C7 H7A 109.6 . . ? C5 C7 H7A 109.6 2_655 . ? N6 C7 H7B 109.6 . . ? C5 C7 H7B 109.6 2_655 . ? H7A C7 H7B 108.1 . . ? 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 C7 C5 N6 C7 57.8(3) 2_655 . . . ? C5 N6 C7 C5 -58.2(3) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.190 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.045