# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Judit Galcera' _publ_contact_author_email judit.galcera@gmail.com loop_ _publ_author_name J.Galcera T.Friscic K.E.Hejczyk L.Fabian S.M.Clarke G.M.Day ; E.Molins ; W.Jones data_LM+1.(DMSO-THF) _database_code_depnum_ccdc_archive 'CCDC 856200' #TrackingRef '- LM+1.(DMSO_THF).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - acetylenedicarboxylate - tetrahydrofuran - dimethyl sufoxide (1:0.5:0.80:0.20) ; _chemical_name_common ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - acetylenedicarboxylate - tetrahydrofuran - dimethyl sufoxide (1:0.5:0.80:0.20) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C4 O4, 1.6(C4 H8 O), 0.4(C2 H6 O S)' _chemical_formula_sum 'C29.20 H31.20 Cl4 N10 O6 S0.40' _chemical_formula_weight 772.87 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0783(2) _cell_length_b 10.3174(2) _cell_length_c 16.3132(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.6390(10) _cell_angle_gamma 90.00 _cell_volume 1766.79(6) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 16585 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 31.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 798 _exptl_absorpt_coefficient_mu 0.416 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.921 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 21444 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 30.96 _reflns_number_total 5573 _reflns_number_gt 4045 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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^ > 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^)+(0.0605P)^2^+0.8599P] 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 5573 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1375 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 Cl11 Cl 0.95922(5) 0.08270(5) 0.09046(3) 0.04332(14) Uani 1 1 d . . . Cl21 Cl 1.14026(5) -0.10590(6) 0.22622(4) 0.05261(16) Uani 1 1 d . . . N11 N 0.68649(14) -0.05108(14) -0.09073(9) 0.0277(3) Uani 1 1 d . . . N21 N 0.61031(14) 0.02984(14) -0.15027(9) 0.0280(3) Uani 1 1 d . . . H21 H 0.5959 0.0126 -0.2054 0.034 Uiso 1 1 calc R . . C31 C 0.55526(16) 0.13599(15) -0.12899(10) 0.0258(3) Uani 1 1 d . . . N31 N 0.48885(15) 0.21275(14) -0.19187(9) 0.0338(3) Uani 1 1 d . . . H31A H 0.4512 0.2819 -0.1798 0.041 Uiso 1 1 calc R . . H31B H 0.4822 0.1948 -0.2459 0.041 Uiso 1 1 calc R . . N41 N 0.56541(14) 0.16339(13) -0.04679(9) 0.0284(3) Uani 1 1 d . . . C51 C 0.63677(15) 0.08361(15) 0.01357(10) 0.0255(3) Uani 1 1 d . . . N51 N 0.64543(15) 0.10438(15) 0.09543(9) 0.0318(3) Uani 1 1 d . . . H51A H 0.6045 0.1698 0.1090 0.038 Uiso 1 1 calc R . . H51B H 0.6921 0.0527 0.1362 0.038 Uiso 1 1 calc R . . C61 C 0.70210(15) -0.02547(15) -0.01022(10) 0.0252(3) Uani 1 1 d . . . C611 C 0.78787(15) -0.11352(16) 0.05482(10) 0.0260(3) Uani 1 1 d . . . C621 C 0.90999(16) -0.07268(17) 0.10434(11) 0.0295(3) Uani 1 1 d . . . C641 C 0.95136(18) -0.2824(2) 0.17206(12) 0.0384(4) Uani 1 1 d . . . H641 H 1.0074 -0.3404 0.2115 0.046 Uiso 1 1 calc R . . C631 C 0.99047(16) -0.1572(2) 0.16289(12) 0.0343(4) Uani 1 1 d . . . C651 C 0.83023(18) -0.32262(19) 0.12352(13) 0.0373(4) Uani 1 1 d . . . H651 H 0.8030 -0.4081 0.1302 0.045 Uiso 1 1 calc R . . C661 C 0.74877(16) -0.23878(17) 0.06531(11) 0.0309(3) Uani 1 1 d . . . H661 H 0.6658 -0.2669 0.0324 0.037 Uiso 1 1 calc R . . O12 O 0.52370(14) 0.32563(12) 0.14232(8) 0.0351(3) Uani 1 1 d . . . O22 O 0.58996(12) 0.52688(11) 0.18350(7) 0.0294(3) Uani 1 1 d . . . C12 C 0.54509(15) 0.44059(16) 0.12774(10) 0.0251(3) Uani 1 1 d . . . C22 C 0.51375(16) 0.48185(16) 0.03665(10) 0.0278(3) Uani 1 1 d . . . O13 O 0.7880(5) 0.0040(6) 0.2652(4) 0.0632(16) Uani 0.80 1 d P A 1 C33 C 0.8066(8) 0.0496(12) 0.4116(7) 0.090(3) Uani 0.80 1 d P A 1 H33A H 0.7549 0.0643 0.4503 0.108 Uiso 0.80 1 calc PR A 1 H33B H 0.8862 0.1008 0.4318 0.108 Uiso 0.80 1 calc PR A 1 C43 C 0.7309(3) 0.0760(3) 0.3158(2) 0.0572(8) Uani 0.80 1 d P A 1 H43A H 0.6410 0.0494 0.3033 0.069 Uiso 0.80 1 calc PR A 1 H43B H 0.7330 0.1695 0.3029 0.069 Uiso 0.80 1 calc PR A 1 C13 C 0.8458(4) -0.1108(4) 0.3171(2) 0.0666(9) Uani 0.80 1 d P A 1 H13A H 0.8029 -0.1905 0.2883 0.080 Uiso 0.80 1 calc PR A 1 H13B H 0.9371 -0.1165 0.3222 0.080 Uiso 0.80 1 calc PR A 1 C23 C 0.8326(6) -0.0998(5) 0.4009(3) 0.1041(17) Uani 0.80 1 d P A 1 H23A H 0.9114 -0.1282 0.4460 0.125 Uiso 0.80 1 calc PR A 1 H23B H 0.7606 -0.1532 0.4050 0.125 Uiso 0.80 1 calc PR A 1 S14 S 0.7413(2) -0.0245(3) 0.31838(18) 0.0386(5) Uani 0.20 1 d P B 2 C14 C 0.8109(19) -0.1691(15) 0.3481(12) 0.082(6) Uani 0.20 1 d P B 2 H14A H 0.7882 -0.2274 0.2981 0.123 Uiso 0.20 1 calc PR B 2 H14B H 0.7816 -0.2062 0.3937 0.123 Uiso 0.20 1 calc PR B 2 H14C H 0.9036 -0.1581 0.3698 0.123 Uiso 0.20 1 calc PR B 2 O14 O 0.7999(14) 0.0093(19) 0.2618(13) 0.035(4) Uani 0.20 1 d P B 2 C24 C 0.7870(18) 0.046(3) 0.405(2) 0.051(7) Uani 0.20 1 d P B 2 H24A H 0.7531 0.1346 0.3976 0.076 Uiso 0.20 1 calc PR B 2 H24B H 0.8803 0.0491 0.4253 0.076 Uiso 0.20 1 calc PR B 2 H24C H 0.7569 0.0000 0.4471 0.076 Uiso 0.20 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl11 0.0430(3) 0.0341(2) 0.0506(3) -0.0041(2) 0.0118(2) -0.01202(19) Cl21 0.0307(2) 0.0658(4) 0.0496(3) -0.0089(3) -0.0036(2) -0.0025(2) N11 0.0332(7) 0.0254(7) 0.0241(6) -0.0015(5) 0.0086(5) 0.0015(5) N21 0.0380(7) 0.0267(7) 0.0192(6) -0.0017(5) 0.0091(5) 0.0031(6) C31 0.0322(8) 0.0221(7) 0.0236(7) -0.0014(6) 0.0098(6) -0.0021(6) N31 0.0514(9) 0.0278(7) 0.0223(7) 0.0019(6) 0.0117(6) 0.0089(6) N41 0.0378(7) 0.0248(7) 0.0230(6) -0.0009(5) 0.0105(5) 0.0024(6) C51 0.0301(8) 0.0234(7) 0.0231(7) -0.0026(6) 0.0087(6) -0.0018(6) N51 0.0420(8) 0.0316(7) 0.0216(6) -0.0009(6) 0.0099(6) 0.0067(6) C61 0.0281(7) 0.0237(7) 0.0232(7) -0.0015(6) 0.0075(6) -0.0012(6) C611 0.0283(7) 0.0278(8) 0.0219(7) -0.0015(6) 0.0080(6) 0.0010(6) C621 0.0305(8) 0.0307(8) 0.0275(8) -0.0035(7) 0.0097(6) -0.0023(7) C641 0.0362(9) 0.0418(10) 0.0331(9) 0.0080(8) 0.0054(7) 0.0073(8) C631 0.0266(8) 0.0434(10) 0.0295(8) -0.0032(7) 0.0042(6) 0.0008(7) C651 0.0387(9) 0.0328(9) 0.0386(10) 0.0063(8) 0.0096(8) 0.0003(7) C661 0.0303(8) 0.0299(8) 0.0311(8) 0.0002(7) 0.0078(6) -0.0017(7) O12 0.0571(8) 0.0249(6) 0.0278(6) -0.0020(5) 0.0197(6) -0.0020(6) O22 0.0396(6) 0.0269(6) 0.0190(5) -0.0008(4) 0.0055(5) -0.0008(5) C12 0.0282(7) 0.0269(7) 0.0213(7) -0.0002(6) 0.0094(6) 0.0029(6) C22 0.0342(8) 0.0264(7) 0.0227(7) -0.0023(6) 0.0090(6) -0.0022(6) O13 0.071(3) 0.075(3) 0.038(2) 0.0027(19) 0.009(2) 0.023(2) C33 0.103(6) 0.130(7) 0.049(4) -0.015(4) 0.040(4) -0.020(5) C43 0.0513(17) 0.0546(19) 0.076(2) -0.0054(16) 0.0350(16) -0.0022(14) C13 0.077(2) 0.070(2) 0.0503(18) 0.0118(17) 0.0162(17) 0.0207(19) C23 0.153(5) 0.113(4) 0.048(2) 0.035(2) 0.035(3) 0.031(3) S14 0.0321(11) 0.0391(13) 0.0473(14) -0.0047(11) 0.0165(10) -0.0040(9) C14 0.137(15) 0.059(8) 0.090(11) -0.022(8) 0.094(12) -0.027(9) O14 0.016(4) 0.046(7) 0.045(8) -0.028(6) 0.013(5) -0.017(4) C24 0.014(4) 0.091(16) 0.048(11) -0.029(10) 0.010(5) -0.012(6) _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 Cl11 C621 1.7313(18) . ? Cl21 C631 1.7336(18) . ? N11 C61 1.296(2) . ? N11 N21 1.352(2) . ? N21 C31 1.352(2) . ? N21 H21 0.8800 . ? C31 N31 1.318(2) . ? C31 N41 1.340(2) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N41 C51 1.332(2) . ? C51 N51 1.325(2) . ? C51 C61 1.456(2) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C61 C611 1.486(2) . ? C611 C661 1.391(2) . ? C611 C621 1.401(2) . ? C621 C631 1.387(3) . ? C641 C631 1.385(3) . ? C641 C651 1.386(3) . ? C641 H641 0.9500 . ? C651 C661 1.384(3) . ? C651 H651 0.9500 . ? C661 H661 0.9500 . ? O12 C12 1.247(2) . ? O22 C12 1.256(2) . ? C12 C22 1.477(2) . ? C22 C22 1.196(3) 3_665 ? O13 C43 1.402(7) . ? O13 C13 1.478(7) . ? C33 C43 1.543(11) . ? C33 C23 1.588(13) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C13 C23 1.424(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? S14 O14 1.333(19) . ? S14 C24 1.52(3) . ? S14 C14 1.678(18) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C61 N11 N21 116.90(14) . . ? C31 N21 N11 123.03(13) . . ? C31 N21 H21 118.5 . . ? N11 N21 H21 118.5 . . ? N31 C31 N41 119.96(15) . . ? N31 C31 N21 118.18(14) . . ? N41 C31 N21 121.85(15) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C51 N41 C31 116.72(14) . . ? N51 C51 N41 118.66(15) . . ? N51 C51 C61 120.76(15) . . ? N41 C51 C61 120.57(14) . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? N11 C61 C51 120.73(15) . . ? N11 C61 C611 116.53(14) . . ? C51 C61 C611 122.74(14) . . ? C661 C611 C621 119.34(15) . . ? C661 C611 C61 120.17(15) . . ? C621 C611 C61 120.47(15) . . ? C631 C621 C611 119.86(16) . . ? C631 C621 Cl11 120.82(14) . . ? C611 C621 Cl11 119.32(13) . . ? C631 C641 C651 119.78(17) . . ? C631 C641 H641 120.1 . . ? C651 C641 H641 120.1 . . ? C641 C631 C621 120.41(16) . . ? C641 C631 Cl21 119.55(14) . . ? C621 C631 Cl21 120.04(15) . . ? C661 C651 C641 120.30(18) . . ? C661 C651 H651 119.8 . . ? C641 C651 H651 119.8 . . ? C651 C661 C611 120.31(16) . . ? C651 C661 H661 119.8 . . ? C611 C661 H661 119.8 . . ? O12 C12 O22 126.24(15) . . ? O12 C12 C22 117.92(14) . . ? O22 C12 C22 115.83(14) . . ? C22 C22 C12 178.1(2) 3_665 . ? C43 O13 C13 106.3(5) . . ? C43 C33 C23 96.8(6) . . ? C43 C33 H33A 112.4 . . ? C23 C33 H33A 112.4 . . ? C43 C33 H33B 112.4 . . ? C23 C33 H33B 112.4 . . ? H33A C33 H33B 110.0 . . ? O13 C43 C33 107.6(5) . . ? O13 C43 H43A 110.2 . . ? C33 C43 H43A 110.2 . . ? O13 C43 H43B 110.2 . . ? C33 C43 H43B 110.2 . . ? H43A C43 H43B 108.5 . . ? C23 C13 O13 109.1(4) . . ? C23 C13 H13A 109.9 . . ? O13 C13 H13A 109.9 . . ? C23 C13 H13B 109.9 . . ? O13 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C13 C23 C33 105.1(5) . . ? C13 C23 H23A 110.7 . . ? C33 C23 H23A 110.7 . . ? C13 C23 H23B 110.7 . . ? C33 C23 H23B 110.7 . . ? H23A C23 H23B 108.8 . . ? O14 S14 C24 115.1(14) . . ? O14 S14 C14 98.7(10) . . ? C24 S14 C14 99.9(15) . . ? S14 C14 H14A 109.5 . . ? S14 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? S14 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? S14 C24 H24A 109.5 . . ? S14 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? S14 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.96 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.638 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.098 # Attachment '- LM+1.(THF).cif' data_LM+1.(THF) _database_code_depnum_ccdc_archive 'CCDC 856201' #TrackingRef '- LM+1.(THF).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - acethylenedicarboxylate - tetrahydrofuran (1:0.5:1) ; _chemical_name_common ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - acethylenedicarboxylate - tetrahydrofuran (1:0.5:1) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C4 O4, 2(C4 H8 O)' _chemical_formula_sum 'C30 H32 Cl4 N10 O6' _chemical_formula_weight 770.45 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.2006(3) _cell_length_b 10.2189(2) _cell_length_c 16.3395(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.0430(10) _cell_angle_gamma 90.00 _cell_volume 1767.84(8) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 8045 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 30.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 796 _exptl_absorpt_coefficient_mu 0.392 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.912 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 12205 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 30.03 _reflns_number_total 5115 _reflns_number_gt 4048 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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. The THF solvent molecule shows a disordered into two positions with final refined occupancies of 0.75 and 0.25. The disorder of the THF molecule was modeled using a SAME instruction restraint in SHELX. The disordered atoms were modeled as anisotropic by using an EADP restraint. ; _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^)+(0.0372P)^2^+1.1620P] 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 5115 _refine_ls_number_parameters 242 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.050 _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 Cl11 Cl 0.04333(5) 0.91343(4) 0.41117(3) 0.04187(13) Uani 1 1 d . . . Cl21 Cl -0.14043(4) 1.10204(6) 0.27566(3) 0.04813(15) Uani 1 1 d . . . O22 O 0.40744(11) 1.02650(11) 0.81639(7) 0.0274(2) Uani 1 1 d . . . N41 N 0.43766(13) 0.83842(13) 0.54729(8) 0.0254(3) Uani 1 1 d . . . O12 O 0.47718(13) 0.82426(11) 0.85763(8) 0.0329(3) Uani 1 1 d . . . C51 C 0.36469(15) 0.91747(15) 0.48695(10) 0.0239(3) Uani 1 1 d . . . C61 C 0.29774(15) 1.02579(15) 0.51049(10) 0.0240(3) Uani 1 1 d . . . N21 N 0.39003(13) 0.97023(13) 0.65056(8) 0.0264(3) Uani 1 1 d . . . H21 H 0.4036 0.9868 0.7057 0.032 Uiso 1 1 calc R . . N51 N 0.35513(14) 0.89704(14) 0.40501(9) 0.0289(3) Uani 1 1 d . . . H10A H 0.3967 0.8321 0.3914 0.035 Uiso 1 1 calc R . . H10B H 0.3072 0.9484 0.3642 0.035 Uiso 1 1 calc R . . N11 N 0.31284(13) 1.05070(13) 0.59112(9) 0.0262(3) Uani 1 1 d . . . C12 C 0.45438(15) 0.94008(15) 0.87231(10) 0.0232(3) Uani 1 1 d . . . N31 N 0.51634(14) 0.78934(14) 0.69280(9) 0.0300(3) Uani 1 1 d . . . H3A H 0.5556 0.7210 0.6809 0.036 Uiso 1 1 calc R . . H3B H 0.5229 0.8070 0.7468 0.036 Uiso 1 1 calc R . . C22 C 0.48581(16) 0.98138(15) 0.96350(10) 0.0259(3) Uani 1 1 d . . . C611 C 0.21090(15) 1.11362(15) 0.44528(10) 0.0241(3) Uani 1 1 d . . . C31 C 0.44761(15) 0.86541(15) 0.62958(10) 0.0240(3) Uani 1 1 d . . . C621 C 0.09019(16) 1.07098(16) 0.39678(11) 0.0273(3) Uani 1 1 d . . . C631 C 0.00833(16) 1.15561(19) 0.33828(11) 0.0320(4) Uani 1 1 d . . . C651 C 0.16556(18) 1.32412(18) 0.37620(12) 0.0343(4) Uani 1 1 d . . . H651 H 0.1914 1.4108 0.3692 0.041 Uiso 1 1 calc R . . C641 C 0.04545(17) 1.28238(19) 0.32862(12) 0.0345(4) Uani 1 1 d . . . H641 H -0.0114 1.3405 0.2894 0.041 Uiso 1 1 calc R . . C661 C 0.24838(16) 1.24009(16) 0.43410(11) 0.0285(3) Uani 1 1 d . . . H661 H 0.3310 1.2690 0.4662 0.034 Uiso 1 1 calc R . . O13 O 0.2049(3) 0.5072(4) 0.73320(17) 0.0376(7) Uani 0.747(7) 1 d PD A 1 C13 C 0.2712(3) 0.5811(4) 0.6883(3) 0.0439(8) Uani 0.747(7) 1 d PD A 1 H13A H 0.3624 0.5596 0.7097 0.053 Uiso 0.747(7) 1 calc PR A 1 H13B H 0.2609 0.6760 0.6960 0.053 Uiso 0.747(7) 1 calc PR A 1 C43 C 0.1590(5) 0.3895(5) 0.6835(3) 0.0552(9) Uani 0.747(7) 1 d PD A 1 H43A H 0.0679 0.3780 0.6748 0.066 Uiso 0.747(7) 1 calc PR A 1 H43B H 0.2048 0.3123 0.7152 0.066 Uiso 0.747(7) 1 calc PR A 1 C23 C 0.2127(4) 0.5424(4) 0.5934(2) 0.0612(10) Uani 0.747(7) 1 d PD A 1 H23A H 0.1368 0.5954 0.5642 0.073 Uiso 0.747(7) 1 calc PR A 1 H23B H 0.2741 0.5520 0.5618 0.073 Uiso 0.747(7) 1 calc PR A 1 C33 C 0.1789(4) 0.4008(4) 0.5996(2) 0.0619(10) Uani 0.747(7) 1 d PD A 1 H33A H 0.1012 0.3773 0.5519 0.074 Uiso 0.747(7) 1 calc PR A 1 H33B H 0.2484 0.3427 0.5971 0.074 Uiso 0.747(7) 1 calc PR A 1 O132 O 0.2320(10) 0.4886(14) 0.7345(5) 0.0376(7) Uani 0.253(7) 1 d PD A 2 C132 C 0.2809(9) 0.5605(13) 0.6784(9) 0.0439(8) Uani 0.253(7) 1 d PD A 2 H13C H 0.3590 0.5192 0.6748 0.053 Uiso 0.253(7) 1 calc PR A 2 H13D H 0.3003 0.6515 0.6992 0.053 Uiso 0.253(7) 1 calc PR A 2 C432 C 0.1399(15) 0.3972(14) 0.6821(7) 0.0552(9) Uani 0.253(7) 1 d PD A 2 H43C H 0.0611 0.4024 0.6970 0.066 Uiso 0.253(7) 1 calc PR A 2 H43D H 0.1730 0.3068 0.6935 0.066 Uiso 0.253(7) 1 calc PR A 2 C232 C 0.1777(12) 0.5585(12) 0.5903(7) 0.0612(10) Uani 0.253(7) 1 d PD A 2 H23C H 0.1182 0.6323 0.5844 0.073 Uiso 0.253(7) 1 calc PR A 2 H23D H 0.2141 0.5626 0.5427 0.073 Uiso 0.253(7) 1 calc PR A 2 C332 C 0.1136(12) 0.4294(13) 0.5908(6) 0.0619(10) Uani 0.253(7) 1 d PD A 2 H33C H 0.0215 0.4368 0.5608 0.074 Uiso 0.253(7) 1 calc PR A 2 H33D H 0.1480 0.3612 0.5616 0.074 Uiso 0.253(7) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl11 0.0411(3) 0.0320(2) 0.0506(3) -0.00412(19) 0.0124(2) -0.01118(18) Cl21 0.0272(2) 0.0604(3) 0.0471(3) -0.0116(2) -0.00106(19) -0.0002(2) O22 0.0354(6) 0.0255(6) 0.0189(5) 0.0001(4) 0.0055(4) 0.0003(5) N41 0.0332(7) 0.0224(6) 0.0211(6) -0.0008(5) 0.0093(5) 0.0023(5) O12 0.0537(8) 0.0226(6) 0.0267(6) 0.0004(5) 0.0192(5) 0.0010(5) C51 0.0277(7) 0.0215(7) 0.0231(7) -0.0019(6) 0.0091(6) -0.0014(6) C61 0.0257(7) 0.0216(7) 0.0241(7) -0.0015(6) 0.0075(6) -0.0006(5) N21 0.0346(7) 0.0258(6) 0.0184(6) -0.0016(5) 0.0080(5) 0.0032(5) N51 0.0395(8) 0.0265(7) 0.0201(6) -0.0007(5) 0.0091(6) 0.0075(6) N11 0.0301(7) 0.0239(6) 0.0242(6) -0.0008(5) 0.0083(5) 0.0016(5) C12 0.0256(7) 0.0248(7) 0.0198(7) -0.0010(6) 0.0082(5) -0.0042(6) N31 0.0426(8) 0.0253(7) 0.0217(6) 0.0007(5) 0.0100(6) 0.0053(6) C22 0.0314(8) 0.0241(7) 0.0228(7) 0.0027(6) 0.0096(6) 0.0023(6) C611 0.0261(7) 0.0244(7) 0.0215(7) -0.0020(6) 0.0076(6) 0.0016(6) C31 0.0294(8) 0.0204(7) 0.0230(7) -0.0013(6) 0.0095(6) -0.0026(6) C621 0.0294(8) 0.0264(8) 0.0278(8) -0.0042(6) 0.0118(6) -0.0018(6) C631 0.0241(7) 0.0424(10) 0.0267(8) -0.0064(7) 0.0045(6) 0.0029(7) C651 0.0366(9) 0.0277(8) 0.0380(9) 0.0055(7) 0.0114(7) 0.0016(7) C641 0.0339(9) 0.0373(9) 0.0307(8) 0.0048(7) 0.0082(7) 0.0090(7) C661 0.0280(8) 0.0272(8) 0.0296(8) -0.0006(6) 0.0083(6) -0.0003(6) O13 0.0341(17) 0.0473(15) 0.0309(7) -0.0033(7) 0.0101(8) 0.0013(12) C13 0.0427(13) 0.0421(17) 0.0594(18) -0.0038(12) 0.0337(12) 0.0059(11) C43 0.058(2) 0.0614(16) 0.0455(12) -0.0115(11) 0.0159(12) -0.0164(15) C23 0.050(2) 0.097(2) 0.0475(14) 0.0257(15) 0.0314(17) 0.0314(19) C33 0.055(2) 0.093(3) 0.0405(15) -0.0240(16) 0.0190(17) -0.001(2) O132 0.0341(17) 0.0473(15) 0.0309(7) -0.0033(7) 0.0101(8) 0.0013(12) C132 0.0427(13) 0.0421(17) 0.0594(18) -0.0038(12) 0.0337(12) 0.0059(11) C432 0.058(2) 0.0614(16) 0.0455(12) -0.0115(11) 0.0159(12) -0.0164(15) C232 0.050(2) 0.097(2) 0.0475(14) 0.0257(15) 0.0314(17) 0.0314(19) C332 0.055(2) 0.093(3) 0.0405(15) -0.0240(16) 0.0190(17) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cl11 C621 1.7331(17) . ? Cl21 C631 1.7350(18) . ? O22 C12 1.2560(19) . ? N41 C51 1.329(2) . ? N41 C31 1.3411(19) . ? O12 C12 1.2504(19) . ? C51 N51 1.325(2) . ? C51 C61 1.457(2) . ? C61 N11 1.298(2) . ? C61 C611 1.487(2) . ? N21 N11 1.3487(18) . ? N21 C31 1.351(2) . ? N21 H21 0.8800 . ? N51 H10A 0.8800 . ? N51 H10B 0.8800 . ? C12 C22 1.476(2) . ? N31 C31 1.321(2) . ? N31 H3A 0.8800 . ? N31 H3B 0.8800 . ? C22 C22 1.192(3) 3_677 ? C611 C661 1.389(2) . ? C611 C621 1.395(2) . ? C621 C631 1.389(2) . ? C631 C641 1.385(3) . ? C651 C641 1.383(3) . ? C651 C661 1.386(2) . ? C651 H651 0.9500 . ? C641 H641 0.9500 . ? C661 H661 0.9500 . ? O13 C13 1.419(3) . ? O13 C43 1.448(3) . ? C13 C23 1.526(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C43 C33 1.463(4) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C23 C33 1.508(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? O132 C132 1.417(3) . ? O132 C432 1.448(3) . ? C132 C232 1.523(4) . ? C132 H13C 0.9900 . ? C132 H13D 0.9900 . ? C432 C332 1.461(4) . ? C432 H43C 0.9900 . ? C432 H43D 0.9900 . ? C232 C332 1.504(5) . ? C232 H23C 0.9900 . ? C232 H23D 0.9900 . ? C332 H33C 0.9900 . ? C332 H33D 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 C51 N41 C31 116.64(14) . . ? N51 C51 N41 118.77(14) . . ? N51 C51 C61 120.51(14) . . ? N41 C51 C61 120.71(14) . . ? N11 C61 C51 120.61(14) . . ? N11 C61 C611 116.57(14) . . ? C51 C61 C611 122.82(13) . . ? N11 N21 C31 123.21(13) . . ? N11 N21 H21 118.4 . . ? C31 N21 H21 118.4 . . ? C51 N51 H10A 120.0 . . ? C51 N51 H10B 120.0 . . ? H10A N51 H10B 120.0 . . ? C61 N11 N21 116.88(13) . . ? O12 C12 O22 126.10(14) . . ? O12 C12 C22 117.89(14) . . ? O22 C12 C22 116.01(14) . . ? C31 N31 H3A 120.0 . . ? C31 N31 H3B 120.0 . . ? H3A N31 H3B 120.0 . . ? C22 C22 C12 177.3(2) 3_677 . ? C661 C611 C621 119.62(15) . . ? C661 C611 C61 120.05(14) . . ? C621 C611 C61 120.30(14) . . ? N31 C31 N41 119.97(14) . . ? N31 C31 N21 118.22(14) . . ? N41 C31 N21 121.81(14) . . ? C631 C621 C611 119.74(15) . . ? C631 C621 Cl11 120.70(13) . . ? C611 C621 Cl11 119.56(13) . . ? C641 C631 C621 120.35(16) . . ? C641 C631 Cl21 119.61(14) . . ? C621 C631 Cl21 120.03(14) . . ? C641 C651 C661 120.29(17) . . ? C641 C651 H651 119.9 . . ? C661 C651 H651 119.9 . . ? C651 C641 C631 119.82(16) . . ? C651 C641 H641 120.1 . . ? C631 C641 H641 120.1 . . ? C651 C661 C611 120.17(16) . . ? C651 C661 H661 119.9 . . ? C611 C661 H661 119.9 . . ? C13 O13 C43 107.57(18) . . ? O13 C13 C23 105.3(2) . . ? O13 C13 H13A 110.7 . . ? C23 C13 H13A 110.7 . . ? O13 C13 H13B 110.7 . . ? C23 C13 H13B 110.7 . . ? H13A C13 H13B 108.8 . . ? O13 C43 C33 109.0(2) . . ? O13 C43 H43A 109.9 . . ? C33 C43 H43A 109.9 . . ? O13 C43 H43B 109.9 . . ? C33 C43 H43B 109.9 . . ? H43A C43 H43B 108.3 . . ? C33 C23 C13 102.3(2) . . ? C33 C23 H23A 111.3 . . ? C13 C23 H23A 111.3 . . ? C33 C23 H23B 111.3 . . ? C13 C23 H23B 111.3 . . ? H23A C23 H23B 109.2 . . ? C43 C33 C23 104.9(2) . . ? C43 C33 H33A 110.8 . . ? C23 C33 H33A 110.8 . . ? C43 C33 H33B 110.8 . . ? C23 C33 H33B 110.8 . . ? H33A C33 H33B 108.8 . . ? C132 O132 C432 107.6(2) . . ? O132 C132 C232 105.7(3) . . ? O132 C132 H13C 110.6 . . ? C232 C132 H13C 110.6 . . ? O132 C132 H13D 110.6 . . ? C232 C132 H13D 110.6 . . ? H13C C132 H13D 108.7 . . ? O132 C432 C332 109.1(2) . . ? O132 C432 H43C 109.9 . . ? C332 C432 H43C 109.9 . . ? O132 C432 H43D 109.9 . . ? C332 C432 H43D 109.9 . . ? H43C C432 H43D 108.3 . . ? C332 C232 C132 102.9(3) . . ? C332 C232 H23C 111.2 . . ? C132 C232 H23C 111.2 . . ? C332 C232 H23D 111.2 . . ? C132 C232 H23D 111.2 . . ? H23C C232 H23D 109.1 . . ? C432 C332 C232 105.4(3) . . ? C432 C332 H33C 110.7 . . ? C232 C332 H33C 110.7 . . ? C432 C332 H33D 110.7 . . ? C232 C332 H33D 110.7 . . ? H33C C332 H33D 108.8 . . ? 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 C31 N41 C51 N51 177.93(15) . . . . ? C31 N41 C51 C61 -1.2(2) . . . . ? N51 C51 C61 N11 -175.89(15) . . . . ? N41 C51 C61 N11 3.2(2) . . . . ? N51 C51 C61 C611 3.5(2) . . . . ? N41 C51 C61 C611 -177.42(14) . . . . ? C51 C61 N11 N21 -1.6(2) . . . . ? C611 C61 N11 N21 179.05(13) . . . . ? C31 N21 N11 C61 -1.9(2) . . . . ? N11 C61 C611 C661 73.7(2) . . . . ? C51 C61 C611 C661 -105.71(18) . . . . ? N11 C61 C611 C621 -104.51(18) . . . . ? C51 C61 C611 C621 76.1(2) . . . . ? C51 N41 C31 N31 178.53(15) . . . . ? C51 N41 C31 N21 -2.2(2) . . . . ? N11 N21 C31 N31 -176.69(15) . . . . ? N11 N21 C31 N41 4.1(2) . . . . ? C661 C611 C621 C631 -0.5(2) . . . . ? C61 C611 C621 C631 177.69(15) . . . . ? C661 C611 C621 Cl11 -179.70(12) . . . . ? C61 C611 C621 Cl11 -1.5(2) . . . . ? C611 C621 C631 C641 -0.7(3) . . . . ? Cl11 C621 C631 C641 178.49(14) . . . . ? C611 C621 C631 Cl21 178.31(12) . . . . ? Cl11 C621 C631 Cl21 -2.5(2) . . . . ? C661 C651 C641 C631 -0.7(3) . . . . ? C621 C631 C641 C651 1.3(3) . . . . ? Cl21 C631 C641 C651 -177.74(14) . . . . ? C641 C651 C661 C611 -0.6(3) . . . . ? C621 C611 C661 C651 1.1(2) . . . . ? C61 C611 C661 C651 -177.05(16) . . . . ? C43 O13 C13 C23 26.8(3) . . . . ? C13 O13 C43 C33 -9.5(4) . . . . ? O13 C13 C23 C33 -33.3(3) . . . . ? O13 C43 C33 C23 -12.1(5) . . . . ? C13 C23 C33 C43 27.1(4) . . . . ? C432 O132 C132 C232 26.1(8) . . . . ? C132 O132 C432 C332 -10.8(11) . . . . ? O132 C132 C232 C332 -31.0(7) . . . . ? O132 C432 C332 C232 -9.2(11) . . . . ? C132 C232 C332 C432 24.0(9) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.360 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.054 # Attachment '- LM+2(guest-free).cif' data_LM+2 _database_code_depnum_ccdc_archive 'CCDC 856202' #TrackingRef '- LM+2(guest-free).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - fumarate(2:1) ; _chemical_name_common ;3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - fumarate(2:1) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C4 H2 O4' _chemical_formula_sum 'C22 H18 Cl4 N10 O4' _chemical_formula_weight 628.26 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' Cl Cl 0.1484 0.1585 '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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.8481(3) _cell_length_b 9.1579(2) _cell_length_c 11.2303(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.928(2) _cell_angle_gamma 90.00 _cell_volume 1297.41(5) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 16711 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 20.6 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.509 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.838 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 13165 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 20.87 _reflns_number_total 1353 _reflns_number_gt 1321 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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^)+(0.0100P)^2^+2.6856P] 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 1353 _refine_ls_number_parameters 230 _refine_ls_number_restraints 35 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0876 _refine_ls_goodness_of_fit_ref 1.203 _refine_ls_restrained_S_all 1.185 _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 Cl11 Cl 0.12050(8) 1.01467(12) 0.06972(10) 0.0441(4) Uani 0.9280(15) 1 d P A 1 Cl21 Cl 0.36317(9) 1.02383(14) 0.06092(12) 0.0551(4) Uani 0.9280(15) 1 d P A 1 N11 N -0.0199(3) 0.7431(6) 0.1621(4) 0.0309(12) Uani 0.9280(15) 1 d PD A 1 N21 N -0.1207(3) 0.7560(8) 0.1820(5) 0.0286(9) Uani 0.9280(15) 1 d PD A 1 H21 H -0.1726 0.7191 0.1279 0.034 Uiso 0.9280(15) 1 calc PR A 1 C31 C -0.1453(3) 0.8225(8) 0.2802(4) 0.0232(10) Uani 0.9280(15) 1 d PD A 1 N31 N -0.2446(3) 0.8309(6) 0.2911(3) 0.0277(11) Uani 0.9280(15) 1 d PD A 1 H31A H -0.2617 0.8743 0.3547 0.033 Uiso 0.9280(15) 1 calc PR A 1 H31B H -0.2945 0.7932 0.2349 0.033 Uiso 0.9280(15) 1 calc PR A 1 N41 N -0.0694(3) 0.8804(8) 0.3666(5) 0.0243(9) Uani 0.9280(15) 1 d PD A 1 C51 C 0.0303(3) 0.8656(6) 0.3529(5) 0.0235(15) Uani 0.9280(15) 1 d PD A 1 N51 N 0.1071(3) 0.9153(4) 0.4374(4) 0.0287(14) Uani 0.9280(15) 1 d PD A 1 H51A H 0.0921 0.9580 0.5023 0.034 Uiso 0.9280(15) 1 calc PR A 1 H51B H 0.1735 0.9060 0.4291 0.034 Uiso 0.9280(15) 1 calc PR A 1 C61 C 0.0552(3) 0.7970(4) 0.2439(4) 0.0258(12) Uani 0.9280(15) 1 d PD A 1 C611 C 0.1683(3) 0.7902(5) 0.2279(4) 0.0272(11) Uani 0.9280(15) 1 d PD A 1 C621 C 0.2070(3) 0.8912(5) 0.1548(4) 0.0313(11) Uani 0.9280(15) 1 d PD A 1 C631 C 0.3149(4) 0.8942(5) 0.1486(4) 0.0375(11) Uani 0.9280(15) 1 d PD A 1 C641 C 0.3820(3) 0.7936(6) 0.2149(4) 0.0425(12) Uani 0.9280(15) 1 d PD A 1 H641 H 0.4553 0.7945 0.2114 0.051 Uiso 0.9280(15) 1 calc PR A 1 C651 C 0.3440(3) 0.6924(6) 0.2858(5) 0.0450(13) Uani 0.9280(15) 1 d PD A 1 H651 H 0.3908 0.6224 0.3297 0.054 Uiso 0.9280(15) 1 calc PR A 1 C661 C 0.2377(3) 0.6919(5) 0.2935(5) 0.0384(12) Uani 0.9280(15) 1 d PD A 1 H661 H 0.2124 0.6231 0.3445 0.046 Uiso 0.9280(15) 1 calc PR A 1 Cl13 Cl 0.1958(11) 0.6298(16) 0.3602(14) 0.0441(4) Uani 0.0720(15) 1 d P A 2 Cl23 Cl 0.4278(13) 0.6581(18) 0.3137(15) 0.0551(4) Uani 0.0720(15) 1 d P A 2 N13 N -0.036(3) 0.773(9) 0.164(5) 0.0309(12) Uani 0.0720(15) 1 d PD A 2 N23 N -0.131(3) 0.768(11) 0.200(6) 0.0286(9) Uani 0.0720(15) 1 d PD A 2 H23 H -0.1836 0.7199 0.1541 0.034 Uiso 0.0720(15) 1 calc PR A 2 C33 C -0.150(3) 0.832(10) 0.302(6) 0.0232(10) Uani 0.0720(15) 1 d PD A 2 N33 N -0.245(3) 0.823(10) 0.328(6) 0.0277(11) Uani 0.0720(15) 1 d PD A 2 H33A H -0.2575 0.8606 0.3960 0.033 Uiso 0.0720(15) 1 calc PR A 2 H33B H -0.2963 0.7786 0.2778 0.033 Uiso 0.0720(15) 1 calc PR A 2 N43 N -0.072(3) 0.899(12) 0.379(6) 0.0243(9) Uani 0.0720(15) 1 d PD A 2 C53 C 0.024(3) 0.898(11) 0.352(6) 0.0235(15) Uani 0.0720(15) 1 d PD A 2 N53 N 0.103(3) 0.956(9) 0.428(5) 0.0287(14) Uani 0.0720(15) 1 d PD A 2 H53A H 0.0928 0.9946 0.4967 0.034 Uiso 0.0720(15) 1 calc PR A 2 H53B H 0.1675 0.9551 0.4112 0.034 Uiso 0.0720(15) 1 calc PR A 2 C63 C 0.041(2) 0.836(5) 0.237(4) 0.0258(12) Uani 0.0720(15) 1 d PD A 2 C613 C 0.151(2) 0.837(4) 0.210(4) 0.0272(11) Uani 0.0720(15) 1 d PD A 2 C623 C 0.229(3) 0.745(6) 0.272(6) 0.0384(12) Uani 0.0720(15) 1 d PD A 2 C633 C 0.331(3) 0.746(7) 0.247(6) 0.0450(13) Uani 0.0720(15) 1 d PD A 2 C643 C 0.356(3) 0.847(8) 0.166(7) 0.0425(12) Uani 0.0720(15) 1 d PD A 2 H643 H 0.4257 0.8497 0.1485 0.051 Uiso 0.0720(15) 1 calc PR A 2 C653 C 0.281(3) 0.943(6) 0.109(5) 0.0375(11) Uani 0.0720(15) 1 d PD A 2 H653 H 0.2999 1.0149 0.0554 0.045 Uiso 0.0720(15) 1 calc PR A 2 C663 C 0.179(3) 0.937(6) 0.130(5) 0.0313(11) Uani 0.0720(15) 1 d PD A 2 H663 H 0.1266 1.0027 0.0887 0.038 Uiso 0.0720(15) 1 calc PR A 2 O12 O 0.72141(17) 0.8965(3) 0.5372(2) 0.0299(6) Uani 1 1 d . . . O22 O 0.59917(19) 0.8015(3) 0.6301(3) 0.0525(9) Uani 1 1 d . . . C12 C 0.6273(3) 0.8890(4) 0.5586(3) 0.0290(9) Uani 1 1 d . . . C22 C 0.5488(3) 0.9935(4) 0.4921(3) 0.0310(9) Uani 1 1 d . . . H22 H 0.5712 1.0552 0.4338 0.037 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 Cl11 0.0332(6) 0.0449(7) 0.0549(7) 0.0083(6) 0.0097(5) 0.0000(5) Cl21 0.0423(7) 0.0585(8) 0.0719(8) -0.0068(7) 0.0301(6) -0.0163(6) N11 0.022(2) 0.039(3) 0.0330(18) -0.0098(18) 0.0078(17) -0.005(2) N21 0.0156(19) 0.042(2) 0.028(2) -0.0103(18) 0.0037(14) -0.0087(18) C31 0.020(2) 0.025(2) 0.026(3) -0.001(2) 0.0088(19) -0.0003(17) N31 0.0197(19) 0.041(2) 0.022(3) -0.008(3) 0.0040(15) -0.0026(14) N41 0.0141(17) 0.033(3) 0.026(2) -0.0075(16) 0.0025(14) -0.0056(15) C51 0.021(2) 0.022(4) 0.027(2) -0.002(2) 0.0032(18) -0.004(2) N51 0.0169(17) 0.039(4) 0.0312(19) -0.012(2) 0.0067(15) -0.0021(17) C61 0.019(2) 0.027(3) 0.032(2) -0.005(2) 0.0060(19) -0.0003(19) C611 0.022(2) 0.033(3) 0.027(2) -0.010(2) 0.006(2) -0.003(2) C621 0.021(3) 0.037(3) 0.035(3) -0.013(2) 0.003(2) 0.001(2) C631 0.030(3) 0.042(3) 0.045(3) -0.015(2) 0.018(3) -0.007(2) C641 0.024(3) 0.052(3) 0.052(3) -0.014(3) 0.008(3) 0.000(3) C651 0.021(3) 0.057(4) 0.054(4) -0.009(3) 0.001(2) 0.013(2) C661 0.030(3) 0.039(3) 0.047(3) -0.005(3) 0.010(2) 0.003(2) Cl13 0.0332(6) 0.0449(7) 0.0549(7) 0.0083(6) 0.0097(5) 0.0000(5) Cl23 0.0423(7) 0.0585(8) 0.0719(8) -0.0068(7) 0.0301(6) -0.0163(6) N13 0.022(2) 0.039(3) 0.0330(18) -0.0098(18) 0.0078(17) -0.005(2) N23 0.0156(19) 0.042(2) 0.028(2) -0.0103(18) 0.0037(14) -0.0087(18) C33 0.020(2) 0.025(2) 0.026(3) -0.001(2) 0.0088(19) -0.0003(17) N33 0.0197(19) 0.041(2) 0.022(3) -0.008(3) 0.0040(15) -0.0026(14) N43 0.0141(17) 0.033(3) 0.026(2) -0.0075(16) 0.0025(14) -0.0056(15) C53 0.021(2) 0.022(4) 0.027(2) -0.002(2) 0.0032(18) -0.004(2) N53 0.0169(17) 0.039(4) 0.0312(19) -0.012(2) 0.0067(15) -0.0021(17) C63 0.019(2) 0.027(3) 0.032(2) -0.005(2) 0.0060(19) -0.0003(19) C613 0.022(2) 0.033(3) 0.027(2) -0.010(2) 0.006(2) -0.003(2) C623 0.030(3) 0.039(3) 0.047(3) -0.005(3) 0.010(2) 0.003(2) C633 0.021(3) 0.057(4) 0.054(4) -0.009(3) 0.001(2) 0.013(2) C643 0.024(3) 0.052(3) 0.052(3) -0.014(3) 0.008(3) 0.000(3) C653 0.030(3) 0.042(3) 0.045(3) -0.015(2) 0.018(3) -0.007(2) C663 0.021(3) 0.037(3) 0.035(3) -0.013(2) 0.003(2) 0.001(2) O12 0.0130(14) 0.0425(16) 0.0344(14) 0.0065(12) 0.0050(11) 0.0037(11) O22 0.0182(14) 0.072(2) 0.069(2) 0.0435(18) 0.0136(14) 0.0099(14) C12 0.021(2) 0.038(2) 0.027(2) 0.0009(19) 0.0024(17) 0.0008(19) C22 0.0222(18) 0.039(2) 0.032(2) 0.0127(18) 0.0061(17) 0.0008(19) _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 Cl11 C621 1.739(4) . ? Cl21 C631 1.731(5) . ? N11 C61 1.297(4) . ? N11 N21 1.360(4) . ? N21 C31 1.349(4) . ? N21 H21 0.8800 . ? C31 N31 1.308(5) . ? C31 N41 1.347(4) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N41 C51 1.326(4) . ? C51 N51 1.314(4) . ? C51 C61 1.465(5) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C61 C611 1.499(5) . ? C611 C661 1.377(6) . ? C611 C621 1.389(6) . ? C621 C631 1.402(6) . ? C631 C641 1.379(6) . ? C641 C651 1.370(6) . ? C641 H641 0.9500 . ? C651 C661 1.385(6) . ? C651 H651 0.9500 . ? C661 H661 0.9500 . ? Cl13 C623 1.56(4) . ? Cl23 C633 1.55(4) . ? N13 C63 1.298(5) . ? N13 N23 1.360(5) . ? N23 C33 1.349(5) . ? N23 H23 0.8800 . ? C33 N33 1.308(5) . ? C33 N43 1.347(5) . ? N33 H33A 0.8800 . ? N33 H33B 0.8800 . ? N43 C53 1.326(5) . ? C53 N53 1.314(5) . ? C53 C63 1.465(5) . ? N53 H53A 0.8800 . ? N53 H53B 0.8800 . ? C63 C613 1.499(5) . ? C613 C663 1.378(6) . ? C613 C623 1.390(6) . ? C623 C633 1.402(6) . ? C633 C643 1.380(6) . ? C643 C653 1.370(7) . ? C643 H643 0.9500 . ? C653 C663 1.386(6) . ? C653 H653 0.9500 . ? C663 H663 0.9500 . ? O12 C12 1.278(4) . ? O22 C12 1.237(4) . ? C12 C22 1.485(5) . ? C22 C22 1.305(7) 3_676 ? C22 H22 0.9500 . ? 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 C61 N11 N21 117.0(3) . . ? C31 N21 N11 123.5(3) . . ? C31 N21 H21 118.3 . . ? N11 N21 H21 118.3 . . ? N31 C31 N41 119.7(3) . . ? N31 C31 N21 119.2(3) . . ? N41 C31 N21 121.1(3) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C51 N41 C31 117.3(3) . . ? N51 C51 N41 119.4(3) . . ? N51 C51 C61 119.9(3) . . ? N41 C51 C61 120.7(3) . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? N11 C61 C51 120.3(3) . . ? N11 C61 C611 120.5(3) . . ? C51 C61 C611 119.2(3) . . ? C661 C611 C621 118.9(3) . . ? C661 C611 C61 120.5(4) . . ? C621 C611 C61 120.4(4) . . ? C611 C621 C631 120.7(4) . . ? C611 C621 Cl11 119.7(3) . . ? C631 C621 Cl11 119.7(3) . . ? C641 C631 C621 118.9(4) . . ? C641 C631 Cl21 120.7(4) . . ? C621 C631 Cl21 120.4(4) . . ? C651 C641 C631 120.7(4) . . ? C651 C641 H641 119.6 . . ? C631 C641 H641 119.6 . . ? C641 C651 C661 120.1(4) . . ? C641 C651 H651 119.9 . . ? C661 C651 H651 119.9 . . ? C611 C661 C651 120.7(4) . . ? C611 C661 H661 119.7 . . ? C651 C661 H661 119.7 . . ? C63 N13 N23 117.0(4) . . ? C33 N23 N13 123.4(4) . . ? C33 N23 H23 118.3 . . ? N13 N23 H23 118.3 . . ? N33 C33 N43 119.7(4) . . ? N33 C33 N23 119.2(4) . . ? N43 C33 N23 121.1(3) . . ? C33 N33 H33A 120.0 . . ? C33 N33 H33B 120.0 . . ? H33A N33 H33B 120.0 . . ? C53 N43 C33 117.3(4) . . ? N53 C53 N43 119.4(4) . . ? N53 C53 C63 119.9(4) . . ? N43 C53 C63 120.7(4) . . ? C53 N53 H53A 120.0 . . ? C53 N53 H53B 120.0 . . ? H53A N53 H53B 120.0 . . ? N13 C63 C53 120.2(4) . . ? N13 C63 C613 120.5(4) . . ? C53 C63 C613 119.2(4) . . ? C663 C613 C623 118.9(4) . . ? C663 C613 C63 120.5(4) . . ? C623 C613 C63 120.4(4) . . ? C613 C623 C633 120.6(5) . . ? C613 C623 Cl13 118(2) . . ? C633 C623 Cl13 121(2) . . ? C643 C633 C623 118.8(5) . . ? C643 C633 Cl23 114(3) . . ? C623 C633 Cl23 127(3) . . ? C653 C643 C633 120.7(5) . . ? C653 C643 H643 119.6 . . ? C633 C643 H643 119.6 . . ? C643 C653 C663 120.1(5) . . ? C643 C653 H653 119.9 . . ? C663 C653 H653 119.9 . . ? C613 C663 C653 120.7(5) . . ? C613 C663 H663 119.7 . . ? C653 C663 H663 119.7 . . ? O22 C12 O12 124.1(3) . . ? O22 C12 C22 119.3(3) . . ? O12 C12 C22 116.6(3) . . ? C22 C22 C12 124.7(4) 3_676 . ? C22 C22 H22 117.6 3_676 . ? C12 C22 H22 117.6 . . ? 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 C61 N11 N21 C31 0.8(8) . . . . ? N11 N21 C31 N31 179.3(6) . . . . ? N11 N21 C31 N41 -0.4(9) . . . . ? N31 C31 N41 C51 178.3(7) . . . . ? N21 C31 N41 C51 -2.0(8) . . . . ? C31 N41 C51 N51 -177.3(6) . . . . ? C31 N41 C51 C61 3.8(7) . . . . ? N21 N11 C61 C51 1.1(7) . . . . ? N21 N11 C61 C611 -178.8(5) . . . . ? N51 C51 C61 N11 177.6(6) . . . . ? N41 C51 C61 N11 -3.6(7) . . . . ? N51 C51 C61 C611 -2.5(7) . . . . ? N41 C51 C61 C611 176.3(5) . . . . ? N11 C61 C611 C661 -104.9(5) . . . . ? C51 C61 C611 C661 75.2(5) . . . . ? N11 C61 C611 C621 80.7(6) . . . . ? C51 C61 C611 C621 -99.2(5) . . . . ? C661 C611 C621 C631 -0.6(6) . . . . ? C61 C611 C621 C631 173.9(4) . . . . ? C661 C611 C621 Cl11 179.1(3) . . . . ? C61 C611 C621 Cl11 -6.4(5) . . . . ? C611 C621 C631 C641 1.0(6) . . . . ? Cl11 C621 C631 C641 -178.7(3) . . . . ? C611 C621 C631 Cl21 -178.1(3) . . . . ? Cl11 C621 C631 Cl21 2.2(6) . . . . ? C621 C631 C641 C651 0.0(7) . . . . ? Cl21 C631 C641 C651 179.0(4) . . . . ? C631 C641 C651 C661 -1.3(7) . . . . ? C621 C611 C661 C651 -0.7(6) . . . . ? C61 C611 C661 C651 -175.2(4) . . . . ? C641 C651 C661 C611 1.7(7) . . . . ? C63 N13 N23 C33 4(9) . . . . ? N13 N23 C33 N33 179(9) . . . . ? N13 N23 C33 N43 -4(11) . . . . ? N33 C33 N43 C53 176(9) . . . . ? N23 C33 N43 C53 -1(9) . . . . ? C33 N43 C53 N53 -176(11) . . . . ? C33 N43 C53 C63 5(7) . . . . ? N23 N13 C63 C53 0(8) . . . . ? N23 N13 C63 C613 175(5) . . . . ? N53 C53 C63 N13 177(10) . . . . ? N43 C53 C63 N13 -4(9) . . . . ? N53 C53 C63 C613 1(11) . . . . ? N43 C53 C63 C613 180(5) . . . . ? N13 C63 C613 C663 81(7) . . . . ? C53 C63 C613 C663 -103(6) . . . . ? N13 C63 C613 C623 -105(6) . . . . ? C53 C63 C613 C623 71(7) . . . . ? C663 C613 C623 C633 -6(7) . . . . ? C63 C613 C623 C633 -180(4) . . . . ? C663 C613 C623 Cl13 -179(5) . . . . ? C63 C613 C623 Cl13 7(7) . . . . ? C613 C623 C633 C643 5(8) . . . . ? Cl13 C623 C633 C643 178(7) . . . . ? C613 C623 C633 Cl23 176(6) . . . . ? Cl13 C623 C633 Cl23 -11(8) . . . . ? C623 C633 C643 C653 -1(11) . . . . ? Cl23 C633 C643 C653 -173(7) . . . . ? C633 C643 C653 C663 -2(12) . . . . ? C623 C613 C663 C653 2(7) . . . . ? C63 C613 C663 C653 176(5) . . . . ? C643 C653 C663 C613 2(10) . . . . ? O22 C12 C22 C22 4.0(7) . . . 3_676 ? O12 C12 C22 C22 -175.9(5) . . . 3_676 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 20.87 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.216 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.053 # Attachment '- LM+2.(DMSO).cif' data_LM+2.(DMSO) _database_code_depnum_ccdc_archive 'CCDC 856203' #TrackingRef '- LM+2.(DMSO).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - fumarate - dimethyl sulfoxide (1:0.5:1) ; _chemical_name_common ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - fumarate -dimethyl sulfoxide (1:0.5:1) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C4 H2 O4, 2(C2 H6 O S)' _chemical_formula_sum 'C26 H30 Cl4 N10 O6 S2' _chemical_formula_weight 784.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.6601(2) _cell_length_b 10.9576(2) _cell_length_c 15.8831(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.7680(10) _cell_angle_gamma 90.00 _cell_volume 1756.64(6) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 28206 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 33.73 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.511 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.815 _exptl_absorpt_correction_T_max 0.919 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 29063 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 33.73 _reflns_number_total 6992 _reflns_number_gt 5744 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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^ > 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^)+(0.0767P)^2^+1.1765P] 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 6992 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1607 _refine_ls_wR_factor_gt 0.1480 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 H22 H -0.054(2) 0.379(2) -0.0104(14) 0.027(5) Uiso 1 1 d . . . Cl11 Cl 0.61837(5) 0.05487(4) 0.10063(3) 0.03748(11) Uani 1 1 d . . . Cl21 Cl 0.58792(6) -0.14470(7) 0.23606(4) 0.05573(17) Uani 1 1 d . . . N11 N 0.72525(12) -0.04511(10) -0.09941(8) 0.0217(2) Uani 1 1 d . . . N21 N 0.73764(13) 0.03833(11) -0.15871(8) 0.0233(2) Uani 1 1 d . . . H21 H 0.7058 0.0211 -0.2158 0.028 Uiso 1 1 calc R . . C31 C 0.79714(14) 0.14746(12) -0.13375(9) 0.0224(2) Uani 1 1 d . . . N31 N 0.79017(15) 0.23037(12) -0.19568(8) 0.0312(3) Uani 1 1 d . . . H31A H 0.8291 0.3016 -0.1808 0.037 Uiso 1 1 calc R . . H31B H 0.7466 0.2143 -0.2518 0.037 Uiso 1 1 calc R . . N41 N 0.86361(13) 0.17252(11) -0.04857(8) 0.0252(2) Uani 1 1 d . . . C51 C 0.86166(14) 0.08885(12) 0.01167(9) 0.0221(2) Uani 1 1 d . . . N51 N 0.93475(14) 0.10691(13) 0.09532(8) 0.0289(3) Uani 1 1 d . . . H51A H 0.9834 0.1732 0.1102 0.035 Uiso 1 1 calc R . . H51B H 0.9348 0.0526 0.1361 0.035 Uiso 1 1 calc R . . C61 C 0.78137(13) -0.02117(12) -0.01557(8) 0.0202(2) Uani 1 1 d . . . C611 C 0.76577(13) -0.11245(12) 0.04943(9) 0.0205(2) Uani 1 1 d . . . C621 C 0.69251(14) -0.08614(14) 0.10614(9) 0.0242(2) Uani 1 1 d . . . C631 C 0.67884(16) -0.17398(17) 0.16588(11) 0.0316(3) Uani 1 1 d . . . C641 C 0.73842(18) -0.28734(17) 0.17035(12) 0.0345(3) Uani 1 1 d . . . H641 H 0.7285 -0.3470 0.2112 0.041 Uiso 1 1 calc R . . C651 C 0.81226(19) -0.31325(15) 0.11521(12) 0.0340(3) Uani 1 1 d . . . H651 H 0.8541 -0.3905 0.1187 0.041 Uiso 1 1 calc R . . C661 C 0.82561(15) -0.22658(14) 0.05460(10) 0.0270(3) Uani 1 1 d . . . H661 H 0.8758 -0.2453 0.0165 0.032 Uiso 1 1 calc R . . S113 S 0.43415(8) 0.45621(8) 0.18188(6) 0.04509(19) Uani 0.65 1 d P A 1 O113 O 0.5637(3) 0.5038(3) 0.2446(2) 0.0399(6) Uani 0.65 1 d P A 1 C113 C 0.4794(12) 0.3221(9) 0.1320(7) 0.123(5) Uani 0.65 1 d P A 1 H11A H 0.5011 0.2554 0.1754 0.184 Uiso 0.65 1 calc PR A 1 H11B H 0.5567 0.3404 0.1134 0.184 Uiso 0.65 1 calc PR A 1 H11C H 0.4051 0.2977 0.0800 0.184 Uiso 0.65 1 calc PR A 1 C213 C 0.4021(12) 0.5564(11) 0.0854(8) 0.126(4) Uani 0.65 1 d P A 1 H21A H 0.3752 0.6371 0.1001 0.188 Uiso 0.65 1 calc PR A 1 H21B H 0.3311 0.5217 0.0355 0.188 Uiso 0.65 1 calc PR A 1 H21C H 0.4828 0.5642 0.0689 0.188 Uiso 0.65 1 calc PR A 1 S123 S 0.5219(4) 0.4583(5) 0.1541(3) 0.1351(17) Uani 0.35 1 d P B 2 O123 O 0.5145(11) 0.4781(12) 0.2408(7) 0.117(5) Uani 0.35 1 d P B 2 C123 C 0.4423(17) 0.3262(14) 0.1368(12) 0.068(4) Uani 0.35 1 d P B 2 H12A H 0.5013 0.2619 0.1702 0.101 Uiso 0.35 1 calc PR B 2 H12B H 0.4138 0.3067 0.0732 0.101 Uiso 0.35 1 calc PR B 2 H12C H 0.3645 0.3319 0.1567 0.101 Uiso 0.35 1 calc PR B 2 C223 C 0.3913(8) 0.5500(7) 0.0849(5) 0.0327(13) Uani 0.35 1 d P B 2 H22A H 0.4213 0.6349 0.0869 0.049 Uiso 0.35 1 calc PR B 2 H22B H 0.3147 0.5458 0.1062 0.049 Uiso 0.35 1 calc PR B 2 H22C H 0.3660 0.5200 0.0236 0.049 Uiso 0.35 1 calc PR B 2 O12 O 0.11873(12) 0.51977(10) 0.16737(7) 0.0286(2) Uani 1 1 d . . . C22 C -0.00211(13) 0.44857(11) 0.02176(8) 0.0203(2) Uani 1 1 d . . . C12 C 0.07665(13) 0.42912(12) 0.11751(8) 0.0193(2) Uani 1 1 d . . . O22 O 0.09736(11) 0.31969(9) 0.14227(7) 0.0263(2) 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 Cl11 0.0415(2) 0.0348(2) 0.0381(2) -0.00511(15) 0.01565(17) 0.01200(16) Cl21 0.0591(3) 0.0770(4) 0.0477(3) 0.0077(3) 0.0403(3) 0.0088(3) N11 0.0266(5) 0.0193(5) 0.0178(5) -0.0017(4) 0.0052(4) -0.0024(4) N21 0.0311(6) 0.0199(5) 0.0158(4) -0.0019(4) 0.0031(4) -0.0049(4) C31 0.0272(6) 0.0197(5) 0.0175(5) -0.0014(4) 0.0033(4) -0.0032(4) N31 0.0459(8) 0.0234(6) 0.0174(5) 0.0015(4) 0.0004(5) -0.0104(5) N41 0.0330(6) 0.0223(5) 0.0163(5) -0.0005(4) 0.0023(4) -0.0070(4) C51 0.0267(6) 0.0202(5) 0.0173(5) -0.0016(4) 0.0043(4) -0.0035(4) N51 0.0379(7) 0.0267(6) 0.0166(5) 0.0000(4) 0.0011(4) -0.0103(5) C61 0.0237(5) 0.0189(5) 0.0171(5) -0.0017(4) 0.0053(4) -0.0020(4) C611 0.0230(5) 0.0198(5) 0.0187(5) -0.0015(4) 0.0069(4) -0.0017(4) C621 0.0250(6) 0.0262(6) 0.0221(6) -0.0018(5) 0.0084(5) 0.0018(5) C631 0.0314(7) 0.0420(8) 0.0262(7) 0.0025(6) 0.0159(6) -0.0005(6) C641 0.0382(8) 0.0365(8) 0.0315(7) 0.0098(6) 0.0150(6) -0.0012(6) C651 0.0412(8) 0.0254(7) 0.0381(8) 0.0082(6) 0.0167(7) 0.0045(6) C661 0.0318(7) 0.0237(6) 0.0288(7) 0.0014(5) 0.0145(5) 0.0022(5) S113 0.0317(3) 0.0455(4) 0.0583(5) 0.0092(3) 0.0149(3) 0.0016(3) O113 0.0495(15) 0.0402(12) 0.0253(12) -0.0067(9) 0.0055(11) -0.0047(11) C113 0.148(9) 0.062(5) 0.097(7) -0.046(4) -0.047(6) 0.048(5) C213 0.112(7) 0.147(10) 0.089(6) 0.020(6) -0.009(5) -0.032(6) S123 0.109(3) 0.152(4) 0.119(3) -0.068(3) 0.001(2) 0.012(3) O123 0.117(9) 0.144(10) 0.048(4) -0.054(5) -0.033(5) 0.024(7) C123 0.092(9) 0.054(7) 0.070(7) -0.024(5) 0.044(8) -0.028(7) C223 0.035(3) 0.036(3) 0.025(3) 0.003(2) 0.007(2) 0.012(2) O12 0.0443(6) 0.0191(4) 0.0159(4) -0.0009(3) 0.0007(4) -0.0014(4) C22 0.0251(6) 0.0189(5) 0.0145(5) -0.0007(4) 0.0029(4) 0.0011(4) C12 0.0230(5) 0.0194(5) 0.0140(5) 0.0008(4) 0.0039(4) 0.0000(4) O22 0.0353(5) 0.0183(4) 0.0190(4) 0.0023(3) 0.0000(4) -0.0013(4) _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 Cl11 C621 1.7249(15) . ? Cl21 C631 1.7264(16) . ? N11 C61 1.2990(16) . ? N11 N21 1.3493(16) . ? N21 C31 1.3519(17) . ? N21 H21 0.8800 . ? C31 N31 1.3234(18) . ? C31 N41 1.3382(17) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N41 C51 1.3302(18) . ? C51 N51 1.3212(17) . ? C51 C61 1.4611(18) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C61 C611 1.4847(18) . ? C611 C661 1.394(2) . ? C611 C621 1.3989(19) . ? C621 C631 1.392(2) . ? C631 C641 1.386(3) . ? C641 C651 1.382(2) . ? C641 H641 0.9500 . ? C651 C661 1.392(2) . ? C651 H651 0.9500 . ? C661 H661 0.9500 . ? S113 O113 1.512(3) . ? S113 C113 1.808(10) . ? S113 C213 1.825(11) . ? C113 H11A 0.9800 . ? C113 H11B 0.9800 . ? C113 H11C 0.9800 . ? C213 H21A 0.9800 . ? C213 H21B 0.9800 . ? C213 H21C 0.9800 . ? S123 O123 1.421(13) . ? S123 C123 1.655(15) . ? S123 C223 1.781(8) . ? C123 H12A 0.9800 . ? C123 H12B 0.9800 . ? C123 H12C 0.9800 . ? C223 H22A 0.9800 . ? C223 H22B 0.9800 . ? C223 H22C 0.9800 . ? O12 C12 1.2595(16) . ? C22 C22 1.330(3) 3_565 ? C22 C12 1.4973(17) . ? C22 H22 0.99(2) . ? C12 O22 1.2591(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C61 N11 N21 117.55(11) . . ? N11 N21 C31 122.46(11) . . ? N11 N21 H21 118.8 . . ? C31 N21 H21 118.8 . . ? N31 C31 N41 119.70(12) . . ? N31 C31 N21 118.71(12) . . ? N41 C31 N21 121.59(12) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C51 N41 C31 117.39(12) . . ? N51 C51 N41 118.65(12) . . ? N51 C51 C61 121.41(12) . . ? N41 C51 C61 119.93(12) . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? N11 C61 C51 120.19(12) . . ? N11 C61 C611 117.33(11) . . ? C51 C61 C611 122.41(11) . . ? C661 C611 C621 119.11(13) . . ? C661 C611 C61 119.59(12) . . ? C621 C611 C61 121.30(12) . . ? C631 C621 C611 119.93(14) . . ? C631 C621 Cl11 120.49(12) . . ? C611 C621 Cl11 119.58(11) . . ? C641 C631 C621 120.52(14) . . ? C641 C631 Cl21 118.46(13) . . ? C621 C631 Cl21 121.02(13) . . ? C651 C641 C631 119.76(15) . . ? C651 C641 H641 120.1 . . ? C631 C641 H641 120.1 . . ? C641 C651 C661 120.25(15) . . ? C641 C651 H651 119.9 . . ? C661 C651 H651 119.9 . . ? C651 C661 C611 120.41(14) . . ? C651 C661 H661 119.8 . . ? C611 C661 H661 119.8 . . ? O113 S113 C113 104.7(4) . . ? O113 S113 C213 103.3(4) . . ? C113 S113 C213 97.2(6) . . ? S113 C113 H11A 109.5 . . ? S113 C113 H11B 109.5 . . ? H11A C113 H11B 109.5 . . ? S113 C113 H11C 109.5 . . ? H11A C113 H11C 109.5 . . ? H11B C113 H11C 109.5 . . ? S113 C213 H21A 109.5 . . ? S113 C213 H21B 109.5 . . ? H21A C213 H21B 109.5 . . ? S113 C213 H21C 109.5 . . ? H21A C213 H21C 109.5 . . ? H21B C213 H21C 109.5 . . ? O123 S123 C123 96.2(9) . . ? O123 S123 C223 103.6(6) . . ? C123 S123 C223 97.7(8) . . ? S123 C123 H12A 109.5 . . ? S123 C123 H12B 109.5 . . ? H12A C123 H12B 109.5 . . ? S123 C123 H12C 109.5 . . ? H12A C123 H12C 109.5 . . ? H12B C123 H12C 109.5 . . ? S123 C223 H22A 109.5 . . ? S123 C223 H22B 109.5 . . ? H22A C223 H22B 109.5 . . ? S123 C223 H22C 109.5 . . ? H22A C223 H22C 109.5 . . ? H22B C223 H22C 109.5 . . ? C22 C22 C12 123.14(15) 3_565 . ? C22 C22 H22 119.8(12) 3_565 . ? C12 C22 H22 116.9(12) . . ? O22 C12 O12 124.30(12) . . ? O22 C12 C22 115.95(11) . . ? O12 C12 C22 119.75(11) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 33.73 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.759 _refine_diff_density_min -0.855 _refine_diff_density_rms 0.107 # Attachment '- LM+3(guest-free).cif' data_LM+3 _database_code_depnum_ccdc_archive 'CCDC 856204' #TrackingRef '- LM+3(guest-free).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - succinate (2:1) ; _chemical_name_common ;3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - succinate (2:1) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C4 H4 O4' _chemical_formula_sum 'C22 H20 Cl4 N10 O4' _chemical_formula_weight 630.28 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' Cl Cl 0.1484 0.1585 '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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.8921(4) _cell_length_b 9.2100(2) _cell_length_c 11.1833(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.290(10) _cell_angle_gamma 90.00 _cell_volume 1302.17(6) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 10861 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 0.507 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 0.937 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 11994 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2289 _reflns_number_gt 1969 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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^)+(0.0516P)^2^+1.3092P] 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 2289 _refine_ls_number_parameters 224 _refine_ls_number_restraints 29 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1305 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.196 _refine_ls_restrained_S_all 1.192 _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 C611 C 0.3323(2) 0.7911(4) 0.7724(3) 0.0294(7) Uani 0.939(2) 1 d PD A 1 C621 C 0.2932(2) 0.8920(4) 0.8454(3) 0.0324(7) Uani 0.939(2) 1 d PD A 1 C631 C 0.1860(3) 0.8922(4) 0.8522(3) 0.0385(8) Uani 0.939(2) 1 d PD A 1 C641 C 0.1186(2) 0.7887(4) 0.7887(3) 0.0422(9) Uani 0.939(2) 1 d PD A 1 H641 H 0.0460 0.7875 0.7943 0.051 Uiso 0.939(2) 1 calc PR A 1 C651 C 0.1569(3) 0.6875(4) 0.7175(3) 0.0447(9) Uani 0.939(2) 1 d PD A 1 H651 H 0.1109 0.6160 0.6750 0.054 Uiso 0.939(2) 1 calc PR A 1 C661 C 0.2638(3) 0.6898(4) 0.7078(3) 0.0391(8) Uani 0.939(2) 1 d PD A 1 H661 H 0.2893 0.6216 0.6568 0.047 Uiso 0.939(2) 1 calc PR A 1 Cl11 Cl 0.37809(7) 1.01711(10) 0.92819(8) 0.0445(3) Uani 0.939(2) 1 d PD A 1 Cl21 Cl 0.13618(7) 1.02140(11) 0.93826(9) 0.0550(3) Uani 0.939(2) 1 d PD A 1 N11 N 0.51932(19) 0.7441(3) 0.8384(2) 0.0306(6) Uani 0.939(2) 1 d P A 1 N21 N 0.6195(2) 0.7559(3) 0.8188(3) 0.0284(6) Uani 0.939(2) 1 d P A 1 H21 H 0.6712 0.7181 0.8731 0.034 Uiso 0.939(2) 1 calc PR A 1 C31 C 0.6441(4) 0.8224(4) 0.7208(5) 0.0262(6) Uani 0.939(2) 1 d P A 1 N41 N 0.5689(6) 0.8820(3) 0.6339(3) 0.0280(5) Uani 0.939(2) 1 d P A 1 C51 C 0.4699(5) 0.8677(3) 0.6469(4) 0.0273(7) Uani 0.939(2) 1 d P A 1 C61 C 0.4452(3) 0.7978(3) 0.7564(3) 0.0276(7) Uani 0.939(2) 1 d P A 1 N31 N 0.74405(17) 0.8303(3) 0.7096(2) 0.0324(6) Uani 0.939(2) 1 d PD A 1 H31A H 0.7939 0.7923 0.7660 0.039 Uiso 0.939(2) 1 calc PR A 1 H31B H 0.7608 0.8736 0.6459 0.039 Uiso 0.939(2) 1 calc PR A 1 N51 N 0.39268(18) 0.9181(3) 0.5619(2) 0.0337(6) Uani 0.939(2) 1 d PD A 1 H51A H 0.4073 0.9610 0.4969 0.040 Uiso 0.939(2) 1 calc PR A 1 H51B H 0.3265 0.9088 0.5701 0.040 Uiso 0.939(2) 1 calc PR A 1 C612 C 0.353(2) 0.843(3) 0.800(3) 0.0294(7) Uani 0.061(2) 1 d PD A 2 C622 C 0.272(2) 0.758(2) 0.741(2) 0.0324(7) Uani 0.061(2) 1 d PD A 2 C632 C 0.1677(18) 0.775(3) 0.761(2) 0.0385(8) Uani 0.061(2) 1 d PD A 2 C642 C 0.146(3) 0.879(5) 0.842(4) 0.0422(9) Uani 0.061(2) 1 d PD A 2 H642 H 0.0769 0.8895 0.8570 0.051 Uiso 0.061(2) 1 calc PR A 2 C652 C 0.227(3) 0.967(4) 0.901(4) 0.0447(9) Uani 0.061(2) 1 d PD A 2 H652 H 0.2137 1.0369 0.9586 0.054 Uiso 0.061(2) 1 calc PR A 2 C662 C 0.330(3) 0.952(4) 0.878(4) 0.0391(8) Uani 0.061(2) 1 d PD A 2 H662 H 0.3841 1.0169 0.9144 0.047 Uiso 0.061(2) 1 calc PR A 2 Cl12 Cl 0.3035(11) 0.6334(14) 0.6406(12) 0.045(4) Uani 0.061(2) 1 d PD A 2 Cl22 Cl 0.0700(11) 0.6670(17) 0.6830(14) 0.056(5) Uani 0.061(2) 1 d PD A 2 N12 N 0.536(3) 0.802(3) 0.859(4) 0.0306(6) Uani 0.061(2) 1 d PGD A 2 N22 N 0.637(3) 0.799(3) 0.834(5) 0.0284(6) Uani 0.061(2) 1 d PGD A 2 H22 H 0.6915 0.7742 0.8912 0.034 Uiso 0.061(2) 1 calc PR A 2 C32 C 0.654(6) 0.837(3) 0.719(6) 0.0262(6) Uani 0.061(2) 1 d PGD A 2 N42 N 0.568(8) 0.877(2) 0.628(4) 0.0280(5) Uani 0.061(2) 1 d PGD A 2 C52 C 0.467(7) 0.8793(15) 0.653(4) 0.0273(7) Uani 0.061(2) 1 d PGD A 2 C62 C 0.451(3) 0.842(3) 0.768(6) 0.0276(7) Uani 0.061(2) 1 d PGD A 2 N32 N 0.74405(17) 0.8303(3) 0.7096(2) 0.0324(6) Uani 0.061(2) 1 d P A 2 H32A H 0.7624 0.8522 0.6400 0.039 Uiso 0.061(2) 1 calc PR A 2 H32B H 0.7925 0.8037 0.7726 0.039 Uiso 0.061(2) 1 calc PR A 2 N52 N 0.39268(18) 0.9181(3) 0.5619(2) 0.0337(6) Uani 0.061(2) 1 d P A 2 H52A H 0.3265 0.9220 0.5712 0.040 Uiso 0.061(2) 1 calc PR A 2 H52B H 0.4087 0.9404 0.4911 0.040 Uiso 0.061(2) 1 calc PR A 2 O12 O 0.90037(16) 0.6954(3) 0.8740(2) 0.0490(6) Uani 1 1 d . . . O22 O 0.77547(14) 0.6074(2) 0.96540(17) 0.0317(5) Uani 1 1 d . . . C12 C 0.8700(2) 0.6103(3) 0.9456(2) 0.0298(6) Uani 1 1 d . . . C22 C 0.9463(2) 0.5024(3) 1.0173(3) 0.0326(7) Uani 1 1 d . . . H22A H 0.9558 0.5266 1.1050 0.039 Uiso 1 1 calc R . . H22B H 0.9143 0.4044 1.0057 0.039 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 C611 0.0192(15) 0.0373(18) 0.0314(16) 0.0101(13) 0.0042(12) 0.0016(13) C621 0.0226(15) 0.0374(18) 0.0373(17) 0.0098(14) 0.0058(13) 0.0022(13) C631 0.0271(17) 0.048(2) 0.0448(19) 0.0141(16) 0.0166(16) 0.0082(16) C641 0.0208(16) 0.056(2) 0.052(2) 0.0154(17) 0.0107(15) -0.0010(15) C651 0.0279(19) 0.053(2) 0.053(2) 0.0072(17) 0.0062(16) -0.0110(16) C661 0.0293(17) 0.044(2) 0.046(2) 0.0037(16) 0.0112(15) -0.0031(15) Cl11 0.0331(5) 0.0463(5) 0.0548(5) -0.0079(4) 0.0105(4) -0.0004(4) Cl21 0.0428(5) 0.0617(6) 0.0679(6) 0.0065(5) 0.0289(4) 0.0172(4) N11 0.0193(13) 0.0386(17) 0.0347(14) 0.0077(12) 0.0070(11) 0.0037(12) N21 0.0175(13) 0.0382(16) 0.0287(15) 0.0057(13) 0.0024(11) 0.0040(11) C31 0.0221(17) 0.0274(15) 0.0290(14) 0.0000(12) 0.0047(11) 0.0020(11) N41 0.0193(11) 0.0366(13) 0.0279(12) 0.0054(10) 0.0041(10) 0.0041(10) C51 0.0231(14) 0.0286(15) 0.0310(15) 0.0020(12) 0.0069(12) 0.0027(12) C61 0.0220(14) 0.0308(17) 0.0308(16) 0.0047(16) 0.0071(12) 0.0041(14) N31 0.0200(12) 0.0447(15) 0.0318(13) 0.0090(11) 0.0037(9) 0.0046(10) N51 0.0196(12) 0.0487(15) 0.0333(13) 0.0131(11) 0.0066(10) 0.0043(11) C612 0.0192(15) 0.0373(18) 0.0314(16) 0.0101(13) 0.0042(12) 0.0016(13) C622 0.0226(15) 0.0374(18) 0.0373(17) 0.0098(14) 0.0058(13) 0.0022(13) C632 0.0271(17) 0.048(2) 0.0448(19) 0.0141(16) 0.0166(16) 0.0082(16) C642 0.0208(16) 0.056(2) 0.052(2) 0.0154(17) 0.0107(15) -0.0010(15) C652 0.0279(19) 0.053(2) 0.053(2) 0.0072(17) 0.0062(16) -0.0110(16) C662 0.0293(17) 0.044(2) 0.046(2) 0.0037(16) 0.0112(15) -0.0031(15) Cl12 0.053(8) 0.040(7) 0.042(7) -0.011(6) 0.009(6) 0.000(6) Cl22 0.036(8) 0.065(10) 0.063(9) 0.002(7) -0.001(6) -0.024(7) N12 0.0193(13) 0.0386(17) 0.0347(14) 0.0077(12) 0.0070(11) 0.0037(12) N22 0.0175(13) 0.0382(16) 0.0287(15) 0.0057(13) 0.0024(11) 0.0040(11) C32 0.0221(17) 0.0274(15) 0.0290(14) 0.0000(12) 0.0047(11) 0.0020(11) N42 0.0193(11) 0.0366(13) 0.0279(12) 0.0054(10) 0.0041(10) 0.0041(10) C52 0.0231(14) 0.0286(15) 0.0310(15) 0.0020(12) 0.0069(12) 0.0027(12) C62 0.0220(14) 0.0308(17) 0.0308(16) 0.0047(16) 0.0071(12) 0.0041(14) N32 0.0200(12) 0.0447(15) 0.0318(13) 0.0090(11) 0.0037(9) 0.0046(10) N52 0.0196(12) 0.0487(15) 0.0333(13) 0.0131(11) 0.0066(10) 0.0043(11) O12 0.0213(10) 0.0678(16) 0.0597(14) 0.0352(13) 0.0126(10) 0.0084(10) O22 0.0159(9) 0.0448(12) 0.0344(11) 0.0060(9) 0.0051(8) 0.0029(8) C12 0.0190(13) 0.0382(16) 0.0314(15) 0.0027(12) 0.0032(11) 0.0016(12) C22 0.0185(14) 0.0435(17) 0.0362(15) 0.0107(13) 0.0059(11) 0.0044(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 C611 C661 1.386(5) . ? C611 C621 1.395(5) . ? C611 C61 1.501(5) . ? C621 C631 1.400(4) . ? C621 Cl11 1.728(3) . ? C631 C641 1.389(5) . ? C631 Cl21 1.731(4) . ? C641 C651 1.378(5) . ? C641 H641 0.9500 . ? C651 C661 1.403(5) . ? C651 H651 0.9500 . ? C661 H661 0.9500 . ? N11 C61 1.287(4) . ? N11 N21 1.356(3) . ? N21 C31 1.347(4) . ? N21 H21 0.8800 . ? C31 N31 1.321(5) . ? C31 N41 1.348(4) . ? N41 C51 1.319(4) . ? C51 N51 1.319(5) . ? C51 C61 1.473(4) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C612 C622 1.367(18) . ? C612 C62 1.38(6) . ? C612 C662 1.397(19) . ? C622 C632 1.410(18) . ? C622 Cl12 1.708(18) . ? C632 C642 1.382(19) . ? C632 Cl22 1.705(18) . ? C642 C652 1.384(19) . ? C642 H642 0.9500 . ? C652 C662 1.404(19) . ? C652 H652 0.9500 . ? C662 H662 0.9500 . ? N12 N22 1.3900 . ? N12 C62 1.3900 . ? N22 C32 1.3900 . ? N22 H22 0.8800 . ? C32 N42 1.3900 . ? N42 C52 1.3900 . ? C52 C62 1.3900 . ? O12 C12 1.237(4) . ? O22 C12 1.281(3) . ? C12 C22 1.513(4) . ? C22 C22 1.510(5) 3_767 ? C22 H22A 0.9900 . ? C22 H22B 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 C661 C611 C621 119.1(3) . . ? C661 C611 C61 119.9(3) . . ? C621 C611 C61 120.8(3) . . ? C611 C621 C631 120.5(3) . . ? C611 C621 Cl11 119.6(2) . . ? C631 C621 Cl11 119.9(3) . . ? C641 C631 C621 119.8(3) . . ? C641 C631 Cl21 119.6(3) . . ? C621 C631 Cl21 120.6(3) . . ? C651 C641 C631 120.0(3) . . ? C651 C641 H641 120.0 . . ? C631 C641 H641 120.0 . . ? C641 C651 C661 120.2(3) . . ? C641 C651 H651 119.9 . . ? C661 C651 H651 119.9 . . ? C611 C661 C651 120.3(3) . . ? C611 C661 H661 119.8 . . ? C651 C661 H661 119.8 . . ? C61 N11 N21 116.9(2) . . ? C31 N21 N11 123.5(2) . . ? C31 N21 H21 118.3 . . ? N11 N21 H21 118.3 . . ? N31 C31 N21 119.4(4) . . ? N31 C31 N41 119.1(4) . . ? N21 C31 N41 121.5(3) . . ? C51 N41 C31 117.0(2) . . ? N41 C51 N51 119.6(5) . . ? N41 C51 C61 120.5(3) . . ? N51 C51 C61 119.9(5) . . ? N11 C61 C51 120.6(3) . . ? N11 C61 C611 120.1(3) . . ? C51 C61 C611 119.3(3) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? C622 C612 C62 122(2) . . ? C622 C612 C662 119(2) . . ? C62 C612 C662 118.6(19) . . ? C612 C622 C632 121.3(18) . . ? C612 C622 Cl12 116.3(17) . . ? C632 C622 Cl12 122.4(18) . . ? C642 C632 C622 119.9(18) . . ? C642 C632 Cl22 121.1(19) . . ? C622 C632 Cl22 119.0(18) . . ? C632 C642 C652 119(2) . . ? C632 C642 H642 120.3 . . ? C652 C642 H642 120.3 . . ? C642 C652 C662 120(2) . . ? C642 C652 H652 120.0 . . ? C662 C652 H652 120.0 . . ? C612 C662 C652 121(2) . . ? C612 C662 H662 119.7 . . ? C652 C662 H662 119.7 . . ? N22 N12 C62 120.0 . . ? N12 N22 C32 120.0 . . ? N12 N22 H22 120.0 . . ? C32 N22 H22 120.0 . . ? N42 C32 N22 120.0 . . ? C32 N42 C52 120.0 . . ? C62 C52 N42 120.0 . . ? C612 C62 C52 124(5) . . ? C612 C62 N12 116(5) . . ? C52 C62 N12 120.0 . . ? O12 C12 O22 123.9(3) . . ? O12 C12 C22 120.2(2) . . ? O22 C12 C22 115.9(2) . . ? C22 C22 C12 114.7(3) 3_767 . ? C22 C22 H22A 108.6 3_767 . ? C12 C22 H22A 108.6 . . ? C22 C22 H22B 108.6 3_767 . ? C12 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? 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 C661 C611 C621 C631 -0.8(5) . . . . ? C61 C611 C621 C631 175.0(3) . . . . ? C661 C611 C621 Cl11 179.0(2) . . . . ? C61 C611 C621 Cl11 -5.2(4) . . . . ? C611 C621 C631 C641 1.9(5) . . . . ? Cl11 C621 C631 C641 -177.9(2) . . . . ? C611 C621 C631 Cl21 -177.6(2) . . . . ? Cl11 C621 C631 Cl21 2.6(4) . . . . ? C621 C631 C641 C651 -1.1(5) . . . . ? Cl21 C631 C641 C651 178.4(3) . . . . ? C631 C641 C651 C661 -0.8(5) . . . . ? C621 C611 C661 C651 -1.0(5) . . . . ? C61 C611 C661 C651 -176.9(3) . . . . ? C641 C651 C661 C611 1.9(5) . . . . ? C61 N11 N21 C31 1.4(4) . . . . ? N11 N21 C31 N31 179.3(3) . . . . ? N11 N21 C31 N41 -0.3(4) . . . . ? N31 C31 N41 C51 178.0(3) . . . . ? N21 C31 N41 C51 -2.4(4) . . . . ? C31 N41 C51 N51 -177.0(3) . . . . ? C31 N41 C51 C61 3.9(4) . . . . ? N21 N11 C61 C51 0.2(4) . . . . ? N21 N11 C61 C611 -179.0(3) . . . . ? N41 C51 C61 N11 -3.0(5) . . . . ? N51 C51 C61 N11 177.9(3) . . . . ? N41 C51 C61 C611 176.3(3) . . . . ? N51 C51 C61 C611 -2.8(4) . . . . ? C661 C611 C61 N11 -103.2(4) . . . . ? C621 C611 C61 N11 81.1(4) . . . . ? C661 C611 C61 C51 77.5(4) . . . . ? C621 C611 C61 C51 -98.2(4) . . . . ? C62 C612 C622 C632 -170(3) . . . . ? C662 C612 C622 C632 -3(2) . . . . ? C62 C612 C622 Cl12 9(3) . . . . ? C662 C612 C622 Cl12 176(3) . . . . ? C612 C622 C632 C642 0(3) . . . . ? Cl12 C622 C632 C642 -179(3) . . . . ? C612 C622 C632 Cl22 179.7(19) . . . . ? Cl12 C622 C632 Cl22 1(2) . . . . ? C622 C632 C642 C652 1(5) . . . . ? Cl22 C632 C642 C652 -179(4) . . . . ? C632 C642 C652 C662 1(7) . . . . ? C622 C612 C662 C652 5(5) . . . . ? C62 C612 C662 C652 173(4) . . . . ? C642 C652 C662 C612 -4(6) . . . . ? C62 N12 N22 C32 0.0 . . . . ? N12 N22 C32 N42 0.0 . . . . ? N22 C32 N42 C52 0.0 . . . . ? C32 N42 C52 C62 0.0 . . . . ? C622 C612 C62 C52 60(2) . . . . ? C662 C612 C62 C52 -108(3) . . . . ? C622 C612 C62 N12 -121(2) . . . . ? C662 C612 C62 N12 72(3) . . . . ? N42 C52 C62 C612 179.7(6) . . . . ? N42 C52 C62 N12 0.0 . . . . ? N22 N12 C62 C612 -179.7(6) . . . . ? N22 N12 C62 C52 0.0 . . . . ? O12 C12 C22 C22 -6.8(5) . . . 3_767 ? O22 C12 C22 C22 174.0(3) . . . 3_767 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N21 H21 O22 0.88 1.84 2.704(3) 168.4 . N31 H31A O12 0.88 1.87 2.745(3) 173.9 . N31 H31B O22 0.88 2.07 2.896(3) 155.8 4_575 N51 H51A N41 0.88 2.12 2.975(4) 163.6 3_676 N51 H51B O22 0.88 2.24 2.752(3) 116.7 2_656 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.203 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.067 # Attachment '- LM+3.(DMSO).CIF' data_LM+3.(DMSO) _database_code_depnum_ccdc_archive 'CCDC 856205' #TrackingRef '- LM+3.(DMSO).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - succinate - dimethyl sulfoxide (1:0.5:1) ; _chemical_name_common ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - succinate -dimethyl sulfoxide (1:0.5:1) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C4 H4 O4, 2(C2 H6 O S)' _chemical_formula_sum 'C26 H32 Cl4 N10 O6 S2' _chemical_formula_weight 786.54 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' 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0200(2) _cell_length_b 10.6723(2) _cell_length_c 15.9451(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.8400(10) _cell_angle_gamma 90.00 _cell_volume 1774.81(6) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 10772 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 32.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 0.506 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 0.937 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 18322 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 32.04 _reflns_number_total 6129 _reflns_number_gt 5081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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^)+(0.0491P)^2^+0.8512P] 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 6129 _refine_ls_number_parameters 259 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 S113 S 0.74794(7) 0.99530(8) 0.82613(5) 0.04251(17) Uani 0.60 1 d PD A 1 C113 C 0.8185(14) 0.8512(8) 0.8745(10) 0.067(3) Uani 0.60 1 d PD A 1 H11A H 0.7879 0.7832 0.8315 0.100 Uiso 0.60 1 calc PR A 1 H11B H 0.7943 0.8338 0.9273 0.100 Uiso 0.60 1 calc PR A 1 H11C H 0.9120 0.8574 0.8912 0.100 Uiso 0.60 1 calc PR A 1 C213 C 0.8237(13) 1.0954(8) 0.9166(5) 0.060(2) Uani 0.60 1 d PD A 1 H21A H 0.7982 1.1823 0.9001 0.090 Uiso 0.60 1 calc PR A 1 H21B H 0.9170 1.0877 0.9319 0.090 Uiso 0.60 1 calc PR A 1 H21C H 0.7979 1.0715 0.9677 0.090 Uiso 0.60 1 calc PR A 1 O113 O 0.8134(6) 1.0248(5) 0.7575(3) 0.0372(8) Uani 0.60 1 d PD A 1 S123 S 0.87076(10) 0.99271(12) 0.85393(7) 0.0402(2) Uani 0.40 1 d PD B 2 C123 C 0.8020(19) 0.8538(14) 0.8790(16) 0.062(4) Uani 0.40 1 d PD B 2 H12A H 0.8152 0.7852 0.8421 0.093 Uiso 0.40 1 calc PR B 2 H12B H 0.7098 0.8665 0.8671 0.093 Uiso 0.40 1 calc PR B 2 H12C H 0.8427 0.8328 0.9416 0.093 Uiso 0.40 1 calc PR B 2 C223 C 0.809(2) 1.0995(17) 0.9150(12) 0.084(6) Uani 0.40 1 d PD B 2 H22D H 0.8361 1.1847 0.9065 0.126 Uiso 0.40 1 calc PR B 2 H22E H 0.8417 1.0778 0.9780 0.126 Uiso 0.40 1 calc PR B 2 H22C H 0.7152 1.0950 0.8942 0.126 Uiso 0.40 1 calc PR B 2 O123 O 0.7890(12) 1.0205(12) 0.7586(6) 0.078(4) Uani 0.40 1 d PD B 2 C641 C 0.94941(14) 0.75216(15) 0.18631(9) 0.0313(3) Uani 1 1 d . . . H641 H 1.0054 0.8049 0.2298 0.038 Uiso 1 1 calc R . . C651 C 0.82535(14) 0.79098(14) 0.14050(10) 0.0316(3) Uani 1 1 d . . . H651 H 0.7960 0.8701 0.1533 0.038 Uiso 1 1 calc R . . C661 C 0.74409(13) 0.71460(13) 0.07603(9) 0.0266(3) Uani 1 1 d . . . H661 H 0.6596 0.7421 0.0446 0.032 Uiso 1 1 calc R . . C51 C 0.63575(12) 0.40721(11) 0.01173(8) 0.0213(2) Uani 1 1 d . . . C631 C 0.99099(13) 0.63575(14) 0.16808(9) 0.0276(3) Uani 1 1 d . . . C31 C 0.55351(12) 0.36130(11) -0.13563(8) 0.0213(2) Uani 1 1 d . . . C621 C 0.90962(13) 0.55821(12) 0.10432(8) 0.0237(2) Uani 1 1 d . . . N31 N 0.49279(13) 0.28460(11) -0.20079(7) 0.0293(2) Uani 1 1 d . . . H31A H 0.4613 0.2135 -0.1890 0.035 Uiso 1 1 calc R . . H31B H 0.4839 0.3047 -0.2560 0.035 Uiso 1 1 calc R . . C611 C 0.78558(12) 0.59808(11) 0.05724(8) 0.0207(2) Uani 1 1 d . . . N51 N 0.64540(12) 0.38251(11) 0.09469(7) 0.0272(2) Uani 1 1 d . . . H51A H 0.6068 0.3164 0.1072 0.033 Uiso 1 1 calc R . . H51B H 0.6905 0.4322 0.1375 0.033 Uiso 1 1 calc R . . N11 N 0.67635(11) 0.54710(10) -0.09394(7) 0.0227(2) Uani 1 1 d . . . N41 N 0.56672(11) 0.33017(10) -0.05169(7) 0.0232(2) Uani 1 1 d . . . N21 N 0.59963(11) 0.47043(10) -0.15614(7) 0.0229(2) Uani 1 1 d . . . H21 H 0.5789 0.4924 -0.2122 0.027 Uiso 1 1 calc R . . C61 C 0.69793(12) 0.51644(11) -0.01148(8) 0.0208(2) Uani 1 1 d . . . Cl21 Cl 1.14531(4) 0.58832(5) 0.22653(3) 0.04634(12) Uani 1 1 d . . . Cl11 Cl 0.96025(4) 0.41185(4) 0.08272(3) 0.03685(10) Uani 1 1 d . . . C12 C 0.55541(12) 0.05666(11) 0.12093(7) 0.0200(2) Uani 1 1 d . . . C22 C 0.56342(12) 0.02857(12) 0.02942(7) 0.0217(2) Uani 1 1 d . . . H22B H 0.6345 -0.0307 0.0345 0.026 Uiso 1 1 calc R . . H22A H 0.5812 0.1068 0.0021 0.026 Uiso 1 1 calc R . . O12 O 0.52534(11) 0.16544(9) 0.13623(6) 0.0293(2) Uani 1 1 d . . . O22 O 0.57814(11) -0.03215(9) 0.17647(6) 0.0274(2) 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 S113 0.0349(3) 0.0481(4) 0.0455(4) 0.0027(3) 0.0143(3) -0.0006(3) C113 0.092(8) 0.047(4) 0.058(4) 0.023(3) 0.020(5) 0.011(4) C213 0.081(5) 0.066(5) 0.039(3) -0.011(3) 0.029(3) -0.020(4) O113 0.0444(14) 0.0423(16) 0.0253(15) 0.0031(11) 0.0116(11) -0.0027(12) S123 0.0388(5) 0.0539(6) 0.0317(4) 0.0137(4) 0.0168(4) 0.0062(4) C123 0.049(4) 0.073(9) 0.067(8) 0.021(6) 0.022(5) -0.009(5) C223 0.099(10) 0.094(11) 0.084(10) -0.028(8) 0.064(9) 0.005(8) O123 0.100(8) 0.105(6) 0.026(3) 0.019(3) 0.016(4) 0.040(5) C641 0.0299(6) 0.0325(7) 0.0270(6) -0.0049(5) 0.0031(5) -0.0060(5) C651 0.0321(7) 0.0238(6) 0.0356(7) -0.0077(5) 0.0062(5) -0.0001(5) C661 0.0251(6) 0.0217(6) 0.0301(6) -0.0019(5) 0.0050(5) 0.0019(5) C51 0.0285(6) 0.0183(5) 0.0171(5) 0.0015(4) 0.0073(4) 0.0001(4) C631 0.0227(6) 0.0333(7) 0.0243(6) 0.0040(5) 0.0041(4) 0.0007(5) C31 0.0290(6) 0.0173(5) 0.0180(5) 0.0013(4) 0.0083(4) -0.0008(4) C621 0.0273(6) 0.0218(5) 0.0231(5) 0.0035(4) 0.0098(4) 0.0039(5) N31 0.0477(7) 0.0227(5) 0.0173(5) -0.0011(4) 0.0100(4) -0.0104(5) C611 0.0249(5) 0.0186(5) 0.0185(5) 0.0009(4) 0.0069(4) -0.0003(4) N51 0.0405(6) 0.0240(5) 0.0170(4) 0.0011(4) 0.0093(4) -0.0070(5) N11 0.0308(5) 0.0180(4) 0.0197(4) 0.0008(4) 0.0088(4) -0.0013(4) N41 0.0334(6) 0.0194(5) 0.0172(4) 0.0005(4) 0.0086(4) -0.0039(4) N21 0.0346(6) 0.0183(4) 0.0155(4) 0.0015(3) 0.0078(4) -0.0035(4) C61 0.0268(6) 0.0165(5) 0.0190(5) 0.0007(4) 0.0074(4) 0.0000(4) Cl21 0.02634(18) 0.0567(3) 0.0459(2) 0.00775(19) -0.00218(15) 0.00583(16) Cl11 0.0420(2) 0.02825(17) 0.0407(2) 0.00300(13) 0.01403(15) 0.01347(14) C12 0.0244(5) 0.0199(5) 0.0151(5) -0.0011(4) 0.0057(4) -0.0030(4) C22 0.0274(6) 0.0229(5) 0.0154(5) -0.0007(4) 0.0078(4) 0.0001(4) O12 0.0499(6) 0.0198(4) 0.0234(4) 0.0025(3) 0.0192(4) 0.0044(4) O22 0.0464(6) 0.0190(4) 0.0161(4) 0.0007(3) 0.0092(4) -0.0006(4) _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 S113 O113 1.525(5) . ? S113 C213 1.772(7) . ? S113 C113 1.782(8) . ? C113 H11A 0.9800 . ? C113 H11B 0.9800 . ? C113 H11C 0.9800 . ? C213 H21A 0.9800 . ? C213 H21B 0.9800 . ? C213 H21C 0.9800 . ? S123 O123 1.525(10) . ? S123 C123 1.768(12) . ? S123 C223 1.771(12) . ? C123 H12A 0.9800 . ? C123 H12B 0.9800 . ? C123 H12C 0.9800 . ? C223 H22D 0.9800 . ? C223 H22E 0.9800 . ? C223 H22C 0.9800 . ? C641 C631 1.387(2) . ? C641 C651 1.389(2) . ? C641 H641 0.9500 . ? C651 C661 1.3887(19) . ? C651 H651 0.9500 . ? C661 C611 1.3906(18) . ? C661 H661 0.9500 . ? C51 N51 1.3189(15) . ? C51 N41 1.3343(16) . ? C51 C61 1.4593(17) . ? C631 C621 1.3906(19) . ? C631 Cl21 1.7300(14) . ? C31 N31 1.3222(16) . ? C31 N41 1.3407(15) . ? C31 N21 1.3524(15) . ? C621 C611 1.3966(18) . ? C621 Cl11 1.7303(13) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? C611 C61 1.4863(17) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? N11 C61 1.3001(15) . ? N11 N21 1.3515(15) . ? N21 H21 0.8800 . ? C12 O12 1.2527(15) . ? C12 O22 1.2657(15) . ? C12 C22 1.5198(16) . ? C22 C22 1.536(2) 3_655 ? C22 H22B 0.9900 . ? C22 H22A 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 O113 S113 C213 104.6(4) . . ? O113 S113 C113 104.3(5) . . ? C213 S113 C113 98.2(6) . . ? O123 S123 C123 103.3(9) . . ? O123 S123 C223 102.4(9) . . ? C123 S123 C223 98.4(9) . . ? S123 C123 H12A 109.5 . . ? S123 C123 H12B 109.5 . . ? H12A C123 H12B 109.5 . . ? S123 C123 H12C 109.5 . . ? H12A C123 H12C 109.5 . . ? H12B C123 H12C 109.5 . . ? S123 C223 H22D 109.5 . . ? S123 C223 H22E 109.5 . . ? H22D C223 H22E 109.5 . . ? S123 C223 H22C 109.5 . . ? H22D C223 H22C 109.5 . . ? H22E C223 H22C 109.5 . . ? C631 C641 C651 119.52(13) . . ? C631 C641 H641 120.2 . . ? C651 C641 H641 120.2 . . ? C661 C651 C641 120.27(13) . . ? C661 C651 H651 119.9 . . ? C641 C651 H651 119.9 . . ? C651 C661 C611 120.41(13) . . ? C651 C661 H661 119.8 . . ? C611 C661 H661 119.8 . . ? N51 C51 N41 118.59(11) . . ? N51 C51 C61 121.44(11) . . ? N41 C51 C61 119.96(10) . . ? C641 C631 C621 120.50(12) . . ? C641 C631 Cl21 118.88(11) . . ? C621 C631 Cl21 120.62(11) . . ? N31 C31 N41 119.69(11) . . ? N31 C31 N21 118.52(11) . . ? N41 C31 N21 121.79(11) . . ? C631 C621 C611 119.99(12) . . ? C631 C621 Cl11 120.63(10) . . ? C611 C621 Cl11 119.38(10) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C661 C611 C621 119.30(12) . . ? C661 C611 C61 120.17(11) . . ? C621 C611 C61 120.52(11) . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? C61 N11 N21 117.17(11) . . ? C51 N41 C31 117.10(11) . . ? N11 N21 C31 122.60(10) . . ? N11 N21 H21 118.7 . . ? C31 N21 H21 118.7 . . ? N11 C61 C51 120.67(11) . . ? N11 C61 C611 117.46(11) . . ? C51 C61 C611 121.86(10) . . ? O12 C12 O22 124.24(11) . . ? O12 C12 C22 118.09(11) . . ? O22 C12 C22 117.67(11) . . ? C12 C22 C22 109.95(12) . 3_655 ? C12 C22 H22B 109.7 . . ? C22 C22 H22B 109.7 3_655 . ? C12 C22 H22A 109.7 . . ? C22 C22 H22A 109.7 3_655 . ? H22B C22 H22A 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 C631 C641 C651 C661 -0.9(2) . . . . ? C641 C651 C661 C611 0.6(2) . . . . ? C651 C641 C631 C621 0.2(2) . . . . ? C651 C641 C631 Cl21 -179.39(12) . . . . ? C641 C631 C621 C611 0.9(2) . . . . ? Cl21 C631 C621 C611 -179.58(10) . . . . ? C641 C631 C621 Cl11 -178.90(11) . . . . ? Cl21 C631 C621 Cl11 0.65(16) . . . . ? C651 C661 C611 C621 0.4(2) . . . . ? C651 C661 C611 C61 179.66(13) . . . . ? C631 C621 C611 C661 -1.16(19) . . . . ? Cl11 C621 C611 C661 178.61(10) . . . . ? C631 C621 C611 C61 179.61(12) . . . . ? Cl11 C621 C611 C61 -0.61(16) . . . . ? N51 C51 N41 C31 176.76(12) . . . . ? C61 C51 N41 C31 -2.88(18) . . . . ? N31 C31 N41 C51 175.89(12) . . . . ? N21 C31 N41 C51 -4.82(19) . . . . ? C61 N11 N21 C31 -4.70(18) . . . . ? N31 C31 N21 N11 -171.54(12) . . . . ? N41 C31 N21 N11 9.2(2) . . . . ? N21 N11 C61 C51 -3.13(18) . . . . ? N21 N11 C61 C611 178.08(11) . . . . ? N51 C51 C61 N11 -172.52(13) . . . . ? N41 C51 C61 N11 7.10(19) . . . . ? N51 C51 C61 C611 6.22(19) . . . . ? N41 C51 C61 C611 -174.15(12) . . . . ? C661 C611 C61 N11 74.55(16) . . . . ? C621 C611 C61 N11 -106.23(14) . . . . ? C661 C611 C61 C51 -104.23(15) . . . . ? C621 C611 C61 C51 74.99(16) . . . . ? O12 C12 C22 C22 -95.56(16) . . . 3_655 ? O22 C12 C22 C22 83.59(16) . . . 3_655 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 32.04 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.502 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.107 # Attachment '- LM+3.(ACON).CIF' data_LM+3.(ACON) _database_code_depnum_ccdc_archive 'CCDC 856206' #TrackingRef '- LM+3.(ACON).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - succinate - acetone (1:0.5:1) ; _chemical_name_common ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - succinate -acetone (1:0.5:1) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C4 H4 O4, 2(C3 H6 O)' _chemical_formula_sum 'C28 H32 Cl4 N10 O6' _chemical_formula_weight 746.43 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.8143(3) _cell_length_b 10.7320(3) _cell_length_c 16.0105(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.5600(10) _cell_angle_gamma 90.00 _cell_volume 1761.52(8) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 13265 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 33.14 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.391 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.888 _exptl_absorpt_correction_T_max 0.956 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 13658 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 33.16 _reflns_number_total 6590 _reflns_number_gt 4946 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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^)+(0.0342P)^2^+1.0480P] 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 6590 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1262 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 Cl11 Cl 0.03779(5) 0.08859(4) 0.41497(3) 0.04030(11) Uani 1 1 d . . . Cl21 Cl -0.14310(4) -0.08503(5) 0.26789(3) 0.05050(14) Uani 1 1 d . . . N11 N 0.32439(13) -0.04684(11) 0.59699(8) 0.0254(2) Uani 1 1 d . . . N21 N 0.40231(13) 0.03003(11) 0.65834(7) 0.0254(2) Uani 1 1 d . . . H21 H 0.4234 0.0087 0.7142 0.030 Uiso 1 1 calc R . . C31 C 0.44902(15) 0.13820(13) 0.63740(9) 0.0244(3) Uani 1 1 d . . . N31 N 0.51115(15) 0.21497(12) 0.70147(8) 0.0324(3) Uani 1 1 d . . . H31A H 0.5428 0.2856 0.6890 0.039 Uiso 1 1 calc R . . H31B H 0.5209 0.1955 0.7566 0.039 Uiso 1 1 calc R . . N41 N 0.43476(13) 0.16876(11) 0.55363(8) 0.0263(2) Uani 1 1 d . . . C51 C 0.36516(14) 0.09172(13) 0.49133(9) 0.0239(3) Uani 1 1 d . . . N51 N 0.35595(14) 0.11517(12) 0.40844(8) 0.0300(3) Uani 1 1 d . . . H51A H 0.3954 0.1806 0.3955 0.036 Uiso 1 1 calc R . . H51B H 0.3103 0.0653 0.3662 0.036 Uiso 1 1 calc R . . C61 C 0.30215(14) -0.01713(13) 0.51487(9) 0.0240(3) Uani 1 1 d . . . C611 C 0.21416(14) -0.09887(13) 0.44688(9) 0.0240(3) Uani 1 1 d . . . C621 C 0.09035(15) -0.05790(14) 0.39597(9) 0.0267(3) Uani 1 1 d . . . C631 C 0.01036(15) -0.13451(16) 0.33139(10) 0.0314(3) Uani 1 1 d . . . C641 C 0.05245(17) -0.25174(17) 0.31634(11) 0.0351(3) Uani 1 1 d . . . H641 H -0.0026 -0.3040 0.2721 0.042 Uiso 1 1 calc R . . C651 C 0.17528(17) -0.29242(16) 0.36620(12) 0.0364(4) Uani 1 1 d . . . H651 H 0.2047 -0.3725 0.3556 0.044 Uiso 1 1 calc R . . C661 C 0.25558(15) -0.21705(14) 0.43146(10) 0.0298(3) Uani 1 1 d . . . H661 H 0.3393 -0.2462 0.4658 0.036 Uiso 1 1 calc R . . O12 O 0.47622(13) 0.33078(10) 0.36433(7) 0.0330(3) Uani 1 1 d . . . O22 O 0.43146(13) 0.52925(10) 0.32660(6) 0.0320(2) Uani 1 1 d . . . C12 C 0.44884(14) 0.43969(13) 0.38052(8) 0.0225(2) Uani 1 1 d . . . C22 C 0.43829(14) 0.46706(13) 0.47119(8) 0.0242(3) Uani 1 1 d . . . H22A H 0.4262 0.3881 0.4996 0.029 Uiso 1 1 calc R . . H22B H 0.3614 0.5206 0.4652 0.029 Uiso 1 1 calc R . . O13 O 0.2134(2) 0.0080(2) 0.24023(11) 0.0844(6) Uani 1 1 d . . . C13 C 0.1983(2) -0.0078(2) 0.16362(13) 0.0470(5) Uani 1 1 d . . . C23 C 0.1780(3) -0.1351(3) 0.1257(2) 0.0780(8) Uani 1 1 d . . . H23A H 0.1856 -0.1959 0.1727 0.117 Uiso 1 1 calc R . . H23B H 0.2441 -0.1526 0.0972 0.117 Uiso 1 1 calc R . . H23C H 0.0909 -0.1408 0.0820 0.117 Uiso 1 1 calc R . . C33 C 0.2004(4) 0.0978(3) 0.1042(2) 0.0884(10) Uani 1 1 d . . . H33A H 0.2159 0.1757 0.1379 0.133 Uiso 1 1 calc R . . H33B H 0.1164 0.1025 0.0571 0.133 Uiso 1 1 calc R . . H33C H 0.2703 0.0848 0.0784 0.133 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 Cl11 0.0453(2) 0.0323(2) 0.0433(2) 0.00425(17) 0.01409(18) 0.01480(17) Cl21 0.0324(2) 0.0606(3) 0.0467(3) 0.0098(2) -0.00403(18) 0.0066(2) N11 0.0343(6) 0.0219(5) 0.0203(5) 0.0010(4) 0.0088(5) -0.0009(5) N21 0.0379(6) 0.0212(5) 0.0163(5) 0.0018(4) 0.0075(4) -0.0025(5) C31 0.0337(7) 0.0211(6) 0.0189(5) 0.0011(5) 0.0089(5) 0.0008(5) N31 0.0518(8) 0.0261(6) 0.0183(5) -0.0021(5) 0.0100(5) -0.0098(6) N41 0.0388(7) 0.0230(5) 0.0177(5) 0.0016(4) 0.0095(5) -0.0023(5) C51 0.0320(7) 0.0218(6) 0.0180(5) 0.0015(5) 0.0079(5) 0.0021(5) N51 0.0458(8) 0.0273(6) 0.0168(5) -0.0002(4) 0.0098(5) -0.0058(5) C61 0.0303(7) 0.0218(6) 0.0199(6) 0.0016(5) 0.0080(5) 0.0019(5) C611 0.0285(6) 0.0234(6) 0.0201(6) 0.0013(5) 0.0076(5) 0.0007(5) C621 0.0308(7) 0.0260(6) 0.0243(6) 0.0045(5) 0.0101(5) 0.0050(5) C631 0.0267(7) 0.0390(8) 0.0249(6) 0.0057(6) 0.0029(5) 0.0012(6) C641 0.0348(8) 0.0374(8) 0.0283(7) -0.0046(6) 0.0031(6) -0.0050(7) C651 0.0375(8) 0.0282(7) 0.0387(8) -0.0080(7) 0.0053(7) 0.0006(6) C661 0.0293(7) 0.0255(7) 0.0303(7) -0.0022(6) 0.0034(6) 0.0021(5) O12 0.0547(7) 0.0243(5) 0.0247(5) 0.0028(4) 0.0195(5) 0.0055(5) O22 0.0563(7) 0.0222(5) 0.0169(4) 0.0000(4) 0.0107(4) -0.0032(5) C12 0.0274(6) 0.0241(6) 0.0152(5) -0.0002(5) 0.0056(4) -0.0026(5) C22 0.0310(7) 0.0257(6) 0.0165(5) -0.0002(5) 0.0081(5) -0.0002(5) O13 0.0989(15) 0.1145(17) 0.0391(8) -0.0312(10) 0.0208(9) -0.0173(13) C13 0.0414(10) 0.0644(13) 0.0371(9) -0.0152(9) 0.0153(8) -0.0084(9) C23 0.096(2) 0.0734(18) 0.0644(16) -0.0226(15) 0.0258(15) -0.0129(16) C33 0.105(2) 0.080(2) 0.107(3) 0.0120(18) 0.072(2) 0.0028(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl11 C621 1.7312(15) . ? Cl21 C631 1.7308(16) . ? N11 C61 1.2989(17) . ? N11 N21 1.3522(17) . ? N21 C31 1.3503(18) . ? N21 H21 0.8800 . ? C31 N31 1.3204(18) . ? C31 N41 1.3411(17) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N41 C51 1.3293(18) . ? C51 N51 1.3230(17) . ? C51 C61 1.461(2) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C61 C611 1.483(2) . ? C611 C661 1.393(2) . ? C611 C621 1.399(2) . ? C621 C631 1.387(2) . ? C631 C641 1.385(2) . ? C641 C651 1.385(2) . ? C641 H641 0.9500 . ? C651 C661 1.386(2) . ? C651 H651 0.9500 . ? C661 H661 0.9500 . ? O12 C12 1.2530(17) . ? O22 C12 1.2653(17) . ? C12 C22 1.5207(18) . ? C22 C22 1.532(3) 3_666 ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? O13 C13 1.197(2) . ? C13 C23 1.482(4) . ? C13 C33 1.484(4) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C61 N11 N21 117.21(12) . . ? C31 N21 N11 122.69(11) . . ? C31 N21 H21 118.7 . . ? N11 N21 H21 118.7 . . ? N31 C31 N41 119.50(13) . . ? N31 C31 N21 118.79(12) . . ? N41 C31 N21 121.70(13) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C51 N41 C31 117.12(12) . . ? N51 C51 N41 118.57(13) . . ? N51 C51 C61 121.23(13) . . ? N41 C51 C61 120.19(12) . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? N11 C61 C51 120.41(13) . . ? N11 C61 C611 117.80(13) . . ? C51 C61 C611 121.77(12) . . ? C661 C611 C621 119.02(13) . . ? C661 C611 C61 120.08(13) . . ? C621 C611 C61 120.88(13) . . ? C631 C621 C611 120.16(14) . . ? C631 C621 Cl11 120.50(12) . . ? C611 C621 Cl11 119.34(12) . . ? C641 C631 C621 120.44(14) . . ? C641 C631 Cl21 118.90(13) . . ? C621 C631 Cl21 120.65(13) . . ? C651 C641 C631 119.62(15) . . ? C651 C641 H641 120.2 . . ? C631 C641 H641 120.2 . . ? C641 C651 C661 120.42(15) . . ? C641 C651 H651 119.8 . . ? C661 C651 H651 119.8 . . ? C651 C661 C611 120.34(14) . . ? C651 C661 H661 119.8 . . ? C611 C661 H661 119.8 . . ? O12 C12 O22 124.13(12) . . ? O12 C12 C22 118.17(12) . . ? O22 C12 C22 117.69(12) . . ? C12 C22 C22 110.38(14) . 3_666 ? C12 C22 H22A 109.6 . . ? C22 C22 H22A 109.6 3_666 . ? C12 C22 H22B 109.6 . . ? C22 C22 H22B 109.6 3_666 . ? H22A C22 H22B 108.1 . . ? O13 C13 C23 120.3(2) . . ? O13 C13 C33 121.6(2) . . ? C23 C13 C33 118.1(2) . . ? C13 C23 H23A 109.5 . . ? C13 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C13 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C13 C33 H33A 109.5 . . ? C13 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C13 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 C61 N11 N21 C31 4.6(2) . . . . ? N11 N21 C31 N31 171.86(14) . . . . ? N11 N21 C31 N41 -8.7(2) . . . . ? N31 C31 N41 C51 -176.30(14) . . . . ? N21 C31 N41 C51 4.2(2) . . . . ? C31 N41 C51 N51 -175.92(14) . . . . ? C31 N41 C51 C61 3.3(2) . . . . ? N21 N11 C61 C51 3.0(2) . . . . ? N21 N11 C61 C611 -178.49(12) . . . . ? N51 C51 C61 N11 172.00(14) . . . . ? N41 C51 C61 N11 -7.2(2) . . . . ? N51 C51 C61 C611 -6.4(2) . . . . ? N41 C51 C61 C611 174.44(13) . . . . ? N11 C61 C611 C661 -71.39(19) . . . . ? C51 C61 C611 C661 107.05(16) . . . . ? N11 C61 C611 C621 110.21(16) . . . . ? C51 C61 C611 C621 -71.35(19) . . . . ? C661 C611 C621 C631 0.2(2) . . . . ? C61 C611 C621 C631 178.63(13) . . . . ? C661 C611 C621 Cl11 179.74(11) . . . . ? C61 C611 C621 Cl11 -1.84(19) . . . . ? C611 C621 C631 C641 -0.4(2) . . . . ? Cl11 C621 C631 C641 -179.91(13) . . . . ? C611 C621 C631 Cl21 180.00(11) . . . . ? Cl11 C621 C631 Cl21 0.48(19) . . . . ? C621 C631 C641 C651 0.0(3) . . . . ? Cl21 C631 C641 C651 179.59(14) . . . . ? C631 C641 C651 C661 0.6(3) . . . . ? C641 C651 C661 C611 -0.8(3) . . . . ? C621 C611 C661 C651 0.4(2) . . . . ? C61 C611 C661 C651 -178.06(15) . . . . ? O12 C12 C22 C22 102.06(18) . . . 3_666 ? O22 C12 C22 C22 -76.78(19) . . . 3_666 ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 33.16 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.353 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.056 # Attachment 'LM+4.(DMSO).cif' data_LM+4.(DMSO) _database_code_depnum_ccdc_archive 'CCDC 856207' #TrackingRef 'LM+4.(DMSO).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - D-tartrate - dimethyl sulfoxide (2:1:2) ; _chemical_absolute_configuration syn _chemical_name_common ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - D- tartrate -dimethyl sulfoxide (2:1:2) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C4 H4 O6, 2(C2 H6 O S)' _chemical_formula_sum 'C26 H32 Cl4 N10 O8 S2' _chemical_formula_weight 818.54 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.09580(10) _cell_length_b 11.0374(2) _cell_length_c 15.6848(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.9470(10) _cell_angle_gamma 90.00 _cell_volume 1837.48(4) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 13114 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 32.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 0.495 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.918 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 21241 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 32.01 _reflns_number_total 11316 _reflns_number_gt 10453 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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. The two DMSO solvent molecules show a disorder of the S atom into two positions with final refined ocupancies of 0.79-0.21 and 0.95-0.05. The disordered C and O atoms were modeled as anisotropic by using and EADP and EXYZ restraints. For one of the DMSO molecules the S atom was refined as anisotropic by using the ISOR and SIMU restraint instructiuons in SHELX. ; _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^)+(0.0373P)^2^+0.6178P] 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 -0.03(3) _refine_ls_number_reflns 11316 _refine_ls_number_parameters 478 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.003 _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 H22 H 0.593(2) 0.840(2) 0.5458(16) 0.032(6) Uiso 1 1 d . . . H21 H 0.408(2) 0.818(3) 0.9606(18) 0.050(8) Uiso 1 1 d . . . Cl11 Cl 0.03817(5) 0.71238(5) 0.67095(3) 0.03766(11) Uani 1 1 d . . . Cl21 Cl -0.14343(4) 0.87076(6) 0.51868(4) 0.04237(12) Uani 1 1 d . . . N11 N 0.31911(14) 0.85862(13) 0.83592(9) 0.0238(3) Uani 1 1 d . . . N21 N 0.39715(14) 0.79143(13) 0.90092(8) 0.0238(3) Uani 1 1 d . . . C31 C 0.44402(16) 0.68376(15) 0.88492(9) 0.0219(3) Uani 1 1 d . . . N31 N 0.50424(16) 0.61596(15) 0.95353(9) 0.0305(3) Uani 1 1 d . . . H31A H 0.5372 0.5463 0.9446 0.037 Uiso 1 1 calc R . . H31B H 0.5114 0.6405 1.0082 0.037 Uiso 1 1 calc R . . N41 N 0.43345(14) 0.64600(14) 0.80184(8) 0.0248(3) Uani 1 1 d . . . C51 C 0.36300(16) 0.71370(16) 0.73530(10) 0.0228(3) Uani 1 1 d . . . N51 N 0.35637(16) 0.68403(15) 0.65268(9) 0.0308(3) Uani 1 1 d . . . H51A H 0.3979 0.6206 0.6422 0.037 Uiso 1 1 calc R . . H51B H 0.3104 0.7277 0.6080 0.037 Uiso 1 1 calc R . . C61 C 0.29686(15) 0.81919(15) 0.75464(10) 0.0217(3) Uani 1 1 d . . . C661 C 0.24879(18) 1.00030(18) 0.65653(13) 0.0314(4) Uani 1 1 d . . . H661 H 0.3314 1.0289 0.6854 0.038 Uiso 1 1 calc R . . C621 C 0.08776(15) 0.84947(15) 0.63987(10) 0.0230(3) Uani 1 1 d . . . C631 C 0.00761(16) 0.91877(17) 0.57270(11) 0.0261(3) Uani 1 1 d . . . C641 C 0.04782(18) 1.02820(19) 0.54725(13) 0.0338(4) Uani 1 1 d . . . H641 H -0.0074 1.0756 0.5018 0.041 Uiso 1 1 calc R . . C651 C 0.1697(2) 1.0681(2) 0.58879(15) 0.0396(5) Uani 1 1 d . . . H651 H 0.1987 1.1420 0.5706 0.048 Uiso 1 1 calc R . . C611 C 0.20892(15) 0.89113(15) 0.68272(10) 0.0215(3) Uani 1 1 d . . . Cl12 Cl 0.96620(5) 0.91500(5) 0.83364(4) 0.04069(12) Uani 1 1 d . . . Cl22 Cl 1.14359(5) 0.74074(8) 0.97501(4) 0.05635(17) Uani 1 1 d . . . N12 N 0.67819(13) 0.78522(13) 0.66009(8) 0.0231(3) Uani 1 1 d . . . N22 N 0.60202(14) 0.85892(14) 0.59856(8) 0.0240(3) Uani 1 1 d . . . C32 C 0.56077(15) 0.96695(15) 0.61960(10) 0.0223(3) Uani 1 1 d . . . N32 N 0.49893(15) 1.03927(14) 0.55411(9) 0.0285(3) Uani 1 1 d . . . H32A H 0.4703 1.1095 0.5664 0.034 Uiso 1 1 calc R . . H32B H 0.4864 1.0171 0.4983 0.034 Uiso 1 1 calc R . . N42 N 0.57983(14) 1.00052(14) 0.70444(9) 0.0251(3) Uani 1 1 d . . . C52 C 0.64940(16) 0.92739(15) 0.76823(10) 0.0225(3) Uani 1 1 d . . . N52 N 0.66509(16) 0.95596(16) 0.85201(9) 0.0313(3) Uani 1 1 d . . . H52A H 0.6303 1.0221 0.8655 0.038 Uiso 1 1 calc R . . H52B H 0.7105 0.9090 0.8947 0.038 Uiso 1 1 calc R . . C62 C 0.70482(15) 0.81767(15) 0.74302(10) 0.0215(3) Uani 1 1 d . . . C612 C 0.79112(15) 0.73807(15) 0.81021(10) 0.0219(3) Uani 1 1 d . . . C622 C 0.91343(15) 0.77479(17) 0.85566(10) 0.0245(3) Uani 1 1 d . . . C632 C 0.99182(16) 0.6970(2) 0.91731(11) 0.0302(4) Uani 1 1 d . . . C642 C 0.95037(18) 0.5844(2) 0.93404(13) 0.0348(4) Uani 1 1 d . . . H642 H 1.0050 0.5318 0.9759 0.042 Uiso 1 1 calc R . . C652 C 0.8289(2) 0.5482(2) 0.88974(15) 0.0405(5) Uani 1 1 d . . . H652 H 0.7996 0.4710 0.9016 0.049 Uiso 1 1 calc R . . C662 C 0.74973(18) 0.62495(18) 0.82771(13) 0.0325(4) Uani 1 1 d . . . H662 H 0.6666 0.5995 0.7971 0.039 Uiso 1 1 calc R . . C13 C 0.43182(15) 0.78909(15) 1.12305(9) 0.0211(3) Uani 1 1 d . . . C23 C 0.42564(15) 0.82949(14) 1.21549(9) 0.0203(3) Uani 1 1 d . . . H23 H 0.3787 0.9080 1.2079 0.024 Uiso 1 1 calc R . . C33 C 0.55913(15) 0.85286(15) 1.27670(9) 0.0227(3) Uani 1 1 d . . . H33 H 0.5941 0.9266 1.2554 0.027 Uiso 1 1 calc R . . C43 C 0.54944(15) 0.87646(16) 1.37112(9) 0.0226(3) Uani 1 1 d . . . O13 O 0.58553(12) 0.79331(12) 1.42778(7) 0.0273(2) Uani 1 1 d . . . O23 O 0.50624(13) 0.97734(12) 1.38418(8) 0.0299(3) Uani 1 1 d . . . O33 O 0.42931(14) 0.87198(12) 1.06733(7) 0.0317(3) Uani 1 1 d . . . O43 O 0.43870(14) 0.67870(12) 1.10855(8) 0.0316(3) Uani 1 1 d . . . O53 O 0.35936(11) 0.74543(12) 1.25249(7) 0.0268(2) Uani 1 1 d . . . H53 H 0.3954 0.6777 1.2575 0.040 Uiso 1 1 calc R . . O63 O 0.63987(12) 0.75352(14) 1.27706(8) 0.0332(3) Uani 1 1 d . . . H63 H 0.5996 0.6990 1.2431 0.050 Uiso 1 1 calc R . . S114 S 0.24188(5) 0.77020(6) 0.41252(3) 0.03762(12) Uani 0.95 1 d PU A 1 O14 O 0.19233(16) 0.7603(2) 0.49228(9) 0.0504(5) Uani 0.95 1 d P A 1 C14 C 0.1395(3) 0.6758(3) 0.33039(16) 0.0575(7) Uani 0.95 1 d P A 1 H14A H 0.1558 0.5907 0.3476 0.086 Uiso 0.95 1 calc PR A 1 H14B H 0.1547 0.6894 0.2726 0.086 Uiso 0.95 1 calc PR A 1 H14C H 0.0517 0.6955 0.3258 0.086 Uiso 0.95 1 calc PR A 1 C24 C 0.1899(3) 0.9132(3) 0.36283(19) 0.0582(7) Uani 0.95 1 d P A 1 H24A H 0.2380 0.9779 0.4004 0.087 Uiso 0.95 1 calc PR A 1 H24B H 0.1001 0.9233 0.3570 0.087 Uiso 0.95 1 calc PR A 1 H24C H 0.2029 0.9169 0.3037 0.087 Uiso 0.95 1 calc PR A 1 S124 S 0.1207(11) 0.7971(12) 0.4017(7) 0.0418(11) Uani 0.05 1 d PU B 2 O14B O 0.19233(16) 0.7603(2) 0.49228(9) 0.0504(5) Uani 0.05 1 d P B 2 C14B C 0.1395(3) 0.6758(3) 0.33039(16) 0.0575(7) Uani 0.05 1 d P B 2 H14D H 0.0997 0.6023 0.3446 0.086 Uiso 0.05 1 calc PR B 2 H14E H 0.2294 0.6607 0.3396 0.086 Uiso 0.05 1 calc PR B 2 H14F H 0.0997 0.6982 0.2680 0.086 Uiso 0.05 1 calc PR B 2 C24B C 0.1899(3) 0.9132(3) 0.36283(19) 0.0582(7) Uani 0.05 1 d P B 2 H24D H 0.1827 0.9875 0.3951 0.087 Uiso 0.05 1 calc PR B 2 H24E H 0.1479 0.9245 0.2991 0.087 Uiso 0.05 1 calc PR B 2 H24F H 0.2791 0.8945 0.3718 0.087 Uiso 0.05 1 calc PR B 2 S115 S 0.75082(6) 0.82172(8) 1.08284(5) 0.04178(15) Uani 0.79 1 d P C 1 C15 C 0.8083(4) 0.6813(3) 1.1234(2) 0.0691(9) Uani 0.79 1 d P C 1 H15A H 0.7738 0.6195 1.0779 0.104 Uiso 0.79 1 calc PR C 1 H15B H 0.7833 0.6631 1.1770 0.104 Uiso 0.79 1 calc PR C 1 H15C H 0.9004 0.6815 1.1382 0.104 Uiso 0.79 1 calc PR C 1 C25 C 0.8262(3) 0.9139(3) 1.17492(18) 0.0669(8) Uani 0.79 1 d P C 1 H25A H 0.8020 0.9986 1.1609 0.100 Uiso 0.79 1 calc PR C 1 H25B H 0.9178 0.9058 1.1879 0.100 Uiso 0.79 1 calc PR C 1 H25C H 0.8007 0.8884 1.2270 0.100 Uiso 0.79 1 calc PR C 1 O15 O 0.81383(19) 0.85644(19) 1.01130(10) 0.0534(5) Uani 0.79 1 d P C 1 S125 S 0.8719(2) 0.8249(3) 1.10756(15) 0.0385(5) Uani 0.21 1 d P D 2 C15B C 0.8083(4) 0.6813(3) 1.1234(2) 0.0691(9) Uani 0.21 1 d P D 2 H15D H 0.8292 0.6216 1.0837 0.104 Uiso 0.21 1 calc PR D 2 H15E H 0.7165 0.6877 1.1097 0.104 Uiso 0.21 1 calc PR D 2 H15F H 0.8441 0.6556 1.1854 0.104 Uiso 0.21 1 calc PR D 2 C25B C 0.8262(3) 0.9139(3) 1.17492(18) 0.0669(8) Uani 0.21 1 d P D 2 H25D H 0.8585 0.9958 1.1715 0.100 Uiso 0.21 1 calc PR D 2 H25E H 0.8587 0.8835 1.2361 0.100 Uiso 0.21 1 calc PR D 2 H25F H 0.7340 0.9159 1.1578 0.100 Uiso 0.21 1 calc PR D 2 O15B O 0.81383(19) 0.85644(19) 1.01130(10) 0.0534(5) Uani 0.21 1 d P D 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl11 0.0446(3) 0.0308(2) 0.0382(2) 0.00089(17) 0.01313(19) -0.0138(2) Cl21 0.0262(2) 0.0491(3) 0.0442(2) -0.0087(2) -0.00177(17) -0.0053(2) N11 0.0315(7) 0.0198(6) 0.0198(5) 0.0002(5) 0.0068(5) 0.0018(5) N21 0.0347(7) 0.0192(6) 0.0167(5) -0.0019(4) 0.0064(5) 0.0046(5) C31 0.0286(7) 0.0199(7) 0.0170(6) -0.0015(5) 0.0065(5) 0.0025(6) N31 0.0473(9) 0.0259(7) 0.0169(5) 0.0002(5) 0.0072(5) 0.0113(7) N41 0.0355(7) 0.0214(7) 0.0168(5) -0.0012(4) 0.0064(5) 0.0062(6) C51 0.0306(7) 0.0205(7) 0.0174(6) -0.0013(5) 0.0070(5) 0.0016(6) N51 0.0457(8) 0.0297(8) 0.0165(5) 0.0003(5) 0.0081(5) 0.0139(7) C61 0.0274(7) 0.0181(7) 0.0197(6) 0.0001(5) 0.0073(5) 0.0013(6) C661 0.0282(8) 0.0237(8) 0.0363(8) 0.0065(7) -0.0002(6) -0.0029(7) C621 0.0269(7) 0.0210(7) 0.0219(6) -0.0032(5) 0.0084(5) -0.0020(6) C631 0.0240(7) 0.0272(8) 0.0249(7) -0.0061(6) 0.0039(5) -0.0001(6) C641 0.0331(9) 0.0284(9) 0.0325(8) 0.0036(7) -0.0021(7) 0.0032(7) C651 0.0371(10) 0.0263(10) 0.0456(11) 0.0127(8) -0.0035(8) -0.0045(8) C611 0.0248(7) 0.0186(7) 0.0202(6) -0.0010(5) 0.0052(5) 0.0013(5) Cl12 0.0424(3) 0.0334(3) 0.0452(2) 0.00094(19) 0.0110(2) -0.0161(2) Cl22 0.0270(2) 0.0758(5) 0.0540(3) 0.0029(3) -0.0076(2) -0.0112(3) N12 0.0294(7) 0.0187(6) 0.0200(5) -0.0009(4) 0.0053(5) 0.0016(5) N22 0.0342(7) 0.0212(6) 0.0151(5) -0.0010(4) 0.0047(5) 0.0024(6) C32 0.0283(7) 0.0207(7) 0.0187(6) 0.0005(5) 0.0081(5) 0.0010(6) N32 0.0412(8) 0.0246(7) 0.0182(6) 0.0020(5) 0.0060(5) 0.0093(6) N42 0.0336(7) 0.0234(7) 0.0180(5) 0.0000(5) 0.0069(5) 0.0058(6) C52 0.0291(7) 0.0190(7) 0.0189(6) -0.0016(5) 0.0062(5) 0.0017(6) N52 0.0454(9) 0.0295(8) 0.0174(6) -0.0017(5) 0.0065(5) 0.0110(7) C62 0.0252(7) 0.0184(7) 0.0196(6) -0.0008(5) 0.0042(5) 0.0000(6) C612 0.0241(7) 0.0193(7) 0.0210(6) -0.0009(5) 0.0045(5) -0.0007(6) C622 0.0261(7) 0.0254(8) 0.0224(6) -0.0029(6) 0.0078(5) -0.0055(6) C632 0.0208(7) 0.0399(11) 0.0265(7) -0.0016(7) 0.0014(5) -0.0028(7) C642 0.0300(9) 0.0337(10) 0.0348(9) 0.0077(7) 0.0001(7) 0.0061(8) C652 0.0347(10) 0.0260(10) 0.0507(12) 0.0122(8) -0.0032(8) -0.0038(8) C662 0.0266(8) 0.0219(8) 0.0407(9) 0.0053(7) -0.0033(7) -0.0032(7) C13 0.0258(7) 0.0212(7) 0.0154(5) -0.0006(5) 0.0047(5) -0.0021(6) C23 0.0269(7) 0.0185(7) 0.0155(5) 0.0001(5) 0.0062(5) 0.0012(5) C33 0.0294(7) 0.0216(7) 0.0172(6) -0.0019(5) 0.0071(5) -0.0009(6) C43 0.0275(7) 0.0233(7) 0.0160(5) -0.0033(5) 0.0050(5) -0.0073(6) O13 0.0357(6) 0.0255(6) 0.0166(4) -0.0001(4) 0.0014(4) -0.0019(5) O23 0.0496(7) 0.0218(6) 0.0203(5) -0.0017(4) 0.0132(5) -0.0020(5) O33 0.0581(8) 0.0198(6) 0.0167(4) -0.0006(4) 0.0102(5) -0.0045(6) O43 0.0567(8) 0.0195(6) 0.0234(5) -0.0002(4) 0.0192(5) 0.0009(6) O53 0.0307(5) 0.0298(6) 0.0226(5) -0.0008(4) 0.0119(4) -0.0032(5) O63 0.0305(6) 0.0390(8) 0.0266(5) -0.0037(5) 0.0030(4) 0.0106(6) S114 0.0326(2) 0.0563(4) 0.02337(18) 0.0023(2) 0.00724(16) 0.0076(2) O14 0.0570(9) 0.0730(13) 0.0226(6) 0.0079(7) 0.0138(6) 0.0211(9) C14 0.0614(15) 0.077(2) 0.0423(11) -0.0135(12) 0.0271(11) -0.0252(14) C24 0.0594(15) 0.0606(18) 0.0567(14) 0.0148(13) 0.0204(12) 0.0046(14) S124 0.0396(15) 0.0510(16) 0.0352(15) 0.0014(14) 0.0116(13) 0.0045(14) O14B 0.0570(9) 0.0730(13) 0.0226(6) 0.0079(7) 0.0138(6) 0.0211(9) C14B 0.0614(15) 0.077(2) 0.0423(11) -0.0135(12) 0.0271(11) -0.0252(14) C24B 0.0594(15) 0.0606(18) 0.0567(14) 0.0148(13) 0.0204(12) 0.0046(14) S115 0.0308(3) 0.0526(4) 0.0404(3) -0.0003(3) 0.0079(2) 0.0057(3) C15 0.098(2) 0.0581(19) 0.0548(15) 0.0115(13) 0.0286(15) -0.0022(17) C25 0.086(2) 0.077(2) 0.0477(13) -0.0174(14) 0.0358(14) -0.0219(18) O15 0.0723(11) 0.0597(12) 0.0250(6) 0.0077(7) 0.0090(7) 0.0118(10) S125 0.0344(11) 0.0558(15) 0.0264(9) 0.0056(9) 0.0104(8) 0.0064(10) C15B 0.098(2) 0.0581(19) 0.0548(15) 0.0115(13) 0.0286(15) -0.0022(17) C25B 0.086(2) 0.077(2) 0.0477(13) -0.0174(14) 0.0358(14) -0.0219(18) O15B 0.0723(11) 0.0597(12) 0.0250(6) 0.0077(7) 0.0090(7) 0.0118(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 Cl11 C621 1.7281(18) . ? Cl21 C631 1.7261(17) . ? N11 C61 1.3008(19) . ? N11 N21 1.3508(18) . ? N21 C31 1.350(2) . ? N21 H21 0.95(3) . ? C31 N31 1.321(2) . ? C31 N41 1.3401(18) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N41 C51 1.335(2) . ? C51 N51 1.3177(19) . ? C51 C61 1.455(2) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C61 C611 1.488(2) . ? C661 C651 1.384(3) . ? C661 C611 1.387(2) . ? C661 H661 0.9500 . ? C621 C631 1.393(2) . ? C621 C611 1.394(2) . ? C631 C641 1.386(3) . ? C641 C651 1.391(3) . ? C641 H641 0.9500 . ? C651 H651 0.9500 . ? Cl12 C622 1.7248(18) . ? Cl22 C632 1.7321(18) . ? N12 C62 1.2976(19) . ? N12 N22 1.3535(19) . ? N22 C32 1.352(2) . ? N22 H22 0.83(2) . ? C32 N32 1.324(2) . ? C32 N42 1.3375(19) . ? N32 H32A 0.8800 . ? N32 H32B 0.8800 . ? N42 C52 1.341(2) . ? C52 N52 1.3127(19) . ? C52 C62 1.464(2) . ? N52 H52A 0.8800 . ? N52 H52B 0.8800 . ? C62 C612 1.487(2) . ? C612 C662 1.385(3) . ? C612 C622 1.396(2) . ? C622 C632 1.393(3) . ? C632 C642 1.376(3) . ? C642 C652 1.383(3) . ? C642 H642 0.9500 . ? C652 C662 1.392(3) . ? C652 H652 0.9500 . ? C662 H662 0.9500 . ? C13 O43 1.246(2) . ? C13 O33 1.2600(19) . ? C13 C23 1.5374(19) . ? C23 O53 1.4097(19) . ? C23 C33 1.534(2) . ? C23 H23 1.0000 . ? C33 O63 1.415(2) . ? C33 C43 1.538(2) . ? C33 H33 1.0000 . ? C43 O23 1.252(2) . ? C43 O13 1.259(2) . ? O53 H53 0.8400 . ? O63 H63 0.8400 . ? S114 O14 1.5100(15) . ? S114 C24 1.780(3) . ? S114 C14 1.784(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? S115 O15 1.5337(19) . ? S115 C15 1.725(4) . ? S115 C25 1.765(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C61 N11 N21 116.93(14) . . ? C31 N21 N11 122.68(13) . . ? C31 N21 H21 120.3(18) . . ? N11 N21 H21 116.4(17) . . ? N31 C31 N41 119.74(15) . . ? N31 C31 N21 118.55(13) . . ? N41 C31 N21 121.69(14) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C51 N41 C31 116.83(14) . . ? N51 C51 N41 118.80(15) . . ? N51 C51 C61 121.13(15) . . ? N41 C51 C61 120.06(13) . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? N11 C61 C51 120.59(14) . . ? N11 C61 C611 117.37(14) . . ? C51 C61 C611 121.90(13) . . ? C651 C661 C611 120.78(17) . . ? C651 C661 H661 119.6 . . ? C611 C661 H661 119.6 . . ? C631 C621 C611 119.80(16) . . ? C631 C621 Cl11 120.57(13) . . ? C611 C621 Cl11 119.62(13) . . ? C641 C631 C621 120.55(16) . . ? C641 C631 Cl21 118.30(14) . . ? C621 C631 Cl21 121.15(14) . . ? C631 C641 C651 119.46(17) . . ? C631 C641 H641 120.3 . . ? C651 C641 H641 120.3 . . ? C661 C651 C641 120.05(19) . . ? C661 C651 H651 120.0 . . ? C641 C651 H651 120.0 . . ? C661 C611 C621 119.33(15) . . ? C661 C611 C61 119.54(15) . . ? C621 C611 C61 121.11(15) . . ? C62 N12 N22 117.47(14) . . ? C32 N22 N12 122.78(13) . . ? C32 N22 H22 120.9(17) . . ? N12 N22 H22 115.3(17) . . ? N32 C32 N42 120.06(15) . . ? N32 C32 N22 118.57(14) . . ? N42 C32 N22 121.37(14) . . ? C32 N32 H32A 120.0 . . ? C32 N32 H32B 120.0 . . ? H32A N32 H32B 120.0 . . ? C32 N42 C52 117.73(14) . . ? N52 C52 N42 118.81(15) . . ? N52 C52 C62 121.70(15) . . ? N42 C52 C62 119.49(13) . . ? C52 N52 H52A 120.0 . . ? C52 N52 H52B 120.0 . . ? H52A N52 H52B 120.0 . . ? N12 C62 C52 120.55(14) . . ? N12 C62 C612 117.31(14) . . ? C52 C62 C612 122.13(13) . . ? C662 C612 C622 119.31(15) . . ? C662 C612 C62 119.39(15) . . ? C622 C612 C62 121.30(15) . . ? C632 C622 C612 119.52(16) . . ? C632 C622 Cl12 120.85(13) . . ? C612 C622 Cl12 119.63(13) . . ? C642 C632 C622 120.90(16) . . ? C642 C632 Cl22 118.71(15) . . ? C622 C632 Cl22 120.40(15) . . ? C632 C642 C652 119.73(18) . . ? C632 C642 H642 120.1 . . ? C652 C642 H642 120.1 . . ? C642 C652 C662 119.98(19) . . ? C642 C652 H652 120.0 . . ? C662 C652 H652 120.0 . . ? C612 C662 C652 120.57(17) . . ? C612 C662 H662 119.7 . . ? C652 C662 H662 119.7 . . ? O43 C13 O33 125.00(14) . . ? O43 C13 C23 118.54(14) . . ? O33 C13 C23 116.46(14) . . ? O53 C23 C33 112.17(12) . . ? O53 C23 C13 111.68(13) . . ? C33 C23 C13 109.79(12) . . ? O53 C23 H23 107.7 . . ? C33 C23 H23 107.7 . . ? C13 C23 H23 107.7 . . ? O63 C33 C23 111.53(13) . . ? O63 C33 C43 110.45(13) . . ? C23 C33 C43 107.78(12) . . ? O63 C33 H33 109.0 . . ? C23 C33 H33 109.0 . . ? C43 C33 H33 109.0 . . ? O23 C43 O13 126.21(14) . . ? O23 C43 C33 116.46(14) . . ? O13 C43 C33 117.33(15) . . ? C23 O53 H53 109.5 . . ? C33 O63 H63 109.5 . . ? O14 S114 C24 106.09(12) . . ? O14 S114 C14 104.31(11) . . ? C24 S114 C14 98.31(16) . . ? S114 C14 H14A 109.5 . . ? S114 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? S114 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? S114 C24 H24A 109.5 . . ? S114 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? S114 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O15 S115 C15 107.20(14) . . ? O15 S115 C25 104.25(13) . . ? C15 S115 C25 100.38(18) . . ? S115 C15 H15A 109.5 . . ? S115 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? S115 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? S115 C25 H25A 109.5 . . ? S115 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S115 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 C61 N11 N21 C31 -4.6(2) . . . . ? N11 N21 C31 N31 -170.17(17) . . . . ? N11 N21 C31 N41 11.4(3) . . . . ? N31 C31 N41 C51 174.78(17) . . . . ? N21 C31 N41 C51 -6.8(2) . . . . ? C31 N41 C51 N51 175.87(17) . . . . ? C31 N41 C51 C61 -3.2(2) . . . . ? N21 N11 C61 C51 -5.5(2) . . . . ? N21 N11 C61 C611 178.75(14) . . . . ? N51 C51 C61 N11 -169.32(17) . . . . ? N41 C51 C61 N11 9.7(3) . . . . ? N51 C51 C61 C611 6.2(3) . . . . ? N41 C51 C61 C611 -174.76(16) . . . . ? C611 C621 C631 C641 0.8(2) . . . . ? Cl11 C621 C631 C641 -179.41(14) . . . . ? C611 C621 C631 Cl21 -179.52(12) . . . . ? Cl11 C621 C631 Cl21 0.2(2) . . . . ? C621 C631 C641 C651 0.6(3) . . . . ? Cl21 C631 C641 C651 -179.04(18) . . . . ? C611 C661 C651 C641 1.3(3) . . . . ? C631 C641 C651 C661 -1.7(3) . . . . ? C651 C661 C611 C621 0.2(3) . . . . ? C651 C661 C611 C61 178.90(19) . . . . ? C631 C621 C611 C661 -1.2(2) . . . . ? Cl11 C621 C611 C661 179.01(14) . . . . ? C631 C621 C611 C61 -179.91(14) . . . . ? Cl11 C621 C611 C61 0.3(2) . . . . ? N11 C61 C611 C661 74.0(2) . . . . ? C51 C61 C611 C661 -101.7(2) . . . . ? N11 C61 C611 C621 -107.30(18) . . . . ? C51 C61 C611 C621 77.0(2) . . . . ? C62 N12 N22 C32 4.6(2) . . . . ? N12 N22 C32 N32 172.18(16) . . . . ? N12 N22 C32 N42 -8.7(3) . . . . ? N32 C32 N42 C52 -176.12(16) . . . . ? N22 C32 N42 C52 4.8(2) . . . . ? C32 N42 C52 N52 -177.26(17) . . . . ? C32 N42 C52 C62 2.2(2) . . . . ? N22 N12 C62 C52 2.6(2) . . . . ? N22 N12 C62 C612 -178.50(14) . . . . ? N52 C52 C62 N12 173.36(18) . . . . ? N42 C52 C62 N12 -6.1(2) . . . . ? N52 C52 C62 C612 -5.5(3) . . . . ? N42 C52 C62 C612 175.02(15) . . . . ? N12 C62 C612 C662 -69.8(2) . . . . ? C52 C62 C612 C662 109.1(2) . . . . ? N12 C62 C612 C622 109.78(18) . . . . ? C52 C62 C612 C622 -71.3(2) . . . . ? C662 C612 C622 C632 0.4(2) . . . . ? C62 C612 C622 C632 -179.23(15) . . . . ? C662 C612 C622 Cl12 179.48(14) . . . . ? C62 C612 C622 Cl12 -0.1(2) . . . . ? C612 C622 C632 C642 0.0(3) . . . . ? Cl12 C622 C632 C642 -179.11(15) . . . . ? C612 C622 C632 Cl22 -179.63(13) . . . . ? Cl12 C622 C632 Cl22 1.3(2) . . . . ? C622 C632 C642 C652 -0.6(3) . . . . ? Cl22 C632 C642 C652 179.05(18) . . . . ? C632 C642 C652 C662 0.8(4) . . . . ? C622 C612 C662 C652 -0.1(3) . . . . ? C62 C612 C662 C652 179.46(19) . . . . ? C642 C652 C662 C612 -0.4(3) . . . . ? O43 C13 C23 O53 -33.9(2) . . . . ? O33 C13 C23 O53 146.06(15) . . . . ? O43 C13 C23 C33 91.21(19) . . . . ? O33 C13 C23 C33 -88.86(18) . . . . ? O53 C23 C33 O63 73.51(15) . . . . ? C13 C23 C33 O63 -51.28(17) . . . . ? O53 C23 C33 C43 -47.88(18) . . . . ? C13 C23 C33 C43 -172.67(13) . . . . ? O63 C33 C43 O23 163.59(15) . . . . ? C23 C33 C43 O23 -74.35(18) . . . . ? O63 C33 C43 O13 -16.3(2) . . . . ? C23 C33 C43 O13 105.74(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N21 H21 O33 0.95(3) 1.73(3) 2.6809(17) 177(3) . N31 H31A O33 0.88 1.98 2.836(2) 164.3 2_647 N31 H31B O43 0.88 2.01 2.8198(18) 152.1 . N51 H51A O23 0.88 2.01 2.894(2) 178.7 2_647 N51 H51B O14 0.88 1.94 2.772(2) 157.5 . N32 H32A O13 0.88 2.13 2.996(2) 167.4 2_657 N32 H32B O23 0.88 1.92 2.7755(18) 164.7 1_554 N52 H52A O43 0.88 1.98 2.858(2) 175.2 2_657 N52 H52B O15 0.88 1.94 2.787(2) 160.4 . O53 H53 N42 0.84 2.04 2.820(2) 154.2 2_647 O63 H63 O43 0.84 2.34 3.0349(19) 139.8 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 32.01 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.357 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.051 # Attachment '- LM+4.(ACON).cif' data_LM+4.(ACON) _database_code_depnum_ccdc_archive 'CCDC 856208' #TrackingRef '- LM+4.(ACON).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - D-tartrate - acetone (2:1:2) ; _chemical_absolute_configuration syn _chemical_name_common ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - D- tartrate -acetone (2:1:2) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C4 H4 O6, 2(C3 H6 O)' _chemical_formula_sum 'C28 H32 Cl4 N10 O8' _chemical_formula_weight 778.44 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.7524(2) _cell_length_b 11.3284(2) _cell_length_c 15.5321(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.0240(10) _cell_angle_gamma 90.00 _cell_volume 1827.25(6) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 13469 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 0.384 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.905 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 21966 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 30.02 _reflns_number_total 9677 _reflns_number_gt 7976 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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. One of the acetone solvent molecule shows a disordered into two positions with final refined occupancies of 0.58 and 0.42. The disorder of the acetone molecule was modelled using a SAME instruction restraint in SHELX. The disordered atoms were modelled as anisotropic by using and EADP restraint. The hydrogen atoms of the hydroxyl groups were placed as riding on their bonded atoms with a refined torsion angle from electron density. ; _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^)+(0.0590P)^2^+0.4616P] 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 -0.02(5) _refine_ls_number_reflns 9677 _refine_ls_number_parameters 468 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1268 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 Cl12 Cl 0.54404(7) 0.12941(10) 0.66761(5) 0.04730(18) Uani 1 1 d . . . C641 C 0.4421(3) 0.0108(3) 0.93539(18) 0.0452(7) Uani 1 1 d . . . H641 H 0.4934 -0.0409 0.9784 0.054 Uiso 1 1 calc R . . Cl11 Cl 0.47471(7) 0.33317(11) 0.83887(5) 0.05005(19) Uani 1 1 d . . . C651 C 0.3221(3) -0.0241(3) 0.8862(2) 0.0470(7) Uani 1 1 d . . . H651 H 0.2901 -0.0999 0.8954 0.056 Uiso 1 1 calc R . . Cl21 Cl 0.63851(8) 0.16237(13) 0.98571(6) 0.0704(3) Uani 1 1 d . . . C631 C 0.4876(2) 0.1211(3) 0.92183(16) 0.0401(6) Uani 1 1 d . . . Cl22 Cl 0.37102(7) 0.27893(11) 0.50925(5) 0.0532(2) Uani 1 1 d . . . C661 C 0.2474(3) 0.0519(3) 0.82277(18) 0.0387(6) Uani 1 1 d . . . H661 H 0.1651 0.0270 0.7884 0.046 Uiso 1 1 calc R . . C51 C 0.1578(2) 0.3534(2) 0.76959(15) 0.0299(5) Uani 1 1 d . . . C31 C 0.0735(2) 0.3955(2) 0.62161(14) 0.0276(5) Uani 1 1 d . . . N51 N 0.1695(2) 0.3802(2) 0.85386(13) 0.0384(5) Uani 1 1 d . . . H51A H 0.1363 0.4463 0.8678 0.046 Uiso 1 1 calc R . . H51B H 0.2106 0.3321 0.8962 0.046 Uiso 1 1 calc R . . N31 N 0.0182(2) 0.4683(2) 0.55738(13) 0.0346(5) Uani 1 1 d . . . H31B H -0.0050 0.5392 0.5703 0.041 Uiso 1 1 calc R . . H31A H 0.0044 0.4462 0.5014 0.041 Uiso 1 1 calc R . . C611 C 0.2917(2) 0.1624(2) 0.80950(14) 0.0287(5) Uani 1 1 d . . . C61 C 0.2092(2) 0.2432(2) 0.74325(14) 0.0273(5) Uani 1 1 d . . . C621 C 0.4143(2) 0.1974(2) 0.85861(16) 0.0326(5) Uani 1 1 d . . . N21 N 0.1084(2) 0.2874(2) 0.59995(12) 0.0300(4) Uani 1 1 d . . . H21 H 0.0830 0.2649 0.5439 0.036 Uiso 1 1 calc R . . N41 N 0.0950(2) 0.4285(2) 0.70734(12) 0.0308(4) Uani 1 1 d . . . N11 N 0.1805(2) 0.21173(19) 0.66020(12) 0.0297(4) Uani 1 1 d . . . C652 C 0.6828(3) 0.4797(3) 0.5914(2) 0.0470(7) Uani 1 1 d . . . H652 H 0.7122 0.5535 0.5755 0.056 Uiso 1 1 calc R . . C642 C 0.5636(3) 0.4362(3) 0.54506(18) 0.0420(6) Uani 1 1 d . . . H642 H 0.5113 0.4804 0.4972 0.050 Uiso 1 1 calc R . . C32 C 0.9385(2) 0.0951(2) 0.88467(15) 0.0291(5) Uani 1 1 d . . . N32 N 0.9915(2) 0.0252(2) 0.95255(13) 0.0380(5) Uani 1 1 d . . . H32B H 1.0188 -0.0455 0.9427 0.046 Uiso 1 1 calc R . . H32A H 0.9993 0.0494 1.0075 0.046 Uiso 1 1 calc R . . C632 C 0.5206(2) 0.3289(3) 0.56822(16) 0.0340(5) Uani 1 1 d . . . C52 C 0.8661(2) 0.1282(2) 0.73562(14) 0.0285(5) Uani 1 1 d . . . C662 C 0.7584(3) 0.4150(3) 0.66083(18) 0.0382(6) Uani 1 1 d . . . H662 H 0.8393 0.4457 0.6931 0.046 Uiso 1 1 calc R . . C62 C 0.8036(2) 0.2349(2) 0.75590(15) 0.0286(5) Uani 1 1 d . . . C612 C 0.7182(2) 0.3061(2) 0.68419(15) 0.0288(5) Uani 1 1 d . . . N52 N 0.8648(2) 0.1007(2) 0.65308(13) 0.0365(5) Uani 1 1 d . . . H52A H 0.9038 0.0363 0.6421 0.044 Uiso 1 1 calc R . . H52B H 0.8250 0.1467 0.6088 0.044 Uiso 1 1 calc R . . N22 N 0.9003(2) 0.20394(19) 0.90149(12) 0.0311(4) Uani 1 1 d . . . H22 H 0.9247 0.2312 0.9564 0.037 Uiso 1 1 calc R . . C622 C 0.5978(2) 0.2626(2) 0.63737(15) 0.0301(5) Uani 1 1 d . . . N42 N 0.9272(2) 0.0569(2) 0.80125(13) 0.0304(4) Uani 1 1 d . . . N12 N 0.8261(2) 0.2730(2) 0.83765(12) 0.0307(4) Uani 1 1 d . . . C23 C 1.0735(2) -0.2498(2) 0.78230(14) 0.0288(5) Uani 1 1 d . . . H32 H 1.1177 -0.1714 0.7903 0.035 Uiso 1 1 calc R . . C33 C 0.9380(2) -0.2319(2) 0.72201(14) 0.0290(5) Uani 1 1 d . . . H33 H 0.8975 -0.1627 0.7442 0.035 Uiso 1 1 calc R . . O63 O 0.86109(18) -0.3329(2) 0.72246(12) 0.0412(4) Uani 1 1 d . . . H63 H 0.8392 -0.3621 0.6710 0.062 Uiso 1 1 calc R . . O53 O 1.14718(17) -0.32736(19) 0.74436(11) 0.0351(4) Uani 1 1 d . . . H53 H 1.1142 -0.3950 0.7398 0.053 Uiso 1 1 calc R . . O23 O 1.0663(2) -0.39997(18) 0.88900(11) 0.0411(4) Uani 1 1 d . . . O43 O 0.98802(19) -0.10466(17) 0.61407(11) 0.0340(4) Uani 1 1 d . . . O13 O 1.0553(2) -0.21445(18) 0.93003(11) 0.0461(5) Uani 1 1 d . . . C13 C 1.0644(2) -0.2922(2) 0.87460(14) 0.0292(5) Uani 1 1 d . . . C43 C 0.9490(2) -0.2053(2) 0.62741(14) 0.0293(5) Uani 1 1 d . . . O33 O 0.91738(18) -0.28596(18) 0.57027(10) 0.0350(4) Uani 1 1 d . . . C24 C 0.6911(4) 0.3479(4) 0.3637(3) 0.0713(11) Uani 1 1 d . . . H24A H 0.7467 0.4117 0.3944 0.107 Uiso 1 1 calc R . . H24B H 0.6007 0.3706 0.3546 0.107 Uiso 1 1 calc R . . H24C H 0.7087 0.3333 0.3057 0.107 Uiso 1 1 calc R . . C14 C 0.7168(4) 0.2404(4) 0.4177(3) 0.0655(11) Uani 1 1 d . . . O14 O 0.7948(3) 0.2429(3) 0.49167(17) 0.0830(9) Uani 1 1 d . . . C34 C 0.6501(5) 0.1359(6) 0.3818(4) 0.1059(18) Uani 1 1 d . . . H34C H 0.6778 0.0705 0.4236 0.159 Uiso 1 1 calc R . . H34B H 0.6693 0.1170 0.3250 0.159 Uiso 1 1 calc R . . H34A H 0.5573 0.1482 0.3718 0.159 Uiso 1 1 calc R . . C15 C 0.711(2) -0.2792(16) 0.9122(7) 0.062(3) Uani 0.476(13) 1 d PD A 1 O15 O 0.7469(14) -0.2662(13) 0.9915(7) 0.087(3) Uani 0.476(13) 1 d PD A 1 C25 C 0.681(3) -0.174(3) 0.8513(12) 0.094(3) Uani 0.476(13) 1 d PD A 1 H25A H 0.6915 -0.1017 0.8869 0.141 Uiso 0.476(13) 1 calc PR A 1 H25B H 0.5923 -0.1795 0.8145 0.141 Uiso 0.476(13) 1 calc PR A 1 H25C H 0.7403 -0.1725 0.8127 0.141 Uiso 0.476(13) 1 calc PR A 1 C35 C 0.700(8) -0.403(2) 0.8721(19) 0.108(5) Uani 0.476(13) 1 d PD A 1 H35A H 0.7296 -0.4611 0.9197 0.161 Uiso 0.476(13) 1 calc PR A 1 H35B H 0.7532 -0.4081 0.8297 0.161 Uiso 0.476(13) 1 calc PR A 1 H35C H 0.6099 -0.4189 0.8410 0.161 Uiso 0.476(13) 1 calc PR A 1 C152 C 0.6802(19) -0.2516(16) 0.9007(7) 0.062(3) Uani 0.524(13) 1 d PD A 2 O152 O 0.7014(13) -0.2178(12) 0.9764(6) 0.087(3) Uani 0.524(13) 1 d PD A 2 C252 C 0.652(3) -0.165(3) 0.8249(10) 0.094(3) Uani 0.524(13) 1 d PD A 2 H25D H 0.6519 -0.0846 0.8484 0.141 Uiso 0.524(13) 1 calc PR A 2 H25E H 0.5680 -0.1824 0.7845 0.141 Uiso 0.524(13) 1 calc PR A 2 H25F H 0.7189 -0.1711 0.7923 0.141 Uiso 0.524(13) 1 calc PR A 2 C352 C 0.688(8) -0.383(2) 0.8809(17) 0.108(5) Uani 0.524(13) 1 d PD A 2 H35D H 0.6994 -0.4281 0.9361 0.161 Uiso 0.524(13) 1 calc PR A 2 H35E H 0.7617 -0.3971 0.8558 0.161 Uiso 0.524(13) 1 calc PR A 2 H35F H 0.6087 -0.4077 0.8379 0.161 Uiso 0.524(13) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl12 0.0554(4) 0.0402(4) 0.0461(4) -0.0009(3) 0.0127(3) -0.0175(3) C641 0.0429(15) 0.0490(17) 0.0379(14) 0.0092(12) -0.0004(11) 0.0082(13) Cl11 0.0520(4) 0.0445(4) 0.0524(4) -0.0050(3) 0.0114(3) -0.0197(3) C651 0.0464(16) 0.0340(15) 0.0529(17) 0.0116(12) -0.0010(13) -0.0030(12) Cl21 0.0380(4) 0.0982(8) 0.0605(5) 0.0010(5) -0.0135(3) -0.0122(4) C631 0.0311(12) 0.0530(17) 0.0320(12) -0.0045(11) 0.0010(9) -0.0019(12) Cl22 0.0372(3) 0.0616(5) 0.0518(4) -0.0100(3) -0.0044(3) -0.0060(3) C661 0.0348(13) 0.0314(13) 0.0428(14) 0.0035(10) -0.0028(10) -0.0042(10) C51 0.0376(12) 0.0291(12) 0.0223(10) -0.0023(8) 0.0066(9) -0.0010(10) C31 0.0349(12) 0.0247(11) 0.0231(10) -0.0009(8) 0.0076(8) -0.0008(9) N51 0.0587(14) 0.0340(12) 0.0221(9) -0.0015(8) 0.0097(9) 0.0108(10) N31 0.0544(13) 0.0261(10) 0.0223(9) 0.0007(7) 0.0084(9) 0.0076(9) C611 0.0332(12) 0.0289(12) 0.0225(10) -0.0022(9) 0.0046(8) 0.0006(10) C61 0.0348(12) 0.0228(11) 0.0242(10) -0.0021(8) 0.0074(8) -0.0009(9) C621 0.0338(12) 0.0358(13) 0.0286(11) -0.0061(9) 0.0089(9) -0.0058(10) N21 0.0430(11) 0.0251(10) 0.0197(8) -0.0021(7) 0.0043(7) 0.0018(8) N41 0.0430(11) 0.0261(10) 0.0236(9) -0.0018(7) 0.0091(8) 0.0021(9) N11 0.0363(11) 0.0255(10) 0.0256(9) 0.0001(7) 0.0050(7) 0.0002(8) C652 0.0504(17) 0.0303(14) 0.0516(16) 0.0103(12) -0.0024(13) -0.0010(12) C642 0.0420(15) 0.0383(15) 0.0402(14) 0.0038(11) 0.0007(11) 0.0095(12) C32 0.0404(13) 0.0236(11) 0.0242(10) -0.0019(8) 0.0099(9) -0.0002(9) N32 0.0631(14) 0.0274(11) 0.0223(9) -0.0001(8) 0.0088(9) 0.0093(10) C632 0.0298(12) 0.0381(14) 0.0322(12) -0.0072(10) 0.0043(9) 0.0013(11) C52 0.0377(12) 0.0238(11) 0.0245(10) 0.0001(8) 0.0089(8) 0.0019(9) C662 0.0363(13) 0.0275(13) 0.0440(14) 0.0018(10) -0.0015(10) -0.0032(11) C62 0.0358(12) 0.0251(12) 0.0252(10) -0.0006(8) 0.0083(9) -0.0001(9) C612 0.0327(11) 0.0238(12) 0.0286(10) -0.0025(8) 0.0054(9) 0.0026(9) N52 0.0562(13) 0.0302(11) 0.0229(9) 0.0005(8) 0.0097(8) 0.0156(10) N22 0.0468(12) 0.0231(10) 0.0222(9) -0.0023(7) 0.0070(8) 0.0032(8) C622 0.0342(12) 0.0267(12) 0.0303(11) -0.0036(9) 0.0101(9) -0.0019(9) N42 0.0427(12) 0.0251(10) 0.0236(9) -0.0005(7) 0.0090(8) 0.0050(8) N12 0.0416(11) 0.0241(10) 0.0264(9) -0.0019(8) 0.0090(8) -0.0004(9) C23 0.0386(12) 0.0245(11) 0.0221(9) -0.0001(8) 0.0057(8) -0.0032(9) C33 0.0354(11) 0.0284(12) 0.0220(9) 0.0011(9) 0.0052(8) -0.0006(10) O63 0.0457(10) 0.0423(11) 0.0326(9) 0.0020(8) 0.0047(7) -0.0165(9) O53 0.0406(9) 0.0353(10) 0.0318(8) 0.0028(7) 0.0135(7) 0.0038(8) O23 0.0749(13) 0.0242(9) 0.0279(8) 0.0011(7) 0.0197(8) -0.0002(9) O43 0.0548(11) 0.0238(9) 0.0253(8) 0.0016(6) 0.0141(7) 0.0036(8) O13 0.0902(15) 0.0250(9) 0.0224(8) 0.0004(7) 0.0131(8) 0.0097(10) C13 0.0369(12) 0.0277(12) 0.0201(10) 0.0009(8) 0.0020(8) 0.0020(9) C43 0.0356(12) 0.0307(12) 0.0209(9) 0.0007(8) 0.0059(8) 0.0054(10) O33 0.0499(10) 0.0297(9) 0.0208(7) -0.0015(6) 0.0011(7) -0.0019(8) C24 0.069(2) 0.094(3) 0.053(2) 0.021(2) 0.0193(17) 0.030(2) C14 0.062(2) 0.086(3) 0.059(2) 0.0258(19) 0.0352(17) 0.026(2) O14 0.106(2) 0.093(2) 0.0524(14) 0.0257(14) 0.0242(14) 0.0400(18) C34 0.073(3) 0.125(5) 0.132(4) 0.030(4) 0.050(3) -0.009(3) C15 0.043(8) 0.102(8) 0.043(3) -0.017(4) 0.016(3) -0.019(6) O15 0.101(7) 0.119(9) 0.041(3) -0.029(4) 0.016(4) -0.023(5) C25 0.091(11) 0.128(7) 0.067(8) 0.020(8) 0.028(8) 0.032(7) C35 0.166(13) 0.098(7) 0.077(5) -0.033(4) 0.064(7) -0.043(11) C152 0.043(8) 0.102(8) 0.043(3) -0.017(4) 0.016(3) -0.019(6) O152 0.101(7) 0.119(9) 0.041(3) -0.029(4) 0.016(4) -0.023(5) C252 0.091(11) 0.128(7) 0.067(8) 0.020(8) 0.028(8) 0.032(7) C352 0.166(13) 0.098(7) 0.077(5) -0.033(4) 0.064(7) -0.043(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl12 C622 1.724(3) . ? C641 C651 1.376(4) . ? C641 C631 1.377(4) . ? C641 H641 0.9500 . ? Cl11 C621 1.728(3) . ? C651 C661 1.396(4) . ? C651 H651 0.9500 . ? Cl21 C631 1.733(3) . ? C631 C621 1.389(4) . ? Cl22 C632 1.727(2) . ? C661 C611 1.373(4) . ? C661 H661 0.9500 . ? C51 N51 1.318(3) . ? C51 N41 1.333(3) . ? C51 C61 1.465(3) . ? C31 N31 1.312(3) . ? C31 N41 1.344(3) . ? C31 N21 1.349(3) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? N31 H31B 0.8800 . ? N31 H31A 0.8800 . ? C611 C621 1.399(3) . ? C611 C61 1.487(3) . ? C61 N11 1.296(3) . ? N21 N11 1.355(3) . ? N21 H21 0.8800 . ? C652 C662 1.380(4) . ? C652 C642 1.388(4) . ? C652 H652 0.9500 . ? C642 C632 1.381(4) . ? C642 H642 0.9500 . ? C32 N32 1.323(3) . ? C32 N42 1.342(3) . ? C32 N22 1.347(3) . ? N32 H32B 0.8800 . ? N32 H32A 0.8800 . ? C632 C622 1.394(3) . ? C52 N52 1.316(3) . ? C52 N42 1.333(3) . ? C52 C62 1.456(3) . ? C662 C612 1.387(4) . ? C662 H662 0.9500 . ? C62 N12 1.303(3) . ? C62 C612 1.484(3) . ? C612 C622 1.400(3) . ? N52 H52A 0.8800 . ? N52 H52B 0.8800 . ? N22 N12 1.350(3) . ? N22 H22 0.8800 . ? C23 O53 1.410(3) . ? C23 C33 1.528(3) . ? C23 C13 1.539(3) . ? C23 H32 1.0000 . ? C33 O63 1.414(3) . ? C33 C43 1.534(3) . ? C33 H33 1.0000 . ? O63 H63 0.8400 . ? O53 H53 0.8400 . ? O23 C13 1.240(3) . ? O43 C43 1.251(3) . ? O13 C13 1.253(3) . ? C43 O33 1.257(3) . ? C24 C14 1.464(5) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C14 O14 1.235(5) . ? C14 C34 1.421(8) . ? C34 H34C 0.9800 . ? C34 H34B 0.9800 . ? C34 H34A 0.9800 . ? C15 O15 1.200(5) . ? C15 C25 1.503(8) . ? C15 C35 1.525(9) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C152 O152 1.200(5) . ? C152 C252 1.503(8) . ? C152 C352 1.525(9) . ? C252 H25D 0.9800 . ? C252 H25E 0.9800 . ? C252 H25F 0.9800 . ? C352 H35D 0.9800 . ? C352 H35E 0.9800 . ? C352 H35F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C651 C641 C631 119.6(3) . . ? C651 C641 H641 120.2 . . ? C631 C641 H641 120.2 . . ? C641 C651 C661 120.0(3) . . ? C641 C651 H651 120.0 . . ? C661 C651 H651 120.0 . . ? C641 C631 C621 120.9(2) . . ? C641 C631 Cl21 118.3(2) . . ? C621 C631 Cl21 120.8(2) . . ? C611 C661 C651 120.7(2) . . ? C611 C661 H661 119.7 . . ? C651 C661 H661 119.7 . . ? N51 C51 N41 118.2(2) . . ? N51 C51 C61 121.9(2) . . ? N41 C51 C61 119.9(2) . . ? N31 C31 N41 120.4(2) . . ? N31 C31 N21 118.8(2) . . ? N41 C31 N21 120.8(2) . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? C31 N31 H31B 120.0 . . ? C31 N31 H31A 120.0 . . ? H31B N31 H31A 120.0 . . ? C661 C611 C621 119.4(2) . . ? C661 C611 C61 119.8(2) . . ? C621 C611 C61 120.8(2) . . ? N11 C61 C51 120.2(2) . . ? N11 C61 C611 117.7(2) . . ? C51 C61 C611 122.10(19) . . ? C631 C621 C611 119.4(2) . . ? C631 C621 Cl11 120.6(2) . . ? C611 C621 Cl11 120.0(2) . . ? C31 N21 N11 123.26(19) . . ? C31 N21 H21 118.4 . . ? N11 N21 H21 118.4 . . ? C51 N41 C31 117.7(2) . . ? C61 N11 N21 117.3(2) . . ? C662 C652 C642 119.7(3) . . ? C662 C652 H652 120.2 . . ? C642 C652 H652 120.2 . . ? C632 C642 C652 120.2(2) . . ? C632 C642 H642 119.9 . . ? C652 C642 H642 119.9 . . ? N32 C32 N42 119.3(2) . . ? N32 C32 N22 118.9(2) . . ? N42 C32 N22 121.8(2) . . ? C32 N32 H32B 120.0 . . ? C32 N32 H32A 120.0 . . ? H32B N32 H32A 120.0 . . ? C642 C632 C622 120.1(2) . . ? C642 C632 Cl22 118.6(2) . . ? C622 C632 Cl22 121.3(2) . . ? N52 C52 N42 118.6(2) . . ? N52 C52 C62 121.2(2) . . ? N42 C52 C62 120.1(2) . . ? C652 C662 C612 121.1(2) . . ? C652 C662 H662 119.5 . . ? C612 C662 H662 119.5 . . ? N12 C62 C52 120.4(2) . . ? N12 C62 C612 118.3(2) . . ? C52 C62 C612 121.2(2) . . ? C662 C612 C622 119.1(2) . . ? C662 C612 C62 120.4(2) . . ? C622 C612 C62 120.5(2) . . ? C52 N52 H52A 120.0 . . ? C52 N52 H52B 120.0 . . ? H52A N52 H52B 120.0 . . ? C32 N22 N12 122.71(19) . . ? C32 N22 H22 118.6 . . ? N12 N22 H22 118.6 . . ? C632 C622 C612 119.8(2) . . ? C632 C622 Cl12 120.41(19) . . ? C612 C622 Cl12 119.77(18) . . ? C52 N42 C32 116.5(2) . . ? C62 N12 N22 116.7(2) . . ? O53 C23 C33 112.11(18) . . ? O53 C23 C13 111.91(19) . . ? C33 C23 C13 109.37(19) . . ? O53 C23 H32 107.8 . . ? C33 C23 H32 107.8 . . ? C13 C23 H32 107.8 . . ? O63 C33 C23 110.8(2) . . ? O63 C33 C43 110.72(18) . . ? C23 C33 C43 108.40(19) . . ? O63 C33 H33 108.9 . . ? C23 C33 H33 108.9 . . ? C43 C33 H33 108.9 . . ? C33 O63 H63 109.5 . . ? C23 O53 H53 109.5 . . ? O23 C13 O13 124.6(2) . . ? O23 C13 C23 118.2(2) . . ? O13 C13 C23 117.1(2) . . ? O43 C43 O33 125.9(2) . . ? O43 C43 C33 116.7(2) . . ? O33 C43 C33 117.4(2) . . ? C14 C24 H24A 109.5 . . ? C14 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C14 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O14 C14 C34 122.5(4) . . ? O14 C14 C24 119.7(5) . . ? C34 C14 C24 117.8(4) . . ? C14 C34 H34C 109.5 . . ? C14 C34 H34B 109.5 . . ? H34C C34 H34B 109.5 . . ? C14 C34 H34A 109.5 . . ? H34C C34 H34A 109.5 . . ? H34B C34 H34A 109.5 . . ? O15 C15 C25 120.5(6) . . ? O15 C15 C35 120.2(6) . . ? C25 C15 C35 119.3(4) . . ? C15 C25 H25A 109.5 . . ? C15 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C15 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C15 C35 H35A 109.5 . . ? C15 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C15 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? O152 C152 C252 120.5(6) . . ? O152 C152 C352 120.2(6) . . ? C252 C152 C352 119.3(5) . . ? C152 C252 H25D 109.5 . . ? C152 C252 H25E 109.5 . . ? H25D C252 H25E 109.5 . . ? C152 C252 H25F 109.5 . . ? H25D C252 H25F 109.5 . . ? H25E C252 H25F 109.5 . . ? C152 C352 H35D 109.5 . . ? C152 C352 H35E 109.5 . . ? H35D C352 H35E 109.5 . . ? C152 C352 H35F 109.5 . . ? H35D C352 H35F 109.5 . . ? H35E C352 H35F 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 C631 C641 C651 C661 0.3(5) . . . . ? C651 C641 C631 C621 -0.5(4) . . . . ? C651 C641 C631 Cl21 179.4(3) . . . . ? C641 C651 C661 C611 -0.9(5) . . . . ? C651 C661 C611 C621 1.7(4) . . . . ? C651 C661 C611 C61 -178.4(3) . . . . ? N51 C51 C61 N11 170.2(3) . . . . ? N41 C51 C61 N11 -8.5(4) . . . . ? N51 C51 C61 C611 -7.9(4) . . . . ? N41 C51 C61 C611 173.4(2) . . . . ? C661 C611 C61 N11 -64.1(3) . . . . ? C621 C611 C61 N11 115.8(3) . . . . ? C661 C611 C61 C51 114.0(3) . . . . ? C621 C611 C61 C51 -66.1(3) . . . . ? C641 C631 C621 C611 1.4(4) . . . . ? Cl21 C631 C621 C611 -178.59(19) . . . . ? C641 C631 C621 Cl11 -177.4(2) . . . . ? Cl21 C631 C621 Cl11 2.7(3) . . . . ? C661 C611 C621 C631 -1.9(4) . . . . ? C61 C611 C621 C631 178.2(2) . . . . ? C661 C611 C621 Cl11 176.8(2) . . . . ? C61 C611 C621 Cl11 -3.1(3) . . . . ? N31 C31 N21 N11 171.2(2) . . . . ? N41 C31 N21 N11 -8.7(4) . . . . ? N51 C51 N41 C31 -174.1(2) . . . . ? C61 C51 N41 C31 4.6(3) . . . . ? N31 C31 N41 C51 -176.4(2) . . . . ? N21 C31 N41 C51 3.5(4) . . . . ? C51 C61 N11 N21 3.7(3) . . . . ? C611 C61 N11 N21 -178.2(2) . . . . ? C31 N21 N11 C61 4.7(3) . . . . ? C662 C652 C642 C632 0.1(5) . . . . ? C652 C642 C632 C622 -1.1(4) . . . . ? C652 C642 C632 Cl22 179.5(2) . . . . ? C642 C652 C662 C612 1.1(5) . . . . ? N52 C52 C62 N12 -166.7(3) . . . . ? N42 C52 C62 N12 12.6(4) . . . . ? N52 C52 C62 C612 10.2(4) . . . . ? N42 C52 C62 C612 -170.5(2) . . . . ? C652 C662 C612 C622 -1.2(4) . . . . ? C652 C662 C612 C62 176.8(3) . . . . ? N12 C62 C612 C662 69.1(3) . . . . ? C52 C62 C612 C662 -107.9(3) . . . . ? N12 C62 C612 C622 -112.9(3) . . . . ? C52 C62 C612 C622 70.1(3) . . . . ? N32 C32 N22 N12 -168.3(2) . . . . ? N42 C32 N22 N12 13.4(4) . . . . ? C642 C632 C622 C612 1.0(4) . . . . ? Cl22 C632 C622 C612 -179.60(19) . . . . ? C642 C632 C622 Cl12 179.2(2) . . . . ? Cl22 C632 C622 Cl12 -1.4(3) . . . . ? C662 C612 C622 C632 0.2(4) . . . . ? C62 C612 C622 C632 -177.9(2) . . . . ? C662 C612 C622 Cl12 -178.1(2) . . . . ? C62 C612 C622 Cl12 3.9(3) . . . . ? N52 C52 N42 C32 172.7(2) . . . . ? C62 C52 N42 C32 -6.6(3) . . . . ? N32 C32 N42 C52 176.0(2) . . . . ? N22 C32 N42 C52 -5.6(4) . . . . ? C52 C62 N12 N22 -5.3(3) . . . . ? C612 C62 N12 N22 177.6(2) . . . . ? C32 N22 N12 C62 -7.1(4) . . . . ? O53 C23 C33 O63 73.7(2) . . . . ? C13 C23 C33 O63 -51.1(2) . . . . ? O53 C23 C33 C43 -48.0(3) . . . . ? C13 C23 C33 C43 -172.77(19) . . . . ? O53 C23 C13 O23 -31.2(3) . . . . ? C33 C23 C13 O23 93.7(3) . . . . ? O53 C23 C13 O13 149.0(2) . . . . ? C33 C23 C13 O13 -86.2(3) . . . . ? O63 C33 C43 O43 163.8(2) . . . . ? C23 C33 C43 O43 -74.5(3) . . . . ? O63 C33 C43 O33 -15.9(3) . . . . ? C23 C33 C43 O33 105.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.510 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.090 # Attachment 'LM+5.(DMSO).cif' data_LM+5.(DMSO) _database_code_depnum_ccdc_archive 'CCDC 856209' #TrackingRef 'LM+5.(DMSO).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - L-tartrate - dimethyl sulfoxide (1:0.5:1) ; _chemical_absolute_configuration syn _chemical_name_common ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - L- tartrate -dimethyl sulfoxide (1:0.5:1) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C4 H4 O6, 2(C2 H6 O S)' _chemical_formula_sum 'C26 H32 Cl4 N10 O8 S2' _chemical_formula_weight 818.54 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.09610(10) _cell_length_b 11.04200(10) _cell_length_c 15.6858(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.9500(10) _cell_angle_gamma 90.00 _cell_volume 1838.39(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 27533 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 33.14 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 0.495 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.807 _exptl_absorpt_correction_T_max 0.857 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 41755 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 33.15 _reflns_number_total 13499 _reflns_number_gt 12361 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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^ > 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^)+(0.0457P)^2^+0.5197P] 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 -0.05(3) _refine_ls_number_reflns 13499 _refine_ls_number_parameters 468 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.003 _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 Cl11 Cl 0.53382(4) 0.26994(4) 0.16645(3) 0.04200(10) Uani 1 1 d . . . Cl21 Cl 0.35643(4) 0.44413(7) 0.02496(4) 0.05736(15) Uani 1 1 d . . . N11 N 0.82195(12) 0.39958(11) 0.33992(8) 0.0253(2) Uani 1 1 d . . . N21 N 0.89771(12) 0.32594(11) 0.40149(8) 0.0258(2) Uani 1 1 d . . . C31 C 0.93897(13) 0.21806(12) 0.38057(9) 0.0235(2) Uani 1 1 d . . . N31 N 1.00101(14) 0.14548(12) 0.44586(8) 0.0297(3) Uani 1 1 d . . . H311 H 1.0297 0.0754 0.4334 0.036 Uiso 1 1 calc R . . H312 H 1.0135 0.1673 0.5017 0.036 Uiso 1 1 calc R . . N41 N 0.92012(12) 0.18444(11) 0.29563(8) 0.0261(2) Uani 1 1 d . . . C51 C 0.85070(14) 0.25727(12) 0.23194(9) 0.0242(2) Uani 1 1 d . . . N51 N 0.83502(14) 0.22867(13) 0.14811(8) 0.0325(3) Uani 1 1 d . . . H511 H 0.8699 0.1626 0.1347 0.039 Uiso 1 1 calc R . . H512 H 0.7896 0.2756 0.1054 0.039 Uiso 1 1 calc R . . C61 C 0.79520(13) 0.36729(12) 0.25692(9) 0.0230(2) Uani 1 1 d . . . C611 C 0.70882(13) 0.44688(12) 0.18974(9) 0.0235(2) Uani 1 1 d . . . C621 C 0.58665(13) 0.41014(14) 0.14455(9) 0.0257(2) Uani 1 1 d . . . C631 C 0.50780(14) 0.48780(17) 0.08253(10) 0.0320(3) Uani 1 1 d . . . C641 C 0.54970(16) 0.60053(17) 0.06602(12) 0.0369(3) Uani 1 1 d . . . H641 H 0.4951 0.6532 0.0243 0.044 Uiso 1 1 calc R . . C651 C 0.67092(17) 0.63676(16) 0.11011(14) 0.0411(4) Uani 1 1 d . . . H651 H 0.7001 0.7140 0.0982 0.049 Uiso 1 1 calc R . . C661 C 0.75075(15) 0.55981(14) 0.17218(12) 0.0339(3) Uani 1 1 d . . . H661 H 0.8341 0.5850 0.2025 0.041 Uiso 1 1 calc R . . H21 H 0.910(2) 0.347(2) 0.4555(16) 0.041 Uiso 1 1 d . . . Cl12 Cl 0.46182(4) 0.47243(4) 0.32915(3) 0.03895(9) Uani 1 1 d . . . Cl22 Cl 0.64341(4) 0.31395(5) 0.48141(3) 0.04401(10) Uani 1 1 d . . . N12 N 0.18081(12) 0.32681(11) 0.16391(8) 0.0246(2) Uani 1 1 d . . . N22 N 0.10286(13) 0.39350(11) 0.09916(8) 0.0253(2) Uani 1 1 d . . . C32 C 0.05574(14) 0.50115(12) 0.11511(9) 0.0235(2) Uani 1 1 d . . . N32 N -0.00445(14) 0.56900(12) 0.04626(8) 0.0317(3) Uani 1 1 d . . . H321 H -0.0372 0.6388 0.0551 0.038 Uiso 1 1 calc R . . H322 H -0.0117 0.5443 -0.0084 0.038 Uiso 1 1 calc R . . N42 N 0.06668(13) 0.53897(11) 0.19817(8) 0.0259(2) Uani 1 1 d . . . C52 C 0.13719(13) 0.47128(13) 0.26480(8) 0.0236(2) Uani 1 1 d . . . N52 N 0.14372(15) 0.50055(13) 0.34738(8) 0.0324(3) Uani 1 1 d . . . H521 H 0.1020 0.5638 0.3580 0.039 Uiso 1 1 calc R . . H522 H 0.1898 0.4568 0.3920 0.039 Uiso 1 1 calc R . . C62 C 0.20322(13) 0.36540(12) 0.24534(9) 0.0230(2) Uani 1 1 d . . . C612 C 0.29086(13) 0.29405(12) 0.31726(9) 0.0229(2) Uani 1 1 d . . . C622 C 0.41242(14) 0.33525(13) 0.36029(9) 0.0246(2) Uani 1 1 d . . . C632 C 0.49238(13) 0.26593(14) 0.42731(10) 0.0274(3) Uani 1 1 d . . . C642 C 0.45236(16) 0.15659(16) 0.45287(11) 0.0355(3) Uani 1 1 d . . . H642 H 0.5076 0.1095 0.4985 0.043 Uiso 1 1 calc R . . C652 C 0.33063(18) 0.11638(16) 0.41117(13) 0.0406(4) Uani 1 1 d . . . H652 H 0.3018 0.0423 0.4291 0.049 Uiso 1 1 calc R . . C662 C 0.25129(15) 0.18453(15) 0.34338(12) 0.0333(3) Uani 1 1 d . . . H662 H 0.1688 0.1558 0.3145 0.040 Uiso 1 1 calc R . . H22 H 0.092(2) 0.367(2) 0.0468(16) 0.040 Uiso 1 1 d . . . O13 O 0.06156(13) 0.50629(10) 0.89147(7) 0.0333(2) Uani 1 1 d . . . O23 O 0.07074(13) 0.31315(10) 0.93267(7) 0.0336(2) Uani 1 1 d . . . O33 O -0.08543(11) 0.39144(10) 0.57230(6) 0.0284(2) Uani 1 1 d . . . O43 O -0.00609(12) 0.20750(10) 0.61591(7) 0.0311(2) Uani 1 1 d . . . O53 O -0.13939(11) 0.43137(12) 0.72365(7) 0.0343(2) Uani 1 1 d . . . H53 H -0.1523 0.4699 0.6756 0.051 Uiso 1 1 calc R . . O63 O 0.14096(10) 0.43921(11) 0.74776(7) 0.0283(2) Uani 1 1 d . . . H63 H 0.1013 0.5050 0.7382 0.042 Uiso 1 1 calc R . . C13 C -0.04957(13) 0.30825(13) 0.62896(8) 0.0242(2) Uani 1 1 d . . . C23 C -0.05930(13) 0.33198(12) 0.72340(8) 0.0236(2) Uani 1 1 d . . . H23 H -0.0942 0.2583 0.7447 0.028 Uiso 1 1 calc R . . C33 C 0.07456(13) 0.35530(12) 0.78458(8) 0.0219(2) Uani 1 1 d . . . H33 H 0.1214 0.2768 0.7922 0.026 Uiso 1 1 calc R . . C43 C 0.06829(13) 0.39548(12) 0.87696(8) 0.0226(2) Uani 1 1 d . . . S14 S 0.74176(4) 0.91472(5) 0.41250(3) 0.04130(11) Uani 1 1 d . . . O14 O 0.69170(15) 0.92440(18) 0.49207(8) 0.0513(4) Uani 1 1 d . . . C14 C 0.6899(2) 0.7718(3) 0.36265(17) 0.0584(6) Uani 1 1 d . . . H141 H 0.7459 0.7080 0.3953 0.088 Uiso 1 1 calc R . . H142 H 0.6914 0.7725 0.3005 0.088 Uiso 1 1 calc R . . H143 H 0.6038 0.7564 0.3647 0.088 Uiso 1 1 calc R . . C24 C 0.6395(2) 1.0085(3) 0.33052(14) 0.0573(6) Uani 1 1 d . . . H241 H 0.5521 0.9826 0.3212 0.086 Uiso 1 1 calc R . . H242 H 0.6610 1.0016 0.2744 0.086 Uiso 1 1 calc R . . H243 H 0.6489 1.0928 0.3508 0.086 Uiso 1 1 calc R . . S115 S 0.74911(5) 0.36325(7) 0.91721(4) 0.04241(13) Uani 0.78 1 d P A 1 C15 C 0.6740(3) 0.2710(3) 0.82527(17) 0.0688(7) Uani 0.78 1 d P A 1 H15A H 0.6986 0.1864 0.8392 0.103 Uiso 0.78 1 calc PR A 1 H15B H 0.6992 0.2966 0.7732 0.103 Uiso 0.78 1 calc PR A 1 H15C H 0.5824 0.2787 0.8123 0.103 Uiso 0.78 1 calc PR A 1 C25 C 0.6925(3) 0.5039(3) 0.87711(19) 0.0696(7) Uani 0.78 1 d P A 1 H25A H 0.7275 0.5654 0.9226 0.104 Uiso 0.78 1 calc PR A 1 H25B H 0.6004 0.5042 0.8624 0.104 Uiso 0.78 1 calc PR A 1 H25C H 0.7175 0.5220 0.8235 0.104 Uiso 0.78 1 calc PR A 1 O15 O 0.68654(17) 0.32802(17) 0.98878(9) 0.0550(4) Uani 0.78 1 d P A 1 S125 S 0.62800(19) 0.3600(2) 0.89273(12) 0.0396(4) Uani 0.22 1 d P B 2 C15B C 0.6740(3) 0.2710(3) 0.82527(17) 0.0688(7) Uani 0.22 1 d P B 2 H15D H 0.6431 0.1887 0.8294 0.103 Uiso 0.22 1 calc PR B 2 H15E H 0.7662 0.2702 0.8418 0.103 Uiso 0.22 1 calc PR B 2 H15F H 0.6403 0.3005 0.7640 0.103 Uiso 0.22 1 calc PR B 2 C25B C 0.6925(3) 0.5039(3) 0.87711(19) 0.0696(7) Uani 0.22 1 d P B 2 H25D H 0.6688 0.5644 0.9150 0.104 Uiso 0.22 1 calc PR B 2 H25E H 0.6596 0.5282 0.8145 0.104 Uiso 0.22 1 calc PR B 2 H25F H 0.7846 0.4979 0.8932 0.104 Uiso 0.22 1 calc PR B 2 O15B O 0.68654(17) 0.32802(17) 0.98878(9) 0.0550(4) Uani 0.22 1 d P B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl11 0.0429(2) 0.03496(19) 0.0471(2) 0.00089(17) 0.01149(17) -0.01609(17) Cl21 0.02773(19) 0.0766(4) 0.0555(3) 0.0036(3) -0.00707(18) -0.0109(2) N11 0.0311(6) 0.0213(5) 0.0224(5) -0.0009(4) 0.0060(4) 0.0013(4) N21 0.0352(6) 0.0229(5) 0.0177(4) -0.0008(4) 0.0052(4) 0.0028(5) C31 0.0292(6) 0.0215(6) 0.0203(5) -0.0003(4) 0.0080(4) 0.0009(5) N31 0.0421(7) 0.0263(5) 0.0192(5) 0.0018(4) 0.0068(5) 0.0084(5) N41 0.0348(6) 0.0240(5) 0.0190(5) -0.0004(4) 0.0072(4) 0.0056(5) C51 0.0313(6) 0.0213(6) 0.0198(5) -0.0016(4) 0.0071(5) 0.0015(5) N51 0.0481(8) 0.0298(6) 0.0185(5) -0.0018(4) 0.0077(5) 0.0106(5) C61 0.0263(6) 0.0202(5) 0.0212(5) -0.0003(4) 0.0049(4) 0.0003(5) C611 0.0255(6) 0.0209(5) 0.0228(5) -0.0012(4) 0.0048(4) -0.0004(5) C621 0.0264(6) 0.0264(6) 0.0241(5) -0.0027(5) 0.0068(5) -0.0043(5) C631 0.0223(6) 0.0415(8) 0.0287(6) -0.0023(6) 0.0018(5) -0.0027(6) C641 0.0312(7) 0.0369(8) 0.0362(8) 0.0086(6) -0.0004(6) 0.0066(6) C651 0.0359(8) 0.0276(7) 0.0505(10) 0.0126(7) -0.0020(7) -0.0021(6) C661 0.0278(7) 0.0237(6) 0.0424(8) 0.0050(6) -0.0024(6) -0.0028(5) Cl12 0.0452(2) 0.03201(18) 0.0403(2) 0.00081(15) 0.01355(17) -0.01374(16) Cl22 0.02721(17) 0.0503(2) 0.0468(2) -0.00903(19) -0.00128(15) -0.00530(17) N12 0.0327(6) 0.0201(5) 0.0212(5) -0.0005(4) 0.0082(4) 0.0019(4) N22 0.0366(6) 0.0208(5) 0.0180(4) -0.0022(4) 0.0073(4) 0.0039(4) C32 0.0297(6) 0.0216(5) 0.0189(5) -0.0008(4) 0.0066(4) 0.0023(5) N32 0.0484(7) 0.0273(6) 0.0177(5) 0.0007(4) 0.0072(5) 0.0112(5) N42 0.0351(6) 0.0239(5) 0.0179(4) -0.0005(4) 0.0063(4) 0.0074(4) C52 0.0306(6) 0.0212(5) 0.0184(5) -0.0007(4) 0.0061(4) 0.0033(5) N52 0.0473(7) 0.0311(6) 0.0184(5) 0.0004(4) 0.0090(5) 0.0142(6) C62 0.0288(6) 0.0198(5) 0.0204(5) -0.0006(4) 0.0071(4) 0.0019(5) C612 0.0259(6) 0.0199(5) 0.0217(5) -0.0007(4) 0.0049(4) 0.0016(4) C622 0.0285(6) 0.0226(6) 0.0236(5) -0.0024(4) 0.0094(5) -0.0020(5) C632 0.0237(6) 0.0300(6) 0.0260(6) -0.0054(5) 0.0034(5) 0.0005(5) C642 0.0346(8) 0.0301(7) 0.0340(8) 0.0044(6) -0.0022(6) 0.0043(6) C652 0.0390(8) 0.0265(7) 0.0467(9) 0.0127(6) -0.0028(7) -0.0040(6) C662 0.0287(7) 0.0253(6) 0.0391(8) 0.0067(6) -0.0007(6) -0.0044(5) O13 0.0579(7) 0.0204(4) 0.0262(5) -0.0001(4) 0.0197(5) 0.0008(5) O23 0.0608(7) 0.0217(5) 0.0179(4) -0.0003(4) 0.0107(4) -0.0047(5) O33 0.0363(5) 0.0268(5) 0.0185(4) 0.0003(3) 0.0023(4) -0.0015(4) O43 0.0503(6) 0.0227(5) 0.0221(4) -0.0014(4) 0.0135(4) -0.0022(4) O53 0.0334(5) 0.0401(6) 0.0271(5) -0.0003(4) 0.0053(4) 0.0131(5) O63 0.0311(5) 0.0314(5) 0.0248(4) -0.0009(4) 0.0119(4) -0.0036(4) C13 0.0290(6) 0.0251(6) 0.0177(5) -0.0026(4) 0.0054(4) -0.0068(5) C23 0.0282(6) 0.0241(6) 0.0185(5) -0.0025(4) 0.0069(4) -0.0019(5) C33 0.0283(6) 0.0207(5) 0.0164(5) 0.0008(4) 0.0058(4) 0.0032(4) C43 0.0274(6) 0.0223(5) 0.0172(5) -0.0009(4) 0.0053(4) -0.0020(4) S14 0.0361(2) 0.0605(3) 0.02704(17) -0.00236(18) 0.00880(15) -0.00819(19) O14 0.0568(8) 0.0738(11) 0.0254(5) -0.0072(6) 0.0154(5) -0.0192(8) C14 0.0610(13) 0.0611(14) 0.0549(13) -0.0137(11) 0.0199(10) -0.0054(11) C24 0.0600(13) 0.0761(16) 0.0422(10) 0.0135(10) 0.0248(9) 0.0221(12) S115 0.0311(2) 0.0528(3) 0.0418(3) -0.0004(2) 0.0082(2) 0.0058(2) C15 0.0878(19) 0.0786(18) 0.0513(12) -0.0177(13) 0.0380(13) -0.0214(15) C25 0.096(2) 0.0600(15) 0.0575(14) 0.0100(12) 0.0304(14) -0.0028(15) O15 0.0736(10) 0.0613(10) 0.0264(6) 0.0084(6) 0.0087(6) 0.0136(9) S125 0.0341(8) 0.0569(12) 0.0282(7) 0.0067(8) 0.0095(6) 0.0071(8) C15B 0.0878(19) 0.0786(18) 0.0513(12) -0.0177(13) 0.0380(13) -0.0214(15) C25B 0.096(2) 0.0600(15) 0.0575(14) 0.0100(12) 0.0304(14) -0.0028(15) O15B 0.0736(10) 0.0613(10) 0.0264(6) 0.0084(6) 0.0087(6) 0.0136(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl11 C621 1.7250(15) . ? Cl21 C631 1.7276(16) . ? N11 C61 1.2981(17) . ? N11 N21 1.3518(17) . ? N21 C31 1.3505(18) . ? N21 H21 0.85(2) . ? C31 N31 1.3243(18) . ? C31 N41 1.3396(17) . ? N31 H311 0.8800 . ? N31 H312 0.8800 . ? N41 C51 1.3376(18) . ? C51 N51 1.3136(17) . ? C51 C61 1.4661(19) . ? N51 H511 0.8800 . ? N51 H512 0.8800 . ? C61 C611 1.4875(19) . ? C611 C661 1.386(2) . ? C611 C621 1.3944(19) . ? C621 C631 1.397(2) . ? C631 C641 1.379(3) . ? C641 C651 1.380(2) . ? C641 H641 0.9500 . ? C651 C661 1.397(2) . ? C651 H651 0.9500 . ? C661 H661 0.9500 . ? Cl12 C622 1.7290(14) . ? Cl22 C632 1.7264(15) . ? N12 C62 1.2999(17) . ? N12 N22 1.3452(16) . ? N22 C32 1.3510(17) . ? N22 H22 0.85(2) . ? C32 N32 1.3241(18) . ? C32 N42 1.3395(17) . ? N32 H321 0.8800 . ? N32 H322 0.8800 . ? N42 C52 1.3365(17) . ? C52 N52 1.3164(17) . ? C52 C62 1.4585(19) . ? N52 H521 0.8800 . ? N52 H522 0.8800 . ? C62 C612 1.4831(18) . ? C612 C662 1.389(2) . ? C612 C622 1.3968(19) . ? C622 C632 1.391(2) . ? C632 C642 1.385(2) . ? C642 C652 1.391(2) . ? C642 H642 0.9500 . ? C652 C662 1.388(2) . ? C652 H652 0.9500 . ? C662 H662 0.9500 . ? O13 C43 1.2507(17) . ? O23 C43 1.2558(16) . ? O33 C13 1.2594(17) . ? O43 C13 1.2530(18) . ? O53 C23 1.4129(17) . ? O53 H53 0.8400 . ? O63 C33 1.4083(17) . ? O63 H63 0.8400 . ? C13 C23 1.5388(18) . ? C23 C33 1.5370(19) . ? C23 H23 1.0000 . ? C33 C43 1.5363(17) . ? C33 H33 1.0000 . ? S14 O14 1.5106(14) . ? S14 C24 1.778(2) . ? S14 C14 1.780(3) . ? C14 H141 0.9800 . ? C14 H142 0.9800 . ? C14 H143 0.9800 . ? C24 H241 0.9800 . ? C24 H242 0.9800 . ? C24 H243 0.9800 . ? S115 O15 1.5323(18) . ? S115 C25 1.723(3) . ? S115 C15 1.764(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C61 N11 N21 117.65(12) . . ? C31 N21 N11 122.77(12) . . ? C31 N21 H21 120.9(16) . . ? N11 N21 H21 115.8(16) . . ? N31 C31 N41 119.79(13) . . ? N31 C31 N21 118.85(12) . . ? N41 C31 N21 121.36(12) . . ? C31 N31 H311 120.0 . . ? C31 N31 H312 120.0 . . ? H311 N31 H312 120.0 . . ? C51 N41 C31 117.72(12) . . ? N51 C51 N41 118.85(13) . . ? N51 C51 C61 121.56(13) . . ? N41 C51 C61 119.59(12) . . ? C51 N51 H511 120.0 . . ? C51 N51 H512 120.0 . . ? H511 N51 H512 120.0 . . ? N11 C61 C51 120.31(12) . . ? N11 C61 C611 117.38(12) . . ? C51 C61 C611 122.30(11) . . ? C661 C611 C621 119.57(13) . . ? C661 C611 C61 119.20(13) . . ? C621 C611 C61 121.22(12) . . ? C611 C621 C631 119.61(13) . . ? C611 C621 Cl11 119.76(11) . . ? C631 C621 Cl11 120.63(11) . . ? C641 C631 C621 120.52(14) . . ? C641 C631 Cl21 118.90(13) . . ? C621 C631 Cl21 120.58(13) . . ? C631 C641 C651 120.01(15) . . ? C631 C641 H641 120.0 . . ? C651 C641 H641 120.0 . . ? C641 C651 C661 120.01(16) . . ? C641 C651 H651 120.0 . . ? C661 C651 H651 120.0 . . ? C611 C661 C651 120.28(14) . . ? C611 C661 H661 119.9 . . ? C651 C661 H661 119.9 . . ? C62 N12 N22 117.33(12) . . ? N12 N22 C32 122.69(11) . . ? N12 N22 H22 114.9(16) . . ? C32 N22 H22 122.1(16) . . ? N32 C32 N42 119.87(13) . . ? N32 C32 N22 118.50(12) . . ? N42 C32 N22 121.62(12) . . ? C32 N32 H321 120.0 . . ? C32 N32 H322 120.0 . . ? H321 N32 H322 120.0 . . ? C52 N42 C32 116.91(12) . . ? N52 C52 N42 118.95(13) . . ? N52 C52 C62 121.05(12) . . ? N42 C52 C62 119.99(12) . . ? C52 N52 H521 120.0 . . ? C52 N52 H522 120.0 . . ? H521 N52 H522 120.0 . . ? N12 C62 C52 120.30(12) . . ? N12 C62 C612 117.94(12) . . ? C52 C62 C612 121.64(11) . . ? C662 C612 C622 119.01(13) . . ? C662 C612 C62 119.57(13) . . ? C622 C612 C62 121.41(12) . . ? C632 C622 C612 119.95(13) . . ? C632 C622 Cl12 120.71(11) . . ? C612 C622 Cl12 119.33(11) . . ? C642 C632 C622 120.71(14) . . ? C642 C632 Cl22 118.20(12) . . ? C622 C632 Cl22 121.09(12) . . ? C632 C642 C652 119.43(15) . . ? C632 C642 H642 120.3 . . ? C652 C642 H642 120.3 . . ? C662 C652 C642 119.97(15) . . ? C662 C652 H652 120.0 . . ? C642 C652 H652 120.0 . . ? C652 C662 C612 120.91(14) . . ? C652 C662 H662 119.5 . . ? C612 C662 H662 119.5 . . ? C23 O53 H53 109.5 . . ? C33 O63 H63 109.5 . . ? O43 C13 O33 126.14(12) . . ? O43 C13 C23 116.55(12) . . ? O33 C13 C23 117.31(13) . . ? O53 C23 C33 111.24(11) . . ? O53 C23 C13 110.83(11) . . ? C33 C23 C13 107.66(11) . . ? O53 C23 H23 109.0 . . ? C33 C23 H23 109.0 . . ? C13 C23 H23 109.0 . . ? O63 C33 C43 111.70(11) . . ? O63 C33 C23 112.34(10) . . ? C43 C33 C23 109.64(11) . . ? O63 C33 H33 107.6 . . ? C43 C33 H33 107.6 . . ? C23 C33 H33 107.6 . . ? O13 C43 O23 124.88(12) . . ? O13 C43 C33 118.41(12) . . ? O23 C43 C33 116.71(12) . . ? O14 S14 C24 104.20(10) . . ? O14 S14 C14 106.02(11) . . ? C24 S14 C14 98.16(14) . . ? S14 C14 H141 109.5 . . ? S14 C14 H142 109.5 . . ? H141 C14 H142 109.5 . . ? S14 C14 H143 109.5 . . ? H141 C14 H143 109.5 . . ? H142 C14 H143 109.5 . . ? S14 C24 H241 109.5 . . ? S14 C24 H242 109.5 . . ? H241 C24 H242 109.5 . . ? S14 C24 H243 109.5 . . ? H241 C24 H243 109.5 . . ? H242 C24 H243 109.5 . . ? O15 S115 C25 107.55(12) . . ? O15 S115 C15 104.20(12) . . ? C25 S115 C15 100.77(16) . . ? S115 C15 H15A 109.5 . . ? S115 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? S115 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? S115 C25 H25A 109.5 . . ? S115 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S115 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 C61 N11 N21 C31 -4.4(2) . . . . ? N11 N21 C31 N31 -172.46(14) . . . . ? N11 N21 C31 N41 8.6(2) . . . . ? N31 C31 N41 C51 176.17(14) . . . . ? N21 C31 N41 C51 -4.9(2) . . . . ? C31 N41 C51 N51 177.35(15) . . . . ? C31 N41 C51 C61 -2.0(2) . . . . ? N21 N11 C61 C51 -2.6(2) . . . . ? N21 N11 C61 C611 178.28(12) . . . . ? N51 C51 C61 N11 -173.37(15) . . . . ? N41 C51 C61 N11 5.9(2) . . . . ? N51 C51 C61 C611 5.7(2) . . . . ? N41 C51 C61 C611 -175.01(13) . . . . ? N11 C61 C611 C661 70.09(19) . . . . ? C51 C61 C611 C661 -108.99(17) . . . . ? N11 C61 C611 C621 -109.65(16) . . . . ? C51 C61 C611 C621 71.27(19) . . . . ? C661 C611 C621 C631 -0.3(2) . . . . ? C61 C611 C621 C631 179.39(13) . . . . ? C661 C611 C621 Cl11 -179.76(13) . . . . ? C61 C611 C621 Cl11 -0.02(19) . . . . ? C611 C621 C631 C641 -0.3(2) . . . . ? Cl11 C621 C631 C641 179.11(13) . . . . ? C611 C621 C631 Cl21 179.49(11) . . . . ? Cl11 C621 C631 Cl21 -1.10(19) . . . . ? C621 C631 C641 C651 0.8(3) . . . . ? Cl21 C631 C641 C651 -178.96(16) . . . . ? C631 C641 C651 C661 -0.7(3) . . . . ? C621 C611 C661 C651 0.5(3) . . . . ? C61 C611 C661 C651 -179.28(17) . . . . ? C641 C651 C661 C611 0.1(3) . . . . ? C62 N12 N22 C32 4.9(2) . . . . ? N12 N22 C32 N32 169.93(14) . . . . ? N12 N22 C32 N42 -11.3(2) . . . . ? N32 C32 N42 C52 -174.68(15) . . . . ? N22 C32 N42 C52 6.5(2) . . . . ? C32 N42 C52 N52 -175.51(15) . . . . ? C32 N42 C52 C62 3.2(2) . . . . ? N22 N12 C62 C52 5.0(2) . . . . ? N22 N12 C62 C612 -178.88(12) . . . . ? N52 C52 C62 N12 169.39(15) . . . . ? N42 C52 C62 N12 -9.3(2) . . . . ? N52 C52 C62 C612 -6.6(2) . . . . ? N42 C52 C62 C612 174.73(13) . . . . ? N12 C62 C612 C662 -73.90(19) . . . . ? C52 C62 C612 C662 102.17(17) . . . . ? N12 C62 C612 C622 106.85(16) . . . . ? C52 C62 C612 C622 -77.08(18) . . . . ? C662 C612 C622 C632 0.9(2) . . . . ? C62 C612 C622 C632 -179.81(13) . . . . ? C662 C612 C622 Cl12 -179.20(12) . . . . ? C62 C612 C622 Cl12 0.05(18) . . . . ? C612 C622 C632 C642 -0.8(2) . . . . ? Cl12 C622 C632 C642 179.35(13) . . . . ? C612 C622 C632 Cl22 179.69(11) . . . . ? Cl12 C622 C632 Cl22 -0.18(17) . . . . ? C622 C632 C642 C652 -0.3(3) . . . . ? Cl22 C632 C642 C652 179.24(16) . . . . ? C632 C642 C652 C662 1.2(3) . . . . ? C642 C652 C662 C612 -1.1(3) . . . . ? C622 C612 C662 C652 0.0(2) . . . . ? C62 C612 C662 C652 -179.27(17) . . . . ? O43 C13 C23 O53 -163.99(13) . . . . ? O33 C13 C23 O53 16.22(17) . . . . ? O43 C13 C23 C33 74.15(15) . . . . ? O33 C13 C23 C33 -105.64(14) . . . . ? O53 C23 C33 O63 -73.64(13) . . . . ? C13 C23 C33 O63 47.97(15) . . . . ? O53 C23 C33 C43 51.19(15) . . . . ? C13 C23 C33 C43 172.80(10) . . . . ? O63 C33 C43 O13 33.84(18) . . . . ? C23 C33 C43 O13 -91.35(16) . . . . ? O63 C33 C43 O23 -145.96(13) . . . . ? C23 C33 C43 O23 88.85(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N31 H311 O33 0.88 2.13 2.9971(17) 167.1 2_646 N31 H312 O43 0.88 1.92 2.7771(16) 164.8 1_655 N51 H511 O13 0.88 1.98 2.8544(17) 175.2 2_646 N51 H512 O15 0.88 1.94 2.7862(19) 160.4 1_554 N51 H512 O15B 0.88 1.94 2.7862(19) 160.4 1_554 N51 H512 S115 0.88 3.01 3.7712(14) 145.5 1_554 N21 H21 O33 0.85(2) 1.88(2) 2.7284(15) 173(2) 1_655 N32 H321 O23 0.88 1.98 2.8390(17) 164.7 2_556 N32 H322 O13 0.88 2.01 2.8192(17) 151.8 1_554 N52 H521 O43 0.88 2.02 2.8980(17) 179.1 2_556 N52 H522 O14 0.88 1.94 2.7753(19) 157.4 2_646 N52 H522 S14 0.88 2.97 3.7294(13) 145.1 2_646 N22 H22 O23 0.85(2) 1.84(2) 2.6817(15) 178(2) 1_554 O53 H53 O33 0.84 2.15 2.6491(15) 117.8 . O63 H63 N41 0.84 2.05 2.8260(17) 154.0 2_656 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 33.15 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.650 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.047 # Attachment 'LM+6.(DMSO).cif' data_LM+6.(DMSO) _database_code_depnum_ccdc_archive 'CCDC 856210' #TrackingRef 'LM+6.(DMSO).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - D-malic - dimethyl sulfoxide (2:1:2) ; _chemical_absolute_configuration syn _chemical_name_common ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - D- malic -dimethyl sulfoxide (2:1:2) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C4 H4 O5, 2(C2 H6 O S)' _chemical_formula_sum 'C26 H32 Cl4 N10 O7 S2' _chemical_formula_weight 802.54 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.0150(2) _cell_length_b 10.8376(2) _cell_length_c 15.9178(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.1110(10) _cell_angle_gamma 90.00 _cell_volume 1806.06(6) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 15786 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 828 _exptl_absorpt_coefficient_mu 0.500 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.863 _exptl_absorpt_correction_T_max 0.944 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 22975 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.88 _reflns_number_total 8323 _reflns_number_gt 6486 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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^)+(0.0645P)^2^+0.5632P] 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 0.00(7) _refine_ls_number_reflns 8323 _refine_ls_number_parameters 469 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1333 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 H21 H 0.603(4) 0.449(4) 0.033(3) 0.055(13) Uiso 1 1 d . . . H22 H 0.409(3) 0.472(4) 0.447(3) 0.026(10) Uiso 1 1 d . . . Cl11 Cl 0.96976(10) 0.36606(9) 0.33554(7) 0.0445(3) Uani 1 1 d . . . Cl21 Cl 1.14813(10) 0.54219(13) 0.47920(8) 0.0580(3) Uani 1 1 d . . . N11 N 0.6826(3) 0.4990(3) 0.15930(18) 0.0268(6) Uani 1 1 d . . . N21 N 0.6052(3) 0.4251(3) 0.0961(2) 0.0283(6) Uani 1 1 d . . . C31 C 0.5627(3) 0.3153(3) 0.1154(2) 0.0252(7) Uani 1 1 d . . . N31 N 0.5012(3) 0.2428(3) 0.0501(2) 0.0337(7) Uani 1 1 d . . . H31A H 0.4712 0.1715 0.0612 0.040 Uiso 1 1 calc R . . H31B H 0.4900 0.2654 -0.0049 0.040 Uiso 1 1 calc R . . N41 N 0.5794(3) 0.2801(3) 0.19911(19) 0.0291(7) Uani 1 1 d . . . C51 C 0.6477(3) 0.3554(3) 0.2635(2) 0.0285(8) Uani 1 1 d . . . N51 N 0.6590(3) 0.3280(3) 0.3465(2) 0.0341(7) Uani 1 1 d . . . H51A H 0.6221 0.2613 0.3588 0.041 Uiso 1 1 calc R . . H51B H 0.7034 0.3764 0.3895 0.041 Uiso 1 1 calc R . . C61 C 0.7063(3) 0.4657(3) 0.2400(2) 0.0265(8) Uani 1 1 d . . . C611 C 0.7935(3) 0.5471(3) 0.3093(2) 0.0275(7) Uani 1 1 d . . . C621 C 0.7515(4) 0.6610(4) 0.3268(3) 0.0388(10) Uani 1 1 d . . . H621 H 0.6672 0.6871 0.2953 0.047 Uiso 1 1 calc R . . C631 C 0.8310(4) 0.7384(4) 0.3902(3) 0.0466(11) Uani 1 1 d . . . H631 H 0.8012 0.8171 0.4013 0.056 Uiso 1 1 calc R . . C641 C 0.9521(4) 0.7015(4) 0.4364(3) 0.0389(9) Uani 1 1 d . . . H641 H 1.0063 0.7542 0.4797 0.047 Uiso 1 1 calc R . . C651 C 0.9951(3) 0.5873(4) 0.4199(2) 0.0339(9) Uani 1 1 d . . . C661 C 0.9162(3) 0.5091(4) 0.3567(2) 0.0285(8) Uani 1 1 d . . . Cl12 Cl 0.03852(9) 0.55462(9) 0.16749(7) 0.0412(2) Uani 1 1 d . . . Cl22 Cl -0.13993(9) 0.38559(11) 0.01846(7) 0.0496(3) Uani 1 1 d . . . N12 N 0.3248(3) 0.4163(3) 0.33961(19) 0.0288(6) Uani 1 1 d . . . N22 N 0.4002(3) 0.4900(3) 0.4028(2) 0.0287(7) Uani 1 1 d . . . C32 C 0.4434(3) 0.6006(3) 0.3854(2) 0.0279(8) Uani 1 1 d . . . N32 N 0.5019(3) 0.6727(3) 0.4536(2) 0.0343(7) Uani 1 1 d . . . H32A H 0.5321 0.7449 0.4446 0.041 Uiso 1 1 calc R . . H32B H 0.5103 0.6481 0.5078 0.041 Uiso 1 1 calc R . . N42 N 0.4298(3) 0.6363(3) 0.30306(19) 0.0290(7) Uani 1 1 d . . . C52 C 0.3632(3) 0.5633(3) 0.2379(2) 0.0253(7) Uani 1 1 d . . . N52 N 0.3551(3) 0.5910(3) 0.1565(2) 0.0341(7) Uani 1 1 d . . . H52A H 0.3935 0.6574 0.1453 0.041 Uiso 1 1 calc R . . H52B H 0.3112 0.5434 0.1128 0.041 Uiso 1 1 calc R . . C62 C 0.3024(3) 0.4530(3) 0.2580(2) 0.0246(7) Uani 1 1 d . . . C612 C 0.2165(3) 0.3752(3) 0.1881(2) 0.0257(7) Uani 1 1 d . . . C622 C 0.0929(3) 0.4136(3) 0.1421(2) 0.0281(8) Uani 1 1 d . . . C632 C 0.0143(3) 0.3392(4) 0.0762(2) 0.0331(9) Uani 1 1 d . . . C642 C 0.0574(4) 0.2268(4) 0.0557(3) 0.0383(9) Uani 1 1 d . . . H642 H 0.0032 0.1762 0.0108 0.046 Uiso 1 1 calc R . . C652 C 0.1805(4) 0.1887(4) 0.1014(3) 0.0390(9) Uani 1 1 d . . . H652 H 0.2110 0.1121 0.0869 0.047 Uiso 1 1 calc R . . C662 C 0.2593(4) 0.2609(3) 0.1677(3) 0.0339(9) Uani 1 1 d . . . H662 H 0.3426 0.2328 0.1995 0.041 Uiso 1 1 calc R . . O13 O 0.4776(3) 0.8050(2) 0.11447(16) 0.0324(6) Uani 1 1 d . . . O23 O 0.4132(2) 0.9950(2) 0.06797(15) 0.0295(5) Uani 1 1 d . . . O33 O 0.5670(3) 0.9181(3) 0.43050(16) 0.0413(7) Uani 1 1 d . . . O43 O 0.5376(3) 1.1114(2) 0.38277(17) 0.0342(6) Uani 1 1 d . . . O53 O 0.6457(2) 1.0299(2) 0.25296(17) 0.0425(6) Uani 1 1 d . . . H53 H 0.6085 1.0961 0.2325 0.064 Uiso 1 1 calc R . . C13 C 0.5553(3) 0.9997(4) 0.3725(2) 0.0267(7) Uani 1 1 d . . . C23 C 0.5647(3) 0.9568(3) 0.2830(2) 0.0287(8) Uani 1 1 d . . . H23 H 0.6029 0.8722 0.2922 0.034 Uiso 1 1 calc R . . C33 C 0.4314(3) 0.9441(4) 0.2168(2) 0.0300(8) Uani 1 1 d . . . H33A H 0.3840 1.0225 0.2137 0.036 Uiso 1 1 calc R . . H33B H 0.3839 0.8783 0.2364 0.036 Uiso 1 1 calc R . . C43 C 0.4414(3) 0.9125(3) 0.1258(2) 0.0250(7) Uani 1 1 d . . . S114 S 0.24647(11) 0.48835(13) 0.91753(8) 0.0453(3) Uani 0.90 1 d P A 1 C114 C 0.1439(5) 0.5828(5) 0.8338(3) 0.0644(14) Uani 0.90 1 d P A 1 H11A H 0.1613 0.6699 0.8497 0.097 Uiso 0.90 1 calc PR A 1 H11B H 0.0547 0.5640 0.8283 0.097 Uiso 0.90 1 calc PR A 1 H11C H 0.1591 0.5666 0.7774 0.097 Uiso 0.90 1 calc PR A 1 C214 C 0.1920(5) 0.3423(5) 0.8692(3) 0.0665(14) Uani 0.90 1 d P A 1 H21A H 0.2398 0.2765 0.9077 0.100 Uiso 0.90 1 calc PR A 1 H21B H 0.2055 0.3366 0.8113 0.100 Uiso 0.90 1 calc PR A 1 H21C H 0.1008 0.3334 0.8620 0.100 Uiso 0.90 1 calc PR A 1 S124 S 0.1325(14) 0.4585(15) 0.9040(10) 0.066(4) Uani 0.10 1 d P A 2 C124 C 0.1439(5) 0.5828(5) 0.8338(3) 0.0644(14) Uani 0.10 1 d P A 2 H12A H 0.1087 0.6578 0.8518 0.097 Uiso 0.10 1 calc PR A 2 H12B H 0.0955 0.5627 0.7725 0.097 Uiso 0.10 1 calc PR A 2 H12C H 0.2337 0.5965 0.8385 0.097 Uiso 0.10 1 calc PR A 2 C224 C 0.1920(5) 0.3423(5) 0.8692(3) 0.0665(14) Uani 0.10 1 d P A 2 H22A H 0.1893 0.2701 0.9056 0.100 Uiso 0.10 1 calc PR A 2 H22B H 0.2808 0.3601 0.8731 0.100 Uiso 0.10 1 calc PR A 2 H22C H 0.1425 0.3255 0.8076 0.100 Uiso 0.10 1 calc PR A 2 O14 O 0.1972(3) 0.5004(4) 0.99486(19) 0.0582(9) Uani 1 1 d . . . S115 S 0.24905(18) 0.9591(2) 0.42169(14) 0.0477(5) Uani 0.57 1 d P B 1 C115 C 0.1712(6) 0.8636(6) 0.3308(4) 0.0746(16) Uani 0.57 1 d P B 1 H11D H 0.1929 0.7771 0.3465 0.112 Uiso 0.57 1 calc PR B 1 H11E H 0.1989 0.8860 0.2800 0.112 Uiso 0.57 1 calc PR B 1 H11F H 0.0785 0.8747 0.3156 0.112 Uiso 0.57 1 calc PR B 1 C215 C 0.1947(6) 1.1026(6) 0.3769(4) 0.0780(17) Uani 0.57 1 d P B 1 H21D H 0.2311 1.1670 0.4207 0.117 Uiso 0.57 1 calc PR B 1 H21E H 0.1013 1.1051 0.3605 0.117 Uiso 0.57 1 calc PR B 1 H21F H 0.2211 1.1166 0.3243 0.117 Uiso 0.57 1 calc PR B 1 S125 S 0.1303(3) 0.9644(3) 0.39838(18) 0.0501(7) Uani 0.43 1 d P B 2 C125 C 0.1712(6) 0.8636(6) 0.3308(4) 0.0746(16) Uani 0.43 1 d P B 2 H12D H 0.1389 0.7813 0.3382 0.112 Uiso 0.43 1 calc PR B 2 H12E H 0.2644 0.8606 0.3458 0.112 Uiso 0.43 1 calc PR B 2 H12F H 0.1339 0.8902 0.2693 0.112 Uiso 0.43 1 calc PR B 2 C225 C 0.1947(6) 1.1026(6) 0.3769(4) 0.0780(17) Uani 0.43 1 d P B 2 H22D H 0.1758 1.1681 0.4134 0.117 Uiso 0.43 1 calc PR B 2 H22E H 0.1573 1.1237 0.3143 0.117 Uiso 0.43 1 calc PR B 2 H22F H 0.2875 1.0939 0.3909 0.117 Uiso 0.43 1 calc PR B 2 O15 O 0.1925(3) 0.9292(4) 0.4926(2) 0.0640(9) 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 Cl11 0.0474(6) 0.0356(5) 0.0505(6) 0.0027(5) 0.0152(5) 0.0158(5) Cl21 0.0311(5) 0.0733(8) 0.0569(7) 0.0066(6) -0.0048(5) 0.0059(5) N11 0.0331(15) 0.0205(14) 0.0271(15) -0.0003(13) 0.0100(12) -0.0016(13) N21 0.0344(16) 0.0249(15) 0.0256(15) 0.0011(13) 0.0095(12) -0.0027(13) C31 0.0313(18) 0.0208(17) 0.0223(18) 0.0015(14) 0.0064(14) -0.0022(14) N31 0.0488(19) 0.0272(16) 0.0232(16) 0.0005(13) 0.0082(14) -0.0109(15) N41 0.0384(16) 0.0227(15) 0.0251(16) 0.0006(13) 0.0083(13) -0.0027(13) C51 0.0352(18) 0.0229(18) 0.0273(19) -0.0017(15) 0.0095(15) 0.0028(15) N51 0.0500(19) 0.0272(16) 0.0246(16) 0.0008(13) 0.0109(13) -0.0097(14) C61 0.0287(17) 0.0223(18) 0.0287(19) 0.0016(14) 0.0090(14) 0.0000(14) C611 0.0330(17) 0.0234(17) 0.0274(18) 0.0007(15) 0.0111(14) -0.0025(16) C621 0.0242(19) 0.030(2) 0.054(3) -0.0062(18) 0.0003(17) 0.0049(16) C631 0.041(2) 0.032(2) 0.058(3) -0.013(2) 0.0027(19) 0.0015(18) C641 0.036(2) 0.038(2) 0.037(2) -0.0074(18) 0.0010(17) -0.0084(18) C651 0.0275(17) 0.043(2) 0.0278(19) 0.0046(17) 0.0040(15) 0.0032(17) C661 0.0286(17) 0.030(2) 0.0282(18) 0.0005(16) 0.0112(14) 0.0046(15) Cl12 0.0458(5) 0.0318(5) 0.0457(6) 0.0012(4) 0.0135(4) 0.0123(4) Cl22 0.0320(5) 0.0553(7) 0.0508(6) 0.0086(5) -0.0027(4) 0.0041(5) N12 0.0370(16) 0.0226(15) 0.0260(15) 0.0000(13) 0.0086(12) -0.0014(13) N22 0.0456(18) 0.0208(14) 0.0192(15) 0.0030(13) 0.0093(13) -0.0055(14) C32 0.0316(19) 0.0250(18) 0.0290(19) -0.0003(15) 0.0123(15) 0.0025(15) N32 0.052(2) 0.0280(16) 0.0214(16) -0.0013(13) 0.0083(14) -0.0098(15) N42 0.0363(16) 0.0271(16) 0.0226(15) 0.0019(13) 0.0076(13) -0.0064(14) C52 0.0271(16) 0.0260(18) 0.0232(17) 0.0034(15) 0.0083(13) -0.0013(15) N52 0.0449(18) 0.0336(17) 0.0227(15) -0.0005(13) 0.0090(13) -0.0135(14) C62 0.0287(17) 0.0211(18) 0.0242(17) 0.0010(14) 0.0085(14) 0.0035(14) C612 0.0256(16) 0.0262(17) 0.0259(17) 0.0037(14) 0.0089(13) 0.0007(15) C622 0.0349(18) 0.0252(18) 0.0272(18) 0.0087(16) 0.0139(15) 0.0018(15) C632 0.0267(17) 0.041(2) 0.0300(19) 0.0067(17) 0.0059(15) -0.0006(16) C642 0.037(2) 0.036(2) 0.038(2) -0.0078(17) 0.0063(17) -0.0069(17) C652 0.039(2) 0.0285(19) 0.050(2) -0.0136(18) 0.0142(18) 0.0003(17) C662 0.031(2) 0.0254(19) 0.044(2) -0.0051(17) 0.0104(17) 0.0018(15) O13 0.0507(15) 0.0221(13) 0.0271(13) -0.0005(10) 0.0159(11) -0.0003(12) O23 0.0345(12) 0.0252(12) 0.0262(12) 0.0004(11) 0.0058(9) 0.0019(11) O33 0.078(2) 0.0234(13) 0.0216(12) -0.0017(11) 0.0140(12) -0.0082(13) O43 0.0551(17) 0.0214(14) 0.0307(14) -0.0006(10) 0.0201(12) 0.0004(11) O53 0.0442(14) 0.0450(15) 0.0405(14) -0.0014(11) 0.0162(11) -0.0035(11) C13 0.0299(17) 0.0255(19) 0.0229(17) -0.0024(16) 0.0057(13) -0.0020(15) C23 0.0314(18) 0.0303(18) 0.0230(17) 0.0023(14) 0.0065(14) 0.0019(14) C33 0.0303(17) 0.0355(19) 0.0250(18) -0.0054(15) 0.0096(14) 0.0003(15) C43 0.0245(16) 0.0253(19) 0.0236(17) -0.0028(15) 0.0053(13) -0.0070(15) S114 0.0363(6) 0.0659(8) 0.0330(5) -0.0070(6) 0.0099(4) -0.0068(6) C114 0.070(3) 0.078(4) 0.052(3) 0.008(3) 0.028(2) 0.012(3) C214 0.080(4) 0.068(3) 0.053(3) -0.015(3) 0.023(3) 0.004(3) S124 0.077(9) 0.079(10) 0.060(8) -0.010(7) 0.046(7) -0.029(8) C124 0.070(3) 0.078(4) 0.052(3) 0.008(3) 0.028(2) 0.012(3) C224 0.080(4) 0.068(3) 0.053(3) -0.015(3) 0.023(3) 0.004(3) O14 0.070(2) 0.072(2) 0.0331(16) -0.0119(17) 0.0172(14) -0.022(2) S115 0.0352(9) 0.0580(12) 0.0499(11) 0.0030(9) 0.0134(8) 0.0032(8) C115 0.087(4) 0.091(4) 0.055(3) -0.020(3) 0.036(3) -0.018(3) C215 0.084(4) 0.065(3) 0.074(4) 0.020(3) 0.010(3) -0.008(3) S125 0.0491(14) 0.0637(18) 0.0437(14) 0.0173(12) 0.0235(11) 0.0111(13) C125 0.087(4) 0.091(4) 0.055(3) -0.020(3) 0.036(3) -0.018(3) C225 0.084(4) 0.065(3) 0.074(4) 0.020(3) 0.010(3) -0.008(3) O15 0.088(2) 0.069(2) 0.0314(16) 0.0094(17) 0.0139(16) 0.018(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cl11 C661 1.729(4) . ? Cl21 C651 1.727(4) . ? N11 C61 1.281(4) . ? N11 N21 1.359(4) . ? N21 C31 1.349(5) . ? N21 H21 1.03(4) . ? C31 N31 1.311(5) . ? C31 N41 1.343(4) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N41 C51 1.343(5) . ? C51 N51 1.322(5) . ? C51 C61 1.461(5) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C61 C611 1.503(5) . ? C611 C621 1.377(5) . ? C611 C661 1.389(5) . ? C621 C631 1.393(6) . ? C621 H621 0.9500 . ? C631 C641 1.367(6) . ? C631 H631 0.9500 . ? C641 C651 1.379(6) . ? C641 H641 0.9500 . ? C651 C661 1.394(5) . ? Cl12 C622 1.735(4) . ? Cl22 C632 1.735(4) . ? N12 C62 1.307(4) . ? N12 N22 1.349(4) . ? N22 C32 1.350(5) . ? N22 H22 0.71(4) . ? C32 N42 1.329(4) . ? C32 N32 1.331(5) . ? N32 H32A 0.8800 . ? N32 H32B 0.8800 . ? N42 C52 1.329(4) . ? C52 N52 1.306(4) . ? C52 C62 1.453(5) . ? N52 H52A 0.8800 . ? N52 H52B 0.8800 . ? C62 C612 1.479(5) . ? C612 C622 1.394(5) . ? C612 C662 1.399(5) . ? C622 C632 1.391(5) . ? C632 C642 1.383(6) . ? C642 C652 1.387(5) . ? C642 H642 0.9500 . ? C652 C662 1.383(5) . ? C652 H652 0.9500 . ? C662 H662 0.9500 . ? O13 C43 1.262(5) . ? O23 C43 1.252(4) . ? O33 C13 1.256(4) . ? O43 C13 1.245(5) . ? O53 C23 1.385(4) . ? O53 H53 0.8400 . ? C13 C23 1.532(5) . ? C23 C33 1.524(4) . ? C23 H23 1.0000 . ? C33 C43 1.526(5) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? S114 O14 1.497(3) . ? S114 C114 1.779(5) . ? S114 C214 1.780(6) . ? C114 H11A 0.9800 . ? C114 H11B 0.9800 . ? C114 H11C 0.9800 . ? C214 H21A 0.9800 . ? C214 H21B 0.9800 . ? C214 H21C 0.9800 . ? S124 O14 1.472(15) . ? S115 O15 1.485(4) . ? S115 C215 1.738(6) . ? S115 C115 1.769(6) . ? C115 H11D 0.9800 . ? C115 H11E 0.9800 . ? C115 H11F 0.9800 . ? C215 H21D 0.9800 . ? C215 H21E 0.9800 . ? C215 H21F 0.9800 . ? S125 O15 1.492(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 C61 N11 N21 117.5(3) . . ? C31 N21 N11 122.3(3) . . ? C31 N21 H21 122(2) . . ? N11 N21 H21 113(2) . . ? N31 C31 N41 119.6(3) . . ? N31 C31 N21 118.6(3) . . ? N41 C31 N21 121.7(3) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C51 N41 C31 117.2(3) . . ? N51 C51 N41 118.9(3) . . ? N51 C51 C61 121.8(3) . . ? N41 C51 C61 119.3(3) . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? N11 C61 C51 121.2(3) . . ? N11 C61 C611 117.1(3) . . ? C51 C61 C611 121.7(3) . . ? C621 C611 C661 119.2(3) . . ? C621 C611 C61 119.8(3) . . ? C661 C611 C61 121.1(3) . . ? C611 C621 C631 120.7(3) . . ? C611 C621 H621 119.6 . . ? C631 C621 H621 119.6 . . ? C641 C631 C621 120.2(4) . . ? C641 C631 H631 119.9 . . ? C621 C631 H631 119.9 . . ? C631 C641 C651 119.7(4) . . ? C631 C641 H641 120.2 . . ? C651 C641 H641 120.2 . . ? C641 C651 C661 120.6(3) . . ? C641 C651 Cl21 119.0(3) . . ? C661 C651 Cl21 120.4(3) . . ? C611 C661 C651 119.7(3) . . ? C611 C661 Cl11 119.6(3) . . ? C651 C661 Cl11 120.8(3) . . ? C62 N12 N22 116.3(3) . . ? N12 N22 C32 123.2(3) . . ? N12 N22 H22 116(3) . . ? C32 N22 H22 120(3) . . ? N42 C32 N32 120.8(3) . . ? N42 C32 N22 121.5(3) . . ? N32 C32 N22 117.7(3) . . ? C32 N32 H32A 120.0 . . ? C32 N32 H32B 120.0 . . ? H32A N32 H32B 120.0 . . ? C52 N42 C32 117.5(3) . . ? N52 C52 N42 119.2(3) . . ? N52 C52 C62 120.9(3) . . ? N42 C52 C62 119.9(3) . . ? C52 N52 H52A 120.0 . . ? C52 N52 H52B 120.0 . . ? H52A N52 H52B 120.0 . . ? N12 C62 C52 120.8(3) . . ? N12 C62 C612 116.9(3) . . ? C52 C62 C612 122.3(3) . . ? C622 C612 C662 119.1(4) . . ? C622 C612 C62 121.2(3) . . ? C662 C612 C62 119.8(3) . . ? C632 C622 C612 120.1(3) . . ? C632 C622 Cl12 120.5(3) . . ? C612 C622 Cl12 119.5(3) . . ? C642 C632 C622 120.6(3) . . ? C642 C632 Cl22 118.8(3) . . ? C622 C632 Cl22 120.6(3) . . ? C632 C642 C652 119.4(4) . . ? C632 C642 H642 120.3 . . ? C652 C642 H642 120.3 . . ? C662 C652 C642 120.7(4) . . ? C662 C652 H652 119.7 . . ? C642 C652 H652 119.7 . . ? C652 C662 C612 120.2(4) . . ? C652 C662 H662 119.9 . . ? C612 C662 H662 119.9 . . ? C23 O53 H53 109.5 . . ? O43 C13 O33 124.9(3) . . ? O43 C13 C23 118.4(3) . . ? O33 C13 C23 116.6(3) . . ? O53 C23 C33 113.5(3) . . ? O53 C23 C13 112.6(3) . . ? C33 C23 C13 109.9(2) . . ? O53 C23 H23 106.8 . . ? C33 C23 H23 106.8 . . ? C13 C23 H23 106.8 . . ? C23 C33 C43 109.8(2) . . ? C23 C33 H33A 109.7 . . ? C43 C33 H33A 109.7 . . ? C23 C33 H33B 109.7 . . ? C43 C33 H33B 109.7 . . ? H33A C33 H33B 108.2 . . ? O23 C43 O13 124.8(3) . . ? O23 C43 C33 117.6(3) . . ? O13 C43 C33 117.6(3) . . ? O14 S114 C114 104.9(2) . . ? O14 S114 C214 105.9(2) . . ? C114 S114 C214 97.9(3) . . ? S114 C114 H11A 109.5 . . ? S114 C114 H11B 109.5 . . ? H11A C114 H11B 109.5 . . ? S114 C114 H11C 109.5 . . ? H11A C114 H11C 109.5 . . ? H11B C114 H11C 109.5 . . ? S114 C214 H21A 109.5 . . ? S114 C214 H21B 109.5 . . ? H21A C214 H21B 109.5 . . ? S114 C214 H21C 109.5 . . ? H21A C214 H21C 109.5 . . ? H21B C214 H21C 109.5 . . ? S124 O14 S114 49.7(5) . . ? O15 S115 C215 109.6(3) . . ? O15 S115 C115 106.4(3) . . ? C215 S115 C115 99.8(3) . . ? S115 C115 H11D 109.5 . . ? S115 C115 H11E 109.5 . . ? H11D C115 H11E 109.5 . . ? S115 C115 H11F 109.5 . . ? H11D C115 H11F 109.5 . . ? H11E C115 H11F 109.5 . . ? S115 C215 H21D 109.5 . . ? S115 C215 H21E 109.5 . . ? H21D C215 H21E 109.5 . . ? S115 C215 H21F 109.5 . . ? H21D C215 H21F 109.5 . . ? H21E C215 H21F 109.5 . . ? S115 O15 S125 49.45(16) . . ? 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 C61 N11 N21 C31 -5.6(5) . . . . ? N11 N21 C31 N31 -171.9(3) . . . . ? N11 N21 C31 N41 9.5(5) . . . . ? N31 C31 N41 C51 177.3(3) . . . . ? N21 C31 N41 C51 -4.2(5) . . . . ? C31 N41 C51 N51 175.5(3) . . . . ? C31 N41 C51 C61 -3.9(5) . . . . ? N21 N11 C61 C51 -2.8(5) . . . . ? N21 N11 C61 C611 179.2(3) . . . . ? N51 C51 C61 N11 -171.7(4) . . . . ? N41 C51 C61 N11 7.7(5) . . . . ? N51 C51 C61 C611 6.2(5) . . . . ? N41 C51 C61 C611 -174.3(3) . . . . ? N11 C61 C611 C621 70.9(4) . . . . ? C51 C61 C611 C621 -107.2(4) . . . . ? N11 C61 C611 C661 -109.4(4) . . . . ? C51 C61 C611 C661 72.5(4) . . . . ? C661 C611 C621 C631 0.9(6) . . . . ? C61 C611 C621 C631 -179.4(4) . . . . ? C611 C621 C631 C641 -0.5(7) . . . . ? C621 C631 C641 C651 0.1(7) . . . . ? C631 C641 C651 C661 -0.2(6) . . . . ? C631 C641 C651 Cl21 -179.8(3) . . . . ? C621 C611 C661 C651 -1.0(5) . . . . ? C61 C611 C661 C651 179.3(3) . . . . ? C621 C611 C661 Cl11 179.8(3) . . . . ? C61 C611 C661 Cl11 0.1(5) . . . . ? C641 C651 C661 C611 0.7(6) . . . . ? Cl21 C651 C661 C611 -179.8(3) . . . . ? C641 C651 C661 Cl11 179.9(3) . . . . ? Cl21 C651 C661 Cl11 -0.6(4) . . . . ? C62 N12 N22 C32 5.2(5) . . . . ? N12 N22 C32 N42 -10.2(5) . . . . ? N12 N22 C32 N32 170.7(3) . . . . ? N32 C32 N42 C52 -175.7(3) . . . . ? N22 C32 N42 C52 5.2(5) . . . . ? C32 N42 C52 N52 -175.4(3) . . . . ? C32 N42 C52 C62 3.5(5) . . . . ? N22 N12 C62 C52 3.7(5) . . . . ? N22 N12 C62 C612 -178.1(3) . . . . ? N52 C52 C62 N12 170.6(3) . . . . ? N42 C52 C62 N12 -8.3(5) . . . . ? N52 C52 C62 C612 -7.4(5) . . . . ? N42 C52 C62 C612 173.7(3) . . . . ? N12 C62 C612 C622 107.6(4) . . . . ? C52 C62 C612 C622 -74.3(4) . . . . ? N12 C62 C612 C662 -72.2(4) . . . . ? C52 C62 C612 C662 105.9(4) . . . . ? C662 C612 C622 C632 -0.6(5) . . . . ? C62 C612 C622 C632 179.5(3) . . . . ? C662 C612 C622 Cl12 179.5(3) . . . . ? C62 C612 C622 Cl12 -0.4(4) . . . . ? C612 C622 C632 C642 0.0(5) . . . . ? Cl12 C622 C632 C642 179.9(3) . . . . ? C612 C622 C632 Cl22 179.9(3) . . . . ? Cl12 C622 C632 Cl22 -0.2(4) . . . . ? C622 C632 C642 C652 -0.2(6) . . . . ? Cl22 C632 C642 C652 180.0(3) . . . . ? C632 C642 C652 C662 1.0(6) . . . . ? C642 C652 C662 C612 -1.6(6) . . . . ? C622 C612 C662 C652 1.4(5) . . . . ? C62 C612 C662 C652 -178.8(4) . . . . ? O43 C13 C23 O53 47.3(4) . . . . ? O33 C13 C23 O53 -132.2(3) . . . . ? O43 C13 C23 C33 -80.2(4) . . . . ? O33 C13 C23 C33 100.2(4) . . . . ? O53 C23 C33 C43 47.9(4) . . . . ? C13 C23 C33 C43 175.0(4) . . . . ? C23 C33 C43 O23 -107.6(3) . . . . ? C23 C33 C43 O13 72.3(4) . . . . ? C114 S114 O14 S124 57.8(9) . . . . ? C214 S114 O14 S124 -45.2(9) . . . . ? C215 S115 O15 S125 54.5(3) . . . . ? C115 S115 O15 S125 -52.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N22 H22 O33 0.71(4) 1.97(4) 2.680(4) 179(4) 2_646 N31 H31B O13 0.88 1.93 2.784(4) 161.9 2_645 N51 H51B O15 0.88 1.96 2.798(4) 159.8 2_646 N32 H32A O33 0.88 1.94 2.809(4) 167.6 . N32 H32B O43 0.88 2.01 2.849(4) 159.0 2_646 N52 H52A O13 0.88 1.99 2.865(4) 177.5 . N52 H52B O14 0.88 1.96 2.798(4) 157.8 1_554 O53 H53 N41 0.84 2.06 2.869(4) 160.6 1_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.633 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.081 # Attachment 'LM+8.(ACON).cif' data_LM+8.(ACON) _database_code_depnum_ccdc_archive 'CCDC 856211' #TrackingRef 'LM+8.(ACON).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - mesaconic acid - acetone - nitromethane (1:0.5:0.5:0.5) ; _chemical_name_common ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - mesaconic acid -acetone - nitromethane (1:0.5:0.5:0.5) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C4 H9 N O3, C5 H4 O4' _chemical_formula_sum 'C27 H29 Cl4 N11 O7' _chemical_formula_weight 761.41 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.6172(2) _cell_length_b 10.9788(2) _cell_length_c 15.9940(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.1290(10) _cell_angle_gamma 90.00 _cell_volume 1761.38(6) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7978 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 29.13 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.392 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.940 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 11790 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 29.11 _reflns_number_total 4653 _reflns_number_gt 3989 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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^)+(0.0527P)^2^+1.5700P] 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 4653 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1445 _refine_ls_wR_factor_gt 0.1370 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 Cl11 Cl 0.47504(6) 0.55930(5) 0.09666(4) 0.05018(17) Uani 1 1 d . . . Cl21 Cl 0.64293(7) 0.36960(9) 0.23742(5) 0.0754(3) Uani 1 1 d . . . N11 N 0.17273(16) 0.45013(14) -0.09582(10) 0.0300(3) Uani 1 1 d . . . N21 N 0.10302(17) 0.53257(14) -0.15581(9) 0.0321(3) Uani 1 1 d . . . H21 H 0.0781 0.5133 -0.2123 0.039 Uiso 1 1 calc R . . C31 C 0.0699(2) 0.64339(17) -0.13281(12) 0.0346(4) Uani 1 1 d . . . N31 N 0.0196(2) 0.72485(16) -0.19517(11) 0.0452(5) Uani 1 1 d . . . H31A H -0.0037 0.7971 -0.1814 0.054 Uiso 1 1 calc R . . H31B H 0.0093 0.7071 -0.2507 0.054 Uiso 1 1 calc R . . N41 N 0.0854(2) 0.67082(16) -0.04810(10) 0.0413(4) Uani 1 1 d . . . C51 C 0.1459(2) 0.58875(18) 0.01255(12) 0.0337(4) Uani 1 1 d . . . N51 N 0.15485(19) 0.61024(16) 0.09581(10) 0.0391(4) Uani 1 1 d . . . H51B H 0.1211 0.6775 0.1096 0.047 Uiso 1 1 calc R . . H51A H 0.1945 0.5572 0.1374 0.047 Uiso 1 1 calc R . . C61 C 0.19837(18) 0.47699(16) -0.01276(11) 0.0292(3) Uani 1 1 d . . . C611 C 0.27895(18) 0.38924(17) 0.05385(11) 0.0289(3) Uani 1 1 d . . . C621 C 0.40816(19) 0.41957(18) 0.10792(12) 0.0336(4) Uani 1 1 d . . . C631 C 0.4826(2) 0.3362(2) 0.17028(14) 0.0450(5) Uani 1 1 d . . . C641 C 0.4293(3) 0.2244(3) 0.17944(17) 0.0556(6) Uani 1 1 d . . . H641 H 0.4806 0.1675 0.2218 0.067 Uiso 1 1 calc R . . C651 C 0.3023(3) 0.1954(2) 0.12733(18) 0.0558(6) Uani 1 1 d . . . H651 H 0.2653 0.1190 0.1347 0.067 Uiso 1 1 calc R . . C661 C 0.2272(2) 0.27637(19) 0.06402(14) 0.0403(5) Uani 1 1 d . . . H661 H 0.1399 0.2544 0.0275 0.048 Uiso 1 1 calc R . . O12 O 0.96016(18) 0.52555(13) 0.32843(9) 0.0440(4) Uani 1 1 d . . . O22 O 0.94838(16) 0.33047(12) 0.35937(9) 0.0380(3) Uani 1 1 d . . . C12 C 0.9563(2) 0.44024(17) 0.37966(11) 0.0335(4) Uani 1 1 d . . . C212 C 0.9537(3) 0.4684(2) 0.47178(14) 0.0558(7) Uani 0.50 1 d P . 1 C32 C 0.8088(4) 0.4209(4) 0.4872(3) 0.0399(9) Uani 0.50 1 d P A 1 H32A H 0.7551 0.3750 0.4352 0.060 Uiso 0.50 1 calc PR A 1 H32B H 0.7584 0.4920 0.4956 0.060 Uiso 0.50 1 calc PR A 1 H32C H 0.8303 0.3687 0.5397 0.060 Uiso 0.50 1 calc PR A 1 C222 C 0.9537(3) 0.4684(2) 0.47178(14) 0.0558(7) Uani 0.50 1 d P . 2 H222 H 0.8817 0.4388 0.4888 0.067 Uiso 0.50 1 calc PR . 2 O113 O 0.7263(4) 0.9857(4) 0.23767(18) 0.1408(15) Uani 0.50 1 d P B 1 C113 C 0.6830(4) 0.9505(4) 0.1660(2) 0.0993(13) Uani 0.50 1 d P B 1 C213 C 0.6951(5) 0.8288(4) 0.1349(3) 0.1054(14) Uani 0.50 1 d P B 1 H21A H 0.6991 0.7699 0.1817 0.158 Uiso 0.50 1 calc PR B 1 H21B H 0.7768 0.8231 0.1192 0.158 Uiso 0.50 1 calc PR B 1 H21C H 0.6178 0.8110 0.0827 0.158 Uiso 0.50 1 calc PR B 1 C313 C 0.6772(9) 1.0659(8) 0.0903(5) 0.086(2) Uani 0.50 1 d P B 1 H31F H 0.6681 1.1448 0.1164 0.129 Uiso 0.50 1 calc PR B 1 H31D H 0.6006 1.0529 0.0366 0.129 Uiso 0.50 1 calc PR B 1 H31E H 0.7594 1.0651 0.0752 0.129 Uiso 0.50 1 calc PR B 1 O123 O 0.7263(4) 0.9857(4) 0.23767(18) 0.1408(15) Uani 0.50 1 d P C 2 N123 N 0.6830(4) 0.9505(4) 0.1660(2) 0.0993(13) Uani 0.50 1 d P C 2 C223 C 0.6951(5) 0.8288(4) 0.1349(3) 0.1054(14) Uani 0.50 1 d P C 2 H22A H 0.6999 0.7699 0.1819 0.158 Uiso 0.50 1 calc PR C 2 H22B H 0.7763 0.8233 0.1187 0.158 Uiso 0.50 1 calc PR C 2 H22C H 0.6174 0.8107 0.0830 0.158 Uiso 0.50 1 calc PR C 2 O223 O 0.5697(14) 0.9770(16) 0.1255(11) 0.303(10) Uani 0.50 1 d P C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl11 0.0554(3) 0.0469(3) 0.0512(3) -0.0147(2) 0.0215(3) -0.0213(2) Cl21 0.0388(3) 0.1123(7) 0.0567(4) -0.0060(4) -0.0095(3) -0.0024(4) N11 0.0398(8) 0.0264(7) 0.0239(7) -0.0014(5) 0.0107(6) 0.0010(6) N21 0.0500(9) 0.0278(7) 0.0180(6) -0.0019(5) 0.0104(6) 0.0039(6) C31 0.0513(11) 0.0301(9) 0.0227(8) -0.0014(7) 0.0126(7) 0.0069(8) N31 0.0803(14) 0.0323(9) 0.0237(7) 0.0020(6) 0.0180(8) 0.0176(9) N41 0.0662(12) 0.0361(9) 0.0217(7) -0.0008(6) 0.0144(7) 0.0179(8) C51 0.0464(10) 0.0328(9) 0.0219(8) -0.0026(7) 0.0111(7) 0.0049(8) N51 0.0579(11) 0.0380(9) 0.0213(7) -0.0009(6) 0.0130(7) 0.0125(8) C61 0.0364(9) 0.0276(8) 0.0235(8) -0.0015(6) 0.0096(7) 0.0013(7) C611 0.0321(8) 0.0308(8) 0.0232(7) -0.0009(6) 0.0084(6) 0.0010(7) C621 0.0346(9) 0.0391(10) 0.0279(8) -0.0053(7) 0.0111(7) -0.0049(7) C631 0.0327(10) 0.0647(14) 0.0320(10) 0.0005(9) 0.0028(8) 0.0015(9) C641 0.0488(13) 0.0646(16) 0.0462(13) 0.0251(12) 0.0060(10) 0.0092(11) C651 0.0497(13) 0.0479(13) 0.0640(16) 0.0257(12) 0.0110(11) -0.0009(10) C661 0.0349(10) 0.0385(10) 0.0430(11) 0.0075(8) 0.0065(8) -0.0031(8) O12 0.0808(11) 0.0264(6) 0.0229(6) -0.0020(5) 0.0143(7) -0.0076(7) O22 0.0640(9) 0.0280(6) 0.0252(6) 0.0006(5) 0.0191(6) -0.0028(6) C12 0.0492(11) 0.0308(9) 0.0172(7) -0.0002(6) 0.0065(7) 0.0037(8) C212 0.110(2) 0.0327(10) 0.0250(9) 0.0008(8) 0.0221(11) 0.0109(12) C32 0.037(2) 0.040(2) 0.043(2) 0.0078(17) 0.0133(17) 0.0021(16) C222 0.110(2) 0.0327(10) 0.0250(9) 0.0008(8) 0.0221(11) 0.0109(12) O113 0.210(4) 0.165(3) 0.0575(15) -0.0536(18) 0.057(2) -0.094(3) C113 0.083(2) 0.153(4) 0.0623(18) -0.043(2) 0.0247(16) 0.023(2) C213 0.143(4) 0.100(3) 0.076(2) -0.024(2) 0.040(3) -0.035(3) C313 0.090(5) 0.095(5) 0.082(5) 0.008(4) 0.040(4) -0.008(4) O123 0.210(4) 0.165(3) 0.0575(15) -0.0536(18) 0.057(2) -0.094(3) N123 0.083(2) 0.153(4) 0.0623(18) -0.043(2) 0.0247(16) 0.023(2) C223 0.143(4) 0.100(3) 0.076(2) -0.024(2) 0.040(3) -0.035(3) O223 0.197(12) 0.40(2) 0.283(16) -0.052(15) 0.043(11) 0.196(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl11 C621 1.724(2) . ? Cl21 C631 1.729(2) . ? N11 C61 1.299(2) . ? N11 N21 1.350(2) . ? N21 C31 1.351(2) . ? N21 H21 0.8800 . ? C31 N31 1.315(2) . ? C31 N41 1.344(2) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N41 C51 1.326(2) . ? C51 N51 1.325(2) . ? C51 C61 1.459(2) . ? N51 H51B 0.8800 . ? N51 H51A 0.8800 . ? C61 C611 1.482(2) . ? C611 C661 1.387(3) . ? C611 C621 1.401(3) . ? C621 C631 1.393(3) . ? C631 C641 1.380(4) . ? C641 C651 1.370(4) . ? C641 H641 0.9500 . ? C651 C661 1.386(3) . ? C651 H651 0.9500 . ? C661 H661 0.9500 . ? O12 C12 1.254(2) . ? O22 C12 1.244(2) . ? C12 C212 1.514(3) . ? C212 C212 1.296(6) 3_766 ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? O113 C113 1.153(4) . ? C113 C213 1.446(6) . ? C213 H21A 0.9800 . ? C213 H21B 0.9800 . ? C213 H21C 0.9800 . ? C313 H31F 0.9800 . ? C313 H31D 0.9800 . ? C313 H31E 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C61 N11 N21 117.19(15) . . ? N11 N21 C31 122.78(15) . . ? N11 N21 H21 118.6 . . ? C31 N21 H21 118.6 . . ? N31 C31 N41 119.82(17) . . ? N31 C31 N21 118.88(16) . . ? N41 C31 N21 121.29(17) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C51 N41 C31 117.09(16) . . ? N51 C51 N41 118.20(17) . . ? N51 C51 C61 121.38(17) . . ? N41 C51 C61 120.41(16) . . ? C51 N51 H51B 120.0 . . ? C51 N51 H51A 120.0 . . ? H51B N51 H51A 120.0 . . ? N11 C61 C51 120.23(16) . . ? N11 C61 C611 117.74(16) . . ? C51 C61 C611 122.01(15) . . ? C661 C611 C621 119.05(17) . . ? C661 C611 C61 120.49(17) . . ? C621 C611 C61 120.45(17) . . ? C631 C621 C611 119.78(19) . . ? C631 C621 Cl11 120.19(16) . . ? C611 C621 Cl11 120.02(15) . . ? C641 C631 C621 120.3(2) . . ? C641 C631 Cl21 118.50(18) . . ? C621 C631 Cl21 121.17(19) . . ? C651 C641 C631 119.8(2) . . ? C651 C641 H641 120.1 . . ? C631 C641 H641 120.1 . . ? C641 C651 C661 120.8(2) . . ? C641 C651 H651 119.6 . . ? C661 C651 H651 119.6 . . ? C651 C661 C611 120.2(2) . . ? C651 C661 H661 119.9 . . ? C611 C661 H661 119.9 . . ? O22 C12 O12 124.55(16) . . ? O22 C12 C212 115.51(17) . . ? O12 C12 C212 119.86(17) . . ? C212 C212 C12 122.4(3) 3_766 . ? C212 C212 C32 124.9(3) 3_766 . ? C12 C212 C32 112.4(2) . . ? C212 C32 H32A 109.5 . . ? C212 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C212 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O113 C113 C213 126.9(5) . . ? O113 C113 C313 111.1(5) . . ? C213 C113 C313 114.8(4) . . ? C113 C213 H21A 109.5 . . ? C113 C213 H21B 109.5 . . ? H21A C213 H21B 109.5 . . ? C113 C213 H21C 109.5 . . ? H21A C213 H21C 109.5 . . ? H21B C213 H21C 109.5 . . ? C113 C313 H31F 109.5 . . ? C113 C313 H31D 109.5 . . ? H31F C313 H31D 109.5 . . ? C113 C313 H31E 109.5 . . ? H31F C313 H31E 109.5 . . ? H31D C313 H31E 109.5 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 29.11 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.729 _refine_diff_density_min -0.590 _refine_diff_density_rms 0.055 # Attachment 'LM+9.(DMSO).cif' data_LM+9.(DMSO) _database_code_depnum_ccdc_archive 'CCDC 856212' #TrackingRef 'LM+9.(DMSO).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - D,L-chlorosuccinate - dimethyl sulfoxide (1:0.5:1) ; _chemical_name_common ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - D,L- chlorosuccinate -dimethyl sulfoxide (1:0.5:1) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), 2(C2 H6 O S), C4 H3 Cl O4' _chemical_formula_sum 'C26 H31 Cl5 N10 O6 S2' _chemical_formula_weight 820.98 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0489(3) _cell_length_b 10.8220(4) _cell_length_c 16.2310(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.403(2) _cell_angle_gamma 90.00 _cell_volume 1830.53(12) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 17231 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 0.564 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 12846 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.52 _reflns_number_total 4173 _reflns_number_gt 2926 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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^ > 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^)+(0.0894P)^2^+5.0898P] 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 4173 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1300 _refine_ls_R_factor_gt 0.0939 _refine_ls_wR_factor_ref 0.2731 _refine_ls_wR_factor_gt 0.2467 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _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 Cl11 Cl 0.46473(15) 0.09494(14) 0.08387(11) 0.0656(5) Uani 1 1 d . . . Cl21 Cl 0.64396(16) -0.0751(2) 0.23187(12) 0.0854(6) Uani 1 1 d . . . N11 N 0.1802(4) -0.0396(4) -0.0929(3) 0.0447(10) Uani 1 1 d . . . N21 N 0.1042(4) 0.0340(3) -0.1556(3) 0.0437(9) Uani 1 1 d . . . H21 H 0.0838 0.0100 -0.2103 0.052 Uiso 1 1 calc R . . C31 C 0.0575(5) 0.1431(4) -0.1387(3) 0.0386(10) Uani 1 1 d . . . N31 N -0.0016(5) 0.2162(4) -0.2042(3) 0.0535(11) Uani 1 1 d . . . H31A H -0.0330 0.2873 -0.1945 0.064 Uiso 1 1 calc R . . H31B H -0.0099 0.1940 -0.2580 0.064 Uiso 1 1 calc R . . N41 N 0.0702(4) 0.1766(4) -0.0564(3) 0.0441(9) Uani 1 1 d . . . C51 C 0.1385(5) 0.1024(4) 0.0075(3) 0.0399(10) Uani 1 1 d . . . N51 N 0.1466(4) 0.1289(4) 0.0886(3) 0.0514(11) Uani 1 1 d . . . H51A H 0.1073 0.1945 0.0994 0.062 Uiso 1 1 calc R . . H51B H 0.1914 0.0810 0.1318 0.062 Uiso 1 1 calc R . . C61 C 0.2013(5) -0.0077(4) -0.0125(3) 0.0407(10) Uani 1 1 d . . . C611 C 0.2882(5) -0.0875(5) 0.0572(3) 0.0467(11) Uani 1 1 d . . . C621 C 0.4117(5) -0.0480(5) 0.1065(3) 0.0454(11) Uani 1 1 d . . . C631 C 0.4899(5) -0.1219(6) 0.1710(4) 0.0578(14) Uani 1 1 d . . . C641 C 0.4467(6) -0.2342(7) 0.1885(5) 0.0742(19) Uani 1 1 d . . . H641 H 0.5008 -0.2843 0.2339 0.089 Uiso 1 1 calc R . . C651 C 0.3243(6) -0.2756(6) 0.1405(5) 0.079(2) Uani 1 1 d . . . H651 H 0.2947 -0.3537 0.1527 0.095 Uiso 1 1 calc R . . C661 C 0.2459(6) -0.2008(5) 0.0746(5) 0.0645(16) Uani 1 1 d . . . H661 H 0.1623 -0.2283 0.0413 0.077 Uiso 1 1 calc R . . O12 O 0.0747(4) 0.5364(4) 0.1813(3) 0.0588(10) Uani 1 1 d . . . O22 O 0.0249(4) 0.3454(4) 0.1325(2) 0.0615(11) Uani 1 1 d . . . C112 C 0.0471(5) 0.4577(7) 0.1230(4) 0.0585(15) Uani 0.50 1 d P A 1 C212 C 0.0468(9) 0.4958(14) 0.0321(5) 0.136(5) Uani 0.50 1 d P . 1 H21A H 0.0894 0.5775 0.0394 0.163 Uiso 0.50 1 calc PR . 1 H21B H 0.1049 0.4372 0.0168 0.163 Uiso 0.50 1 calc PR . 1 Cl12 Cl 0.1991(4) 0.4744(5) 0.0289(3) 0.1022(15) Uani 0.50 1 d P B 2 C122 C 0.0471(5) 0.4577(7) 0.1230(4) 0.0585(15) Uani 0.50 1 d P A 2 C222 C 0.0468(9) 0.4958(14) 0.0321(5) 0.136(5) Uani 0.50 1 d P . 2 H222 H 0.0561 0.5864 0.0445 0.163 Uiso 0.50 1 calc PR . 2 S113 S 0.7450(3) 0.5064(3) 0.17770(18) 0.0722(7) Uani 0.65 1 d P C 1 C113 C 0.6622(15) 0.6060(13) 0.0913(7) 0.161(5) Uani 0.65 1 d P C 1 H11A H 0.6858 0.6918 0.1085 0.241 Uiso 0.65 1 calc PR C 1 H11B H 0.5695 0.5955 0.0778 0.241 Uiso 0.65 1 calc PR C 1 H11C H 0.6853 0.5861 0.0395 0.241 Uiso 0.65 1 calc PR C 1 C213 C 0.6861(9) 0.3631(9) 0.1305(6) 0.104(3) Uani 0.65 1 d P C 1 H21C H 0.7190 0.3458 0.0826 0.155 Uiso 0.65 1 calc PR C 1 H21D H 0.5921 0.3655 0.1078 0.155 Uiso 0.65 1 calc PR C 1 H21E H 0.7142 0.2980 0.1747 0.155 Uiso 0.65 1 calc PR C 1 S123 S 0.6392(8) 0.5001(7) 0.1554(5) 0.0957(19) Uani 0.35 1 d P C 2 C123 C 0.6622(15) 0.6060(13) 0.0913(7) 0.161(5) Uani 0.35 1 d P C 2 H12A H 0.5911 0.6653 0.0767 0.241 Uiso 0.35 1 calc PR C 2 H12B H 0.6663 0.5676 0.0376 0.241 Uiso 0.35 1 calc PR C 2 H12C H 0.7430 0.6491 0.1208 0.241 Uiso 0.35 1 calc PR C 2 C223 C 0.6861(9) 0.3631(9) 0.1305(6) 0.104(3) Uani 0.35 1 d P C 2 H22A H 0.7536 0.3747 0.1044 0.155 Uiso 0.35 1 calc PR C 2 H22B H 0.6128 0.3207 0.0887 0.155 Uiso 0.35 1 calc PR C 2 H22C H 0.7194 0.3132 0.1836 0.155 Uiso 0.35 1 calc PR C 2 O13 O 0.7002(6) 0.5335(6) 0.2491(3) 0.1056(19) 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 Cl11 0.0698(9) 0.0556(8) 0.0733(10) -0.0111(7) 0.0261(7) -0.0224(7) Cl21 0.0566(9) 0.1113(16) 0.0754(11) -0.0156(10) 0.0046(8) 0.0009(9) N11 0.054(2) 0.0290(19) 0.056(3) -0.0007(18) 0.025(2) 0.0024(17) N21 0.066(3) 0.0294(19) 0.038(2) -0.0078(16) 0.0210(19) 0.0012(17) C31 0.055(3) 0.028(2) 0.037(2) -0.0032(18) 0.021(2) -0.0034(19) N31 0.088(3) 0.039(2) 0.034(2) 0.0021(17) 0.022(2) 0.010(2) N41 0.062(3) 0.0318(19) 0.041(2) -0.0018(17) 0.0207(19) 0.0052(18) C51 0.048(3) 0.034(2) 0.040(2) -0.0036(19) 0.018(2) -0.0040(19) N51 0.069(3) 0.049(2) 0.040(2) -0.0013(19) 0.021(2) 0.009(2) C61 0.046(3) 0.030(2) 0.049(3) -0.002(2) 0.021(2) -0.0024(19) C611 0.046(3) 0.042(3) 0.056(3) 0.003(2) 0.023(2) 0.003(2) C621 0.049(3) 0.042(3) 0.049(3) -0.004(2) 0.020(2) -0.002(2) C631 0.043(3) 0.073(4) 0.056(3) -0.005(3) 0.016(2) -0.001(3) C641 0.064(4) 0.080(5) 0.077(4) 0.031(4) 0.022(3) 0.016(3) C651 0.067(4) 0.055(4) 0.113(6) 0.036(4) 0.027(4) 0.009(3) C661 0.051(3) 0.046(3) 0.094(5) 0.021(3) 0.021(3) 0.000(2) O12 0.087(3) 0.042(2) 0.054(2) 0.0166(18) 0.032(2) 0.0142(19) O22 0.081(3) 0.068(3) 0.045(2) -0.0128(19) 0.034(2) -0.007(2) C112 0.049(3) 0.086(5) 0.040(3) 0.019(3) 0.014(2) 0.004(3) C212 0.093(6) 0.256(14) 0.057(5) 0.060(7) 0.023(4) -0.008(8) Cl12 0.066(2) 0.171(5) 0.074(2) 0.005(3) 0.0290(17) -0.010(2) C122 0.049(3) 0.086(5) 0.040(3) 0.019(3) 0.014(2) 0.004(3) C222 0.093(6) 0.256(14) 0.057(5) 0.060(7) 0.023(4) -0.008(8) S113 0.0648(16) 0.091(2) 0.0659(16) -0.0095(14) 0.0286(12) -0.0158(14) C113 0.241(15) 0.142(11) 0.091(7) 0.036(7) 0.044(8) 0.005(10) C213 0.120(7) 0.103(7) 0.083(5) -0.018(5) 0.027(5) -0.023(5) S123 0.115(5) 0.099(4) 0.093(4) -0.021(4) 0.062(4) -0.021(4) C123 0.241(15) 0.142(11) 0.091(7) 0.036(7) 0.044(8) 0.005(10) C223 0.120(7) 0.103(7) 0.083(5) -0.018(5) 0.027(5) -0.023(5) O13 0.135(5) 0.116(5) 0.062(3) -0.017(3) 0.028(3) -0.034(4) _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 Cl11 C621 1.736(5) . ? Cl21 C631 1.736(6) . ? N11 C61 1.293(6) . ? N11 N21 1.345(6) . ? N21 C31 1.353(6) . ? N21 H21 0.8800 . ? C31 N31 1.313(6) . ? C31 N41 1.345(6) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N41 C51 1.330(6) . ? C51 N51 1.321(6) . ? C51 C61 1.468(6) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C61 C611 1.492(7) . ? C611 C661 1.374(7) . ? C611 C621 1.400(7) . ? C621 C631 1.372(8) . ? C631 C641 1.369(9) . ? C641 C651 1.391(10) . ? C641 H641 0.9500 . ? C651 C661 1.391(8) . ? C651 H651 0.9500 . ? C661 H661 0.9500 . ? O12 C112 1.234(8) . ? O22 C112 1.259(8) . ? C112 C212 1.532(9) . ? C212 C212 1.202(16) 3_565 ? C212 H21A 0.9900 . ? C212 H21B 0.9900 . ? S113 O13 1.434(6) . ? S113 C213 1.756(9) . ? S113 C113 1.765(11) . ? C113 H11A 0.9800 . ? C113 H11B 0.9800 . ? C113 H11C 0.9800 . ? C213 H21C 0.9800 . ? C213 H21D 0.9800 . ? C213 H21E 0.9800 . ? S123 O13 1.489(9) . ? 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 C61 N11 N21 117.6(4) . . ? N11 N21 C31 123.2(4) . . ? N11 N21 H21 118.4 . . ? C31 N21 H21 118.4 . . ? N31 C31 N41 120.2(4) . . ? N31 C31 N21 118.8(4) . . ? N41 C31 N21 121.0(4) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C51 N41 C31 117.2(4) . . ? N51 C51 N41 118.6(4) . . ? N51 C51 C61 121.1(4) . . ? N41 C51 C61 120.3(4) . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? N11 C61 C51 119.9(4) . . ? N11 C61 C611 117.7(4) . . ? C51 C61 C611 122.3(4) . . ? C661 C611 C621 119.3(5) . . ? C661 C611 C61 119.7(5) . . ? C621 C611 C61 121.0(4) . . ? C631 C621 C611 120.3(5) . . ? C631 C621 Cl11 120.7(4) . . ? C611 C621 Cl11 119.0(4) . . ? C641 C631 C621 120.1(5) . . ? C641 C631 Cl21 119.0(5) . . ? C621 C631 Cl21 120.9(5) . . ? C631 C641 C651 120.7(6) . . ? C631 C641 H641 119.6 . . ? C651 C641 H641 119.6 . . ? C661 C651 C641 119.0(6) . . ? C661 C651 H651 120.5 . . ? C641 C651 H651 120.5 . . ? C611 C661 C651 120.6(6) . . ? C611 C661 H661 119.7 . . ? C651 C661 H661 119.7 . . ? O12 C112 O22 125.6(5) . . ? O12 C112 C212 118.3(8) . . ? O22 C112 C212 116.0(8) . . ? C212 C212 C112 125.5(11) 3_565 . ? C212 C212 H21A 105.9 3_565 . ? C112 C212 H21A 105.9 . . ? C212 C212 H21B 105.9 3_565 . ? C112 C212 H21B 105.9 . . ? H21A C212 H21B 106.3 . . ? O13 S113 C213 110.8(4) . . ? O13 S113 C113 106.9(6) . . ? C213 S113 C113 100.0(6) . . ? S113 C113 H11A 109.5 . . ? S113 C113 H11B 109.5 . . ? H11A C113 H11B 109.5 . . ? S113 C113 H11C 109.5 . . ? H11A C113 H11C 109.5 . . ? H11B C113 H11C 109.5 . . ? S113 C213 H21C 109.5 . . ? S113 C213 H21D 109.5 . . ? H21C C213 H21D 109.5 . . ? S113 C213 H21E 109.5 . . ? H21C C213 H21E 109.5 . . ? H21D C213 H21E 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 C61 N11 N21 C31 5.1(7) . . . . ? N11 N21 C31 N31 171.1(4) . . . . ? N11 N21 C31 N41 -9.3(7) . . . . ? N31 C31 N41 C51 -175.6(4) . . . . ? N21 C31 N41 C51 4.8(7) . . . . ? C31 N41 C51 N51 -176.1(4) . . . . ? C31 N41 C51 C61 2.8(7) . . . . ? N21 N11 C61 C51 2.7(6) . . . . ? N21 N11 C61 C611 -178.5(4) . . . . ? N51 C51 C61 N11 172.1(5) . . . . ? N41 C51 C61 N11 -6.8(7) . . . . ? N51 C51 C61 C611 -6.6(7) . . . . ? N41 C51 C61 C611 174.5(4) . . . . ? N11 C61 C611 C661 -73.3(7) . . . . ? C51 C61 C611 C661 105.5(6) . . . . ? N11 C61 C611 C621 107.9(6) . . . . ? C51 C61 C611 C621 -73.4(6) . . . . ? C661 C611 C621 C631 0.4(8) . . . . ? C61 C611 C621 C631 179.3(5) . . . . ? C661 C611 C621 Cl11 179.8(4) . . . . ? C61 C611 C621 Cl11 -1.3(7) . . . . ? C611 C621 C631 C641 -1.0(9) . . . . ? Cl11 C621 C631 C641 179.6(5) . . . . ? C611 C621 C631 Cl21 179.3(4) . . . . ? Cl11 C621 C631 Cl21 -0.1(7) . . . . ? C621 C631 C641 C651 1.0(10) . . . . ? Cl21 C631 C641 C651 -179.3(6) . . . . ? C631 C641 C651 C661 -0.3(11) . . . . ? C621 C611 C661 C651 0.3(9) . . . . ? C61 C611 C661 C651 -178.6(6) . . . . ? C641 C651 C661 C611 -0.3(11) . . . . ? O12 C112 C212 C212 -111(2) . . . 3_565 ? O22 C112 C212 C212 72(2) . . . 3_565 ? C213 S113 O13 S123 -54.3(6) . . . . ? C113 S113 O13 S123 53.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.635 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.098 # Attachment '- LM+10.(ACON).cif' data_LM+10.(ACON) _database_code_depnum_ccdc_archive 'CCDC 856213' #TrackingRef '- LM+10.(ACON).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - D,L-Bromosuccinate - acetone (1:0.5:1) ; _chemical_name_common ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - D,L- Bromosuccinate -acetone (1:0.5:1) ; _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C4 H3 Br O4, 2(C3 H6 O)' _chemical_formula_sum 'C28 H31 Br Cl4 N10 O6' _chemical_formula_weight 825.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.7609(3) _cell_length_b 11.0390(4) _cell_length_c 16.0899(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.284(2) _cell_angle_gamma 90.00 _cell_volume 1825.00(11) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 12210 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 1.473 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.706 _exptl_absorpt_correction_T_max 0.774 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 10039 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 27.43 _reflns_number_total 4110 _reflns_number_gt 3257 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'Superflip (Palatinus, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (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^)+(0.0789P)^2^+4.0315P] 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 4110 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0798 _refine_ls_wR_factor_ref 0.2136 _refine_ls_wR_factor_gt 0.1996 _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 N11 N 0.3182(3) -0.0374(3) 0.0916(2) 0.0421(7) Uani 1 1 d . . . N21 N 0.3916(4) 0.0371(3) 0.1538(2) 0.0449(8) Uani 1 1 d . . . H21 H 0.4136 0.0127 0.2083 0.054 Uiso 1 1 calc R . . C31 C 0.4329(4) 0.1472(3) 0.1361(2) 0.0435(9) Uani 1 1 d . . . N31 N 0.4864(4) 0.2195(3) 0.2009(2) 0.0583(10) Uani 1 1 d . . . H31A H 0.5156 0.2908 0.1910 0.070 Uiso 1 1 calc R . . H31B H 0.4932 0.1969 0.2546 0.070 Uiso 1 1 calc R . . N41 N 0.4219(4) 0.1810(3) 0.05383(19) 0.0454(8) Uani 1 1 d . . . C51 C 0.3580(4) 0.1071(3) -0.0091(2) 0.0398(8) Uani 1 1 d . . . N51 N 0.3539(4) 0.1329(3) -0.08985(19) 0.0499(8) Uani 1 1 d . . . H51A H 0.3932 0.1981 -0.1010 0.060 Uiso 1 1 calc R . . H51B H 0.3119 0.0849 -0.1326 0.060 Uiso 1 1 calc R . . C61 C 0.2976(4) -0.0026(3) 0.0116(2) 0.0402(8) Uani 1 1 d . . . Cl11 Cl 0.03418(13) 0.09608(11) -0.08882(8) 0.0668(4) Uani 1 1 d . . . Cl21 Cl -0.13659(14) -0.07175(18) -0.23677(10) 0.0907(5) Uani 1 1 d . . . C611 C 0.2133(4) -0.0825(3) -0.0575(3) 0.0433(8) Uani 1 1 d . . . C621 C 0.0923(4) -0.0439(4) -0.1083(3) 0.0481(9) Uani 1 1 d . . . C631 C 0.0163(4) -0.1193(5) -0.1729(3) 0.0597(11) Uani 1 1 d . . . C641 C 0.0613(5) -0.2312(5) -0.1866(4) 0.0757(15) Uani 1 1 d . . . H641 H 0.0096 -0.2820 -0.2312 0.091 Uiso 1 1 calc R . . C651 C 0.1811(6) -0.2700(5) -0.1359(4) 0.0810(17) Uani 1 1 d . . . H651 H 0.2116 -0.3481 -0.1452 0.097 Uiso 1 1 calc R . . C661 C 0.2575(5) -0.1961(4) -0.0715(3) 0.0604(12) Uani 1 1 d . . . H661 H 0.3405 -0.2234 -0.0368 0.073 Uiso 1 1 calc R . . Br12 Br 0.28235(10) 0.04228(11) 0.48260(8) 0.0730(4) Uani 0.50 1 d P A 1 C212 C 0.4593(9) -0.0194(7) 0.4649(3) 0.107(3) Uani 0.50 1 d P . 1 H212 H 0.4609 -0.1099 0.4627 0.129 Uiso 0.50 1 calc PR . 1 C222 C 0.4593(9) -0.0194(7) 0.4649(3) 0.107(3) Uani 0.50 1 d P . 2 H22A H 0.3713 -0.0097 0.4716 0.129 Uiso 0.50 1 calc PR . 2 H22B H 0.4744 -0.1075 0.4617 0.129 Uiso 0.50 1 calc PR . 2 C12 C 0.4550(5) 0.0350(4) 0.3754(3) 0.0546(11) Uani 1 1 d . . . O12 O 0.4714(3) 0.1464(3) 0.36849(17) 0.0573(8) Uani 1 1 d . . . O22 O 0.4281(4) -0.0401(3) 0.31593(19) 0.0608(9) Uani 1 1 d . . . O113 O 0.2788(12) 0.5198(10) 0.2536(8) 0.089(3) Uani 0.50 1 d P B 1 C313 C 0.208(2) 0.654(3) 0.1446(19) 0.100(9) Uani 0.50 1 d P B 1 H31C H 0.2871 0.6956 0.1785 0.150 Uiso 0.50 1 calc PR B 1 H31D H 0.1318 0.7042 0.1430 0.150 Uiso 0.50 1 calc PR B 1 H31E H 0.2112 0.6404 0.0852 0.150 Uiso 0.50 1 calc PR B 1 C113 C 0.198(2) 0.545(2) 0.1827(14) 0.087(6) Uani 0.50 1 d P B 1 C213 C 0.099(3) 0.488(4) 0.1447(18) 0.24(2) Uani 0.50 1 d P B 1 H21A H 0.0965 0.4124 0.1756 0.367 Uiso 0.50 1 calc PR B 1 H21B H 0.0991 0.4707 0.0851 0.367 Uiso 0.50 1 calc PR B 1 H21C H 0.0218 0.5370 0.1432 0.367 Uiso 0.50 1 calc PR B 1 O123 O 0.2161(15) 0.4605(14) 0.2363(7) 0.111(4) Uani 0.50 1 d P C 2 C123 C 0.201(2) 0.488(2) 0.1621(12) 0.084(6) Uani 0.50 1 d P C 2 C223 C 0.1694(16) 0.3943(13) 0.0975(9) 0.096(4) Uani 0.50 1 d P C 2 H22C H 0.1885 0.3151 0.1259 0.145 Uiso 0.50 1 calc PR C 2 H22D H 0.2217 0.4050 0.0574 0.145 Uiso 0.50 1 calc PR C 2 H22E H 0.0768 0.3988 0.0649 0.145 Uiso 0.50 1 calc PR C 2 C323 C 0.172(4) 0.622(5) 0.130(3) 0.18(2) Uani 0.50 1 d P C 2 H32A H 0.1982 0.6765 0.1805 0.269 Uiso 0.50 1 calc PR C 2 H32B H 0.0787 0.6312 0.1010 0.269 Uiso 0.50 1 calc PR C 2 H32C H 0.2212 0.6412 0.0897 0.269 Uiso 0.50 1 calc PR C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0557(19) 0.0317(15) 0.0404(16) 0.0038(12) 0.0165(14) 0.0021(13) N21 0.073(2) 0.0323(15) 0.0310(14) 0.0081(12) 0.0177(15) 0.0032(14) C31 0.072(3) 0.0332(17) 0.0301(16) 0.0043(14) 0.0217(17) 0.0019(17) N31 0.107(3) 0.0384(17) 0.0305(15) 0.0002(13) 0.0214(18) -0.0095(18) N41 0.072(2) 0.0357(15) 0.0301(14) 0.0018(12) 0.0176(14) -0.0068(15) C51 0.056(2) 0.0346(17) 0.0327(16) 0.0029(14) 0.0195(15) 0.0033(15) N51 0.072(2) 0.0496(19) 0.0299(15) 0.0004(14) 0.0183(15) -0.0114(17) C61 0.050(2) 0.0316(16) 0.0416(18) 0.0012(14) 0.0179(16) 0.0034(15) Cl11 0.0717(8) 0.0598(7) 0.0703(7) 0.0125(6) 0.0234(6) 0.0261(6) Cl21 0.0579(7) 0.1246(13) 0.0744(9) 0.0164(8) -0.0038(6) 0.0004(8) C611 0.045(2) 0.0391(19) 0.047(2) -0.0022(16) 0.0153(16) 0.0005(15) C621 0.052(2) 0.050(2) 0.045(2) 0.0056(17) 0.0202(18) 0.0068(18) C631 0.049(2) 0.076(3) 0.050(2) 0.002(2) 0.0088(19) -0.002(2) C641 0.069(3) 0.080(4) 0.071(3) -0.025(3) 0.009(3) -0.017(3) C651 0.074(3) 0.061(3) 0.101(4) -0.036(3) 0.016(3) -0.004(3) C661 0.053(2) 0.044(2) 0.078(3) -0.013(2) 0.011(2) 0.0026(19) Br12 0.0579(6) 0.0832(7) 0.0801(7) 0.0038(6) 0.0238(5) -0.0040(5) C212 0.166(7) 0.107(5) 0.042(3) 0.014(3) 0.020(4) -0.022(5) C222 0.166(7) 0.107(5) 0.042(3) 0.014(3) 0.020(4) -0.022(5) C12 0.063(3) 0.065(3) 0.037(2) 0.019(2) 0.0165(18) 0.008(2) O12 0.079(2) 0.0640(19) 0.0336(13) -0.0109(13) 0.0237(14) 0.0013(16) O22 0.099(3) 0.0438(16) 0.0430(15) 0.0136(13) 0.0263(16) 0.0144(15) O113 0.111(9) 0.084(7) 0.076(7) 0.024(6) 0.033(6) 0.026(6) C313 0.074(8) 0.15(2) 0.081(14) 0.060(15) 0.035(8) 0.054(11) C113 0.093(12) 0.120(17) 0.066(10) 0.012(11) 0.051(8) 0.014(12) C213 0.22(3) 0.40(5) 0.16(2) -0.09(3) 0.13(2) -0.22(3) O123 0.141(12) 0.143(12) 0.044(5) 0.017(6) 0.022(6) 0.023(8) C123 0.077(9) 0.124(16) 0.063(10) 0.034(10) 0.039(8) 0.045(12) C223 0.121(11) 0.098(9) 0.085(8) -0.007(8) 0.052(8) 0.009(8) C323 0.25(5) 0.20(4) 0.083(16) 0.012(19) 0.05(2) 0.08(4) _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 N11 C61 1.298(5) . ? N11 N21 1.353(4) . ? N21 C31 1.353(5) . ? N21 H21 0.8800 . ? C31 N31 1.303(5) . ? C31 N41 1.347(4) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N41 C51 1.323(5) . ? C51 N51 1.318(4) . ? C51 C61 1.459(5) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C61 C611 1.496(5) . ? Cl11 C621 1.730(4) . ? Cl21 C631 1.741(5) . ? C611 C621 1.383(6) . ? C611 C661 1.384(6) . ? C621 C631 1.391(6) . ? C631 C641 1.368(8) . ? C641 C651 1.374(8) . ? C641 H641 0.9500 . ? C651 C661 1.382(7) . ? C651 H651 0.9500 . ? C661 H661 0.9500 . ? Br12 C212 2.120(10) . ? C212 C212 1.280(13) 3_656 ? C212 C12 1.548(7) . ? C212 H212 1.0000 . ? C12 O22 1.234(6) . ? C12 O12 1.252(5) . ? O113 C113 1.24(3) . ? C313 C113 1.37(4) . ? C313 H31C 0.9800 . ? C313 H31D 0.9800 . ? C313 H31E 0.9800 . ? C113 C213 1.23(3) . ? C213 H21A 0.9800 . ? C213 H21B 0.9800 . ? C213 H21C 0.9800 . ? O123 C123 1.19(2) . ? C123 C223 1.43(3) . ? C123 C323 1.56(5) . ? C223 H22C 0.9800 . ? C223 H22D 0.9800 . ? C223 H22E 0.9800 . ? C323 H32A 0.9800 . ? C323 H32B 0.9800 . ? C323 H32C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C61 N11 N21 116.3(3) . . ? C31 N21 N11 123.2(3) . . ? C31 N21 H21 118.4 . . ? N11 N21 H21 118.4 . . ? N31 C31 N41 120.4(3) . . ? N31 C31 N21 118.5(3) . . ? N41 C31 N21 121.1(3) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C51 N41 C31 117.1(3) . . ? N51 C51 N41 118.6(3) . . ? N51 C51 C61 121.2(3) . . ? N41 C51 C61 120.2(3) . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? N11 C61 C51 121.0(3) . . ? N11 C61 C611 116.8(3) . . ? C51 C61 C611 122.2(3) . . ? C621 C611 C661 119.5(4) . . ? C621 C611 C61 120.9(3) . . ? C661 C611 C61 119.5(4) . . ? C611 C621 C631 119.9(4) . . ? C611 C621 Cl11 119.7(3) . . ? C631 C621 Cl11 120.4(3) . . ? C641 C631 C621 120.2(4) . . ? C641 C631 Cl21 119.6(4) . . ? C621 C631 Cl21 120.2(4) . . ? C631 C641 C651 120.1(5) . . ? C631 C641 H641 120.0 . . ? C651 C641 H641 120.0 . . ? C641 C651 C661 120.4(5) . . ? C641 C651 H651 119.8 . . ? C661 C651 H651 119.8 . . ? C651 C661 C611 120.0(4) . . ? C651 C661 H661 120.0 . . ? C611 C661 H661 120.0 . . ? C212 C212 C12 121.0(9) 3_656 . ? C212 C212 Br12 100.4(9) 3_656 . ? C12 C212 Br12 102.7(5) . . ? C212 C212 H212 110.5 3_656 . ? C12 C212 H212 110.5 . . ? Br12 C212 H212 110.5 . . ? O22 C12 O12 126.7(4) . . ? O22 C12 C212 113.3(5) . . ? O12 C12 C212 119.9(5) . . ? C113 C313 H31C 109.5 . . ? C113 C313 H31D 109.5 . . ? H31C C313 H31D 109.5 . . ? C113 C313 H31E 109.5 . . ? H31C C313 H31E 109.5 . . ? H31D C313 H31E 109.5 . . ? C213 C113 O113 127(3) . . ? C213 C113 C313 113(3) . . ? O113 C113 C313 119(2) . . ? C113 C213 H21A 109.5 . . ? C113 C213 H21B 109.5 . . ? H21A C213 H21B 109.5 . . ? C113 C213 H21C 109.5 . . ? H21A C213 H21C 109.5 . . ? H21B C213 H21C 109.5 . . ? O123 C123 C223 118(2) . . ? O123 C123 C323 121(3) . . ? C223 C123 C323 118(2) . . ? C123 C223 H22C 109.5 . . ? C123 C223 H22D 109.5 . . ? H22C C223 H22D 109.5 . . ? C123 C223 H22E 109.5 . . ? H22C C223 H22E 109.5 . . ? H22D C223 H22E 109.5 . . ? C123 C323 H32A 109.5 . . ? C123 C323 H32B 109.5 . . ? H32A C323 H32B 109.5 . . ? C123 C323 H32C 109.5 . . ? H32A C323 H32C 109.5 . . ? H32B C323 H32C 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 C61 N11 N21 C31 5.8(5) . . . . ? N11 N21 C31 N31 170.0(4) . . . . ? N11 N21 C31 N41 -11.5(6) . . . . ? N31 C31 N41 C51 -175.1(4) . . . . ? N21 C31 N41 C51 6.4(6) . . . . ? C31 N41 C51 N51 -175.0(4) . . . . ? C31 N41 C51 C61 2.9(6) . . . . ? N21 N11 C61 C51 3.8(5) . . . . ? N21 N11 C61 C611 -178.2(3) . . . . ? N51 C51 C61 N11 169.4(4) . . . . ? N41 C51 C61 N11 -8.4(6) . . . . ? N51 C51 C61 C611 -8.4(6) . . . . ? N41 C51 C61 C611 173.8(4) . . . . ? N11 C61 C611 C621 113.0(4) . . . . ? C51 C61 C611 C621 -69.1(5) . . . . ? N11 C61 C611 C661 -67.7(5) . . . . ? C51 C61 C611 C661 110.2(5) . . . . ? C661 C611 C621 C631 -0.1(6) . . . . ? C61 C611 C621 C631 179.2(4) . . . . ? C661 C611 C621 Cl11 177.9(3) . . . . ? C61 C611 C621 Cl11 -2.8(5) . . . . ? C611 C621 C631 C641 -0.4(7) . . . . ? Cl11 C621 C631 C641 -178.3(4) . . . . ? C611 C621 C631 Cl21 179.7(3) . . . . ? Cl11 C621 C631 Cl21 1.7(5) . . . . ? C621 C631 C641 C651 0.7(8) . . . . ? Cl21 C631 C641 C651 -179.3(5) . . . . ? C631 C641 C651 C661 -0.7(10) . . . . ? C641 C651 C661 C611 0.2(9) . . . . ? C621 C611 C661 C651 0.1(7) . . . . ? C61 C611 C661 C651 -179.2(5) . . . . ? C212 C212 C12 O22 145.2(11) 3_656 . . . ? Br12 C212 C12 O22 -104.2(5) . . . . ? C212 C212 C12 O12 -38.3(15) 3_656 . . . ? Br12 C212 C12 O12 72.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.008 _refine_diff_density_min -0.780 _refine_diff_density_rms 0.074 # Attachment '8451_web_deposit_cif_file_3_JuditGalcera_1322665973.LM12_(ACON).cif' data_LM12_ACON _database_code_depnum_ccdc_archive 'CCDC 856214' #TrackingRef '8451_web_deposit_cif_file_3_JuditGalcera_1322665973.LM12_(ACON).cif' _pd_block_id 2010-12-02T16:30|R4-F10|Fabian|Syncrothron # 5. OVERALL REFINEMENT & COMPUTING DETAILS _refine_special_details ; ? ; _pd_proc_ls_special_details ; ? ; _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 1/\s(Y~obs~)^2^ _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_constraints 1 _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? _refine_diff_density_max 0.44 _refine_diff_density_min -0.42 #============================================================================== # 6. SAMPLE PREPARATION DATA # (In the unusual case where multiple samples are used in a single # Rietveld study, this information should be moved into the phase # blocks) # The following three fields describe the preparation of the material. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate 0 _pd_prep_pressure 100 _pd_prep_temperature 293 _pd_char_colour ? # use ICDD colour descriptions _refine_ls_shift/su_max 0.09 _refine_ls_shift/su_mean 0.01 _computing_structure_refinement GSAS _refine_ls_number_parameters 166 _refine_ls_goodness_of_fit_all 1.98 _refine_ls_number_restraints 138 _refine_ls_matrix_type full #============================================================================== # 7. CHEMICAL, STRUCTURAL AND CRYSTAL DATA _pd_char_particle_morphology 'fine powder' _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - meso-2,3-dibromosuccinate - acetone (2:1:2) ; _chemical_name_common 'bis(lamotriginium) meso-dibromosuccinate' _chemical_formula_moiety 'C9 H8 Cl2 N5, 0.5(C4 H2 Br2 O4), C3 H6 O' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_melting_point ? _chemical_compound_source ? # for minerals and # natural products _symmetry_space_group_name_Hall '-P 2ybc' _exptl_crystal_F_000 908 _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _cell_measurement_temperature 293 _cell_special_details ; ? ; _geom_special_details ? # The following item identifies the program(s) used (if appropriate). _computing_structure_solution DASH #============================================================================== # 8. Phase information from GSAS _pd_phase_name meso-dibr _cell_length_a 11.26187(16) _cell_length_b 11.19534(9) _cell_length_c 16.38551(25) _cell_angle_alpha 90.0 _cell_angle_beta 110.8611(9) _cell_angle_gamma 90.0 _cell_volume 1930.47(4) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +x,+y,+z 2 -x,+y+1/2,-z+1/2 -1 -x,-y,-z -2 +x,-y+1/2,+z+1/2 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_U_iso_or_equiv _atom_site_symmetry_multiplicity _atom_site_disorder_group N N1 0.68061(7) -0.00662(7) -0.10311(8) 1.0 Uiso 0.06824(28) 4 . N N2 0.61040(6) 0.07240(5) -0.164290(35 1.0 Uiso 0.06824(28) 4 . H H2 0.60994(18) 0.06076(7) -0.21515(13) 1.0 Uiso 0.1365(6) 4 . C C3 0.55244(6) 0.16587(6) -0.14708(4) 1.0 Uiso 0.06824(28) 4 . N N4 0.55701(7) 0.18848(7) -0.06704(8) 1.0 Uiso 0.06824(28) 4 . C C5 0.62404(6) 0.11352(6) -0.00563(4) 1.0 Uiso 0.06824(28) 4 . C C6 0.68858(6) 0.01248(6) -0.02564(4) 1.0 Uiso 0.06824(28) 4 . C C7 0.77269(8) -0.06503(6) 0.04217(4) 1.0 Uiso 0.06824(28) 4 . C C8 0.89339(9) -0.02614(5) 0.09382(6) 1.0 Uiso 0.06824(28) 4 . C C9 0.97100(9) -0.09858(7) 0.15763(5) 1.0 Uiso 0.06824(28) 4 . C C10 0.92929(8) -0.21162(5) 0.17155(5) 1.0 Uiso 0.06824(28) 4 . H H10 0.98273(12) -0.26142(9) 0.21514(18) 1.0 Uiso 0.1365(6) 4 . C C11 0.81099(9) -0.25057(5) 0.11993(4) 1.0 Uiso 0.06824(28) 4 . H H11 0.78345(23) -0.32589(34) 0.12910(6) 1.0 Uiso 0.1365(6) 4 . C C12 0.73253(9) -0.17848(5) 0.05497(5) 1.0 Uiso 0.06824(28) 4 . H H12 0.65198(22) -0.20478(7) 0.02081(9) 1.0 Uiso 0.1365(6) 4 . N N3 0.48991(5) 0.23752(5) -0.212824(31 1.0 Uiso 0.06824(28) 4 . H H3A 0.49716(24) 0.22387(7) -0.26274(11) 1.0 Uiso 0.1365(6) 4 . H H3B 0.45155(10) 0.30085(23) -0.20436(5) 1.0 Uiso 0.1365(6) 4 . N N5 0.62997(5) 0.13190(5) 0.075097(30 1.0 Uiso 0.06824(28) 4 . H H5A 0.59771(10) 0.19672(21) 0.08659(5) 1.0 Uiso 0.1365(6) 4 . H H5B 0.66611(7) 0.08051(10) 0.11521(7) 1.0 Uiso 0.1365(6) 4 . Cl Cl8 0.94342(25) 0.11239(24) 0.07812(10) 1.0 Uiso 0.06824(28) 4 . Cl Cl9 1.12253(21) -0.04905(13) 0.22535(13) 1.0 Uiso 0.06824(28) 4 . Br Br22 0.70946(12) 0.04641(11) 0.52648(9) 1.0 Uiso 0.06824(28) 4 . C C22A 0.53251(6) 0.05618(8) 0.52095(4) 0.522(11) Uiso 0.06824(28) 4 1 H H22A 0.49121(7) 0.12691(13) 0.48544(7) 0.522(11) Uiso 0.1365(6) 4 1 C C21 0.53538(24) 0.06751(12) 0.61457(16) 1.0 Uiso 0.06824(28) 4 . O O21A 0.4962(10) 0.1663(9) 0.6252(7) 0.522(11) Uiso 0.06824(28) 4 1 O O22A 0.5770(9) -0.0185(9) 0.6670(6) 0.522(11) Uiso 0.06824(28) 4 1 C C22B 0.55422(6) -0.00915(6) 0.54196(5) 0.478(11) Uiso 0.06824(28) 4 2 H H22B 0.56292(7) -0.09549(27) 0.55845(6) 0.478(11) Uiso 0.1365(6) 4 2 O O21B 0.5424(11) 0.1771(9) 0.6267(7) 0.478(11) Uiso 0.06824(28) 4 2 O O22B 0.5054(10) -0.0038(10) 0.6614(6) 0.478(11) Uiso 0.06824(28) 4 2 C C31 -0.20734(7) 0.51151(6) -0.18933(4) 1.0 Uiso 0.06824(28) 4 . O O31 -0.28612(20) 0.52395(9) -0.26288(21) 1.0 Uiso 0.06824(28) 4 . C C32 -0.17705(4) 0.60983(4) -0.124184(32 1.0 Uiso 0.06824(28) 4 . C C33 -0.13654(4) 0.39854(4) -0.161449(32 1.0 Uiso 0.06824(28) 4 . H H32A -0.09461(7) 0.59329(8) -0.07504(9) 1.0 Uiso 0.1365(6) 4 . H H32B -0.2475(4) 0.61868(8) -0.10003(6) 1.0 Uiso 0.1365(6) 4 . H H32C -0.16577(8) 0.68718(15) -0.15177(6) 1.0 Uiso 0.1365(6) 4 . H H33A -0.15110(11) 0.36488(9) -0.10835(10) 1.0 Uiso 0.1365(6) 4 . H H33B -0.04293(10) 0.41282(8) -0.14402(6) 1.0 Uiso 0.1365(6) 4 . H H33C -0.16484(8) 0.33821(11) -0.21063(9) 1.0 Uiso 0.1365(6) 4 . # If you change Z, be sure to change all 3 of the following _chemical_formula_sum 'C14 H15 Br Cl2 N5 O3' _chemical_formula_weight 452.12 _cell_formula_units_Z 4 # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N2 1.3595(10) . 1_555 N N1 C6 1.2586(15) . 1_555 N N2 H2 0.8416(22) . 1_555 N N2 C3 1.3159(9) . 1_555 N C3 N4 1.3186(15) . 1_555 N C3 N3 1.3265(7) . 1_555 N N4 C5 1.3213(11) . 1_555 N C5 C6 1.4440(10) . 1_555 N C5 N5 1.3166(8) . 1_555 N C6 C7 1.4612(9) . 1_555 N C7 C8 1.3907(11) . 1_555 N C7 C12 1.3890(10) . 1_555 N C8 C9 1.3653(11) . 1_555 N C8 Cl8 1.7006(28) . 1_555 N C9 C10 1.3967(11) . 1_555 N C9 Cl9 1.7614(21) . 1_555 N C10 H10 0.9365(19) . 1_555 N C10 C11 1.3704(11) . 1_555 N C11 H11 0.929(4) . 1_555 N C11 C12 1.3767(9) . 1_555 N C12 H12 0.9281(21) . 1_555 N N3 H3A 0.8640(22) . 1_555 N N3 H3B 0.8667(23) . 1_555 N N5 H5A 0.8619(22) . 1_555 N N5 H5B 0.8591(11) . 1_555 N Br22 C22A 1.9654(16) . 1_555 N Br22 C22B 1.9555(17) . 1_555 N C22A C22A 1.4940(16) . -1_656 N C22A H22A 0.9946(15) . 1_555 N C22A C21 1.5281(28) . 1_555 N C21 O21A 1.226(10) . 1_555 N C21 O22A 1.264(10) . 1_555 N C21 C22B 1.5417(26) . 1_555 N C21 O21B 1.241(10) . 1_555 N C21 O22B 1.235(12) . 1_555 N C22B C22B 1.4929(12) . -1_656 N C22B H22B 0.9990(30) . 1_555 N C31 O31 1.2237(27) . 1_555 N C31 C32 1.4859(8) . 1_555 N C31 C33 1.4781(8) . 1_555 N C32 H32A 1.0060(10) . 1_555 N C32 H32B 1.010(4) . 1_555 N C32 H32C 1.0056(17) . 1_555 N C33 H33A 1.0136(17) . 1_555 N C33 H33B 1.0021(12) . 1_555 N C33 H33C 1.0120(14) . 1_555 N 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C6 116.55(8) 1_555 . 1_555 N N1 N2 H2 115.23(11) 1_555 . 1_555 N N1 N2 C3 124.20(7) 1_555 . 1_555 N H2 N2 C3 120.44(10) 1_555 . 1_555 N N2 C3 N4 121.28(6) 1_555 . 1_555 N N2 C3 N3 117.85(6) 1_555 . 1_555 N N4 C3 N3 120.86(7) 1_555 . 1_555 N C3 N4 C5 116.42(8) 1_555 . 1_555 N N4 C5 C6 121.46(7) 1_555 . 1_555 N N4 C5 N5 118.47(8) 1_555 . 1_555 N C6 C5 N5 120.06(5) 1_555 . 1_555 N N1 C6 C5 120.08(6) 1_555 . 1_555 N N1 C6 C7 117.40(7) 1_555 . 1_555 N C5 C6 C7 122.34(6) 1_555 . 1_555 N C6 C7 C8 120.34(6) 1_555 . 1_555 N C6 C7 C12 120.00(6) 1_555 . 1_555 N C8 C7 C12 119.65(6) 1_555 . 1_555 N C7 C8 C9 120.03(7) 1_555 . 1_555 N C7 C8 Cl8 119.88(9) 1_555 . 1_555 N C9 C8 Cl8 120.09(10) 1_555 . 1_555 N C8 C9 C10 120.17(8) 1_555 . 1_555 N C8 C9 Cl9 120.52(8) 1_555 . 1_555 N C10 C9 Cl9 119.28(8) 1_555 . 1_555 N C9 C10 H10 120.13(10) 1_555 . 1_555 N C9 C10 C11 119.81(6) 1_555 . 1_555 N H10 C10 C11 120.05(10) 1_555 . 1_555 N C10 C11 H11 119.75(13) 1_555 . 1_555 N C10 C11 C12 120.39(6) 1_555 . 1_555 N H11 C11 C12 119.86(14) 1_555 . 1_555 N C7 C12 C11 119.93(7) 1_555 . 1_555 N C7 C12 H12 120.00(9) 1_555 . 1_555 N C11 C12 H12 120.05(9) 1_555 . 1_555 N C3 N3 H3A 117.39(12) 1_555 . 1_555 N C3 N3 H3B 121.03(8) 1_555 . 1_555 N H3A N3 H3B 121.10(12) 1_555 . 1_555 N C5 N5 H5A 118.46(8) 1_555 . 1_555 N C5 N5 H5B 120.31(10) 1_555 . 1_555 N H5A N5 H5B 121.22(11) 1_555 . 1_555 N Br22 C22A C22A 107.30(8) 1_555 . -1_656 N Br22 C22A H22A 109.06(9) 1_555 . 1_555 N Br22 C22A C21 107.44(11) 1_555 . 1_555 N C22A C22A H22A 110.54(8) -1_656 . 1_555 N C22A C22A C21 111.28(10) -1_656 . 1_555 N H22A C22A C21 111.08(11) 1_555 . 1_555 N C22A C21 O21A 109.7(5) 1_555 . 1_555 N C22A C21 O22A 119.3(5) 1_555 . 1_555 N O21A C21 O22A 131.0(7) 1_555 . 1_555 N C22B C21 O21B 130.9(6) 1_555 . 1_555 N C22B C21 O22B 105.3(5) 1_555 . 1_555 N O21B C21 O22B 123.8(8) 1_555 . 1_555 N Br22 C22B C21 107.35(10) 1_555 . 1_555 N Br22 C22B C22B 108.22(8) 1_555 . -1_656 N Br22 C22B H22B 109.68(8) 1_555 . 1_555 N C21 C22B C22B 110.01(10) 1_555 . -1_656 N C21 C22B H22B 110.92(12) 1_555 . 1_555 N C22B C22B H22B 110.56(9) -1_656 . 1_555 N O31 C31 C32 121.58(9) 1_555 . 1_555 N O31 C31 C33 121.59(9) 1_555 . 1_555 N C32 C31 C33 116.83(5) 1_555 . 1_555 N C31 C32 H32A 110.42(8) 1_555 . 1_555 N C31 C32 H32B 110.05(10) 1_555 . 1_555 N C31 C32 H32C 110.39(9) 1_555 . 1_555 N H32A C32 H32B 109.53(14) 1_555 . 1_555 N H32A C32 H32C 106.86(8) 1_555 . 1_555 N H32B C32 H32C 109.54(10) 1_555 . 1_555 N C31 C33 H33A 110.43(8) 1_555 . 1_555 N C31 C33 H33B 110.40(7) 1_555 . 1_555 N C31 C33 H33C 110.05(7) 1_555 . 1_555 N H33A C33 H33B 106.86(9) 1_555 . 1_555 N H33A C33 H33C 109.52(11) 1_555 . 1_555 N H33B C33 H33C 109.53(10) 1_555 . 1_555 N # Powder diffraction data for histogram 1 #============================================================================== # 9. INSTRUMENT CHARACTERIZATION _exptl_special_details ; ? ; # if regions of the data are excluded, the reason(s) are supplied here: _pd_proc_info_excluded_regions ; ? ; # The following item is used to identify the equipment used to record # the powder pattern when the diffractogram was measured at a laboratory # other than the authors' home institution, e.g. when neutron or synchrotron # radiation is used. _pd_instr_location ; ? ; _pd_calibration_special_details # description of the method used # to calibrate the instrument ; ? ; _diffrn_ambient_temperature ? _diffrn_source ? _diffrn_source_target ? _diffrn_source_type ? _diffrn_measurement_device_type ? _diffrn_detector ? _diffrn_detector_type ? # make or model of detector _pd_meas_scan_method ? # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; ? ; # The following two items identify the program(s) used (if appropriate). _computing_data_collection ? _computing_data_reduction ? # Describe any processing performed on the data, prior to refinement. # For example: a manual Lp correction or a precomputed absorption correction _pd_proc_info_data_reduction ? # The following item is used for angular dispersive measurements only. _diffrn_radiation_monochromator ? # The following items are used to define the size of the instrument. # Not all distances are appropriate for all instrument types. _pd_instr_dist_src/mono ? _pd_instr_dist_mono/spec ? _pd_instr_dist_src/spec ? _pd_instr_dist_spec/anal ? _pd_instr_dist_anal/detc ? _pd_instr_dist_spec/detc ? # 10. Specimen size and mounting information # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial ? # perpendicular to # equatorial plane _pd_spec_size_equat ? # parallel to # scattering vector # in transmission _pd_spec_size_thick ? # parallel to # scattering vector # in reflection _pd_spec_mounting # This field should be # used to give details of the # container. ; ? ; _pd_spec_mount_mode ? # options are 'reflection' # or 'transmission' _pd_spec_shape ? # options are 'cylinder' # 'flat_sheet' or 'irregular' loop_ _atom_type_symbol _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source N 20.0 0.000 0.000 12.2126 0.00570 3.13220 9.89330 2.01250 28.9975 1.16630 0.58260 -11.529 International_Tables_Vol_C H 60.0 0.000 0.000 0.49300 10.5109 0.32291 26.1257 0.14019 3.14236 0.04081 57.7997 0.00304 International_Tables_Vol_C C 56.002 0.000 0.000 2.31000 20.8439 1.02000 10.2075 1.58860 0.56870 0.86500 51.6512 0.21560 International_Tables_Vol_C Cl 8.0 0.000 0.000 11.4604 0.01040 7.19640 1.16620 6.25560 18.5194 1.64550 47.7784 -9.5574 International_Tables_Vol_C Br 4.0 0.000 0.000 17.1789 2.17230 5.23580 16.5796 5.63770 0.26090 3.98510 41.4328 2.95570 International_Tables_Vol_C O 12.0 0.000 0.000 3.04850 13.2771 2.28680 5.70110 1.54630 0.32390 0.86700 32.9089 0.25080 International_Tables_Vol_C _diffrn_radiation_probe x-ray _diffrn_radiation_polarisn_ratio ? _diffrn_radiation_wavelength 1.0624 _diffrn_radiation_type ? _pd_proc_ls_prof_R_factor 0.0203 _pd_proc_ls_prof_wR_factor 0.0266 _pd_proc_ls_prof_wR_expected 0.0138 _refine_ls_R_Fsqd_factor 0.10312 _pd_proc_ls_background_function ; GSAS Background function number 1 with 22 terms. Shifted Chebyshev function of 1st kind 1: 4531.12 2: -1970.04 3: -273.640 4: 732.767 5: -641.503 6: -280.984 7: 685.727 8: -365.365 9: -86.0919 10: 374.301 11: -240.534 12: -56.0479 13: 227.026 14: -190.475 15: 8.53448 16: 80.4104 17: -82.5740 18: 46.0784 19: 38.4636 20: -79.2135 21: 66.2305 22: -26.0368 ; _exptl_absorpt_process_details ; GSAS Absorption/surface roughness correction: function number 0 No correction is applied. ; _exptl_absorpt_correction_T_min 1.00000 _exptl_absorpt_correction_T_max 1.00000 # Extinction correction _gsas_exptl_extinct_corr_T_min 1.00000 _gsas_exptl_extinct_corr_T_max 1.00000 _pd_proc_ls_pref_orient_corr ; March-Dollase AXIS 1 Ratio= 0.96424 h= 0.000 k= 1.000 l= 0.000 Prefered orientation correction range: Min= 0.94685, Max= 1.11542 ; _pd_proc_ls_profile_function ; CW Profile function number 2 with 18 terms Profile coefficients for Simpson's rule integration of pseudovoigt function C.J. Howard (1982). J. Appl. Cryst.,15,615-620. P. Thompson, D.E. Cox & J.B. Hastings (1987). J. Appl. Cryst.,20,79-83. #1(GU) = 307.564 #2(GV) = 0.000 #3(GW) = 4.338 #4(LX) = 0.000 #5(LY) = 21.125 #6(trns) = 0.000 #7(asym) = 0.0000 #8(shft) = 0.0000 #9(GP) = 0.000 #10(stec)= 0.00 #11(ptec)= 0.00 #12(sfec)= 0.00 #13(L11) = 0.000 #14(L22) = 0.000 #15(L33) = 0.000 #16(L12) = 0.000 #17(L13) = 0.000 #18(L23) = 0.000 Peak tails are ignored where the intensity is below 0.0025 times the peak Aniso. broadening axis 0.0 0.0 1.0 ; _pd_proc_ls_peak_cutoff 0.00250 _pd_proc_info_datetime 2010-12-02T16:30:02 _pd_calc_method 'Rietveld Refinement' #---- raw/calc data loop ----- _pd_meas_2theta_range_min 2.5 _pd_meas_2theta_range_max 60.0 _pd_meas_2theta_range_inc 0.004 _pd_proc_2theta_range_min 2.49964 _pd_proc_2theta_range_max 59.99964 _pd_proc_2theta_range_inc 0.004 _pd_meas_number_of_points 14376 _pd_proc_number_of_points 14376 _reflns_number_total 1685 _reflns_limit_h_min 0 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min -15 _reflns_limit_l_max 14 _reflns_d_resolution_high 1.063 _reflns_d_resolution_low 10.524 #--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--#