# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_LMAD_BAc _database_code_depnum_ccdc_archive 'CCDC 908273' #TrackingRef '15038_web_deposit_cif_file_0_JuditGalcera_1351546362.LMAD_BAc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - adipate - n-butyl acetate solvate (2:1:1) ; _chemical_name_common 'Lamotrigine hemiadipate n-butyl acetate solvate' _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C6 H8 O4, C6 H12 O2' _chemical_formula_sum 'C30 H36 Cl4 N10 O6' _chemical_formula_weight 774.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.6675(4) _cell_length_b 12.9716(4) _cell_length_c 13.7656(5) _cell_angle_alpha 107.3580(10) _cell_angle_beta 114.6190(10) _cell_angle_gamma 103.1370(10) _cell_volume 1794.35(10) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 20445 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 26.37 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 0.387 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.820 _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 18962 _diffrn_reflns_av_R_equivalents 0.0863 _diffrn_reflns_av_sigmaI/netI 0.1152 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.48 _reflns_number_total 7197 _reflns_number_gt 3958 _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 'Superflip (Palatinus & Chapuis, 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^ > 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^)+(0.1844P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7197 _refine_ls_number_parameters 482 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.1445 _refine_ls_R_factor_gt 0.0821 _refine_ls_wR_factor_ref 0.2942 _refine_ls_wR_factor_gt 0.2564 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.046 _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 0.44702(15) 0.63081(15) 0.11229(14) 0.0685(5) Uani 1 1 d . . . Cl21 Cl 0.63989(17) 0.8578(2) 0.14564(18) 0.0952(7) Uani 1 1 d . . . N11 N 0.3613(4) 0.6437(4) 0.3389(4) 0.0510(12) Uani 1 1 d . . . N21 N 0.2829(4) 0.5522(3) 0.3357(3) 0.0421(10) Uani 1 1 d . . . H21 H 0.3111 0.5337 0.3954 0.051 Uiso 1 1 calc R . . C31 C 0.1628(4) 0.4879(4) 0.2440(4) 0.0349(10) Uani 1 1 d . . . N31 N 0.0912(4) 0.4005(3) 0.2492(3) 0.0392(9) Uani 1 1 d . . . H31A H 0.0119 0.3569 0.1904 0.047 Uiso 1 1 calc R . . H31B H 0.1227 0.3860 0.3114 0.047 Uiso 1 1 calc R . . N41 N 0.1146(3) 0.5099(3) 0.1491(3) 0.0358(9) Uani 1 1 d . . . C51 C 0.1902(4) 0.5983(4) 0.1486(4) 0.0377(11) Uani 1 1 d . . . N51 N 0.1470(4) 0.6258(4) 0.0590(3) 0.0457(11) Uani 1 1 d . . . H51A H 0.0677 0.5852 -0.0006 0.055 Uiso 1 1 calc R . . H51B H 0.1974 0.6847 0.0588 0.055 Uiso 1 1 calc R . . C61 C 0.3182(5) 0.6684(5) 0.2495(5) 0.0476(13) Uani 1 1 d . . . C611 C 0.4048(5) 0.7805(5) 0.2613(5) 0.0612(16) Uani 1 1 d D . . C621 C 0.4702(5) 0.7694(5) 0.2020(5) 0.0624(16) Uani 1 1 d D . . C631 C 0.5578(5) 0.8695(6) 0.2155(6) 0.0646(17) Uani 1 1 d D . . C641 C 0.5798(3) 0.9859(3) 0.2910(3) 0.118(4) Uani 1 1 d D . . H641 H 0.6397 1.0553 0.3038 0.141 Uiso 1 1 calc R . . C651 C 0.5073(3) 0.9901(3) 0.3444(3) 0.081(2) Uani 1 1 d RD . . H651 H 0.5189 1.0671 0.3907 0.097 Uiso 1 1 d R . . C661 C 0.4193(3) 0.8965(3) 0.3394(3) 0.0307(10) Uani 1 1 d RD . . H661 H 0.3749 0.9065 0.3802 0.037 Uiso 1 1 d R . . Cl12 Cl 0.31521(15) 0.11060(14) 0.46739(13) 0.0466(4) Uani 0.8266(18) 1 d P A 1 Cl22 Cl 0.13854(17) 0.13190(15) 0.56998(14) 0.0552(5) Uani 0.8266(18) 1 d P A 1 N12 N 0.1789(5) -0.0139(4) 0.1326(5) 0.0359(15) Uani 0.8266(18) 1 d P A 1 N22 N 0.2576(8) -0.0190(5) 0.0912(6) 0.0372(14) Uani 0.8266(18) 1 d P A 1 H22 H 0.2375 -0.0868 0.0340 0.045 Uiso 0.8266(18) 1 calc PR A 1 C32 C 0.3664(8) 0.0731(7) 0.1314(6) 0.0296(16) Uani 0.8266(18) 1 d P A 1 N42 N 0.4022(8) 0.1783(6) 0.2175(7) 0.0337(15) Uani 0.8266(18) 1 d P A 1 C52 C 0.3267(6) 0.1896(5) 0.2590(6) 0.0301(17) Uani 0.8266(18) 1 d P A 1 C62 C 0.2120(5) 0.0869(5) 0.2154(5) 0.0325(14) Uani 0.8266(18) 1 d P A 1 N32 N 0.4306(9) 0.0537(10) 0.0781(5) 0.0341(17) Uani 0.8266(18) 1 d P A 1 H32A H 0.4999 0.1114 0.0991 0.041 Uiso 0.8266(18) 1 calc PR A 1 H32B H 0.4041 -0.0169 0.0216 0.041 Uiso 0.8266(18) 1 calc PR A 1 N52 N 0.3567(7) 0.2913(8) 0.3409(7) 0.0371(18) Uani 0.8266(18) 1 d P A 1 H52A H 0.4268 0.3517 0.3680 0.045 Uiso 0.8266(18) 1 calc PR A 1 H52B H 0.3070 0.3000 0.3694 0.045 Uiso 0.8266(18) 1 calc PR A 1 C612 C 0.1277(5) 0.0968(4) 0.2670(5) 0.0299(12) Uani 0.8266(18) 1 d PD A 1 C622 C 0.1680(5) 0.1065(4) 0.3813(5) 0.0326(12) Uani 0.8266(18) 1 d PD A 1 C632 C 0.0885(5) 0.1141(6) 0.4269(5) 0.0376(15) Uani 0.8266(18) 1 d PD A 1 C642 C -0.0314(6) 0.1102(5) 0.3566(6) 0.0452(15) Uani 0.8266(18) 1 d PD A 1 H642 H -0.0860 0.1149 0.3870 0.054 Uiso 0.8266(18) 1 calc PR A 1 C652 C -0.0707(6) 0.0995(5) 0.2418(5) 0.0425(14) Uani 0.8266(18) 1 d PD A 1 H652 H -0.1523 0.0965 0.1941 0.051 Uiso 0.8266(18) 1 calc PR A 1 C662 C 0.0083(5) 0.0933(5) 0.1965(6) 0.0411(14) Uani 0.8266(18) 1 d PD A 1 H662 H -0.0184 0.0869 0.1186 0.049 Uiso 0.8266(18) 1 calc PR A 1 O13 O 0.2181(3) 0.3837(3) 0.4636(3) 0.0528(10) Uani 1 1 d . . . O33 O 0.1877(3) 0.7545(2) 0.9345(3) 0.0398(8) Uani 1 1 d . . . O23 O 0.3931(3) 0.5345(3) 0.5318(3) 0.0467(9) Uani 1 1 d . . . O43 O 0.3351(3) 0.8242(3) 0.8958(3) 0.0484(9) Uani 1 1 d . . . C13 C 0.3265(4) 0.4576(4) 0.5453(4) 0.0358(11) Uani 1 1 d . . . C23 C 0.3847(5) 0.4540(4) 0.6645(4) 0.0399(11) Uani 1 1 d . . . H23A H 0.4722 0.5161 0.7178 0.048 Uiso 1 1 calc R . . H23B H 0.3898 0.3766 0.6528 0.048 Uiso 1 1 calc R . . C33 C 0.3074(5) 0.4730(4) 0.7239(4) 0.0388(11) Uani 1 1 d . . . H33A H 0.2164 0.4223 0.6642 0.047 Uiso 1 1 calc R . . H33B H 0.3335 0.4476 0.7882 0.047 Uiso 1 1 calc R . . C43 C 0.3234(4) 0.5997(4) 0.7761(4) 0.0386(11) Uani 1 1 d . . . H43A H 0.4119 0.6486 0.8435 0.046 Uiso 1 1 calc R . . H43B H 0.3091 0.6287 0.7147 0.046 Uiso 1 1 calc R . . C53 C 0.2345(5) 0.6160(4) 0.8193(4) 0.0410(11) Uani 1 1 d . . . H53A H 0.2397 0.5754 0.8706 0.049 Uiso 1 1 calc R . . H53B H 0.1468 0.5756 0.7492 0.049 Uiso 1 1 calc R . . C63 C 0.2561(4) 0.7412(4) 0.8880(4) 0.0355(10) Uani 1 1 d . . . O14 O 0.0179(5) 0.6846(4) 0.3356(5) 0.0896(15) Uani 1 1 d . . . O24 O 0.2118(8) 0.7935(9) 0.4705(9) 0.226(6) Uani 1 1 d . . . C14 C 0.1042(11) 0.6418(9) 0.4942(7) 0.137(5) Uani 1 1 d . . . H14A H 0.0180 0.5796 0.4477 0.205 Uiso 1 1 calc R . . H14B H 0.1209 0.6928 0.5723 0.205 Uiso 1 1 calc R . . H14C H 0.1658 0.6058 0.5050 0.205 Uiso 1 1 calc R . . C24 C 0.1150(8) 0.7084(8) 0.4344(8) 0.105(3) Uani 1 1 d . . . C34 C 0.0177(8) 0.7516(6) 0.2678(8) 0.094(2) Uani 1 1 d . . . H34A H 0.0871 0.7550 0.2514 0.113 Uiso 1 1 calc R . . H34B H 0.0324 0.8335 0.3147 0.113 Uiso 1 1 calc R . . C44 C -0.1094(8) 0.6934(7) 0.1506(7) 0.091(2) Uani 1 1 d . . . H44A H -0.1231 0.6113 0.1058 0.109 Uiso 1 1 calc R . . H44B H -0.1776 0.6894 0.1688 0.109 Uiso 1 1 calc R . . C54 C -0.1221(11) 0.7526(7) 0.0732(10) 0.112(3) Uani 1 1 d . . . H54A H -0.1115 0.8338 0.1171 0.134 Uiso 1 1 calc R . . H54B H -0.0518 0.7594 0.0578 0.134 Uiso 1 1 calc R . . C64 C -0.2391(13) 0.6967(12) -0.0387(11) 0.138(4) Uani 1 1 d . . . H64A H -0.2375 0.7425 -0.0837 0.207 Uiso 1 1 calc R . . H64B H -0.3096 0.6926 -0.0251 0.207 Uiso 1 1 calc R . . H64C H -0.2504 0.6167 -0.0842 0.207 Uiso 1 1 calc R . . Cl15 Cl 0.0083(7) 0.0997(7) 0.1280(7) 0.0466(4) Uani 0.1734(18) 1 d P A 2 Cl25 Cl -0.1272(8) 0.1375(7) 0.2699(7) 0.0552(5) Uani 0.1734(18) 1 d P A 2 N15 N 0.207(3) -0.032(2) 0.154(3) 0.0359(15) Uani 0.1734(18) 1 d PG A 2 N25 N 0.258(4) -0.044(3) 0.081(3) 0.0372(14) Uani 0.1734(18) 1 d PG A 2 H25 H 0.2286 -0.1122 0.0205 0.045 Uiso 0.1734(18) 1 calc PR A 2 C35 C 0.355(5) 0.053(4) 0.104(4) 0.0296(16) Uani 0.1734(18) 1 d PG A 2 N45 N 0.401(4) 0.162(4) 0.199(4) 0.0337(15) Uani 0.1734(18) 1 d PG A 2 C55 C 0.350(3) 0.173(2) 0.272(3) 0.0301(17) Uani 0.1734(18) 1 d PG A 2 C65 C 0.253(3) 0.076(2) 0.249(2) 0.0325(14) Uani 0.1734(18) 1 d PG A 2 N35 N 0.409(6) 0.048(6) 0.047(4) 0.0341(17) Uani 0.1734(18) 1 d P A 2 H35A H 0.4732 0.1110 0.0679 0.041 Uiso 0.1734(18) 1 calc PR A 2 H35B H 0.3833 -0.0186 -0.0142 0.041 Uiso 0.1734(18) 1 calc PR A 2 N55 N 0.387(5) 0.282(5) 0.365(4) 0.0371(18) Uani 0.1734(18) 1 d P A 2 H55A H 0.4436 0.3469 0.3785 0.045 Uiso 0.1734(18) 1 calc PR A 2 H55B H 0.3522 0.2862 0.4090 0.045 Uiso 0.1734(18) 1 calc PR A 2 C615 C 0.175(2) 0.082(2) 0.310(2) 0.0299(12) Uani 0.1734(18) 1 d PD A 2 C625 C 0.066(3) 0.101(2) 0.261(2) 0.0326(12) Uani 0.1734(18) 1 d PD A 2 C635 C 0.006(2) 0.121(3) 0.327(2) 0.0376(15) Uani 0.1734(18) 1 d PD A 2 C645 C 0.053(3) 0.113(4) 0.436(3) 0.0452(15) Uani 0.1734(18) 1 d PD A 2 H645 H 0.0063 0.1152 0.4752 0.054 Uiso 0.1734(18) 1 calc PR A 2 C655 C 0.167(2) 0.102(2) 0.486(2) 0.0425(14) Uani 0.1734(18) 1 d PD A 2 H655 H 0.2023 0.1047 0.5632 0.051 Uiso 0.1734(18) 1 calc PR A 2 C665 C 0.234(2) 0.086(3) 0.426(2) 0.0411(14) Uani 0.1734(18) 1 d PD A 2 H665 H 0.3120 0.0782 0.4606 0.049 Uiso 0.1734(18) 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 0.0668(10) 0.0824(11) 0.0579(9) 0.0342(8) 0.0340(8) 0.0258(8) Cl21 0.0685(11) 0.1314(17) 0.0813(12) 0.0632(12) 0.0372(10) 0.0155(11) N11 0.038(2) 0.053(2) 0.042(2) 0.031(2) 0.0079(19) -0.0021(19) N21 0.035(2) 0.042(2) 0.028(2) 0.0170(18) 0.0072(18) -0.0010(18) C31 0.033(2) 0.034(2) 0.030(2) 0.0113(19) 0.015(2) 0.006(2) N31 0.035(2) 0.037(2) 0.030(2) 0.0165(17) 0.0101(17) 0.0025(17) N41 0.033(2) 0.036(2) 0.0257(19) 0.0138(16) 0.0092(17) 0.0049(17) C51 0.029(2) 0.039(2) 0.038(3) 0.019(2) 0.014(2) 0.005(2) N51 0.029(2) 0.055(2) 0.035(2) 0.026(2) 0.0070(18) 0.0004(18) C61 0.033(3) 0.056(3) 0.042(3) 0.026(3) 0.013(2) 0.006(2) C611 0.040(3) 0.085(4) 0.048(3) 0.040(3) 0.012(3) 0.015(3) C621 0.047(3) 0.087(4) 0.046(3) 0.042(3) 0.014(3) 0.020(3) C631 0.045(3) 0.080(4) 0.065(4) 0.048(4) 0.019(3) 0.017(3) C641 0.094(6) 0.274(14) 0.107(7) 0.155(9) 0.076(6) 0.128(8) C651 0.074(4) 0.047(3) 0.067(4) 0.021(3) 0.002(4) 0.013(3) C661 0.021(2) 0.0184(19) 0.029(2) 0.0083(17) -0.0007(18) 0.0013(17) Cl12 0.0418(9) 0.0623(9) 0.0352(8) 0.0257(7) 0.0165(7) 0.0220(7) Cl22 0.0663(10) 0.0584(9) 0.0426(9) 0.0220(7) 0.0354(8) 0.0149(8) N12 0.037(3) 0.031(2) 0.035(3) 0.009(2) 0.021(3) 0.010(2) N22 0.044(2) 0.023(3) 0.032(2) -0.003(2) 0.026(2) 0.004(3) C32 0.034(3) 0.026(5) 0.017(4) 0.003(4) 0.011(4) 0.005(3) N42 0.037(2) 0.029(3) 0.027(3) 0.005(2) 0.019(2) 0.005(2) C52 0.030(3) 0.029(3) 0.027(3) 0.012(2) 0.013(3) 0.010(2) C62 0.034(4) 0.034(3) 0.025(3) 0.012(2) 0.015(3) 0.009(3) N32 0.034(5) 0.036(2) 0.024(5) 0.009(4) 0.016(4) 0.006(3) N52 0.035(5) 0.034(3) 0.031(4) 0.008(3) 0.016(4) 0.005(3) C612 0.022(3) 0.029(3) 0.029(3) 0.011(2) 0.008(3) 0.008(2) C622 0.030(3) 0.026(3) 0.029(3) 0.009(2) 0.011(2) 0.005(2) C632 0.038(4) 0.037(3) 0.039(3) 0.016(3) 0.024(3) 0.010(3) C642 0.046(4) 0.038(3) 0.057(4) 0.018(3) 0.035(3) 0.013(3) C652 0.042(3) 0.045(3) 0.046(4) 0.021(3) 0.027(3) 0.018(3) C662 0.037(3) 0.041(3) 0.037(3) 0.018(3) 0.014(3) 0.010(3) O13 0.049(2) 0.0444(19) 0.0372(19) 0.0206(16) 0.0104(17) -0.0045(17) O33 0.0435(18) 0.0322(16) 0.0379(18) 0.0105(14) 0.0240(16) 0.0073(14) O23 0.0414(19) 0.0479(19) 0.0335(18) 0.0190(15) 0.0128(15) 0.0027(16) O43 0.055(2) 0.0311(17) 0.059(2) 0.0115(16) 0.0414(19) 0.0049(16) C13 0.041(3) 0.029(2) 0.028(2) 0.009(2) 0.016(2) 0.010(2) C23 0.051(3) 0.039(2) 0.031(2) 0.017(2) 0.020(2) 0.019(2) C33 0.048(3) 0.033(2) 0.033(2) 0.016(2) 0.021(2) 0.013(2) C43 0.040(3) 0.035(2) 0.035(3) 0.014(2) 0.017(2) 0.013(2) C53 0.044(3) 0.035(2) 0.039(3) 0.012(2) 0.024(2) 0.010(2) C63 0.035(2) 0.039(3) 0.027(2) 0.012(2) 0.016(2) 0.012(2) O14 0.064(3) 0.088(3) 0.078(3) 0.030(3) 0.021(3) 0.011(3) O24 0.095(5) 0.172(8) 0.208(10) 0.046(7) -0.035(6) 0.007(6) C14 0.191(11) 0.106(7) 0.054(5) 0.019(5) 0.011(6) 0.094(7) C24 0.058(5) 0.085(6) 0.083(6) -0.016(5) 0.000(4) 0.028(4) C34 0.092(6) 0.069(4) 0.121(7) 0.037(5) 0.066(6) 0.021(4) C44 0.098(6) 0.075(5) 0.093(6) 0.037(4) 0.052(5) 0.019(4) C54 0.150(9) 0.076(5) 0.143(9) 0.066(6) 0.091(8) 0.048(6) C64 0.194(12) 0.197(12) 0.132(9) 0.117(9) 0.110(10) 0.146(11) Cl15 0.0418(9) 0.0623(9) 0.0352(8) 0.0257(7) 0.0165(7) 0.0220(7) Cl25 0.0663(10) 0.0584(9) 0.0426(9) 0.0220(7) 0.0354(8) 0.0149(8) N15 0.037(3) 0.031(2) 0.035(3) 0.009(2) 0.021(3) 0.010(2) N25 0.044(2) 0.023(3) 0.032(2) -0.003(2) 0.026(2) 0.004(3) C35 0.034(3) 0.026(5) 0.017(4) 0.003(4) 0.011(4) 0.005(3) N45 0.037(2) 0.029(3) 0.027(3) 0.005(2) 0.019(2) 0.005(2) C55 0.030(3) 0.029(3) 0.027(3) 0.012(2) 0.013(3) 0.010(2) C65 0.034(4) 0.034(3) 0.025(3) 0.012(2) 0.015(3) 0.009(3) N35 0.034(5) 0.036(2) 0.024(5) 0.009(4) 0.016(4) 0.006(3) N55 0.035(5) 0.034(3) 0.031(4) 0.008(3) 0.016(4) 0.005(3) C615 0.022(3) 0.029(3) 0.029(3) 0.011(2) 0.008(3) 0.008(2) C625 0.030(3) 0.026(3) 0.029(3) 0.009(2) 0.011(2) 0.005(2) C635 0.038(4) 0.037(3) 0.039(3) 0.016(3) 0.024(3) 0.010(3) C645 0.046(4) 0.038(3) 0.057(4) 0.018(3) 0.035(3) 0.013(3) C655 0.042(3) 0.045(3) 0.046(4) 0.021(3) 0.027(3) 0.018(3) C665 0.037(3) 0.041(3) 0.037(3) 0.018(3) 0.014(3) 0.010(3) _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 1.725(7) . ? Cl21 C631 1.687(7) . ? N11 C61 1.294(6) . ? N11 N21 1.338(5) . ? N21 C31 1.341(6) . ? N21 H21 0.8800 . ? C31 N31 1.323(6) . ? C31 N41 1.341(6) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N41 C51 1.320(5) . ? C51 N51 1.318(6) . ? C51 C61 1.444(7) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C61 C611 1.526(7) . ? C611 C621 1.385(8) . ? C611 C661 1.482(7) . ? C621 C631 1.409(8) . ? C631 C641 1.438(7) . ? C641 C651 1.3942 . ? C641 H641 0.9500 . ? C651 C661 1.4123 . ? C651 H651 0.9500 . ? C661 H661 0.9500 . ? Cl12 C622 1.721(6) . ? Cl22 C632 1.719(6) . ? N12 C62 1.284(7) . ? N12 N22 1.344(7) . ? N22 C32 1.361(7) . ? N22 H22 0.8800 . ? C32 N32 1.321(14) . ? C32 N42 1.334(7) . ? N42 C52 1.315(7) . ? C52 N52 1.298(11) . ? C52 C62 1.471(7) . ? C62 C612 1.517(8) . ? N32 H32A 0.8800 . ? N32 H32B 0.8800 . ? N52 H52A 0.8800 . ? N52 H52B 0.8800 . ? C612 C622 1.390(7) . ? C612 C662 1.397(8) . ? C622 C632 1.397(7) . ? C632 C642 1.399(8) . ? C642 C652 1.396(8) . ? C642 H642 0.9500 . ? C652 C662 1.386(8) . ? C652 H652 0.9500 . ? C662 H662 0.9500 . ? O13 C13 1.241(5) . ? O33 C63 1.287(5) . ? O23 C13 1.265(5) . ? O43 C63 1.233(5) . ? C13 C23 1.514(6) . ? C23 C33 1.532(7) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C33 C43 1.511(6) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C43 C53 1.502(7) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C53 C63 1.508(7) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? O14 C24 1.282(10) . ? O14 C34 1.453(10) . ? O24 C24 1.232(13) . ? C14 C24 1.381(15) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C34 C44 1.524(12) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C44 C54 1.466(12) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C54 C64 1.427(15) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? Cl15 C625 1.65(2) . ? Cl25 C635 1.63(2) . ? N15 N25 1.3900 . ? N15 C65 1.3900 . ? N25 C35 1.3900 . ? N25 H25 0.8800 . ? C35 N35 1.23(7) . ? C35 N45 1.3900 . ? N45 C55 1.3900 . ? C55 C65 1.3900 . ? C55 N55 1.41(6) . ? C65 C615 1.54(3) . ? N35 H35A 0.8800 . ? N35 H35B 0.8800 . ? N55 H55A 0.8800 . ? N55 H55B 0.8800 . ? C615 C625 1.384(16) . ? C615 C665 1.433(16) . ? C625 C635 1.422(17) . ? C635 C645 1.406(16) . ? C645 C655 1.388(16) . ? C645 H645 0.9500 . ? C655 C665 1.402(16) . ? C655 H655 0.9500 . ? C665 H665 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 117.9(4) . . ? N11 N21 C31 122.0(4) . . ? N11 N21 H21 119.0 . . ? C31 N21 H21 119.0 . . ? N31 C31 N41 119.9(4) . . ? N31 C31 N21 118.0(4) . . ? N41 C31 N21 122.1(4) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C51 N41 C31 117.4(4) . . ? N51 C51 N41 120.0(4) . . ? N51 C51 C61 120.2(4) . . ? N41 C51 C61 119.7(4) . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? N11 C61 C51 120.9(4) . . ? N11 C61 C611 116.7(4) . . ? C51 C61 C611 122.2(4) . . ? C621 C611 C661 122.9(5) . . ? C621 C611 C61 118.4(6) . . ? C661 C611 C61 118.7(5) . . ? C611 C621 C631 121.2(6) . . ? C611 C621 Cl11 119.8(5) . . ? C631 C621 Cl11 119.0(5) . . ? C621 C631 C641 119.9(6) . . ? C621 C631 Cl21 121.9(5) . . ? C641 C631 Cl21 118.2(4) . . ? C651 C641 C631 115.6(3) . . ? C651 C641 H641 122.2 . . ? C631 C641 H641 122.2 . . ? C641 C651 C661 129.3 . . ? C641 C651 H651 115.3 . . ? C661 C651 H651 115.3 . . ? C651 C661 C611 111.0(2) . . ? C651 C661 H661 124.5 . . ? C611 C661 H661 124.6 . . ? C62 N12 N22 115.3(4) . . ? N12 N22 C32 124.6(4) . . ? N12 N22 H22 117.7 . . ? C32 N22 H22 117.7 . . ? N32 C32 N42 122.5(7) . . ? N32 C32 N22 116.7(7) . . ? N42 C32 N22 120.8(5) . . ? C52 N42 C32 117.3(4) . . ? N52 C52 N42 119.2(7) . . ? N52 C52 C62 120.7(7) . . ? N42 C52 C62 120.1(5) . . ? N12 C62 C52 121.8(5) . . ? N12 C62 C612 117.4(5) . . ? C52 C62 C612 120.8(5) . . ? C32 N32 H32A 120.0 . . ? C32 N32 H32B 120.0 . . ? H32A N32 H32B 120.0 . . ? C52 N52 H52A 120.0 . . ? C52 N52 H52B 120.0 . . ? H52A N52 H52B 120.0 . . ? C622 C612 C662 121.0(5) . . ? C622 C612 C62 120.4(5) . . ? C662 C612 C62 118.6(5) . . ? C612 C622 C632 119.7(5) . . ? C612 C622 Cl12 120.6(4) . . ? C632 C622 Cl12 119.7(4) . . ? C622 C632 C642 119.6(5) . . ? C622 C632 Cl22 120.5(4) . . ? C642 C632 Cl22 119.8(4) . . ? C652 C642 C632 119.9(6) . . ? C652 C642 H642 120.0 . . ? C632 C642 H642 120.0 . . ? C662 C652 C642 120.7(6) . . ? C662 C652 H652 119.7 . . ? C642 C652 H652 119.7 . . ? C652 C662 C612 119.1(6) . . ? C652 C662 H662 120.5 . . ? C612 C662 H662 120.5 . . ? O13 C13 O23 122.4(4) . . ? O13 C13 C23 119.6(4) . . ? O23 C13 C23 117.9(4) . . ? C13 C23 C33 111.9(4) . . ? C13 C23 H23A 109.2 . . ? C33 C23 H23A 109.2 . . ? C13 C23 H23B 109.2 . . ? C33 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C43 C33 C23 113.4(4) . . ? C43 C33 H33A 108.9 . . ? C23 C33 H33A 108.9 . . ? C43 C33 H33B 108.9 . . ? C23 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? C53 C43 C33 113.6(4) . . ? C53 C43 H43A 108.9 . . ? C33 C43 H43A 108.9 . . ? C53 C43 H43B 108.9 . . ? C33 C43 H43B 108.9 . . ? H43A C43 H43B 107.7 . . ? C43 C53 C63 117.0(4) . . ? C43 C53 H53A 108.1 . . ? C63 C53 H53A 108.1 . . ? C43 C53 H53B 108.1 . . ? C63 C53 H53B 108.1 . . ? H53A C53 H53B 107.3 . . ? O43 C63 O33 123.6(4) . . ? O43 C63 C53 119.9(4) . . ? O33 C63 C53 116.5(4) . . ? C24 O14 C34 123.8(7) . . ? C24 C14 H14A 109.5 . . ? C24 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C24 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O24 C24 O14 115.8(12) . . ? O24 C24 C14 124.9(10) . . ? O14 C24 C14 119.3(9) . . ? O14 C34 C44 109.9(6) . . ? O14 C34 H34A 109.7 . . ? C44 C34 H34A 109.7 . . ? O14 C34 H34B 109.7 . . ? C44 C34 H34B 109.7 . . ? H34A C34 H34B 108.2 . . ? C54 C44 C34 115.4(7) . . ? C54 C44 H44A 108.4 . . ? C34 C44 H44A 108.4 . . ? C54 C44 H44B 108.4 . . ? C34 C44 H44B 108.4 . . ? H44A C44 H44B 107.5 . . ? C64 C54 C44 115.9(9) . . ? C64 C54 H54A 108.3 . . ? C44 C54 H54A 108.3 . . ? C64 C54 H54B 108.3 . . ? C44 C54 H54B 108.3 . . ? H54A C54 H54B 107.4 . . ? C54 C64 H64A 109.5 . . ? C54 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? C54 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? N25 N15 C65 120.0 . . ? N15 N25 C35 120.0 . . ? N15 N25 H25 120.0 . . ? C35 N25 H25 120.0 . . ? N35 C35 N45 116(4) . . ? N35 C35 N25 123(4) . . ? N45 C35 N25 120.0 . . ? C35 N45 C55 120.0 . . ? N45 C55 C65 120.0 . . ? N45 C55 N55 123(3) . . ? C65 C55 N55 117(3) . . ? C55 C65 N15 120.0 . . ? C55 C65 C615 125(2) . . ? N15 C65 C615 115(2) . . ? C35 N35 H35A 120.0 . . ? C35 N35 H35B 120.0 . . ? H35A N35 H35B 120.0 . . ? C55 N55 H55A 120.0 . . ? C55 N55 H55B 120.0 . . ? H55A N55 H55B 120.0 . . ? C625 C615 C665 124.1(18) . . ? C625 C615 C65 119.4(19) . . ? C665 C615 C65 115.7(19) . . ? C615 C625 C635 117.4(17) . . ? C615 C625 Cl15 120.4(17) . . ? C635 C625 Cl15 122.2(18) . . ? C645 C635 C625 120.0(18) . . ? C645 C635 Cl25 120.3(17) . . ? C625 C635 Cl25 119.3(18) . . ? C655 C645 C635 120.1(18) . . ? C655 C645 H645 120.0 . . ? C635 C645 H645 120.0 . . ? C645 C655 C665 122.2(18) . . ? C645 C655 H655 118.9 . . ? C665 C655 H655 118.9 . . ? C655 C665 C615 115.6(18) . . ? C655 C665 H665 122.2 . . ? C615 C665 H665 122.2 . . ? 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 C61 N11 N21 C31 -0.7(8) . . . . ? N11 N21 C31 N31 -178.6(4) . . . . ? N11 N21 C31 N41 1.2(7) . . . . ? N31 C31 N41 C51 179.8(4) . . . . ? N21 C31 N41 C51 0.0(7) . . . . ? C31 N41 C51 N51 -178.4(4) . . . . ? C31 N41 C51 C61 -1.5(7) . . . . ? N21 N11 C61 C51 -0.9(8) . . . . ? N21 N11 C61 C611 173.9(5) . . . . ? N51 C51 C61 N11 178.9(5) . . . . ? N41 C51 C61 N11 2.1(8) . . . . ? N51 C51 C61 C611 4.4(8) . . . . ? N41 C51 C61 C611 -172.4(5) . . . . ? N11 C61 C611 C621 102.7(6) . . . . ? C51 C61 C611 C621 -82.6(7) . . . . ? N11 C61 C611 C661 -74.9(6) . . . . ? C51 C61 C611 C661 99.8(6) . . . . ? C661 C611 C621 C631 1.6(8) . . . . ? C61 C611 C621 C631 -175.9(5) . . . . ? C661 C611 C621 Cl11 -179.7(3) . . . . ? C61 C611 C621 Cl11 2.8(7) . . . . ? C611 C621 C631 C641 -0.5(8) . . . . ? Cl11 C621 C631 C641 -179.2(4) . . . . ? C611 C621 C631 Cl21 179.1(4) . . . . ? Cl11 C621 C631 Cl21 0.4(7) . . . . ? C621 C631 C641 C651 -1.6(6) . . . . ? Cl21 C631 C641 C651 178.7(2) . . . . ? C631 C641 C651 C661 3.2(3) . . . . ? C641 C651 C661 C611 -2.2(2) . . . . ? C621 C611 C661 C651 -0.4(5) . . . . ? C61 C611 C661 C651 177.1(3) . . . . ? C62 N12 N22 C32 0.4(9) . . . . ? N12 N22 C32 N32 -177.9(10) . . . . ? N12 N22 C32 N42 -0.3(9) . . . . ? N32 C32 N42 C52 175.7(10) . . . . ? N22 C32 N42 C52 -1.8(8) . . . . ? C32 N42 C52 N52 -178.4(6) . . . . ? C32 N42 C52 C62 3.5(8) . . . . ? N22 N12 C62 C52 1.5(9) . . . . ? N22 N12 C62 C612 -178.8(6) . . . . ? N52 C52 C62 N12 178.4(5) . . . . ? N42 C52 C62 N12 -3.6(9) . . . . ? N52 C52 C62 C612 -1.3(8) . . . . ? N42 C52 C62 C612 176.7(6) . . . . ? N12 C62 C612 C622 107.9(6) . . . . ? C52 C62 C612 C622 -72.4(7) . . . . ? N12 C62 C612 C662 -70.8(7) . . . . ? C52 C62 C612 C662 108.9(6) . . . . ? C662 C612 C622 C632 -0.5(8) . . . . ? C62 C612 C622 C632 -179.2(5) . . . . ? C662 C612 C622 Cl12 180.0(4) . . . . ? C62 C612 C622 Cl12 1.3(7) . . . . ? C612 C622 C632 C642 0.8(9) . . . . ? Cl12 C622 C632 C642 -179.7(5) . . . . ? C612 C622 C632 Cl22 -177.5(4) . . . . ? Cl12 C622 C632 Cl22 2.0(7) . . . . ? C622 C632 C642 C652 -0.3(9) . . . . ? Cl22 C632 C642 C652 178.0(5) . . . . ? C632 C642 C652 C662 -0.4(9) . . . . ? C642 C652 C662 C612 0.6(8) . . . . ? C622 C612 C662 C652 -0.2(8) . . . . ? C62 C612 C662 C652 178.5(5) . . . . ? O13 C13 C23 C33 -61.6(6) . . . . ? O23 C13 C23 C33 120.8(5) . . . . ? C13 C23 C33 C43 -74.7(5) . . . . ? C23 C33 C43 C53 172.1(4) . . . . ? C33 C43 C53 C63 171.7(4) . . . . ? C43 C53 C63 O43 7.3(7) . . . . ? C43 C53 C63 O33 -173.5(4) . . . . ? C34 O14 C24 O24 -0.1(13) . . . . ? C34 O14 C24 C14 177.7(8) . . . . ? C24 O14 C34 C44 175.4(7) . . . . ? O14 C34 C44 C54 180.0(7) . . . . ? C34 C44 C54 C64 177.9(8) . . . . ? C65 N15 N25 C35 0.0 . . . . ? N15 N25 C35 N35 176(6) . . . . ? N15 N25 C35 N45 0.0 . . . . ? N35 C35 N45 C55 -176(5) . . . . ? N25 C35 N45 C55 0.0 . . . . ? C35 N45 C55 C65 0.0 . . . . ? C35 N45 C55 N55 -175(4) . . . . ? N45 C55 C65 N15 0.0 . . . . ? N55 C55 C65 N15 176(3) . . . . ? N45 C55 C65 C615 -170(3) . . . . ? N55 C55 C65 C615 6(4) . . . . ? N25 N15 C65 C55 0.0 . . . . ? N25 N15 C65 C615 171(3) . . . . ? C55 C65 C615 C625 89(3) . . . . ? N15 C65 C615 C625 -81(3) . . . . ? C55 C65 C615 C665 -81(3) . . . . ? N15 C65 C615 C665 108(3) . . . . ? C665 C615 C625 C635 -3(4) . . . . ? C65 C615 C625 C635 -172(2) . . . . ? C665 C615 C625 Cl15 178(2) . . . . ? C65 C615 C625 Cl15 8(4) . . . . ? C615 C625 C635 C645 -4(5) . . . . ? Cl15 C625 C635 C645 175(3) . . . . ? C615 C625 C635 Cl25 -177(2) . . . . ? Cl15 C625 C635 Cl25 2(4) . . . . ? C625 C635 C645 C655 9(6) . . . . ? Cl25 C635 C645 C655 -178(3) . . . . ? C635 C645 C655 C665 -7(6) . . . . ? C645 C655 C665 C615 0(4) . . . . ? C625 C615 C665 C655 5(4) . . . . ? C65 C615 C665 C655 175(2) . . . . ? N11 C61 C611 C621 102.7(6) . . . . ? N12 C62 C612 C622 107.9(6) . . . . ? N15 C65 C615 C625 -81(3) . . . . ? O13 C13 C23 C33 -61.6(6) . . . . ? O43 C63 C53 C43 7.3(7) . . . . ? 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 O23 0.88 1.72 2.582(5) 165.4 . N31 H31A O33 0.88 2.16 3.035(5) 171.6 2_566 N31 H31B O13 0.88 1.95 2.817(5) 169.1 . N51 H51A N41 0.88 2.07 2.952(5) 176.0 2_565 N51 H51B O33 0.88 2.13 2.836(5) 136.2 1_554 N22 H22 O33 0.88 1.88 2.741(6) 166.8 1_544 N32 H32A O43 0.88 2.03 2.843(12) 153.0 2_666 N32 H32B O43 0.88 1.95 2.829(12) 176.3 1_544 N35 H35B O43 0.88 1.83 2.68(7) 160.6 1_544 N35 H35A O43 0.88 2.16 2.92(6) 144.5 2_666 N52 H52A O23 0.88 1.98 2.824(9) 160.4 2_666 N52 H52B O13 0.88 2.25 3.097(11) 161.5 . N25 H25 O33 0.88 1.59 2.45(3) 166.9 1_544 N55 H55B O13 0.88 2.55 3.28(6) 140.3 . N55 H55A O23 0.88 1.86 2.67(5) 151.6 2_666 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 26.48 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 1.083 _refine_diff_density_min -0.730 _refine_diff_density_rms 0.119 data_LMAD_thf _database_code_depnum_ccdc_archive 'CCDC 908274' #TrackingRef '15039_web_deposit_cif_file_1_JuditGalcera_1351546362.LMAD_thf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - adipate - tetrahydofuran solvate (2:1:2) ; _chemical_name_common 'Lamotrigine hemiadipate tetrahydrofuran solvate' _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C6 H8 O4, 2(C4 H8 O)' _chemical_formula_sum 'C32 H40 Cl4 N10 O6' _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' 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.6839(2) _cell_length_b 13.1519(2) _cell_length_c 13.6466(2) _cell_angle_alpha 107.0840(10) _cell_angle_beta 114.3670(10) _cell_angle_gamma 101.9840(10) _cell_volume 1835.40(5) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 24102 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.10 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 836 _exptl_absorpt_coefficient_mu 0.381 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.908 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_process_details ? _exptl_special_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 28408 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 27.08 _reflns_number_total 8026 _reflns_number_gt 5962 _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^)+(0.0500P)^2^+4.0347P] 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 8026 _refine_ls_number_parameters 535 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.0989 _refine_ls_R_factor_gt 0.0719 _refine_ls_wR_factor_ref 0.1805 _refine_ls_wR_factor_gt 0.1678 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.105 _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 0.18056(9) 0.38999(10) 0.02992(8) 0.0453(3) Uani 1 1 d . . . Cl21 Cl 0.35683(10) 0.37068(10) -0.07495(9) 0.0516(3) Uani 1 1 d . . . N11 N 0.3142(3) 0.5054(3) 0.3631(2) 0.0323(6) Uani 1 1 d . . . N21 N 0.2410(3) 0.5160(3) 0.4120(2) 0.0322(6) Uani 1 1 d . . . H21 H 0.2625 0.5821 0.4698 0.039 Uiso 1 1 calc R . . C31 C 0.1350(3) 0.4273(3) 0.3745(3) 0.0297(7) Uani 1 1 d . . . N31 N 0.0719(3) 0.4468(3) 0.4297(3) 0.0367(7) Uani 1 1 d . . . H31A H 0.0034 0.3918 0.4090 0.044 Uiso 1 1 calc R . . H31B H 0.0984 0.5148 0.4872 0.044 Uiso 1 1 calc R . . N41 N 0.0959(3) 0.3248(2) 0.2873(2) 0.0300(6) Uani 1 1 d . . . C51 C 0.1668(3) 0.3102(3) 0.2388(3) 0.0286(7) Uani 1 1 d . . . N51 N 0.1359(3) 0.2101(2) 0.1561(3) 0.0347(7) Uani 1 1 d . . . H51A H 0.0682 0.1524 0.1326 0.042 Uiso 1 1 calc R . . H51B H 0.1826 0.2004 0.1239 0.042 Uiso 1 1 calc R . . C61 C 0.2809(3) 0.4066(3) 0.2794(3) 0.0295(7) Uani 1 1 d . . . C611 C 0.3634(3) 0.3956(3) 0.2275(3) 0.0305(7) Uani 1 1 d D . . C621 C 0.3257(3) 0.3888(3) 0.1138(3) 0.0314(7) Uani 1 1 d D . . C631 C 0.4056(3) 0.3825(3) 0.0678(3) 0.0357(8) Uani 1 1 d D . . C641 C 0.5220(4) 0.3842(3) 0.1360(4) 0.0407(9) Uani 1 1 d D . . H641 H 0.5768 0.3815 0.1052 0.049 Uiso 1 1 calc R . . C651 C 0.5603(4) 0.3898(3) 0.2484(3) 0.0401(9) Uani 1 1 d D . . H651 H 0.6407 0.3899 0.2941 0.048 Uiso 1 1 calc R . . C661 C 0.4812(3) 0.3953(3) 0.2956(3) 0.0359(8) Uani 1 1 d D . . H661 H 0.5072 0.3988 0.3730 0.043 Uiso 1 1 calc R . . N12 N 0.1403(4) 0.8627(3) 0.1646(3) 0.0323(9) Uani 0.80 1 d PD A 1 N22 N 0.2180(5) 0.9554(4) 0.1712(4) 0.0320(8) Uani 0.80 1 d PD A 1 H22 H 0.1898 0.9757 0.1123 0.038 Uiso 0.80 1 calc PR A 1 C32 C 0.3359(5) 1.0185(4) 0.2623(4) 0.0238(8) Uani 0.80 1 d PD A 1 N42 N 0.3857(5) 0.9947(4) 0.3562(4) 0.0281(7) Uani 0.80 1 d PD A 1 C52 C 0.3120(5) 0.9030(4) 0.3534(4) 0.0293(9) Uani 0.80 1 d PD A 1 C62 C 0.1843(4) 0.8375(4) 0.2540(4) 0.0282(9) Uani 0.80 1 d PD A 1 N52 N 0.3577(5) 0.8756(4) 0.4436(4) 0.0343(9) Uani 0.80 1 d P A 1 H52A H 0.4345 0.9170 0.5034 0.041 Uiso 0.80 1 calc PR A 1 H52B H 0.3114 0.8160 0.4440 0.041 Uiso 0.80 1 calc PR A 1 N32 N 0.4032(9) 1.1043(6) 0.2528(8) 0.0276(12) Uani 0.80 1 d P A 1 H32A H 0.4816 1.1461 0.3089 0.033 Uiso 0.80 1 calc PR A 1 H32B H 0.3690 1.1188 0.1904 0.033 Uiso 0.80 1 calc PR A 1 C612 C 0.1038(4) 0.7331(4) 0.2472(4) 0.0316(9) Uani 0.80 1 d PD A 1 C622 C 0.0356(4) 0.7411(4) 0.3056(4) 0.0358(11) Uani 0.80 1 d PD A 1 C632 C -0.0451(6) 0.6415(5) 0.2921(6) 0.0489(11) Uani 0.80 1 d PD A 1 C642 C -0.0557(5) 0.5358(5) 0.2221(5) 0.0551(15) Uani 0.80 1 d PD A 1 H642 H -0.1117 0.4680 0.2119 0.066 Uiso 0.80 1 calc PR A 1 C652 C 0.0133(5) 0.5268(5) 0.1668(5) 0.0508(13) Uani 0.80 1 d PD A 1 H652 H 0.0087 0.4530 0.1239 0.061 Uiso 0.80 1 calc PR A 1 C662 C 0.0918(14) 0.6256(11) 0.1723(14) 0.073(5) Uani 0.80 1 d PD A 1 H662 H 0.1336 0.6197 0.1282 0.088 Uiso 0.80 1 calc PR A 1 Cl12 Cl 0.05143(15) 0.87395(13) 0.39328(13) 0.0490(4) Uani 0.80 1 d P A 1 Cl22 Cl -0.13528(14) 0.64747(17) 0.35730(14) 0.0714(5) Uani 0.80 1 d P A 1 C617 C 0.0888(12) 0.8042(11) 0.3079(12) 0.0316(9) Uani 0.20 1 d PGD B 2 C627 C 0.0356(15) 0.6853(11) 0.2632(13) 0.0358(11) Uani 0.20 1 d PG B 2 C637 C -0.0518(17) 0.6356(9) 0.2888(17) 0.0489(11) Uani 0.20 1 d PG B 2 C647 C -0.0860(14) 0.7047(13) 0.3593(15) 0.0551(15) Uani 0.20 1 d PG B 2 H647 H -0.1457 0.6707 0.3768 0.066 Uiso 0.20 1 calc PR B 2 C657 C -0.0328(14) 0.8235(12) 0.4040(13) 0.0508(13) Uani 0.20 1 d PG B 2 H657 H -0.0561 0.8708 0.4522 0.061 Uiso 0.20 1 calc PR B 2 C667 C 0.0546(15) 0.8733(9) 0.3784(15) 0.073(5) Uani 0.20 1 d PG B 2 H667 H 0.0909 0.9545 0.4089 0.088 Uiso 0.20 1 calc PR B 2 Cl17 Cl 0.0927(12) 0.6142(10) 0.1859(13) 0.045(2) Uani 0.20 1 d P B 2 Cl27 Cl -0.1135(8) 0.4891(8) 0.2278(12) 0.137(5) Uani 0.20 1 d P B 2 N17 N 0.1370(18) 0.8950(12) 0.1948(14) 0.0323(9) Uani 0.20 1 d PD B 2 N27 N 0.2061(15) 0.9589(12) 0.1620(13) 0.0320(8) Uani 0.20 1 d PD B 2 H27 H 0.1710 0.9691 0.0969 0.038 Uiso 0.20 1 calc PR B 2 C37 C 0.3347(15) 1.0059(12) 0.2389(13) 0.0238(8) Uani 0.20 1 d PRD B 2 N47 N 0.3855(15) 0.9866(12) 0.3402(13) 0.0281(7) Uani 0.20 1 d PRD B 2 C57 C 0.3077(15) 0.9202(12) 0.3647(13) 0.0293(9) Uani 0.20 1 d PRD B 2 C67 C 0.1791(15) 0.8732(12) 0.2878(13) 0.0282(9) Uani 0.20 1 d PRD B 2 N57 N 0.3505(15) 0.8951(12) 0.4556(13) 0.0343(9) Uani 0.20 1 d PRD B 2 H57A H 0.2984 0.8500 0.4661 0.041 Uiso 0.20 1 calc PR B 2 H57B H 0.4313 0.9231 0.5063 0.041 Uiso 0.20 1 calc PR B 2 N37 N 0.409(4) 1.081(3) 0.236(4) 0.0276(12) Uani 0.20 1 d PD B 2 H37A H 0.3808 1.1089 0.1835 0.033 Uiso 0.20 1 calc PR B 2 H37B H 0.4892 1.1076 0.2877 0.033 Uiso 0.20 1 calc PR B 2 O13 O 0.1039(2) 0.9643(2) 0.9656(2) 0.0392(6) Uani 1 1 d . . . O23 O 0.2705(2) 1.1182(2) 1.0350(2) 0.0372(6) Uani 1 1 d . . . O33 O 0.3094(2) 0.7369(2) 0.5608(2) 0.0343(6) Uani 1 1 d . . . O43 O 0.1651(2) 0.6720(2) 0.6035(2) 0.0391(6) Uani 1 1 d . . . C13 C 0.1680(3) 1.0419(3) 0.9524(3) 0.0285(7) Uani 1 1 d . . . C23 C 0.1145(3) 1.0436(3) 0.8312(3) 0.0319(7) Uani 1 1 d . . . H23A H 0.1097 1.1196 0.8395 0.038 Uiso 1 1 calc R . . H23B H 0.0285 0.9848 0.7785 0.038 Uiso 1 1 calc R . . C33 C 0.1935(4) 1.0200(3) 0.7740(3) 0.0354(8) Uani 1 1 d . . . H33A H 0.1741 1.0486 0.7116 0.042 Uiso 1 1 calc R . . H33B H 0.2829 1.0637 0.8351 0.042 Uiso 1 1 calc R . . C43 C 0.1725(3) 0.8941(3) 0.7190(3) 0.0338(8) Uani 1 1 d . . . H43A H 0.0867 0.8519 0.6495 0.041 Uiso 1 1 calc R . . H43B H 0.1797 0.8622 0.7777 0.041 Uiso 1 1 calc R . . C53 C 0.2655(3) 0.8752(3) 0.6794(3) 0.0345(8) Uani 1 1 d . . . H53A H 0.2664 0.9176 0.6304 0.041 Uiso 1 1 calc R . . H53B H 0.3498 0.9100 0.7510 0.041 Uiso 1 1 calc R . . C63 C 0.2425(3) 0.7518(3) 0.6091(3) 0.0291(7) Uani 1 1 d . . . O14 O 0.7685(15) 0.8380(14) 0.5382(16) 0.137(4) Uani 0.40 1 d PD C 1 C24 C 0.684(3) 0.831(2) 0.4235(17) 0.109(6) Uani 0.40 1 d PD C 1 H24A H 0.7195 0.8198 0.3709 0.130 Uiso 0.40 1 calc PR C 1 H24B H 0.6643 0.9009 0.4323 0.130 Uiso 0.40 1 calc PR C 1 C34 C 0.568(3) 0.727(2) 0.375(2) 0.075(4) Uani 0.40 1 d PD C 1 H34A H 0.4963 0.7490 0.3691 0.090 Uiso 0.40 1 calc PR C 1 H34B H 0.5445 0.6701 0.2958 0.090 Uiso 0.40 1 calc PR C 1 C44 C 0.611(3) 0.6813(12) 0.4673(17) 0.105(4) Uani 0.40 1 d PD C 1 H44A H 0.5386 0.6393 0.4704 0.126 Uiso 0.40 1 calc PR C 1 H44B H 0.6514 0.6280 0.4480 0.126 Uiso 0.40 1 calc PR C 1 C54 C 0.6982(11) 0.7784(11) 0.5797(11) 0.0564(19) Uani 0.40 1 d PD C 1 H54A H 0.7505 0.7560 0.6401 0.068 Uiso 0.40 1 calc PR C 1 H54B H 0.6566 0.8237 0.6108 0.068 Uiso 0.40 1 calc PR C 1 O18 O 0.7446(10) 0.8744(9) 0.4894(12) 0.137(4) Uani 0.60 1 d PD D 2 C28 C 0.6276(18) 0.8226(13) 0.3820(10) 0.109(6) Uani 0.60 1 d PD D 2 H28A H 0.6388 0.8226 0.3143 0.130 Uiso 0.60 1 calc PR D 2 H28B H 0.5719 0.8638 0.3880 0.130 Uiso 0.60 1 calc PR D 2 C38 C 0.5746(18) 0.7013(13) 0.3666(13) 0.075(4) Uani 0.60 1 d PD D 2 H38A H 0.4821 0.6707 0.3247 0.090 Uiso 0.60 1 calc PR D 2 H38B H 0.6025 0.6490 0.3236 0.090 Uiso 0.60 1 calc PR D 2 C48 C 0.6307(14) 0.7203(7) 0.4948(10) 0.105(4) Uani 0.60 1 d PD D 2 H48A H 0.5837 0.7517 0.5302 0.126 Uiso 0.60 1 calc PR D 2 H48B H 0.6312 0.6478 0.5024 0.126 Uiso 0.60 1 calc PR D 2 C58 C 0.7594(8) 0.8043(8) 0.5526(8) 0.0564(19) Uani 0.60 1 d PD D 2 H58A H 0.7925 0.8502 0.6382 0.068 Uiso 0.60 1 calc PR D 2 H58B H 0.8162 0.7655 0.5439 0.068 Uiso 0.60 1 calc PR D 2 C55 C 0.2461(10) 0.7240(10) 0.0263(9) 0.058(3) Uani 0.50 1 d PD E 1 H55C H 0.1761 0.7400 0.0335 0.069 Uiso 0.50 1 calc PR E 1 H55D H 0.2239 0.6399 -0.0066 0.069 Uiso 0.50 1 calc PR E 1 O15 O 0.3578(8) 0.7794(10) 0.1394(8) 0.098(3) Uani 0.50 1 d PD E 1 C25 C 0.4601(5) 0.8332(5) 0.1275(6) 0.0825(18) Uani 0.50 1 d PD E 1 H25A H 0.5035 0.7808 0.1139 0.099 Uiso 0.50 1 calc PR E 1 H25B H 0.5211 0.9046 0.2000 0.099 Uiso 0.50 1 calc PR E 1 C35 C 0.4011(8) 0.8600(5) 0.0203(6) 0.097(2) Uani 0.50 1 d PD E 1 H35C H 0.4005 0.9384 0.0452 0.117 Uiso 0.50 1 calc PR E 1 H35D H 0.4468 0.8530 -0.0236 0.117 Uiso 0.50 1 calc PR E 1 C45 C 0.2709(7) 0.7714(5) -0.0542(5) 0.0870(19) Uani 0.50 1 d PD E 1 H45A H 0.2633 0.7093 -0.1219 0.104 Uiso 0.50 1 calc PR E 1 H45B H 0.2103 0.8065 -0.0858 0.104 Uiso 0.50 1 calc PR E 1 O16 O 0.2817(8) 0.6785(8) -0.0188(10) 0.104(4) Uani 0.50 1 d P F 2 C26 C 0.3582(10) 0.7161(9) 0.0870(9) 0.049(2) Uani 0.50 1 d P F 2 H26A H 0.3980 0.6606 0.1013 0.059 Uiso 0.50 1 calc PR F 2 H26B H 0.3158 0.7268 0.1338 0.059 Uiso 0.50 1 calc PR F 2 C36 C 0.4601(5) 0.8332(5) 0.1275(6) 0.0825(18) Uani 0.50 1 d P F 2 H36A H 0.4735 0.8928 0.2004 0.099 Uiso 0.50 1 calc PR F 2 H36B H 0.5405 0.8257 0.1414 0.099 Uiso 0.50 1 calc PR F 2 C46 C 0.4011(8) 0.8600(5) 0.0203(6) 0.097(2) Uani 0.50 1 d P F 2 H46A H 0.4005 0.9384 0.0452 0.117 Uiso 0.50 1 calc PR F 2 H46B H 0.4468 0.8530 -0.0236 0.117 Uiso 0.50 1 calc PR F 2 C56 C 0.2709(7) 0.7714(5) -0.0542(5) 0.0870(19) Uani 0.50 1 d P F 2 H56A H 0.2121 0.8017 -0.0373 0.104 Uiso 0.50 1 calc PR F 2 H56B H 0.2420 0.7456 -0.1399 0.104 Uiso 0.50 1 calc PR F 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 0.0373(5) 0.0660(7) 0.0383(5) 0.0265(5) 0.0189(4) 0.0244(5) Cl21 0.0576(6) 0.0693(7) 0.0392(5) 0.0276(5) 0.0314(5) 0.0231(5) N11 0.0294(15) 0.0348(16) 0.0304(15) 0.0095(13) 0.0186(12) 0.0071(12) N21 0.0311(15) 0.0310(15) 0.0301(14) 0.0050(12) 0.0200(12) 0.0060(12) C31 0.0294(17) 0.0320(18) 0.0307(17) 0.0142(15) 0.0175(14) 0.0111(14) N31 0.0380(16) 0.0326(16) 0.0427(17) 0.0098(14) 0.0295(15) 0.0087(13) N41 0.0285(14) 0.0294(15) 0.0309(14) 0.0102(12) 0.0174(12) 0.0075(12) C51 0.0271(16) 0.0307(18) 0.0249(16) 0.0099(14) 0.0132(13) 0.0084(14) N51 0.0338(16) 0.0290(15) 0.0330(15) 0.0043(13) 0.0201(13) 0.0030(12) C61 0.0257(16) 0.0303(18) 0.0262(16) 0.0073(14) 0.0136(14) 0.0052(14) C611 0.0336(18) 0.0264(17) 0.0309(17) 0.0101(14) 0.0190(15) 0.0081(14) C621 0.0277(17) 0.0295(18) 0.0310(17) 0.0098(14) 0.0133(14) 0.0077(14) C631 0.042(2) 0.0340(19) 0.0331(18) 0.0135(16) 0.0221(16) 0.0126(16) C641 0.043(2) 0.043(2) 0.050(2) 0.0218(19) 0.0320(19) 0.0181(18) C651 0.0332(19) 0.048(2) 0.047(2) 0.0238(19) 0.0232(17) 0.0176(17) C661 0.0272(17) 0.0331(19) 0.043(2) 0.0114(16) 0.0183(16) 0.0104(15) N12 0.0296(16) 0.031(2) 0.025(2) 0.0094(19) 0.0097(17) 0.0027(18) N22 0.0278(17) 0.0368(17) 0.0243(15) 0.0177(13) 0.0074(13) 0.0049(13) C32 0.0296(17) 0.0259(19) 0.015(2) 0.0044(16) 0.0141(16) 0.0085(15) N42 0.0279(14) 0.0295(16) 0.0229(17) 0.0112(14) 0.0119(13) 0.0057(12) C52 0.0255(17) 0.030(2) 0.0288(19) 0.0115(17) 0.0134(15) 0.0074(16) C62 0.0259(18) 0.031(3) 0.022(2) 0.009(2) 0.0114(17) 0.0049(18) N52 0.0247(15) 0.038(2) 0.0328(18) 0.0197(17) 0.0088(13) 0.0042(15) N32 0.0292(18) 0.025(4) 0.026(3) 0.011(3) 0.0132(18) 0.008(2) C612 0.0248(19) 0.034(2) 0.028(2) 0.0159(19) 0.0069(16) 0.0059(18) C622 0.031(2) 0.045(3) 0.027(2) 0.019(2) 0.0104(19) 0.011(2) C632 0.031(2) 0.065(3) 0.045(2) 0.035(2) 0.0116(18) 0.007(2) C642 0.033(3) 0.055(4) 0.058(3) 0.038(3) 0.008(2) -0.006(3) C652 0.045(3) 0.040(3) 0.049(3) 0.018(2) 0.012(2) 0.008(2) C662 0.051(6) 0.052(7) 0.069(7) 0.037(5) -0.007(4) 0.000(5) Cl12 0.0565(8) 0.0594(9) 0.0402(7) 0.0234(6) 0.0291(6) 0.0255(7) Cl22 0.0463(8) 0.1165(14) 0.0610(9) 0.0536(10) 0.0320(7) 0.0150(8) C617 0.0248(19) 0.034(2) 0.028(2) 0.0159(19) 0.0069(16) 0.0059(18) C627 0.031(2) 0.045(3) 0.027(2) 0.019(2) 0.0104(19) 0.011(2) C637 0.031(2) 0.065(3) 0.045(2) 0.035(2) 0.0116(18) 0.007(2) C647 0.033(3) 0.055(4) 0.058(3) 0.038(3) 0.008(2) -0.006(3) C657 0.045(3) 0.040(3) 0.049(3) 0.018(2) 0.012(2) 0.008(2) C667 0.051(6) 0.052(7) 0.069(7) 0.037(5) -0.007(4) 0.000(5) Cl17 0.039(5) 0.039(5) 0.050(4) 0.012(4) 0.019(4) 0.019(4) Cl27 0.060(5) 0.082(6) 0.214(12) 0.103(8) 0.009(6) -0.002(4) N17 0.0296(16) 0.031(2) 0.025(2) 0.0094(19) 0.0097(17) 0.0027(18) N27 0.0278(17) 0.0368(17) 0.0243(15) 0.0177(13) 0.0074(13) 0.0049(13) C37 0.0296(17) 0.0259(19) 0.015(2) 0.0044(16) 0.0141(16) 0.0085(15) N47 0.0279(14) 0.0295(16) 0.0229(17) 0.0112(14) 0.0119(13) 0.0057(12) C57 0.0255(17) 0.030(2) 0.0288(19) 0.0115(17) 0.0134(15) 0.0074(16) C67 0.0259(18) 0.031(3) 0.022(2) 0.009(2) 0.0114(17) 0.0049(18) N57 0.0247(15) 0.038(2) 0.0328(18) 0.0197(17) 0.0088(13) 0.0042(15) N37 0.0292(18) 0.025(4) 0.026(3) 0.011(3) 0.0132(18) 0.008(2) O13 0.0354(13) 0.0409(15) 0.0277(12) 0.0161(11) 0.0098(11) 0.0009(11) O23 0.0370(14) 0.0330(14) 0.0300(13) 0.0120(11) 0.0130(11) 0.0030(11) O33 0.0416(14) 0.0323(13) 0.0368(13) 0.0138(11) 0.0278(12) 0.0125(11) O43 0.0411(14) 0.0308(13) 0.0474(15) 0.0105(12) 0.0309(13) 0.0080(11) C13 0.0323(17) 0.0277(17) 0.0273(16) 0.0096(14) 0.0177(14) 0.0118(14) C23 0.0402(19) 0.0350(19) 0.0285(17) 0.0153(15) 0.0206(15) 0.0192(16) C33 0.044(2) 0.035(2) 0.0340(18) 0.0167(16) 0.0251(17) 0.0147(16) C43 0.0381(19) 0.0339(19) 0.0351(18) 0.0143(15) 0.0237(16) 0.0135(16) C53 0.0369(19) 0.0321(19) 0.0359(19) 0.0113(15) 0.0230(16) 0.0100(15) C63 0.0273(16) 0.0327(18) 0.0247(16) 0.0113(14) 0.0126(13) 0.0097(14) O14 0.133(7) 0.091(7) 0.177(10) 0.089(6) 0.063(7) 0.016(5) C24 0.192(18) 0.060(5) 0.037(8) 0.023(7) 0.035(9) 0.024(9) C34 0.090(5) 0.049(8) 0.061(4) 0.024(5) 0.019(3) 0.022(5) C44 0.191(10) 0.011(6) 0.046(7) -0.003(6) 0.039(7) -0.015(7) C54 0.052(4) 0.062(5) 0.047(4) 0.024(3) 0.017(3) 0.025(4) O18 0.133(7) 0.091(7) 0.177(10) 0.089(6) 0.063(7) 0.016(5) C28 0.192(18) 0.060(5) 0.037(8) 0.023(7) 0.035(9) 0.024(9) C38 0.090(5) 0.049(8) 0.061(4) 0.024(5) 0.019(3) 0.022(5) C48 0.191(10) 0.011(6) 0.046(7) -0.003(6) 0.039(7) -0.015(7) C58 0.052(4) 0.062(5) 0.047(4) 0.024(3) 0.017(3) 0.025(4) C55 0.064(7) 0.060(7) 0.053(6) 0.027(5) 0.032(5) 0.019(5) O15 0.074(6) 0.107(8) 0.090(7) 0.049(6) 0.032(5) 0.004(6) C25 0.054(3) 0.062(3) 0.113(5) 0.023(3) 0.040(3) 0.015(3) C35 0.167(7) 0.046(3) 0.114(5) 0.032(3) 0.104(5) 0.035(4) C45 0.119(5) 0.068(4) 0.077(4) 0.041(3) 0.043(4) 0.039(4) O16 0.055(5) 0.073(6) 0.121(9) 0.051(6) -0.001(5) -0.008(4) C26 0.057(6) 0.052(6) 0.044(5) 0.016(5) 0.031(5) 0.026(5) C36 0.054(3) 0.062(3) 0.113(5) 0.023(3) 0.040(3) 0.015(3) C46 0.167(7) 0.046(3) 0.114(5) 0.032(3) 0.104(5) 0.035(4) C56 0.119(5) 0.068(4) 0.077(4) 0.041(3) 0.043(4) 0.039(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 1.728(3) . ? Cl21 C631 1.729(4) . ? N11 C61 1.294(4) . ? N11 N21 1.356(4) . ? N21 C31 1.363(4) . ? N21 H21 0.8800 . ? C31 N31 1.320(4) . ? C31 N41 1.332(4) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N41 C51 1.332(4) . ? C51 N51 1.307(4) . ? C51 C61 1.473(5) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C61 C611 1.493(4) . ? C611 C621 1.390(5) . ? C611 C661 1.398(5) . ? C621 C631 1.399(5) . ? C631 C641 1.373(5) . ? C641 C651 1.378(5) . ? C641 H641 0.9500 . ? C651 C661 1.402(5) . ? C651 H651 0.9500 . ? C661 H661 0.9500 . ? N12 C62 1.290(5) . ? N12 N22 1.352(5) . ? N22 C32 1.348(5) . ? N22 H22 0.8800 . ? C32 N42 1.337(5) . ? C32 N32 1.340(11) . ? N42 C52 1.344(5) . ? C52 N52 1.319(5) . ? C52 C62 1.458(6) . ? C62 C612 1.484(6) . ? N52 H52A 0.8800 . ? N52 H52B 0.8800 . ? N32 H32A 0.8800 . ? N32 H32B 0.8800 . ? C612 C622 1.398(6) . ? C612 C662 1.414(13) . ? C622 C632 1.393(7) . ? C622 Cl12 1.719(5) . ? C632 C642 1.378(8) . ? C632 Cl22 1.716(6) . ? C642 C652 1.374(8) . ? C642 H642 0.9500 . ? C652 C662 1.424(14) . ? C652 H652 0.9500 . ? C662 H662 0.9500 . ? C617 C627 1.3900 . ? C617 C667 1.3900 . ? C617 C67 1.479(19) . ? C627 C637 1.3900 . ? C627 Cl17 1.686(15) . ? C637 C647 1.3900 . ? C637 Cl27 1.706(14) . ? C647 C657 1.3900 . ? C647 H647 0.9500 . ? C657 C667 1.3900 . ? C657 H657 0.9500 . ? C667 H667 0.9500 . ? N17 C67 1.303(14) . ? N17 N27 1.383(14) . ? N27 C37 1.3900 . ? N27 H27 0.8800 . ? C37 N37 1.23(5) . ? C37 N47 1.3900 . ? N47 C57 1.3900 . ? C57 N57 1.3048 . ? C57 C67 1.3900 . ? N57 H57A 0.8800 . ? N57 H57B 0.8800 . ? N37 H37A 0.8800 . ? N37 H37B 0.8800 . ? O13 C13 1.272(4) . ? O23 C13 1.246(4) . ? O33 C63 1.283(4) . ? O43 C63 1.239(4) . ? C13 C23 1.516(4) . ? C23 C33 1.531(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C33 C43 1.515(5) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C43 C53 1.521(5) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C53 C63 1.516(5) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? O14 C24 1.447(16) . ? O14 C54 1.454(15) . ? C24 C34 1.513(16) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C34 C44 1.503(15) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C44 C54 1.439(13) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? O18 C28 1.419(13) . ? O18 C58 1.426(11) . ? C28 C38 1.511(13) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C38 C48 1.507(12) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C48 C58 1.478(13) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C58 H58A 0.9900 . ? C58 H58B 0.9900 . ? C55 O15 1.424(12) . ? C55 C45 1.516(10) . ? C55 H55C 0.9900 . ? C55 H55D 0.9900 . ? O15 C25 1.439(9) . ? C25 C35 1.527(9) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C35 C45 1.496(9) . ? C35 H35C 0.9900 . ? C35 H35D 0.9900 . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? O16 C26 1.223(14) . ? C26 H26A 0.9900 . ? C26 H26B 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 C61 N11 N21 117.5(3) . . ? N11 N21 C31 122.1(3) . . ? N11 N21 H21 119.0 . . ? C31 N21 H21 119.0 . . ? N31 C31 N41 120.5(3) . . ? N31 C31 N21 116.9(3) . . ? N41 C31 N21 122.6(3) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C31 N41 C51 117.1(3) . . ? N51 C51 N41 119.9(3) . . ? N51 C51 C61 120.1(3) . . ? N41 C51 C61 120.0(3) . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? N11 C61 C51 120.7(3) . . ? N11 C61 C611 116.9(3) . . ? C51 C61 C611 122.4(3) . . ? C621 C611 C661 119.8(3) . . ? C621 C611 C61 120.8(3) . . ? C661 C611 C61 119.4(3) . . ? C611 C621 C631 120.2(3) . . ? C611 C621 Cl11 119.8(3) . . ? C631 C621 Cl11 119.9(3) . . ? C641 C631 C621 119.7(3) . . ? C641 C631 Cl21 120.3(3) . . ? C621 C631 Cl21 120.0(3) . . ? C631 C641 C651 120.8(3) . . ? C631 C641 H641 119.6 . . ? C651 C641 H641 119.6 . . ? C641 C651 C661 120.3(4) . . ? C641 C651 H651 119.9 . . ? C661 C651 H651 119.9 . . ? C611 C661 C651 119.1(3) . . ? C611 C661 H661 120.4 . . ? C651 C661 H661 120.4 . . ? C62 N12 N22 115.9(4) . . ? C32 N22 N12 124.1(4) . . ? C32 N22 H22 118.0 . . ? N12 N22 H22 118.0 . . ? N42 C32 N32 121.1(5) . . ? N42 C32 N22 122.0(4) . . ? N32 C32 N22 116.8(5) . . ? C32 N42 C52 116.1(3) . . ? N52 C52 N42 118.2(4) . . ? N52 C52 C62 121.4(4) . . ? N42 C52 C62 120.4(4) . . ? N12 C62 C52 121.5(4) . . ? N12 C62 C612 117.4(4) . . ? C52 C62 C612 121.0(4) . . ? C52 N52 H52A 120.0 . . ? C52 N52 H52B 120.0 . . ? H52A N52 H52B 120.0 . . ? C32 N32 H32A 120.0 . . ? C32 N32 H32B 120.0 . . ? H32A N32 H32B 120.0 . . ? C622 C612 C662 121.6(7) . . ? C622 C612 C62 121.0(4) . . ? C662 C612 C62 117.3(7) . . ? C632 C622 C612 119.9(5) . . ? C632 C622 Cl12 120.4(4) . . ? C612 C622 Cl12 119.7(4) . . ? C642 C632 C622 119.5(6) . . ? C642 C632 Cl22 119.1(4) . . ? C622 C632 Cl22 121.4(5) . . ? C652 C642 C632 121.1(5) . . ? C652 C642 H642 119.4 . . ? C632 C642 H642 119.4 . . ? C642 C652 C662 121.5(7) . . ? C642 C652 H652 119.2 . . ? C662 C652 H652 119.2 . . ? C612 C662 C652 116.1(11) . . ? C612 C662 H662 122.0 . . ? C652 C662 H662 122.0 . . ? C627 C617 C667 120.0 . . ? C627 C617 C67 128.4(10) . . ? C667 C617 C67 111.6(10) . . ? C637 C627 C617 120.0 . . ? C637 C627 Cl17 125.8(10) . . ? C617 C627 Cl17 114.1(10) . . ? C647 C637 C627 120.0 . . ? C647 C637 Cl27 123.5(10) . . ? C627 C637 Cl27 116.4(10) . . ? C637 C647 C657 120.0 . . ? C637 C647 H647 120.0 . . ? C657 C647 H647 120.0 . . ? C667 C657 C647 120.0 . . ? C667 C657 H657 120.0 . . ? C647 C657 H657 120.0 . . ? C657 C667 C617 120.0 . . ? C657 C667 H667 120.0 . . ? C617 C667 H667 120.0 . . ? C67 N17 N27 127.4(13) . . ? N17 N27 C37 115.5(7) . . ? N17 N27 H27 122.3 . . ? C37 N27 H27 122.3 . . ? N37 C37 N27 124(2) . . ? N37 C37 N47 114(2) . . ? N27 C37 N47 120.0 . . ? C37 N47 C57 120.0 . . ? N57 C57 C67 117.3 . . ? N57 C57 N47 122.7 . . ? C67 C57 N47 120.0 . . ? N17 C67 C57 117.2(7) . . ? N17 C67 C617 118.9(12) . . ? C57 C67 C617 123.9(8) . . ? C57 N57 H57A 120.0 . . ? C57 N57 H57B 120.0 . . ? H57A N57 H57B 120.0 . . ? C37 N37 H37A 120.0 . . ? C37 N37 H37B 120.0 . . ? H37A N37 H37B 120.0 . . ? O23 C13 O13 123.2(3) . . ? O23 C13 C23 118.7(3) . . ? O13 C13 C23 118.1(3) . . ? C13 C23 C33 112.2(3) . . ? C13 C23 H23A 109.2 . . ? C33 C23 H23A 109.2 . . ? C13 C23 H23B 109.2 . . ? C33 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C43 C33 C23 113.8(3) . . ? C43 C33 H33A 108.8 . . ? C23 C33 H33A 108.8 . . ? C43 C33 H33B 108.8 . . ? C23 C33 H33B 108.8 . . ? H33A C33 H33B 107.7 . . ? C33 C43 C53 112.5(3) . . ? C33 C43 H43A 109.1 . . ? C53 C43 H43A 109.1 . . ? C33 C43 H43B 109.1 . . ? C53 C43 H43B 109.1 . . ? H43A C43 H43B 107.8 . . ? C63 C53 C43 116.6(3) . . ? C63 C53 H53A 108.1 . . ? C43 C53 H53A 108.1 . . ? C63 C53 H53B 108.1 . . ? C43 C53 H53B 108.1 . . ? H53A C53 H53B 107.3 . . ? O43 C63 O33 123.6(3) . . ? O43 C63 C53 120.0(3) . . ? O33 C63 C53 116.3(3) . . ? C24 O14 C54 109.8(13) . . ? O14 C24 C34 103.9(12) . . ? O14 C24 H24A 111.0 . . ? C34 C24 H24A 111.0 . . ? O14 C24 H24B 111.0 . . ? C34 C24 H24B 111.0 . . ? H24A C24 H24B 109.0 . . ? C44 C34 C24 101.6(13) . . ? C44 C34 H34A 111.5 . . ? C24 C34 H34A 111.5 . . ? C44 C34 H34B 111.5 . . ? C24 C34 H34B 111.5 . . ? H34A C34 H34B 109.3 . . ? C54 C44 C34 107.2(13) . . ? C54 C44 H44A 110.3 . . ? C34 C44 H44A 110.3 . . ? C54 C44 H44B 110.3 . . ? C34 C44 H44B 110.3 . . ? H44A C44 H44B 108.5 . . ? C44 C54 O14 97.1(12) . . ? C44 C54 H54A 112.3 . . ? O14 C54 H54A 112.3 . . ? C44 C54 H54B 112.3 . . ? O14 C54 H54B 112.3 . . ? H54A C54 H54B 109.9 . . ? C28 O18 C58 111.9(8) . . ? O18 C28 C38 104.7(10) . . ? O18 C28 H28A 110.8 . . ? C38 C28 H28A 110.8 . . ? O18 C28 H28B 110.8 . . ? C38 C28 H28B 110.8 . . ? H28A C28 H28B 108.9 . . ? C48 C38 C28 100.3(9) . . ? C48 C38 H38A 111.7 . . ? C28 C38 H38A 111.7 . . ? C48 C38 H38B 111.7 . . ? C28 C38 H38B 111.7 . . ? H38A C38 H38B 109.5 . . ? C58 C48 C38 103.9(10) . . ? C58 C48 H48A 111.0 . . ? C38 C48 H48A 111.0 . . ? C58 C48 H48B 111.0 . . ? C38 C48 H48B 111.0 . . ? H48A C48 H48B 109.0 . . ? O18 C58 C48 102.9(8) . . ? O18 C58 H58A 111.2 . . ? C48 C58 H58A 111.2 . . ? O18 C58 H58B 111.2 . . ? C48 C58 H58B 111.2 . . ? H58A C58 H58B 109.1 . . ? O15 C55 C45 107.0(7) . . ? O15 C55 H55C 110.3 . . ? C45 C55 H55C 110.3 . . ? O15 C55 H55D 110.3 . . ? C45 C55 H55D 110.3 . . ? H55C C55 H55D 108.6 . . ? C55 O15 C25 109.4(8) . . ? O15 C25 C35 105.4(6) . . ? O15 C25 H25A 110.7 . . ? C35 C25 H25A 110.7 . . ? O15 C25 H25B 110.7 . . ? C35 C25 H25B 110.7 . . ? H25A C25 H25B 108.8 . . ? C45 C35 C25 103.8(4) . . ? C45 C35 H35C 111.0 . . ? C25 C35 H35C 111.0 . . ? C45 C35 H35D 111.0 . . ? C25 C35 H35D 111.0 . . ? H35C C35 H35D 109.0 . . ? C35 C45 C55 106.5(6) . . ? C35 C45 H45A 110.4 . . ? C55 C45 H45A 110.4 . . ? C35 C45 H45B 110.4 . . ? C55 C45 H45B 110.4 . . ? H45A C45 H45B 108.6 . . ? O16 C26 H26A 109.7 . . ? O16 C26 H26B 109.7 . . ? H26A C26 H26B 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 C61 N11 N21 C31 -0.9(5) . . . . ? N11 N21 C31 N31 179.0(3) . . . . ? N11 N21 C31 N41 -0.3(5) . . . . ? N31 C31 N41 C51 -177.6(3) . . . . ? N21 C31 N41 C51 1.7(5) . . . . ? C31 N41 C51 N51 177.3(3) . . . . ? C31 N41 C51 C61 -1.9(5) . . . . ? N21 N11 C61 C51 0.6(5) . . . . ? N21 N11 C61 C611 -179.1(3) . . . . ? N51 C51 C61 N11 -178.4(3) . . . . ? N41 C51 C61 N11 0.8(5) . . . . ? N51 C51 C61 C611 1.3(5) . . . . ? N41 C51 C61 C611 -179.5(3) . . . . ? N11 C61 C611 C621 -107.8(4) . . . . ? C51 C61 C611 C621 72.5(5) . . . . ? N11 C61 C611 C661 70.6(4) . . . . ? C51 C61 C611 C661 -109.1(4) . . . . ? C661 C611 C621 C631 -0.5(5) . . . . ? C61 C611 C621 C631 177.8(3) . . . . ? C661 C611 C621 Cl11 -179.6(3) . . . . ? C61 C611 C621 Cl11 -1.3(5) . . . . ? C611 C621 C631 C641 -0.6(5) . . . . ? Cl11 C621 C631 C641 178.5(3) . . . . ? C611 C621 C631 Cl21 178.5(3) . . . . ? Cl11 C621 C631 Cl21 -2.4(4) . . . . ? C621 C631 C641 C651 1.2(6) . . . . ? Cl21 C631 C641 C651 -177.9(3) . . . . ? C631 C641 C651 C661 -0.8(6) . . . . ? C621 C611 C661 C651 1.0(5) . . . . ? C61 C611 C661 C651 -177.4(3) . . . . ? C641 C651 C661 C611 -0.3(6) . . . . ? C62 N12 N22 C32 1.5(7) . . . . ? N12 N22 C32 N42 -0.9(7) . . . . ? N12 N22 C32 N32 176.7(5) . . . . ? N32 C32 N42 C52 -176.5(4) . . . . ? N22 C32 N42 C52 1.0(6) . . . . ? C32 N42 C52 N52 179.3(4) . . . . ? C32 N42 C52 C62 -1.7(6) . . . . ? N22 N12 C62 C52 -2.3(6) . . . . ? N22 N12 C62 C612 -177.2(4) . . . . ? N52 C52 C62 N12 -178.6(4) . . . . ? N42 C52 C62 N12 2.5(7) . . . . ? N52 C52 C62 C612 -3.9(7) . . . . ? N42 C52 C62 C612 177.3(4) . . . . ? N12 C62 C612 C622 -100.4(5) . . . . ? C52 C62 C612 C622 84.7(6) . . . . ? N12 C62 C612 C662 74.9(9) . . . . ? C52 C62 C612 C662 -100.0(9) . . . . ? C662 C612 C622 C632 1.1(10) . . . . ? C62 C612 C622 C632 176.1(5) . . . . ? C662 C612 C622 Cl12 -178.7(8) . . . . ? C62 C612 C622 Cl12 -3.6(6) . . . . ? C612 C622 C632 C642 0.8(8) . . . . ? Cl12 C622 C632 C642 -179.5(5) . . . . ? C612 C622 C632 Cl22 -177.4(4) . . . . ? Cl12 C622 C632 Cl22 2.4(7) . . . . ? C622 C632 C642 C652 1.0(9) . . . . ? Cl22 C632 C642 C652 179.1(4) . . . . ? C632 C642 C652 C662 -4.6(11) . . . . ? C622 C612 C662 C652 -4.3(16) . . . . ? C62 C612 C662 C652 -179.6(8) . . . . ? C642 C652 C662 C612 6.1(16) . . . . ? C667 C617 C627 C637 0.0 . . . . ? C67 C617 C627 C637 -177.7(15) . . . . ? C667 C617 C627 Cl17 -176.8(13) . . . . ? C67 C617 C627 Cl17 5.5(19) . . . . ? C617 C627 C637 C647 0.0 . . . . ? Cl17 C627 C637 C647 176.4(14) . . . . ? C617 C627 C637 Cl27 179.0(16) . . . . ? Cl17 C627 C637 Cl27 -4.7(13) . . . . ? C627 C637 C647 C657 0.0 . . . . ? Cl27 C637 C647 C657 -178.9(17) . . . . ? C637 C647 C657 C667 0.0 . . . . ? C647 C657 C667 C617 0.0 . . . . ? C627 C617 C667 C657 0.0 . . . . ? C67 C617 C667 C657 178.0(13) . . . . ? C67 N17 N27 C37 -1.0(9) . . . . ? N17 N27 C37 N37 -166.2(16) . . . . ? N17 N27 C37 N47 0.4(4) . . . . ? N37 C37 N47 C57 167.9(14) . . . . ? N27 C37 N47 C57 0.0 . . . . ? C37 N47 C57 N57 176.9 . . . . ? C37 N47 C57 C67 0.0 . . . . ? N27 N17 C67 C57 1.0(9) . . . . ? N27 N17 C67 C617 179.0(4) . . . . ? N57 C57 C67 N17 -177.5(4) . . . . ? N47 C57 C67 N17 -0.5(4) . . . . ? N57 C57 C67 C617 4.6(9) . . . . ? N47 C57 C67 C617 -178.4(9) . . . . ? C627 C617 C67 N17 86.4(16) . . . . ? C667 C617 C67 N17 -91.5(10) . . . . ? C627 C617 C67 C57 -95.8(13) . . . . ? C667 C617 C67 C57 86.4(9) . . . . ? O23 C13 C23 C33 66.6(4) . . . . ? O13 C13 C23 C33 -115.6(4) . . . . ? C13 C23 C33 C43 78.5(4) . . . . ? C23 C33 C43 C53 -171.5(3) . . . . ? C33 C43 C53 C63 -172.4(3) . . . . ? C43 C53 C63 O43 -12.0(5) . . . . ? C43 C53 C63 O33 169.9(3) . . . . ? C54 O14 C24 C34 -22(3) . . . . ? O14 C24 C34 C44 -6(4) . . . . ? C24 C34 C44 C54 32(4) . . . . ? C34 C44 C54 O14 -44(3) . . . . ? C24 O14 C54 C44 41(2) . . . . ? C58 O18 C28 C38 -10(2) . . . . ? O18 C28 C38 C48 31(2) . . . . ? C28 C38 C48 C58 -40.2(19) . . . . ? C28 O18 C58 C48 -15.2(17) . . . . ? C38 C48 C58 O18 34.6(15) . . . . ? C45 C55 O15 C25 -15.8(13) . . . . ? C55 O15 C25 C35 27.1(11) . . . . ? O15 C25 C35 C45 -27.1(8) . . . . ? C25 C35 C45 C55 17.7(8) . . . . ? O15 C55 C45 C35 -2.1(11) . . . . ? 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 0.88 1.86 2.712(4) 163.8 . N31 H31A O43 0.88 2.04 2.863(4) 154.6 2_566 N31 H31B O43 0.88 1.93 2.810(4) 172.9 . N51 H51A O13 0.88 1.98 2.822(4) 161.0 2_566 N51 H51B O23 0.88 2.17 3.020(4) 160.9 1_544 N22 H22 O13 0.88 1.78 2.626(5) 160.0 1_554 N22 H22 O23 0.88 2.63 3.354(5) 140.0 1_554 N32 H32A O33 0.88 2.32 3.192(10) 172.9 2_676 N32 H32B O23 0.88 1.96 2.832(10) 168.4 1_554 N52 H52A N42 0.88 2.05 2.930(9) 176.8 2_676 N52 H52B O33 0.88 2.15 2.884(5) 140.7 . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.08 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.035 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.071 data_LMPI_BAc _database_code_depnum_ccdc_archive 'CCDC 908275' #TrackingRef '15040_web_deposit_cif_file_2_JuditGalcera_1351546362.LMPI_BAc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - pimelate - n-butyl acetate solvate (2:1:1) ; _chemical_name_common 'Lamotrigine hemipimelate n-butyl acetate solvate' _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C7 H10 O4, C6 H12 O2' _chemical_formula_sum 'C31 H38 Cl4 N10 O6' _chemical_formula_weight 788.51 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.5864(3) _cell_length_b 13.5421(3) _cell_length_c 13.9251(4) _cell_angle_alpha 104.191(2) _cell_angle_beta 114.809(2) _cell_angle_gamma 105.476(2) _cell_volume 1895.43(8) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 31096 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.35 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 0.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.869 _exptl_absorpt_correction_T_max 0.964 _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 17293 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.96 _diffrn_reflns_theta_max 25.27 _reflns_number_total 6729 _reflns_number_gt 5550 _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^)+(0.0854P)^2^+2.6037P] 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 6729 _refine_ls_number_parameters 509 _refine_ls_number_restraints 33 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.1901 _refine_ls_wR_factor_gt 0.1795 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.035 _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 0.05638(10) 0.84061(8) 0.37080(9) 0.0610(3) Uani 1 1 d . . . Cl21 Cl -0.13790(10) 0.61593(11) 0.33812(10) 0.0780(4) Uani 1 1 d . . . N11 N 0.1515(3) 0.8401(2) 0.1512(2) 0.0481(7) Uani 1 1 d . . . N21 N 0.2270(3) 0.9373(2) 0.1594(2) 0.0456(7) Uani 1 1 d . . . H21 H 0.2010 0.9544 0.0989 0.055 Uiso 1 1 calc R . . C31 C 0.3409(3) 1.0093(3) 0.2566(3) 0.0404(7) Uani 1 1 d . . . N31 N 0.4051(3) 1.1044(2) 0.2577(2) 0.0447(6) Uani 1 1 d . . . H31A H 0.4798 1.1530 0.3200 0.054 Uiso 1 1 calc R . . H31B H 0.3734 1.1193 0.1962 0.054 Uiso 1 1 calc R . . N41 N 0.3891(2) 0.9863(2) 0.3503(2) 0.0426(6) Uani 1 1 d . . . C51 C 0.3168(3) 0.8897(3) 0.3442(3) 0.0439(7) Uani 1 1 d . . . N51 N 0.3621(3) 0.8630(2) 0.4339(2) 0.0516(8) Uani 1 1 d . . . H51A H 0.4383 0.9084 0.4960 0.062 Uiso 1 1 calc R . . H51B H 0.3160 0.7998 0.4315 0.062 Uiso 1 1 calc R . . C61 C 0.1926(3) 0.8163(3) 0.2412(3) 0.0440(7) Uani 1 1 d . . . C611 C 0.1065(3) 0.7094(3) 0.2309(3) 0.0479(8) Uani 1 1 d . . . C621 C 0.0376(3) 0.7127(3) 0.2866(3) 0.0495(8) Uani 1 1 d . . . C631 C -0.0497(3) 0.6125(3) 0.2717(3) 0.0568(10) Uani 1 1 d . . . C641 C -0.0659(4) 0.5114(3) 0.2017(3) 0.0614(11) Uani 1 1 d . . . H641 H -0.1264 0.4435 0.1902 0.074 Uiso 1 1 calc R . . C651 C 0.0038(4) 0.5074(3) 0.1485(3) 0.0597(10) Uani 1 1 d . . . H651 H -0.0072 0.4366 0.1026 0.072 Uiso 1 1 calc R . . C661 C 0.0916(3) 0.6062(3) 0.1605(3) 0.0470(8) Uani 1 1 d . . . H661 H 0.1390 0.6033 0.1226 0.056 Uiso 1 1 calc R . . C615 C 0.320(2) 0.431(3) 0.196(2) 0.0390(8) Uani 0.0979(14) 1 d PD A 2 C625 C 0.421(3) 0.400(3) 0.236(2) 0.0415(8) Uani 0.0979(14) 1 d PD A 2 C635 C 0.482(3) 0.388(3) 0.171(2) 0.0472(11) Uani 0.0979(14) 1 d PD A 2 C645 C 0.429(6) 0.393(7) 0.065(4) 0.0534(10) Uani 0.0979(14) 1 d PD A 2 H645 H 0.4639 0.3771 0.0175 0.064 Uiso 0.0979(14) 1 calc PR A 2 C655 C 0.325(3) 0.421(3) 0.024(3) 0.0560(10) Uani 0.0979(14) 1 d PD A 2 H655 H 0.2935 0.4290 -0.0473 0.067 Uiso 0.0979(14) 1 calc PR A 2 C665 C 0.269(3) 0.438(3) 0.090(2) 0.0483(9) Uani 0.0979(14) 1 d PD A 2 H665 H 0.1948 0.4536 0.0619 0.058 Uiso 0.0979(14) 1 calc PR A 2 Cl15 Cl 0.4830(8) 0.3905(9) 0.3677(8) 0.0544(3) Uani 0.0979(14) 1 d PD A 2 Cl25 Cl 0.6090(10) 0.3508(10) 0.2181(9) 0.0654(3) Uani 0.0979(14) 1 d PD A 2 N35 N 0.075(7) 0.475(5) 0.440(6) 0.0466(12) Uani 0.0979(14) 1 d P A 2 H35A H 0.0050 0.4240 0.4276 0.056 Uiso 0.0979(14) 1 calc PR A 2 H35B H 0.1106 0.5433 0.4935 0.056 Uiso 0.0979(14) 1 calc PR A 2 N55 N 0.137(5) 0.260(4) 0.181(5) 0.0482(11) Uani 0.0979(14) 1 d P A 2 H55A H 0.0803 0.1934 0.1628 0.058 Uiso 0.0979(14) 1 calc PR A 2 H55B H 0.1880 0.2645 0.1523 0.058 Uiso 0.0979(14) 1 calc PR A 2 N15 N 0.293(3) 0.532(3) 0.344(3) 0.0418(8) Uani 0.0979(14) 1 d PD A 2 N25 N 0.229(4) 0.540(3) 0.401(3) 0.0428(9) Uani 0.0979(14) 1 d PD A 2 H25 H 0.2539 0.6050 0.4556 0.051 Uiso 0.0979(14) 1 calc PR A 2 C35 C 0.125(5) 0.450(4) 0.377(5) 0.0405(10) Uani 0.0979(14) 1 d PD A 2 N45 N 0.079(5) 0.350(3) 0.293(6) 0.0423(10) Uani 0.0979(14) 1 d PD A 2 C55 C 0.145(4) 0.338(3) 0.241(5) 0.0415(11) Uani 0.0979(14) 1 d PD A 2 C65 C 0.254(3) 0.435(3) 0.265(3) 0.0405(9) Uani 0.0979(14) 1 d PD A 2 N12 N 0.3197(3) 0.5095(3) 0.3593(3) 0.0418(8) Uani 0.9021(14) 1 d PD A 1 N22 N 0.2449(4) 0.5166(3) 0.4052(4) 0.0428(9) Uani 0.9021(14) 1 d PD A 1 H22 H 0.2687 0.5807 0.4603 0.051 Uiso 0.9021(14) 1 calc PR A 1 C32 C 0.1339(5) 0.4282(3) 0.3693(5) 0.0405(10) Uani 0.9021(14) 1 d PD A 1 N42 N 0.0912(4) 0.3292(3) 0.2852(5) 0.0423(10) Uani 0.9021(14) 1 d PD A 1 C52 C 0.1642(4) 0.3192(4) 0.2401(5) 0.0415(11) Uani 0.9021(14) 1 d PD A 1 C62 C 0.2831(3) 0.4141(3) 0.2789(3) 0.0405(9) Uani 0.9021(14) 1 d PD A 1 N32 N 0.0698(6) 0.4439(3) 0.4216(5) 0.0466(12) Uani 0.9021(14) 1 d P A 1 H32A H -0.0020 0.3888 0.4011 0.056 Uiso 0.9021(14) 1 calc PR A 1 H32B H 0.0987 0.5096 0.4771 0.056 Uiso 0.9021(14) 1 calc PR A 1 N52 N 0.1270(4) 0.2207(3) 0.1581(4) 0.0482(11) Uani 0.9021(14) 1 d P A 1 H52A H 0.0553 0.1637 0.1348 0.058 Uiso 0.9021(14) 1 calc PR A 1 H52B H 0.1741 0.2125 0.1272 0.058 Uiso 0.9021(14) 1 calc PR A 1 C612 C 0.3676(3) 0.4059(3) 0.2310(3) 0.0390(8) Uani 0.9021(14) 1 d PD A 1 C622 C 0.3300(3) 0.3955(3) 0.1186(3) 0.0415(8) Uani 0.9021(14) 1 d PD A 1 C632 C 0.4107(5) 0.3867(6) 0.0753(5) 0.0472(11) Uani 0.9021(14) 1 d PD A 1 C642 C 0.5297(4) 0.3906(3) 0.1456(4) 0.0534(10) Uani 0.9021(14) 1 d PD A 1 H642 H 0.5857 0.3867 0.1172 0.064 Uiso 0.9021(14) 1 calc PR A 1 C652 C 0.5673(4) 0.4002(4) 0.2571(4) 0.0560(10) Uani 0.9021(14) 1 d PD A 1 H652 H 0.6487 0.4017 0.3047 0.067 Uiso 0.9021(14) 1 calc PR A 1 C662 C 0.4872(4) 0.4075(3) 0.2997(4) 0.0483(9) Uani 0.9021(14) 1 d PD A 1 H662 H 0.5138 0.4137 0.3765 0.058 Uiso 0.9021(14) 1 calc PR A 1 Cl12 Cl 0.18267(9) 0.39342(9) 0.03148(9) 0.0544(3) Uani 0.9021(14) 1 d PD A 1 Cl22 Cl 0.36208(11) 0.37083(10) -0.06546(9) 0.0654(3) Uani 0.9021(14) 1 d PD A 1 O13 O 0.1666(2) 0.6584(2) 0.5878(2) 0.0613(7) Uani 1 1 d . . . O23 O 0.3215(2) 0.73053(19) 0.5549(2) 0.0476(6) Uani 1 1 d . . . O43 O 0.1209(2) 0.95885(19) 0.96741(19) 0.0514(6) Uani 1 1 d . . . O33 O 0.2618(2) 1.1371(2) 1.0600(2) 0.0566(7) Uani 1 1 d . . . C13 C 0.2532(3) 0.7399(3) 0.5999(3) 0.0470(8) Uani 1 1 d . . . C23 C 0.2824(4) 0.8549(3) 0.6747(4) 0.0660(11) Uani 1 1 d . . . H23A H 0.3127 0.9087 0.6449 0.079 Uiso 1 1 calc R . . H23B H 0.3532 0.8765 0.7543 0.079 Uiso 1 1 calc R . . C33 C 0.1660(5) 0.8634(4) 0.6793(4) 0.0720(12) Uani 1 1 d . . . H33A H 0.0982 0.8478 0.6005 0.086 Uiso 1 1 calc R . . H33B H 0.1310 0.8045 0.7019 0.086 Uiso 1 1 calc R . . C43 C 0.1930(5) 0.9722(4) 0.7595(5) 0.0732(12) Uani 1 1 d . . . H43A H 0.2320 1.0322 0.7401 0.088 Uiso 1 1 calc R . . H43B H 0.2561 0.9862 0.8395 0.088 Uiso 1 1 calc R . . C53 C 0.0697(4) 0.9766(3) 0.7540(3) 0.0573(9) Uani 1 1 d . . . H53A H 0.0187 0.9874 0.6839 0.069 Uiso 1 1 calc R . . H53B H 0.0163 0.9048 0.7489 0.069 Uiso 1 1 calc R . . C63 C 0.1043(4) 1.0709(3) 0.8595(3) 0.0562(9) Uani 1 1 d . . . H63A H 0.0249 1.0790 0.8495 0.067 Uiso 1 1 calc R . . H63B H 0.1627 1.1413 0.8665 0.067 Uiso 1 1 calc R . . C73 C 0.1689(3) 1.0559(3) 0.9706(3) 0.0443(7) Uani 1 1 d . . . O14 O 0.2971(6) 0.6979(5) 0.0312(7) 0.196(3) Uani 1 1 d . . . O24 O 0.4829(6) 0.8186(4) 0.1721(5) 0.1275(17) Uani 1 1 d . . . C14 C 0.3957(8) 0.8604(7) 0.0158(7) 0.130(3) Uani 1 1 d . . . H14A H 0.4781 0.9266 0.0687 0.195 Uiso 1 1 calc R . . H14B H 0.3247 0.8836 -0.0019 0.195 Uiso 1 1 calc R . . H14C H 0.3923 0.8236 -0.0560 0.195 Uiso 1 1 calc R . . C24 C 0.3837(6) 0.7833(6) 0.0699(7) 0.113(2) Uani 1 1 d . . . C34 C 0.4836(8) 0.7466(7) 0.2296(8) 0.135(3) Uani 1 1 d . . . H34A H 0.4769 0.6745 0.1832 0.162 Uiso 1 1 calc R . . H34B H 0.4098 0.7312 0.2417 0.162 Uiso 1 1 calc R . . C44 C 0.6062(11) 0.8038(8) 0.3420(9) 0.154(3) Uani 1 1 d . . . H44A H 0.6786 0.8168 0.3279 0.185 Uiso 1 1 calc R . . H44B H 0.6137 0.8779 0.3846 0.185 Uiso 1 1 calc R . . C54 C 0.6177(13) 0.7409(10) 0.4134(14) 0.214(6) Uani 1 1 d . . . H54A H 0.5440 0.7290 0.4255 0.257 Uiso 1 1 calc R . . H54B H 0.6052 0.6660 0.3669 0.257 Uiso 1 1 calc R . . C64 C 0.7192(14) 0.7774(13) 0.5128(13) 0.268(9) Uani 1 1 d . . . H64A H 0.7088 0.7240 0.5481 0.402 Uiso 1 1 calc R . . H64B H 0.7327 0.8503 0.5626 0.402 Uiso 1 1 calc R . . H64C H 0.7939 0.7860 0.5037 0.402 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 0.0633(6) 0.0650(6) 0.0625(6) 0.0325(5) 0.0366(5) 0.0253(5) Cl21 0.0534(6) 0.1025(9) 0.0755(7) 0.0525(7) 0.0343(5) 0.0134(6) N11 0.0377(14) 0.0462(15) 0.0426(15) 0.0224(13) 0.0123(12) 0.0038(12) N21 0.0380(14) 0.0450(15) 0.0384(14) 0.0235(12) 0.0121(12) 0.0037(12) C31 0.0341(16) 0.0426(17) 0.0388(16) 0.0185(14) 0.0167(13) 0.0104(13) N31 0.0363(14) 0.0436(15) 0.0408(14) 0.0220(12) 0.0138(12) 0.0045(12) N41 0.0323(13) 0.0458(15) 0.0392(14) 0.0225(12) 0.0130(11) 0.0065(11) C51 0.0353(16) 0.0469(18) 0.0423(17) 0.0231(15) 0.0165(14) 0.0092(14) N51 0.0368(14) 0.0520(17) 0.0431(15) 0.0275(13) 0.0086(12) 0.0002(12) C61 0.0362(16) 0.0448(18) 0.0406(17) 0.0215(14) 0.0149(14) 0.0077(14) C611 0.0338(16) 0.054(2) 0.0420(18) 0.0275(16) 0.0099(14) 0.0079(14) C621 0.0383(17) 0.054(2) 0.0449(18) 0.0282(16) 0.0121(15) 0.0136(15) C631 0.0385(18) 0.069(2) 0.053(2) 0.041(2) 0.0141(16) 0.0106(17) C641 0.043(2) 0.060(2) 0.058(2) 0.035(2) 0.0100(18) 0.0053(17) C651 0.051(2) 0.050(2) 0.053(2) 0.0239(17) 0.0109(18) 0.0105(17) C661 0.0343(16) 0.0383(17) 0.0432(18) 0.0157(14) 0.0056(14) 0.0061(13) C615 0.0336(19) 0.0354(18) 0.0392(19) 0.0172(14) 0.0146(16) 0.0079(16) C625 0.0327(17) 0.0387(18) 0.046(2) 0.0212(15) 0.0160(15) 0.0097(14) C635 0.047(3) 0.042(2) 0.052(2) 0.0207(17) 0.0287(18) 0.011(2) C645 0.046(2) 0.052(2) 0.067(3) 0.026(2) 0.034(2) 0.0174(18) C655 0.041(2) 0.058(2) 0.067(3) 0.033(2) 0.025(2) 0.0182(18) C665 0.0345(19) 0.047(2) 0.051(2) 0.0210(18) 0.0160(17) 0.0091(16) Cl15 0.0431(5) 0.0738(7) 0.0472(5) 0.0336(5) 0.0190(4) 0.0252(5) Cl25 0.0634(7) 0.0760(7) 0.0544(6) 0.0283(5) 0.0363(5) 0.0151(5) N35 0.0415(16) 0.041(3) 0.048(3) 0.016(2) 0.0247(19) 0.004(2) N55 0.0449(18) 0.033(2) 0.042(2) 0.0074(19) 0.0193(18) -0.004(2) N15 0.0337(17) 0.0454(19) 0.0420(17) 0.0197(14) 0.0189(14) 0.0103(12) N25 0.0368(18) 0.040(2) 0.0399(15) 0.0125(14) 0.0190(14) 0.0056(13) C35 0.0332(17) 0.043(3) 0.039(2) 0.022(2) 0.0156(14) 0.0087(18) N45 0.0357(17) 0.043(2) 0.0400(17) 0.0195(17) 0.0176(14) 0.0065(14) C55 0.038(2) 0.039(2) 0.0354(18) 0.016(2) 0.0140(17) 0.0080(16) C65 0.031(2) 0.043(2) 0.0380(19) 0.0182(15) 0.0129(16) 0.0087(14) N12 0.0337(17) 0.0454(19) 0.0420(17) 0.0197(14) 0.0189(14) 0.0103(12) N22 0.0368(18) 0.040(2) 0.0399(15) 0.0125(14) 0.0190(14) 0.0056(13) C32 0.0332(17) 0.043(3) 0.039(2) 0.022(2) 0.0156(14) 0.0087(18) N42 0.0357(17) 0.043(2) 0.0400(17) 0.0195(17) 0.0176(14) 0.0065(14) C52 0.038(2) 0.039(2) 0.0354(18) 0.016(2) 0.0140(17) 0.0080(16) C62 0.031(2) 0.043(2) 0.0380(19) 0.0182(15) 0.0129(16) 0.0087(14) N32 0.0415(16) 0.041(3) 0.048(3) 0.016(2) 0.0247(19) 0.004(2) N52 0.0449(18) 0.033(2) 0.042(2) 0.0074(19) 0.0193(18) -0.004(2) C612 0.0336(19) 0.0354(18) 0.0392(19) 0.0172(14) 0.0146(16) 0.0079(16) C622 0.0327(17) 0.0387(18) 0.046(2) 0.0212(15) 0.0160(15) 0.0097(14) C632 0.047(3) 0.042(2) 0.052(2) 0.0207(17) 0.0287(18) 0.011(2) C642 0.046(2) 0.052(2) 0.067(3) 0.026(2) 0.034(2) 0.0174(18) C652 0.041(2) 0.058(2) 0.067(3) 0.033(2) 0.025(2) 0.0182(18) C662 0.0345(19) 0.047(2) 0.051(2) 0.0210(18) 0.0160(17) 0.0091(16) Cl12 0.0431(5) 0.0738(7) 0.0472(5) 0.0336(5) 0.0190(4) 0.0252(5) Cl22 0.0634(7) 0.0760(7) 0.0544(6) 0.0283(5) 0.0363(5) 0.0151(5) O13 0.0484(14) 0.0541(15) 0.0750(18) 0.0245(13) 0.0372(14) 0.0056(12) O23 0.0423(12) 0.0470(13) 0.0495(13) 0.0224(11) 0.0251(11) 0.0089(10) O43 0.0486(13) 0.0439(13) 0.0386(12) 0.0209(10) 0.0116(10) 0.0029(10) O33 0.0501(14) 0.0442(13) 0.0498(14) 0.0221(11) 0.0121(12) 0.0054(11) C13 0.0373(17) 0.0497(19) 0.0500(19) 0.0268(16) 0.0192(15) 0.0127(15) C23 0.065(2) 0.052(2) 0.100(3) 0.033(2) 0.060(3) 0.0201(19) C33 0.074(3) 0.068(3) 0.083(3) 0.031(2) 0.051(3) 0.026(2) C43 0.089(3) 0.067(3) 0.090(3) 0.042(2) 0.063(3) 0.032(2) C53 0.076(3) 0.066(2) 0.057(2) 0.0402(19) 0.042(2) 0.042(2) C63 0.062(2) 0.057(2) 0.052(2) 0.0331(18) 0.0254(18) 0.0261(18) C73 0.0419(18) 0.0475(19) 0.0468(19) 0.0255(16) 0.0228(16) 0.0177(15) O14 0.114(4) 0.100(4) 0.249(8) 0.033(4) 0.043(5) -0.005(3) O24 0.147(4) 0.093(3) 0.120(4) 0.033(3) 0.082(4) 0.010(3) C14 0.132(6) 0.112(5) 0.128(6) 0.028(5) 0.076(5) 0.031(5) C24 0.078(4) 0.077(4) 0.119(5) -0.018(4) 0.044(4) 0.010(3) C34 0.124(6) 0.108(5) 0.151(7) 0.029(5) 0.087(6) 0.014(5) C44 0.205(10) 0.129(6) 0.166(8) 0.096(7) 0.117(8) 0.052(7) C54 0.187(12) 0.180(10) 0.309(18) 0.164(12) 0.118(13) 0.080(9) C64 0.206(13) 0.303(18) 0.262(15) 0.212(15) 0.031(11) 0.126(13) _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 1.728(4) . ? Cl21 C631 1.721(4) . ? N11 C61 1.299(4) . ? N11 N21 1.348(4) . ? N21 C31 1.347(4) . ? N21 H21 0.8800 . ? C31 N31 1.317(4) . ? C31 N41 1.344(4) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N41 C51 1.339(4) . ? C51 N51 1.323(4) . ? C51 C61 1.443(5) . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C61 C611 1.489(4) . ? C611 C621 1.387(5) . ? C611 C661 1.409(5) . ? C621 C631 1.401(5) . ? C631 C641 1.376(6) . ? C641 C651 1.369(6) . ? C641 H641 0.9500 . ? C651 C661 1.409(5) . ? C651 H651 0.9500 . ? C661 H661 0.9500 . ? C615 C625 1.379(18) . ? C615 C665 1.388(18) . ? C615 C65 1.51(4) . ? C625 C635 1.414(18) . ? C625 Cl15 1.718(17) . ? C635 C645 1.378(18) . ? C635 Cl25 1.720(17) . ? C645 C655 1.379(19) . ? C645 H645 0.9500 . ? C655 C665 1.389(19) . ? C655 H655 0.9500 . ? C665 H665 0.9500 . ? N35 C35 1.31(8) . ? N35 H35A 0.8800 . ? N35 H35B 0.8800 . ? N55 C55 1.13(6) . ? N55 H55A 0.8800 . ? N55 H55B 0.8800 . ? N15 C65 1.297(18) . ? N15 N25 1.355(18) . ? N25 C35 1.370(18) . ? N25 H25 0.8800 . ? C35 N45 1.329(19) . ? N45 C55 1.329(19) . ? C55 C65 1.464(18) . ? N12 C62 1.294(5) . ? N12 N22 1.352(4) . ? N22 C32 1.365(4) . ? N22 H22 0.8800 . ? C32 N32 1.318(7) . ? C32 N42 1.332(5) . ? N42 C52 1.329(5) . ? C52 N52 1.332(6) . ? C52 C62 1.461(5) . ? C62 C612 1.487(5) . ? N32 H32A 0.8800 . ? N32 H32B 0.8800 . ? N52 H52A 0.8800 . ? N52 H52B 0.8800 . ? C612 C622 1.389(5) . ? C612 C662 1.395(5) . ? C622 C632 1.397(6) . ? C622 Cl12 1.726(4) . ? C632 C642 1.380(6) . ? C632 Cl22 1.726(5) . ? C642 C652 1.379(6) . ? C642 H642 0.9500 . ? C652 C662 1.380(6) . ? C652 H652 0.9500 . ? C662 H662 0.9500 . ? O13 C13 1.245(4) . ? O23 C13 1.273(4) . ? O43 C73 1.272(4) . ? O33 C73 1.243(4) . ? C13 C23 1.491(5) . ? C23 C33 1.527(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C33 C43 1.463(6) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C43 C53 1.539(6) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C53 C63 1.492(6) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C63 C73 1.511(5) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? O14 C24 1.160(8) . ? O24 C24 1.292(9) . ? O24 C34 1.404(10) . ? C14 C24 1.441(11) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C34 C44 1.474(12) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C44 C54 1.447(13) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C54 C64 1.279(16) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 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 117.6(3) . . ? C31 N21 N11 122.5(3) . . ? C31 N21 H21 118.7 . . ? N11 N21 H21 118.7 . . ? N31 C31 N41 120.1(3) . . ? N31 C31 N21 118.0(3) . . ? N41 C31 N21 121.8(3) . . ? C31 N31 H31A 120.0 . . ? C31 N31 H31B 120.0 . . ? H31A N31 H31B 120.0 . . ? C51 N41 C31 116.9(3) . . ? N51 C51 N41 118.7(3) . . ? N51 C51 C61 121.0(3) . . ? N41 C51 C61 120.3(3) . . ? C51 N51 H51A 120.0 . . ? C51 N51 H51B 120.0 . . ? H51A N51 H51B 120.0 . . ? N11 C61 C51 120.7(3) . . ? N11 C61 C611 116.6(3) . . ? C51 C61 C611 122.6(3) . . ? C621 C611 C661 120.8(3) . . ? C621 C611 C61 119.6(3) . . ? C661 C611 C61 119.6(3) . . ? C611 C621 C631 120.0(4) . . ? C611 C621 Cl11 119.7(3) . . ? C631 C621 Cl11 120.3(3) . . ? C641 C631 C621 119.5(4) . . ? C641 C631 Cl21 120.2(3) . . ? C621 C631 Cl21 120.3(3) . . ? C651 C641 C631 120.9(4) . . ? C651 C641 H641 119.6 . . ? C631 C641 H641 119.6 . . ? C641 C651 C661 121.4(4) . . ? C641 C651 H651 119.3 . . ? C661 C651 H651 119.3 . . ? C611 C661 C651 117.4(4) . . ? C611 C661 H661 121.3 . . ? C651 C661 H661 121.3 . . ? C625 C615 C665 122(2) . . ? C625 C615 C65 115(2) . . ? C665 C615 C65 122(2) . . ? C615 C625 C635 117.7(16) . . ? C615 C625 Cl15 121.4(16) . . ? C635 C625 Cl15 120.5(16) . . ? C645 C635 C625 119.3(18) . . ? C645 C635 Cl25 120.9(17) . . ? C625 C635 Cl25 119.3(16) . . ? C635 C645 C655 122(2) . . ? C635 C645 H645 119.1 . . ? C655 C645 H645 119.1 . . ? C645 C655 C665 119(2) . . ? C645 C655 H655 120.5 . . ? C665 C655 H655 120.5 . . ? C615 C665 C655 119(2) . . ? C615 C665 H665 120.3 . . ? C655 C665 H665 120.3 . . ? C35 N35 H35A 120.0 . . ? C35 N35 H35B 120.0 . . ? H35A N35 H35B 120.0 . . ? C55 N55 H55A 120.0 . . ? C55 N55 H55B 120.0 . . ? H55A N55 H55B 120.0 . . ? C65 N15 N25 117(2) . . ? N15 N25 C35 122(2) . . ? N15 N25 H25 118.8 . . ? C35 N25 H25 118.8 . . ? N35 C35 N45 125(4) . . ? N35 C35 N25 113(4) . . ? N45 C35 N25 122(2) . . ? C35 N45 C55 117(2) . . ? N55 C55 N45 130(4) . . ? N55 C55 C65 109(4) . . ? N45 C55 C65 121(2) . . ? N15 C65 C55 120(2) . . ? N15 C65 C615 116(3) . . ? C55 C65 C615 123(3) . . ? C62 N12 N22 117.5(3) . . ? N12 N22 C32 122.5(3) . . ? N12 N22 H22 118.7 . . ? C32 N22 H22 118.7 . . ? N32 C32 N42 120.6(4) . . ? N32 C32 N22 117.4(4) . . ? N42 C32 N22 122.0(3) . . ? C52 N42 C32 116.8(3) . . ? N52 C52 N42 118.7(4) . . ? N52 C52 C62 120.2(4) . . ? N42 C52 C62 121.1(4) . . ? N12 C62 C52 120.1(4) . . ? N12 C62 C612 117.3(3) . . ? C52 C62 C612 122.6(4) . . ? C32 N32 H32A 120.0 . . ? C32 N32 H32B 120.0 . . ? H32A N32 H32B 120.0 . . ? C52 N52 H52A 120.0 . . ? C52 N52 H52B 120.0 . . ? H52A N52 H52B 120.0 . . ? C622 C612 C662 118.8(4) . . ? C622 C612 C62 121.6(3) . . ? C662 C612 C62 119.6(3) . . ? C612 C622 C632 120.5(4) . . ? C612 C622 Cl12 119.9(3) . . ? C632 C622 Cl12 119.6(3) . . ? C642 C632 C622 119.7(4) . . ? C642 C632 Cl22 120.1(3) . . ? C622 C632 Cl22 120.3(3) . . ? C652 C642 C632 120.2(4) . . ? C652 C642 H642 119.9 . . ? C632 C642 H642 119.9 . . ? C642 C652 C662 120.3(4) . . ? C642 C652 H652 119.8 . . ? C662 C652 H652 119.8 . . ? C652 C662 C612 120.5(4) . . ? C652 C662 H662 119.7 . . ? C612 C662 H662 119.7 . . ? O13 C13 O23 123.6(3) . . ? O13 C13 C23 118.4(3) . . ? O23 C13 C23 117.9(3) . . ? C13 C23 C33 112.8(3) . . ? C13 C23 H23A 109.0 . . ? C33 C23 H23A 109.0 . . ? C13 C23 H23B 109.0 . . ? C33 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C43 C33 C23 114.6(4) . . ? C43 C33 H33A 108.6 . . ? C23 C33 H33A 108.6 . . ? C43 C33 H33B 108.6 . . ? C23 C33 H33B 108.6 . . ? H33A C33 H33B 107.6 . . ? C33 C43 C53 111.6(4) . . ? C33 C43 H43A 109.3 . . ? C53 C43 H43A 109.3 . . ? C33 C43 H43B 109.3 . . ? C53 C43 H43B 109.3 . . ? H43A C43 H43B 108.0 . . ? C63 C53 C43 110.0(4) . . ? C63 C53 H53A 109.7 . . ? C43 C53 H53A 109.7 . . ? C63 C53 H53B 109.7 . . ? C43 C53 H53B 109.7 . . ? H53A C53 H53B 108.2 . . ? C53 C63 C73 114.1(3) . . ? C53 C63 H63A 108.7 . . ? C73 C63 H63A 108.7 . . ? C53 C63 H63B 108.7 . . ? C73 C63 H63B 108.7 . . ? H63A C63 H63B 107.6 . . ? O33 C73 O43 123.3(3) . . ? O33 C73 C63 120.0(3) . . ? O43 C73 C63 116.7(3) . . ? C24 O24 C34 117.2(7) . . ? C24 C14 H14A 109.5 . . ? C24 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C24 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O14 C24 O24 120.3(10) . . ? O14 C24 C14 126.8(9) . . ? O24 C24 C14 112.9(6) . . ? O24 C34 C44 107.1(6) . . ? O24 C34 H34A 110.3 . . ? C44 C34 H34A 110.3 . . ? O24 C34 H34B 110.3 . . ? C44 C34 H34B 110.3 . . ? H34A C34 H34B 108.5 . . ? C54 C44 C34 113.2(9) . . ? C54 C44 H44A 108.9 . . ? C34 C44 H44A 108.9 . . ? C54 C44 H44B 108.9 . . ? C34 C44 H44B 108.9 . . ? H44A C44 H44B 107.8 . . ? C64 C54 C44 121.3(12) . . ? C64 C54 H54A 107.0 . . ? C44 C54 H54A 107.0 . . ? C64 C54 H54B 107.0 . . ? C44 C54 H54B 107.0 . . ? H54A C54 H54B 106.7 . . ? C54 C64 H64A 109.5 . . ? C54 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? C54 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 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 -0.6(5) . . . . ? N11 N21 C31 N31 -177.2(3) . . . . ? N11 N21 C31 N41 3.0(5) . . . . ? N31 C31 N41 C51 178.1(3) . . . . ? N21 C31 N41 C51 -2.1(5) . . . . ? C31 N41 C51 N51 178.7(3) . . . . ? C31 N41 C51 C61 -0.9(5) . . . . ? N21 N11 C61 C51 -2.3(5) . . . . ? N21 N11 C61 C611 179.0(3) . . . . ? N51 C51 C61 N11 -176.4(3) . . . . ? N41 C51 C61 N11 3.1(5) . . . . ? N51 C51 C61 C611 2.2(6) . . . . ? N41 C51 C61 C611 -178.2(3) . . . . ? N11 C61 C611 C621 -105.2(4) . . . . ? C51 C61 C611 C621 76.1(4) . . . . ? N11 C61 C611 C661 72.0(4) . . . . ? C51 C61 C611 C661 -106.7(4) . . . . ? C661 C611 C621 C631 -1.2(5) . . . . ? C61 C611 C621 C631 176.0(3) . . . . ? C661 C611 C621 Cl11 -179.2(2) . . . . ? C61 C611 C621 Cl11 -1.9(4) . . . . ? C611 C621 C631 C641 0.2(5) . . . . ? Cl11 C621 C631 C641 178.2(3) . . . . ? C611 C621 C631 Cl21 -178.6(3) . . . . ? Cl11 C621 C631 Cl21 -0.7(4) . . . . ? C621 C631 C641 C651 1.3(5) . . . . ? Cl21 C631 C641 C651 -179.8(3) . . . . ? C631 C641 C651 C661 -1.9(6) . . . . ? C621 C611 C661 C651 0.6(5) . . . . ? C61 C611 C661 C651 -176.6(3) . . . . ? C641 C651 C661 C611 1.0(5) . . . . ? C665 C615 C625 C635 8(5) . . . . ? C65 C615 C625 C635 176(3) . . . . ? C665 C615 C625 Cl15 -179(3) . . . . ? C65 C615 C625 Cl15 -11(5) . . . . ? C615 C625 C635 C645 -8(7) . . . . ? Cl15 C625 C635 C645 178(5) . . . . ? C615 C625 C635 Cl25 180(3) . . . . ? Cl15 C625 C635 Cl25 6(4) . . . . ? C625 C635 C645 C655 7(10) . . . . ? Cl25 C635 C645 C655 179(5) . . . . ? C635 C645 C655 C665 -4(10) . . . . ? C625 C615 C665 C655 -5(5) . . . . ? C65 C615 C665 C655 -173(3) . . . . ? C645 C655 C665 C615 3(7) . . . . ? C65 N15 N25 C35 -1(3) . . . . ? N15 N25 C35 N35 -179(6) . . . . ? N15 N25 C35 N45 -2(3) . . . . ? N35 C35 N45 C55 -178(7) . . . . ? N25 C35 N45 C55 6(6) . . . . ? C35 N45 C55 N55 167(7) . . . . ? C35 N45 C55 C65 -7(7) . . . . ? N25 N15 C65 C55 -1(5) . . . . ? N25 N15 C65 C615 175(3) . . . . ? N55 C55 C65 N15 -171(5) . . . . ? N45 C55 C65 N15 5(7) . . . . ? N55 C55 C65 C615 14(7) . . . . ? N45 C55 C65 C615 -171(4) . . . . ? C625 C615 C65 N15 95(4) . . . . ? C665 C615 C65 N15 -96(4) . . . . ? C625 C615 C65 C55 -89(5) . . . . ? C665 C615 C65 C55 80(5) . . . . ? C62 N12 N22 C32 -0.4(5) . . . . ? N12 N22 C32 N32 178.7(5) . . . . ? N12 N22 C32 N42 -1.0(6) . . . . ? N32 C32 N42 C52 -177.6(6) . . . . ? N22 C32 N42 C52 2.1(6) . . . . ? C32 N42 C52 N52 178.0(5) . . . . ? C32 N42 C52 C62 -2.0(7) . . . . ? N22 N12 C62 C52 0.5(5) . . . . ? N22 N12 C62 C612 -178.4(3) . . . . ? N52 C52 C62 N12 -179.3(4) . . . . ? N42 C52 C62 N12 0.7(6) . . . . ? N52 C52 C62 C612 -0.5(6) . . . . ? N42 C52 C62 C612 179.6(4) . . . . ? N12 C62 C612 C622 -110.8(4) . . . . ? C52 C62 C612 C622 70.4(5) . . . . ? N12 C62 C612 C662 69.9(5) . . . . ? C52 C62 C612 C662 -108.9(4) . . . . ? C662 C612 C622 C632 0.0(6) . . . . ? C62 C612 C622 C632 -179.3(4) . . . . ? C662 C612 C622 Cl12 -179.9(3) . . . . ? C62 C612 C622 Cl12 0.8(5) . . . . ? C612 C622 C632 C642 -1.2(8) . . . . ? Cl12 C622 C632 C642 178.7(4) . . . . ? C612 C622 C632 Cl22 178.6(3) . . . . ? Cl12 C622 C632 Cl22 -1.5(6) . . . . ? C622 C632 C642 C652 1.6(8) . . . . ? Cl22 C632 C642 C652 -178.2(4) . . . . ? C632 C642 C652 C662 -0.9(7) . . . . ? C642 C652 C662 C612 -0.3(6) . . . . ? C622 C612 C662 C652 0.8(5) . . . . ? C62 C612 C662 C652 -179.9(4) . . . . ? O13 C13 C23 C33 -27.9(5) . . . . ? O23 C13 C23 C33 154.4(4) . . . . ? C13 C23 C33 C43 175.0(4) . . . . ? C23 C33 C43 C53 176.6(4) . . . . ? C33 C43 C53 C63 162.1(4) . . . . ? C43 C53 C63 C73 -66.2(4) . . . . ? C53 C63 C73 O33 138.7(4) . . . . ? C53 C63 C73 O43 -43.2(5) . . . . ? C34 O24 C24 O14 3.7(11) . . . . ? C34 O24 C24 C14 -176.7(6) . . . . ? C24 O24 C34 C44 178.8(7) . . . . ? O24 C34 C44 C54 177.4(9) . . . . ? C34 C44 C54 C64 178.7(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 N21 H21 O43 0.88 1.71 2.571(3) 166.9 1_554 N21 H21 O33 0.88 2.65 3.337(3) 136.3 1_554 N31 H31A O23 0.88 2.16 3.024(3) 166.8 2_676 N31 H31B O33 0.88 1.95 2.808(4) 165.1 1_554 N51 H51A N41 0.88 2.07 2.947(4) 175.5 2_676 N51 H51B O23 0.88 2.14 2.834(3) 135.8 . N22 H22 O23 0.88 1.88 2.744(4) 167.5 . N32 H32A O13 0.88 2.08 2.858(6) 146.7 2_566 N32 H32B O13 0.88 1.90 2.780(4) 174.1 . N52 H52A O43 0.88 1.98 2.827(4) 160.6 2_566 N52 H52B O33 0.88 2.03 2.871(5) 158.3 1_544 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.27 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.852 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.061 data_LMPI_thf _database_code_depnum_ccdc_archive 'CCDC 908276' #TrackingRef '15041_web_deposit_cif_file_3_JuditGalcera_1351546362.LMPI_thf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium - pimelate - tetrahydrofuran solvate (2:1:2) ; _chemical_name_common 'Lamotrigine hemipimelate tetrahydrofuran solvate' _chemical_melting_point ? _chemical_formula_moiety '2(C9 H8 Cl2 N5), C7 H10 O4, 2(C4 H8 O)' _chemical_formula_sum 'C33 H42 Cl4 N10 O6' _chemical_formula_weight 816.57 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.9830(3) _cell_length_b 13.6706(3) _cell_length_c 13.8425(4) _cell_angle_alpha 102.6810(10) _cell_angle_beta 115.7560(10) _cell_angle_gamma 106.841(2) _cell_volume 1940.40(8) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 38842 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 0.362 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.869 _exptl_absorpt_correction_T_max 0.964 _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 25210 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 25.05 _reflns_number_total 6808 _reflns_number_gt 5450 _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 & Chapuis, 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^)+(0.0924P)^2^+4.8959P] 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 6808 _refine_ls_number_parameters 522 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0778 _refine_ls_wR_factor_ref 0.2172 _refine_ls_wR_factor_gt 0.2039 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.054 _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 C616 C 0.184(4) 0.575(5) 0.303(3) 0.0321(9) Uani 0.0672(18) 1 d PD A 2 C626 C 0.083(4) 0.602(5) 0.263(3) 0.0363(10) Uani 0.0672(18) 1 d PD A 2 C636 C 0.029(4) 0.615(6) 0.331(3) 0.0405(11) Uani 0.0672(18) 1 d PD A 2 C646 C 0.077(7) 0.602(10) 0.435(5) 0.0453(11) Uani 0.0672(18) 1 d PD A 2 H646 H 0.0337 0.6026 0.4750 0.054 Uiso 0.0672(18) 1 calc PR A 2 C656 C 0.187(4) 0.587(6) 0.482(4) 0.0468(11) Uani 0.0672(18) 1 d PD A 2 H656 H 0.2254 0.5878 0.5580 0.056 Uiso 0.0672(18) 1 calc PR A 2 C666 C 0.238(5) 0.571(6) 0.413(4) 0.0403(10) Uani 0.0672(18) 1 d PD A 2 H666 H 0.3111 0.5565 0.4420 0.048 Uiso 0.0672(18) 1 calc PR A 2 Cl16 Cl 0.0201(16) 0.6105(17) 0.1298(15) 0.0511(4) Uani 0.0672(18) 1 d PD A 2 Cl26 Cl -0.1060(16) 0.6374(17) 0.2749(15) 0.0578(4) Uani 0.0672(18) 1 d PD A 2 N16 N 0.223(3) 0.481(3) 0.171(3) 0.0339(8) Uani 0.0672(18) 1 d PD A 2 N26 N 0.285(4) 0.478(3) 0.114(3) 0.0336(8) Uani 0.0672(18) 1 d PD A 2 H26 H 0.2657 0.4128 0.0644 0.040 Uiso 0.0672(18) 1 calc PR A 2 C36 C 0.375(4) 0.571(3) 0.129(3) 0.0328(9) Uani 0.0672(18) 1 d PD A 2 N46 N 0.413(4) 0.672(3) 0.207(3) 0.0344(7) Uani 0.0672(18) 1 d PD A 2 C56 C 0.351(3) 0.6798(19) 0.262(3) 0.0340(9) Uani 0.0672(18) 1 d PD A 2 C66 C 0.254(3) 0.578(2) 0.243(3) 0.0328(9) Uani 0.0672(18) 1 d PD A 2 N36 N 0.430(5) 0.560(4) 0.069(4) 0.0393(8) Uani 0.0672(18) 1 d PD A 2 H36A H 0.4916 0.6182 0.0809 0.047 Uiso 0.0672(18) 1 calc PR A 2 H36B H 0.4043 0.4934 0.0182 0.047 Uiso 0.0672(18) 1 calc PR A 2 N56 N 0.37509(19) 0.77610(16) 0.33281(16) 0.0404(8) Uani 0.0672(18) 1 d PD A 2 H56A H 0.4334 0.8382 0.3453 0.048 Uiso 0.0672(18) 1 calc PR A 2 H56B H 0.3326 0.7785 0.3677 0.048 Uiso 0.0672(18) 1 calc PR A 2 N11 N 0.18417(19) 0.48877(16) 0.13396(16) 0.0339(8) Uani 0.9328(18) 1 d PRD A 1 N21 N 0.25799(19) 0.48248(16) 0.08947(16) 0.0336(8) Uani 0.9328(18) 1 d PRD A 1 H21 H 0.2341 0.4190 0.0347 0.040 Uiso 0.9328(18) 1 calc PR A 1 C31 C 0.36764(19) 0.57110(16) 0.12691(16) 0.0328(9) Uani 0.9328(18) 1 d PRD A 1 N41 N 0.40976(19) 0.67023(16) 0.20936(16) 0.0344(7) Uani 0.9328(18) 1 d PRD A 1 C51 C 0.33881(19) 0.67994(16) 0.25421(16) 0.0340(9) Uani 0.9328(18) 1 d PRD A 1 C61 C 0.22119(19) 0.58358(16) 0.21324(16) 0.0328(9) Uani 0.9328(18) 1 d PRD A 1 N31 N 0.43095(19) 0.55554(16) 0.07567(16) 0.0393(8) Uani 0.9328(18) 1 d PRD A 1 H31A H 0.5016 0.6109 0.0959 0.047 Uiso 0.9328(18) 1 d PR A 1 H31B H 0.4022 0.4899 0.0215 0.047 Uiso 0.9328(18) 1 d PR A 1 N51 N 0.3748(4) 0.7763(3) 0.3327(3) 0.0404(8) Uani 0.9328(18) 1 d PD A 1 H51A H 0.4450 0.8338 0.3553 0.048 Uiso 0.9328(18) 1 calc PR A 1 H51B H 0.3288 0.7837 0.3629 0.048 Uiso 0.9328(18) 1 calc PR A 1 C611 C 0.1382(4) 0.5904(3) 0.2605(4) 0.0321(9) Uani 0.9328(18) 1 d PD A 1 C621 C 0.1757(4) 0.5978(4) 0.3732(4) 0.0363(10) Uani 0.9328(18) 1 d PD A 1 C631 C 0.0968(5) 0.6036(5) 0.4153(4) 0.0405(11) Uani 0.9328(18) 1 d PD A 1 C641 C -0.0196(5) 0.6004(4) 0.3447(4) 0.0453(11) Uani 0.9328(18) 1 d PD A 1 H641 H -0.0742 0.6023 0.3729 0.054 Uiso 0.9328(18) 1 calc PR A 1 C651 C -0.0567(5) 0.5946(4) 0.2328(4) 0.0468(11) Uani 0.9328(18) 1 d PD A 1 H651 H -0.1362 0.5939 0.1848 0.056 Uiso 0.9328(18) 1 calc PR A 1 C661 C 0.0215(4) 0.5898(4) 0.1905(4) 0.0403(10) Uani 0.9328(18) 1 d PD A 1 H661 H -0.0043 0.5860 0.1136 0.048 Uiso 0.9328(18) 1 calc PR A 1 Cl11 Cl 0.31996(12) 0.59973(12) 0.46155(11) 0.0511(4) Uani 0.9328(18) 1 d PD A 1 Cl21 Cl 0.14526(13) 0.61525(12) 0.55717(11) 0.0578(4) Uani 0.9328(18) 1 d PD A 1 Cl12 Cl 0.44493(13) 0.16438(12) 0.13304(11) 0.0608(4) Uani 1 1 d . . . Cl22 Cl 0.63417(14) 0.39424(15) 0.16883(14) 0.0791(5) Uani 1 1 d . . . N12 N 0.3537(3) 0.1500(3) 0.3456(3) 0.0455(9) Uani 1 1 d . . . N22 N 0.2791(3) 0.0528(3) 0.3375(3) 0.0423(9) Uani 1 1 d . . . H22 H 0.3087 0.0317 0.3955 0.051 Uiso 1 1 calc R . . C32 C 0.1602(4) -0.0135(3) 0.2433(3) 0.0383(9) Uani 1 1 d . . . N32 N 0.0940(3) -0.1076(3) 0.2439(3) 0.0452(9) Uani 1 1 d . . . H32A H 0.0162 -0.1525 0.1841 0.054 Uiso 1 1 calc R . . H32B H 0.1280 -0.1250 0.3041 0.054 Uiso 1 1 calc R . . N42 N 0.1097(3) 0.0136(3) 0.1525(3) 0.0428(9) Uani 1 1 d . . . C52 C 0.1822(4) 0.1079(4) 0.1561(4) 0.0427(10) Uani 1 1 d . . . N52 N 0.1365(3) 0.1365(3) 0.0673(3) 0.0538(11) Uani 1 1 d . . . H52A H 0.0588 0.0936 0.0062 0.065 Uiso 1 1 calc R . . H52B H 0.1837 0.1986 0.0689 0.065 Uiso 1 1 calc R . . C62 C 0.3091(4) 0.1785(4) 0.2583(4) 0.0421(10) Uani 1 1 d . . . C612 C 0.3928(4) 0.2870(4) 0.2695(4) 0.0457(11) Uani 1 1 d . . . C622 C 0.4608(4) 0.2874(4) 0.2157(4) 0.0485(11) Uani 1 1 d . . . C632 C 0.5463(4) 0.3917(5) 0.2323(5) 0.0575(14) Uani 1 1 d . . . C642 C 0.5569(5) 0.4894(5) 0.2998(5) 0.0629(15) Uani 1 1 d . . . H642 H 0.6139 0.5589 0.3111 0.076 Uiso 1 1 calc R . . C652 C 0.4877(5) 0.4884(4) 0.3504(5) 0.0587(13) Uani 1 1 d . . . H652 H 0.4971 0.5574 0.3955 0.070 Uiso 1 1 calc R . . C662 C 0.4020(4) 0.3879(3) 0.3383(4) 0.0449(11) Uani 1 1 d . . . H662 H 0.3535 0.3874 0.3737 0.054 Uiso 1 1 calc R . . O13 O 0.6673(3) 0.6561(2) 0.0903(3) 0.0474(8) Uani 1 1 d . . . O23 O 0.8168(3) 0.7294(2) 0.0552(2) 0.0386(7) Uani 1 1 d . . . O33 O 0.7522(3) 1.1458(2) 0.5616(2) 0.0417(7) Uani 1 1 d . . . O43 O 0.6166(3) 0.9667(2) 0.4659(2) 0.0454(7) Uani 1 1 d . . . C13 C 0.7499(4) 0.7376(3) 0.0994(3) 0.0363(9) Uani 1 1 d . . . C23 C 0.7771(4) 0.8538(4) 0.1695(4) 0.0449(10) Uani 1 1 d . . . H23A H 0.8019 0.9045 0.1341 0.054 Uiso 1 1 calc R . . H23B H 0.8503 0.8804 0.2501 0.054 Uiso 1 1 calc R . . C33 C 0.6651(4) 0.8610(4) 0.1758(4) 0.0435(10) Uani 1 1 d . . . H33A H 0.5962 0.8449 0.0965 0.052 Uiso 1 1 calc R . . H33B H 0.6324 0.8026 0.2003 0.052 Uiso 1 1 calc R . . C43 C 0.6969(4) 0.9735(3) 0.2596(4) 0.0437(10) Uani 1 1 d . . . H43A H 0.7388 1.0333 0.2414 0.052 Uiso 1 1 calc R . . H43B H 0.7574 0.9859 0.3408 0.052 Uiso 1 1 calc R . . C53 C 0.5783(4) 0.9804(4) 0.2513(4) 0.0426(10) Uani 1 1 d . . . H53A H 0.5289 0.9885 0.1779 0.051 Uiso 1 1 calc R . . H53B H 0.5242 0.9099 0.2476 0.051 Uiso 1 1 calc R . . C63 C 0.6097(5) 1.0776(4) 0.3546(4) 0.0440(10) Uani 1 1 d . . . H63A H 0.6714 1.1469 0.3632 0.053 Uiso 1 1 calc R . . H63B H 0.5312 1.0862 0.3373 0.053 Uiso 1 1 calc R . . C73 C 0.6646(4) 1.0639(3) 0.4691(4) 0.0346(9) Uani 1 1 d . . . O14 O 0.2456(6) 0.2680(6) 0.4803(7) 0.101(2) Uani 0.740(7) 1 d PD B 1 C24 C 0.1354(9) 0.2778(12) 0.4186(11) 0.101(4) Uani 0.740(7) 1 d PD B 1 H24A H 0.1234 0.2816 0.3441 0.121 Uiso 0.740(7) 1 calc PR B 1 H24B H 0.1381 0.3459 0.4650 0.121 Uiso 0.740(7) 1 calc PR B 1 C34 C 0.037(2) 0.1824(18) 0.397(3) 0.188(7) Uani 0.740(7) 1 d PD B 1 H34A H -0.0111 0.1302 0.3140 0.226 Uiso 0.740(7) 1 calc PR B 1 H34B H -0.0224 0.2030 0.4139 0.226 Uiso 0.740(7) 1 calc PR B 1 C44 C 0.094(3) 0.1286(19) 0.474(3) 0.172(8) Uani 0.740(7) 1 d PD B 1 H44A H 0.0494 0.1099 0.5148 0.206 Uiso 0.740(7) 1 calc PR B 1 H44B H 0.0909 0.0597 0.4287 0.206 Uiso 0.740(7) 1 calc PR B 1 C54 C 0.214(3) 0.2050(19) 0.550(2) 0.180(6) Uani 0.740(7) 1 d PD B 1 H54A H 0.2712 0.1695 0.5782 0.216 Uiso 0.740(7) 1 calc PR B 1 H54B H 0.2214 0.2560 0.6188 0.216 Uiso 0.740(7) 1 calc PR B 1 O17 O 0.1699(18) 0.3116(17) 0.5501(19) 0.101(2) Uani 0.260(7) 1 d PD B 2 C27 C 0.087(3) 0.273(4) 0.429(2) 0.101(4) Uani 0.260(7) 1 d PD B 2 H27A H 0.0240 0.3040 0.4119 0.121 Uiso 0.260(7) 1 calc PR B 2 H27B H 0.1345 0.2945 0.3917 0.121 Uiso 0.260(7) 1 calc PR B 2 C37 C 0.026(8) 0.157(4) 0.389(6) 0.188(7) Uani 0.260(7) 1 d PD B 2 H37A H 0.0340 0.1208 0.3241 0.226 Uiso 0.260(7) 1 calc PR B 2 H37B H -0.0651 0.1314 0.3609 0.226 Uiso 0.260(7) 1 calc PR B 2 C47 C 0.090(10) 0.128(4) 0.489(9) 0.172(8) Uani 0.260(7) 1 d PD B 2 H47A H 0.0520 0.1308 0.5379 0.206 Uiso 0.260(7) 1 calc PR B 2 H47B H 0.0892 0.0544 0.4640 0.206 Uiso 0.260(7) 1 calc PR B 2 C57 C 0.207(8) 0.213(5) 0.544(6) 0.180(6) Uani 0.260(7) 1 d PD B 2 H57A H 0.2473 0.2076 0.4978 0.216 Uiso 0.260(7) 1 calc PR B 2 H57B H 0.2644 0.2180 0.6232 0.216 Uiso 0.260(7) 1 calc PR B 2 O15 O 0.7986(17) 0.2841(11) 0.0272(13) 0.331(10) Uani 1 1 d D . . C25 C 0.832(3) 0.2100(17) -0.0249(19) 0.281(13) Uani 1 1 d D . . H25A H 0.7732 0.1761 -0.1110 0.337 Uiso 1 1 calc R . . H25B H 0.9197 0.2490 -0.0059 0.337 Uiso 1 1 calc R . . C35 C 0.823(2) 0.1280(14) 0.021(2) 0.294(13) Uani 1 1 d D . . H35A H 0.9072 0.1310 0.0690 0.353 Uiso 1 1 calc R . . H35B H 0.7650 0.0527 -0.0428 0.353 Uiso 1 1 calc R . . C45 C 0.771(2) 0.155(2) 0.092(2) 0.302(15) Uani 1 1 d D . . H45A H 0.6815 0.1413 0.0459 0.362 Uiso 1 1 calc R . . H45B H 0.7834 0.1185 0.1482 0.362 Uiso 1 1 calc R . . C55 C 0.858(3) 0.2663(19) 0.1430(14) 0.44(3) Uani 1 1 d D . . H55A H 0.9464 0.2772 0.1735 0.528 Uiso 1 1 calc R . . H55B H 0.8517 0.3125 0.2046 0.528 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 C616 0.030(2) 0.030(2) 0.030(2) 0.0101(18) 0.0143(19) 0.0079(18) C626 0.030(2) 0.035(2) 0.036(2) 0.0164(19) 0.0140(19) 0.0100(18) C636 0.042(3) 0.041(2) 0.036(3) 0.018(2) 0.024(2) 0.009(2) C646 0.044(3) 0.050(3) 0.048(3) 0.022(2) 0.030(2) 0.018(2) C656 0.036(2) 0.054(3) 0.050(3) 0.023(2) 0.023(2) 0.017(2) C666 0.031(2) 0.045(3) 0.036(2) 0.016(2) 0.014(2) 0.012(2) Cl16 0.0414(7) 0.0740(9) 0.0401(6) 0.0314(6) 0.0179(5) 0.0278(6) Cl26 0.0544(7) 0.0737(9) 0.0389(7) 0.0266(6) 0.0274(6) 0.0131(6) N16 0.0308(19) 0.0372(19) 0.028(2) 0.0109(16) 0.0141(16) 0.0112(16) N26 0.029(2) 0.0346(18) 0.0274(19) 0.0069(15) 0.0141(16) 0.0082(15) C36 0.032(2) 0.035(2) 0.028(2) 0.0131(17) 0.0152(17) 0.0118(17) N46 0.0333(17) 0.0320(17) 0.0297(17) 0.0093(14) 0.0160(15) 0.0077(14) C56 0.033(2) 0.035(2) 0.026(2) 0.0106(17) 0.0137(17) 0.0093(17) C66 0.027(2) 0.038(2) 0.026(2) 0.0120(18) 0.0118(18) 0.0107(18) N36 0.0394(19) 0.0346(18) 0.039(2) 0.0087(15) 0.0246(17) 0.0093(15) N56 0.0410(19) 0.0355(19) 0.0366(19) 0.0066(15) 0.0241(16) 0.0072(15) N11 0.0308(19) 0.0372(19) 0.028(2) 0.0109(16) 0.0141(16) 0.0112(16) N21 0.029(2) 0.0346(18) 0.0274(19) 0.0069(15) 0.0141(16) 0.0082(15) C31 0.032(2) 0.035(2) 0.028(2) 0.0131(17) 0.0152(17) 0.0118(17) N41 0.0333(17) 0.0320(17) 0.0297(17) 0.0093(14) 0.0160(15) 0.0077(14) C51 0.033(2) 0.035(2) 0.026(2) 0.0106(17) 0.0137(17) 0.0093(17) C61 0.027(2) 0.038(2) 0.026(2) 0.0120(18) 0.0118(18) 0.0107(18) N31 0.0394(19) 0.0346(18) 0.039(2) 0.0087(15) 0.0246(17) 0.0093(15) N51 0.0410(19) 0.0355(19) 0.0366(19) 0.0066(15) 0.0241(16) 0.0072(15) C611 0.030(2) 0.030(2) 0.030(2) 0.0101(18) 0.0143(19) 0.0079(18) C621 0.030(2) 0.035(2) 0.036(2) 0.0164(19) 0.0140(19) 0.0100(18) C631 0.042(3) 0.041(2) 0.036(3) 0.018(2) 0.024(2) 0.009(2) C641 0.044(3) 0.050(3) 0.048(3) 0.022(2) 0.030(2) 0.018(2) C651 0.036(2) 0.054(3) 0.050(3) 0.023(2) 0.023(2) 0.017(2) C661 0.031(2) 0.045(3) 0.036(2) 0.016(2) 0.014(2) 0.012(2) Cl11 0.0414(7) 0.0740(9) 0.0401(6) 0.0314(6) 0.0179(5) 0.0278(6) Cl21 0.0544(7) 0.0737(9) 0.0389(7) 0.0266(6) 0.0274(6) 0.0131(6) Cl12 0.0718(8) 0.0702(8) 0.0515(7) 0.0307(6) 0.0373(7) 0.0327(7) Cl22 0.0581(8) 0.1101(12) 0.0708(9) 0.0537(9) 0.0375(7) 0.0211(8) N12 0.0347(18) 0.048(2) 0.039(2) 0.0223(17) 0.0127(16) 0.0071(16) N22 0.0354(18) 0.043(2) 0.0328(18) 0.0207(16) 0.0116(15) 0.0052(16) C32 0.035(2) 0.042(2) 0.030(2) 0.0162(18) 0.0143(18) 0.0094(18) N32 0.0372(19) 0.044(2) 0.0350(19) 0.0200(17) 0.0107(16) 0.0046(16) N42 0.0340(18) 0.045(2) 0.0326(19) 0.0196(16) 0.0104(15) 0.0057(16) C52 0.035(2) 0.045(2) 0.037(2) 0.020(2) 0.0148(19) 0.0081(19) N52 0.0359(19) 0.055(2) 0.041(2) 0.0290(19) 0.0057(17) 0.0013(17) C62 0.035(2) 0.043(2) 0.037(2) 0.0197(19) 0.0140(19) 0.0075(18) C612 0.031(2) 0.057(3) 0.034(2) 0.025(2) 0.0089(18) 0.011(2) C622 0.040(2) 0.060(3) 0.038(2) 0.028(2) 0.013(2) 0.018(2) C632 0.036(2) 0.072(4) 0.051(3) 0.042(3) 0.011(2) 0.014(2) C642 0.046(3) 0.070(4) 0.056(3) 0.041(3) 0.013(2) 0.015(3) C652 0.050(3) 0.050(3) 0.057(3) 0.025(2) 0.016(2) 0.016(2) C662 0.039(2) 0.032(2) 0.035(2) 0.0101(18) 0.0026(19) 0.0100(18) O13 0.0489(17) 0.0352(16) 0.059(2) 0.0114(14) 0.0382(16) 0.0104(14) O23 0.0411(15) 0.0363(15) 0.0397(16) 0.0134(13) 0.0260(14) 0.0128(13) O33 0.0438(16) 0.0350(15) 0.0348(16) 0.0121(13) 0.0169(14) 0.0112(13) O43 0.0465(17) 0.0385(16) 0.0304(15) 0.0150(13) 0.0125(13) 0.0050(13) C13 0.036(2) 0.035(2) 0.030(2) 0.0102(17) 0.0164(18) 0.0109(18) C23 0.048(2) 0.039(2) 0.046(3) 0.013(2) 0.030(2) 0.014(2) C33 0.050(3) 0.042(2) 0.043(2) 0.016(2) 0.030(2) 0.019(2) C43 0.058(3) 0.035(2) 0.043(2) 0.0151(19) 0.033(2) 0.017(2) C53 0.055(3) 0.047(2) 0.033(2) 0.0206(19) 0.025(2) 0.027(2) C63 0.062(3) 0.046(2) 0.038(2) 0.022(2) 0.029(2) 0.032(2) C73 0.039(2) 0.037(2) 0.034(2) 0.0151(18) 0.0225(19) 0.0183(19) O14 0.081(4) 0.096(5) 0.119(5) 0.045(4) 0.053(4) 0.029(3) C24 0.062(7) 0.125(8) 0.121(8) 0.080(7) 0.046(6) 0.027(7) C34 0.111(9) 0.159(16) 0.179(13) 0.095(12) 0.022(8) -0.016(10) C44 0.165(11) 0.112(8) 0.137(13) 0.068(8) 0.038(10) -0.012(8) C54 0.213(13) 0.096(8) 0.113(8) 0.067(7) 0.016(9) 0.017(8) O17 0.081(4) 0.096(5) 0.119(5) 0.045(4) 0.053(4) 0.029(3) C27 0.062(7) 0.125(8) 0.121(8) 0.080(7) 0.046(6) 0.027(7) C37 0.111(9) 0.159(16) 0.179(13) 0.095(12) 0.022(8) -0.016(10) C47 0.165(11) 0.112(8) 0.137(13) 0.068(8) 0.038(10) -0.012(8) C57 0.213(13) 0.096(8) 0.113(8) 0.067(7) 0.016(9) 0.017(8) O15 0.39(2) 0.195(12) 0.205(13) 0.045(10) 0.005(13) 0.154(14) C25 0.55(4) 0.25(2) 0.31(3) 0.18(2) 0.34(3) 0.28(3) C35 0.44(3) 0.177(15) 0.54(4) 0.23(2) 0.36(3) 0.24(2) C45 0.35(3) 0.32(3) 0.22(2) 0.15(2) 0.18(2) 0.05(3) C55 0.70(7) 0.25(3) 0.103(12) 0.046(15) 0.02(2) 0.21(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 C616 C626 1.375(19) . ? C616 C666 1.398(19) . ? C616 C66 1.48(5) . ? C626 C636 1.398(19) . ? C626 Cl16 1.714(18) . ? C636 C646 1.377(19) . ? C636 Cl26 1.735(18) . ? C646 C656 1.38(2) . ? C646 H646 0.9500 . ? C656 C666 1.39(2) . ? C656 H656 0.9500 . ? C666 H666 0.9500 . ? N16 C66 1.293(19) . ? N16 N26 1.354(19) . ? N26 C36 1.353(18) . ? N26 H26 0.8800 . ? C36 N36 1.321(18) . ? C36 N46 1.341(18) . ? N46 C56 1.333(18) . ? C56 N56 1.313(18) . ? C56 C66 1.465(18) . ? N36 H36A 0.8800 . ? N36 H36B 0.8800 . ? N36 H31A 0.8425 . ? N36 H31B 0.8925 . ? N56 H56A 0.8800 . ? N56 H56B 0.8800 . ? N11 C61 1.2928 . ? N11 N21 1.3574 . ? N21 C31 1.3589 . ? N21 H21 0.8800 . ? C31 N31 1.3288 . ? C31 N41 1.3368 . ? N41 C51 1.3354 . ? C51 N51 1.307(4) . ? C51 C61 1.4638 . ? C61 C611 1.497(5) . ? N31 H31A 0.8800 . ? N31 H31B 0.8800 . ? N51 H51A 0.8800 . ? N51 H51B 0.8800 . ? C611 C621 1.386(6) . ? C611 C661 1.396(6) . ? C621 C631 1.393(6) . ? C621 Cl11 1.723(4) . ? C631 C641 1.379(7) . ? C631 Cl21 1.735(5) . ? C641 C651 1.383(7) . ? C641 H641 0.9500 . ? C651 C661 1.386(7) . ? C651 H651 0.9500 . ? C661 H661 0.9500 . ? Cl12 C622 1.712(5) . ? Cl22 C632 1.713(6) . ? N12 C62 1.295(5) . ? N12 N22 1.346(5) . ? N22 C32 1.351(5) . ? N22 H22 0.8800 . ? C32 N32 1.328(5) . ? C32 N42 1.333(5) . ? N32 H32A 0.8800 . ? N32 H32B 0.8800 . ? N42 C52 1.333(5) . ? C52 N52 1.316(5) . ? C52 C62 1.449(6) . ? N52 H52A 0.8800 . ? N52 H52B 0.8800 . ? C62 C612 1.491(6) . ? C612 C622 1.380(7) . ? C612 C662 1.434(7) . ? C622 C632 1.427(7) . ? C632 C642 1.381(8) . ? C642 C652 1.358(8) . ? C642 H642 0.9500 . ? C652 C662 1.415(7) . ? C652 H652 0.9500 . ? C662 H662 0.9500 . ? O13 C13 1.239(5) . ? O23 C13 1.276(5) . ? O33 C73 1.246(5) . ? O43 C73 1.275(5) . ? C13 C23 1.514(6) . ? C23 C33 1.523(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C33 C43 1.521(6) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C43 C53 1.525(6) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C53 C63 1.524(6) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C63 C73 1.511(6) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? O14 C24 1.376(11) . ? O14 C54 1.54(3) . ? C24 C34 1.398(18) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C34 C44 1.484(16) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C44 C54 1.330(15) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? O17 C27 1.398(19) . ? O17 C57 1.56(3) . ? C27 C37 1.40(2) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C37 C47 1.48(2) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C47 C57 1.35(2) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C57 H57A 0.9900 . ? C57 H57B 0.9900 . ? O15 C25 1.391(15) . ? O15 C55 1.56(2) . ? C25 C35 1.404(17) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C35 C45 1.447(19) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C45 C55 1.389(19) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C55 H55A 0.9900 . ? C55 H55B 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 C626 C616 C666 121(2) . . ? C626 C616 C66 119(2) . . ? C666 C616 C66 119(2) . . ? C616 C626 C636 118.5(19) . . ? C616 C626 Cl16 120.1(19) . . ? C636 C626 Cl16 121.3(18) . . ? C646 C636 C626 120(2) . . ? C646 C636 Cl26 120.9(19) . . ? C626 C636 Cl26 118.6(18) . . ? C636 C646 C656 121(2) . . ? C636 C646 H646 119.3 . . ? C656 C646 H646 119.3 . . ? C646 C656 C666 118(2) . . ? C646 C656 H656 121.0 . . ? C666 C656 H656 121.0 . . ? C656 C666 C616 121(2) . . ? C656 C666 H666 119.7 . . ? C616 C666 H666 119.7 . . ? C66 N16 N26 117(2) . . ? C36 N26 N16 122(2) . . ? C36 N26 H26 118.9 . . ? N16 N26 H26 118.9 . . ? N36 C36 N46 120(2) . . ? N36 C36 N26 118(2) . . ? N46 C36 N26 122(2) . . ? C56 N46 C36 117(2) . . ? N56 C56 N46 122(2) . . ? N56 C56 C66 119(2) . . ? N46 C56 C66 119(2) . . ? N16 C66 C56 122(2) . . ? N16 C66 C616 114(3) . . ? C56 C66 C616 124(3) . . ? C36 N36 H36A 120.0 . . ? C36 N36 H36B 120.0 . . ? H36A N36 H36B 120.0 . . ? C36 N36 H31A 117.6 . . ? H36A N36 H31A 16.6 . . ? H36B N36 H31A 119.7 . . ? C36 N36 H31B 115.5 . . ? H36A N36 H31B 124.4 . . ? H36B N36 H31B 5.1 . . ? H31A N36 H31B 122.9 . . ? C56 N56 H56A 120.0 . . ? C56 N56 H56B 120.0 . . ? H56A N56 H56B 120.0 . . ? C61 N11 N21 117.4 . . ? N11 N21 C31 122.0 . . ? N11 N21 H21 119.0 . . ? C31 N21 H21 119.0 . . ? N31 C31 N41 120.9 . . ? N31 C31 N21 116.7 . . ? N41 C31 N21 122.4 . . ? C51 N41 C31 117.2 . . ? N51 C51 N41 119.17(19) . . ? N51 C51 C61 121.14(19) . . ? N41 C51 C61 119.7 . . ? N11 C61 C51 121.2 . . ? N11 C61 C611 117.07(17) . . ? C51 C61 C611 121.68(17) . . ? 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 . . ? C621 C611 C661 119.4(4) . . ? C621 C611 C61 121.0(3) . . ? C661 C611 C61 119.6(4) . . ? C611 C621 C631 120.1(4) . . ? C611 C621 Cl11 120.2(3) . . ? C631 C621 Cl11 119.8(3) . . ? C641 C631 C621 120.2(4) . . ? C641 C631 Cl21 119.8(4) . . ? C621 C631 Cl21 120.0(4) . . ? C631 C641 C651 119.9(4) . . ? C631 C641 H641 120.0 . . ? C651 C641 H641 120.0 . . ? C641 C651 C661 120.2(5) . . ? C641 C651 H651 119.9 . . ? C661 C651 H651 119.9 . . ? C651 C661 C611 120.1(4) . . ? C651 C661 H661 119.9 . . ? C611 C661 H661 119.9 . . ? C62 N12 N22 117.8(3) . . ? N12 N22 C32 122.3(3) . . ? N12 N22 H22 118.9 . . ? C32 N22 H22 118.9 . . ? N32 C32 N42 120.5(4) . . ? N32 C32 N22 117.7(4) . . ? N42 C32 N22 121.8(4) . . ? C32 N32 H32A 120.0 . . ? C32 N32 H32B 120.0 . . ? H32A N32 H32B 120.0 . . ? C52 N42 C32 117.5(3) . . ? N52 C52 N42 119.3(4) . . ? N52 C52 C62 120.8(4) . . ? N42 C52 C62 119.9(4) . . ? C52 N52 H52A 120.0 . . ? C52 N52 H52B 120.0 . . ? H52A N52 H52B 120.0 . . ? N12 C62 C52 120.6(4) . . ? N12 C62 C612 117.0(4) . . ? C52 C62 C612 122.4(4) . . ? C622 C612 C662 122.1(4) . . ? C622 C612 C62 119.3(4) . . ? C662 C612 C62 118.6(4) . . ? C612 C622 C632 119.0(5) . . ? C612 C622 Cl12 120.2(4) . . ? C632 C622 Cl12 120.7(4) . . ? C642 C632 C622 119.1(5) . . ? C642 C632 Cl22 121.1(4) . . ? C622 C632 Cl22 119.8(5) . . ? C652 C642 C632 121.6(5) . . ? C652 C642 H642 119.2 . . ? C632 C642 H642 119.2 . . ? C642 C652 C662 122.2(5) . . ? C642 C652 H652 118.9 . . ? C662 C652 H652 118.9 . . ? C652 C662 C612 115.9(5) . . ? C652 C662 H662 122.0 . . ? C612 C662 H662 122.0 . . ? O13 C13 O23 123.6(4) . . ? O13 C13 C23 119.0(4) . . ? O23 C13 C23 117.3(3) . . ? C13 C23 C33 113.9(4) . . ? C13 C23 H23A 108.8 . . ? C33 C23 H23A 108.8 . . ? C13 C23 H23B 108.8 . . ? C33 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? C43 C33 C23 114.3(4) . . ? C43 C33 H33A 108.7 . . ? C23 C33 H33A 108.7 . . ? C43 C33 H33B 108.7 . . ? C23 C33 H33B 108.7 . . ? H33A C33 H33B 107.6 . . ? C33 C43 C53 111.8(4) . . ? C33 C43 H43A 109.3 . . ? C53 C43 H43A 109.3 . . ? C33 C43 H43B 109.3 . . ? C53 C43 H43B 109.3 . . ? H43A C43 H43B 107.9 . . ? C63 C53 C43 112.6(4) . . ? C63 C53 H53A 109.1 . . ? C43 C53 H53A 109.1 . . ? C63 C53 H53B 109.1 . . ? C43 C53 H53B 109.1 . . ? H53A C53 H53B 107.8 . . ? C73 C63 C53 113.8(3) . . ? C73 C63 H63A 108.8 . . ? C53 C63 H63A 108.8 . . ? C73 C63 H63B 108.8 . . ? C53 C63 H63B 108.8 . . ? H63A C63 H63B 107.7 . . ? O33 C73 O43 122.8(4) . . ? O33 C73 C63 120.1(4) . . ? O43 C73 C63 117.1(4) . . ? C24 O14 C54 101.8(11) . . ? O14 C24 C34 105.8(13) . . ? O14 C24 H24A 110.6 . . ? C34 C24 H24A 110.6 . . ? O14 C24 H24B 110.6 . . ? C34 C24 H24B 110.6 . . ? H24A C24 H24B 108.7 . . ? C24 C34 C44 108.1(13) . . ? C24 C34 H34A 110.1 . . ? C44 C34 H34A 110.1 . . ? C24 C34 H34B 110.1 . . ? C44 C34 H34B 110.1 . . ? H34A C34 H34B 108.4 . . ? C54 C44 C34 104.2(11) . . ? C54 C44 H44A 110.9 . . ? C34 C44 H44A 110.9 . . ? C54 C44 H44B 110.9 . . ? C34 C44 H44B 110.9 . . ? H44A C44 H44B 108.9 . . ? C44 C54 O14 103.9(15) . . ? C44 C54 H54A 111.0 . . ? O14 C54 H54A 111.0 . . ? C44 C54 H54B 111.0 . . ? O14 C54 H54B 111.0 . . ? H54A C54 H54B 109.0 . . ? C27 O17 C57 96(2) . . ? C37 C27 O17 105(2) . . ? C37 C27 H27A 110.7 . . ? O17 C27 H27A 110.7 . . ? C37 C27 H27B 110.7 . . ? O17 C27 H27B 110.7 . . ? H27A C27 H27B 108.8 . . ? C27 C37 C47 107(2) . . ? C27 C37 H37A 110.3 . . ? C47 C37 H37A 110.3 . . ? C27 C37 H37B 110.3 . . ? C47 C37 H37B 110.3 . . ? H37A C37 H37B 108.6 . . ? C57 C47 C37 98(2) . . ? C57 C47 H47A 112.2 . . ? C37 C47 H47A 112.2 . . ? C57 C47 H47B 112.2 . . ? C37 C47 H47B 112.2 . . ? H47A C47 H47B 109.8 . . ? C47 C57 O17 98(3) . . ? C47 C57 H57A 112.1 . . ? O17 C57 H57A 112.1 . . ? C47 C57 H57B 112.1 . . ? O17 C57 H57B 112.1 . . ? H57A C57 H57B 109.7 . . ? C25 O15 C55 91.7(13) . . ? C35 C25 O15 106.0(12) . . ? C35 C25 H25A 110.5 . . ? O15 C25 H25A 110.5 . . ? C35 C25 H25B 110.5 . . ? O15 C25 H25B 110.5 . . ? H25A C25 H25B 108.7 . . ? C25 C35 C45 104.8(12) . . ? C25 C35 H35A 110.8 . . ? C45 C35 H35A 110.8 . . ? C25 C35 H35B 110.8 . . ? C45 C35 H35B 110.8 . . ? H35A C35 H35B 108.9 . . ? C55 C45 C35 90.6(16) . . ? C55 C45 H45A 113.5 . . ? C35 C45 H45A 113.5 . . ? C55 C45 H45B 113.5 . . ? C35 C45 H45B 113.5 . . ? H45A C45 H45B 110.8 . . ? C45 C55 O15 94.2(15) . . ? C45 C55 H55A 112.9 . . ? O15 C55 H55A 112.9 . . ? C45 C55 H55B 112.9 . . ? O15 C55 H55B 112.9 . . ? H55A C55 H55B 110.3 . . ? 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 C666 C616 C626 C636 -5(10) . . . . ? C66 C616 C626 C636 -171(5) . . . . ? C666 C616 C626 Cl16 178(5) . . . . ? C66 C616 C626 Cl16 13(8) . . . . ? C616 C626 C636 C646 0(11) . . . . ? Cl16 C626 C636 C646 176(7) . . . . ? C616 C626 C636 Cl26 -175(5) . . . . ? Cl16 C626 C636 Cl26 2(8) . . . . ? C626 C636 C646 C656 7(14) . . . . ? Cl26 C636 C646 C656 -178(7) . . . . ? C636 C646 C656 C666 -9(14) . . . . ? C646 C656 C666 C616 3(11) . . . . ? C626 C616 C666 C656 4(10) . . . . ? C66 C616 C666 C656 169(5) . . . . ? C66 N16 N26 C36 0(2) . . . . ? N16 N26 C36 N36 180(2) . . . . ? N16 N26 C36 N46 4(4) . . . . ? N36 C36 N46 C56 177(3) . . . . ? N26 C36 N46 C56 -6(4) . . . . ? C36 N46 C56 N56 -174(3) . . . . ? C36 N46 C56 C66 6(4) . . . . ? N26 N16 C66 C56 0(3) . . . . ? N26 N16 C66 C616 -179.8(13) . . . . ? N56 C56 C66 N16 178(3) . . . . ? N46 C56 C66 N16 -3(5) . . . . ? N56 C56 C66 C616 -3(5) . . . . ? N46 C56 C66 C616 177(3) . . . . ? C626 C616 C66 N16 -100(6) . . . . ? C666 C616 C66 N16 94(6) . . . . ? C626 C616 C66 C56 80(6) . . . . ? C666 C616 C66 C56 -86(6) . . . . ? C61 N11 N21 C31 0.9 . . . . ? N11 N21 C31 N31 -179.0 . . . . ? N11 N21 C31 N41 -0.3 . . . . ? N31 C31 N41 C51 178.1 . . . . ? N21 C31 N41 C51 -0.5 . . . . ? C31 N41 C51 N51 -178.1(2) . . . . ? C31 N41 C51 C61 0.7 . . . . ? N21 N11 C61 C51 -0.6 . . . . ? N21 N11 C61 C611 179.05(19) . . . . ? N51 C51 C61 N11 178.6(2) . . . . ? N41 C51 C61 N11 -0.1 . . . . ? N51 C51 C61 C611 -1.0(3) . . . . ? N41 C51 C61 C611 -179.8(2) . . . . ? N11 C61 C611 C621 108.5(3) . . . . ? C51 C61 C611 C621 -71.8(4) . . . . ? N11 C61 C611 C661 -71.8(4) . . . . ? C51 C61 C611 C661 107.9(3) . . . . ? C661 C611 C621 C631 0.6(7) . . . . ? C61 C611 C621 C631 -179.7(4) . . . . ? C661 C611 C621 Cl11 -179.5(3) . . . . ? C61 C611 C621 Cl11 0.2(5) . . . . ? C611 C621 C631 C641 0.8(8) . . . . ? Cl11 C621 C631 C641 -179.0(4) . . . . ? C611 C621 C631 Cl21 -178.9(4) . . . . ? Cl11 C621 C631 Cl21 1.2(6) . . . . ? C621 C631 C641 C651 -1.7(8) . . . . ? Cl21 C631 C641 C651 178.0(4) . . . . ? C631 C641 C651 C661 1.2(8) . . . . ? C641 C651 C661 C611 0.2(7) . . . . ? C621 C611 C661 C651 -1.1(7) . . . . ? C61 C611 C661 C651 179.2(4) . . . . ? C62 N12 N22 C32 -1.2(7) . . . . ? N12 N22 C32 N32 -179.7(4) . . . . ? N12 N22 C32 N42 -0.1(7) . . . . ? N32 C32 N42 C52 -178.5(4) . . . . ? N22 C32 N42 C52 1.9(7) . . . . ? C32 N42 C52 N52 178.7(4) . . . . ? C32 N42 C52 C62 -2.4(7) . . . . ? N22 N12 C62 C52 0.6(7) . . . . ? N22 N12 C62 C612 179.5(4) . . . . ? N52 C52 C62 N12 -179.9(5) . . . . ? N42 C52 C62 N12 1.2(7) . . . . ? N52 C52 C62 C612 1.2(7) . . . . ? N42 C52 C62 C612 -177.7(4) . . . . ? N12 C62 C612 C622 99.8(5) . . . . ? C52 C62 C612 C622 -81.4(6) . . . . ? N12 C62 C612 C662 -78.9(5) . . . . ? C52 C62 C612 C662 100.0(5) . . . . ? C662 C612 C622 C632 2.2(6) . . . . ? C62 C612 C622 C632 -176.4(4) . . . . ? C662 C612 C622 Cl12 -179.3(3) . . . . ? C62 C612 C622 Cl12 2.1(6) . . . . ? C612 C622 C632 C642 -1.3(6) . . . . ? Cl12 C622 C632 C642 -179.8(4) . . . . ? C612 C622 C632 Cl22 178.6(3) . . . . ? Cl12 C622 C632 Cl22 0.1(5) . . . . ? C622 C632 C642 C652 -0.2(7) . . . . ? Cl22 C632 C642 C652 180.0(4) . . . . ? C632 C642 C652 C662 0.7(8) . . . . ? C642 C652 C662 C612 0.2(7) . . . . ? C622 C612 C662 C652 -1.6(6) . . . . ? C62 C612 C662 C652 177.0(4) . . . . ? O13 C13 C23 C33 -26.0(6) . . . . ? O23 C13 C23 C33 155.9(4) . . . . ? C13 C23 C33 C43 171.9(4) . . . . ? C23 C33 C43 C53 173.1(4) . . . . ? C33 C43 C53 C63 164.7(4) . . . . ? C43 C53 C63 C73 -68.9(5) . . . . ? C53 C63 C73 O33 141.0(4) . . . . ? C53 C63 C73 O43 -39.6(6) . . . . ? C54 O14 C24 C34 -32(2) . . . . ? O14 C24 C34 C44 15(3) . . . . ? C24 C34 C44 C54 13(4) . . . . ? C34 C44 C54 O14 -31(3) . . . . ? C24 O14 C54 C44 41(3) . . . . ? C57 O17 C27 C37 37(6) . . . . ? O17 C27 C37 C47 -7(8) . . . . ? C27 C37 C47 C57 -31(8) . . . . ? C37 C47 C57 O17 52(6) . . . . ? C27 O17 C57 C47 -58(4) . . . . ? C55 O15 C25 C35 33(2) . . . . ? O15 C25 C35 C45 5(3) . . . . ? C25 C35 C45 C55 -47(3) . . . . ? C35 C45 C55 O15 66(2) . . . . ? C25 O15 C55 C45 -65(2) . . . . ? 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 O23 0.88 1.87 2.735(3) 166.3 2_665 N31 H31A O13 0.88 2.10 2.871(4) 145.7 . N31 H31B O13 0.88 1.89 2.770(3) 175.5 2_665 N51 H51A O43 0.88 2.02 2.857(5) 158.4 . N51 H51B O33 0.88 2.06 2.903(5) 161.0 2_676 N22 H22 O43 0.88 1.72 2.577(4) 162.3 2_666 N22 H22 O33 0.88 2.61 3.318(4) 138.6 2_666 N32 H32A O23 0.88 2.19 3.061(4) 171.2 1_445 N32 H32B O33 0.88 1.98 2.839(5) 163.9 2_666 N52 H52A N42 0.88 2.08 2.948(5) 170.4 2 N52 H52B O23 0.88 2.16 2.865(5) 137.2 2_665 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.032 _refine_diff_density_min -0.662 _refine_diff_density_rms 0.075