# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Andrew Bond' _publ_contact_author_address ; Department of Chemistry University of Southern Denmark Campusvej 55 5230 Odense M DK-5230 DENMARK ; _publ_contact_author_email ADB@CHEM.SDU.DK _publ_section_title ; Hydrogen-bonded cubanes and ladder fragments by analogy with the inorganic solid state ; loop_ _publ_author_name 'Andrew Bond' 'Wendie H. Jorgensen' 'Jane M. Ploger' #====================================================================== data_1 _database_code_depnum_ccdc_archive 'CCDC 645313' _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 N +, Cl -, 0.125(C7 H8)' _chemical_formula_sum 'C19.88 H19 Cl N' _chemical_formula_weight 307.31 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 34.700(2) _cell_length_b 14.7258(9) _cell_length_c 28.107(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.850(3) _cell_angle_gamma 90.00 _cell_volume 13944.7(15) _cell_formula_units_Z 32 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7580 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 21.63 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5192 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.383 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.393286 Crystals are very sensitive to solvent loss. The necessary rapid mounting resulted in a non-optimal position on the glass fibre. The multi-scan correction is likely to be correcting for the systematic error associated with absorption by the fibre. ; _exptl_special_details ; Diffraction was relatively weak: 5951 out of 9983 unique reflections are observed at the 2\s(I) level to 2\q = 23.26\%. There are no observable data beyond this resolution. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay ? _diffrn_reflns_number 61797 _diffrn_reflns_av_R_equivalents 0.0843 _diffrn_reflns_av_sigmaI/netI 0.0909 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 23.26 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 9983 _reflns_number_gt 5951 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-22 (Bruker Nonius, 2004)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10' _computing_molecular_graphics 'SHELXTL v.6.10' _computing_publication_material 'SHELXTL v.6.10' _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^)+(0.1076P)^2^+14.0640P] 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 9983 _refine_ls_number_parameters 777 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1236 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.1999 _refine_ls_wR_factor_gt 0.1692 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.402 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.073 # difference peak associated with toluene molecule # disordered about a centre of inversion 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 Cl1 Cl 0.42596(3) 0.43848(7) 0.43618(4) 0.0359(3) Uani 1 1 d . . . Cl2 Cl 0.30337(3) 0.31383(7) 0.42980(4) 0.0369(3) Uani 1 1 d . . . Cl3 Cl 0.31444(3) 0.53700(7) 0.32587(4) 0.0368(3) Uani 1 1 d . . . Cl4 Cl 0.33079(3) 0.58928(8) 0.48032(4) 0.0378(3) Uani 1 1 d . . . N1 N 0.35759(9) 0.3497(2) 0.35757(12) 0.0298(8) Uani 1 1 d . . . H1A H 0.3817 0.3627 0.3775 0.045 Uiso 1 1 calc R . . H1B H 0.3414 0.3270 0.3758 0.045 Uiso 1 1 calc R . . H1C H 0.3467 0.4012 0.3421 0.045 Uiso 1 1 calc R . . C1 C 0.36248(12) 0.2800(3) 0.31977(14) 0.0302(11) Uani 1 1 d . . . C2 C 0.38777(12) 0.2021(3) 0.34669(15) 0.0321(11) Uani 1 1 d . . . C3 C 0.41651(14) 0.1601(3) 0.32757(18) 0.0464(13) Uani 1 1 d . . . H3A H 0.4220 0.1828 0.2983 0.056 Uiso 1 1 calc R . . C4 C 0.43722(15) 0.0858(4) 0.3503(2) 0.0574(15) Uani 1 1 d . . . H4A H 0.4563 0.0573 0.3361 0.069 Uiso 1 1 calc R . . C5 C 0.43053(14) 0.0527(3) 0.3931(2) 0.0505(14) Uani 1 1 d . . . H5A H 0.4452 0.0022 0.4089 0.061 Uiso 1 1 calc R . . C6 C 0.40208(14) 0.0939(3) 0.41309(17) 0.0467(13) Uani 1 1 d . . . H6A H 0.3969 0.0709 0.4425 0.056 Uiso 1 1 calc R . . C7 C 0.38145(13) 0.1676(3) 0.39043(16) 0.0402(12) Uani 1 1 d . . . H7A H 0.3624 0.1958 0.4048 0.048 Uiso 1 1 calc R . . C8 C 0.38301(12) 0.3267(3) 0.28376(15) 0.0309(11) Uani 1 1 d . . . C9 C 0.37103(13) 0.3112(3) 0.23396(16) 0.0424(12) Uani 1 1 d . . . H9A H 0.3484 0.2744 0.2213 0.051 Uiso 1 1 calc R . . C10 C 0.39174(15) 0.3492(3) 0.20221(17) 0.0489(13) Uani 1 1 d . . . H10A H 0.3833 0.3375 0.1680 0.059 Uiso 1 1 calc R . . C11 C 0.42401(14) 0.4030(3) 0.21965(17) 0.0465(13) Uani 1 1 d . . . H11A H 0.4381 0.4285 0.1977 0.056 Uiso 1 1 calc R . . C12 C 0.43615(14) 0.4202(3) 0.26898(18) 0.0477(13) Uani 1 1 d . . . H12A H 0.4584 0.4582 0.2812 0.057 Uiso 1 1 calc R . . C13 C 0.41589(14) 0.3819(3) 0.30108(16) 0.0426(12) Uani 1 1 d . . . H13A H 0.4246 0.3936 0.3352 0.051 Uiso 1 1 calc R . . C14 C 0.32005(13) 0.2483(3) 0.29480(15) 0.0332(11) Uani 1 1 d . . . C15 C 0.31073(14) 0.1578(3) 0.28599(16) 0.0429(12) Uani 1 1 d . . . H15A H 0.3308 0.1129 0.2951 0.052 Uiso 1 1 calc R . . C16 C 0.27201(16) 0.1322(4) 0.26382(18) 0.0534(14) Uani 1 1 d . . . H16A H 0.2658 0.0697 0.2582 0.064 Uiso 1 1 calc R . . C17 C 0.24244(15) 0.1965(4) 0.24991(17) 0.0533(14) Uani 1 1 d . . . H17A H 0.2160 0.1787 0.2349 0.064 Uiso 1 1 calc R . . C18 C 0.25192(15) 0.2862(4) 0.25809(18) 0.0536(14) Uani 1 1 d . . . H18A H 0.2319 0.3311 0.2485 0.064 Uiso 1 1 calc R . . C19 C 0.29022(13) 0.3121(3) 0.28006(16) 0.0422(12) Uani 1 1 d . . . H19A H 0.2963 0.3748 0.2852 0.051 Uiso 1 1 calc R . . N2 N 0.26020(9) 0.5034(2) 0.40092(12) 0.0342(9) Uani 1 1 d . . . H2A H 0.2650 0.5158 0.3712 0.051 Uiso 1 1 calc R . . H2B H 0.2647 0.4434 0.4079 0.051 Uiso 1 1 calc R . . H2C H 0.2766 0.5374 0.4243 0.051 Uiso 1 1 calc R . . C21 C 0.21693(12) 0.5263(3) 0.39986(15) 0.0335(11) Uani 1 1 d . . . C22 C 0.21267(12) 0.6289(3) 0.39850(15) 0.0356(11) Uani 1 1 d . . . C23 C 0.19138(15) 0.6740(3) 0.42717(17) 0.0526(14) Uani 1 1 d . . . H23A H 0.1803 0.6408 0.4496 0.063 Uiso 1 1 calc R . . C24 C 0.18612(18) 0.7675(4) 0.4233(2) 0.0689(17) Uani 1 1 d . . . H24A H 0.1725 0.7979 0.4442 0.083 Uiso 1 1 calc R . . C25 C 0.20031(17) 0.8161(4) 0.3899(2) 0.0622(16) Uani 1 1 d . . . H25A H 0.1958 0.8797 0.3866 0.075 Uiso 1 1 calc R . . C26 C 0.22125(15) 0.7724(4) 0.36088(19) 0.0534(14) Uani 1 1 d . . . H26A H 0.2314 0.8060 0.3377 0.064 Uiso 1 1 calc R . . C27 C 0.22763(13) 0.6806(3) 0.36528(17) 0.0430(12) Uani 1 1 d . . . H27A H 0.2425 0.6515 0.3453 0.052 Uiso 1 1 calc R . . C28 C 0.18996(13) 0.4817(3) 0.35469(16) 0.0356(11) Uani 1 1 d . . . C29 C 0.15711(14) 0.5279(3) 0.32735(17) 0.0461(13) Uani 1 1 d . . . H29A H 0.1533 0.5901 0.3340 0.055 Uiso 1 1 calc R . . C210 C 0.12984(15) 0.4835(4) 0.29041(18) 0.0560(15) Uani 1 1 d . . . H21A H 0.1074 0.5155 0.2721 0.067 Uiso 1 1 calc R . . C211 C 0.13513(17) 0.3939(4) 0.28015(18) 0.0575(15) Uani 1 1 d . . . H21B H 0.1161 0.3633 0.2554 0.069 Uiso 1 1 calc R . . C212 C 0.16826(16) 0.3488(4) 0.30615(19) 0.0555(14) Uani 1 1 d . . . H21C H 0.1725 0.2873 0.2986 0.067 Uiso 1 1 calc R . . C213 C 0.19541(14) 0.3925(3) 0.34310(18) 0.0472(13) Uani 1 1 d . . . H21D H 0.2181 0.3605 0.3607 0.057 Uiso 1 1 calc R . . C214 C 0.20904(13) 0.4861(3) 0.44747(16) 0.0337(11) Uani 1 1 d . . . C215 C 0.17614(15) 0.4351(3) 0.44796(18) 0.0513(14) Uani 1 1 d . . . H21E H 0.1577 0.4212 0.4180 0.062 Uiso 1 1 calc R . . C216 C 0.16935(17) 0.4034(4) 0.4920(2) 0.0612(16) Uani 1 1 d . . . H21F H 0.1465 0.3679 0.4920 0.073 Uiso 1 1 calc R . . C217 C 0.19564(17) 0.4234(3) 0.5351(2) 0.0542(14) Uani 1 1 d . . . H21G H 0.1911 0.4011 0.5650 0.065 Uiso 1 1 calc R . . C218 C 0.22848(14) 0.4753(3) 0.53582(17) 0.0446(13) Uani 1 1 d . . . H21H H 0.2465 0.4897 0.5661 0.054 Uiso 1 1 calc R . . C219 C 0.23534(13) 0.5070(3) 0.49187(17) 0.0401(12) Uani 1 1 d . . . H21I H 0.2581 0.5431 0.4922 0.048 Uiso 1 1 calc R . . N3 N 0.37258(10) 0.4017(2) 0.51197(11) 0.0322(9) Uani 1 1 d . . . H3B H 0.3927 0.4047 0.4964 0.048 Uiso 1 1 calc R . . H3C H 0.3600 0.4563 0.5096 0.048 Uiso 1 1 calc R . . H3D H 0.3550 0.3580 0.4977 0.048 Uiso 1 1 calc R . . C31 C 0.38934(12) 0.3784(3) 0.56589(14) 0.0331(11) Uani 1 1 d . . . C32 C 0.35418(12) 0.3811(3) 0.59063(15) 0.0318(11) Uani 1 1 d . . . C33 C 0.35695(14) 0.4260(3) 0.63495(16) 0.0421(12) Uani 1 1 d . . . H33A H 0.3799 0.4609 0.6491 0.050 Uiso 1 1 calc R . . C34 C 0.32584(16) 0.4196(4) 0.65856(18) 0.0543(14) Uani 1 1 d . . . H34A H 0.3277 0.4505 0.6887 0.065 Uiso 1 1 calc R . . C35 C 0.29258(16) 0.3688(4) 0.6384(2) 0.0572(15) Uani 1 1 d . . . H35A H 0.2716 0.3642 0.6547 0.069 Uiso 1 1 calc R . . C36 C 0.28986(14) 0.3252(4) 0.5949(2) 0.0521(14) Uani 1 1 d . . . H36A H 0.2668 0.2908 0.5808 0.063 Uiso 1 1 calc R . . C37 C 0.32042(13) 0.3303(3) 0.57078(17) 0.0410(12) Uani 1 1 d . . . H37A H 0.3182 0.2990 0.5407 0.049 Uiso 1 1 calc R . . C38 C 0.42124(12) 0.4505(3) 0.58534(14) 0.0305(11) Uani 1 1 d . . . C39 C 0.41172(14) 0.5418(3) 0.58076(15) 0.0373(12) Uani 1 1 d . . . H39A H 0.3851 0.5594 0.5668 0.045 Uiso 1 1 calc R . . C310 C 0.44034(15) 0.6080(3) 0.59617(16) 0.0460(13) Uani 1 1 d . . . H31A H 0.4333 0.6704 0.5928 0.055 Uiso 1 1 calc R . . C311 C 0.47958(15) 0.5830(4) 0.61666(17) 0.0497(14) Uani 1 1 d . . . H31B H 0.4994 0.6281 0.6268 0.060 Uiso 1 1 calc R . . C312 C 0.48909(14) 0.4928(4) 0.62198(18) 0.0497(14) Uani 1 1 d . . . H31C H 0.5157 0.4752 0.6363 0.060 Uiso 1 1 calc R . . C313 C 0.46022(13) 0.4264(3) 0.60657(17) 0.0427(12) Uani 1 1 d . . . H31D H 0.4673 0.3641 0.6106 0.051 Uiso 1 1 calc R . . C314 C 0.40693(12) 0.2825(3) 0.56984(15) 0.0320(11) Uani 1 1 d . . . C315 C 0.40596(13) 0.2286(3) 0.60977(16) 0.0409(12) Uani 1 1 d . . . H31E H 0.3926 0.2496 0.6335 0.049 Uiso 1 1 calc R . . C316 C 0.42421(14) 0.1443(3) 0.61565(18) 0.0501(13) Uani 1 1 d . . . H31F H 0.4230 0.1077 0.6431 0.060 Uiso 1 1 calc R . . C317 C 0.44403(14) 0.1134(3) 0.5822(2) 0.0504(13) Uani 1 1 d . . . H31G H 0.4568 0.0558 0.5865 0.061 Uiso 1 1 calc R . . C318 C 0.44537(15) 0.1664(3) 0.54205(19) 0.0520(14) Uani 1 1 d . . . H31H H 0.4589 0.1451 0.5186 0.062 Uiso 1 1 calc R . . C319 C 0.42718(13) 0.2499(3) 0.53607(17) 0.0411(12) Uani 1 1 d . . . H31I H 0.4284 0.2861 0.5085 0.049 Uiso 1 1 calc R . . N4 N 0.38270(10) 0.6283(2) 0.40588(12) 0.0330(9) Uani 1 1 d . . . H4B H 0.3640 0.6132 0.3784 0.050 Uiso 1 1 calc R . . H4C H 0.3712 0.6325 0.4317 0.050 Uiso 1 1 calc R . . H4D H 0.4019 0.5847 0.4121 0.050 Uiso 1 1 calc R . . C41 C 0.40122(12) 0.7192(3) 0.39816(15) 0.0333(11) Uani 1 1 d . . . C42 C 0.36763(12) 0.7886(3) 0.38509(16) 0.0342(11) Uani 1 1 d . . . C43 C 0.33994(14) 0.7953(3) 0.41374(19) 0.0493(13) Uani 1 1 d . . . H43A H 0.3412 0.7541 0.4400 0.059 Uiso 1 1 calc R . . C44 C 0.31113(15) 0.8603(4) 0.4045(2) 0.0562(14) Uani 1 1 d . . . H44A H 0.2927 0.8639 0.4245 0.067 Uiso 1 1 calc R . . C45 C 0.30846(15) 0.9212(4) 0.3662(2) 0.0576(15) Uani 1 1 d . . . H45A H 0.2883 0.9664 0.3599 0.069 Uiso 1 1 calc R . . C46 C 0.33547(17) 0.9151(3) 0.33739(19) 0.0585(15) Uani 1 1 d . . . H46A H 0.3340 0.9559 0.3108 0.070 Uiso 1 1 calc R . . C47 C 0.36462(15) 0.8495(3) 0.34733(17) 0.0457(13) Uani 1 1 d . . . H47A H 0.3832 0.8463 0.3275 0.055 Uiso 1 1 calc R . . C48 C 0.43108(12) 0.7420(3) 0.44644(15) 0.0339(11) Uani 1 1 d . . . C49 C 0.45996(13) 0.6791(3) 0.46823(17) 0.0415(12) Uani 1 1 d . . . H49A H 0.4609 0.6219 0.4529 0.050 Uiso 1 1 calc R . . C410 C 0.48699(14) 0.6981(4) 0.51133(18) 0.0507(14) Uani 1 1 d . . . H41A H 0.5059 0.6534 0.5259 0.061 Uiso 1 1 calc R . . C411 C 0.48708(16) 0.7816(4) 0.53366(19) 0.0577(15) Uani 1 1 d . . . H41B H 0.5061 0.7950 0.5632 0.069 Uiso 1 1 calc R . . C412 C 0.45916(17) 0.8447(4) 0.5123(2) 0.0599(15) Uani 1 1 d . . . H41C H 0.4589 0.9023 0.5275 0.072 Uiso 1 1 calc R . . C413 C 0.43115(14) 0.8260(3) 0.46883(17) 0.0454(13) Uani 1 1 d . . . H41D H 0.4121 0.8707 0.4546 0.054 Uiso 1 1 calc R . . C414 C 0.42164(12) 0.7079(3) 0.35549(15) 0.0329(11) Uani 1 1 d . . . C415 C 0.45683(13) 0.7519(3) 0.35536(17) 0.0457(13) Uani 1 1 d . . . H41E H 0.4705 0.7832 0.3840 0.055 Uiso 1 1 calc R . . C416 C 0.47242(15) 0.7512(4) 0.31474(19) 0.0595(15) Uani 1 1 d . . . H41F H 0.4964 0.7827 0.3152 0.071 Uiso 1 1 calc R . . C417 C 0.45337(15) 0.7052(4) 0.27386(19) 0.0586(15) Uani 1 1 d . . . H41G H 0.4642 0.7046 0.2459 0.070 Uiso 1 1 calc R . . C418 C 0.41857(15) 0.6595(3) 0.27273(17) 0.0503(14) Uani 1 1 d . . . H41H H 0.4056 0.6271 0.2442 0.060 Uiso 1 1 calc R . . C419 C 0.40255(14) 0.6609(3) 0.31345(16) 0.0421(12) Uani 1 1 d . . . H41I H 0.3784 0.6297 0.3126 0.051 Uiso 1 1 calc R . . C1S C 0.01342(15) 0.5253(4) 0.27181(12) 0.098(2) Uiso 1 1 d D . . H1SA H 0.0234 0.4699 0.2873 0.117 Uiso 1 1 calc R . . C2S C 0.0131(2) 0.6863(4) 0.27201(16) 0.155(4) Uiso 1 1 d D . . H2SA H 0.0224 0.7418 0.2879 0.186 Uiso 1 1 calc R . . C3S C 0.02582(14) 0.6059(4) 0.29298(12) 0.142(3) Uiso 1 1 d D . . H3S H 0.0443 0.6059 0.3240 0.170 Uiso 0.50 1 calc PR . . C4S C 0.0549(4) 0.6060(4) 0.3419(3) 0.229(12) Uiso 0.50 1 d PD . . H4SA H 0.0609 0.6675 0.3525 0.344 Uiso 0.50 1 d PR . . H4SB H 0.0433 0.5750 0.3651 0.344 Uiso 0.50 1 d PR . . H4SC H 0.0789 0.5756 0.3398 0.344 Uiso 0.50 1 d PR . . 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 Cl1 0.0388(6) 0.0467(7) 0.0240(7) 0.0008(5) 0.0107(5) -0.0016(5) Cl2 0.0401(7) 0.0480(7) 0.0254(7) -0.0007(5) 0.0133(5) -0.0039(5) Cl3 0.0404(7) 0.0451(7) 0.0269(7) 0.0035(5) 0.0124(5) 0.0003(5) Cl4 0.0426(7) 0.0499(7) 0.0243(7) 0.0004(5) 0.0146(5) -0.0024(5) N1 0.034(2) 0.039(2) 0.020(2) -0.0015(17) 0.0125(16) -0.0018(16) C1 0.035(3) 0.041(3) 0.016(2) -0.006(2) 0.008(2) 0.000(2) C2 0.039(3) 0.035(3) 0.025(3) -0.001(2) 0.015(2) 0.000(2) C3 0.058(3) 0.048(3) 0.042(3) 0.005(3) 0.028(3) 0.008(3) C4 0.060(3) 0.061(4) 0.060(4) 0.006(3) 0.033(3) 0.020(3) C5 0.051(3) 0.047(3) 0.052(4) 0.006(3) 0.010(3) 0.009(3) C6 0.058(3) 0.053(3) 0.030(3) 0.011(2) 0.013(3) 0.002(3) C7 0.053(3) 0.044(3) 0.028(3) 0.003(2) 0.019(2) 0.010(2) C8 0.036(3) 0.042(3) 0.016(3) 0.001(2) 0.008(2) 0.002(2) C9 0.044(3) 0.063(3) 0.020(3) -0.003(2) 0.007(2) -0.009(2) C10 0.060(3) 0.074(4) 0.014(3) 0.001(2) 0.012(2) -0.002(3) C11 0.052(3) 0.072(4) 0.020(3) 0.011(3) 0.019(2) 0.002(3) C12 0.051(3) 0.061(3) 0.035(3) 0.005(3) 0.019(3) -0.014(3) C13 0.054(3) 0.060(3) 0.016(3) -0.004(2) 0.012(2) -0.007(3) C14 0.042(3) 0.044(3) 0.018(3) -0.002(2) 0.015(2) -0.004(2) C15 0.054(3) 0.046(3) 0.032(3) -0.001(2) 0.015(2) -0.006(2) C16 0.060(4) 0.062(4) 0.038(3) -0.010(3) 0.013(3) -0.024(3) C17 0.045(3) 0.089(5) 0.026(3) -0.014(3) 0.010(2) -0.018(3) C18 0.046(3) 0.076(4) 0.038(3) -0.016(3) 0.010(3) 0.006(3) C19 0.040(3) 0.054(3) 0.030(3) -0.012(2) 0.003(2) -0.002(3) N2 0.039(2) 0.044(2) 0.024(2) 0.0002(17) 0.0163(17) -0.0008(17) C21 0.031(3) 0.050(3) 0.024(3) -0.001(2) 0.016(2) 0.000(2) C22 0.037(3) 0.049(3) 0.021(3) -0.003(2) 0.007(2) 0.005(2) C23 0.079(4) 0.055(4) 0.030(3) 0.003(3) 0.027(3) 0.016(3) C24 0.105(5) 0.069(4) 0.033(4) -0.010(3) 0.018(3) 0.032(4) C25 0.087(4) 0.047(3) 0.044(4) -0.001(3) -0.001(3) 0.011(3) C26 0.061(3) 0.054(4) 0.043(4) 0.004(3) 0.008(3) 0.001(3) C27 0.051(3) 0.047(3) 0.034(3) -0.001(2) 0.015(2) -0.001(2) C28 0.037(3) 0.054(3) 0.021(3) -0.001(2) 0.015(2) -0.005(2) C29 0.045(3) 0.059(3) 0.035(3) -0.002(3) 0.011(3) 0.001(3) C210 0.053(3) 0.078(4) 0.034(3) 0.005(3) 0.004(3) -0.006(3) C211 0.069(4) 0.082(5) 0.025(3) -0.018(3) 0.017(3) -0.020(3) C212 0.067(4) 0.067(4) 0.035(3) -0.013(3) 0.017(3) 0.003(3) C213 0.051(3) 0.053(4) 0.038(3) -0.010(3) 0.012(3) -0.004(3) C214 0.040(3) 0.042(3) 0.023(3) -0.002(2) 0.016(2) 0.002(2) C215 0.055(3) 0.071(4) 0.034(3) -0.015(3) 0.023(3) -0.020(3) C216 0.078(4) 0.073(4) 0.045(4) -0.015(3) 0.040(3) -0.030(3) C217 0.083(4) 0.056(3) 0.034(4) -0.001(3) 0.035(3) -0.009(3) C218 0.053(3) 0.060(3) 0.023(3) 0.004(2) 0.013(2) 0.000(3) C219 0.043(3) 0.052(3) 0.030(3) 0.003(2) 0.019(2) 0.000(2) N3 0.036(2) 0.046(2) 0.016(2) 0.0012(17) 0.0111(16) -0.0037(17) C31 0.043(3) 0.046(3) 0.012(3) 0.003(2) 0.010(2) -0.003(2) C32 0.034(3) 0.044(3) 0.020(3) 0.007(2) 0.011(2) 0.000(2) C33 0.047(3) 0.058(3) 0.025(3) 0.004(2) 0.016(2) 0.002(2) C34 0.063(4) 0.079(4) 0.030(3) 0.008(3) 0.028(3) 0.014(3) C35 0.050(4) 0.089(4) 0.042(4) 0.022(3) 0.029(3) 0.011(3) C36 0.040(3) 0.068(4) 0.051(4) 0.020(3) 0.017(3) -0.005(3) C37 0.041(3) 0.055(3) 0.029(3) 0.007(2) 0.012(2) -0.003(2) C38 0.035(3) 0.045(3) 0.012(2) -0.002(2) 0.008(2) -0.009(2) C39 0.046(3) 0.052(3) 0.015(3) 0.001(2) 0.010(2) -0.006(3) C310 0.063(4) 0.051(3) 0.028(3) -0.002(2) 0.019(3) -0.014(3) C311 0.052(4) 0.070(4) 0.032(3) -0.009(3) 0.019(3) -0.024(3) C312 0.036(3) 0.075(4) 0.037(3) -0.013(3) 0.008(2) -0.004(3) C313 0.044(3) 0.053(3) 0.032(3) -0.006(2) 0.011(2) -0.003(3) C314 0.033(2) 0.044(3) 0.020(3) 0.002(2) 0.008(2) -0.005(2) C315 0.048(3) 0.052(3) 0.025(3) 0.006(2) 0.012(2) 0.002(2) C316 0.054(3) 0.057(4) 0.041(3) 0.014(3) 0.014(3) 0.003(3) C317 0.048(3) 0.048(3) 0.058(4) 0.002(3) 0.019(3) 0.001(2) C318 0.061(3) 0.054(4) 0.048(4) -0.001(3) 0.027(3) 0.002(3) C319 0.048(3) 0.048(3) 0.032(3) 0.001(2) 0.018(2) -0.003(2) N4 0.038(2) 0.039(2) 0.025(2) 0.0010(17) 0.0139(17) -0.0023(17) C41 0.040(3) 0.037(3) 0.026(3) 0.004(2) 0.013(2) -0.006(2) C42 0.039(3) 0.039(3) 0.025(3) -0.001(2) 0.009(2) 0.001(2) C43 0.058(3) 0.044(3) 0.054(4) 0.012(3) 0.029(3) 0.007(3) C44 0.058(3) 0.059(4) 0.059(4) 0.003(3) 0.029(3) 0.010(3) C45 0.057(4) 0.056(4) 0.057(4) -0.002(3) 0.007(3) 0.017(3) C46 0.084(4) 0.052(4) 0.041(4) 0.008(3) 0.017(3) 0.013(3) C47 0.063(3) 0.047(3) 0.032(3) 0.006(2) 0.022(3) 0.007(3) C48 0.040(3) 0.043(3) 0.024(3) 0.001(2) 0.018(2) -0.007(2) C49 0.044(3) 0.052(3) 0.029(3) 0.004(2) 0.010(2) -0.003(3) C410 0.045(3) 0.076(4) 0.030(3) 0.017(3) 0.010(3) -0.006(3) C411 0.057(4) 0.082(4) 0.031(3) 0.003(3) 0.005(3) -0.022(3) C412 0.074(4) 0.066(4) 0.040(4) -0.014(3) 0.015(3) -0.016(3) C413 0.054(3) 0.047(3) 0.035(3) 0.000(3) 0.009(3) -0.003(2) C414 0.038(3) 0.043(3) 0.018(3) 0.007(2) 0.009(2) 0.004(2) C415 0.043(3) 0.066(3) 0.031(3) 0.003(2) 0.013(2) -0.007(3) C416 0.046(3) 0.103(5) 0.034(4) 0.006(3) 0.019(3) -0.019(3) C417 0.054(3) 0.098(4) 0.034(4) 0.007(3) 0.030(3) 0.005(3) C418 0.054(3) 0.074(4) 0.029(3) -0.003(3) 0.020(3) -0.008(3) C419 0.049(3) 0.057(3) 0.025(3) -0.001(2) 0.016(2) -0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.516(5) . ? N1 H1A 0.910 . ? N1 H1B 0.910 . ? N1 H1C 0.910 . ? C1 C2 1.530(6) . ? C1 C8 1.533(6) . ? C1 C14 1.544(6) . ? C2 C3 1.387(6) . ? C2 C7 1.395(6) . ? C3 C4 1.378(6) . ? C3 H3A 0.950 . ? C4 C5 1.368(7) . ? C4 H4A 0.950 . ? C5 C6 1.386(7) . ? C5 H5A 0.950 . ? C6 C7 1.370(6) . ? C6 H6A 0.950 . ? C7 H7A 0.950 . ? C8 C9 1.380(6) . ? C8 C13 1.391(6) . ? C9 C10 1.390(6) . ? C9 H9A 0.950 . ? C10 C11 1.363(6) . ? C10 H10A 0.950 . ? C11 C12 1.373(6) . ? C11 H11A 0.950 . ? C12 C13 1.389(6) . ? C12 H12A 0.950 . ? C13 H13A 0.950 . ? C14 C15 1.380(6) . ? C14 C19 1.386(6) . ? C15 C16 1.391(6) . ? C15 H15A 0.950 . ? C16 C17 1.382(7) . ? C16 H16A 0.950 . ? C17 C18 1.368(7) . ? C17 H17A 0.950 . ? C18 C19 1.378(6) . ? C18 H18A 0.950 . ? C19 H19A 0.950 . ? N2 C21 1.532(5) . ? N2 H2A 0.910 . ? N2 H2B 0.910 . ? N2 H2C 0.910 . ? C21 C22 1.517(6) . ? C21 C28 1.533(6) . ? C21 C214 1.547(6) . ? C22 C23 1.386(6) . ? C22 C27 1.398(6) . ? C23 C24 1.390(7) . ? C23 H23A 0.950 . ? C24 C25 1.363(8) . ? C24 H24A 0.950 . ? C25 C26 1.375(7) . ? C25 H25A 0.9500 . ? C26 C27 1.371(6) . ? C26 H26A 0.950 . ? C27 H27A 0.950 . ? C28 C213 1.378(6) . ? C28 C29 1.390(6) . ? C29 C210 1.389(6) . ? C29 H29A 0.950 . ? C210 C211 1.373(7) . ? C210 H21A 0.950 . ? C211 C212 1.376(7) . ? C211 H21B 0.950 . ? C212 C213 1.382(7) . ? C212 H21C 0.950 . ? C213 H21D 0.950 . ? C214 C215 1.369(6) . ? C214 C219 1.393(6) . ? C215 C216 1.396(7) . ? C215 H21E 0.950 . ? C216 C217 1.362(7) . ? C216 H21F 0.950 . ? C217 C218 1.368(6) . ? C217 H21G 0.950 . ? C218 C219 1.393(6) . ? C218 H21H 0.950 . ? C219 H21I 0.950 . ? N3 C31 1.527(5) . ? N3 H3B 0.910 . ? N3 H3C 0.910 . ? N3 H3D 0.910 . ? C31 C314 1.532(6) . ? C31 C38 1.536(6) . ? C31 C32 1.543(6) . ? C32 C37 1.390(6) . ? C32 C33 1.393(6) . ? C33 C34 1.399(6) . ? C33 H33A 0.950 . ? C34 C35 1.378(7) . ? C34 H34A 0.950 . ? C35 C36 1.365(7) . ? C35 H35A 0.950 . ? C36 C37 1.390(6) . ? C36 H36A 0.950 . ? C37 H37A 0.950 . ? C38 C39 1.384(6) . ? C38 C313 1.387(6) . ? C39 C310 1.385(6) . ? C39 H39A 0.950 . ? C310 C311 1.395(7) . ? C310 H31A 0.950 . ? C311 C312 1.369(7) . ? C311 H31B 0.950 . ? C312 C313 1.392(6) . ? C312 H31C 0.950 . ? C313 H31D 0.950 . ? C314 C315 1.382(6) . ? C314 C319 1.394(6) . ? C315 C316 1.386(6) . ? C315 H31E 0.950 . ? C316 C317 1.369(7) . ? C316 H31F 0.950 . ? C317 C318 1.381(7) . ? C317 H31G 0.950 . ? C318 C319 1.375(6) . ? C318 H31H 0.950 . ? C319 H31I 0.950 . ? N4 C41 1.523(5) . ? N4 H4B 0.910 . ? N4 H4C 0.910 . ? N4 H4D 0.910 . ? C41 C42 1.527(6) . ? C41 C48 1.535(6) . ? C41 C414 1.541(6) . ? C42 C47 1.375(6) . ? C42 C43 1.397(6) . ? C43 C44 1.363(6) . ? C43 H43A 0.950 . ? C44 C45 1.387(7) . ? C44 H44A 0.950 . ? C45 C46 1.380(7) . ? C45 H45A 0.950 . ? C46 C47 1.378(6) . ? C46 H46A 0.950 . ? C47 H47A 0.950 . ? C48 C413 1.387(6) . ? C48 C49 1.394(6) . ? C49 C410 1.372(6) . ? C49 H49A 0.950 . ? C410 C411 1.379(7) . ? C410 H41A 0.950 . ? C411 C412 1.373(7) . ? C411 H41B 0.950 . ? C412 C413 1.395(7) . ? C412 H41C 0.950 . ? C413 H41D 0.950 . ? C414 C415 1.383(6) . ? C414 C419 1.392(6) . ? C415 C416 1.376(6) . ? C415 H41E 0.950 . ? C416 C417 1.361(7) . ? C416 H41F 0.950 . ? C417 C418 1.376(7) . ? C417 H41G 0.950 . ? C418 C419 1.387(6) . ? C418 H41H 0.950 . ? C419 H41I 0.950 . ? C1S C3S 1.3502(10) . ? C1S C1S 1.3504(10) 2 ? C1S H1SA 0.950 . ? C2S C2S 1.3489(10) 2 ? C2S C3S 1.3490(10) . ? C2S H2SA 0.950 . ? C3S H3S 0.950 . ? C4S H4SA 0.960 . ? C4S H4SB 0.960 . ? C4S H4SC 0.960 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? N1 C1 C2 108.0(3) . . ? N1 C1 C8 107.9(3) . . ? C2 C1 C8 111.1(3) . . ? N1 C1 C14 105.6(3) . . ? C2 C1 C14 111.7(3) . . ? C8 C1 C14 112.3(3) . . ? C3 C2 C7 117.3(4) . . ? C3 C2 C1 121.6(4) . . ? C7 C2 C1 121.1(4) . . ? C4 C3 C2 121.2(4) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C5 C4 C3 120.7(5) . . ? C5 C4 H4A 119.6 . . ? C3 C4 H4A 119.6 . . ? C4 C5 C6 119.2(5) . . ? C4 C5 H5A 120.4 . . ? C6 C5 H5A 120.4 . . ? C7 C6 C5 120.1(5) . . ? C7 C6 H6A 120.0 . . ? C5 C6 H6A 120.0 . . ? C6 C7 C2 121.5(4) . . ? C6 C7 H7A 119.2 . . ? C2 C7 H7A 119.2 . . ? C9 C8 C13 118.3(4) . . ? C9 C8 C1 121.4(4) . . ? C13 C8 C1 120.2(4) . . ? C8 C9 C10 120.6(4) . . ? C8 C9 H9A 119.7 . . ? C10 C9 H9A 119.7 . . ? C11 C10 C9 120.6(4) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C10 C11 C12 119.8(4) . . ? C10 C11 H11A 120.1 . . ? C12 C11 H11A 120.1 . . ? C11 C12 C13 120.0(5) . . ? C11 C12 H12A 120.0 . . ? C13 C12 H12A 120.0 . . ? C12 C13 C8 120.7(4) . . ? C12 C13 H13A 119.7 . . ? C8 C13 H13A 119.7 . . ? C15 C14 C19 118.4(4) . . ? C15 C14 C1 122.1(4) . . ? C19 C14 C1 119.6(4) . . ? C14 C15 C16 120.1(5) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? C17 C16 C15 120.9(5) . . ? C17 C16 H16A 119.6 . . ? C15 C16 H16A 119.6 . . ? C18 C17 C16 118.8(5) . . ? C18 C17 H17A 120.6 . . ? C16 C17 H17A 120.6 . . ? C17 C18 C19 120.7(5) . . ? C17 C18 H18A 119.7 . . ? C19 C18 H18A 119.7 . . ? C18 C19 C14 121.1(5) . . ? C18 C19 H19A 119.4 . . ? C14 C19 H19A 119.4 . . ? C21 N2 H2A 109.5 . . ? C21 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C21 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C22 C21 N2 108.0(3) . . ? C22 C21 C28 111.7(4) . . ? N2 C21 C28 108.8(3) . . ? C22 C21 C214 111.5(3) . . ? N2 C21 C214 105.9(3) . . ? C28 C21 C214 110.7(3) . . ? C23 C22 C27 117.5(4) . . ? C23 C22 C21 121.7(4) . . ? C27 C22 C21 120.7(4) . . ? C22 C23 C24 120.5(5) . . ? C22 C23 H23A 119.7 . . ? C24 C23 H23A 119.7 . . ? C25 C24 C23 120.8(5) . . ? C25 C24 H24A 119.6 . . ? C23 C24 H24A 119.6 . . ? C24 C25 C26 119.4(5) . . ? C24 C25 H25A 120.3 . . ? C26 C25 H25A 120.3 . . ? C27 C26 C25 120.4(5) . . ? C27 C26 H26A 119.8 . . ? C25 C26 H26A 119.8 . . ? C26 C27 C22 121.3(5) . . ? C26 C27 H27A 119.3 . . ? C22 C27 H27A 119.3 . . ? C213 C28 C29 118.5(4) . . ? C213 C28 C21 120.9(4) . . ? C29 C28 C21 120.4(4) . . ? C210 C29 C28 120.3(5) . . ? C210 C29 H29A 119.8 . . ? C28 C29 H29A 119.8 . . ? C211 C210 C29 120.5(5) . . ? C211 C210 H21A 119.8 . . ? C29 C210 H21A 119.8 . . ? C210 C211 C212 119.3(5) . . ? C210 C211 H21B 120.4 . . ? C212 C211 H21B 120.4 . . ? C211 C212 C213 120.5(5) . . ? C211 C212 H21C 119.8 . . ? C213 C212 H21C 119.8 . . ? C28 C213 C212 120.9(5) . . ? C28 C213 H21D 119.5 . . ? C212 C213 H21D 119.5 . . ? C215 C214 C219 118.8(4) . . ? C215 C214 C21 122.6(4) . . ? C219 C214 C21 118.5(4) . . ? C214 C215 C216 120.7(5) . . ? C214 C215 H21E 119.6 . . ? C216 C215 H21E 119.6 . . ? C217 C216 C215 119.8(5) . . ? C217 C216 H21F 120.1 . . ? C215 C216 H21F 120.1 . . ? C216 C217 C218 120.8(5) . . ? C216 C217 H21G 119.6 . . ? C218 C217 H21G 119.6 . . ? C217 C218 C219 119.5(5) . . ? C217 C218 H21H 120.3 . . ? C219 C218 H21H 120.3 . . ? C214 C219 C218 120.4(4) . . ? C214 C219 H21I 119.8 . . ? C218 C219 H21I 119.8 . . ? C31 N3 H3B 109.5 . . ? C31 N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? C31 N3 H3D 109.5 . . ? H3B N3 H3D 109.5 . . ? H3C N3 H3D 109.5 . . ? N3 C31 C314 109.2(3) . . ? N3 C31 C38 105.6(3) . . ? C314 C31 C38 111.7(3) . . ? N3 C31 C32 106.7(3) . . ? C314 C31 C32 109.6(3) . . ? C38 C31 C32 113.7(3) . . ? C37 C32 C33 119.1(4) . . ? C37 C32 C31 119.1(4) . . ? C33 C32 C31 121.5(4) . . ? C32 C33 C34 119.7(5) . . ? C32 C33 H33A 120.1 . . ? C34 C33 H33A 120.1 . . ? C35 C34 C33 120.5(5) . . ? C35 C34 H34A 119.8 . . ? C33 C34 H34A 119.8 . . ? C36 C35 C34 119.7(5) . . ? C36 C35 H35A 120.1 . . ? C34 C35 H35A 120.1 . . ? C35 C36 C37 120.9(5) . . ? C35 C36 H36A 119.5 . . ? C37 C36 H36A 119.5 . . ? C36 C37 C32 120.1(5) . . ? C36 C37 H37A 119.9 . . ? C32 C37 H37A 119.9 . . ? C39 C38 C313 118.4(4) . . ? C39 C38 C31 120.2(4) . . ? C313 C38 C31 121.5(4) . . ? C38 C39 C310 121.2(4) . . ? C38 C39 H39A 119.4 . . ? C310 C39 H39A 119.4 . . ? C39 C310 C311 120.0(5) . . ? C39 C310 H31A 120.0 . . ? C311 C310 H31A 120.0 . . ? C312 C311 C310 119.1(5) . . ? C312 C311 H31B 120.4 . . ? C310 C311 H31B 120.4 . . ? C311 C312 C313 120.7(5) . . ? C311 C312 H31C 119.6 . . ? C313 C312 H31C 119.6 . . ? C38 C313 C312 120.6(5) . . ? C38 C313 H31D 119.7 . . ? C312 C313 H31D 119.7 . . ? C315 C314 C319 118.0(4) . . ? C315 C314 C31 120.1(4) . . ? C319 C314 C31 121.7(4) . . ? C314 C315 C316 120.8(4) . . ? C314 C315 H31E 119.6 . . ? C316 C315 H31E 119.6 . . ? C317 C316 C315 120.4(5) . . ? C317 C316 H31F 119.8 . . ? C315 C316 H31F 119.8 . . ? C316 C317 C318 119.6(5) . . ? C316 C317 H31G 120.2 . . ? C318 C317 H31G 120.2 . . ? C319 C318 C317 120.1(5) . . ? C319 C318 H31H 119.9 . . ? C317 C318 H31H 119.9 . . ? C318 C319 C314 121.1(4) . . ? C318 C319 H31I 119.5 . . ? C314 C319 H31I 119.5 . . ? C41 N4 H4B 109.5 . . ? C41 N4 H4C 109.5 . . ? H4B N4 H4C 109.5 . . ? C41 N4 H4D 109.5 . . ? H4B N4 H4D 109.5 . . ? H4C N4 H4D 109.5 . . ? N4 C41 C42 107.4(3) . . ? N4 C41 C48 106.6(3) . . ? C42 C41 C48 112.4(4) . . ? N4 C41 C414 107.7(3) . . ? C42 C41 C414 110.6(3) . . ? C48 C41 C414 111.9(3) . . ? C47 C42 C43 117.6(4) . . ? C47 C42 C41 122.4(4) . . ? C43 C42 C41 120.0(4) . . ? C44 C43 C42 121.0(5) . . ? C44 C43 H43A 119.5 . . ? C42 C43 H43A 119.5 . . ? C43 C44 C45 120.7(5) . . ? C43 C44 H44A 119.6 . . ? C45 C44 H44A 119.6 . . ? C46 C45 C44 119.0(5) . . ? C46 C45 H45A 120.5 . . ? C44 C45 H45A 120.5 . . ? C47 C46 C45 119.7(5) . . ? C47 C46 H46A 120.2 . . ? C45 C46 H46A 120.2 . . ? C42 C47 C46 122.0(5) . . ? C42 C47 H47A 119.0 . . ? C46 C47 H47A 119.0 . . ? C413 C48 C49 118.0(4) . . ? C413 C48 C41 121.6(4) . . ? C49 C48 C41 120.3(4) . . ? C410 C49 C48 121.3(5) . . ? C410 C49 H49A 119.3 . . ? C48 C49 H49A 119.3 . . ? C49 C410 C411 120.7(5) . . ? C49 C410 H41A 119.7 . . ? C411 C410 H41A 119.7 . . ? C412 C411 C410 118.7(5) . . ? C412 C411 H41B 120.7 . . ? C410 C411 H41B 120.7 . . ? C411 C412 C413 121.3(5) . . ? C411 C412 H41C 119.3 . . ? C413 C412 H41C 119.3 . . ? C48 C413 C412 119.9(5) . . ? C48 C413 H41D 120.0 . . ? C412 C413 H41D 120.0 . . ? C415 C414 C419 118.1(4) . . ? C415 C414 C41 121.5(4) . . ? C419 C414 C41 120.0(4) . . ? C416 C415 C414 121.4(5) . . ? C416 C415 H41E 119.3 . . ? C414 C415 H41E 119.3 . . ? C417 C416 C415 119.8(5) . . ? C417 C416 H41F 120.1 . . ? C415 C416 H41F 120.1 . . ? C416 C417 C418 120.6(5) . . ? C416 C417 H41G 119.7 . . ? C418 C417 H41G 119.7 . . ? C417 C418 C419 119.8(5) . . ? C417 C418 H41H 120.1 . . ? C419 C418 H41H 120.1 . . ? C418 C419 C414 120.3(4) . . ? C418 C419 H41I 119.9 . . ? C414 C419 H41I 119.9 . . ? C3S C1S C1S 118.54(10) . 2 ? C3S C1S H1SA 120.7 . . ? C1S C1S H1SA 120.7 2 . ? C2S C2S C3S 118.61(10) 2 . ? C2S C2S H2SA 120.7 2 . ? C3S C2S H2SA 120.7 . . ? C2S C3S C1S 122.8(2) . . ? C2S C3S H3S 118.6 . . ? C1S C3S H3S 118.6 . . ? H4SA C4S H4SB 109.5 . . ? H4SA C4S H4SC 109.5 . . ? H4SB C4S H4SC 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 N1 C1 C2 C3 -140.4(4) . . . . ? C8 C1 C2 C3 -22.3(5) . . . . ? C14 C1 C2 C3 104.0(5) . . . . ? N1 C1 C2 C7 42.8(5) . . . . ? C8 C1 C2 C7 160.9(4) . . . . ? C14 C1 C2 C7 -72.9(5) . . . . ? C7 C2 C3 C4 1.6(7) . . . . ? C1 C2 C3 C4 -175.4(4) . . . . ? C2 C3 C4 C5 -1.4(8) . . . . ? C3 C4 C5 C6 1.1(8) . . . . ? C4 C5 C6 C7 -1.0(7) . . . . ? C5 C6 C7 C2 1.2(7) . . . . ? C3 C2 C7 C6 -1.5(7) . . . . ? C1 C2 C7 C6 175.5(4) . . . . ? N1 C1 C8 C9 -138.2(4) . . . . ? C2 C1 C8 C9 103.7(4) . . . . ? C14 C1 C8 C9 -22.2(6) . . . . ? N1 C1 C8 C13 45.6(5) . . . . ? C2 C1 C8 C13 -72.6(5) . . . . ? C14 C1 C8 C13 161.5(4) . . . . ? C13 C8 C9 C10 0.8(7) . . . . ? C1 C8 C9 C10 -175.5(4) . . . . ? C8 C9 C10 C11 -0.6(7) . . . . ? C9 C10 C11 C12 -0.2(7) . . . . ? C10 C11 C12 C13 0.8(7) . . . . ? C11 C12 C13 C8 -0.6(7) . . . . ? C9 C8 C13 C12 -0.2(7) . . . . ? C1 C8 C13 C12 176.1(4) . . . . ? N1 C1 C14 C15 -134.9(4) . . . . ? C2 C1 C14 C15 -17.8(5) . . . . ? C8 C1 C14 C15 107.8(4) . . . . ? N1 C1 C14 C19 45.9(5) . . . . ? C2 C1 C14 C19 163.0(4) . . . . ? C8 C1 C14 C19 -71.4(5) . . . . ? C19 C14 C15 C16 -1.4(6) . . . . ? C1 C14 C15 C16 179.4(4) . . . . ? C14 C15 C16 C17 0.6(7) . . . . ? C15 C16 C17 C18 0.3(7) . . . . ? C16 C17 C18 C19 -0.4(7) . . . . ? C17 C18 C19 C14 -0.5(7) . . . . ? C15 C14 C19 C18 1.4(7) . . . . ? C1 C14 C19 C18 -179.4(4) . . . . ? N2 C21 C22 C23 -136.6(4) . . . . ? C28 C21 C22 C23 103.8(5) . . . . ? C214 C21 C22 C23 -20.6(6) . . . . ? N2 C21 C22 C27 48.4(5) . . . . ? C28 C21 C22 C27 -71.2(5) . . . . ? C214 C21 C22 C27 164.4(4) . . . . ? C27 C22 C23 C24 -1.3(7) . . . . ? C21 C22 C23 C24 -176.5(4) . . . . ? C22 C23 C24 C25 2.8(8) . . . . ? C23 C24 C25 C26 -2.3(8) . . . . ? C24 C25 C26 C27 0.4(8) . . . . ? C25 C26 C27 C22 1.0(7) . . . . ? C23 C22 C27 C26 -0.5(7) . . . . ? C21 C22 C27 C26 174.7(4) . . . . ? C22 C21 C28 C213 165.5(4) . . . . ? N2 C21 C28 C213 46.4(5) . . . . ? C214 C21 C28 C213 -69.6(5) . . . . ? C22 C21 C28 C29 -20.9(5) . . . . ? N2 C21 C28 C29 -139.9(4) . . . . ? C214 C21 C28 C29 104.0(5) . . . . ? C213 C28 C29 C210 2.2(7) . . . . ? C21 C28 C29 C210 -171.6(4) . . . . ? C28 C29 C210 C211 -0.6(7) . . . . ? C29 C210 C211 C212 -1.4(7) . . . . ? C210 C211 C212 C213 1.7(8) . . . . ? C29 C28 C213 C212 -1.9(7) . . . . ? C21 C28 C213 C212 171.8(4) . . . . ? C211 C212 C213 C28 0.0(7) . . . . ? C22 C21 C214 C215 110.3(5) . . . . ? N2 C21 C214 C215 -132.5(4) . . . . ? C28 C21 C214 C215 -14.7(6) . . . . ? C22 C21 C214 C219 -65.9(5) . . . . ? N2 C21 C214 C219 51.3(5) . . . . ? C28 C21 C214 C219 169.1(4) . . . . ? C219 C214 C215 C216 -1.1(7) . . . . ? C21 C214 C215 C216 -177.3(4) . . . . ? C214 C215 C216 C217 0.2(8) . . . . ? C215 C216 C217 C218 0.8(8) . . . . ? C216 C217 C218 C219 -0.9(8) . . . . ? C215 C214 C219 C218 1.0(7) . . . . ? C21 C214 C219 C218 177.3(4) . . . . ? C217 C218 C219 C214 0.0(7) . . . . ? N3 C31 C32 C37 53.2(5) . . . . ? C314 C31 C32 C37 -65.0(5) . . . . ? C38 C31 C32 C37 169.2(4) . . . . ? N3 C31 C32 C33 -133.2(4) . . . . ? C314 C31 C32 C33 108.6(4) . . . . ? C38 C31 C32 C33 -17.2(6) . . . . ? C37 C32 C33 C34 -0.3(6) . . . . ? C31 C32 C33 C34 -173.9(4) . . . . ? C32 C33 C34 C35 0.3(7) . . . . ? C33 C34 C35 C36 -0.6(8) . . . . ? C34 C35 C36 C37 0.8(8) . . . . ? C35 C36 C37 C32 -0.7(7) . . . . ? C33 C32 C37 C36 0.5(6) . . . . ? C31 C32 C37 C36 174.2(4) . . . . ? N3 C31 C38 C39 55.5(5) . . . . ? C314 C31 C38 C39 174.2(4) . . . . ? C32 C31 C38 C39 -61.1(5) . . . . ? N3 C31 C38 C313 -122.8(4) . . . . ? C314 C31 C38 C313 -4.1(5) . . . . ? C32 C31 C38 C313 120.6(4) . . . . ? C313 C38 C39 C310 1.0(6) . . . . ? C31 C38 C39 C310 -177.3(4) . . . . ? C38 C39 C310 C311 0.1(6) . . . . ? C39 C310 C311 C312 -1.1(7) . . . . ? C310 C311 C312 C313 0.9(7) . . . . ? C39 C38 C313 C312 -1.2(6) . . . . ? C31 C38 C313 C312 177.1(4) . . . . ? C311 C312 C313 C38 0.2(7) . . . . ? N3 C31 C314 C315 -148.0(4) . . . . ? C38 C31 C314 C315 95.6(4) . . . . ? C32 C31 C314 C315 -31.4(5) . . . . ? N3 C31 C314 C319 37.5(5) . . . . ? C38 C31 C314 C319 -78.9(5) . . . . ? C32 C31 C314 C319 154.1(4) . . . . ? C319 C314 C315 C316 -0.7(6) . . . . ? C31 C314 C315 C316 -175.4(4) . . . . ? C314 C315 C316 C317 0.8(7) . . . . ? C315 C316 C317 C318 -0.7(7) . . . . ? C316 C317 C318 C319 0.5(7) . . . . ? C317 C318 C319 C314 -0.4(7) . . . . ? C315 C314 C319 C318 0.5(6) . . . . ? C31 C314 C319 C318 175.1(4) . . . . ? N4 C41 C42 C47 -134.7(4) . . . . ? C48 C41 C42 C47 108.4(5) . . . . ? C414 C41 C42 C47 -17.5(6) . . . . ? N4 C41 C42 C43 49.2(5) . . . . ? C48 C41 C42 C43 -67.7(5) . . . . ? C414 C41 C42 C43 166.4(4) . . . . ? C47 C42 C43 C44 -0.2(7) . . . . ? C41 C42 C43 C44 176.1(4) . . . . ? C42 C43 C44 C45 0.3(8) . . . . ? C43 C44 C45 C46 0.0(8) . . . . ? C44 C45 C46 C47 -0.5(8) . . . . ? C43 C42 C47 C46 -0.3(7) . . . . ? C41 C42 C47 C46 -176.5(4) . . . . ? C45 C46 C47 C42 0.6(8) . . . . ? N4 C41 C48 C413 -130.0(4) . . . . ? C42 C41 C48 C413 -12.6(6) . . . . ? C414 C41 C48 C413 112.5(4) . . . . ? N4 C41 C48 C49 52.2(5) . . . . ? C42 C41 C48 C49 169.5(4) . . . . ? C414 C41 C48 C49 -65.3(5) . . . . ? C413 C48 C49 C410 1.9(6) . . . . ? C41 C48 C49 C410 179.9(4) . . . . ? C48 C49 C410 C411 -1.9(7) . . . . ? C49 C410 C411 C412 1.0(7) . . . . ? C410 C411 C412 C413 -0.2(8) . . . . ? C49 C48 C413 C412 -1.1(7) . . . . ? C41 C48 C413 C412 -179.0(4) . . . . ? C411 C412 C413 C48 0.2(8) . . . . ? N4 C41 C414 C415 -143.9(4) . . . . ? C42 C41 C414 C415 99.1(5) . . . . ? C48 C41 C414 C415 -27.0(6) . . . . ? N4 C41 C414 C419 43.4(5) . . . . ? C42 C41 C414 C419 -73.6(5) . . . . ? C48 C41 C414 C419 160.3(4) . . . . ? C419 C414 C415 C416 1.2(7) . . . . ? C41 C414 C415 C416 -171.6(4) . . . . ? C414 C415 C416 C417 -1.1(8) . . . . ? C415 C416 C417 C418 0.2(8) . . . . ? C416 C417 C418 C419 0.6(8) . . . . ? C417 C418 C419 C414 -0.4(7) . . . . ? C415 C414 C419 C418 -0.5(7) . . . . ? C41 C414 C419 C418 172.5(4) . . . . ? C2S C2S C3S C1S 0.0(14) 2 . . . ? C1S C1S C3S C2S -1.2(11) 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 N1 H1A Cl1 0.91 2.26 3.116(3) 156.6 . N1 H1B Cl2 0.91 2.25 3.126(3) 162.6 . N1 H1C Cl3 0.91 2.28 3.163(3) 162.3 . N2 H2B Cl2 0.91 2.33 3.180(4) 155.4 . N2 H2A Cl3 0.91 2.39 3.184(3) 146.1 . N2 H2C Cl4 0.91 2.28 3.156(3) 162.7 . N3 H3B Cl1 0.91 2.32 3.186(3) 159.1 . N3 H3D Cl2 0.91 2.38 3.181(3) 147.5 . N3 H3C Cl4 0.91 2.27 3.147(4) 162.7 . N4 H4D Cl1 0.91 2.35 3.190(4) 153.4 . N4 H4B Cl3 0.91 2.28 3.150(3) 161.1 . N4 H4C Cl4 0.91 2.27 3.124(3) 155.8 . #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 645314' _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 N +, Br -, 0.25(C H Cl3)' _chemical_formula_sum 'C19.25 H18.25 Br Cl0.75 N' _chemical_formula_weight 370.10 _chemical_absolute_configuration ad 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M 'P 3' _symmetry_space_group_name_Hall 'P 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' _cell_length_a 14.3387(3) _cell_length_b 14.3387(3) _cell_length_c 20.4479(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3640.82(18) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7442 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 25.39 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1508 _exptl_absorpt_coefficient_mu 2.364 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.618 _exptl_absorpt_correction_T_max 0.798 _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.775824 ; _exptl_special_details ; PLATON identifies voids of ca 250 \%A^3^ between the cubanes. It is probable that further CHCl~3~ molecules reside in these voids. However, nothing further can be resolved in this region. Application of SQUEEZE gives only a very moderate improvement in R values and does not affect the residual electron density associated with the CHCl~3~ molecules that are present. This CIF refers to standard (non-SQUEEZED) data. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay ? _diffrn_reflns_number 58037 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 26.40 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 9521 _reflns_number_gt 8176 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-22 (Bruker Nonius, 2004)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10' _computing_molecular_graphics 'SHELXTL v.6.10' _computing_publication_material 'SHELXTL v.6.10' _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^)+(0.0967P)^2^+13.2783P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack (1983), 4565 Friedel pairs' _refine_ls_abs_structure_Flack 0.081(15) _refine_ls_number_reflns 9521 _refine_ls_number_parameters 529 _refine_ls_number_restraints 331 # ISOR restraints placed on ADPs of all C atoms _refine_ls_R_factor_all 0.0734 _refine_ls_R_factor_gt 0.0630 _refine_ls_wR_factor_ref 0.1833 _refine_ls_wR_factor_gt 0.1778 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.805 _refine_diff_density_min -0.686 _refine_diff_density_rms 0.116 # difference peak associated with CHCl~3~ molecule 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 Br1 Br 0.0000 0.0000 0.96958(6) 0.0351(3) Uani 1 3 d S . . Br2 Br 0.00737(8) 0.19714(7) 0.77444(4) 0.0512(3) Uani 1 1 d . . . Br3 Br 0.3333 0.6667 0.18148(6) 0.0320(3) Uani 1 3 d S . . Br4 Br 0.15967(6) 0.69986(6) 0.37209(4) 0.03731(19) Uani 1 1 d . . . N1 N 0.0000 0.0000 0.6816(5) 0.033(2) Uani 1 3 d S . . H1A H 0.0006 0.0601 0.6964 0.049 Uiso 1 1 d R . . C11 C 0.0000 0.0000 0.6076(6) 0.033(3) Uani 1 3 d SU . . C12 C 0.1005(7) 0.1013(7) 0.5847(4) 0.0391(18) Uani 1 1 d U . . C13 C 0.0981(8) 0.1621(8) 0.5307(5) 0.053(2) Uani 1 1 d U . . H13 H 0.0312 0.1424 0.5105 0.064 Uiso 1 1 calc R . . C14 C 0.1883(9) 0.2466(10) 0.5076(6) 0.067(3) Uani 1 1 d U . . H14A H 0.1831 0.2846 0.4710 0.081 Uiso 1 1 calc R . . C15 C 0.2899(9) 0.2812(8) 0.5352(5) 0.060(3) Uani 1 1 d U . . H15A H 0.3533 0.3414 0.5186 0.072 Uiso 1 1 calc R . . C16 C 0.2923(8) 0.2227(9) 0.5879(5) 0.061(3) Uani 1 1 d U . . H16A H 0.3593 0.2434 0.6084 0.073 Uiso 1 1 calc R . . C17 C 0.2014(7) 0.1359(8) 0.6115(5) 0.050(2) Uani 1 1 d U . . H17A H 0.2075 0.0976 0.6476 0.060 Uiso 1 1 calc R . . N2 N 0.1874(5) 0.1816(5) 0.8676(4) 0.0445(16) Uani 1 1 d . . . H2A H 0.1521 0.1363 0.9014 0.067 Uiso 1 1 calc R . . H2B H 0.1987 0.1446 0.8353 0.067 Uiso 1 1 calc R . . H2C H 0.1469 0.2092 0.8517 0.067 Uiso 1 1 calc R . . C21 C 0.2948(6) 0.2727(7) 0.8914(4) 0.0443(19) Uani 1 1 d U . . C22 C 0.3524(8) 0.3482(9) 0.8330(5) 0.059(2) Uani 1 1 d U . . C23 C 0.4386(8) 0.4396(8) 0.8419(5) 0.063(3) Uani 1 1 d U . . H23A H 0.4600 0.4620 0.8857 0.075 Uiso 1 1 calc R . . C24 C 0.5035(12) 0.5090(11) 0.7917(7) 0.090(4) Uani 1 1 d U . . H24A H 0.5717 0.5697 0.8015 0.108 Uiso 1 1 calc R . . C25 C 0.4678(12) 0.4880(11) 0.7299(7) 0.085(4) Uani 1 1 d U . . H25A H 0.5064 0.5371 0.6957 0.102 Uiso 1 1 calc R . . C26 C 0.3741(12) 0.3936(11) 0.7174(7) 0.087(4) Uani 1 1 d U . . H26A H 0.3487 0.3765 0.6737 0.104 Uiso 1 1 calc R . . C27 C 0.3136(10) 0.3201(11) 0.7690(6) 0.073(3) Uani 1 1 d U . . H27A H 0.2493 0.2545 0.7600 0.088 Uiso 1 1 calc R . . C28 C 0.3473(8) 0.2157(7) 0.9208(4) 0.052(2) Uani 1 1 d U . . C29 C 0.4395(10) 0.2272(10) 0.8912(7) 0.079(3) Uani 1 1 d U . . H29A H 0.4659 0.2660 0.8515 0.095 Uiso 1 1 calc R . . C210 C 0.4933(12) 0.1781(12) 0.9232(9) 0.096(4) Uani 1 1 d U . . H21A H 0.5602 0.1901 0.9064 0.115 Uiso 1 1 calc R . . C211 C 0.4492(11) 0.1125(11) 0.9791(7) 0.083(4) Uani 1 1 d U . . H21B H 0.4851 0.0790 0.9986 0.100 Uiso 1 1 calc R . . C212 C 0.3547(9) 0.0974(9) 1.0048(6) 0.067(3) Uani 1 1 d U . . H21C H 0.3213 0.0504 1.0408 0.081 Uiso 1 1 calc R . . C213 C 0.3097(7) 0.1534(8) 0.9765(5) 0.055(2) Uani 1 1 d U . . H21D H 0.2480 0.1485 0.9970 0.066 Uiso 1 1 calc R . . C214 C 0.2757(7) 0.3413(6) 0.9400(4) 0.0439(19) Uani 1 1 d U . . C215 C 0.1938(8) 0.3652(7) 0.9299(5) 0.052(2) Uani 1 1 d U . . H21E H 0.1432 0.3294 0.8959 0.063 Uiso 1 1 calc R . . C216 C 0.1837(8) 0.4429(9) 0.9699(5) 0.064(3) Uani 1 1 d U . . H21F H 0.1280 0.4595 0.9630 0.077 Uiso 1 1 calc R . . C217 C 0.2607(8) 0.4921(8) 1.0191(5) 0.057(2) Uani 1 1 d U . . H21H H 0.2587 0.5449 1.0462 0.068 Uiso 1 1 calc R . . C218 C 0.3368(8) 0.4663(7) 1.0288(4) 0.054(2) Uani 1 1 d U . . H21I H 0.3885 0.5027 1.0622 0.065 Uiso 1 1 calc R . . C219 C 0.3440(7) 0.3873(6) 0.9917(4) 0.0407(17) Uani 1 1 d U . . H21G H 0.3955 0.3664 1.0024 0.049 Uiso 1 1 calc R . . N3 N 0.5043(5) 0.6357(5) 0.2783(4) 0.0337(13) Uani 1 1 d . . . H3A H 0.5363 0.6959 0.3037 0.050 Uiso 1 1 calc R . . H3B H 0.4523 0.5802 0.3018 0.050 Uiso 1 1 calc R . . H3C H 0.4741 0.6482 0.2427 0.050 Uiso 1 1 calc R . . C31 C 0.5866(5) 0.6076(5) 0.2566(4) 0.0309(15) Uani 1 1 d DU . . C32 C 0.6487(4) 0.5972(6) 0.3140(4) 0.0409(17) Uani 1 1 d DU . . C33 C 0.6726(8) 0.5129(10) 0.3149(7) 0.088(4) Uani 1 1 d DU . . H33A H 0.6513 0.4609 0.2809 0.105 Uiso 1 1 calc R . . C34 C 0.7275(10) 0.5121(13) 0.3673(8) 0.120(6) Uani 1 1 d DU . . H34A H 0.7458 0.4570 0.3697 0.144 Uiso 1 1 calc R . . C35 C 0.7598(8) 0.5838(12) 0.4178(6) 0.106(5) Uani 1 1 d DU . . H35A H 0.7979 0.5767 0.4537 0.128 Uiso 1 1 calc R . . C36 C 0.7393(7) 0.6579(8) 0.4168(5) 0.062(3) Uani 1 1 d DU . . H36A H 0.7627 0.7085 0.4517 0.075 Uiso 1 1 calc R . . C37 C 0.6829(7) 0.6671(8) 0.3655(4) 0.059(2) Uani 1 1 d DU . . H37A H 0.6671 0.7241 0.3658 0.071 Uiso 1 1 calc R . . C38 C 0.5338(6) 0.5081(6) 0.2128(4) 0.0348(17) Uani 1 1 d U . . C39 C 0.5840(8) 0.4907(8) 0.1598(6) 0.065(3) Uani 1 1 d U . . H39A H 0.6525 0.5471 0.1460 0.077 Uiso 1 1 calc R . . C310 C 0.5385(10) 0.3964(9) 0.1277(6) 0.070(3) Uani 1 1 d U . . H31A H 0.5788 0.3857 0.0947 0.085 Uiso 1 1 calc R . . C311 C 0.4371(9) 0.3161(7) 0.1406(5) 0.056(2) Uani 1 1 d U . . H31B H 0.4061 0.2488 0.1185 0.067 Uiso 1 1 calc R . . C312 C 0.3812(8) 0.3377(8) 0.1879(6) 0.064(3) Uani 1 1 d U . . H31C H 0.3071 0.2878 0.1951 0.077 Uiso 1 1 calc R . . C313 C 0.4316(7) 0.4302(8) 0.2244(5) 0.058(2) Uani 1 1 d U . . H31D H 0.3930 0.4397 0.2590 0.070 Uiso 1 1 calc R . . C314 C 0.6731(6) 0.7039(6) 0.2141(4) 0.0330(16) Uani 1 1 d U . . C315 C 0.6435(7) 0.7562(7) 0.1684(4) 0.047(2) Uani 1 1 d U . . H31E H 0.5699 0.7368 0.1644 0.057 Uiso 1 1 calc R . . C316 C 0.7173(8) 0.8336(9) 0.1298(5) 0.061(2) Uani 1 1 d U . . H31F H 0.6942 0.8684 0.0997 0.073 Uiso 1 1 calc R . . C317 C 0.8236(7) 0.8646(6) 0.1320(4) 0.0424(19) Uani 1 1 d U . . H31G H 0.8740 0.9182 0.1033 0.051 Uiso 1 1 calc R . . C318 C 0.8558(6) 0.8142(7) 0.1782(4) 0.0449(19) Uani 1 1 d U . . H31H H 0.9294 0.8338 0.1816 0.054 Uiso 1 1 calc R . . C319 C 0.7806(6) 0.7365(7) 0.2185(4) 0.0420(18) Uani 1 1 d U . . H31I H 0.8037 0.7044 0.2505 0.050 Uiso 1 1 calc R . . N4 N 0.3333 0.6667 0.4625(6) 0.036(3) Uani 1 3 d S . . H4A H 0.2718 0.6631 0.4477 0.054 Uiso 1 1 d R . . C41 C 0.3333 0.6667 0.5353(7) 0.040(3) Uani 1 3 d SU . . C42 C 0.2334(7) 0.5621(7) 0.5582(4) 0.0423(19) Uani 1 1 d U . . C43 C 0.2390(9) 0.4999(9) 0.6064(5) 0.063(3) Uani 1 1 d U . . H43A H 0.3068 0.5182 0.6251 0.075 Uiso 1 1 calc R . . C44 C 0.1448(10) 0.4084(9) 0.6289(6) 0.074(3) Uani 1 1 d U . . H44A H 0.1476 0.3659 0.6637 0.089 Uiso 1 1 calc R . . C45 C 0.0524(11) 0.3832(11) 0.6004(7) 0.081(4) Uani 1 1 d U . . H45A H -0.0105 0.3221 0.6167 0.097 Uiso 1 1 calc R . . C46 C 0.0391(10) 0.4387(10) 0.5481(6) 0.076(3) Uani 1 1 d U . . H46A H -0.0285 0.4166 0.5279 0.092 Uiso 1 1 calc R . . C47 C 0.1355(9) 0.5304(9) 0.5285(6) 0.065(3) Uani 1 1 d U . . H47A H 0.1331 0.5724 0.4933 0.078 Uiso 1 1 calc R . . Cl1 Cl 0.0172(3) 0.8922(3) 0.3382(2) 0.1007(11) Uani 1 1 d D . . Cl2 Cl 0.2713(5) 0.7395(6) 0.7776(3) 0.162(2) Uani 1 1 d D . . C100 C 0.0000 1.0000 0.3099(11) 0.101(7) Uani 1 3 d SDU . . H10A H 0.0000 1.0000 0.2610 0.121 Uiso 1 3 d SR . . C101 C 0.3333 0.6667 0.8112(14) 0.229(12) Uani 1 3 d SDU . . H10B H 0.3333 0.6667 0.8601 0.275 Uiso 1 3 calc SR . . 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 Br1 0.0391(4) 0.0391(4) 0.0271(6) 0.000 0.000 0.0196(2) Br2 0.0716(6) 0.0490(5) 0.0309(4) 0.0018(4) 0.0030(4) 0.0286(5) Br3 0.0319(4) 0.0319(4) 0.0323(7) 0.000 0.000 0.0159(2) Br4 0.0426(4) 0.0363(4) 0.0329(4) -0.0040(3) 0.0020(3) 0.0196(4) N1 0.040(4) 0.040(4) 0.019(5) 0.000 0.000 0.0198(18) C11 0.037(4) 0.037(4) 0.025(5) 0.000 0.000 0.0183(18) C12 0.045(4) 0.046(4) 0.027(3) -0.003(3) 0.008(3) 0.023(4) C13 0.059(5) 0.055(5) 0.041(4) 0.017(4) 0.013(4) 0.025(4) C14 0.063(6) 0.076(6) 0.059(5) 0.022(5) 0.020(4) 0.033(5) C15 0.072(6) 0.044(4) 0.048(5) 0.015(4) 0.021(4) 0.017(4) C16 0.040(4) 0.073(6) 0.064(6) 0.006(5) -0.001(4) 0.023(4) C17 0.043(4) 0.057(5) 0.044(4) 0.004(4) -0.002(4) 0.021(4) N2 0.044(4) 0.041(4) 0.033(4) -0.002(3) -0.005(3) 0.009(3) C21 0.037(4) 0.047(4) 0.032(4) -0.010(3) 0.006(3) 0.008(3) C22 0.064(5) 0.064(5) 0.045(4) 0.002(4) 0.002(4) 0.030(4) C23 0.058(5) 0.059(5) 0.064(5) 0.010(4) 0.018(4) 0.023(4) C24 0.094(7) 0.081(7) 0.087(7) 0.023(6) 0.018(6) 0.038(6) C25 0.093(7) 0.082(7) 0.078(6) 0.012(5) 0.021(6) 0.042(6) C26 0.100(7) 0.077(7) 0.080(7) 0.020(5) 0.006(6) 0.042(6) C27 0.075(6) 0.080(6) 0.063(5) 0.014(5) -0.001(5) 0.037(5) C28 0.053(5) 0.044(4) 0.040(4) -0.018(3) 0.009(4) 0.009(4) C29 0.083(6) 0.071(6) 0.105(7) 0.012(5) 0.021(5) 0.055(5) C210 0.090(7) 0.092(7) 0.136(9) 0.009(6) 0.022(6) 0.067(6) C211 0.095(7) 0.085(7) 0.107(8) 0.008(6) 0.005(6) 0.073(6) C212 0.066(6) 0.070(6) 0.069(6) 0.004(5) -0.007(5) 0.036(5) C213 0.032(4) 0.075(6) 0.058(5) -0.003(4) 0.001(4) 0.027(4) C214 0.052(5) 0.032(4) 0.033(4) 0.002(3) -0.001(3) 0.010(3) C215 0.053(5) 0.039(4) 0.053(5) -0.014(4) -0.019(4) 0.013(4) C216 0.050(5) 0.067(6) 0.070(6) -0.008(5) -0.006(4) 0.026(4) C217 0.059(5) 0.048(5) 0.064(5) -0.009(4) -0.003(4) 0.027(4) C218 0.057(5) 0.041(4) 0.047(4) -0.019(4) -0.011(4) 0.012(4) C219 0.042(4) 0.032(4) 0.037(4) -0.005(3) -0.003(3) 0.010(3) N3 0.028(3) 0.043(4) 0.030(3) 0.006(3) 0.003(3) 0.018(3) C31 0.021(3) 0.032(3) 0.040(4) 0.001(3) 0.001(3) 0.013(3) C32 0.043(4) 0.039(4) 0.047(4) 0.010(3) -0.005(3) 0.024(3) C33 0.110(8) 0.076(6) 0.092(7) -0.001(5) -0.026(6) 0.058(6) C34 0.138(9) 0.118(9) 0.128(9) 0.015(7) -0.053(7) 0.083(7) C35 0.122(8) 0.109(8) 0.096(7) -0.001(6) -0.063(6) 0.064(7) C36 0.079(6) 0.072(6) 0.056(5) -0.012(4) -0.016(4) 0.053(5) C37 0.074(6) 0.064(5) 0.048(5) 0.004(4) -0.014(4) 0.042(5) C38 0.042(4) 0.021(3) 0.048(4) 0.003(3) -0.004(3) 0.020(3) C39 0.051(5) 0.054(5) 0.080(6) 0.002(4) 0.012(4) 0.021(4) C310 0.072(6) 0.060(5) 0.082(6) -0.015(5) 0.025(5) 0.034(5) C311 0.082(6) 0.036(4) 0.050(5) -0.009(4) -0.003(4) 0.030(4) C312 0.050(5) 0.050(5) 0.084(6) -0.022(4) -0.001(4) 0.020(4) C313 0.041(4) 0.056(5) 0.073(5) -0.018(4) 0.007(4) 0.021(4) C314 0.033(4) 0.027(3) 0.039(4) -0.001(3) 0.005(3) 0.015(3) C315 0.033(4) 0.053(5) 0.051(4) 0.013(4) 0.000(3) 0.019(4) C316 0.055(5) 0.071(6) 0.065(5) 0.017(4) 0.011(4) 0.038(4) C317 0.040(4) 0.025(3) 0.055(5) 0.000(3) 0.007(3) 0.011(3) C318 0.028(4) 0.048(4) 0.057(4) 0.000(4) 0.011(3) 0.018(3) C319 0.036(4) 0.048(4) 0.045(4) 0.006(3) 0.002(3) 0.024(3) N4 0.041(4) 0.041(4) 0.027(6) 0.000 0.000 0.020(2) C41 0.044(4) 0.044(4) 0.032(6) 0.000 0.000 0.022(2) C42 0.045(4) 0.036(4) 0.045(4) 0.005(3) 0.007(3) 0.020(3) C43 0.062(5) 0.064(5) 0.057(5) 0.023(4) 0.002(4) 0.027(4) C44 0.084(7) 0.063(6) 0.073(6) 0.026(5) 0.013(5) 0.036(5) C45 0.069(6) 0.075(6) 0.098(7) -0.012(6) 0.019(6) 0.035(5) C46 0.070(6) 0.062(6) 0.057(6) 0.008(5) 0.005(5) 0.004(5) C47 0.059(5) 0.065(6) 0.055(5) 0.011(5) -0.002(4) 0.019(4) Cl1 0.101(3) 0.095(2) 0.111(3) 0.020(2) -0.016(2) 0.052(2) Cl2 0.118(4) 0.206(6) 0.154(5) 0.076(5) 0.014(3) 0.074(4) C100 0.100(7) 0.100(7) 0.104(11) 0.000 0.000 0.050(4) C101 0.225(11) 0.225(11) 0.237(16) 0.000 0.000 0.113(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C11 1.513(16) . ? N1 H1A 0.910 . ? C11 C12 1.521(9) . ? C11 C12 1.521(9) 3 ? C11 C12 1.521(9) 2 ? C12 C17 1.387(13) . ? C12 C13 1.416(12) . ? C13 C14 1.341(14) . ? C13 H13 0.950 . ? C14 C15 1.401(16) . ? C14 H14A 0.950 . ? C15 C16 1.376(15) . ? C15 H15A 0.950 . ? C16 C17 1.363(14) . ? C16 H16A 0.950 . ? C17 H17A 0.950 . ? N2 C21 1.518(10) . ? N2 H2A 0.910 . ? N2 H2B 0.910 . ? N2 H2C 0.910 . ? C21 C28 1.487(14) . ? C21 C214 1.516(12) . ? C21 C22 1.544(13) . ? C22 C23 1.288(14) . ? C22 C27 1.400(15) . ? C23 C24 1.409(15) . ? C23 H23A 0.950 . ? C24 C25 1.339(18) . ? C24 H24A 0.950 . ? C25 C26 1.373(19) . ? C25 H25A 0.950 . ? C26 C27 1.436(17) . ? C26 H26A 0.950 . ? C27 H27A 0.950 . ? C28 C213 1.379(14) . ? C28 C29 1.386(15) . ? C29 C210 1.436(18) . ? C29 H29A 0.950 . ? C210 C211 1.41(2) . ? C210 H21A 0.950 . ? C211 C212 1.366(17) . ? C211 H21B 0.950 . ? C212 C213 1.384(14) . ? C212 H21C 0.950 . ? C213 H21D 0.950 . ? C214 C219 1.367(11) . ? C214 C215 1.393(13) . ? C215 C216 1.446(14) . ? C215 H21E 0.950 . ? C216 C217 1.398(14) . ? C216 H21F 0.950 . ? C217 C218 1.331(14) . ? C217 H21H 0.950 . ? C218 C219 1.410(12) . ? C218 H21I 0.950 . ? C219 H21G 0.950 . ? N3 C31 1.494(9) . ? N3 H3A 0.910 . ? N3 H3B 0.910 . ? N3 H3C 0.910 . ? C31 C32 1.524(10) . ? C31 C38 1.527(10) . ? C31 C314 1.577(10) . ? C32 C37 1.365(13) . ? C32 C33 1.413(14) . ? C33 C34 1.334(18) . ? C33 H33A 0.950 . ? C34 C35 1.36(2) . ? C34 H34A 0.950 . ? C35 C36 1.236(18) . ? C35 H35A 0.950 . ? C36 C37 1.372(14) . ? C36 H36A 0.950 . ? C37 H37A 0.950 . ? C38 C313 1.347(12) . ? C38 C39 1.391(13) . ? C39 C310 1.343(15) . ? C39 H39A 0.950 . ? C310 C311 1.355(15) . ? C310 H31A 0.950 . ? C311 C312 1.387(14) . ? C311 H31B 0.950 . ? C312 C313 1.370(13) . ? C312 H31C 0.950 . ? C313 H31D 0.950 . ? C314 C319 1.372(11) . ? C314 C315 1.391(11) . ? C315 C316 1.342(13) . ? C315 H31E 0.950 . ? C316 C317 1.359(13) . ? C316 H31F 0.950 . ? C317 C318 1.399(12) . ? C317 H31G 0.950 . ? C318 C319 1.372(11) . ? C318 H31H 0.950 . ? C319 H31I 0.950 . ? N4 C41 1.488(18) . ? N4 H4A 0.910 . ? C41 C42 1.541(9) 3_565 ? C41 C42 1.541(9) . ? C41 C42 1.541(9) 2_665 ? C42 C43 1.358(13) . ? C42 C47 1.382(14) . ? C43 C44 1.409(16) . ? C43 H43A 0.950 . ? C44 C45 1.323(18) . ? C44 H44A 0.950 . ? C45 C46 1.401(19) . ? C45 H45A 0.950 . ? C46 C47 1.408(15) . ? C46 H46A 0.950 . ? C47 H47A 0.950 . ? Cl1 C100 1.780(7) . ? Cl2 C101 1.811(10) . ? C100 Cl1 1.780(7) 2_675 ? C100 Cl1 1.780(7) 3_465 ? C100 H10A 1.000 . ? C101 Cl2 1.811(10) 2_665 ? C101 Cl2 1.811(10) 3_565 ? C101 H10B 1.000 . ? 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 C11 N1 H1A 109.5 . . ? N1 C11 C12 107.9(5) . . ? N1 C11 C12 107.9(5) . 3 ? C12 C11 C12 111.0(5) . 3 ? N1 C11 C12 107.9(5) . 2 ? C12 C11 C12 111.0(5) . 2 ? C12 C11 C12 111.0(5) 3 2 ? C17 C12 C13 115.4(8) . . ? C17 C12 C11 122.7(8) . . ? C13 C12 C11 121.7(8) . . ? C14 C13 C12 121.5(10) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 122.6(10) . . ? C13 C14 H14A 118.7 . . ? C15 C14 H14A 118.7 . . ? C16 C15 C14 116.0(9) . . ? C16 C15 H15A 122.0 . . ? C14 C15 H15A 122.0 . . ? C17 C16 C15 122.0(10) . . ? C17 C16 H16A 119.0 . . ? C15 C16 H16A 119.0 . . ? C16 C17 C12 122.4(9) . . ? C16 C17 H17A 118.8 . . ? C12 C17 H17A 118.8 . . ? C21 N2 H2A 109.5 . . ? C21 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C21 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C28 C21 C214 113.4(7) . . ? C28 C21 N2 103.4(7) . . ? C214 C21 N2 109.5(7) . . ? C28 C21 C22 117.3(8) . . ? C214 C21 C22 105.0(7) . . ? N2 C21 C22 108.2(7) . . ? C23 C22 C27 117.7(10) . . ? C23 C22 C21 120.6(9) . . ? C27 C22 C21 121.7(9) . . ? C22 C23 C24 125.1(12) . . ? C22 C23 H23A 117.4 . . ? C24 C23 H23A 117.4 . . ? C25 C24 C23 119.0(13) . . ? C25 C24 H24A 120.5 . . ? C23 C24 H24A 120.5 . . ? C24 C25 C26 118.3(13) . . ? C24 C25 H25A 120.9 . . ? C26 C25 H25A 120.9 . . ? C25 C26 C27 121.3(13) . . ? C25 C26 H26A 119.3 . . ? C27 C26 H26A 119.3 . . ? C22 C27 C26 118.0(12) . . ? C22 C27 H27A 121.0 . . ? C26 C27 H27A 121.0 . . ? C213 C28 C29 118.6(10) . . ? C213 C28 C21 123.3(8) . . ? C29 C28 C21 118.2(9) . . ? C28 C29 C210 117.2(12) . . ? C28 C29 H29A 121.4 . . ? C210 C29 H29A 121.4 . . ? C211 C210 C29 121.5(12) . . ? C211 C210 H21A 119.2 . . ? C29 C210 H21A 119.2 . . ? C212 C211 C210 119.7(11) . . ? C212 C211 H21B 120.1 . . ? C210 C211 H21B 120.1 . . ? C211 C212 C213 117.4(11) . . ? C211 C212 H21C 121.3 . . ? C213 C212 H21C 121.3 . . ? C28 C213 C212 125.2(10) . . ? C28 C213 H21D 117.4 . . ? C212 C213 H21D 117.4 . . ? C219 C214 C215 119.0(8) . . ? C219 C214 C21 120.1(8) . . ? C215 C214 C21 120.7(7) . . ? C214 C215 C216 121.9(8) . . ? C214 C215 H21E 119.1 . . ? C216 C215 H21E 119.1 . . ? C217 C216 C215 116.0(9) . . ? C217 C216 H21F 122.0 . . ? C215 C216 H21F 122.0 . . ? C218 C217 C216 121.1(9) . . ? C218 C217 H21H 119.4 . . ? C216 C217 H21H 119.4 . . ? C217 C218 C219 122.9(9) . . ? C217 C218 H21I 118.5 . . ? C219 C218 H21I 118.5 . . ? C214 C219 C218 118.7(8) . . ? C214 C219 H21G 120.6 . . ? C218 C219 H21G 120.6 . . ? C31 N3 H3A 109.5 . . ? C31 N3 H3B 109.5 . . ? H3A N3 H3B 109.5 . . ? C31 N3 H3C 109.5 . . ? H3A N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? N3 C31 C32 112.1(6) . . ? N3 C31 C38 109.7(6) . . ? C32 C31 C38 113.7(6) . . ? N3 C31 C314 108.0(5) . . ? C32 C31 C314 105.5(4) . . ? C38 C31 C314 107.5(6) . . ? C37 C32 C33 117.8(9) . . ? C37 C32 C31 122.4(7) . . ? C33 C32 C31 119.8(9) . . ? C34 C33 C32 114.5(13) . . ? C34 C33 H33A 122.8 . . ? C32 C33 H33A 122.8 . . ? C33 C34 C35 125.6(14) . . ? C33 C34 H34A 117.2 . . ? C35 C34 H34A 117.2 . . ? C36 C35 C34 119.9(12) . . ? C36 C35 H35A 120.1 . . ? C34 C35 H35A 120.1 . . ? C35 C36 C37 120.0(11) . . ? C35 C36 H36A 120.0 . . ? C37 C36 H36A 120.0 . . ? C32 C37 C36 122.2(9) . . ? C32 C37 H37A 118.9 . . ? C36 C37 H37A 118.9 . . ? C313 C38 C39 115.8(8) . . ? C313 C38 C31 119.9(7) . . ? C39 C38 C31 124.4(8) . . ? C310 C39 C38 121.8(9) . . ? C310 C39 H39A 119.1 . . ? C38 C39 H39A 119.1 . . ? C39 C310 C311 122.4(9) . . ? C39 C310 H31A 118.8 . . ? C311 C310 H31A 118.8 . . ? C310 C311 C312 116.1(8) . . ? C310 C311 H31B 121.9 . . ? C312 C311 H31B 121.9 . . ? C313 C312 C311 120.8(10) . . ? C313 C312 H31C 119.6 . . ? C311 C312 H31C 119.6 . . ? C38 C313 C312 122.4(9) . . ? C38 C313 H31D 118.8 . . ? C312 C313 H31D 118.8 . . ? C319 C314 C315 117.0(7) . . ? C319 C314 C31 121.3(7) . . ? C315 C314 C31 121.6(7) . . ? C316 C315 C314 120.9(8) . . ? C316 C315 H31E 119.5 . . ? C314 C315 H31E 119.5 . . ? C315 C316 C317 122.9(9) . . ? C315 C316 H31F 118.6 . . ? C317 C316 H31F 118.6 . . ? C316 C317 C318 117.3(8) . . ? C316 C317 H31G 121.3 . . ? C318 C317 H31G 121.3 . . ? C319 C318 C317 119.8(7) . . ? C319 C318 H31H 120.1 . . ? C317 C318 H31H 120.1 . . ? C314 C319 C318 122.0(8) . . ? C314 C319 H31I 119.0 . . ? C318 C319 H31I 119.0 . . ? C41 N4 H4A 109.5 . . ? N4 C41 C42 107.7(6) . 3_565 ? N4 C41 C42 107.7(6) . . ? C42 C41 C42 111.1(6) 3_565 . ? N4 C41 C42 107.7(6) . 2_665 ? C42 C41 C42 111.1(6) 3_565 2_665 ? C42 C41 C42 111.1(6) . 2_665 ? C43 C42 C47 119.2(9) . . ? C43 C42 C41 121.9(9) . . ? C47 C42 C41 118.9(8) . . ? C42 C43 C44 120.2(10) . . ? C42 C43 H43A 119.9 . . ? C44 C43 H43A 119.9 . . ? C45 C44 C43 118.3(12) . . ? C45 C44 H44A 120.9 . . ? C43 C44 H44A 120.9 . . ? C44 C45 C46 125.7(13) . . ? C44 C45 H45A 117.1 . . ? C46 C45 H45A 117.1 . . ? C45 C46 C47 113.5(12) . . ? C45 C46 H46A 123.2 . . ? C47 C46 H46A 123.2 . . ? C42 C47 C46 122.8(11) . . ? C42 C47 H47A 118.6 . . ? C46 C47 H47A 118.6 . . ? Cl1 C100 Cl1 110.0(7) 2_675 3_465 ? Cl1 C100 Cl1 110.0(7) 2_675 . ? Cl1 C100 Cl1 110.0(7) 3_465 . ? Cl1 C100 H10A 109.0 2_675 . ? Cl1 C100 H10A 109.0 3_465 . ? Cl1 C100 H10A 109.0 . . ? Cl2 C101 Cl2 106.5(10) 2_665 3_565 ? Cl2 C101 Cl2 106.5(10) 2_665 . ? Cl2 C101 Cl2 106.5(10) 3_565 . ? Cl2 C101 H10B 112.3 2_665 . ? Cl2 C101 H10B 112.3 3_565 . ? Cl2 C101 H10B 112.3 . . ? 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 N1 C11 C12 C17 45.5(8) . . . . ? C12 C11 C12 C17 -72.5(13) 3 . . . ? C12 C11 C12 C17 163.6(8) 2 . . . ? N1 C11 C12 C13 -139.7(7) . . . . ? C12 C11 C12 C13 102.2(7) 3 . . . ? C12 C11 C12 C13 -21.6(12) 2 . . . ? C17 C12 C13 C14 0.3(14) . . . . ? C11 C12 C13 C14 -174.9(9) . . . . ? C12 C13 C14 C15 -0.7(17) . . . . ? C13 C14 C15 C16 0.3(17) . . . . ? C14 C15 C16 C17 0.4(17) . . . . ? C15 C16 C17 C12 -0.8(17) . . . . ? C13 C12 C17 C16 0.4(14) . . . . ? C11 C12 C17 C16 175.5(9) . . . . ? C28 C21 C22 C23 -73.0(12) . . . . ? C214 C21 C22 C23 53.8(12) . . . . ? N2 C21 C22 C23 170.6(10) . . . . ? C28 C21 C22 C27 106.7(11) . . . . ? C214 C21 C22 C27 -126.4(11) . . . . ? N2 C21 C22 C27 -9.6(14) . . . . ? C27 C22 C23 C24 -7.0(18) . . . . ? C21 C22 C23 C24 172.8(11) . . . . ? C22 C23 C24 C25 10(2) . . . . ? C23 C24 C25 C26 -6(2) . . . . ? C24 C25 C26 C27 2(2) . . . . ? C23 C22 C27 C26 1.7(17) . . . . ? C21 C22 C27 C26 -178.0(11) . . . . ? C25 C26 C27 C22 1(2) . . . . ? C214 C21 C28 C213 51.6(11) . . . . ? N2 C21 C28 C213 -66.8(10) . . . . ? C22 C21 C28 C213 174.2(9) . . . . ? C214 C21 C28 C29 -127.5(9) . . . . ? N2 C21 C28 C29 114.1(10) . . . . ? C22 C21 C28 C29 -4.9(12) . . . . ? C213 C28 C29 C210 -3.7(17) . . . . ? C21 C28 C29 C210 175.5(11) . . . . ? C28 C29 C210 C211 6(2) . . . . ? C29 C210 C211 C212 -2(2) . . . . ? C210 C211 C212 C213 -3.7(19) . . . . ? C29 C28 C213 C212 -2.2(16) . . . . ? C21 C28 C213 C212 178.7(9) . . . . ? C211 C212 C213 C28 6.0(17) . . . . ? C28 C21 C214 C219 30.4(11) . . . . ? N2 C21 C214 C219 145.3(8) . . . . ? C22 C21 C214 C219 -98.8(9) . . . . ? C28 C21 C214 C215 -154.6(8) . . . . ? N2 C21 C214 C215 -39.7(11) . . . . ? C22 C21 C214 C215 76.2(10) . . . . ? C219 C214 C215 C216 4.4(14) . . . . ? C21 C214 C215 C216 -170.7(9) . . . . ? C214 C215 C216 C217 -0.2(15) . . . . ? C215 C216 C217 C218 -1.3(15) . . . . ? C216 C217 C218 C219 -1.3(16) . . . . ? C215 C214 C219 C218 -6.9(12) . . . . ? C21 C214 C219 C218 168.2(8) . . . . ? C217 C218 C219 C214 5.6(14) . . . . ? N3 C31 C32 C37 -41.4(6) . . . . ? C38 C31 C32 C37 -166.5(6) . . . . ? C314 C31 C32 C37 75.9(6) . . . . ? N3 C31 C32 C33 138.7(6) . . . . ? C38 C31 C32 C33 13.5(6) . . . . ? C314 C31 C32 C33 -104.0(6) . . . . ? C37 C32 C33 C34 -0.2(4) . . . . ? C31 C32 C33 C34 179.7(3) . . . . ? C32 C33 C34 C35 0.5(6) . . . . ? C33 C34 C35 C36 -0.9(9) . . . . ? C34 C35 C36 C37 1.0(8) . . . . ? C33 C32 C37 C36 0.4(6) . . . . ? C31 C32 C37 C36 -179.6(4) . . . . ? C35 C36 C37 C32 -0.8(8) . . . . ? N3 C31 C38 C313 -34.2(10) . . . . ? C32 C31 C38 C313 92.2(8) . . . . ? C314 C31 C38 C313 -151.4(8) . . . . ? N3 C31 C38 C39 145.5(8) . . . . ? C32 C31 C38 C39 -88.1(9) . . . . ? C314 C31 C38 C39 28.3(10) . . . . ? C313 C38 C39 C310 -8.2(16) . . . . ? C31 C38 C39 C310 172.1(10) . . . . ? C38 C39 C310 C311 6.3(19) . . . . ? C39 C310 C311 C312 1.8(18) . . . . ? C310 C311 C312 C313 -7.6(17) . . . . ? C39 C38 C313 C312 2.3(15) . . . . ? C31 C38 C313 C312 -178.0(9) . . . . ? C311 C312 C313 C38 5.6(18) . . . . ? N3 C31 C314 C319 141.2(7) . . . . ? C32 C31 C314 C319 21.1(9) . . . . ? C38 C31 C314 C319 -100.6(8) . . . . ? N3 C31 C314 C315 -41.8(10) . . . . ? C32 C31 C314 C315 -161.9(7) . . . . ? C38 C31 C314 C315 76.4(9) . . . . ? C319 C314 C315 C316 1.2(13) . . . . ? C31 C314 C315 C316 -176.0(8) . . . . ? C314 C315 C316 C317 1.0(16) . . . . ? C315 C316 C317 C318 -1.8(15) . . . . ? C316 C317 C318 C319 0.5(13) . . . . ? C315 C314 C319 C318 -2.5(12) . . . . ? C31 C314 C319 C318 174.6(7) . . . . ? C317 C318 C319 C314 1.7(13) . . . . ? N4 C41 C42 C43 134.3(9) . . . . ? C42 C41 C42 C43 -107.9(8) 3_565 . . . ? C42 C41 C42 C43 16.5(14) 2_665 . . . ? N4 C41 C42 C47 -45.2(9) . . . . ? C42 C41 C42 C47 72.6(14) 3_565 . . . ? C42 C41 C42 C47 -163.0(9) 2_665 . . . ? C47 C42 C43 C44 -4.4(17) . . . . ? C41 C42 C43 C44 176.1(10) . . . . ? C42 C43 C44 C45 2.3(19) . . . . ? C43 C44 C45 C46 1(2) . . . . ? C44 C45 C46 C47 -2(2) . . . . ? C43 C42 C47 C46 3.3(18) . . . . ? C41 C42 C47 C46 -177.1(11) . . . . ? C45 C46 C47 C42 -0.1(19) . . . . ? 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 N1 H1A Br2 0.91 2.49 3.363(6) 159.6 . N2 H2A Br1 0.91 2.50 3.369(7) 159.7 . N2 H2C Br2 0.91 2.49 3.304(8) 149.6 . N2 H2B Br2 0.91 2.46 3.326(8) 159.8 3 N3 H3C Br3 0.91 2.50 3.349(7) 155.6 . N3 H3C Br3 0.91 2.50 3.349(7) 155.6 2_665 N3 H3C Br3 0.91 2.50 3.349(7) 155.6 3_565 N4 H4A Br4 0.91 2.47 3.321(6) 155.9 . #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 645315' _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 N +, I -, 0.5(C H Cl3)' _chemical_formula_sum 'C19.50 H18.50 Cl1.50 I N' _chemical_formula_weight 446.93 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' I I -0.4742 1.8119 '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 11.7438(4) _cell_length_b 11.9457(4) _cell_length_c 14.9678(5) _cell_angle_alpha 71.057(2) _cell_angle_beta 69.997(2) _cell_angle_gamma 85.534(2) _cell_volume 1864.97(11) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 8149 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 25.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 884 _exptl_absorpt_coefficient_mu 1.931 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.821 _exptl_absorpt_correction_T_max 0.910 _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.902327 ; _exptl_special_details ; Multiple crystal - ignored during integration. Some reflections suffer from overlap and have F(obs) greater than F(calc). Contributes to "high" R-factors. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay ? _diffrn_reflns_number 31828 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 26.74 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.74 _diffrn_measured_fraction_theta_full 0.981 _reflns_number_total 7767 _reflns_number_gt 6237 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-22 (Bruker Nonius, 2004)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10' _computing_molecular_graphics 'SHELXTL v.6.10' _computing_publication_material 'SHELXTL v.6.10' _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^)+56.6066P] 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 7767 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.2075 _refine_ls_wR_factor_gt 0.2038 _refine_ls_goodness_of_fit_ref 1.205 _refine_ls_restrained_S_all 1.205 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 2.309 _refine_diff_density_min -1.441 _refine_diff_density_rms 0.214 #highest peaks close to centres of benzene rings 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 I1 I 0.66488(6) 0.67691(6) 0.40512(5) 0.02749(19) Uani 1 1 d . . . I2 I 0.34698(6) 0.63367(6) 0.25713(5) 0.02630(19) Uani 1 1 d . . . N1 N 0.3437(8) 0.6434(8) 0.4916(6) 0.0227(18) Uani 1 1 d . . . H1A H 0.4221 0.6577 0.4839 0.034 Uiso 1 1 calc R . . H1B H 0.3352 0.6625 0.4303 0.034 Uiso 1 1 calc R . . H1C H 0.3234 0.5653 0.5253 0.034 Uiso 1 1 calc R . . C1 C 0.2606(9) 0.7182(9) 0.5510(7) 0.019(2) Uani 1 1 d . . . C11 C 0.3023(9) 0.8475(9) 0.4887(8) 0.024(2) Uani 1 1 d . . . C12 C 0.3116(11) 0.8907(10) 0.3886(9) 0.032(3) Uani 1 1 d . . . H12 H 0.2975 0.8381 0.3573 0.039 Uiso 1 1 calc R . . C13 C 0.3410(13) 1.0094(12) 0.3330(11) 0.045(3) Uani 1 1 d . . . H13 H 0.3442 1.0378 0.2650 0.054 Uiso 1 1 calc R . . C14 C 0.3652(13) 1.0850(12) 0.3766(13) 0.050(4) Uani 1 1 d . . . H14 H 0.3853 1.1663 0.3394 0.060 Uiso 1 1 calc R . . C15 C 0.3601(13) 1.0417(13) 0.4748(13) 0.050(4) Uani 1 1 d . . . H15 H 0.3805 1.0936 0.5040 0.059 Uiso 1 1 calc R . . C16 C 0.3269(11) 0.9277(11) 0.5317(10) 0.034(3) Uani 1 1 d . . . H16 H 0.3202 0.9019 0.6005 0.041 Uiso 1 1 calc R . . C17 C 0.2774(10) 0.6847(9) 0.6532(8) 0.023(2) Uani 1 1 d . . . C18 C 0.1834(10) 0.7049(11) 0.7329(8) 0.029(2) Uani 1 1 d . . . H18 H 0.1087 0.7324 0.7241 0.035 Uiso 1 1 calc R . . C19 C 0.1982(11) 0.6849(12) 0.8257(9) 0.034(3) Uani 1 1 d . . . H19 H 0.1340 0.6993 0.8796 0.041 Uiso 1 1 calc R . . C110 C 0.3062(12) 0.6445(11) 0.8384(9) 0.035(3) Uani 1 1 d . . . H110 H 0.3169 0.6293 0.9014 0.042 Uiso 1 1 calc R . . C111 C 0.4024(11) 0.6255(9) 0.7555(11) 0.035(3) Uani 1 1 d . . . H111 H 0.4784 0.6004 0.7628 0.042 Uiso 1 1 calc R . . C112 C 0.3863(10) 0.6428(10) 0.6683(9) 0.026(2) Uani 1 1 d . . . H112 H 0.4500 0.6263 0.6151 0.032 Uiso 1 1 calc R . . C113 C 0.0880(11) 0.5700(11) 0.6002(10) 0.039(3) Uani 1 1 d . . . H113 H 0.1388 0.5083 0.6205 0.047 Uiso 1 1 calc R . . C114 C 0.1299(9) 0.6878(9) 0.5610(7) 0.020(2) Uani 1 1 d . . . C115 C -0.0291(11) 0.5446(13) 0.6089(11) 0.044(3) Uani 1 1 d . . . H115 H -0.0572 0.4644 0.6320 0.052 Uiso 1 1 calc R . . C116 C -0.1054(12) 0.6342(13) 0.5846(9) 0.041(3) Uani 1 1 d . . . H116 H -0.1857 0.6148 0.5919 0.049 Uiso 1 1 calc R . . C117 C -0.0672(11) 0.7501(14) 0.5502(9) 0.043(3) Uani 1 1 d . . . H117 H -0.1208 0.8111 0.5345 0.051 Uiso 1 1 calc R . . C118 C 0.0524(10) 0.7785(10) 0.5381(8) 0.028(2) Uani 1 1 d . . . H118 H 0.0800 0.8589 0.5145 0.034 Uiso 1 1 calc R . . N2 N 0.6582(8) 0.6690(8) 0.1719(7) 0.0256(19) Uani 1 1 d . . . H2A H 0.6627 0.6946 0.2217 0.038 Uiso 1 1 calc R . . H2B H 0.6817 0.5928 0.1824 0.038 Uiso 1 1 calc R . . H2C H 0.5806 0.6730 0.1718 0.038 Uiso 1 1 calc R . . C2 C 0.7422(9) 0.7476(9) 0.0705(8) 0.022(2) Uani 1 1 d . . . C21 C 0.8692(10) 0.7343(10) 0.0760(8) 0.025(2) Uani 1 1 d . . . C22 C 0.9101(11) 0.6251(11) 0.1157(10) 0.041(3) Uani 1 1 d . . . H22 H 0.8589 0.5562 0.1404 0.049 Uiso 1 1 calc R . . C23 C 1.0288(15) 0.6163(18) 0.1192(14) 0.068(5) Uani 1 1 d . . . H23 H 1.0532 0.5408 0.1517 0.081 Uiso 1 1 calc R . . C24 C 1.1074(11) 0.7049(12) 0.0810(9) 0.035(3) Uani 1 1 d . . . H24 H 1.1883 0.6936 0.0813 0.042 Uiso 1 1 calc R . . C25 C 1.0690(11) 0.8150(12) 0.0403(11) 0.040(3) Uani 1 1 d . . . H25 H 1.1233 0.8820 0.0132 0.048 Uiso 1 1 calc R . . C26 C 0.9512(10) 0.8292(10) 0.0384(9) 0.030(2) Uani 1 1 d . . . H26 H 0.9262 0.9063 0.0105 0.036 Uiso 1 1 calc R . . C27 C 0.7309(10) 0.7018(9) -0.0101(8) 0.024(2) Uani 1 1 d . . . C28 C 0.8301(11) 0.7160(12) -0.0979(9) 0.036(3) Uani 1 1 d . . . H28 H 0.9050 0.7488 -0.1049 0.043 Uiso 1 1 calc R . . C29 C 0.8186(13) 0.6819(12) -0.1745(9) 0.039(3) Uani 1 1 d . . . H29 H 0.8867 0.6919 -0.2338 0.047 Uiso 1 1 calc R . . C210 C 0.7120(12) 0.6341(12) -0.1675(9) 0.038(3) Uani 1 1 d . . . H210 H 0.7062 0.6090 -0.2199 0.045 Uiso 1 1 calc R . . C211 C 0.6117(12) 0.6237(13) -0.0799(10) 0.044(3) Uani 1 1 d . . . H211 H 0.5356 0.5946 -0.0742 0.053 Uiso 1 1 calc R . . C212 C 0.6224(10) 0.6550(11) -0.0031(8) 0.032(3) Uani 1 1 d . . . H212 H 0.5544 0.6446 0.0564 0.038 Uiso 1 1 calc R . . C213 C 0.6974(9) 0.8739(10) 0.0582(8) 0.025(2) Uani 1 1 d . . . C214 C 0.6650(12) 0.9176(11) 0.1398(9) 0.035(3) Uani 1 1 d . . . H214 H 0.6716 0.8694 0.2022 0.043 Uiso 1 1 calc R . . C215 C 0.6233(13) 1.0311(13) 0.1288(10) 0.048(4) Uani 1 1 d . . . H215 H 0.6001 1.0600 0.1844 0.057 Uiso 1 1 calc R . . C216 C 0.6151(12) 1.1025(11) 0.0391(12) 0.047(4) Uani 1 1 d . . . H216 H 0.5877 1.1808 0.0320 0.056 Uiso 1 1 calc R . . C217 C 0.6468(13) 1.0599(12) -0.0401(12) 0.045(3) Uani 1 1 d . . . H217 H 0.6398 1.1090 -0.1021 0.054 Uiso 1 1 calc R . . C218 C 0.6890(12) 0.9465(11) -0.0320(10) 0.038(3) Uani 1 1 d . . . H218 H 0.7120 0.9190 -0.0883 0.045 Uiso 1 1 calc R . . C100 C 0.9517(13) 0.9192(12) 0.3077(10) 0.043(3) Uani 1 1 d . . . H100 H 0.8840 0.8732 0.3677 0.051 Uiso 1 1 calc R . . Cl1 Cl 0.8939(5) 0.9899(4) 0.2128(3) 0.0705(13) Uani 1 1 d . . . Cl2 Cl 1.0105(5) 1.0252(3) 0.3402(4) 0.0683(13) Uani 1 1 d . . . Cl3 Cl 1.0664(5) 0.8216(4) 0.2761(3) 0.0719(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0266(4) 0.0293(4) 0.0268(4) -0.0095(3) -0.0089(3) 0.0020(3) I2 0.0224(4) 0.0304(4) 0.0261(4) -0.0104(3) -0.0064(3) -0.0010(3) N1 0.021(4) 0.026(5) 0.022(4) -0.010(4) -0.005(3) 0.001(4) C1 0.017(5) 0.018(5) 0.022(5) -0.009(4) -0.004(4) 0.004(4) C11 0.019(5) 0.022(5) 0.029(6) -0.007(4) -0.007(4) 0.003(4) C12 0.038(7) 0.029(6) 0.033(6) -0.012(5) -0.013(5) 0.002(5) C13 0.041(8) 0.042(8) 0.038(7) 0.004(6) -0.009(6) -0.007(6) C14 0.043(8) 0.024(6) 0.077(11) -0.002(7) -0.025(8) -0.008(6) C15 0.036(7) 0.047(8) 0.074(11) -0.027(8) -0.020(7) 0.000(6) C16 0.033(6) 0.035(7) 0.045(7) -0.019(6) -0.019(6) 0.001(5) C17 0.024(5) 0.022(5) 0.027(5) -0.011(4) -0.010(4) 0.002(4) C18 0.024(6) 0.037(6) 0.029(6) -0.017(5) -0.006(5) 0.005(5) C19 0.030(6) 0.054(8) 0.028(6) -0.024(6) -0.012(5) 0.012(5) C110 0.043(7) 0.034(6) 0.035(7) -0.013(5) -0.021(6) 0.005(5) C111 0.041(7) 0.011(5) 0.075(9) -0.018(5) -0.044(7) 0.009(5) C112 0.021(5) 0.028(6) 0.033(6) -0.013(5) -0.010(5) 0.001(4) C113 0.027(6) 0.033(7) 0.047(8) -0.006(6) -0.005(6) -0.003(5) C114 0.021(5) 0.025(5) 0.014(5) -0.006(4) -0.006(4) 0.006(4) C115 0.025(6) 0.055(9) 0.056(8) -0.035(7) -0.001(6) -0.009(6) C116 0.026(6) 0.063(9) 0.032(7) -0.011(6) -0.008(5) -0.002(6) C117 0.019(6) 0.071(10) 0.029(6) -0.001(6) -0.015(5) 0.013(6) C118 0.022(5) 0.027(6) 0.026(6) -0.001(4) -0.004(4) -0.003(4) N2 0.024(5) 0.027(5) 0.024(5) -0.005(4) -0.008(4) -0.004(4) C2 0.020(5) 0.021(5) 0.022(5) -0.002(4) -0.006(4) -0.002(4) C21 0.022(5) 0.032(6) 0.025(5) -0.006(5) -0.018(4) 0.006(4) C22 0.026(6) 0.025(6) 0.054(8) 0.012(6) -0.015(6) -0.002(5) C23 0.042(9) 0.086(13) 0.073(12) -0.017(10) -0.026(8) 0.016(9) C24 0.024(6) 0.054(8) 0.031(6) -0.018(6) -0.013(5) 0.009(5) C25 0.029(6) 0.036(7) 0.062(9) -0.023(6) -0.015(6) -0.004(5) C26 0.025(6) 0.025(6) 0.044(7) -0.015(5) -0.010(5) 0.002(4) C27 0.023(5) 0.024(5) 0.021(5) -0.005(4) -0.005(4) -0.002(4) C28 0.022(6) 0.054(8) 0.034(6) -0.020(6) -0.004(5) -0.004(5) C29 0.048(8) 0.050(8) 0.029(6) -0.022(6) -0.016(6) 0.002(6) C210 0.045(7) 0.046(8) 0.028(6) -0.020(6) -0.013(5) 0.002(6) C211 0.033(7) 0.062(9) 0.037(7) -0.002(6) -0.019(6) -0.022(6) C212 0.020(5) 0.045(7) 0.025(6) -0.009(5) 0.001(4) -0.013(5) C213 0.020(5) 0.026(6) 0.030(6) -0.009(5) -0.009(4) 0.002(4) C214 0.040(7) 0.026(6) 0.032(6) -0.006(5) -0.004(5) -0.001(5) C215 0.044(8) 0.045(8) 0.033(7) -0.005(6) 0.006(6) 0.003(6) C216 0.029(7) 0.026(6) 0.081(11) -0.001(7) -0.029(7) 0.009(5) C217 0.049(8) 0.032(7) 0.061(9) -0.006(6) -0.035(7) 0.000(6) C218 0.038(7) 0.037(7) 0.038(7) -0.006(6) -0.018(6) 0.001(5) C100 0.046(8) 0.046(8) 0.031(7) -0.016(6) -0.001(6) -0.003(6) Cl1 0.097(3) 0.076(3) 0.060(3) -0.026(2) -0.053(3) 0.020(3) Cl2 0.099(3) 0.039(2) 0.096(3) -0.026(2) -0.067(3) 0.012(2) Cl3 0.099(4) 0.068(3) 0.057(2) -0.038(2) -0.026(2) 0.037(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.526(12) . ? N1 H1A 0.910 . ? N1 H1B 0.910 . ? N1 H1C 0.910 . ? C1 C17 1.529(14) . ? C1 C11 1.538(14) . ? C1 C114 1.551(14) . ? C11 C12 1.385(16) . ? C11 C16 1.409(15) . ? C12 C13 1.392(17) . ? C12 H12 0.950 . ? C13 C14 1.37(2) . ? C13 H13 0.950 . ? C14 C15 1.37(2) . ? C14 H14 0.950 . ? C15 C16 1.354(19) . ? C15 H15 0.950 . ? C16 H16 0.950 . ? C17 C18 1.394(15) . ? C17 C112 1.400(15) . ? C18 C19 1.401(16) . ? C18 H18 0.950 . ? C19 C110 1.373(17) . ? C19 H19 0.950 . ? C110 C111 1.433(18) . ? C110 H110 0.950 . ? C111 C112 1.330(16) . ? C111 H111 0.950 . ? C112 H112 0.950 . ? C113 C115 1.384(17) . ? C113 C114 1.393(16) . ? C113 H113 0.950 . ? C114 C118 1.393(15) . ? C115 C116 1.38(2) . ? C115 H115 0.950 . ? C116 C117 1.36(2) . ? C116 H116 0.950 . ? C117 C118 1.407(16) . ? C117 H117 0.950 . ? C118 H118 0.950 . ? N2 C2 1.534(13) . ? N2 H2A 0.910 . ? N2 H2B 0.910 . ? N2 H2C 0.910 . ? C2 C21 1.516(14) . ? C2 C27 1.524(14) . ? C2 C213 1.532(14) . ? C21 C22 1.370(15) . ? C21 C26 1.382(15) . ? C22 C23 1.408(19) . ? C22 H22 0.950 . ? C23 C24 1.30(2) . ? C23 H23 0.950 . ? C24 C25 1.371(18) . ? C24 H24 0.950 . ? C25 C26 1.390(16) . ? C25 H25 0.950 . ? C26 H26 0.950 . ? C27 C212 1.388(15) . ? C27 C28 1.396(15) . ? C28 C29 1.384(16) . ? C28 H28 0.950 . ? C29 C210 1.374(18) . ? C29 H29 0.950 . ? C210 C211 1.409(18) . ? C210 H210 0.950 . ? C211 C212 1.365(17) . ? C211 H211 0.950 . ? C212 H212 0.950 . ? C213 C218 1.379(16) . ? C213 C214 1.405(16) . ? C214 C215 1.383(18) . ? C214 H214 0.950 . ? C215 C216 1.368(19) . ? C215 H215 0.950 . ? C216 C217 1.36(2) . ? C216 H216 0.950 . ? C217 C218 1.388(18) . ? C217 H217 0.950 . ? C218 H218 0.950 . ? C100 Cl1 1.727(15) . ? C100 Cl3 1.753(14) . ? C100 Cl2 1.756(14) . ? C100 H100 1.000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 H1A 109.5 . . ? C1 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C1 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? N1 C1 C17 108.3(8) . . ? N1 C1 C11 105.5(8) . . ? C17 C1 C11 111.4(8) . . ? N1 C1 C114 105.9(8) . . ? C17 C1 C114 111.8(8) . . ? C11 C1 C114 113.5(8) . . ? C12 C11 C16 117.5(10) . . ? C12 C11 C1 120.6(10) . . ? C16 C11 C1 121.8(10) . . ? C11 C12 C13 121.5(12) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C14 C13 C12 119.7(13) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 119.0(13) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C16 C15 C14 122.4(13) . . ? C16 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? C15 C16 C11 119.8(13) . . ? C15 C16 H16 120.1 . . ? C11 C16 H16 120.1 . . ? C18 C17 C112 118.7(10) . . ? C18 C17 C1 118.4(9) . . ? C112 C17 C1 122.7(9) . . ? C17 C18 C19 120.6(10) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C110 C19 C18 119.6(11) . . ? C110 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C110 C111 119.1(11) . . ? C19 C110 H110 120.5 . . ? C111 C110 H110 120.5 . . ? C112 C111 C110 120.6(11) . . ? C112 C111 H111 119.7 . . ? C110 C111 H111 119.7 . . ? C111 C112 C17 121.4(11) . . ? C111 C112 H112 119.3 . . ? C17 C112 H112 119.3 . . ? C115 C113 C114 118.8(12) . . ? C115 C113 H113 120.6 . . ? C114 C113 H113 120.6 . . ? C118 C114 C113 120.3(10) . . ? C118 C114 C1 119.9(9) . . ? C113 C114 C1 119.6(9) . . ? C116 C115 C113 120.9(13) . . ? C116 C115 H115 119.6 . . ? C113 C115 H115 119.6 . . ? C117 C116 C115 120.9(12) . . ? C117 C116 H116 119.5 . . ? C115 C116 H116 119.5 . . ? C116 C117 C118 119.4(12) . . ? C116 C117 H117 120.3 . . ? C118 C117 H117 120.3 . . ? C114 C118 C117 119.5(11) . . ? C114 C118 H118 120.3 . . ? C117 C118 H118 120.3 . . ? C2 N2 H2A 109.5 . . ? C2 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C2 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C21 C2 C27 111.5(9) . . ? C21 C2 C213 113.2(9) . . ? C27 C2 C213 111.7(9) . . ? C21 C2 N2 106.2(8) . . ? C27 C2 N2 107.4(8) . . ? C213 C2 N2 106.4(8) . . ? C22 C21 C26 116.5(10) . . ? C22 C21 C2 120.8(10) . . ? C26 C21 C2 122.6(10) . . ? C21 C22 C23 119.2(13) . . ? C21 C22 H22 120.4 . . ? C23 C22 H22 120.4 . . ? C24 C23 C22 124.3(16) . . ? C24 C23 H23 117.8 . . ? C22 C23 H23 117.8 . . ? C23 C24 C25 117.5(13) . . ? C23 C24 H24 121.3 . . ? C25 C24 H24 121.3 . . ? C24 C25 C26 120.3(12) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C21 C26 C25 122.0(11) . . ? C21 C26 H26 119.0 . . ? C25 C26 H26 119.0 . . ? C212 C27 C28 118.6(10) . . ? C212 C27 C2 122.2(9) . . ? C28 C27 C2 119.0(10) . . ? C29 C28 C27 119.6(11) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C210 C29 C28 122.1(12) . . ? C210 C29 H29 118.9 . . ? C28 C29 H29 118.9 . . ? C29 C210 C211 117.6(11) . . ? C29 C210 H210 121.2 . . ? C211 C210 H210 121.2 . . ? C212 C211 C210 120.8(11) . . ? C212 C211 H211 119.6 . . ? C210 C211 H211 119.6 . . ? C211 C212 C27 121.2(11) . . ? C211 C212 H212 119.4 . . ? C27 C212 H212 119.4 . . ? C218 C213 C214 118.9(11) . . ? C218 C213 C2 121.3(10) . . ? C214 C213 C2 119.8(10) . . ? C215 C214 C213 119.6(12) . . ? C215 C214 H214 120.2 . . ? C213 C214 H214 120.2 . . ? C216 C215 C214 121.0(14) . . ? C216 C215 H215 119.5 . . ? C214 C215 H215 119.5 . . ? C217 C216 C215 119.3(13) . . ? C217 C216 H216 120.4 . . ? C215 C216 H216 120.4 . . ? C216 C217 C218 121.4(13) . . ? C216 C217 H217 119.3 . . ? C218 C217 H217 119.3 . . ? C213 C218 C217 119.8(13) . . ? C213 C218 H218 120.1 . . ? C217 C218 H218 120.1 . . ? Cl1 C100 Cl3 113.6(7) . . ? Cl1 C100 Cl2 109.5(8) . . ? Cl3 C100 Cl2 108.4(8) . . ? Cl1 C100 H100 108.4 . . ? Cl3 C100 H100 108.4 . . ? Cl2 C100 H100 108.4 . . ? 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 N1 C1 C11 C12 53.2(12) . . . . ? C17 C1 C11 C12 170.5(10) . . . . ? C114 C1 C11 C12 -62.3(13) . . . . ? N1 C1 C11 C16 -129.8(10) . . . . ? C17 C1 C11 C16 -12.5(13) . . . . ? C114 C1 C11 C16 114.7(11) . . . . ? C16 C11 C12 C13 -1.6(17) . . . . ? C1 C11 C12 C13 175.5(11) . . . . ? C11 C12 C13 C14 2(2) . . . . ? C12 C13 C14 C15 0(2) . . . . ? C13 C14 C15 C16 -3(2) . . . . ? C14 C15 C16 C11 3(2) . . . . ? C12 C11 C16 C15 -1.0(17) . . . . ? C1 C11 C16 C15 -178.1(11) . . . . ? N1 C1 C17 C18 -156.0(9) . . . . ? C11 C1 C17 C18 88.5(12) . . . . ? C114 C1 C17 C18 -39.7(13) . . . . ? N1 C1 C17 C112 28.8(13) . . . . ? C11 C1 C17 C112 -86.7(12) . . . . ? C114 C1 C17 C112 145.1(10) . . . . ? C112 C17 C18 C19 0.8(17) . . . . ? C1 C17 C18 C19 -174.6(11) . . . . ? C17 C18 C19 C110 -0.4(19) . . . . ? C18 C19 C110 C111 1.1(19) . . . . ? C19 C110 C111 C112 -2.4(18) . . . . ? C110 C111 C112 C17 2.8(17) . . . . ? C18 C17 C112 C111 -2.0(17) . . . . ? C1 C17 C112 C111 173.2(10) . . . . ? C115 C113 C114 C118 4.7(18) . . . . ? C115 C113 C114 C1 179.7(11) . . . . ? N1 C1 C114 C118 -131.2(9) . . . . ? C17 C1 C114 C118 111.1(10) . . . . ? C11 C1 C114 C118 -15.9(13) . . . . ? N1 C1 C114 C113 53.7(12) . . . . ? C17 C1 C114 C113 -64.0(12) . . . . ? C11 C1 C114 C113 169.0(10) . . . . ? C114 C113 C115 C116 -3(2) . . . . ? C113 C115 C116 C117 1(2) . . . . ? C115 C116 C117 C118 1(2) . . . . ? C113 C114 C118 C117 -3.1(17) . . . . ? C1 C114 C118 C117 -178.1(10) . . . . ? C116 C117 C118 C114 0.3(18) . . . . ? C27 C2 C21 C22 -72.6(14) . . . . ? C213 C2 C21 C22 160.6(11) . . . . ? N2 C2 C21 C22 44.2(14) . . . . ? C27 C2 C21 C26 104.8(12) . . . . ? C213 C2 C21 C26 -22.1(15) . . . . ? N2 C2 C21 C26 -138.5(11) . . . . ? C26 C21 C22 C23 2(2) . . . . ? C2 C21 C22 C23 179.8(13) . . . . ? C21 C22 C23 C24 -5(3) . . . . ? C22 C23 C24 C25 4(3) . . . . ? C23 C24 C25 C26 -2(2) . . . . ? C22 C21 C26 C25 0.2(18) . . . . ? C2 C21 C26 C25 -177.3(11) . . . . ? C24 C25 C26 C21 -1(2) . . . . ? C21 C2 C27 C212 150.7(11) . . . . ? C213 C2 C27 C212 -81.6(13) . . . . ? N2 C2 C27 C212 34.7(14) . . . . ? C21 C2 C27 C28 -34.6(14) . . . . ? C213 C2 C27 C28 93.1(12) . . . . ? N2 C2 C27 C28 -150.6(10) . . . . ? C212 C27 C28 C29 -0.9(19) . . . . ? C2 C27 C28 C29 -175.7(11) . . . . ? C27 C28 C29 C210 0(2) . . . . ? C28 C29 C210 C211 2(2) . . . . ? C29 C210 C211 C212 -3(2) . . . . ? C210 C211 C212 C27 2(2) . . . . ? C28 C27 C212 C211 -0.3(19) . . . . ? C2 C27 C212 C211 174.4(12) . . . . ? C21 C2 C213 C218 106.5(12) . . . . ? C27 C2 C213 C218 -20.2(14) . . . . ? N2 C2 C213 C218 -137.2(10) . . . . ? C21 C2 C213 C214 -73.0(13) . . . . ? C27 C2 C213 C214 160.2(10) . . . . ? N2 C2 C213 C214 43.3(13) . . . . ? C218 C213 C214 C215 1.2(18) . . . . ? C2 C213 C214 C215 -179.3(11) . . . . ? C213 C214 C215 C216 -1(2) . . . . ? C214 C215 C216 C217 1(2) . . . . ? C215 C216 C217 C218 -1(2) . . . . ? C214 C213 C218 C217 -1.2(18) . . . . ? C2 C213 C218 C217 179.2(11) . . . . ? C216 C217 C218 C213 1(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 N1 H1A I1 0.91 2.68 3.552(9) 160.1 . N1 H1C I1 0.91 2.75 3.627(9) 162.5 2_666 N1 H1B I2 0.91 2.68 3.536(9) 157.2 . N2 H2A I1 0.91 2.69 3.550(9) 157.1 . N2 H2C I2 0.91 2.61 3.445(9) 153.6 . #===END data_H2O_dimer _database_code_depnum_ccdc_archive 'CCDC 645316' _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19 H18 N +), 2(Cl -), 5(H2 O)' _chemical_formula_sum 'C38 H46 Cl2 N2 O5' _chemical_formula_weight 681.67 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.4159(7) _cell_length_b 16.0171(11) _cell_length_c 12.8196(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.049(3) _cell_angle_gamma 90.00 _cell_volume 1883.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4992 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 24.54 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.859 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.877123 ; _exptl_special_details ; H atoms on N and O located in difference Fourier. All six N---H bonds restrained to be equivalent, and all H...H distances restrained to be 1.633 times that bond length (one parameter refined). U~iso~ values refined for all of these H atoms. All ten O---H bonds restrained to be equivalent, and all H...H distances restrained to be 1.58 times that bond length (one parameter refined). U~iso~(H) = 1.5 x U~eq~(O). ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 15825 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 28.21 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.21 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 4782 _reflns_number_gt 3960 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-22 (Bruker Nonius, 2004)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a (Bruker, 2003)' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL v.6.10 (Sheldrick, 2000)' _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^)+(0.0534P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; Absolute structure cannot be determined. 3477 Friedel pairs merged for final cycles of refinement. ; _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 4782 _refine_ls_number_parameters 480 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.260 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.041 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 Cl1 Cl 0.78113(6) 0.25519(4) 0.50137(5) 0.03373(15) Uani 1 1 d . . . Cl2 Cl 0.65887(7) 0.54781(4) 0.47244(5) 0.03483(16) Uani 1 1 d . . . N1 N 0.84713(19) 0.41701(12) 0.36772(15) 0.0227(4) Uani 1 1 d D . . H11 H 0.9484(15) 0.4298(12) 0.3964(17) 0.033(7) Uiso 1 1 d D . . H12 H 0.788(2) 0.4608(11) 0.387(2) 0.047(8) Uiso 1 1 d D . . H13 H 0.824(2) 0.3661(10) 0.4005(19) 0.043(8) Uiso 1 1 d D . . N2 N 0.6174(2) 0.38956(13) 0.61741(15) 0.0234(4) Uani 1 1 d D . . H21 H 0.5155(15) 0.3763(13) 0.5965(18) 0.033(7) Uiso 1 1 d D . . H22 H 0.632(2) 0.4430(10) 0.585(2) 0.056(9) Uiso 1 1 d D . . H23 H 0.673(2) 0.3486(12) 0.5883(19) 0.042(8) Uiso 1 1 d D . . C1 C 0.8120(2) 0.40930(14) 0.24590(17) 0.0210(5) Uani 1 1 d . . . C2 C 0.6664(2) 0.40006(14) 0.73834(16) 0.0212(5) Uani 1 1 d . . . C11 C 0.6441(2) 0.41171(14) 0.20790(18) 0.0230(5) Uani 1 1 d . . . C12 C 0.5586(2) 0.36190(18) 0.2583(2) 0.0361(6) Uani 1 1 d . . . H12A H 0.6039 0.3275 0.3167 0.043 Uiso 1 1 calc R . . C13 C 0.4072(3) 0.3620(2) 0.2239(2) 0.0439(7) Uani 1 1 d . . . H13A H 0.3497 0.3279 0.2589 0.053 Uiso 1 1 calc R . . C14 C 0.3410(2) 0.41187(19) 0.1390(2) 0.0451(8) Uani 1 1 d . . . H14A H 0.2377 0.4127 0.1162 0.054 Uiso 1 1 calc R . . C15 C 0.4246(3) 0.46050(18) 0.0870(2) 0.0392(6) Uani 1 1 d . . . H15A H 0.3787 0.4939 0.0277 0.047 Uiso 1 1 calc R . . C16 C 0.5763(2) 0.46082(16) 0.12106(19) 0.0301(5) Uani 1 1 d . . . H16A H 0.6333 0.4945 0.0851 0.036 Uiso 1 1 calc R . . C21 C 0.8728(2) 0.32518(15) 0.21855(17) 0.0218(5) Uani 1 1 d . . . C22 C 1.0072(3) 0.29590(18) 0.2761(2) 0.0354(6) Uani 1 1 d . . . H22A H 1.0615 0.3281 0.3337 0.042 Uiso 1 1 calc R . . C23 C 1.0626(3) 0.2205(2) 0.2505(2) 0.0464(7) Uani 1 1 d . . . H23A H 1.1541 0.2012 0.2906 0.056 Uiso 1 1 calc R . . C24 C 0.9845(3) 0.17276(18) 0.1659(2) 0.0393(7) Uani 1 1 d . . . H24A H 1.0213 0.1205 0.1487 0.047 Uiso 1 1 calc R . . C25 C 0.8526(3) 0.20254(18) 0.1073(2) 0.0364(6) Uani 1 1 d . . . H25A H 0.7992 0.1708 0.0488 0.044 Uiso 1 1 calc R . . C26 C 0.7973(2) 0.27802(16) 0.13287(18) 0.0278(5) Uani 1 1 d . . . H26A H 0.7069 0.2978 0.0914 0.033 Uiso 1 1 calc R . . C31 C 0.8833(2) 0.48386(15) 0.20314(17) 0.0231(5) Uani 1 1 d . . . C32 C 0.8700(3) 0.56364(17) 0.24242(19) 0.0356(6) Uani 1 1 d . . . H32A H 0.8185 0.5713 0.2974 0.043 Uiso 1 1 calc R . . C33 C 0.9306(3) 0.63237(19) 0.2027(2) 0.0437(7) Uani 1 1 d . . . H33A H 0.9212 0.6865 0.2306 0.052 Uiso 1 1 calc R . . C34 C 1.0050(3) 0.62121(19) 0.1219(2) 0.0403(7) Uani 1 1 d . . . H34A H 1.0480 0.6678 0.0950 0.048 Uiso 1 1 calc R . . C35 C 1.0170(3) 0.54317(19) 0.08052(19) 0.0359(6) Uani 1 1 d . . . H35A H 1.0669 0.5362 0.0244 0.043 Uiso 1 1 calc R . . C36 C 0.9561(2) 0.47391(16) 0.12056(19) 0.0287(5) Uani 1 1 d . . . H36A H 0.9644 0.4201 0.0915 0.034 Uiso 1 1 calc R . . C41 C 0.8334(2) 0.39936(15) 0.76624(18) 0.0250(5) Uani 1 1 d . . . C42 C 0.9127(2) 0.35529(17) 0.85433(19) 0.0324(6) Uani 1 1 d . . . H42A H 0.8628 0.3235 0.8974 0.039 Uiso 1 1 calc R . . C43 C 1.0640(3) 0.35756(19) 0.8794(2) 0.0454(7) Uani 1 1 d . . . H43A H 1.1169 0.3275 0.9396 0.055 Uiso 1 1 calc R . . C44 C 1.1383(3) 0.4034(2) 0.8172(3) 0.0521(9) Uani 1 1 d . . . H44A H 1.2419 0.4046 0.8346 0.062 Uiso 1 1 calc R . . C45 C 1.0615(3) 0.4473(2) 0.7297(2) 0.0488(8) Uani 1 1 d . . . H45A H 1.1124 0.4782 0.6864 0.059 Uiso 1 1 calc R . . C46 C 0.9102(2) 0.44646(19) 0.7048(2) 0.0373(6) Uani 1 1 d . . . H46A H 0.8581 0.4780 0.6457 0.045 Uiso 1 1 calc R . . C51 C 0.6067(2) 0.48425(15) 0.76706(17) 0.0225(5) Uani 1 1 d . . . C52 C 0.6890(2) 0.53327(16) 0.84874(18) 0.0286(6) Uani 1 1 d . . . H52A H 0.7835 0.5154 0.8848 0.034 Uiso 1 1 calc R . . C53 C 0.6340(3) 0.60785(18) 0.8778(2) 0.0383(6) Uani 1 1 d . . . H53A H 0.6910 0.6407 0.9335 0.046 Uiso 1 1 calc R . . C54 C 0.4963(3) 0.63477(19) 0.8259(2) 0.0416(7) Uani 1 1 d . . . H54A H 0.4592 0.6862 0.8455 0.050 Uiso 1 1 calc R . . C55 C 0.4134(3) 0.58627(18) 0.7455(2) 0.0393(6) Uani 1 1 d . . . H55A H 0.3187 0.6044 0.7100 0.047 Uiso 1 1 calc R . . C56 C 0.4673(2) 0.51127(17) 0.7162(2) 0.0330(6) Uani 1 1 d . . . H56A H 0.4090 0.4782 0.6613 0.040 Uiso 1 1 calc R . . C61 C 0.6026(2) 0.32647(15) 0.78860(17) 0.0227(5) Uani 1 1 d . . . C62 C 0.6204(3) 0.24532(18) 0.7540(2) 0.0373(6) Uani 1 1 d . . . H62A H 0.6726 0.2363 0.6997 0.045 Uiso 1 1 calc R . . C63 C 0.5627(3) 0.1778(2) 0.7980(2) 0.0458(7) Uani 1 1 d . . . H63A H 0.5754 0.1229 0.7737 0.055 Uiso 1 1 calc R . . C64 C 0.4856(3) 0.19047(19) 0.8783(2) 0.0388(6) Uani 1 1 d . . . H64A H 0.4441 0.1445 0.9076 0.047 Uiso 1 1 calc R . . C65 C 0.4707(2) 0.27043(17) 0.91432(19) 0.0332(6) Uani 1 1 d . . . H65A H 0.4207 0.2793 0.9700 0.040 Uiso 1 1 calc R . . C66 C 0.5278(2) 0.33769(16) 0.87023(18) 0.0258(5) Uani 1 1 d . . . H66A H 0.5162 0.3924 0.8957 0.031 Uiso 1 1 calc R . . O1 O 0.6997(2) 0.07813(14) 0.5999(2) 0.0565(6) Uani 1 1 d D . . H1 H 0.707(3) 0.1248(17) 0.565(3) 0.085 Uiso 1 1 d D . . H2 H 0.6069(19) 0.068(2) 0.588(3) 0.085 Uiso 1 1 d D . . O2 O 0.12861(19) 0.45923(13) 0.45887(17) 0.0439(5) Uani 1 1 d D . . H3 H 0.186(3) 0.4163(14) 0.472(3) 0.066 Uiso 1 1 d D . . H4 H 0.175(3) 0.4957(15) 0.429(2) 0.066 Uiso 1 1 d D . . O3 O 0.33050(19) 0.33326(13) 0.53716(16) 0.0420(5) Uani 1 1 d D . . H5 H 0.280(3) 0.3090(17) 0.577(2) 0.063 Uiso 1 1 d D . . H6 H 0.357(3) 0.2942(15) 0.499(2) 0.063 Uiso 1 1 d D . . O4 O 0.1351(2) 0.21534(16) 0.5712(2) 0.0634(7) Uani 1 1 d D . . H7 H 0.0428(19) 0.215(3) 0.537(3) 0.095 Uiso 1 1 d D . . H8 H 0.175(3) 0.176(2) 0.540(3) 0.095 Uiso 1 1 d D . . O5 O 0.4290(2) 0.21504(13) 0.41730(17) 0.0482(5) Uani 1 1 d D . . H9 H 0.5245(16) 0.215(2) 0.435(3) 0.072 Uiso 1 1 d D . . H10 H 0.402(3) 0.1711(16) 0.448(3) 0.072 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0375(3) 0.0269(3) 0.0408(3) 0.0033(3) 0.0172(3) 0.0026(3) Cl2 0.0396(3) 0.0287(3) 0.0407(3) 0.0046(3) 0.0186(3) 0.0087(3) N1 0.0214(8) 0.0228(11) 0.0246(9) 0.0025(8) 0.0068(7) 0.0009(8) N2 0.0224(9) 0.0233(11) 0.0251(9) -0.0015(8) 0.0064(7) -0.0008(8) C1 0.0205(9) 0.0199(13) 0.0229(10) 0.0004(9) 0.0058(8) -0.0003(9) C2 0.0196(9) 0.0229(13) 0.0212(10) -0.0008(9) 0.0048(8) -0.0004(9) C11 0.0205(9) 0.0211(13) 0.0277(11) -0.0041(9) 0.0064(9) 0.0018(9) C12 0.0244(11) 0.0393(16) 0.0436(14) 0.0054(12) 0.0057(10) -0.0010(11) C13 0.0251(12) 0.0529(19) 0.0557(17) 0.0039(15) 0.0135(12) -0.0062(12) C14 0.0181(10) 0.0483(19) 0.0652(19) -0.0107(15) 0.0017(12) 0.0064(12) C15 0.0296(12) 0.0351(16) 0.0466(15) -0.0003(13) -0.0050(11) 0.0099(12) C16 0.0280(11) 0.0273(14) 0.0335(12) 0.0012(11) 0.0039(10) 0.0079(10) C21 0.0199(10) 0.0211(13) 0.0263(11) 0.0003(9) 0.0093(8) 0.0006(9) C22 0.0287(12) 0.0328(15) 0.0402(13) -0.0105(12) -0.0018(11) 0.0097(11) C23 0.0354(14) 0.0480(19) 0.0510(17) -0.0058(14) -0.0005(12) 0.0179(13) C24 0.0401(14) 0.0283(16) 0.0522(16) -0.0081(13) 0.0160(12) 0.0091(12) C25 0.0336(13) 0.0337(17) 0.0431(14) -0.0155(13) 0.0113(11) -0.0036(12) C26 0.0225(10) 0.0283(15) 0.0326(12) -0.0035(10) 0.0058(9) -0.0005(9) C31 0.0210(10) 0.0242(13) 0.0238(10) 0.0038(10) 0.0042(8) 0.0005(9) C32 0.0524(15) 0.0263(16) 0.0335(12) -0.0017(11) 0.0207(11) -0.0021(12) C33 0.0645(19) 0.0249(16) 0.0465(16) -0.0002(13) 0.0228(14) -0.0062(14) C34 0.0456(15) 0.0327(17) 0.0450(15) 0.0104(13) 0.0151(13) -0.0092(13) C35 0.0340(12) 0.0391(16) 0.0398(13) 0.0132(13) 0.0191(10) 0.0037(12) C36 0.0260(11) 0.0283(14) 0.0341(13) 0.0018(11) 0.0115(10) 0.0017(10) C41 0.0210(9) 0.0234(13) 0.0301(11) -0.0047(10) 0.0048(9) 0.0030(9) C42 0.0313(12) 0.0297(14) 0.0346(12) -0.0018(11) 0.0039(10) 0.0058(11) C43 0.0341(13) 0.0439(18) 0.0499(16) -0.0060(14) -0.0081(12) 0.0136(13) C44 0.0190(11) 0.058(2) 0.076(2) -0.0096(18) 0.0040(13) 0.0009(13) C45 0.0279(13) 0.058(2) 0.0613(19) -0.0024(16) 0.0125(13) -0.0067(13) C46 0.0252(11) 0.0451(17) 0.0414(14) 0.0050(13) 0.0071(10) -0.0017(11) C51 0.0225(10) 0.0201(12) 0.0273(11) 0.0020(9) 0.0105(9) -0.0011(9) C52 0.0266(11) 0.0268(15) 0.0336(12) -0.0032(10) 0.0090(9) -0.0010(10) C53 0.0431(15) 0.0268(15) 0.0483(15) -0.0108(12) 0.0177(13) -0.0060(12) C54 0.0482(16) 0.0261(16) 0.0573(17) -0.0051(13) 0.0262(14) 0.0048(12) C55 0.0326(13) 0.0326(16) 0.0547(16) 0.0015(13) 0.0138(12) 0.0125(12) C56 0.0249(11) 0.0320(15) 0.0416(14) -0.0029(11) 0.0067(10) 0.0023(11) C61 0.0208(10) 0.0221(13) 0.0234(11) 0.0021(10) 0.0011(8) -0.0012(9) C62 0.0559(16) 0.0266(16) 0.0343(13) -0.0005(11) 0.0209(12) -0.0021(12) C63 0.075(2) 0.0218(16) 0.0435(15) -0.0012(12) 0.0198(15) -0.0084(14) C64 0.0489(15) 0.0307(16) 0.0386(13) 0.0074(13) 0.0137(12) -0.0110(13) C65 0.0281(11) 0.0386(17) 0.0344(13) 0.0064(11) 0.0098(10) -0.0001(11) C66 0.0251(10) 0.0239(13) 0.0280(11) 0.0009(10) 0.0054(9) 0.0025(10) O1 0.0480(12) 0.0367(13) 0.0876(17) -0.0009(12) 0.0212(12) 0.0021(10) O2 0.0297(9) 0.0397(12) 0.0579(12) 0.0074(10) 0.0006(8) -0.0045(8) O3 0.0314(9) 0.0385(12) 0.0539(12) 0.0038(9) 0.0049(8) -0.0039(9) O4 0.0485(12) 0.0563(15) 0.0900(18) 0.0143(13) 0.0254(12) 0.0009(11) O5 0.0471(11) 0.0404(12) 0.0584(13) 0.0081(10) 0.0144(10) -0.0009(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.526(3) . ? N1 H11 0.96(1) . ? N1 H12 0.96(1) . ? N1 H13 0.97(1) . ? N2 C2 1.524(3) . ? N2 H21 0.96(1) . ? N2 H22 0.97(1) . ? N2 H23 0.96(1) . ? C1 C31 1.531(3) . ? C1 C21 1.535(3) . ? C1 C11 1.546(3) . ? C2 C61 1.530(3) . ? C2 C41 1.533(3) . ? C2 C51 1.537(3) . ? C11 C12 1.392(3) . ? C11 C16 1.394(3) . ? C12 C13 1.394(3) . ? C12 H12A 0.950 . ? C13 C14 1.380(4) . ? C13 H13A 0.950 . ? C14 C15 1.381(4) . ? C14 H14A 0.950 . ? C15 C16 1.396(3) . ? C15 H15A 0.950 . ? C16 H16A 0.950 . ? C21 C26 1.389(3) . ? C21 C22 1.394(3) . ? C22 C23 1.385(4) . ? C22 H22A 0.950 . ? C23 C24 1.393(4) . ? C23 H23A 0.950 . ? C24 C25 1.383(4) . ? C24 H24A 0.950 . ? C25 C26 1.385(4) . ? C25 H25A 0.950 . ? C26 H26A 0.950 . ? C31 C32 1.389(4) . ? C31 C36 1.394(3) . ? C32 C33 1.389(4) . ? C32 H32A 0.950 . ? C33 C34 1.387(4) . ? C33 H33A 0.950 . ? C34 C35 1.372(4) . ? C34 H34A 0.950 . ? C35 C36 1.399(4) . ? C35 H35A 0.950 . ? C36 H36A 0.950 . ? C41 C42 1.396(3) . ? C41 C46 1.403(3) . ? C42 C43 1.389(3) . ? C42 H42A 0.950 . ? C43 C44 1.384(4) . ? C43 H43A 0.950 . ? C44 C45 1.383(4) . ? C44 H44A 0.950 . ? C45 C46 1.388(3) . ? C45 H45A 0.950 . ? C46 H46A 0.950 . ? C51 C52 1.395(3) . ? C51 C56 1.397(3) . ? C52 C53 1.386(4) . ? C52 H52A 0.950 . ? C53 C54 1.385(4) . ? C53 H53A 0.950 . ? C54 C55 1.383(4) . ? C54 H54A 0.950 . ? C55 C56 1.389(4) . ? C55 H55A 0.950 . ? C56 H56A 0.950 . ? C61 C62 1.396(4) . ? C61 C66 1.398(3) . ? C62 C63 1.386(4) . ? C62 H62A 0.950 . ? C63 C64 1.402(4) . ? C63 H63A 0.950 . ? C64 C65 1.379(4) . ? C64 H64A 0.950 . ? C65 C66 1.381(4) . ? C65 H65A 0.950 . ? C66 H66A 0.950 . ? O1 H1 0.88(1) . ? O1 H2 0.87(2) . ? O2 H3 0.87(1) . ? O2 H4 0.87(1) . ? O3 H5 0.86(1) . ? O3 H6 0.87(1) . ? O4 H7 0.88(2) . ? O4 H8 0.88(2) . ? O5 H9 0.88(1) . ? O5 H10 0.88(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 H11 112.1(13) . . ? C1 N1 H12 108.7(15) . . ? H11 N1 H12 109.0(12) . . ? C1 N1 H13 111.1(15) . . ? H11 N1 H13 108.4(12) . . ? H12 N1 H13 107.5(12) . . ? C2 N2 H21 111.3(14) . . ? C2 N2 H22 107.0(16) . . ? H21 N2 H22 108.0(12) . . ? C2 N2 H23 113.8(15) . . ? H21 N2 H23 109.6(12) . . ? H22 N2 H23 106.9(12) . . ? N1 C1 C31 106.97(17) . . ? N1 C1 C21 107.38(17) . . ? C31 C1 C21 112.72(17) . . ? N1 C1 C11 106.89(16) . . ? C31 C1 C11 111.58(17) . . ? C21 C1 C11 110.96(17) . . ? N2 C2 C61 106.62(17) . . ? N2 C2 C41 107.19(17) . . ? C61 C2 C41 112.10(18) . . ? N2 C2 C51 107.31(18) . . ? C61 C2 C51 112.06(17) . . ? C41 C2 C51 111.22(17) . . ? C12 C11 C16 119.0(2) . . ? C12 C11 C1 119.8(2) . . ? C16 C11 C1 121.1(2) . . ? C11 C12 C13 120.7(2) . . ? C11 C12 H12A 119.6 . . ? C13 C12 H12A 119.7 . . ? C14 C13 C12 119.8(3) . . ? C14 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? C13 C14 C15 120.1(2) . . ? C13 C14 H14A 119.9 . . ? C15 C14 H14A 119.9 . . ? C14 C15 C16 120.4(2) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? C11 C16 C15 119.9(2) . . ? C11 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C26 C21 C22 118.5(2) . . ? C26 C21 C1 120.47(19) . . ? C22 C21 C1 121.0(2) . . ? C23 C22 C21 120.9(2) . . ? C23 C22 H22A 119.6 . . ? C21 C22 H22A 119.6 . . ? C22 C23 C24 120.2(2) . . ? C22 C23 H23A 119.9 . . ? C24 C23 H23A 119.9 . . ? C25 C24 C23 119.0(3) . . ? C25 C24 H24A 120.5 . . ? C23 C24 H24A 120.5 . . ? C24 C25 C26 120.8(2) . . ? C24 C25 H25A 119.6 . . ? C26 C25 H25A 119.6 . . ? C25 C26 C21 120.6(2) . . ? C25 C26 H26A 119.7 . . ? C21 C26 H26A 119.7 . . ? C32 C31 C36 118.7(2) . . ? C32 C31 C1 120.3(2) . . ? C36 C31 C1 120.9(2) . . ? C33 C32 C31 121.2(2) . . ? C33 C32 H32A 119.4 . . ? C31 C32 H32A 119.4 . . ? C34 C33 C32 119.4(3) . . ? C34 C33 H33A 120.3 . . ? C32 C33 H33A 120.3 . . ? C35 C34 C33 120.4(3) . . ? C35 C34 H34A 119.8 . . ? C33 C34 H34A 119.8 . . ? C34 C35 C36 120.3(2) . . ? C34 C35 H35A 119.9 . . ? C36 C35 H35A 119.9 . . ? C31 C36 C35 120.0(2) . . ? C31 C36 H36A 120.0 . . ? C35 C36 H36A 120.0 . . ? C42 C41 C46 118.5(2) . . ? C42 C41 C2 121.7(2) . . ? C46 C41 C2 119.8(2) . . ? C43 C42 C41 120.5(3) . . ? C43 C42 H42A 119.8 . . ? C41 C42 H42A 119.8 . . ? C44 C43 C42 120.4(3) . . ? C44 C43 H43A 119.8 . . ? C42 C43 H43A 119.8 . . ? C45 C44 C43 119.8(2) . . ? C45 C44 H44A 120.1 . . ? C43 C44 H44A 120.1 . . ? C44 C45 C46 120.2(3) . . ? C44 C45 H45A 119.9 . . ? C46 C45 H45A 119.9 . . ? C45 C46 C41 120.6(2) . . ? C45 C46 H46A 119.7 . . ? C41 C46 H46A 119.7 . . ? C52 C51 C56 118.7(2) . . ? C52 C51 C2 120.17(19) . . ? C56 C51 C2 121.1(2) . . ? C53 C52 C51 120.6(2) . . ? C53 C52 H52A 119.7 . . ? C51 C52 H52A 119.7 . . ? C54 C53 C52 120.4(3) . . ? C54 C53 H53A 119.8 . . ? C52 C53 H53A 119.8 . . ? C55 C54 C53 119.5(3) . . ? C55 C54 H54A 120.2 . . ? C53 C54 H54A 120.2 . . ? C54 C55 C56 120.5(2) . . ? C54 C55 H55A 119.7 . . ? C56 C55 H55A 119.7 . . ? C55 C56 C51 120.3(2) . . ? C55 C56 H56A 119.9 . . ? C51 C56 H56A 119.9 . . ? C62 C61 C66 118.3(2) . . ? C62 C61 C2 119.8(2) . . ? C66 C61 C2 121.9(2) . . ? C63 C62 C61 120.7(2) . . ? C63 C62 H62A 119.6 . . ? C61 C62 H62A 119.6 . . ? C62 C63 C64 120.1(3) . . ? C62 C63 H63A 119.9 . . ? C64 C63 H63A 119.9 . . ? C65 C64 C63 119.2(3) . . ? C65 C64 H64A 120.4 . . ? C63 C64 H64A 120.4 . . ? C64 C65 C66 120.6(2) . . ? C64 C65 H65A 119.7 . . ? C66 C65 H65A 119.7 . . ? C65 C66 C61 121.0(2) . . ? C65 C66 H66A 119.5 . . ? C61 C66 H66A 119.5 . . ? H1 O1 H2 105(2) . . ? H3 O2 H4 105(2) . . ? H5 O3 H6 106(2) . . ? H7 O4 H8 104(2) . . ? H9 O5 H10 105(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 N1 C1 C11 C12 -47.8(3) . . . . ? C31 C1 C11 C12 -164.4(2) . . . . ? C21 C1 C11 C12 69.0(3) . . . . ? N1 C1 C11 C16 134.6(2) . . . . ? C31 C1 C11 C16 18.0(3) . . . . ? C21 C1 C11 C16 -108.6(2) . . . . ? C16 C11 C12 C13 -1.2(4) . . . . ? C1 C11 C12 C13 -178.8(2) . . . . ? C11 C12 C13 C14 0.1(5) . . . . ? C12 C13 C14 C15 1.1(5) . . . . ? C13 C14 C15 C16 -1.2(4) . . . . ? C12 C11 C16 C15 1.0(4) . . . . ? C1 C11 C16 C15 178.7(2) . . . . ? C14 C15 C16 C11 0.1(4) . . . . ? N1 C1 C21 C26 142.8(2) . . . . ? C31 C1 C21 C26 -99.6(2) . . . . ? C11 C1 C21 C26 26.4(3) . . . . ? N1 C1 C21 C22 -39.7(3) . . . . ? C31 C1 C21 C22 77.8(3) . . . . ? C11 C1 C21 C22 -156.2(2) . . . . ? C26 C21 C22 C23 -1.7(4) . . . . ? C1 C21 C22 C23 -179.2(2) . . . . ? C21 C22 C23 C24 0.3(4) . . . . ? C22 C23 C24 C25 1.0(4) . . . . ? C23 C24 C25 C26 -0.9(4) . . . . ? C24 C25 C26 C21 -0.5(4) . . . . ? C22 C21 C26 C25 1.8(3) . . . . ? C1 C21 C26 C25 179.3(2) . . . . ? N1 C1 C31 C32 -45.8(3) . . . . ? C21 C1 C31 C32 -163.6(2) . . . . ? C11 C1 C31 C32 70.8(3) . . . . ? N1 C1 C31 C36 137.6(2) . . . . ? C21 C1 C31 C36 19.8(3) . . . . ? C11 C1 C31 C36 -105.8(2) . . . . ? C36 C31 C32 C33 -1.6(4) . . . . ? C1 C31 C32 C33 -178.3(2) . . . . ? C31 C32 C33 C34 0.4(4) . . . . ? C32 C33 C34 C35 0.9(4) . . . . ? C33 C34 C35 C36 -0.9(4) . . . . ? C32 C31 C36 C35 1.5(3) . . . . ? C1 C31 C36 C35 178.18(19) . . . . ? C34 C35 C36 C31 -0.3(4) . . . . ? N2 C2 C41 C42 -137.1(2) . . . . ? C61 C2 C41 C42 -20.4(3) . . . . ? C51 C2 C41 C42 105.9(2) . . . . ? N2 C2 C41 C46 45.4(3) . . . . ? C61 C2 C41 C46 162.0(2) . . . . ? C51 C2 C41 C46 -71.6(3) . . . . ? C46 C41 C42 C43 -0.7(4) . . . . ? C2 C41 C42 C43 -178.3(2) . . . . ? C41 C42 C43 C44 -0.2(4) . . . . ? C42 C43 C44 C45 0.1(5) . . . . ? C43 C44 C45 C46 0.8(5) . . . . ? C44 C45 C46 C41 -1.7(5) . . . . ? C42 C41 C46 C45 1.7(4) . . . . ? C2 C41 C46 C45 179.3(2) . . . . ? N2 C2 C51 C52 -143.7(2) . . . . ? C61 C2 C51 C52 99.6(2) . . . . ? C41 C2 C51 C52 -26.8(3) . . . . ? N2 C2 C51 C56 39.5(3) . . . . ? C61 C2 C51 C56 -77.2(3) . . . . ? C41 C2 C51 C56 156.4(2) . . . . ? C56 C51 C52 C53 -0.8(4) . . . . ? C2 C51 C52 C53 -177.7(2) . . . . ? C51 C52 C53 C54 0.0(4) . . . . ? C52 C53 C54 C55 0.6(4) . . . . ? C53 C54 C55 C56 -0.3(4) . . . . ? C54 C55 C56 C51 -0.6(4) . . . . ? C52 C51 C56 C55 1.1(4) . . . . ? C2 C51 C56 C55 178.0(2) . . . . ? N2 C2 C61 C62 49.7(3) . . . . ? C41 C2 C61 C62 -67.3(3) . . . . ? C51 C2 C61 C62 166.8(2) . . . . ? N2 C2 C61 C66 -131.3(2) . . . . ? C41 C2 C61 C66 111.7(2) . . . . ? C51 C2 C61 C66 -14.2(3) . . . . ? C66 C61 C62 C63 1.3(4) . . . . ? C2 C61 C62 C63 -179.6(2) . . . . ? C61 C62 C63 C64 -0.1(4) . . . . ? C62 C63 C64 C65 -1.3(4) . . . . ? C63 C64 C65 C66 1.5(4) . . . . ? C64 C65 C66 C61 -0.3(3) . . . . ? C62 C61 C66 C65 -1.1(3) . . . . ? C2 C61 C66 C65 179.82(19) . . . . ? 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 _geom_hbond_publ_flag N1 H13 Cl1 0.97(1) 2.29(1) 3.243(2) 172(2) . ? N1 H12 Cl2 0.96(1) 2.28(2) 3.226(2) 166(2) . ? N1 H11 O2 0.96(1) 1.77(1) 2.729(2) 174(2) 1_655 ? N2 H23 Cl1 0.96(1) 2.24(1) 3.203(2) 173(2) . ? N2 H22 Cl2 0.97(1) 2.27(2) 3.219(2) 165(2) . ? N2 H21 O3 0.96(1) 1.87(1) 2.813(2) 168(2) . ? O1 H1 Cl1 0.88(1) 2.40(2) 3.266(2) 166(3) . ? O1 H2 Cl2 0.87(2) 2.47(2) 3.329(2) 172(3) 2_646 ? O2 H3 O3 0.87(1) 1.95(2) 2.798(3) 166(3) . ? O2 H4 O1 0.87(1) 1.86(2) 2.713(3) 165(3) 2_656 ? O3 H5 O4 0.86(1) 2.02(2) 2.740(3) 141(3) . ? O3 H6 O5 0.87(1) 1.87(1) 2.729(3) 175(3) . ? O4 H7 Cl1 0.88(2) 2.49(2) 3.312(2) 156(3) 1_455 ? O4 H8 Cl2 0.88(2) 2.60(2) 3.430(3) 157(3) 2_646 ? O5 H9 Cl1 0.88(1) 2.46(2) 3.310(2) 163(3) . ? O5 H10 Cl2 0.88(2) 2.35(2) 3.222(2) 176(3) 2_646 ? #===END data_THF_dimer _database_code_depnum_ccdc_archive 'CCDC 645317' _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 N +, Cl -, C4 H8 O' _chemical_formula_sum 'C23 H26 Cl N O' _chemical_formula_weight 367.90 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 9.4738(5) _cell_length_b 9.5682(5) _cell_length_c 11.7799(5) _cell_angle_alpha 76.637(2) _cell_angle_beta 71.428(2) _cell_angle_gamma 84.858(2) _cell_volume 984.65(9) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7997 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 24.93 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.823 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.839620 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay ? _diffrn_reflns_number 22314 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 25.77 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.77 _diffrn_measured_fraction_theta_full 0.982 _reflns_number_total 3712 _reflns_number_gt 3086 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v.1.0-22 (Bruker Nonius, 2004)' _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_reduction 'SAINT v.7.06a' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL v.6.10' _computing_molecular_graphics 'SHELXTL v.6.10' _computing_publication_material 'SHELXTL v.6.10' _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^)+(0.0689P)^2^+0.3660P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3712 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.443 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.052 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 Cl1 Cl 0.35239(5) 0.44594(5) 0.39688(4) 0.02811(15) Uani 1 1 d . . . N1 N 0.66255(18) 0.58698(15) 0.32923(14) 0.0214(3) Uani 1 1 d . . . H1 H 0.657(2) 0.597(2) 0.405(2) 0.032(5) Uiso 1 1 d . . . H2 H 0.572(3) 0.555(2) 0.3337(19) 0.035(6) Uiso 1 1 d . . . H3 H 0.731(2) 0.516(2) 0.3089(17) 0.024(5) Uiso 1 1 d . . . C1 C 0.70467(19) 0.72447(17) 0.23232(15) 0.0208(4) Uani 1 1 d . . . C11 C 0.60853(19) 0.84614(18) 0.28493(15) 0.0226(4) Uani 1 1 d . . . C12 C 0.4551(2) 0.8305(2) 0.33536(18) 0.0316(4) Uani 1 1 d . . . H12A H 0.4109 0.7436 0.3391 0.038 Uiso 1 1 calc R . . C13 C 0.3664(2) 0.9413(2) 0.3803(2) 0.0380(5) Uani 1 1 d . . . H13A H 0.2618 0.9295 0.4148 0.046 Uiso 1 1 calc R . . C14 C 0.4284(2) 1.0684(2) 0.37537(18) 0.0336(5) Uani 1 1 d . . . H14A H 0.3671 1.1435 0.4070 0.040 Uiso 1 1 calc R . . C15 C 0.5794(2) 1.0853(2) 0.32431(18) 0.0325(4) Uani 1 1 d . . . H15A H 0.6228 1.1730 0.3197 0.039 Uiso 1 1 calc R . . C16 C 0.6692(2) 0.97501(19) 0.27926(16) 0.0269(4) Uani 1 1 d . . . H16A H 0.7736 0.9881 0.2441 0.032 Uiso 1 1 calc R . . C21 C 0.67286(19) 0.70374(18) 0.11745(15) 0.0229(4) Uani 1 1 d . . . C22 C 0.6188(2) 0.8164(2) 0.04403(17) 0.0331(4) Uani 1 1 d . . . H22A H 0.5968 0.9066 0.0670 0.040 Uiso 1 1 calc R . . C23 C 0.5963(3) 0.7987(2) -0.06291(19) 0.0418(5) Uani 1 1 d . . . H23A H 0.5601 0.8772 -0.1125 0.050 Uiso 1 1 calc R . . C24 C 0.6260(2) 0.6691(2) -0.09729(18) 0.0391(5) Uani 1 1 d . . . H24A H 0.6094 0.6569 -0.1698 0.047 Uiso 1 1 calc R . . C25 C 0.6803(3) 0.5567(2) -0.02552(19) 0.0412(5) Uani 1 1 d . . . H25A H 0.7016 0.4666 -0.0488 0.049 Uiso 1 1 calc R . . C26 C 0.7043(2) 0.5741(2) 0.08066(17) 0.0339(5) Uani 1 1 d . . . H26A H 0.7428 0.4958 0.1288 0.041 Uiso 1 1 calc R . . C31 C 0.87177(19) 0.74710(17) 0.20613(15) 0.0215(4) Uani 1 1 d . . . C32 C 0.9359(2) 0.7169(2) 0.30044(17) 0.0308(4) Uani 1 1 d . . . H32A H 0.8757 0.6816 0.3823 0.037 Uiso 1 1 calc R . . C33 C 1.0857(2) 0.7377(2) 0.27653(19) 0.0374(5) Uani 1 1 d . . . H33A H 1.1280 0.7139 0.3418 0.045 Uiso 1 1 calc R . . C34 C 1.1750(2) 0.7925(2) 0.15892(19) 0.0356(5) Uani 1 1 d . . . H34A H 1.2782 0.8063 0.1427 0.043 Uiso 1 1 calc R . . C35 C 1.1116(2) 0.8268(2) 0.06547(18) 0.0378(5) Uani 1 1 d . . . H35A H 1.1711 0.8669 -0.0155 0.045 Uiso 1 1 calc R . . C36 C 0.9623(2) 0.8034(2) 0.08842(17) 0.0310(4) Uani 1 1 d . . . H36A H 0.9208 0.8262 0.0226 0.037 Uiso 1 1 calc R . . O1 O 0.87471(16) 0.36123(15) 0.30004(13) 0.0414(4) Uani 1 1 d . . . C2 C 0.9606(4) 0.3483(3) 0.3828(3) 0.0818(11) Uani 1 1 d . . . H2A H 0.8940 0.3533 0.4658 0.098 Uiso 1 1 calc R . . H2B H 1.0319 0.4280 0.3546 0.098 Uiso 1 1 calc R . . C3 C 1.0428(3) 0.2081(2) 0.3865(2) 0.0480(6) Uani 1 1 d . . . H3A H 1.0096 0.1455 0.4694 0.058 Uiso 1 1 calc R . . H3B H 1.1514 0.2223 0.3630 0.058 Uiso 1 1 calc R . . C4 C 1.0050(3) 0.1444(3) 0.2950(3) 0.0606(7) Uani 1 1 d . . . H4A H 0.9277 0.0706 0.3365 0.073 Uiso 1 1 calc R . . H4B H 1.0943 0.1004 0.2443 0.073 Uiso 1 1 calc R . . C5 C 0.9478(3) 0.2709(3) 0.2181(2) 0.0450(5) Uani 1 1 d . . . H5A H 1.0310 0.3215 0.1505 0.054 Uiso 1 1 calc R . . H5B H 0.8774 0.2395 0.1827 0.054 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 Cl1 0.0342(3) 0.0301(3) 0.0212(3) -0.00378(17) -0.00978(18) -0.00612(18) N1 0.0253(8) 0.0212(8) 0.0170(8) -0.0013(6) -0.0075(6) -0.0005(6) C1 0.0267(9) 0.0191(8) 0.0157(9) -0.0001(6) -0.0077(7) -0.0010(7) C11 0.0300(9) 0.0234(9) 0.0159(9) -0.0027(6) -0.0108(7) 0.0025(7) C12 0.0300(10) 0.0281(10) 0.0380(12) -0.0083(8) -0.0117(8) 0.0011(8) C13 0.0295(11) 0.0384(11) 0.0448(13) -0.0119(9) -0.0096(9) 0.0074(8) C14 0.0433(12) 0.0316(10) 0.0276(11) -0.0104(8) -0.0140(9) 0.0132(8) C15 0.0477(12) 0.0238(9) 0.0293(11) -0.0065(7) -0.0161(9) 0.0009(8) C16 0.0316(10) 0.0262(9) 0.0235(10) -0.0048(7) -0.0097(7) -0.0008(7) C21 0.0251(9) 0.0262(9) 0.0174(9) -0.0024(7) -0.0077(7) -0.0028(7) C22 0.0450(12) 0.0328(10) 0.0251(10) -0.0065(8) -0.0174(9) 0.0070(8) C23 0.0526(13) 0.0505(13) 0.0269(11) -0.0057(9) -0.0226(10) 0.0076(10) C24 0.0468(12) 0.0541(13) 0.0229(11) -0.0086(9) -0.0170(9) -0.0095(10) C25 0.0622(14) 0.0344(11) 0.0320(12) -0.0117(9) -0.0162(10) -0.0087(10) C26 0.0525(12) 0.0276(10) 0.0252(10) -0.0041(8) -0.0182(9) 0.0003(8) C31 0.0262(9) 0.0191(8) 0.0201(9) -0.0043(6) -0.0085(7) 0.0017(7) C32 0.0318(10) 0.0382(10) 0.0210(10) 0.0013(8) -0.0101(8) -0.0057(8) C33 0.0335(11) 0.0490(12) 0.0323(11) -0.0009(9) -0.0184(9) -0.0040(9) C34 0.0246(10) 0.0447(12) 0.0376(12) -0.0090(9) -0.0090(8) -0.0024(8) C35 0.0309(11) 0.0526(13) 0.0241(11) -0.0050(9) -0.0010(8) -0.0082(9) C36 0.0322(10) 0.0402(11) 0.0202(10) -0.0039(8) -0.0086(8) -0.0029(8) O1 0.0508(9) 0.0407(8) 0.0370(8) -0.0146(6) -0.0200(7) 0.0175(7) C2 0.137(3) 0.0671(18) 0.080(2) -0.0429(16) -0.084(2) 0.0579(19) C3 0.0470(13) 0.0441(13) 0.0556(15) -0.0095(11) -0.0227(11) 0.0079(10) C4 0.0625(17) 0.0503(15) 0.087(2) -0.0347(14) -0.0405(15) 0.0235(12) C5 0.0413(12) 0.0567(14) 0.0396(13) -0.0207(10) -0.0099(10) 0.0047(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.517(2) . ? N1 H1 0.91(2) . ? N1 H2 0.91(2) . ? N1 H3 0.92(2) . ? C1 C11 1.534(2) . ? C1 C21 1.535(2) . ? C1 C31 1.539(2) . ? C11 C16 1.385(2) . ? C11 C12 1.391(3) . ? C12 C13 1.388(3) . ? C12 H12A 0.950 . ? C13 C14 1.378(3) . ? C13 H13A 0.950 . ? C14 C15 1.372(3) . ? C14 H14A 0.950 . ? C15 C16 1.389(3) . ? C15 H15A 0.950 . ? C16 H16A 0.950 . ? C21 C26 1.384(3) . ? C21 C22 1.387(2) . ? C22 C23 1.392(3) . ? C22 H22A 0.950 . ? C23 C24 1.371(3) . ? C23 H23A 0.950 . ? C24 C25 1.376(3) . ? C24 H24A 0.950 . ? C25 C26 1.388(3) . ? C25 H25A 0.950 . ? C26 H26A 0.950 . ? C31 C36 1.388(2) . ? C31 C32 1.392(2) . ? C32 C33 1.380(3) . ? C32 H32A 0.950 . ? C33 C34 1.381(3) . ? C33 H33A 0.950 . ? C34 C35 1.378(3) . ? C34 H34A 0.950 . ? C35 C36 1.382(3) . ? C35 H35A 0.950 . ? C36 H36A 0.950 . ? O1 C5 1.418(2) . ? O1 C2 1.435(3) . ? C2 C3 1.488(3) . ? C2 H2A 0.990 . ? C2 H2B 0.990 . ? C3 C4 1.500(3) . ? C3 H3A 0.990 . ? C3 H3B 0.990 . ? C4 C5 1.506(3) . ? C4 H4A 0.990 . ? C4 H4B 0.990 . ? C5 H5A 0.990 . ? C5 H5B 0.990 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 H1 113.2(13) . . ? C1 N1 H2 111.1(13) . . ? H1 N1 H2 107.6(18) . . ? C1 N1 H3 109.8(12) . . ? H1 N1 H3 108.2(17) . . ? H2 N1 H3 106.7(18) . . ? N1 C1 C11 107.14(13) . . ? N1 C1 C21 107.47(13) . . ? C11 C1 C21 111.68(13) . . ? N1 C1 C31 107.38(13) . . ? C11 C1 C31 111.99(13) . . ? C21 C1 C31 110.90(13) . . ? C16 C11 C12 118.39(16) . . ? C16 C11 C1 121.85(15) . . ? C12 C11 C1 119.70(15) . . ? C13 C12 C11 120.25(17) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C14 C13 C12 120.78(18) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C15 C14 C13 119.30(17) . . ? C15 C14 H14A 120.3 . . ? C13 C14 H14A 120.3 . . ? C14 C15 C16 120.39(17) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? C11 C16 C15 120.88(17) . . ? C11 C16 H16A 119.6 . . ? C15 C16 H16A 119.6 . . ? C26 C21 C22 117.95(16) . . ? C26 C21 C1 120.95(15) . . ? C22 C21 C1 121.02(15) . . ? C21 C22 C23 120.75(18) . . ? C21 C22 H22A 119.6 . . ? C23 C22 H22A 119.6 . . ? C24 C23 C22 120.63(19) . . ? C24 C23 H23A 119.7 . . ? C22 C23 H23A 119.7 . . ? C23 C24 C25 119.16(18) . . ? C23 C24 H24A 120.4 . . ? C25 C24 H24A 120.4 . . ? C24 C25 C26 120.49(19) . . ? C24 C25 H25A 119.8 . . ? C26 C25 H25A 119.8 . . ? C21 C26 C25 121.01(18) . . ? C21 C26 H26A 119.5 . . ? C25 C26 H26A 119.5 . . ? C36 C31 C32 117.84(16) . . ? C36 C31 C1 121.10(15) . . ? C32 C31 C1 121.02(15) . . ? C33 C32 C31 120.81(17) . . ? C33 C32 H32A 119.6 . . ? C31 C32 H32A 119.6 . . ? C32 C33 C34 120.84(18) . . ? C32 C33 H33A 119.6 . . ? C34 C33 H33A 119.6 . . ? C35 C34 C33 118.75(18) . . ? C35 C34 H34A 120.6 . . ? C33 C34 H34A 120.6 . . ? C34 C35 C36 120.66(18) . . ? C34 C35 H35A 119.7 . . ? C36 C35 H35A 119.7 . . ? C35 C36 C31 121.05(17) . . ? C35 C36 H36A 119.5 . . ? C31 C36 H36A 119.5 . . ? C5 O1 C2 105.48(17) . . ? O1 C2 C3 108.7(2) . . ? O1 C2 H2A 109.9 . . ? C3 C2 H2A 109.9 . . ? O1 C2 H2B 109.9 . . ? C3 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C2 C3 C4 104.21(19) . . ? C2 C3 H3A 110.9 . . ? C4 C3 H3A 110.9 . . ? C2 C3 H3B 110.9 . . ? C4 C3 H3B 110.9 . . ? H3A C3 H3B 108.9 . . ? C3 C4 C5 103.81(19) . . ? C3 C4 H4A 111.0 . . ? C5 C4 H4A 111.0 . . ? C3 C4 H4B 111.0 . . ? C5 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? O1 C5 C4 104.98(19) . . ? O1 C5 H5A 110.8 . . ? C4 C5 H5A 110.8 . . ? O1 C5 H5B 110.8 . . ? C4 C5 H5B 110.8 . . ? H5A C5 H5B 108.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C11 C16 132.34(16) . . . . ? C21 C1 C11 C16 -110.22(17) . . . . ? C31 C1 C11 C16 14.8(2) . . . . ? N1 C1 C11 C12 -50.4(2) . . . . ? C21 C1 C11 C12 67.0(2) . . . . ? C31 C1 C11 C12 -167.93(15) . . . . ? C16 C11 C12 C13 -1.0(3) . . . . ? C1 C11 C12 C13 -178.28(17) . . . . ? C11 C12 C13 C14 0.2(3) . . . . ? C12 C13 C14 C15 0.6(3) . . . . ? C13 C14 C15 C16 -0.7(3) . . . . ? C12 C11 C16 C15 0.9(3) . . . . ? C1 C11 C16 C15 178.11(16) . . . . ? C14 C15 C16 C11 0.0(3) . . . . ? N1 C1 C21 C26 -39.8(2) . . . . ? C11 C1 C21 C26 -157.05(17) . . . . ? C31 C1 C21 C26 77.3(2) . . . . ? N1 C1 C21 C22 143.43(17) . . . . ? C11 C1 C21 C22 26.2(2) . . . . ? C31 C1 C21 C22 -99.48(19) . . . . ? C26 C21 C22 C23 0.3(3) . . . . ? C1 C21 C22 C23 177.15(18) . . . . ? C21 C22 C23 C24 0.6(3) . . . . ? C22 C23 C24 C25 -0.8(3) . . . . ? C23 C24 C25 C26 0.2(3) . . . . ? C22 C21 C26 C25 -0.9(3) . . . . ? C1 C21 C26 C25 -177.77(18) . . . . ? C24 C25 C26 C21 0.7(3) . . . . ? N1 C1 C31 C36 143.11(16) . . . . ? C11 C1 C31 C36 -99.54(18) . . . . ? C21 C1 C31 C36 26.0(2) . . . . ? N1 C1 C31 C32 -39.4(2) . . . . ? C11 C1 C31 C32 78.00(19) . . . . ? C21 C1 C31 C32 -156.51(16) . . . . ? C36 C31 C32 C33 -2.2(3) . . . . ? C1 C31 C32 C33 -179.86(17) . . . . ? C31 C32 C33 C34 1.7(3) . . . . ? C32 C33 C34 C35 0.2(3) . . . . ? C33 C34 C35 C36 -1.6(3) . . . . ? C34 C35 C36 C31 1.0(3) . . . . ? C32 C31 C36 C35 0.9(3) . . . . ? C1 C31 C36 C35 178.49(17) . . . . ? C5 O1 C2 C3 -24.4(3) . . . . ? O1 C2 C3 C4 3.0(3) . . . . ? C2 C3 C4 C5 18.1(3) . . . . ? C2 O1 C5 C4 35.7(3) . . . . ? C3 C4 C5 O1 -33.5(3) . . . . ?