# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/231 #Paper ref: 9/04998C #Structural Studies of the Two Protonated Forms of a C2 Symmetrical #Optically Active Cyclam Derivative data_na272 #(3H4 4+Br4 4-) _audit_creation_method SHELXL _chemical_name_systematic ; 2,6,9,13-tetraazabicyclo[12.4.0]octadecane-2,6,9,13-tetraium tetrabromide ; _chemical_name_common ? _chemical_formula_moiety 'C14 H34 N4, Br4, H2 O' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H36 Br4 N4 O' _chemical_formula_weight 596.11 _chemical_melting_point ? _chemical_compound_source 'synthesis' 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.990(10) _cell_length_b 15.168(2) _cell_length_c 9.7127(13) _cell_angle_alpha 90.00 _cell_angle_beta 106.69(6) _cell_angle_gamma 90.00 _cell_volume 1127.5(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13 _cell_measurement_theta_max 15 _exptl_crystal_description 'prismatic' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.756 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 7.147 _exptl_absorpt_correction_type 'XABS2. (Parkin et al, 1995)' _exptl_absorpt_correction_T_min 0.1693 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; Nonius CAD4 single crystal diffractometer. ; _diffrn_ambient_temperature 293(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 'Nonius CAD4 diffractometer' _diffrn_measurement_method \w-2\Q _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 4.66 _diffrn_reflns_number 2378 _diffrn_reflns_av_R_equivalents 0.0791 _diffrn_reflns_av_sigmaI/netI 0.1261 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2233 _reflns_number_observed 1263 _reflns_observed_criterion >2sigma(I) _computing_data_collection ; Nonius CAD4 Diffractometer Control Software. Data Collection with profile analysis over all reflections (Lehman and Larsen, 1974; Grant and Gable, 1978) ; _computing_cell_refinement 'CRYSDA (Beurskens et al, 1992)' _computing_data_reduction 'THE REFLEX (local program)' _computing_structure_solution ; Patterson methods and phase using DIRDIF (Beurskens, 1992) ; _computing_structure_refinement ; Anisotropic least-squares refinement carried out with SHELXL-93 (Sheldrick, 1993). Geometrical calculations made with PARST (Nardelli, 1983) ; _computing_molecular_graphics 'EUCLID (Spek, 1982)' _computing_publication_material ; SHELXL-93 (Sheldrick, 1993). All calculations made at the University of Oviedo on the Scientific Computer Center and X-Ray group VAX/AXP computers. ; _refine_special_details ; Refinement on F^2^ for ALL reflections except for 10 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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. Some of the H atoms coordinates were calculated with the Difference Fourier Synthesis and the rest were refined riding from the ideal geometry using common thermal parameters. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0274P)^2^+10.0862P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary Patterson _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difference map and geometric' _refine_ls_hydrogen_treatment 'riding U isotropic commons' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2233 _refine_ls_number_parameters 253 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1450 _refine_ls_R_factor_obs 0.0467 _refine_ls_wR_factor_all 0.1320 _refine_ls_wR_factor_obs 0.0971 _refine_ls_goodness_of_fit_all 1.037 _refine_ls_goodness_of_fit_obs 1.065 _refine_ls_restrained_S_all 1.103 _refine_ls_restrained_S_obs 1.186 _refine_ls_shift/esd_max -0.754 _refine_ls_shift/esd_mean 0.024 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br1 Br -0.1293(3) -0.49233(12) -0.0358(2) 0.0367(5) Uani 1 d . . Br2 Br 0.4730(3) 0.4924(2) 0.4594(2) 0.0522(7) Uani 1 d . . Br3 Br -0.2624(3) 0.2316(2) 0.2232(2) 0.0559(7) Uani 1 d . . Br4 Br 0.3788(3) 0.2339(2) 0.7905(2) 0.0525(6) Uani 1 d . . N1 N 0.2503(16) -0.4716(10) -0.3132(15) 0.031(4) Uani 1 d G . H11 H 0.2822(33) -0.4029(12) -0.3018(79) 0.041(19) Uiso 1 d G . H12 H 0.2871(66) -0.5036(45) -0.3984(71) 0.041(19) Uiso 1 d G . N2 N -0.1642(16) -0.5940(9) -0.3433(16) 0.030(4) Uani 1 d GD . H21 H -0.2178(37) -0.5694(42) -0.4290(43) 0.041(19) Uiso 1 d GD . H22 H -0.1814(56) -0.5579(36) -0.2751(63) 0.041(19) Uiso 1 d GD . N3 N 0.0960(17) -0.7814(9) -0.0260(16) 0.036(4) Uani 1 d G . H31 H 0.1833(66) -0.7916(41) -0.0898(66) 0.041(19) Uiso 1 d G . H32 H 0.1282(36) -0.8490(12) 0.0008(81) 0.041(19) Uiso 1 d G . N4 N 0.4068(15) -0.6440(9) 0.0776(14) 0.031(4) Uani 1 d GD . H41 H 0.5046(33) -0.6701(15) 0.1321(68) 0.041(19) Uiso 1 d GD . H42 H 0.3732(56) -0.6732(33) -0.0066(29) 0.041(19) Uiso 1 d GD . C1 C 0.058(2) -0.4852(19) -0.343(2) 0.040(6) Uani 1 d . . H1 H 0.0244(22) -0.4653(19) -0.2589(21) 0.042(13) Uiso 1 calc R . C2 C -0.038(2) -0.4291(14) -0.4697(19) 0.035(5) Uani 1 d G . H2A H -0.1598(26) -0.4247(14) -0.4714(19) 0.050(21) Uiso 1 calc R . H2B H 0.0109(26) -0.3701(14) -0.4573(19) 0.050(21) Uiso 1 calc R . C3 C -0.028(2) -0.4657(12) -0.612(2) 0.025(5) Uani 1 d G . H3A H -0.1015(25) -0.4304(12) -0.6890(20) 0.050(21) Uiso 1 calc R . H3B H 0.0913(25) -0.4605(12) -0.6164(20) 0.050(21) Uiso 1 calc R . C4 C -0.084(2) -0.5603(12) -0.635(2) 0.030(5) Uani 1 d G . H4A H -0.0687(27) -0.5810(12) -0.7251(21) 0.050(21) Uiso 1 calc R . H4B H -0.2065(27) -0.5654(12) -0.6402(21) 0.050(21) Uiso 1 calc R . C5 C 0.028(2) -0.6179(12) -0.5086(17) 0.030(5) Uani 1 d G . H5A H -0.0119(25) -0.6786(12) -0.5216(17) 0.050(21) Uiso 1 calc R . H5B H 0.1494(25) -0.6164(12) -0.5081(17) 0.050(21) Uiso 1 calc R . C6 C 0.01(2) -0.5830(14) -0.366(2) 0.031(5) Uani 1 d . . H6 H 0.0946(25) -0.6158(14) -0.2901(21) 0.042(13) Uiso 1 calc R . C7 C -0.240(2) -0.6859(13) -0.355(2) 0.043(6) Uani 1 d G . H7A H -0.2714(28) -0.7042(13) -0.4546(24) 0.042(13) Uiso 1 calc R . H7B H -0.3463(28) -0.6843(13) -0.3255(24) 0.042(13) Uiso 1 calc R . C8 C -0.117(2) -0.7542(15) -0.264(2) 0.042(6) Uani 1 d G . H8A H -0.1744(26) -0.8111(15) -0.2771(20) 0.042(13) Uiso 1 calc R . H8B H -0.0138(26) -0.7589(15) -0.2975(20) 0.042(13) Uiso 1 calc R . C9 C -0.061(2) -0.7313(14) -0.105(2) 0.041(5) Uani 1 d G . H9A H -0.0363(26) -0.6687(14) -0.0941(21) 0.042(13) Uiso 1 calc R . H9B H -0.1559(26) -0.7442(14) -0.0649(21) 0.042(13) Uiso 1 calc R . C10 C 0.187(2) -0.7512(13) 0.121(2) 0.041(6) Uani 1 d G . H10A H 0.2846(28) -0.7904(13) 0.1613(22) 0.042(13) Uiso 1 calc R . H10B H 0.1070(28) -0.7573(13) 0.1795(22) 0.042(13) Uiso 1 calc R . C11 C 0.256(2) -0.6566(13) 0.137(2) 0.033(5) Uani 1 d G . H11A H 0.1621(25) -0.6172(13) 0.0874(20) 0.042(13) Uiso 1 calc R . H11B H 0.2911(25) -0.6407(13) 0.2378(20) 0.042(13) Uiso 1 calc R . C12 C 0.465(2) -0.5517(13) 0.070(2) 0.034(5) Uani 1 d G . H12A H 0.5818(26) -0.5527(13) 0.0590(21) 0.042(13) Uiso 1 calc R . H12B H 0.4722(26) -0.5231(13) 0.1609(21) 0.042(13) Uiso 1 calc R . C13 C 0.351(2) -0.4964(15) -0.0492(15) 0.029(4) Uani 1 d G . H13A H 0.3771(21) -0.4345(15) -0.0284(15) 0.042(13) Uiso 1 calc R . H13B H 0.2291(21) -0.5058(15) -0.0538(15) 0.042(13) Uiso 1 calc R . C14 C 0.378(2) -0.5189(13) -0.1925(19) 0.034(5) Uani 1 d G . H14A H 0.4959(25) -0.5031(13) -0.1914(19) 0.042(13) Uiso 1 calc R . H14B H 0.3645(25) -0.5820(13) -0.2082(19) 0.042(13) Uiso 1 calc R . O1W O 0.388(3) 0.212(3) 0.443(2) 0.179(13) Uani 1 d D . H1W H 0.4165(477) 0.1826(419) 0.5481(73) 0.268 Uiso 1 d D . H2W H 0.4980(322) 0.2254(446) 0.4273(370) 0.268 Uiso 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 Br1 0.0426(13) 0.0305(11) 0.0372(11) -0.0046(11) 0.0121(9) -0.0009(12) Br2 0.0362(13) 0.082(2) 0.0380(12) 0.002(2) 0.0098(11) 0.0069(15) Br3 0.057(2) 0.0319(12) 0.062(2) 0.0044(15) -0.0092(12) 0.0052(14) Br4 0.0607(15) 0.0489(14) 0.0544(15) -0.0084(15) 0.0268(12) 0.0008(15) N1 0.043(10) 0.027(10) 0.029(8) -0.002(8) 0.017(8) -0.012(8) N2 0.039(10) 0.028(9) 0.028(9) -0.004(8) 0.015(8) -0.002(8) N3 0.052(11) 0.017(10) 0.039(10) 0.013(8) 0.013(8) 0.006(8) N4 0.024(9) 0.037(10) 0.026(8) 0.001(8) -0.002(7) 0.012(8) C1 0.014(9) 0.063(17) 0.040(12) -0.010(14) 0.002(9) -0.003(13) C2 0.035(12) 0.030(12) 0.031(12) -0.012(10) -0.003(10) -0.003(10) C3 0.030(12) 0.017(11) 0.026(11) 0.011(8) 0.003(9) 0.006(8) C4 0.034(13) 0.017(11) 0.034(12) -0.006(10) 0.000(10) -0.009(9) C5 0.045(12) 0.014(10) 0.032(12) -0.002(9) 0.015(10) 0.003(9) C6 0.030(12) 0.025(12) 0.031(12) 0.006(10) 0.001(9) 0.003(10) C7 0.046(15) 0.022(12) 0.062(15) 0.000(11) 0.017(12) 0.001(11) C8 0.056(14) 0.031(15) 0.036(12) -0.001(11) 0.009(11) 0.007(12) C9 0.047(13) 0.038(13) 0.043(13) 0.009(11) 0.023(11) 0.018(11) C10 0.058(15) 0.026(15) 0.039(13) 0.013(10) 0.016(11) 0.013(11) C11 0.042(12) 0.031(12) 0.030(11) 0.003(10) 0.016(9) -0.001(10) C12 0.027(12) 0.036(13) 0.029(11) 0.005(10) -0.011(9) 0.002(10) C13 0.027(10) 0.035(11) 0.022(9) -0.003(11) 0.003(8) 0.002(12) C14 0.036(14) 0.030(12) 0.035(12) 0.002(10) 0.010(11) 0.004(10) O1W 0.169(26) 0.232(37) 0.115(22) 0.022(29) 0.009(19) -0.046(30) _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 1.49(2) . YES N1 C14 1.50(2) . YES N1 H11 1.07 . YES N1 H12 1.07 . YES N2 C6 1.49(2) . YES N2 C7 1.51(2) . YES N2 H21 0.90 . YES N2 H22 0.90 . YES N3 C9 1.48(2) . YES N3 C10 1.48(2) . YES N3 H31 1.07 . YES N3 H32 1.07 . YES N4 C12 1.49(2) . YES N4 C11 1.49(2) . YES N4 H41 0.90 . YES N4 H42 0.90 . YES C1 C2 1.51(3) . YES C1 C6 1.53(3) . YES C1 H1 0.98 . YES C2 C3 1.51(2) . YES C2 H2A 0.97 . YES C2 H2B 0.97 . YES C3 C4 1.50(2) . YES C3 H3A 0.97 . YES C3 H3B 0.97 . YES C4 C5 1.56(3) . YES C4 H4A 0.97 . YES C4 H4B 0.97 . YES C5 C6 1.52(2) . YES C5 H5A 0.97 . YES C5 H5B 0.97 . YES C6 H6 0.98 . YES C7 C8 1.52(3) . YES C7 H7A 0.97 . YES C7 H7B 0.97 . YES C8 C9 1.51(3) . YES C8 H8A 0.97 . YES C8 H8B 0.97 . YES C9 H9A 0.97 . YES C9 H9B 0.97 . YES C10 C11 1.53(3) . YES C10 H10A 0.97 . YES C10 H10B 0.97 . YES C11 H11A 0.97 . YES C11 H11B 0.97 . YES C12 C13 1.50(2) . YES C12 H12A 0.97 . YES C12 H12B 0.97 . YES C13 C14 1.51(2) . YES C13 H13A 0.97 . YES C13 H13B 0.97 . YES C14 H14A 0.97 . YES C14 H14B 0.97 . YES O1W H1W 1.5(4) . YES O1W H2W 0.97(11) . YES 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 C14 121.2(16) . . YES C1 N1 H11 110.8(13) . . YES C14 N1 H11 107.(3) . . YES C1 N1 H12 106.(2) . . YES C14 N1 H12 95.(5) . . YES H11 N1 H12 114.2 . . YES C6 N2 C7 117.7(15) . . YES C6 N2 H21 91.(2) . . YES C7 N2 H21 103.(3) . . YES C6 N2 H22 113.3(12) . . YES C7 N2 H22 118.(2) . . YES H21 N2 H22 107.2 . . YES C9 N3 C10 117.0(16) . . YES C9 N3 H31 111.(5) . . YES C10 N3 H31 112.(2) . . YES C9 N3 H32 136.6(12) . . YES C10 N3 H32 92.(3) . . YES H31 N3 H32 81.4 . . YES C12 N4 C11 116.0(15) . . YES C12 N4 H41 102.4(11) . . YES C11 N4 H41 112.(4) . . YES C12 N4 H42 115.(2) . . YES C11 N4 H42 103.0(14) . . YES H41 N4 H42 107.4 . . YES N1 C1 C2 109.6(18) . . YES N1 C1 C6 111.0(18) . . YES C2 C1 C6 112.2(17) . . YES N1 C1 H1 107.9(10) . . YES C2 C1 H1 108.0(12) . . YES C6 C1 H1 108.0(11) . . YES C1 C2 C3 112.8(18) . . YES C1 C2 H2A 109.0(12) . . YES C3 C2 H2A 109.1(10) . . YES C1 C2 H2B 109.0(11) . . YES C3 C2 H2B 109.0(10) . . YES H2A C2 H2B 107.8 . . YES C4 C3 C2 113.3(17) . . YES C4 C3 H3A 109.0(11) . . YES C2 C3 H3A 108.9(10) . . YES C4 C3 H3B 108.9(11) . . YES C2 C3 H3B 108.9(10) . . YES H3A C3 H3B 107.7 . . YES C3 C4 C5 109.9(16) . . YES C3 C4 H4A 109.6(12) . . YES C5 C4 H4A 109.6(10) . . YES C3 C4 H4B 109.7(11) . . YES C5 C4 H4B 109.8(10) . . YES H4A C4 H4B 108.2 . . YES C6 C5 C4 109.8(16) . . YES C6 C5 H5A 109.7(11) . . YES C4 C5 H5A 109.7(10) . . YES C6 C5 H5B 109.8(10) . . YES C4 C5 H5B 109.8(10) . . YES H5A C5 H5B 108.2 . . YES N2 C6 C5 115.6(16) . . YES N2 C6 C1 106.7(15) . . YES C5 C6 C1 113.0(17) . . YES N2 C6 H6 107.1(10) . . YES C5 C6 H6 107.0(10) . . YES C1 C6 H6 107.0(11) . . YES N2 C7 C8 113.9(17) . . YES N2 C7 H7A 108.7(11) . . YES C8 C7 H7A 108.8(11) . . YES N2 C7 H7B 108.8(10) . . YES C8 C7 H7B 108.8(12) . . YES H7A C7 H7B 107.7 . . YES C9 C8 C7 112.8(18) . . YES C9 C8 H8A 109.1(12) . . YES C7 C8 H8A 109.0(11) . . YES C9 C8 H8B 109.0(11) . . YES C7 C8 H8B 109.1(12) . . YES H8A C8 H8B 107.8 . . YES N3 C9 C8 112.0(16) . . YES N3 C9 H9A 109.2(10) . . YES C8 C9 H9A 109.2(12) . . YES N3 C9 H9B 109.2(9) . . YES C8 C9 H9B 109.2(11) . . YES H9A C9 H9B 107.9 . . YES N3 C10 C11 116.8(16) . . YES N3 C10 H10A 108.1(10) . . YES C11 C10 H10A 108.1(11) . . YES N3 C10 H10B 108.1(10) . . YES C11 C10 H10B 108.0(11) . . YES H10A C10 H10B 107.3 . . YES N4 C11 C10 112.9(16) . . YES N4 C11 H11A 109.0(10) . . YES C10 C11 H11A 108.9(11) . . YES N4 C11 H11B 109.0(9) . . YES C10 C11 H11B 109.1(11) . . YES H11A C11 H11B 107.8 . . YES N4 C12 C13 115.8(16) . . YES N4 C12 H12A 108.3(10) . . YES C13 C12 H12A 108.4(10) . . YES N4 C12 H12B 108.4(10) . . YES C13 C12 H12B 108.3(11) . . YES H12A C12 H12B 107.4 . . YES C12 C13 C14 111.5(17) . . YES C12 C13 H13A 109.4(11) . . YES C14 C13 H13A 109.4(12) . . YES C12 C13 H13B 109.4(10) . . YES C14 C13 H13B 109.3(10) . . YES H13A C13 H13B 108.0 . . YES N1 C14 C13 111.5(15) . . YES N1 C14 H14A 109.3(9) . . YES C13 C14 H14A 109.3(10) . . YES N1 C14 H14B 109.3(10) . . YES C13 C14 H14B 109.3(12) . . YES H14A C14 H14B 108.0 . . YES H1W O1W H2W 108.(10) . . YES 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 C14 N1 C1 C2 179.8(17) . . . . YES C14 N1 C1 C6 -56.(2) . . . . YES N1 C1 C2 C3 75.(2) . . . . YES C6 C1 C2 C3 -48.(2) . . . . YES C1 C2 C3 C4 52.(2) . . . . YES C2 C3 C4 C5 -56.(2) . . . . YES C3 C4 C5 C6 57.(2) . . . . YES C7 N2 C6 C5 56.(2) . . . . YES C7 N2 C6 C1 -177.8(16) . . . . YES C4 C5 C6 N2 68.(2) . . . . YES C4 C5 C6 C1 -55.(2) . . . . YES N1 C1 C6 N2 160.1(15) . . . . YES C2 C1 C6 N2 -77.(2) . . . . YES N1 C1 C6 C5 -72.(2) . . . . YES C2 C1 C6 C5 51.(2) . . . . YES C6 N2 C7 C8 51.(2) . . . . YES N2 C7 C8 C9 59.(2) . . . . YES C10 N3 C9 C8 166.6(17) . . . . YES C7 C8 C9 N3 -162.8(17) . . . . YES C9 N3 C10 C11 -59.(2) . . . . YES C12 N4 C11 C10 171.6(16) . . . . YES N3 C10 C11 N4 -70.(2) . . . . YES C11 N4 C12 C13 -75.(2) . . . . YES N4 C12 C13 C14 -76.(2) . . . . YES C1 N1 C14 C13 -61.(2) . . . . YES C12 C13 C14 N1 173.5(15) . . . . YES loop_ _publ_manuscript_incl_extra_item '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm # - - - --- ----- ----- ------- ---- N2 H22 Br1 0.90(6) 2.45(6) 3.30(1) 156.6(5) 1_555 N4 H42 N3 0.90(3) 2.72(5) 3.17(2) 112.6(3) 1_555 C1 H1 Br1 0.98(3) 2.81(2) 3.70(2) 152.2(2) 1_555 C2 H2A N2 0.97(3) 2.86(2) 3.08(2) 93.9(2) 1_555 C3 H3B N1 0.97(3) 2.86(2) 3.11(2) 95.7(1) 1_555 C4 H4B N2 0.97(3) 2.84(2) 3.12(3) 97.7(2) 1_555 C5 H5B N1 0.97(3) 2.86(2) 3.12(2) 96.4(2) 1_555 C9 H9A Br1 0.97(3) 2.88(2) 3.75(2) 151.4(2) 1_555 C9 H9A N2 0.97(3) 2.60(2) 3.04(2) 107.9(2) 1_555 C11 H11A Br1 0.97(3) 2.97(2) 3.94(2) 174.4(2) 1_555 C13 H13B Br1 0.97(2) 2.82(2) 3.87(2) 166.1(2) 1_555 C14 H14B N4 0.97(2) 2.85(2) 3.20(2) 101.2(2) 1_555 O1W H1W Br4 1.10(3) 2.58(2) 3.41(3) 133.7(5) 1_555 N1 H11 Br3 1.08(2) 2.20(3) 3.20(1) 154.1(2) 2_565 N3 H32 Br1 1.08(2) 2.20(2) 3.25(1) 166.8(2) 2_565 N4 H42 Br4 0.90(3) 2.43(4) 3.30(1) 161.8(2) 1_544 N1 H12 Br2 1.07(6) 2.30(6) 3.25(2) 147.5(5) 1_544 C14 H14B Br4 0.97(2) 2.80(2) 3.75(2) 169.5(2) 1_544 N3 H31 Br4 1.70(6) 2.23(2) 3.26(2) 161.3(5) 1_544 N2 H21 Br2 0.90(4) 2.57(3) 3.25(1) 133.2(3) 1_444 N4 H41 Br3 0.90(3) 2.35(2) 3.22(1) 163.9(2) 1_645 C10 H10A O1W 0.97(2) 2.62(3) 3.12(3) 112.5(2) 1_545 _refine_diff_density_max 0.779 _refine_diff_density_min -1.077 _refine_diff_density_rms 0.186 #===END data_na294 #(3H2 2+(ClO4)2 2-) _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6,9,13-tetraazabicyclo[12.4.0]octadecane-2,9-diium diperchlorate ; _chemical_name_common ? _chemical_formula_moiety 'C14 H32 N4, (Cl O4)2' _chemical_formula_sum 'C14 H32 Cl2 N4 O8' _chemical_formula_weight 455.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.033(6) _cell_length_b 8.268(7) _cell_length_c 18.029(17) _cell_angle_alpha 100.01(6) _cell_angle_beta 94.67(5) _cell_angle_gamma 116.89(7) _cell_volume 1034.2(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7 _cell_measurement_theta_max 15 _exptl_crystal_description 'prismatic' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.363 _exptl_absorpt_correction_type 'XABS2 (Parkin et al,1995)' _exptl_absorpt_correction_T_min 0.575 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; Nonius CAD4 single crystal diffractometer ; _diffrn_ambient_temperature 293(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 'Enraf-Nonius CAD4' _diffrn_measurement_method \w-2\Q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 7.12 _diffrn_reflns_number 3765 _diffrn_reflns_av_R_equivalents 0.0812 _diffrn_reflns_av_sigmaI/netI 0.2183 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3639 _reflns_number_gt 1619 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Nonius CAD4 Diffractometer Control Software. Data Collection with profile analysis over all reflections. (Lehman and Larsen, 1974, Grant and Gable, 1978) ; _computing_cell_refinement 'CRYSDA (Beurskens et al, 1992)' _computing_data_reduction 'THE REFLEX (local program)' _computing_structure_solution ; Direct methods using the SHELXS-86 (Sheldrick, 1990) ; _computing_structure_refinement ; Anisotropic least-squares refinement carried out with SHELXL-93(Sheldrick, 1993). Geometricla calculations made with PARST (Nardelli, 1983). ; _computing_molecular_graphics 'EUCLID (Spek, 1982)' _computing_publication_material ; SHELXL-93 (Sheldrick, 1993). All calculations made at the University of Oviedo on the Scientific Computer Center and X-Ray group VAX/AXP computers. ; _refine_special_details ; Refinement of F^2^ against ALL reflections except for 34 with very negative F^2^ or flagged by the user for potential systematic errors. 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. Hydrogen atoms attached to all carbon atoms were found by difference Fourier synthesis, but due to their unstability they were refined riding from the ideal geometry using common thermal parameters. Most of H-atoms bonded to nitrogens were also located by difference Fourier synthesis. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difference map and geometrical' _refine_ls_hydrogen_treatment 'riding U isotropic commons' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3639 _refine_ls_number_parameters 533 _refine_ls_number_restraints 34 _refine_ls_R_factor_all 0.2101 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1653 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.8002(5) 0.4624(5) 0.2518(2) 0.0433(11) Uani 1 d . . . O11 O 0.934(2) 0.6514(19) 0.2661(10) 0.141(7) Uani 1 d . . . O12 O 0.6912(16) 0.4392(15) 0.3118(6) 0.061(3) Uani 1 d . . . O13 O 0.6808(16) 0.4078(17) 0.1805(6) 0.073(4) Uani 1 d . . . O14 O 0.8944(17) 0.3548(18) 0.2525(8) 0.090(4) Uani 1 d . . . Cl2 Cl 0.1700(4) 0.6377(4) 0.4807(2) 0.0346(10) Uani 1 d . . . O21 O 0.0600(17) 0.4441(15) 0.4726(9) 0.093(5) Uani 1 d . . . O22 O 0.3023(14) 0.6724(13) 0.4299(6) 0.050(3) Uani 1 d . . . O23 O 0.2808(19) 0.7254(17) 0.5567(6) 0.081(4) Uani 1 d . . . O24 O 0.0526(14) 0.7218(14) 0.4658(7) 0.068(4) Uani 1 d . . . Cl3 Cl 0.1732(5) 0.8628(5) 0.0543(2) 0.0475(11) Uani 1 d . . . O31 O 0.2651(17) 0.8290(18) -0.0029(7) 0.082(4) Uani 1 d . . . O32 O 0.2613(18) 0.8730(19) 0.1269(7) 0.077(4) Uani 1 d . . . O33 O -0.0154(19) 0.720(3) 0.0350(10) 0.159(8) Uani 1 d . . . O34 O 0.167(3) 1.022(2) 0.0572(9) 0.180(10) Uani 1 d . . . Cl4 Cl -0.1192(4) 0.8066(4) -0.1706(2) 0.0307(9) Uani 1 d . . . O41 O -0.1794(16) 0.6178(13) -0.1677(7) 0.064(3) Uani 1 d . . . O42 O -0.1968(13) 0.8862(15) -0.1144(5) 0.052(3) Uani 1 d . . . O43 O 0.0821(14) 0.9124(13) -0.1509(7) 0.062(3) Uani 1 d . . . O44 O -0.1844(15) 0.8170(14) -0.2435(6) 0.058(3) Uani 1 d . . . N1 N -0.3217(15) 0.6547(16) -0.5297(7) 0.027(3) Uani 1 d D . . H1N1 H -0.251(14) 0.615(15) -0.552(6) 0.036(12) Uiso 1 d D . . H2N1 H -0.401(14) 0.635(17) -0.571(4) 0.036(12) Uiso 1 d D . . N2 N -0.6466(13) 0.3049(13) -0.5986(6) 0.023(3) Uani 1 d D . . H1N2 H -0.740(9) 0.299(12) -0.577(5) 0.001(13) Uiso 1 d D . . N3 N -0.3859(17) 0.7974(15) -0.6604(7) 0.035(3) Uani 1 d D . . H1N3 H -0.328(11) 0.734(10) -0.673(5) 0.001(13) Uiso 1 d D . . N4 N -0.7183(16) 0.4409(16) -0.7267(7) 0.029(3) Uani 1 d D . . H1N4 H -0.643(14) 0.482(16) -0.682(4) 0.036(12) Uiso 1 d D . . H2N4 H -0.819(11) 0.429(16) -0.709(7) 0.036(12) Uiso 1 d D . . C1 C -0.4198(18) 0.5201(16) -0.4822(7) 0.025(3) Uani 1 d . . . H1 H -0.5184 0.5454 -0.4630 0.033(17) Uiso 1 calc R . . C2 C -0.2780(16) 0.5437(17) -0.4145(7) 0.033(3) Uani 1 d . . . H2A H -0.1746 0.5283 -0.4328 0.044(5) Uiso 1 calc R . . H2B H -0.2253 0.6683 -0.3819 0.044(5) Uiso 1 calc R . . C3 C -0.3755(18) 0.3998(17) -0.3687(8) 0.041(4) Uani 1 d . . . H3A H -0.2821 0.4122 -0.3274 0.044(5) Uiso 1 calc R . . H3B H -0.4693 0.4250 -0.3460 0.044(5) Uiso 1 calc R . . C4 C -0.470(2) 0.2055(17) -0.4161(8) 0.046(4) Uani 1 d . . . H4A H -0.5390 0.1205 -0.3853 0.044(5) Uiso 1 calc R . . H4B H -0.3752 0.1735 -0.4332 0.044(5) Uiso 1 calc R . . C5 C -0.6061(18) 0.1834(17) -0.4847(7) 0.035(3) Uani 1 d . . . H5A H -0.7105 0.1984 -0.4671 0.044(5) Uiso 1 calc R . . H5B H -0.6584 0.0579 -0.5164 0.044(5) Uiso 1 calc R . . C6 C -0.5127(18) 0.3254(18) -0.5341(7) 0.027(3) Uani 1 d . . . H6 H -0.4130 0.3036 -0.5541 0.033(17) Uiso 1 calc R . . C7 C -0.7207(18) 0.1302(16) -0.6570(8) 0.028(3) Uani 1 d . . . H7A H -0.7817 0.0266 -0.6333 0.044(5) Uiso 1 calc R . . H7B H -0.6153 0.1219 -0.6766 0.044(5) Uiso 1 calc R . . C8 C -0.8598(19) 0.1112(19) -0.7227(8) 0.032(4) Uiso 1 d . . . H8A H -0.9622 0.1250 -0.7026 0.044(5) Uiso 1 calc R . . H8B H -0.9140 -0.0141 -0.7549 0.044(5) Uiso 1 calc R . . C9 C -0.781(2) 0.2472(17) -0.7717(8) 0.040(4) Uani 1 d . . . H9A H -0.6740 0.2399 -0.7903 0.044(5) Uiso 1 calc R . . H9B H -0.8772 0.2160 -0.8157 0.044(5) Uiso 1 calc R . . C10 C -0.629(2) 0.5883(18) -0.7717(9) 0.036(4) Uani 1 d U . . H10A H -0.5343 0.5699 -0.7963 0.044(5) Uiso 1 calc R . . H10B H -0.7262 0.5767 -0.8113 0.044(5) Uiso 1 calc R . . C11 C -0.540(2) 0.778(2) -0.7195(9) 0.040(4) Uani 1 d U . . H11A H -0.6348 0.7967 -0.6947 0.044(5) Uiso 1 calc R . . H11B H -0.4874 0.8721 -0.7487 0.044(5) Uiso 1 calc R . . C12 C -0.300(2) 0.980(2) -0.6040(8) 0.042(4) Uani 1 d . . . H12A H -0.3978 0.9968 -0.5811 0.044(5) Uiso 1 calc R . . H12B H -0.2388 1.0803 -0.6297 0.044(5) Uiso 1 calc R . . C13 C -0.155(2) 0.9882(19) -0.5424(9) 0.037(4) Uani 1 d . . . H13A H -0.0653 0.9590 -0.5668 0.044(5) Uiso 1 calc R . . H13B H -0.0847 1.1150 -0.5113 0.044(5) Uiso 1 calc R . . C14 C -0.2358(18) 0.8583(17) -0.4903(8) 0.030(4) Uani 1 d . . . H14A H -0.1357 0.8873 -0.4482 0.044(5) Uiso 1 calc R . . H14B H -0.3324 0.8806 -0.4687 0.044(5) Uiso 1 calc R . . N5 N 0.3977(15) 0.8422(15) -0.1652(7) 0.035(3) Uani 1 d GD . . H1N5 H 0.2778 0.7989 -0.1627 0.036(12) Uiso 1 d GD . . H2N5 H 0.4737 0.8492 -0.1264 0.036(12) Uiso 1 d GD . . N6 N 0.4037(15) 0.5620(13) -0.0948(6) 0.024(3) Uani 1 d D . . H1N6 H 0.507(8) 0.559(12) -0.100(5) 0.001(13) Uiso 1 d D . . N7 N 0.6570(16) 1.1290(16) -0.0350(7) 0.035(3) Uani 1 d . . . H1N7 H 0.601(13) 1.159(10) -0.005(4) 0.001(13) Uiso 1 d D . . N8 N 0.6824(16) 0.8463(16) 0.0353(7) 0.032(3) Uani 1 d D . . H1N8 H 0.773(12) 0.837(16) 0.016(7) 0.036(12) Uiso 1 d D . . H2N8 H 0.590(12) 0.802(16) -0.003(5) 0.036(12) Uiso 1 d D . . C15 C 0.3225(18) 0.6441(15) -0.2143(7) 0.023(3) Uani 1 d D . . H15 H 0.4288 0.6344 -0.2339 0.033(17) Uiso 1 calc RD . . C16 C 0.1749(17) 0.6003(17) -0.2808(6) 0.031(3) Uani 1 d . . . H16A H 0.2284 0.6854 -0.3135 0.044(5) Uiso 1 calc R . . H16B H 0.0714 0.6165 -0.2629 0.044(5) Uiso 1 calc R . . C17 C 0.1002(19) 0.4010(17) -0.3259(7) 0.039(4) Uani 1 d . . . H17A H 0.0030 0.3735 -0.3688 0.044(5) Uiso 1 calc R . . H17B H 0.2027 0.3876 -0.3461 0.044(5) Uiso 1 calc R . . C18 C 0.018(2) 0.264(2) -0.2768(8) 0.053(4) Uani 1 d . . . H18A H -0.0241 0.1378 -0.3065 0.044(5) Uiso 1 calc R . . H18B H -0.0904 0.2697 -0.2593 0.044(5) Uiso 1 calc R . . C19 C 0.1717(18) 0.3116(16) -0.2073(8) 0.039(4) Uani 1 d . . . H19A H 0.1175 0.2252 -0.1750 0.044(5) Uiso 1 calc R . . H19B H 0.2745 0.2945 -0.2254 0.044(5) Uiso 1 calc R . . C20 C 0.2526(19) 0.5116(18) -0.1590(8) 0.030(3) Uani 1 d . . . H20 H 0.1489 0.5244 -0.1384 0.033(17) Uiso 1 calc R . . C21 C 0.3429(17) 0.4540(17) -0.0376(7) 0.025(3) Uani 1 d . . . H21A H 0.2861 0.3223 -0.0623 0.044(5) Uiso 1 calc R . . H21B H 0.2464 0.4759 -0.0158 0.044(5) Uiso 1 calc R . . C22 C 0.503(2) 0.502(2) 0.0253(8) 0.038(4) Uani 1 d . . . H22A H 0.6010 0.4856 0.0025 0.044(5) Uiso 1 calc R . . H22B H 0.4563 0.4137 0.0573 0.044(5) Uiso 1 calc R . . C23 C 0.594(2) 0.7029(18) 0.0774(8) 0.035(4) Uani 1 d . . . H23A H 0.4970 0.7209 0.1006 0.044(5) Uiso 1 calc R . . H23B H 0.6890 0.7163 0.1183 0.044(5) Uiso 1 calc R . . C24 C 0.7375(18) 1.0348(19) 0.0775(8) 0.036(4) Uani 1 d U . . H24A H 0.8352 1.0701 0.1214 0.044(5) Uiso 1 calc R . . H24B H 0.6287 1.0372 0.0963 0.044(5) Uiso 1 calc R . . C25 C 0.810(2) 1.1730(19) 0.0296(9) 0.040(4) Uani 1 d U . . H25A H 0.8523 1.2976 0.0606 0.044(5) Uiso 1 calc R . . H25B H 0.9171 1.1697 0.0097 0.044(5) Uiso 1 calc R . . C26 C 0.726(2) 1.242(2) -0.0914(9) 0.047(4) Uani 1 d . . . H26A H 0.8256 1.2238 -0.1116 0.044(5) Uiso 1 calc R . . H26B H 0.7773 1.3734 -0.0669 0.04(4) Uiso 1 calc R . . C27 C 0.562(2) 1.1848(18) -0.1559(9) 0.039(4) Uani 1 d . . . H27A H 0.4593 1.1923 -0.1336 0.044(5) Uiso 1 calc R . . H27B H 0.6035 1.2750 -0.1873 0.044(5) Uiso 1 calc R . . C28 C 0.486(2) 0.9946(17) -0.2069(8) 0.038(4) Uiso 1 d D . . H28A H 0.5880 0.9842 -0.2287 0.044(5) Uiso 1 calc R . . H28B H 0.3912 0.9781 -0.2487 0.044(5) Uiso 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 0.043(2) 0.049(3) 0.044(3) 0.012(2) 0.012(2) 0.027(2) O11 0.116(13) 0.058(10) 0.142(17) -0.005(10) 0.035(12) -0.040(9) O12 0.063(8) 0.086(9) 0.039(7) 0.014(6) 0.008(6) 0.040(7) O13 0.064(8) 0.125(10) 0.039(8) 0.017(7) -0.007(6) 0.055(8) O14 0.079(9) 0.126(11) 0.087(11) -0.007(8) -0.012(8) 0.083(9) Cl2 0.034(2) 0.031(2) 0.043(3) 0.0120(18) 0.0147(19) 0.0159(18) O21 0.100(11) 0.047(8) 0.162(15) 0.054(9) 0.075(11) 0.041(8) O22 0.053(7) 0.053(7) 0.073(8) 0.037(6) 0.045(6) 0.035(6) O23 0.110(10) 0.097(10) 0.040(8) 0.011(7) 0.025(7) 0.051(8) O24 0.045(7) 0.054(7) 0.126(11) 0.046(7) 0.029(7) 0.029(6) Cl3 0.046(3) 0.057(3) 0.039(3) 0.001(2) 0.007(2) 0.028(2) O31 0.086(10) 0.137(12) 0.059(9) 0.034(8) 0.041(7) 0.076(9) O32 0.087(9) 0.158(12) 0.040(9) 0.054(8) 0.028(7) 0.089(9) O33 0.045(10) 0.216(19) 0.132(16) 0.045(14) 0.027(9) -0.011(11) O34 0.36(3) 0.146(14) 0.070(12) -0.054(10) -0.071(14) 0.197(18) Cl4 0.030(2) 0.031(2) 0.033(2) 0.0063(16) 0.0085(17) 0.0151(17) O41 0.079(8) 0.028(6) 0.074(9) 0.025(6) 0.004(7) 0.014(6) O42 0.047(7) 0.086(8) 0.035(6) 0.006(6) 0.009(5) 0.043(6) O43 0.034(7) 0.038(6) 0.110(10) 0.011(6) 0.004(6) 0.016(5) O44 0.080(8) 0.054(7) 0.036(7) 0.014(6) 0.006(6) 0.029(6) N1 0.022(7) 0.031(7) 0.024(7) 0.005(6) -0.004(5) 0.013(6) N2 0.010(6) 0.028(6) 0.026(7) 0.005(5) 0.001(5) 0.006(5) N3 0.044(8) 0.021(7) 0.051(9) 0.004(6) 0.002(7) 0.027(6) N4 0.022(7) 0.035(7) 0.026(8) 0.005(6) -0.002(6) 0.011(6) C1 0.029(8) 0.019(7) 0.018(7) -0.006(6) -0.008(6) 0.010(6) C2 0.023(7) 0.031(8) 0.042(9) 0.005(7) 0.002(7) 0.012(6) C3 0.039(9) 0.045(9) 0.039(9) 0.021(7) 0.006(7) 0.015(7) C4 0.058(10) 0.022(8) 0.047(10) 0.015(7) 0.006(8) 0.008(7) C5 0.042(9) 0.028(8) 0.021(8) 0.003(6) -0.005(7) 0.009(7) C6 0.027(8) 0.033(8) 0.027(9) 0.016(7) 0.017(6) 0.015(7) C7 0.030(8) 0.011(7) 0.034(9) 0.002(7) 0.000(7) 0.004(6) C9 0.044(10) 0.031(9) 0.027(9) -0.018(7) 0.000(8) 0.013(8) C10 0.053(9) 0.033(8) 0.040(10) 0.033(7) 0.022(8) 0.024(7) C11 0.035(9) 0.048(10) 0.046(11) 0.018(8) 0.009(8) 0.025(8) C12 0.045(10) 0.053(10) 0.025(9) 0.005(8) 0.000(8) 0.024(8) C13 0.034(9) 0.021(8) 0.047(10) -0.001(7) 0.010(8) 0.007(7) C14 0.039(9) 0.026(8) 0.027(9) 0.001(7) -0.008(7) 0.022(7) N5 0.023(7) 0.031(7) 0.048(9) 0.025(7) 0.011(6) 0.004(6) N6 0.024(7) 0.021(6) 0.034(7) 0.017(5) 0.008(6) 0.012(5) N7 0.029(7) 0.040(7) 0.037(9) -0.003(6) 0.003(6) 0.021(6) N8 0.027(8) 0.035(7) 0.026(8) 0.000(6) -0.004(6) 0.012(6) C15 0.030(8) 0.016(7) 0.019(8) -0.003(6) 0.009(6) 0.009(6) C16 0.033(8) 0.049(9) 0.013(7) 0.013(6) -0.004(6) 0.021(7) C17 0.047(9) 0.030(8) 0.033(8) -0.005(7) -0.008(7) 0.019(7) C18 0.061(11) 0.048(10) 0.037(10) -0.002(8) -0.003(8) 0.021(9) C19 0.031(8) 0.019(7) 0.060(11) 0.009(7) -0.006(7) 0.008(6) C20 0.039(9) 0.028(8) 0.025(9) 0.011(6) 0.009(7) 0.017(7) C21 0.024(8) 0.033(8) 0.014(8) 0.012(6) 0.005(6) 0.009(6) C22 0.050(10) 0.043(9) 0.040(10) 0.033(8) 0.024(8) 0.029(8) C23 0.036(8) 0.047(9) 0.026(9) 0.019(7) 0.002(7) 0.020(7) C24 0.015(7) 0.054(10) 0.019(9) -0.002(7) -0.015(6) 0.007(7) C25 0.026(8) 0.028(8) 0.047(10) 0.000(7) 0.011(8) 0.000(6) C26 0.045(10) 0.049(11) 0.051(11) 0.027(9) 0.025(9) 0.017(8) C27 0.041(9) 0.019(8) 0.055(11) 0.020(8) 0.018(8) 0.007(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 O11 1.400(12) . yes Cl1 O14 1.406(11) . yes Cl1 O13 1.408(11) . yes Cl1 O12 1.432(11) . yes Cl2 O21 1.408(11) . yes Cl2 O22 1.422(9) . yes Cl2 O24 1.436(10) . yes Cl2 O23 1.438(12) . yes Cl3 O34 1.334(14) . yes Cl3 O31 1.378(11) . yes Cl3 O33 1.402(14) . yes Cl3 O32 1.405(12) . yes Cl4 O44 1.407(10) . yes Cl4 O41 1.422(10) . yes Cl4 O43 1.424(10) . yes Cl4 O42 1.445(9) . yes N1 C1 1.497(17) . yes N1 C14 1.506(16) . yes N1 H1N1 0.86(3) . yes N1 H2N1 0.87(3) . yes N2 C6 1.449(16) . yes N2 C7 1.464(15) . yes N2 H1N2 0.85(3) . yes N3 C12 1.485(17) . yes N3 C11 1.497(18) . yes N3 H1N3 0.86(3) . yes N4 C9 1.493(17) . yes N4 C10 1.519(18) . yes N4 H1N4 0.88(3) . yes N4 H2N4 0.86(3) . yes C1 C6 1.516(17) . yes C1 C2 1.522(17) . yes C1 H1 0.9800 . yes C2 C3 1.522(16) . yes C2 H2A 0.9700 . yes C2 H2B 0.9700 . yes C3 C4 1.484(16) . yes C3 H3A 0.9700 . yes C3 H3B 0.9700 . yes C4 C5 1.509(17) . yes C4 H4A 0.9700 . yes C4 H4B 0.9700 . yes C5 C6 1.553(16) . yes C5 H5A 0.9700 . yes C5 H5B 0.9700 . yes C6 H6 0.9800 . yes C7 C8 1.495(18) . yes C7 H7A 0.9700 . yes C7 H7B 0.9700 . yes C8 C9 1.50(2) . yes C8 H8A 0.9700 . yes C8 H8B 0.9700 . yes C9 H9A 0.9700 . yes C9 H9B 0.9700 . yes C10 C11 1.491(19) . yes C10 H10A 0.9700 . yes C10 H10B 0.9700 . yes C11 H11A 0.9700 . yes C11 H11B 0.9700 . yes C12 C13 1.513(19) . yes C12 H12A 0.9700 . yes C12 H12B 0.9700 . yes C13 C14 1.509(19) . yes C13 H13A 0.9700 . yes C13 H13B 0.9700 . yes C14 H14A 0.9700 . yes C14 H14B 0.9700 . yes N5 C28 1.504(14) . yes N5 C15 1.532(16) . yes N5 H1N5 0.8709 . yes N5 H2N5 0.8656 . yes N6 C21 1.450(15) . yes N6 C20 1.461(17) . yes N6 H1N6 0.86(3) . yes N7 C26 1.472(18) . yes N7 C25 1.486(19) . yes N7 H1N7 0.81(7) . yes N8 C24 1.453(18) . yes N8 C23 1.457(18) . yes N8 H1N8 0.86(3) . yes N8 H2N8 0.86(3) . yes C15 C16 1.484(16) . yes C15 C20 1.558(17) . yes C15 H15 0.9800 . yes C16 C17 1.516(16) . yes C16 H16A 0.9700 . yes C16 H16B 0.9700 . yes C17 C18 1.509(18) . yes C17 H17A 0.9700 . yes C17 H17B 0.9700 . yes C18 C19 1.544(18) . yes C18 H18A 0.9700 . yes C18 H18B 0.9700 . yes C19 C20 1.533(17) . yes C19 H19A 0.9700 . yes C19 H19B 0.9700 . yes C20 H20 0.9800 . yes C21 C22 1.496(19) . yes C21 H21A 0.9700 . yes C21 H21B 0.9700 . yes C22 C23 1.557(19) . yes C22 H22A 0.9700 . yes C22 H22B 0.9700 . yes C23 H23A 0.9700 . yes C23 H23B 0.9700 . yes C24 C25 1.488(19) . yes C24 H24A 0.9700 . yes C24 H24B 0.9700 . yes C25 H25A 0.9700 . yes C25 H25B 0.9700 . yes C26 C27 1.515(19) . yes C26 H26A 0.9700 . yes C26 H26B 0.9700 . yes C27 C28 1.493(18) . yes C27 H27A 0.9700 . yes C27 H27B 0.9700 . yes C28 H28A 0.9700 . yes C28 H28B 0.9700 . yes 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 O11 Cl1 O14 109.4(10) . . yes O11 Cl1 O13 109.9(10) . . yes O14 Cl1 O13 110.4(8) . . yes O11 Cl1 O12 107.8(8) . . yes O14 Cl1 O12 109.2(8) . . yes O13 Cl1 O12 110.0(7) . . yes O21 Cl2 O22 109.9(7) . . yes O21 Cl2 O24 111.2(7) . . yes O22 Cl2 O24 109.9(7) . . yes O21 Cl2 O23 110.3(9) . . yes O22 Cl2 O23 106.2(7) . . yes O24 Cl2 O23 109.2(7) . . yes O34 Cl3 O31 111.4(11) . . yes O34 Cl3 O33 106.4(14) . . yes O31 Cl3 O33 106.9(10) . . yes O34 Cl3 O32 107.9(9) . . yes O31 Cl3 O32 112.2(8) . . yes O33 Cl3 O32 112.0(10) . . yes O44 Cl4 O41 110.7(7) . . yes O44 Cl4 O43 110.8(7) . . yes O41 Cl4 O43 110.2(6) . . yes O44 Cl4 O42 108.8(6) . . yes O41 Cl4 O42 108.7(7) . . yes O43 Cl4 O42 107.5(6) . . yes C1 N1 C14 115.6(11) . . yes C1 N1 H1N1 105(8) . . yes C14 N1 H1N1 119(8) . . yes C1 N1 H2N1 110(8) . . yes C14 N1 H2N1 107(8) . . yes H1N1 N1 H2N1 98(10) . . yes C6 N2 C7 114.9(10) . . yes C6 N2 H1N2 102(6) . . yes C7 N2 H1N2 106(6) . . yes C12 N3 C11 111.5(10) . . yes C12 N3 H1N3 125(6) . . yes C11 N3 H1N3 118(6) . . yes C9 N4 C10 113.3(13) . . yes C9 N4 H1N4 119(8) . . yes C10 N4 H1N4 106(8) . . yes C9 N4 H2N4 102(8) . . yes C10 N4 H2N4 119(8) . . yes H1N4 N4 H2N4 97(10) . . yes N1 C1 C6 107.5(10) . . yes N1 C1 C2 110.0(10) . . yes C6 C1 C2 112.3(10) . . yes N1 C1 H1 109.0 . . yes C6 C1 H1 109.0 . . yes C2 C1 H1 109.0 . . yes C3 C2 C1 110.0(10) . . yes C3 C2 H2A 109.7 . . yes C1 C2 H2A 109.7 . . yes C3 C2 H2B 109.7 . . yes C1 C2 H2B 109.7 . . yes H2A C2 H2B 108.2 . . yes C4 C3 C2 112.8(12) . . yes C4 C3 H3A 109.0 . . yes C2 C3 H3A 109.0 . . yes C4 C3 H3B 109.0 . . yes C2 C3 H3B 109.0 . . yes H3A C3 H3B 107.8 . . yes C3 C4 C5 110.9(11) . . yes C3 C4 H4A 109.5 . . yes C5 C4 H4A 109.5 . . yes C3 C4 H4B 109.5 . . yes C5 C4 H4B 109.5 . . yes H4A C4 H4B 108.1 . . yes C4 C5 C6 113.4(11) . . yes C4 C5 H5A 108.9 . . yes C6 C5 H5A 108.9 . . yes C4 C5 H5B 108.9 . . yes C6 C5 H5B 108.9 . . yes H5A C5 H5B 107.7 . . yes N2 C6 C1 111.8(10) . . yes N2 C6 C5 112.5(10) . . yes C1 C6 C5 108.1(11) . . yes N2 C6 H6 108.1 . . yes C1 C6 H6 108.1 . . yes C5 C6 H6 108.1 . . yes N2 C7 C8 114.0(10) . . yes N2 C7 H7A 108.8 . . yes C8 C7 H7A 108.8 . . yes N2 C7 H7B 108.8 . . yes C8 C7 H7B 108.7 . . yes H7A C7 H7B 107.6 . . yes C7 C8 C9 115.5(12) . . yes C7 C8 H8A 108.4 . . yes C9 C8 H8A 108.4 . . yes C7 C8 H8B 108.4 . . yes C9 C8 H8B 108.4 . . yes H8A C8 H8B 107.5 . . yes N4 C9 C8 110.1(12) . . yes N4 C9 H9A 109.6 . . yes C8 C9 H9A 109.6 . . yes N4 C9 H9B 109.6 . . yes C8 C9 H9B 109.6 . . yes H9A C9 H9B 108.1 . . yes C11 C10 N4 110.0(13) . . yes C11 C10 H10A 109.7 . . yes N4 C10 H10A 109.7 . . yes C11 C10 H10B 109.7 . . yes N4 C10 H10B 109.7 . . yes H10A C10 H10B 108.2 . . yes C10 C11 N3 109.3(12) . . yes C10 C11 H11A 109.8 . . yes N3 C11 H11A 109.8 . . yes C10 C11 H11B 109.8 . . yes N3 C11 H11B 109.8 . . yes H11A C11 H11B 108.3 . . yes N3 C12 C13 109.7(12) . . yes N3 C12 H12A 109.7 . . yes C13 C12 H12A 109.7 . . yes N3 C12 H12B 109.7 . . yes C13 C12 H12B 109.7 . . yes H12A C12 H12B 108.2 . . yes C14 C13 C12 115.1(12) . . yes C14 C13 H13A 108.5 . . yes C12 C13 H13A 108.5 . . yes C14 C13 H13B 108.5 . . yes C12 C13 H13B 108.5 . . yes H13A C13 H13B 107.5 . . yes N1 C14 C13 113.7(12) . . yes N1 C14 H14A 108.8 . . yes C13 C14 H14A 108.8 . . yes N1 C14 H14B 108.8 . . yes C13 C14 H14B 108.8 . . yes H14A C14 H14B 107.7 . . yes C28 N5 C15 114.7(10) . . yes C28 N5 H1N5 118.3 . . yes C15 N5 H1N5 81.0 . . yes C28 N5 H2N5 114.3 . . yes C15 N5 H2N5 104.4 . . yes H1N5 N5 H2N5 118.3 . . yes C21 N6 C20 114.0(10) . . yes C21 N6 H1N6 101(6) . . yes C20 N6 H1N6 123(6) . . yes C26 N7 C25 112.9(12) . . yes C26 N7 H1N7 117(7) . . yes C25 N7 H1N7 89(7) . . yes C24 N8 C23 114.6(13) . . yes C24 N8 H1N8 113(8) . . yes C23 N8 H1N8 111(9) . . yes C24 N8 H2N8 115(8) . . yes C23 N8 H2N8 98(9) . . yes H1N8 N8 H2N8 105(10) . . yes C16 C15 N5 112.0(10) . . yes C16 C15 C20 113.9(11) . . yes N5 C15 C20 106.0(10) . . yes C16 C15 H15 108.2 . . yes N5 C15 H15 108.2 . . yes C20 C15 H15 108.2 . . yes C15 C16 C17 110.0(10) . . yes C15 C16 H16A 109.7 . . yes C17 C16 H16A 109.7 . . yes C15 C16 H16B 109.7 . . yes C17 C16 H16B 109.7 . . yes H16A C16 H16B 108.2 . . yes C18 C17 C16 111.6(11) . . yes C18 C17 H17A 109.3 . . yes C16 C17 H17A 109.3 . . yes C18 C17 H17B 109.3 . . yes C16 C17 H17B 109.3 . . yes H17A C17 H17B 108.0 . . yes C17 C18 C19 109.1(12) . . yes C17 C18 H18A 109.9 . . yes C19 C18 H18A 109.9 . . yes C17 C18 H18B 109.9 . . yes C19 C18 H18B 109.9 . . yes H18A C18 H18B 108.3 . . yes C20 C19 C18 113.3(11) . . yes C20 C19 H19A 108.9 . . yes C18 C19 H19A 108.9 . . yes C20 C19 H19B 108.9 . . yes C18 C19 H19B 108.9 . . yes H19A C19 H19B 107.7 . . yes N6 C20 C19 114.1(10) . . yes N6 C20 C15 111.3(11) . . yes C19 C20 C15 107.1(11) . . yes N6 C20 H20 108.1 . . yes C19 C20 H20 108.1 . . yes C15 C20 H20 108.1 . . yes N6 C21 C22 112.7(11) . . yes N6 C21 H21A 109.1 . . yes C22 C21 H21A 109.1 . . yes N6 C21 H21B 109.1 . . yes C22 C21 H21B 109.1 . . yes H21A C21 H21B 107.8 . . yes C21 C22 C23 115.8(11) . . yes C21 C22 H22A 108.3 . . yes C23 C22 H22A 108.3 . . yes C21 C22 H22B 108.3 . . yes C23 C22 H22B 108.3 . . yes H22A C22 H22B 107.4 . . yes N8 C23 C22 112.5(12) . . yes N8 C23 H23A 109.1 . . yes C22 C23 H23A 109.1 . . yes N8 C23 H23B 109.1 . . yes C22 C23 H23B 109.1 . . yes H23A C23 H23B 107.8 . . yes N8 C24 C25 112.3(13) . . yes N8 C24 H24A 109.1 . . yes C25 C24 H24A 109.1 . . yes N8 C24 H24B 109.1 . . yes C25 C24 H24B 109.1 . . yes H24A C24 H24B 107.9 . . yes N7 C25 C24 109.9(11) . . yes N7 C25 H25A 109.7 . . yes C24 C25 H25A 109.7 . . yes N7 C25 H25B 109.7 . . yes C24 C25 H25B 109.7 . . yes H25A C25 H25B 108.2 . . yes N7 C26 C27 109.3(12) . . yes N7 C26 H26A 109.8 . . yes C27 C26 H26A 109.8 . . yes N7 C26 H26B 109.8 . . yes C27 C26 H26B 109.8 . . yes H26A C26 H26B 108.3 . . yes C28 C27 C26 116.4(13) . . yes C28 C27 H27A 108.2 . . yes C26 C27 H27A 108.2 . . yes C28 C27 H27B 108.2 . . yes C26 C27 H27B 108.2 . . yes H27A C27 H27B 107.3 . . yes C27 C28 N5 112.5(11) . . yes C27 C28 H28A 109.1 . . yes N5 C28 H28A 109.1 . . ye C27 C28 H28B 109.1 . . yes N5 C28 H28B 109.1 . . yes H28A C28 H28B 107.8 . . yes 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 C14 N1 C1 C6 174.4(10) . . . . yes C14 N1 C1 C2 -63.1(13) . . . . yes N1 C1 C2 C3 -176.9(11) . . . . yes C6 C1 C2 C3 -57.3(14) . . . . yes C1 C2 C3 C4 55.7(14) . . . . yes C2 C3 C4 C5 -54.3(15) . . . . yes C3 C4 C5 C6 54.3(16) . . . . yes C7 N2 C6 C1 171.3(10) . . . . yes C7 N2 C6 C5 -66.8(14) . . . . yes N1 C1 C6 N2 -58.5(13) . . . . yes C2 C1 C6 N2 -179.7(10) . . . . yes N1 C1 C6 C5 177.1(10) . . . . yes C2 C1 C6 C5 55.9(14) . . . . yes C4 C5 C6 N2 -178.6(11) . . . . yes C4 C5 C6 C1 -54.6(14) . . . . yes C6 N2 C7 C8 179.5(11) . . . . yes N2 C7 C8 C9 65.8(16) . . . . yes C10 N4 C9 C8 177.8(12) . . . . yes C7 C8 C9 N4 -65.4(17) . . . . yes C9 N4 C10 C11 -169.9(11) . . . . yes N4 C10 C11 N3 61.5(15) . . . . yes C12 N3 C11 C10 -176.6(12) . . . . yes C11 N3 C12 C13 176.0(12) . . . . yes N3 C12 C13 C14 -68.0(16) . . . . yes C1 N1 C14 C13 -174.6(11) . . . . yes C12 C13 C14 N1 67.5(16) . . . . yes C28 N5 C15 C16 -59.4(14) . . . . yes C28 N5 C15 C20 175.8(11) . . . . yes N5 C15 C16 C17 -178.0(10) . . . . yes C20 C15 C16 C17 -57.7(14) . . . . yes C15 C16 C17 C18 58.4(15) . . . . yes C16 C17 C18 C19 -57.4(15) . . . . yes C17 C18 C19 C20 57.0(16) . . . . yes C21 N6 C20 C19 -63.8(15) . . . . yes C21 N6 C20 C15 174.9(10) . . . . yes C18 C19 C20 N6 -177.6(12) . . . . yes C18 C19 C20 C15 -54.0(15) . . . . yes C16 C15 C20 N6 -179.8(10) . . . . yes N5 C15 C20 N6 -56.1(13) . . . . yes C16 C15 C20 C19 54.9(14) . . . . yes N5 C15 C20 C19 178.6(10) . . . . yes C20 N6 C21 C22 177.0(11) . . . . yes N6 C21 C22 C23 66.0(15) . . . . yes C24 N8 C23 C22 168.8(11) . . . . yes C21 C22 C23 N8 -63.0(16) . . . . yes C23 N8 C24 C25 -174.5(11) . . . . yes C26 N7 C25 C24 -171.4(12) . . . . yes N8 C24 C25 N7 62.9(15) . . . . yes C25 N7 C26 C27 178.6(12) . . . . yes N7 C26 C27 C28 -68.3(17) . . . . yes C26 C27 C28 N5 64.4(16) . . . . yes C15 N5 C28 C27 -178.2(11) . . . . yes _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.395 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.088 #===END