Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Philip Gale' 'Gareth W. Bates' 'Wim Dehaen' 'Maartin Kostermans' 'Mark E. Light' _publ_contact_author_name 'Philip Gale' _publ_contact_author_address ; School of Chemistry University of Southampton Southampton SO17 1BJ UNITED KINGDOM ; _publ_contact_author_email PHILIP.GALE@SOTON.AC.UK _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Ionic liquid inclusion in N-confused calix[4]pyrrole ; # Attachment '1151_1534_combined.cif' data_2005sot1151 _database_code_depnum_ccdc_archive 'CCDC 602302' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H36 N4, C6 H11 N2, C H2 Cl2, Cl' _chemical_formula_sum 'C35 H49 Cl3 N6' _chemical_formula_weight 660.15 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.5513(19) _cell_length_b 15.868(2) _cell_length_c 10.5844(19) _cell_angle_alpha 90.00 _cell_angle_beta 100.578(6) _cell_angle_gamma 90.00 _cell_volume 1742.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4853 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.10 _exptl_crystal_description Lath _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9330 _exptl_absorpt_correction_T_max 0.9941 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 7116 reflections reduced R(int) from 0.1146 to 0.0862 Ratio of minimum to maximum apparent transmission: 0.108216 The given Tmin and Tmax were generated using the SHELX SIZE command ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating Anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15161 _diffrn_reflns_av_R_equivalents 0.1688 _diffrn_reflns_av_sigmaI/netI 0.2231 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 27.26 _reflns_number_total 6950 _reflns_number_gt 3872 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0792P)^2^+0.3572P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(11) _refine_ls_number_reflns 6950 _refine_ls_number_parameters 407 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1819 _refine_ls_R_factor_gt 0.0932 _refine_ls_wR_factor_ref 0.2228 _refine_ls_wR_factor_gt 0.1866 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.3104(6) 0.2194(4) 0.0991(6) 0.0257(16) Uani 1 1 d . . . C2 C -0.4030(6) 0.1823(4) 0.1601(7) 0.0291(16) Uani 1 1 d . . . H2 H -0.4693 0.1445 0.1231 0.035 Uiso 1 1 calc R . . C3 C -0.3782(7) 0.2124(4) 0.2888(7) 0.0335(17) Uani 1 1 d . . . H3 H -0.4252 0.1972 0.3537 0.040 Uiso 1 1 calc R . . C4 C -0.2765(6) 0.2665(4) 0.3042(7) 0.0276(16) Uani 1 1 d . . . C5 C -0.2068(7) 0.3129(4) 0.4211(7) 0.0312(17) Uani 1 1 d . . . C6 C -0.3009(7) 0.3227(4) 0.5180(7) 0.0327(17) Uani 1 1 d . . . H6A H -0.3253 0.2668 0.5448 0.049 Uiso 1 1 calc R . . H6B H -0.3783 0.3531 0.4765 0.049 Uiso 1 1 calc R . . H6C H -0.2582 0.3543 0.5934 0.049 Uiso 1 1 calc R . . C7 C -0.1701(7) 0.4031(4) 0.3869(7) 0.0334(17) Uani 1 1 d . . . H7A H -0.1327 0.4334 0.4657 0.050 Uiso 1 1 calc R . . H7B H -0.2474 0.4329 0.3436 0.050 Uiso 1 1 calc R . . H7C H -0.1069 0.4005 0.3297 0.050 Uiso 1 1 calc R . . C8 C -0.0888(6) 0.2649(4) 0.4868(6) 0.0273(15) Uani 1 1 d . . . C9 C -0.0671(7) 0.2180(5) 0.5963(7) 0.0324(17) Uani 1 1 d . . . H9 H -0.1256 0.2104 0.6538 0.039 Uiso 1 1 calc R . . C10 C 0.0574(7) 0.1827(5) 0.6096(7) 0.0326(17) Uani 1 1 d . . . H10 H 0.0971 0.1472 0.6777 0.039 Uiso 1 1 calc R . . C11 C 0.1113(6) 0.2083(4) 0.5080(6) 0.0271(16) Uani 1 1 d . . . C12 C 0.2452(6) 0.1908(4) 0.4786(6) 0.0262(16) Uani 1 1 d . . . C13 C 0.3260(8) 0.1472(5) 0.5943(7) 0.041(2) Uani 1 1 d . . . H13A H 0.4116 0.1344 0.5758 0.062 Uiso 1 1 calc R . . H13B H 0.2835 0.0947 0.6121 0.062 Uiso 1 1 calc R . . H13C H 0.3348 0.1843 0.6693 0.062 Uiso 1 1 calc R . . C14 C 0.3108(7) 0.2756(5) 0.4583(8) 0.0382(19) Uani 1 1 d . . . H14A H 0.3965 0.2649 0.4385 0.057 Uiso 1 1 calc R . . H14B H 0.3192 0.3096 0.5368 0.057 Uiso 1 1 calc R . . H14C H 0.2583 0.3062 0.3868 0.057 Uiso 1 1 calc R . . C15 C 0.2421(6) 0.1353(4) 0.3619(7) 0.0304(17) Uani 1 1 d . . . C16 C 0.2897(6) 0.0549(4) 0.3513(7) 0.0316(17) Uani 1 1 d . . . H16 H 0.3274 0.0201 0.4211 0.038 Uiso 1 1 calc R . . C17 C 0.2732(7) 0.0331(5) 0.2206(7) 0.0334(17) Uani 1 1 d . . . H17 H 0.2971 -0.0187 0.1868 0.040 Uiso 1 1 calc R . . C18 C 0.2162(6) 0.1005(4) 0.1504(7) 0.0295(17) Uani 1 1 d . . . C19 C 0.1782(6) 0.1136(4) 0.0076(6) 0.0256(16) Uani 1 1 d . . . C20 C 0.2307(7) 0.0408(4) -0.0633(7) 0.0320(17) Uani 1 1 d . . . H20A H 0.1963 -0.0127 -0.0379 0.048 Uiso 1 1 calc R . . H20B H 0.3250 0.0400 -0.0410 0.048 Uiso 1 1 calc R . . H20C H 0.2042 0.0486 -0.1563 0.048 Uiso 1 1 calc R . . C21 C 0.2381(6) 0.1971(4) -0.0289(7) 0.0320(17) Uani 1 1 d . . . H21A H 0.2305 0.2001 -0.1225 0.048 Uiso 1 1 calc R . . H21B H 0.3293 0.1992 0.0117 0.048 Uiso 1 1 calc R . . H21C H 0.1925 0.2448 0.0009 0.048 Uiso 1 1 calc R . . C22 C 0.0320(6) 0.1209(4) -0.0317(6) 0.0267(16) Uani 1 1 d . . . C23 C -0.0466(6) 0.1862(4) -0.0108(6) 0.0254(15) Uani 1 1 d . . . H23 H -0.0187 0.2393 0.0255 0.030 Uiso 1 1 calc R . . C24 C -0.1766(6) 0.1612(4) -0.0525(7) 0.0277(16) Uani 1 1 d . . . C25 C -0.1728(6) 0.0807(4) -0.0965(7) 0.0280(16) Uani 1 1 d . . . H25 H -0.2457 0.0470 -0.1299 0.034 Uiso 1 1 calc R . . C26 C -0.2948(6) 0.2131(4) -0.0394(7) 0.0275(16) Uani 1 1 d . . . C27 C -0.4138(7) 0.1747(5) -0.1205(8) 0.0390(18) Uani 1 1 d . . . H27A H -0.4275 0.1181 -0.0885 0.059 Uiso 1 1 calc R . . H27B H -0.4020 0.1711 -0.2100 0.059 Uiso 1 1 calc R . . H27C H -0.4889 0.2100 -0.1154 0.059 Uiso 1 1 calc R . . C28 C -0.2771(8) 0.3043(4) -0.0899(7) 0.0377(19) Uani 1 1 d . . . H28A H -0.3515 0.3390 -0.0799 0.056 Uiso 1 1 calc R . . H28B H -0.2703 0.3018 -0.1809 0.056 Uiso 1 1 calc R . . H28C H -0.1984 0.3292 -0.0404 0.056 Uiso 1 1 calc R . . C29 C -0.3200(11) 0.0230(7) 0.5205(12) 0.086(4) Uani 1 1 d . . . H29A H -0.3330 0.0788 0.4808 0.129 Uiso 1 1 calc R . . H29B H -0.3485 0.0237 0.6036 0.129 Uiso 1 1 calc R . . H29C H -0.3703 -0.0188 0.4642 0.129 Uiso 1 1 calc R . . C30 C -0.1801(10) 0.0004(5) 0.5404(8) 0.057(3) Uani 1 1 d . . . H30A H -0.1291 0.0430 0.5963 0.069 Uiso 1 1 calc R . . H30B H -0.1664 -0.0549 0.5840 0.069 Uiso 1 1 calc R . . C31 C -0.1195(7) 0.0636(5) 0.3403(7) 0.0366(18) Uani 1 1 d . . . H31 H -0.1338 0.1212 0.3580 0.044 Uiso 1 1 calc R . . C32 C -0.0801(7) 0.0349(4) 0.2374(7) 0.0332(18) Uani 1 1 d . . . H32 H -0.0624 0.0673 0.1672 0.040 Uiso 1 1 calc R . . C33 C -0.1046(6) -0.0736(4) 0.3600(7) 0.0329(17) Uani 1 1 d . . . H33 H -0.1068 -0.1295 0.3916 0.040 Uiso 1 1 calc R . . C34 C -0.0232(8) -0.1093(5) 0.1618(8) 0.048(2) Uani 1 1 d . . . H34A H 0.0651 -0.0943 0.1540 0.072 Uiso 1 1 calc R . . H34B H -0.0794 -0.1055 0.0773 0.072 Uiso 1 1 calc R . . H34C H -0.0246 -0.1671 0.1943 0.072 Uiso 1 1 calc R . . N1 N -0.2355(5) 0.2685(3) 0.1877(5) 0.0278(13) Uani 1 1 d . . . H1 H -0.1690 0.2979 0.1728 0.033 Uiso 1 1 calc R . . N2 N 0.0213(5) 0.2585(3) 0.4321(5) 0.0239(12) Uani 1 1 d . . . H2A H 0.0319 0.2828 0.3600 0.029 Uiso 1 1 calc R . . N3 N 0.1982(5) 0.1628(3) 0.2371(5) 0.0263(13) Uani 1 1 d . . . H3A H 0.1640 0.2126 0.2160 0.032 Uiso 1 1 calc R . . N4 N -0.0466(5) 0.0563(3) -0.0845(5) 0.0297(13) Uani 1 1 d . . . H4 H -0.0201 0.0070 -0.1070 0.036 Uiso 1 1 calc R . . N5 N -0.1366(6) -0.0035(3) 0.4181(6) 0.0318(14) Uani 1 1 d . . . N6 N -0.0694(5) -0.0511(4) 0.2513(6) 0.0313(14) Uani 1 1 d . . . Cl1 Cl 0.07138(17) 0.36097(10) 0.18170(17) 0.0330(4) Uani 1 1 d . . . C35 C 0.4110(8) 0.3759(5) 0.1105(8) 0.046(2) Uani 1 1 d . . . H35A H 0.3262 0.3614 0.1321 0.055 Uiso 1 1 calc R . . H35B H 0.4633 0.3237 0.1166 0.055 Uiso 1 1 calc R . . Cl2 Cl 0.4881(2) 0.44945(13) 0.2212(2) 0.0535(6) Uani 1 1 d . . . Cl3 Cl 0.3882(2) 0.41447(14) -0.0482(2) 0.0594(7) 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 C1 0.018(4) 0.030(4) 0.028(4) 0.000(3) 0.001(3) 0.004(3) C2 0.032(4) 0.023(4) 0.031(4) 0.000(3) 0.003(3) -0.004(3) C3 0.036(4) 0.032(4) 0.034(4) 0.006(3) 0.012(3) -0.001(4) C4 0.024(4) 0.020(3) 0.039(4) 0.004(3) 0.006(3) 0.004(3) C5 0.037(4) 0.028(4) 0.031(4) -0.001(3) 0.012(3) -0.002(3) C6 0.035(4) 0.028(4) 0.034(4) 0.000(3) 0.003(3) 0.011(3) C7 0.035(4) 0.028(4) 0.038(4) -0.002(3) 0.010(3) 0.000(3) C8 0.026(4) 0.028(4) 0.029(4) -0.003(3) 0.006(3) -0.003(3) C9 0.026(4) 0.037(4) 0.036(4) 0.003(3) 0.009(3) 0.001(3) C10 0.037(4) 0.030(4) 0.029(4) -0.001(3) 0.001(3) 0.006(3) C11 0.029(4) 0.027(4) 0.024(4) 0.000(3) 0.002(3) 0.000(3) C12 0.025(4) 0.028(4) 0.026(4) -0.005(3) 0.007(3) 0.004(3) C13 0.044(5) 0.045(5) 0.032(5) -0.008(4) -0.001(4) 0.007(4) C14 0.028(4) 0.035(4) 0.053(5) -0.012(4) 0.011(4) -0.008(3) C15 0.019(4) 0.029(4) 0.041(5) 0.001(3) 0.002(3) 0.000(3) C16 0.029(4) 0.030(4) 0.034(4) 0.005(3) 0.000(3) -0.002(3) C17 0.033(4) 0.032(4) 0.037(4) -0.002(3) 0.011(3) 0.002(3) C18 0.025(4) 0.021(4) 0.044(5) -0.007(3) 0.010(3) -0.001(3) C19 0.026(4) 0.018(3) 0.035(4) 0.001(3) 0.010(3) 0.003(3) C20 0.035(4) 0.026(4) 0.036(4) -0.003(3) 0.009(3) 0.004(3) C21 0.022(4) 0.039(4) 0.038(4) 0.004(3) 0.013(3) -0.002(3) C22 0.030(4) 0.026(4) 0.024(4) 0.001(3) 0.005(3) -0.004(3) C23 0.026(4) 0.025(4) 0.027(4) 0.000(3) 0.009(3) 0.000(3) C24 0.025(4) 0.022(4) 0.035(4) 0.003(3) 0.005(3) -0.001(3) C25 0.017(4) 0.024(4) 0.041(4) -0.005(3) 0.001(3) -0.005(3) C26 0.021(4) 0.025(4) 0.035(4) -0.002(3) 0.002(3) -0.003(3) C27 0.031(4) 0.039(4) 0.047(5) -0.008(4) 0.006(4) 0.006(4) C28 0.044(5) 0.030(4) 0.041(5) 0.005(3) 0.011(4) 0.000(4) C29 0.086(8) 0.081(7) 0.111(9) 0.055(7) 0.071(7) 0.045(6) C30 0.095(8) 0.035(5) 0.051(6) 0.001(4) 0.038(5) 0.004(5) C31 0.037(4) 0.028(4) 0.048(5) 0.008(4) 0.017(4) -0.001(3) C32 0.042(4) 0.026(4) 0.035(5) 0.005(3) 0.014(4) -0.008(3) C33 0.034(4) 0.021(4) 0.044(5) 0.008(3) 0.007(4) 0.001(3) C34 0.051(5) 0.036(4) 0.062(6) -0.001(4) 0.026(4) 0.005(4) N1 0.024(3) 0.021(3) 0.041(4) 0.002(3) 0.012(3) -0.004(3) N2 0.025(3) 0.026(3) 0.020(3) -0.002(2) 0.003(2) -0.005(3) N3 0.029(3) 0.021(3) 0.028(3) -0.001(2) 0.004(3) 0.004(2) N4 0.025(3) 0.019(3) 0.047(4) -0.008(3) 0.012(3) 0.000(3) N5 0.041(4) 0.022(3) 0.034(3) 0.001(3) 0.010(3) 0.008(3) N6 0.028(3) 0.023(3) 0.042(4) -0.008(3) 0.006(3) -0.003(3) Cl1 0.0384(10) 0.0239(9) 0.0391(11) -0.0003(8) 0.0139(8) -0.0032(8) C35 0.047(5) 0.035(5) 0.056(5) -0.004(4) 0.009(4) 0.000(4) Cl2 0.0440(12) 0.0401(11) 0.0725(16) -0.0017(11) 0.0007(11) 0.0021(10) Cl3 0.0505(13) 0.0655(15) 0.0639(16) 0.0011(11) 0.0147(11) 0.0104(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.356(9) . ? C1 C2 1.396(9) . ? C1 C26 1.508(10) . ? C2 C3 1.421(10) . ? C3 C4 1.359(10) . ? C4 N1 1.380(8) . ? C4 C5 1.511(10) . ? C5 C8 1.514(10) . ? C5 C7 1.544(9) . ? C5 C6 1.560(10) . ? C8 C9 1.362(10) . ? C8 N2 1.394(8) . ? C9 C10 1.411(10) . ? C10 C11 1.367(9) . ? C11 N2 1.378(8) . ? C11 C12 1.527(9) . ? C12 C15 1.513(10) . ? C12 C13 1.524(10) . ? C12 C14 1.546(10) . ? C15 C16 1.382(10) . ? C15 N3 1.388(9) . ? C16 C17 1.406(10) . ? C17 C18 1.376(10) . ? C18 N3 1.384(8) . ? C18 C19 1.506(10) . ? C19 C22 1.527(9) . ? C19 C20 1.535(9) . ? C19 C21 1.547(9) . ? C22 C23 1.370(9) . ? C22 N4 1.371(8) . ? C23 C24 1.419(9) . ? C24 C25 1.362(9) . ? C24 C26 1.522(10) . ? C25 N4 1.370(8) . ? C26 C27 1.513(9) . ? C26 C28 1.566(10) . ? C29 C30 1.496(13) . ? C30 N5 1.453(10) . ? C31 C32 1.316(10) . ? C31 N5 1.378(9) . ? C32 N6 1.375(9) . ? C33 N6 1.321(9) . ? C33 N5 1.344(9) . ? C34 N6 1.469(9) . ? C35 Cl2 1.746(8) . ? C35 Cl3 1.762(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 106.9(6) . . ? N1 C1 C26 123.8(6) . . ? C2 C1 C26 129.2(6) . . ? C1 C2 C3 106.3(6) . . ? C4 C3 C2 109.2(6) . . ? C3 C4 N1 106.1(6) . . ? C3 C4 C5 131.4(6) . . ? N1 C4 C5 122.4(6) . . ? C4 C5 C8 111.5(6) . . ? C4 C5 C7 111.4(6) . . ? C8 C5 C7 110.7(6) . . ? C4 C5 C6 108.3(6) . . ? C8 C5 C6 108.5(6) . . ? C7 C5 C6 106.2(6) . . ? C9 C8 N2 106.9(6) . . ? C9 C8 C5 131.4(6) . . ? N2 C8 C5 121.6(6) . . ? C8 C9 C10 108.0(6) . . ? C11 C10 C9 108.5(6) . . ? C10 C11 N2 106.8(6) . . ? C10 C11 C12 129.9(6) . . ? N2 C11 C12 123.3(6) . . ? C15 C12 C13 108.4(6) . . ? C15 C12 C11 112.9(5) . . ? C13 C12 C11 108.7(6) . . ? C15 C12 C14 109.7(6) . . ? C13 C12 C14 108.0(6) . . ? C11 C12 C14 109.0(5) . . ? C16 C15 N3 106.0(6) . . ? C16 C15 C12 130.5(6) . . ? N3 C15 C12 123.2(6) . . ? C15 C16 C17 109.0(6) . . ? C18 C17 C16 107.6(6) . . ? C17 C18 N3 107.3(6) . . ? C17 C18 C19 131.2(6) . . ? N3 C18 C19 121.5(6) . . ? C18 C19 C22 110.7(5) . . ? C18 C19 C20 109.5(5) . . ? C22 C19 C20 111.2(6) . . ? C18 C19 C21 108.8(5) . . ? C22 C19 C21 107.8(5) . . ? C20 C19 C21 108.8(5) . . ? C23 C22 N4 107.0(5) . . ? C23 C22 C19 128.7(6) . . ? N4 C22 C19 124.0(6) . . ? C22 C23 C24 108.5(6) . . ? C25 C24 C23 106.3(6) . . ? C25 C24 C26 127.9(6) . . ? C23 C24 C26 125.6(6) . . ? C24 C25 N4 108.8(6) . . ? C1 C26 C27 110.6(6) . . ? C1 C26 C24 111.2(6) . . ? C27 C26 C24 109.8(6) . . ? C1 C26 C28 108.2(6) . . ? C27 C26 C28 108.5(6) . . ? C24 C26 C28 108.5(5) . . ? N5 C30 C29 110.5(8) . . ? C32 C31 N5 108.8(7) . . ? C31 C32 N6 106.7(6) . . ? N6 C33 N5 108.0(6) . . ? C1 N1 C4 111.4(5) . . ? C11 N2 C8 109.8(5) . . ? C18 N3 C15 110.1(6) . . ? C25 N4 C22 109.4(5) . . ? C33 N5 C31 107.1(6) . . ? C33 N5 C30 126.1(6) . . ? C31 N5 C30 126.7(6) . . ? C33 N6 C32 109.3(6) . . ? C33 N6 C34 124.8(6) . . ? C32 N6 C34 125.9(6) . . ? Cl2 C35 Cl3 111.9(4) . . ? 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 H1 Cl1 0.88 2.71 3.566(6) 163.7 . N2 H2A Cl1 0.88 2.36 3.235(6) 173.4 . N3 H3A Cl1 0.88 2.55 3.425(6) 173.6 . N4 H4 Cl1 0.88 2.48 3.262(6) 149.2 2_545 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.26 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.573 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.083 #===END data_2005sot1534 _database_code_depnum_ccdc_archive 'CCDC 602303' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H53 Cl3 N6' _chemical_formula_weight 688.20 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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5860(11) _cell_length_b 15.8800(17) _cell_length_c 21.868(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.452(2) _cell_angle_gamma 90.00 _cell_volume 3665.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4130 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 21.4 _exptl_crystal_description Lath _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9585 _exptl_absorpt_correction_T_max 0.9972 _exptl_absorpt_process_details 'Bruker SADABS' # absolute Tmin and Tmax unknown, but SADABS gives ratio as 0.804 _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.6709 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 27170 _diffrn_reflns_av_R_equivalents 0.0700 _diffrn_reflns_av_sigmaI/netI 0.0587 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 23.54 _reflns_number_total 6453 _reflns_number_gt 4640 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0456P)^2^+14.3833P] 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 6453 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1131 _refine_ls_R_factor_gt 0.0813 _refine_ls_wR_factor_ref 0.1925 _refine_ls_wR_factor_gt 0.1776 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.032 _refine_ls_shift/su_mean 0.005 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0018(4) 0.1115(3) 0.1712(2) 0.0281(10) Uani 1 1 d . . . C2 C 1.0437(4) 0.1933(3) 0.1731(2) 0.0296(10) Uani 1 1 d . . . H2 H 1.0569 0.2275 0.1385 0.035 Uiso 1 1 calc R . . N1 N 1.0634(3) 0.2171(2) 0.23297(19) 0.0335(9) Uani 1 1 d . . . H3 H 1.0896 0.2671 0.2457 0.040 Uiso 1 1 calc R . . C4 C 1.0359(4) 0.1507(3) 0.2708(2) 0.0273(10) Uani 1 1 d . . . C5 C 1.0327(4) 0.1570(3) 0.3399(2) 0.0305(10) Uani 1 1 d . . . C6 C 1.0862(4) 0.0754(3) 0.3697(2) 0.0350(11) Uani 1 1 d . . . H6A H 1.0346 0.0274 0.3545 0.052 Uiso 1 1 calc R . . H6B H 1.0843 0.0793 0.4144 0.052 Uiso 1 1 calc R . . H6C H 1.1738 0.0674 0.3593 0.052 Uiso 1 1 calc R . . C7 C 1.1129(5) 0.2316(3) 0.3655(2) 0.0409(12) Uani 1 1 d . . . H7A H 1.2018 0.2225 0.3576 0.061 Uiso 1 1 calc R . . H7B H 1.1057 0.2362 0.4098 0.061 Uiso 1 1 calc R . . H7C H 1.0824 0.2837 0.3453 0.061 Uiso 1 1 calc R . . C8 C 0.8966(4) 0.1689(3) 0.3551(2) 0.0290(10) Uani 1 1 d . . . C9 C 0.8344(4) 0.2376(3) 0.3762(2) 0.0319(10) Uani 1 1 d . . . H9 H 0.8701 0.2917 0.3841 0.038 Uiso 1 1 calc R . . C10 C 0.7077(4) 0.2137(3) 0.3840(2) 0.0305(10) Uani 1 1 d . . . H10 H 0.6437 0.2491 0.3981 0.037 Uiso 1 1 calc R . . C11 C 0.6934(4) 0.1310(3) 0.3678(2) 0.0280(10) Uani 1 1 d . . . C12 C 0.5793(4) 0.0721(3) 0.3704(2) 0.0279(10) Uani 1 1 d . . . C13 C 0.6222(5) -0.0101(3) 0.4033(2) 0.0361(11) Uani 1 1 d . . . H13A H 0.5484 -0.0462 0.4076 0.054 Uiso 1 1 calc R . . H13B H 0.6627 0.0032 0.4439 0.054 Uiso 1 1 calc R . . H13C H 0.6827 -0.0395 0.3791 0.054 Uiso 1 1 calc R . . C14 C 0.4825(5) 0.1154(3) 0.4082(2) 0.0355(11) Uani 1 1 d . . . H14A H 0.4547 0.1682 0.3882 0.053 Uiso 1 1 calc R . . H14B H 0.5214 0.1275 0.4494 0.053 Uiso 1 1 calc R . . H14C H 0.4093 0.0783 0.4113 0.053 Uiso 1 1 calc R . . C15 C 0.5167(4) 0.0527(3) 0.3072(2) 0.0246(9) Uani 1 1 d . . . C16 C 0.3990(4) 0.0749(3) 0.2815(2) 0.0278(10) Uani 1 1 d . . . H16 H 0.3386 0.1085 0.3003 0.033 Uiso 1 1 calc R . . C17 C 0.3832(4) 0.0393(3) 0.2225(2) 0.0280(10) Uani 1 1 d . . . H17 H 0.3101 0.0446 0.1947 0.034 Uiso 1 1 calc R . . C18 C 0.4918(4) -0.0044(3) 0.21184(19) 0.0247(9) Uani 1 1 d . . . C19 C 0.5282(4) -0.0510(3) 0.1554(2) 0.0261(10) Uani 1 1 d . . . C20 C 0.4082(4) -0.0616(3) 0.1112(2) 0.0318(11) Uani 1 1 d . . . H20A H 0.3760 -0.0060 0.0983 0.048 Uiso 1 1 calc R . . H20B H 0.3433 -0.0918 0.1321 0.048 Uiso 1 1 calc R . . H20C H 0.4293 -0.0937 0.0751 0.048 Uiso 1 1 calc R . . C21 C 0.5785(4) -0.1399(3) 0.1725(2) 0.0276(10) Uani 1 1 d . . . H21A H 0.6069 -0.1675 0.1359 0.041 Uiso 1 1 calc R . . H21B H 0.5108 -0.1732 0.1887 0.041 Uiso 1 1 calc R . . H21C H 0.6498 -0.1353 0.2037 0.041 Uiso 1 1 calc R . . C22 C 0.6270(4) -0.0028(3) 0.1231(2) 0.0270(10) Uani 1 1 d . . . C23 C 0.6159(5) 0.0431(3) 0.0698(2) 0.0373(12) Uani 1 1 d . . . H23 H 0.5399 0.0522 0.0446 0.045 Uiso 1 1 calc R . . C24 C 0.7365(5) 0.0745(3) 0.0590(2) 0.0377(12) Uani 1 1 d . . . H24 H 0.7559 0.1079 0.0249 0.045 Uiso 1 1 calc R . . C25 C 0.8204(4) 0.0487(3) 0.1055(2) 0.0289(10) Uani 1 1 d . . . C26 C 0.9636(4) 0.0594(3) 0.1145(2) 0.0289(10) Uani 1 1 d . . . C27 C 1.0103(5) 0.1019(3) 0.0572(2) 0.0396(12) Uani 1 1 d . . . H27A H 0.9760 0.1592 0.0535 0.059 Uiso 1 1 calc R . . H27B H 0.9815 0.0694 0.0206 0.059 Uiso 1 1 calc R . . H27C H 1.1031 0.1043 0.0608 0.059 Uiso 1 1 calc R . . C28 C 1.0239(4) -0.0288(3) 0.1214(2) 0.0340(11) Uani 1 1 d . . . H28A H 1.1164 -0.0236 0.1247 0.051 Uiso 1 1 calc R . . H28B H 0.9970 -0.0631 0.0854 0.051 Uiso 1 1 calc R . . H28C H 0.9966 -0.0560 0.1584 0.051 Uiso 1 1 calc R . . C29 C 0.8299(5) 0.3745(3) 0.2237(2) 0.0403(12) Uani 1 1 d . . . H29A H 0.8879 0.3715 0.1910 0.060 Uiso 1 1 calc R . . H29B H 0.8755 0.3596 0.2629 0.060 Uiso 1 1 calc R . . H29C H 0.7965 0.4319 0.2261 0.060 Uiso 1 1 calc R . . C30 C 0.7355(4) 0.2287(3) 0.2108(2) 0.0328(11) Uani 1 1 d . . . H30 H 0.8104 0.1966 0.2198 0.039 Uiso 1 1 calc R . . C31 C 0.6180(4) 0.1989(3) 0.1958(2) 0.0354(11) Uani 1 1 d . . . H31 H 0.5948 0.1412 0.1921 0.042 Uiso 1 1 calc R . . C32 C 0.6058(4) 0.3368(3) 0.1965(2) 0.0278(10) Uani 1 1 d . . . H32 H 0.5737 0.3926 0.1937 0.033 Uiso 1 1 calc R . . C33 C 0.3985(4) 0.2624(3) 0.1734(2) 0.0367(11) Uani 1 1 d . . . H33A H 0.3642 0.3202 0.1685 0.044 Uiso 1 1 calc R . . H33B H 0.3597 0.2358 0.2083 0.044 Uiso 1 1 calc R . . C34 C 0.3629(5) 0.2124(4) 0.1153(3) 0.0492(14) Uani 1 1 d . . . H34A H 0.4025 0.1560 0.1194 0.059 Uiso 1 1 calc R . . H34B H 0.2699 0.2045 0.1112 0.059 Uiso 1 1 calc R . . C35 C 0.4019(7) 0.2525(4) 0.0597(3) 0.0629(17) Uani 1 1 d . . . H35A H 0.4956 0.2539 0.0610 0.075 Uiso 1 1 calc R . . H35B H 0.3707 0.3112 0.0576 0.075 Uiso 1 1 calc R . . C36 C 0.3473(6) 0.2025(4) 0.0003(2) 0.0542(15) Uani 1 1 d . . . H36A H 0.3833 0.1456 0.0008 0.081 Uiso 1 1 calc R . . H36B H 0.3702 0.2322 -0.0366 0.081 Uiso 1 1 calc R . . H36C H 0.2549 0.1988 0.0000 0.081 Uiso 1 1 calc R . . C46 C 0.8738(6) 0.1112(5) 0.5106(3) 0.0662(18) Uani 1 1 d . . . H46A H 0.8664 0.0535 0.4936 0.079 Uiso 1 1 calc R . . H46B H 0.8651 0.1512 0.4758 0.079 Uiso 1 1 calc R . . C3 C 0.9988(4) 0.0852(3) 0.2328(2) 0.0258(9) Uani 1 1 d . . . H1 H 0.9750 0.0308 0.2457 0.031 Uiso 1 1 calc R . . N2 N 0.8094(3) 0.1043(2) 0.35030(17) 0.0292(9) Uani 1 1 d . . . H2A H 0.8255 0.0531 0.3378 0.035 Uiso 1 1 calc R . . N3 N 0.5723(3) 0.0044(2) 0.26446(16) 0.0250(8) Uani 1 1 d . . . H3A H 0.6485 -0.0179 0.2698 0.030 Uiso 1 1 calc R . . N4 N 0.7528(3) 0.0021(2) 0.14501(16) 0.0268(8) Uani 1 1 d . . . H4 H 0.7852 -0.0212 0.1792 0.032 Uiso 1 1 calc R . . N5 N 0.7250(3) 0.3156(2) 0.21045(17) 0.0272(8) Uani 1 1 d . . . N6 N 0.5376(3) 0.2665(2) 0.18687(17) 0.0264(8) Uani 1 1 d . . . Cl1 Cl 0.84138(10) -0.08911(7) 0.28623(5) 0.0317(3) Uani 1 1 d . . . Cl2 Cl 1.02331(17) 0.12320(11) 0.54856(7) 0.0660(5) Uani 1 1 d . . . Cl3 Cl 0.7502(2) 0.1282(2) 0.55760(9) 0.1186(10) 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 C1 0.018(2) 0.026(2) 0.040(3) 0.002(2) -0.0004(19) 0.0011(18) C2 0.025(2) 0.028(2) 0.035(3) 0.002(2) 0.0050(19) -0.0006(19) N1 0.031(2) 0.0208(19) 0.049(3) 0.0004(17) 0.0032(18) -0.0068(16) C4 0.018(2) 0.023(2) 0.041(3) 0.0028(19) -0.0009(18) 0.0004(17) C5 0.023(2) 0.029(2) 0.038(3) -0.005(2) -0.0056(19) -0.0022(19) C6 0.022(2) 0.044(3) 0.037(3) 0.000(2) -0.004(2) 0.004(2) C7 0.028(3) 0.040(3) 0.054(3) -0.013(2) -0.003(2) -0.006(2) C8 0.026(2) 0.027(2) 0.034(3) -0.001(2) -0.0020(19) -0.0002(19) C9 0.033(3) 0.025(2) 0.037(3) -0.002(2) -0.003(2) 0.000(2) C10 0.027(2) 0.026(2) 0.037(3) -0.001(2) -0.001(2) 0.0055(19) C11 0.023(2) 0.031(2) 0.030(2) -0.0054(19) -0.0019(18) 0.0015(19) C12 0.028(2) 0.020(2) 0.035(2) -0.0023(19) -0.0004(19) 0.0019(18) C13 0.040(3) 0.031(3) 0.037(3) 0.003(2) -0.003(2) -0.001(2) C14 0.036(3) 0.033(3) 0.038(3) -0.004(2) 0.004(2) -0.002(2) C15 0.022(2) 0.021(2) 0.031(2) -0.0004(18) 0.0043(18) -0.0011(17) C16 0.025(2) 0.023(2) 0.036(3) -0.0002(19) 0.0012(19) 0.0011(18) C17 0.018(2) 0.027(2) 0.038(3) 0.000(2) -0.0036(18) -0.0021(18) C18 0.023(2) 0.020(2) 0.030(2) 0.0019(18) -0.0040(18) -0.0021(17) C19 0.024(2) 0.024(2) 0.029(2) -0.0016(18) -0.0028(18) -0.0010(18) C20 0.024(2) 0.030(2) 0.040(3) -0.002(2) -0.007(2) -0.0044(19) C21 0.030(2) 0.023(2) 0.029(2) -0.0015(19) -0.0018(19) -0.0007(19) C22 0.026(2) 0.022(2) 0.031(2) 0.0003(19) -0.0058(18) 0.0000(18) C23 0.030(3) 0.040(3) 0.040(3) 0.010(2) -0.007(2) -0.004(2) C24 0.041(3) 0.036(3) 0.036(3) 0.011(2) -0.003(2) -0.008(2) C25 0.028(2) 0.025(2) 0.034(3) -0.0004(19) -0.0005(19) -0.0011(19) C26 0.028(2) 0.025(2) 0.034(3) 0.0010(19) 0.0043(19) -0.0024(19) C27 0.041(3) 0.041(3) 0.037(3) -0.002(2) 0.007(2) -0.008(2) C28 0.028(2) 0.035(3) 0.039(3) -0.004(2) -0.001(2) 0.003(2) C29 0.031(3) 0.033(3) 0.056(3) -0.004(2) -0.005(2) -0.007(2) C30 0.030(3) 0.024(2) 0.045(3) 0.002(2) 0.000(2) 0.006(2) C31 0.030(3) 0.025(2) 0.051(3) -0.001(2) -0.001(2) 0.002(2) C32 0.029(2) 0.023(2) 0.031(2) -0.0014(19) -0.0005(19) 0.0039(19) C33 0.021(2) 0.042(3) 0.047(3) -0.008(2) -0.003(2) 0.001(2) C34 0.029(3) 0.060(4) 0.058(4) 0.002(3) 0.000(2) -0.003(3) C35 0.075(5) 0.052(4) 0.060(4) 0.010(3) -0.006(3) -0.015(3) C36 0.062(4) 0.068(4) 0.032(3) 0.001(3) -0.001(3) 0.000(3) C46 0.069(4) 0.086(5) 0.042(3) -0.001(3) -0.004(3) 0.005(4) C3 0.020(2) 0.020(2) 0.037(3) 0.0014(19) -0.0014(18) 0.0000(18) N2 0.0224(19) 0.024(2) 0.040(2) -0.0064(16) -0.0020(16) 0.0019(15) N3 0.0187(18) 0.0251(19) 0.031(2) -0.0033(16) -0.0011(15) 0.0003(15) N4 0.026(2) 0.0248(19) 0.029(2) 0.0040(16) -0.0017(15) 0.0003(15) N5 0.0233(19) 0.0241(19) 0.034(2) -0.0027(16) -0.0012(16) -0.0008(15) N6 0.0215(19) 0.0245(19) 0.033(2) -0.0020(16) 0.0013(15) 0.0020(15) Cl1 0.0230(5) 0.0250(5) 0.0460(7) 0.0049(5) -0.0040(5) 0.0008(4) Cl2 0.0730(11) 0.0654(10) 0.0558(9) -0.0103(8) -0.0182(8) 0.0027(8) Cl3 0.0906(15) 0.217(3) 0.0480(10) -0.0092(14) 0.0062(10) 0.0673(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.372(6) . ? C1 C3 1.412(6) . ? C1 C26 1.519(6) . ? C2 N1 1.363(6) . ? N1 C4 1.384(6) . ? C4 C3 1.369(6) . ? C4 C5 1.519(6) . ? C5 C8 1.516(6) . ? C5 C6 1.539(6) . ? C5 C7 1.538(6) . ? C8 C9 1.371(6) . ? C8 N2 1.379(6) . ? C9 C10 1.417(6) . ? C10 C11 1.366(6) . ? C11 N2 1.382(6) . ? C11 C12 1.531(6) . ? C12 C15 1.517(6) . ? C12 C14 1.530(6) . ? C12 C13 1.542(6) . ? C15 C16 1.372(6) . ? C15 N3 1.377(5) . ? C16 C17 1.407(6) . ? C17 C18 1.379(6) . ? C18 N3 1.384(5) . ? C18 C19 1.514(6) . ? C19 C22 1.515(6) . ? C19 C21 1.544(6) . ? C19 C20 1.544(6) . ? C22 C23 1.372(6) . ? C22 N4 1.382(5) . ? C23 C24 1.407(7) . ? C24 C25 1.360(6) . ? C25 N4 1.380(6) . ? C25 C26 1.523(6) . ? C26 C27 1.540(6) . ? C26 C28 1.542(6) . ? C29 N5 1.464(6) . ? C30 C31 1.347(6) . ? C30 N5 1.384(6) . ? C31 N6 1.375(6) . ? C32 N5 1.319(5) . ? C32 N6 1.336(6) . ? C33 N6 1.481(5) . ? C33 C34 1.519(7) . ? C34 C35 1.460(8) . ? C35 C36 1.593(8) . ? C46 Cl2 1.739(6) . ? C46 Cl3 1.746(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C3 106.5(4) . . ? C2 C1 C26 127.2(4) . . ? C3 C1 C26 126.3(4) . . ? N1 C2 C1 108.4(4) . . ? C2 N1 C4 109.8(4) . . ? C3 C4 N1 106.2(4) . . ? C3 C4 C5 128.8(4) . . ? N1 C4 C5 124.5(4) . . ? C8 C5 C4 108.7(3) . . ? C8 C5 C6 109.7(4) . . ? C4 C5 C6 109.3(4) . . ? C8 C5 C7 109.4(4) . . ? C4 C5 C7 111.0(4) . . ? C6 C5 C7 108.7(4) . . ? C9 C8 N2 106.3(4) . . ? C9 C8 C5 131.5(4) . . ? N2 C8 C5 122.2(4) . . ? C8 C9 C10 108.2(4) . . ? C11 C10 C9 108.2(4) . . ? C10 C11 N2 106.4(4) . . ? C10 C11 C12 130.5(4) . . ? N2 C11 C12 123.0(4) . . ? C15 C12 C14 108.6(4) . . ? C15 C12 C11 112.4(4) . . ? C14 C12 C11 108.0(4) . . ? C15 C12 C13 110.2(4) . . ? C14 C12 C13 108.3(4) . . ? C11 C12 C13 109.2(4) . . ? C16 C15 N3 106.7(4) . . ? C16 C15 C12 129.8(4) . . ? N3 C15 C12 123.5(4) . . ? C15 C16 C17 108.1(4) . . ? C18 C17 C16 108.5(4) . . ? C17 C18 N3 106.0(4) . . ? C17 C18 C19 130.7(4) . . ? N3 C18 C19 123.2(4) . . ? C22 C19 C18 111.2(3) . . ? C22 C19 C21 109.7(4) . . ? C18 C19 C21 110.7(4) . . ? C22 C19 C20 109.1(4) . . ? C18 C19 C20 108.3(4) . . ? C21 C19 C20 107.7(3) . . ? C23 C22 N4 106.4(4) . . ? C23 C22 C19 130.4(4) . . ? N4 C22 C19 123.3(4) . . ? C22 C23 C24 108.2(4) . . ? C25 C24 C23 108.4(4) . . ? C24 C25 N4 106.8(4) . . ? C24 C25 C26 130.5(4) . . ? N4 C25 C26 122.5(4) . . ? C1 C26 C25 111.5(4) . . ? C1 C26 C27 110.1(4) . . ? C25 C26 C27 108.8(4) . . ? C1 C26 C28 109.5(4) . . ? C25 C26 C28 108.2(4) . . ? C27 C26 C28 108.8(4) . . ? C31 C30 N5 106.1(4) . . ? C30 C31 N6 108.0(4) . . ? N5 C32 N6 108.6(4) . . ? N6 C33 C34 111.6(4) . . ? C35 C34 C33 113.6(5) . . ? C34 C35 C36 110.8(5) . . ? Cl2 C46 Cl3 113.5(3) . . ? C4 C3 C1 109.1(4) . . ? C11 N2 C8 110.8(4) . . ? C15 N3 C18 110.6(3) . . ? C25 N4 C22 110.2(4) . . ? C32 N5 C30 109.3(4) . . ? C32 N5 C29 125.5(4) . . ? C30 N5 C29 125.2(4) . . ? C32 N6 C31 108.0(4) . . ? C32 N6 C33 125.8(4) . . ? C31 N6 C33 126.1(4) . . ? 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 N2 H2A Cl1 0.88 2.53 3.404(4) 169.6 . N3 H3A Cl1 0.88 2.34 3.214(4) 174.5 . N4 H4 Cl1 0.88 2.60 3.473(4) 170.2 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.54 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.799 _refine_diff_density_min -0.754 _refine_diff_density_rms 0.076 #===END