Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 1350 _publ_requested_journal CrystEngComm loop_ _publ_author_name 'Mark E. Light' 'Gareth W. Bates' 'Philip Gale' _publ_contact_author_name 'Philip Gale' _publ_contact_author_address ; Department of Chemistry University of Southampton Southampton SO17 1BJ UNITED KINGDOM ; _publ_contact_author_email PHILIP.GALE@SOTON.AC.UK _publ_section_title ; Ionic liquid-calix[4]pyrrole complexes: pyridinium inclusion in the calixpyrrole cup ; data_2005sot0785 _database_code_depnum_ccdc_archive 'CCDC 294721' _chemical_compound_source 'Gareth Bates' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H48 Br Cl2 N5' _chemical_formula_weight 701.60 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' 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 10.441(10) _cell_length_b 16.283(15) _cell_length_c 10.634(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.42(5) _cell_angle_gamma 90.00 _cell_volume 1778(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4004 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 1.338 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8245 _exptl_absorpt_correction_T_max 0.9484 _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 15289 reflections reduced R(int) from 0.1051 to 0.0727 Ratio of minimum to maximum apparent transmission: 0.539154 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 19818 _diffrn_reflns_av_R_equivalents 0.0656 _diffrn_reflns_av_sigmaI/netI 0.1123 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7950 _reflns_number_gt 5948 _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^)+(0.0527P)^2^+0.9973P] 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 0.093(9) _refine_ls_number_reflns 7950 _refine_ls_number_parameters 406 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0924 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1247 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 N1 N 0.7184(4) 0.5517(2) 0.3263(3) 0.0160(8) Uani 1 1 d . . . H1 H 0.6549 0.5181 0.3359 0.019 Uiso 1 1 calc R . . N2 N 0.4685(4) 0.5741(2) 0.0780(3) 0.0161(8) Uani 1 1 d . . . H2 H 0.4575 0.5508 0.1500 0.019 Uiso 1 1 calc R . . N3 N 0.2778(4) 0.6570(2) 0.2721(3) 0.0167(8) Uani 1 1 d . . . H3 H 0.3070 0.6068 0.2889 0.020 Uiso 1 1 calc R . . N4 N 0.5222(4) 0.6351(2) 0.5244(3) 0.0157(8) Uani 1 1 d . . . H4 H 0.4957 0.5906 0.4804 0.019 Uiso 1 1 calc R . . C1 C 0.7870(5) 0.5995(3) 0.4222(4) 0.0157(10) Uani 1 1 d . . . C2 C 0.8777(4) 0.6442(3) 0.3682(4) 0.0166(10) Uani 1 1 d . . . H2A H 0.9386 0.6830 0.4106 0.020 Uiso 1 1 calc R . . C3 C 0.8612(5) 0.6204(3) 0.2370(4) 0.0186(10) Uani 1 1 d . . . H3A H 0.9102 0.6404 0.1764 0.022 Uiso 1 1 calc R . . C4 C 0.7626(5) 0.5635(3) 0.2132(4) 0.0175(10) Uani 1 1 d . . . C5 C 0.7013(5) 0.5200(3) 0.0922(4) 0.0175(11) Uani 1 1 d . . . C6 C 0.7993(5) 0.5166(3) -0.0008(4) 0.0244(12) Uani 1 1 d . . . H6A H 0.8256 0.5726 -0.0189 0.037 Uiso 1 1 calc R . . H6B H 0.7581 0.4902 -0.0808 0.037 Uiso 1 1 calc R . . H6C H 0.8761 0.4851 0.0382 0.037 Uiso 1 1 calc R . . C7 C 0.6624(5) 0.4307(3) 0.1178(5) 0.0201(11) Uani 1 1 d . . . H7A H 0.7379 0.4016 0.1657 0.030 Uiso 1 1 calc R . . H7B H 0.6324 0.4027 0.0362 0.030 Uiso 1 1 calc R . . H7C H 0.5921 0.4313 0.1678 0.030 Uiso 1 1 calc R . . C8 C 0.5801(4) 0.5682(3) 0.0253(4) 0.0157(10) Uani 1 1 d . . . C9 C 0.5589(5) 0.6132(3) -0.0859(4) 0.0204(11) Uani 1 1 d . . . H9 H 0.6187 0.6207 -0.1424 0.024 Uiso 1 1 calc R . . C10 C 0.4291(5) 0.6469(3) -0.1014(5) 0.0230(12) Uani 1 1 d . . . H10 H 0.3880 0.6803 -0.1702 0.028 Uiso 1 1 calc R . . C11 C 0.3761(5) 0.6221(3) 0.0004(4) 0.0169(11) Uani 1 1 d . . . C12 C 0.2386(5) 0.6379(3) 0.0303(4) 0.0188(11) Uani 1 1 d . . . C13 C 0.1588(5) 0.6839(3) -0.0833(4) 0.0233(11) Uani 1 1 d . . . H13A H 0.1530 0.6505 -0.1608 0.035 Uiso 1 1 calc R . . H13B H 0.2013 0.7363 -0.0953 0.035 Uiso 1 1 calc R . . H13C H 0.0710 0.6944 -0.0664 0.035 Uiso 1 1 calc R . . C14 C 0.1718(5) 0.5549(3) 0.0428(5) 0.0242(12) Uani 1 1 d . . . H14A H 0.2203 0.5247 0.1159 0.036 Uiso 1 1 calc R . . H14B H 0.1700 0.5229 -0.0355 0.036 Uiso 1 1 calc R . . H14C H 0.0825 0.5643 0.0561 0.036 Uiso 1 1 calc R . . C15 C 0.2409(4) 0.6898(3) 0.1492(4) 0.0169(10) Uani 1 1 d . . . C16 C 0.2022(5) 0.7684(3) 0.1641(4) 0.0244(12) Uani 1 1 d . . . H16 H 0.1718 0.8059 0.0968 0.029 Uiso 1 1 calc R . . C17 C 0.2147(5) 0.7853(3) 0.2970(4) 0.0238(12) Uani 1 1 d . . . H17 H 0.1947 0.8357 0.3342 0.029 Uiso 1 1 calc R . . C18 C 0.2618(5) 0.7141(3) 0.3624(4) 0.0166(10) Uani 1 1 d . . . C19 C 0.2944(5) 0.6977(3) 0.5052(4) 0.0184(10) Uani 1 1 d . . . C20 C 0.2309(5) 0.7671(3) 0.5754(5) 0.0236(11) Uani 1 1 d . . . H20A H 0.2650 0.8206 0.5549 0.035 Uiso 1 1 calc R . . H20B H 0.2518 0.7580 0.6679 0.035 Uiso 1 1 calc R . . H20C H 0.1362 0.7661 0.5473 0.035 Uiso 1 1 calc R . . C21 C 0.2364(5) 0.6137(3) 0.5367(4) 0.0196(10) Uani 1 1 d . . . H21A H 0.1422 0.6136 0.5050 0.029 Uiso 1 1 calc R . . H21B H 0.2534 0.6053 0.6294 0.029 Uiso 1 1 calc R . . H21C H 0.2770 0.5694 0.4954 0.029 Uiso 1 1 calc R . . C22 C 0.4420(4) 0.6979(3) 0.5536(4) 0.0158(10) Uani 1 1 d . . . C23 C 0.5189(5) 0.7555(3) 0.6232(4) 0.0192(11) Uani 1 1 d . . . H23 H 0.4902 0.8050 0.6565 0.023 Uiso 1 1 calc R . . C24 C 0.6518(5) 0.7276(3) 0.6368(4) 0.0211(11) Uani 1 1 d . . . H24 H 0.7264 0.7558 0.6807 0.025 Uiso 1 1 calc R . . C25 C 0.6520(4) 0.6542(3) 0.5762(4) 0.0148(10) Uani 1 1 d . . . C26 C 0.7638(5) 0.5975(3) 0.5587(4) 0.0195(11) Uani 1 1 d . . . C27 C 0.8887(5) 0.6263(3) 0.6502(4) 0.0228(11) Uani 1 1 d . . . H27A H 0.9091 0.6828 0.6292 0.034 Uiso 1 1 calc R . . H27B H 0.9615 0.5902 0.6406 0.034 Uiso 1 1 calc R . . H27C H 0.8743 0.6239 0.7387 0.034 Uiso 1 1 calc R . . C28 C 0.7343(5) 0.5071(3) 0.5956(5) 0.0241(11) Uani 1 1 d . . . H28A H 0.7236 0.5053 0.6852 0.036 Uiso 1 1 calc R . . H28B H 0.8069 0.4714 0.5838 0.036 Uiso 1 1 calc R . . H28C H 0.6542 0.4880 0.5408 0.036 Uiso 1 1 calc R . . C29 C 0.5982(5) 0.7747(3) 0.1721(5) 0.0218(11) Uani 1 1 d . . . H29 H 0.6074 0.7222 0.1359 0.026 Uiso 1 1 calc R . . C30 C 0.5627(5) 0.7810(3) 0.2896(5) 0.0237(11) Uani 1 1 d . . . H30 H 0.5459 0.7331 0.3348 0.028 Uiso 1 1 calc R . . C31 C 0.5518(5) 0.8580(3) 0.3417(5) 0.0279(12) Uani 1 1 d . . . H31 H 0.5306 0.8631 0.4245 0.033 Uiso 1 1 calc R . . C32 C 0.5718(5) 0.9271(3) 0.2734(5) 0.0229(11) Uani 1 1 d . . . H32 H 0.5618 0.9802 0.3073 0.028 Uiso 1 1 calc R . . C33 C 0.6061(5) 0.9184(3) 0.1560(4) 0.0233(12) Uani 1 1 d . . . H33 H 0.6204 0.9658 0.1083 0.028 Uiso 1 1 calc R . . N5 N 0.6200(4) 0.8436(2) 0.1075(3) 0.0179(9) Uani 1 1 d . . . C34 C 0.6616(6) 0.8326(4) -0.0189(5) 0.0348(15) Uani 1 1 d . . . H34A H 0.6460 0.8840 -0.0690 0.042 Uiso 1 1 calc R . . H34B H 0.6098 0.7884 -0.0676 0.042 Uiso 1 1 calc R . . C35 C 0.8044(6) 0.8109(4) 0.0012(6) 0.0483(19) Uani 1 1 d . . . H35A H 0.8547 0.8522 0.0564 0.072 Uiso 1 1 calc R . . H35B H 0.8332 0.8098 -0.0816 0.072 Uiso 1 1 calc R . . H35C H 0.8180 0.7568 0.0416 0.072 Uiso 1 1 calc R . . C37 C 0.0614(6) 0.4414(3) 0.3810(5) 0.0362(14) Uani 1 1 d . . . H37A H -0.0049 0.4856 0.3694 0.043 Uiso 1 1 calc R . . H37B H 0.1450 0.4656 0.3681 0.043 Uiso 1 1 calc R . . Cl1 Cl 0.01417(14) 0.36421(8) 0.26552(13) 0.0321(3) Uani 1 1 d . . . Cl2 Cl 0.07922(16) 0.40260(10) 0.53821(14) 0.0443(4) Uani 1 1 d . . . Br1 Br 0.41125(5) 0.46836(3) 0.33765(4) 0.02790(15) 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 N1 0.016(2) 0.020(2) 0.0135(19) 0.0030(16) 0.0056(16) -0.0018(17) N2 0.015(2) 0.021(2) 0.0129(19) 0.0017(16) 0.0057(16) 0.0006(17) N3 0.015(2) 0.018(2) 0.016(2) 0.0008(16) 0.0016(16) 0.0035(17) N4 0.022(2) 0.0127(19) 0.0131(19) -0.0007(16) 0.0052(16) -0.0016(17) C1 0.017(3) 0.012(2) 0.018(2) 0.0005(19) 0.004(2) -0.001(2) C2 0.013(2) 0.018(2) 0.018(2) 0.0011(19) 0.0013(19) -0.001(2) C3 0.018(3) 0.024(3) 0.015(2) 0.003(2) 0.007(2) 0.002(2) C4 0.019(3) 0.016(2) 0.019(2) 0.003(2) 0.005(2) 0.007(2) C5 0.015(3) 0.021(3) 0.018(2) 0.001(2) 0.008(2) 0.004(2) C6 0.016(3) 0.040(3) 0.019(2) 0.001(2) 0.005(2) 0.002(2) C7 0.019(3) 0.019(2) 0.022(3) -0.003(2) 0.002(2) 0.001(2) C8 0.013(2) 0.018(2) 0.015(2) -0.0059(19) 0.0015(18) -0.004(2) C9 0.026(3) 0.025(3) 0.011(2) 0.001(2) 0.009(2) -0.001(2) C10 0.027(3) 0.027(3) 0.015(3) 0.002(2) 0.004(2) 0.007(2) C11 0.019(3) 0.020(3) 0.012(2) -0.004(2) 0.004(2) 0.004(2) C12 0.016(3) 0.029(3) 0.011(2) -0.002(2) 0.0011(19) 0.001(2) C13 0.021(3) 0.034(3) 0.015(2) -0.003(2) 0.005(2) 0.005(2) C14 0.020(3) 0.032(3) 0.021(3) -0.007(2) 0.006(2) -0.004(2) C15 0.016(3) 0.018(2) 0.017(2) 0.0039(19) 0.006(2) 0.002(2) C16 0.026(3) 0.032(3) 0.015(2) 0.005(2) 0.003(2) 0.007(2) C17 0.039(3) 0.022(3) 0.011(2) -0.001(2) 0.004(2) 0.012(2) C18 0.018(3) 0.016(2) 0.016(2) -0.0014(19) 0.004(2) -0.001(2) C19 0.018(3) 0.017(2) 0.020(2) 0.004(2) 0.005(2) 0.006(2) C20 0.027(3) 0.027(3) 0.018(2) -0.002(2) 0.008(2) 0.009(2) C21 0.023(3) 0.021(2) 0.016(2) 0.004(2) 0.006(2) 0.006(2) C22 0.020(3) 0.016(2) 0.012(2) 0.0053(19) 0.0070(19) 0.005(2) C23 0.033(3) 0.014(2) 0.012(2) -0.0013(19) 0.008(2) 0.001(2) C24 0.029(3) 0.023(3) 0.012(2) -0.005(2) 0.009(2) -0.010(2) C25 0.013(2) 0.020(2) 0.012(2) 0.0028(19) 0.0035(18) -0.004(2) C26 0.018(3) 0.023(3) 0.019(2) -0.002(2) 0.005(2) -0.008(2) C27 0.016(3) 0.038(3) 0.013(2) 0.000(2) -0.002(2) 0.000(2) C28 0.029(3) 0.027(3) 0.018(2) 0.003(2) 0.009(2) 0.005(2) C29 0.018(3) 0.019(3) 0.030(3) 0.004(2) 0.010(2) 0.004(2) C30 0.025(3) 0.022(3) 0.024(3) 0.012(2) 0.004(2) -0.001(2) C31 0.032(3) 0.033(3) 0.020(3) 0.001(2) 0.007(2) 0.006(3) C32 0.022(3) 0.023(3) 0.025(3) -0.002(2) 0.006(2) 0.000(2) C33 0.028(3) 0.016(2) 0.026(3) 0.009(2) 0.003(2) -0.002(2) N5 0.020(2) 0.019(2) 0.015(2) 0.0062(17) 0.0055(17) -0.0003(18) C34 0.049(4) 0.039(3) 0.022(3) 0.001(3) 0.020(3) -0.003(3) C35 0.048(4) 0.062(5) 0.045(4) 0.026(3) 0.034(3) 0.026(4) C37 0.038(4) 0.027(3) 0.047(3) -0.001(2) 0.017(3) -0.007(3) Cl1 0.0270(8) 0.0322(7) 0.0370(7) -0.0040(6) 0.0053(6) 0.0015(6) Cl2 0.0412(9) 0.0521(10) 0.0377(8) 0.0003(7) 0.0020(7) -0.0082(8) Br1 0.0328(3) 0.0237(2) 0.0288(3) 0.0009(3) 0.0097(2) 0.0019(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 1.377(6) . ? N1 C4 1.377(6) . ? N2 C8 1.386(6) . ? N2 C11 1.391(6) . ? N3 C18 1.369(6) . ? N3 C15 1.400(6) . ? N4 C22 1.392(6) . ? N4 C25 1.402(6) . ? C1 C2 1.398(7) . ? C1 C26 1.515(6) . ? C2 C3 1.428(6) . ? C3 C4 1.373(7) . ? C4 C5 1.506(7) . ? C5 C7 1.547(7) . ? C5 C6 1.548(6) . ? C5 C8 1.549(7) . ? C8 C9 1.374(6) . ? C9 C10 1.444(7) . ? C10 C11 1.363(7) . ? C11 C12 1.547(7) . ? C12 C15 1.518(7) . ? C12 C13 1.533(7) . ? C12 C14 1.538(7) . ? C15 C16 1.360(7) . ? C16 C17 1.422(6) . ? C17 C18 1.395(7) . ? C18 C19 1.518(6) . ? C19 C22 1.534(7) . ? C19 C21 1.557(7) . ? C19 C20 1.566(6) . ? C22 C23 1.362(7) . ? C23 C24 1.442(7) . ? C24 C25 1.359(7) . ? C25 C26 1.527(7) . ? C26 C27 1.552(7) . ? C26 C28 1.568(7) . ? C29 N5 1.356(6) . ? C29 C30 1.370(7) . ? C30 C31 1.384(8) . ? C31 C32 1.376(7) . ? C32 C33 1.367(7) . ? C33 N5 1.341(6) . ? N5 C34 1.496(6) . ? C34 C35 1.509(8) . ? C37 Cl1 1.764(6) . ? C37 Cl2 1.765(6) . ? 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 C4 110.9(4) . . ? C8 N2 C11 110.0(4) . . ? C18 N3 C15 110.3(4) . . ? C22 N4 C25 109.1(4) . . ? N1 C1 C2 106.9(4) . . ? N1 C1 C26 123.1(4) . . ? C2 C1 C26 130.0(4) . . ? C1 C2 C3 106.8(4) . . ? C4 C3 C2 108.5(4) . . ? C3 C4 N1 107.0(4) . . ? C3 C4 C5 131.5(4) . . ? N1 C4 C5 121.5(4) . . ? C4 C5 C7 112.1(4) . . ? C4 C5 C6 109.6(4) . . ? C7 C5 C6 107.7(4) . . ? C4 C5 C8 109.8(4) . . ? C7 C5 C8 109.8(4) . . ? C6 C5 C8 107.7(4) . . ? C9 C8 N2 107.2(4) . . ? C9 C8 C5 131.1(4) . . ? N2 C8 C5 121.7(4) . . ? C8 C9 C10 107.6(4) . . ? C11 C10 C9 107.8(4) . . ? C10 C11 N2 107.5(4) . . ? C10 C11 C12 129.7(4) . . ? N2 C11 C12 122.8(4) . . ? C15 C12 C13 108.0(4) . . ? C15 C12 C14 110.9(4) . . ? C13 C12 C14 107.9(4) . . ? C15 C12 C11 112.8(4) . . ? C13 C12 C11 108.2(4) . . ? C14 C12 C11 108.9(4) . . ? C16 C15 N3 106.8(4) . . ? C16 C15 C12 131.3(4) . . ? N3 C15 C12 121.7(4) . . ? C15 C16 C17 108.8(4) . . ? C18 C17 C16 107.2(4) . . ? N3 C18 C17 106.9(4) . . ? N3 C18 C19 123.3(4) . . ? C17 C18 C19 129.8(4) . . ? C18 C19 C22 111.4(4) . . ? C18 C19 C21 110.1(4) . . ? C22 C19 C21 109.6(4) . . ? C18 C19 C20 108.2(4) . . ? C22 C19 C20 108.9(4) . . ? C21 C19 C20 108.5(4) . . ? C23 C22 N4 107.9(4) . . ? C23 C22 C19 129.9(4) . . ? N4 C22 C19 122.1(4) . . ? C22 C23 C24 107.4(4) . . ? C25 C24 C23 108.2(4) . . ? C24 C25 N4 107.3(4) . . ? C24 C25 C26 131.1(4) . . ? N4 C25 C26 121.6(4) . . ? C1 C26 C25 111.2(4) . . ? C1 C26 C27 109.4(4) . . ? C25 C26 C27 108.4(4) . . ? C1 C26 C28 109.5(4) . . ? C25 C26 C28 110.4(4) . . ? C27 C26 C28 107.9(4) . . ? N5 C29 C30 119.8(5) . . ? C29 C30 C31 119.3(5) . . ? C32 C31 C30 119.9(5) . . ? C33 C32 C31 119.2(5) . . ? N5 C33 C32 120.6(4) . . ? C33 N5 C29 121.2(4) . . ? C33 N5 C34 121.5(4) . . ? C29 N5 C34 117.3(4) . . ? N5 C34 C35 110.0(5) . . ? Cl1 C37 Cl2 111.9(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Br1 0.88 2.67 3.505(5) 158.0 . N2 H2 Br1 0.88 2.52 3.397(4) 172.2 . N3 H3 Br1 0.88 2.52 3.393(5) 174.8 . N4 H4 Br1 0.88 2.56 3.439(4) 175.5 . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.686 _refine_diff_density_min -0.649 _refine_diff_density_rms 0.093 #===END data_2005sot1057 _database_code_depnum_ccdc_archive 'CCDC 294722' _chemical_compound_source 'Gareth Bates' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H50 Cl3 N5' _chemical_formula_weight 671.17 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 10.4518(5) _cell_length_b 16.2074(8) _cell_length_c 10.5977(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.626(2) _cell_angle_gamma 90.00 _cell_volume 1769.94(13) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4187 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description Slab _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 0.293 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9145 _exptl_absorpt_correction_T_max 0.9827 _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 18668 reflections reduced R(int) from 0.0634 to 0.0489 Ratio of minimum to maximum apparent transmission: 0.814769 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 graphite _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 24884 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0770 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7902 _reflns_number_gt 6120 _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^)+(0.0979P)^2^+0.1861P] 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 -0.67(6) _refine_ls_number_reflns 7902 _refine_ls_number_parameters 415 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1582 _refine_ls_wR_factor_gt 0.1417 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.003 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 Cl3 Cl 0.92222(7) 0.80372(4) 0.84195(6) 0.01079(15) Uani 1 1 d . . . N2 N 0.9769(3) 0.70492(19) 0.5817(3) 0.0225(6) Uani 1 1 d . . . H2 H 0.9656 0.7273 0.6548 0.027 Uiso 1 1 calc R . . N5 N 1.1106(3) 0.43766(19) 0.6049(3) 0.0223(7) Uani 1 1 d . . . C4 C 1.2932(3) 0.6775(2) 0.9234(3) 0.0234(8) Uani 1 1 d . . . C11 C 1.0888(3) 0.7121(2) 0.5276(3) 0.0227(8) Uani 1 1 d . . . C1 C 1.2378(4) 0.7684(2) 1.0985(3) 0.0275(8) Uani 1 1 d . . . H1A H 1.3095 0.8045 1.0849 0.041 Uiso 1 1 calc R . . H1B H 1.2285 0.7699 1.1890 0.041 Uiso 1 1 calc R . . H1C H 1.1572 0.7876 1.0458 0.041 Uiso 1 1 calc R . . N1 N 1.2229(3) 0.72587(19) 0.8286(3) 0.0229(7) Uani 1 1 d . . . H1 H 1.1583 0.7585 0.8394 0.027 Uiso 1 1 calc R . . N4 N 1.0276(3) 0.64174(19) 1.0303(3) 0.0223(6) Uani 1 1 d . . . H4 H 1.0007 0.6871 0.9885 0.027 Uiso 1 1 calc R . . N3 N 0.7861(3) 0.62029(19) 0.7766(3) 0.0253(7) Uani 1 1 d . . . H3 H 0.8080 0.6720 0.7943 0.030 Uiso 1 1 calc R . . C14 C 0.8866(4) 0.6578(2) 0.5042(3) 0.0227(8) Uani 1 1 d . . . C32 C 1.0724(4) 0.3489(3) 0.7705(4) 0.0322(9) Uani 1 1 d . . . H32 H 1.0626 0.2946 0.8012 0.039 Uiso 1 1 calc R . . C18 C 0.7586(3) 0.5883(2) 0.6558(3) 0.0240(8) Uani 1 1 d . . . C9 C 1.2059(4) 0.7605(2) 0.5925(3) 0.0255(8) Uani 1 1 d . . . C10 C 1.3069(4) 0.7640(3) 0.5028(3) 0.0290(9) Uani 1 1 d . . . H10A H 1.3323 0.7078 0.4835 0.043 Uiso 1 1 calc R . . H10B H 1.3834 0.7945 0.5445 0.043 Uiso 1 1 calc R . . H10C H 1.2694 0.7920 0.4232 0.043 Uiso 1 1 calc R . . C24 C 0.7399(4) 0.5106(3) 1.0794(4) 0.0311(9) Uani 1 1 d . . . H24A H 0.7792 0.4574 1.0641 0.047 Uiso 1 1 calc R . . H24B H 0.6465 0.5086 1.0469 0.047 Uiso 1 1 calc R . . H24C H 0.7543 0.5221 1.1715 0.047 Uiso 1 1 calc R . . C21 C 0.7749(4) 0.5614(2) 0.8665(3) 0.0242(8) Uani 1 1 d . . . C22 C 0.7436(4) 0.6620(3) 1.0410(3) 0.0273(8) Uani 1 1 d . . . H22A H 0.7589 0.6706 1.1338 0.041 Uiso 1 1 calc R . . H22B H 0.6501 0.6619 1.0090 0.041 Uiso 1 1 calc R . . H22C H 0.7848 0.7065 0.9997 0.041 Uiso 1 1 calc R . . C31 C 1.0589(4) 0.4160(3) 0.8472(3) 0.0326(9) Uani 1 1 d . . . H31 H 1.0426 0.4083 0.9320 0.039 Uiso 1 1 calc R . . C33 C 1.0998(3) 0.3608(2) 0.6502(3) 0.0268(8) Uani 1 1 d . . . H33 H 1.1113 0.3145 0.5983 0.032 Uiso 1 1 calc R . . C7 C 1.2680(3) 0.7157(2) 0.7162(3) 0.0235(8) Uani 1 1 d . . . C34 C 1.1498(4) 0.4503(3) 0.4761(3) 0.0306(9) Uani 1 1 d . . . H34A H 1.0848 0.4854 0.4223 0.037 Uiso 1 1 calc R . . H34B H 1.1527 0.3964 0.4326 0.037 Uiso 1 1 calc R . . C30 C 1.0696(4) 0.4948(3) 0.7991(4) 0.0342(9) Uani 1 1 d . . . H30 H 1.0599 0.5420 0.8500 0.041 Uiso 1 1 calc R . . C5 C 1.3823(4) 0.6355(2) 0.8682(3) 0.0253(8) Uani 1 1 d . . . H5 H 1.4439 0.5971 0.9098 0.030 Uiso 1 1 calc R . . C26 C 1.0271(4) 0.5203(2) 1.1261(3) 0.0263(8) Uani 1 1 d . . . H26 H 0.9991 0.4702 1.1595 0.032 Uiso 1 1 calc R . . C2 C 1.2663(4) 0.6797(2) 1.0606(3) 0.0243(8) Uani 1 1 d . . . C25 C 0.9476(4) 0.5792(2) 1.0583(3) 0.0230(8) Uani 1 1 d . . . C19 C 0.7306(4) 0.5057(2) 0.6695(3) 0.0282(9) Uani 1 1 d . . . H19 H 0.7087 0.4668 0.6024 0.034 Uiso 1 1 calc R . . C29 C 1.0945(4) 0.5036(3) 0.6757(3) 0.0292(8) Uani 1 1 d . . . H29 H 1.1001 0.5573 0.6409 0.035 Uiso 1 1 calc R . . C13 C 0.9407(4) 0.6357(2) 0.3998(3) 0.0272(8) Uani 1 1 d . . . H13 H 0.9006 0.6031 0.3296 0.033 Uiso 1 1 calc R . . C12 C 1.0672(4) 0.6700(2) 0.4154(3) 0.0246(8) Uani 1 1 d . . . H12 H 1.1267 0.6646 0.3572 0.030 Uiso 1 1 calc R . . C28 C 1.1569(3) 0.6233(2) 1.0775(3) 0.0225(8) Uani 1 1 d . . . C8 C 1.1700(4) 0.8481(2) 0.6239(3) 0.0273(8) Uani 1 1 d . . . H8A H 1.1390 0.8781 0.5443 0.041 Uiso 1 1 calc R . . H8B H 1.2464 0.8761 0.6710 0.041 Uiso 1 1 calc R . . H8C H 1.1013 0.8466 0.6765 0.041 Uiso 1 1 calc R . . C6 C 1.3668(4) 0.6591(2) 0.7375(3) 0.0267(8) Uani 1 1 d . . . H6 H 1.4160 0.6393 0.6761 0.032 Uiso 1 1 calc R . . C15 C 0.6829(4) 0.7221(3) 0.5532(4) 0.0311(9) Uani 1 1 d . . . H15A H 0.7393 0.7573 0.6138 0.047 Uiso 1 1 calc R . . H15B H 0.6025 0.7107 0.5862 0.047 Uiso 1 1 calc R . . H15C H 0.6622 0.7502 0.4705 0.047 Uiso 1 1 calc R . . C16 C 0.7524(4) 0.6407(3) 0.5361(3) 0.0267(8) Uani 1 1 d . . . C17 C 0.6737(4) 0.5934(3) 0.4232(4) 0.0341(10) Uani 1 1 d . . . H17A H 0.6670 0.6268 0.3453 0.051 Uiso 1 1 calc R . . H17B H 0.5867 0.5819 0.4416 0.051 Uiso 1 1 calc R . . H17C H 0.7175 0.5413 0.4109 0.051 Uiso 1 1 calc R . . C3 C 1.3902(4) 0.6511(3) 1.1493(4) 0.0324(9) Uani 1 1 d . . . H3A H 1.4172 0.5974 1.1204 0.049 Uiso 1 1 calc R . . H3B H 1.3728 0.6462 1.2370 0.049 Uiso 1 1 calc R . . H3C H 1.4595 0.6916 1.1469 0.049 Uiso 1 1 calc R . . C20 C 0.7407(4) 0.4899(3) 0.8023(3) 0.0282(8) Uani 1 1 d . . . H20 H 0.7262 0.4384 0.8400 0.034 Uiso 1 1 calc R . . C27 C 1.1549(4) 0.5469(3) 1.1371(3) 0.0291(9) Uani 1 1 d . . . H27 H 1.2289 0.5177 1.1786 0.035 Uiso 1 1 calc R . . C23 C 0.8019(4) 0.5786(2) 1.0103(3) 0.0249(8) Uani 1 1 d . . . C35 C 1.2817(4) 0.4910(3) 0.4913(4) 0.0325(9) Uani 1 1 d . . . H35A H 1.2742 0.5476 0.5247 0.039 Uiso 1 1 calc R . . H35B H 1.3072 0.4960 0.4058 0.039 Uiso 1 1 calc R . . C36 C 1.3894(4) 0.4460(3) 0.5797(5) 0.0439(11) Uani 1 1 d . . . H36A H 1.3711 0.4471 0.6674 0.066 Uiso 1 1 calc R . . H36B H 1.4725 0.4734 0.5771 0.066 Uiso 1 1 calc R . . H36C H 1.3938 0.3887 0.5514 0.066 Uiso 1 1 calc R . . Cl1 Cl 0.52350(11) 0.91197(7) 0.75759(10) 0.0438(3) Uani 1 1 d . . . Cl2 Cl 0.57848(13) 0.87602(9) 1.03137(11) 0.0557(4) Uani 1 1 d . . . C37 C 0.5745(5) 0.8368(3) 0.8761(4) 0.0455(11) Uani 1 1 d . . . H37A H 0.5145 0.7891 0.8630 0.055 Uiso 1 1 calc R . . H37B H 0.6621 0.8170 0.8672 0.055 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 Cl3 0.0150(3) 0.0084(3) 0.0098(3) -0.0023(3) 0.0045(2) -0.0041(3) N2 0.0235(16) 0.0254(17) 0.0189(14) 0.0010(12) 0.0046(12) -0.0029(13) N5 0.0247(16) 0.0220(17) 0.0200(15) -0.0032(12) 0.0030(12) 0.0000(13) C4 0.0216(19) 0.023(2) 0.0252(19) 0.0013(15) 0.0031(14) -0.0017(15) C11 0.0228(18) 0.025(2) 0.0215(17) 0.0048(14) 0.0061(14) -0.0001(15) C1 0.027(2) 0.030(2) 0.0257(19) -0.0062(16) 0.0044(15) -0.0016(17) N1 0.0223(16) 0.0249(17) 0.0217(15) 0.0030(12) 0.0044(11) 0.0042(13) N4 0.0242(16) 0.0204(16) 0.0213(15) 0.0011(12) 0.0014(12) 0.0013(13) N3 0.0331(18) 0.0200(16) 0.0230(16) -0.0025(12) 0.0050(12) -0.0059(14) C14 0.026(2) 0.025(2) 0.0173(17) 0.0010(14) 0.0053(14) 0.0011(16) C32 0.031(2) 0.030(2) 0.034(2) 0.0042(17) 0.0005(16) 0.0004(18) C18 0.0221(18) 0.029(2) 0.0218(18) 0.0005(15) 0.0063(14) -0.0022(16) C9 0.0237(19) 0.028(2) 0.0244(19) 0.0030(15) 0.0024(15) 0.0001(16) C10 0.028(2) 0.034(2) 0.0253(19) 0.0022(16) 0.0055(15) -0.0080(17) C24 0.033(2) 0.032(2) 0.028(2) 0.0020(16) 0.0034(16) -0.0062(18) C21 0.0241(19) 0.023(2) 0.0250(19) 0.0028(15) 0.0038(14) -0.0026(16) C22 0.028(2) 0.034(2) 0.0209(18) -0.0009(15) 0.0072(14) -0.0052(17) C31 0.037(2) 0.040(2) 0.0213(18) -0.0015(17) 0.0077(16) -0.0031(19) C33 0.027(2) 0.025(2) 0.0276(19) -0.0054(15) 0.0024(15) 0.0012(16) C7 0.0227(19) 0.024(2) 0.0239(18) 0.0037(15) 0.0049(14) -0.0001(16) C34 0.035(2) 0.037(2) 0.0212(19) -0.0055(16) 0.0087(16) -0.0006(19) C30 0.034(2) 0.031(2) 0.038(2) -0.0095(18) 0.0101(17) -0.0047(19) C5 0.0246(19) 0.024(2) 0.0261(19) -0.0024(15) 0.0014(14) 0.0030(16) C26 0.037(2) 0.025(2) 0.0187(18) 0.0022(14) 0.0074(15) -0.0017(17) C2 0.0248(19) 0.027(2) 0.0200(18) -0.0023(14) 0.0011(14) 0.0004(16) C25 0.0279(19) 0.0233(19) 0.0186(17) -0.0005(14) 0.0066(14) -0.0035(16) C19 0.031(2) 0.028(2) 0.0247(19) -0.0007(16) 0.0017(15) -0.0074(18) C29 0.029(2) 0.029(2) 0.030(2) -0.0023(16) 0.0074(15) 0.0020(17) C13 0.032(2) 0.026(2) 0.0213(18) 0.0006(15) -0.0011(15) -0.0023(17) C12 0.0261(19) 0.030(2) 0.0191(17) -0.0012(15) 0.0074(14) -0.0007(16) C28 0.0259(19) 0.023(2) 0.0181(17) 0.0013(14) 0.0031(14) 0.0021(16) C8 0.030(2) 0.025(2) 0.0272(19) 0.0020(15) 0.0056(15) -0.0033(17) C6 0.0222(19) 0.030(2) 0.028(2) -0.0033(16) 0.0056(15) 0.0000(16) C15 0.028(2) 0.030(2) 0.034(2) 0.0072(17) 0.0020(16) 0.0020(17) C16 0.026(2) 0.029(2) 0.0233(18) 0.0027(15) 0.0005(15) -0.0041(17) C17 0.029(2) 0.047(3) 0.024(2) 0.0025(17) -0.0028(16) -0.0128(19) C3 0.028(2) 0.041(3) 0.026(2) 0.0010(17) -0.0011(15) 0.0012(18) C20 0.034(2) 0.026(2) 0.0249(19) -0.0002(16) 0.0046(15) -0.0039(17) C27 0.036(2) 0.032(2) 0.0189(18) 0.0001(15) 0.0006(15) 0.0098(18) C23 0.0266(19) 0.027(2) 0.0219(18) 0.0020(15) 0.0062(14) -0.0039(16) C35 0.038(2) 0.030(2) 0.031(2) -0.0015(17) 0.0118(17) -0.0045(19) C36 0.030(2) 0.045(3) 0.058(3) -0.003(2) 0.011(2) -0.007(2) Cl1 0.0390(6) 0.0425(7) 0.0483(6) 0.0032(5) 0.0022(5) -0.0064(5) Cl2 0.0531(8) 0.0661(9) 0.0462(7) -0.0026(6) 0.0035(5) 0.0054(6) C37 0.050(3) 0.036(2) 0.049(3) 0.002(2) 0.003(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 N2 C14 1.375(5) . ? N2 C11 1.391(5) . ? N5 C29 1.333(5) . ? N5 C33 1.347(5) . ? N5 C34 1.503(4) . ? C4 C5 1.362(5) . ? C4 N1 1.384(5) . ? C4 C2 1.527(5) . ? C11 C12 1.356(5) . ? C11 C9 1.519(5) . ? C1 C2 1.536(5) . ? N1 C7 1.362(5) . ? N4 C25 1.377(5) . ? N4 C28 1.393(5) . ? N3 C18 1.367(5) . ? N3 C21 1.367(5) . ? C14 C13 1.372(5) . ? C14 C16 1.522(5) . ? C32 C33 1.366(5) . ? C32 C31 1.379(6) . ? C18 C19 1.382(5) . ? C18 C16 1.520(5) . ? C9 C10 1.535(5) . ? C9 C8 1.519(5) . ? C9 C7 1.544(5) . ? C24 C23 1.527(5) . ? C21 C20 1.360(5) . ? C21 C23 1.529(5) . ? C22 C23 1.538(6) . ? C31 C30 1.387(6) . ? C7 C6 1.372(5) . ? C34 C35 1.512(6) . ? C30 C29 1.383(5) . ? C5 C6 1.420(5) . ? C26 C25 1.386(5) . ? C26 C27 1.390(6) . ? C2 C28 1.498(5) . ? C2 C3 1.539(5) . ? C25 C23 1.523(5) . ? C19 C20 1.417(5) . ? C13 C12 1.419(5) . ? C28 C27 1.391(5) . ? C15 C16 1.530(6) . ? C16 C17 1.538(5) . ? C35 C36 1.525(6) . ? Cl1 C37 1.767(5) . ? Cl2 C37 1.758(5) . ? 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 C14 N2 C11 109.9(3) . . ? C29 N5 C33 121.0(3) . . ? C29 N5 C34 118.7(3) . . ? C33 N5 C34 120.1(3) . . ? C5 C4 N1 106.8(3) . . ? C5 C4 C2 131.9(3) . . ? N1 C4 C2 121.2(3) . . ? C12 C11 N2 107.0(3) . . ? C12 C11 C9 131.3(3) . . ? N2 C11 C9 121.7(3) . . ? C7 N1 C4 110.3(3) . . ? C25 N4 C28 110.6(3) . . ? C18 N3 C21 111.0(3) . . ? C13 C14 N2 107.0(3) . . ? C13 C14 C16 130.7(3) . . ? N2 C14 C16 122.3(3) . . ? C33 C32 C31 119.9(4) . . ? N3 C18 C19 106.5(3) . . ? N3 C18 C16 122.9(3) . . ? C19 C18 C16 130.5(3) . . ? C11 C9 C10 108.9(3) . . ? C11 C9 C8 111.9(3) . . ? C10 C9 C8 108.8(3) . . ? C11 C9 C7 109.5(3) . . ? C10 C9 C7 108.0(3) . . ? C8 C9 C7 109.7(3) . . ? C20 C21 N3 107.0(3) . . ? C20 C21 C23 130.0(3) . . ? N3 C21 C23 123.0(3) . . ? C32 C31 C30 119.1(4) . . ? N5 C33 C32 120.4(4) . . ? N1 C7 C6 107.3(3) . . ? N1 C7 C9 121.9(3) . . ? C6 C7 C9 130.7(3) . . ? N5 C34 C35 110.1(3) . . ? C29 C30 C31 118.8(4) . . ? C4 C5 C6 108.0(3) . . ? C25 C26 C27 108.3(3) . . ? C28 C2 C4 111.5(3) . . ? C28 C2 C1 110.8(3) . . ? C4 C2 C1 110.2(3) . . ? C28 C2 C3 108.9(3) . . ? C4 C2 C3 107.7(3) . . ? C1 C2 C3 107.6(3) . . ? N4 C25 C26 106.6(3) . . ? N4 C25 C23 122.8(3) . . ? C26 C25 C23 130.4(3) . . ? C18 C19 C20 107.3(3) . . ? N5 C29 C30 120.7(4) . . ? C14 C13 C12 107.8(3) . . ? C11 C12 C13 108.3(3) . . ? C27 C28 N4 105.5(3) . . ? C27 C28 C2 131.9(3) . . ? N4 C28 C2 122.7(3) . . ? C7 C6 C5 107.5(3) . . ? C14 C16 C18 112.0(3) . . ? C14 C16 C15 110.1(3) . . ? C18 C16 C15 109.8(3) . . ? C14 C16 C17 108.1(3) . . ? C18 C16 C17 108.2(3) . . ? C15 C16 C17 108.6(3) . . ? C21 C20 C19 108.2(4) . . ? C28 C27 C26 109.0(3) . . ? C25 C23 C24 109.0(3) . . ? C25 C23 C21 110.0(3) . . ? C24 C23 C21 108.9(3) . . ? C25 C23 C22 109.5(3) . . ? C24 C23 C22 108.6(3) . . ? C21 C23 C22 110.9(3) . . ? C34 C35 C36 115.0(4) . . ? Cl2 C37 Cl1 111.9(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 Cl3 0.88 2.44 3.320(3) 172.9 . N1 H1 Cl3 0.88 2.58 3.411(3) 158.2 . N4 H4 Cl3 0.88 2.50 3.370(3) 171.9 . N3 H3 Cl3 0.88 2.46 3.319(3) 166.2 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.884 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.086 #===END data_2005sot1058 _database_code_depnum_ccdc_archive 'CCDC 294723' _chemical_compound_source 'Gareth Bates' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H48 Br N5' _chemical_formula_weight 630.70 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 10.6105(4) _cell_length_b 16.9689(9) _cell_length_c 18.5412(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.356(3) _cell_angle_gamma 90.00 _cell_volume 3219.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6707 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 1.310 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7696 _exptl_absorpt_correction_T_max 0.9255 _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 10917 reflections reduced R(int) from 0.0731 to 0.0588 Ratio of minimum to maximum apparent transmission: 0.640674 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 graphite _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 22995 _diffrn_reflns_av_R_equivalents 0.1101 _diffrn_reflns_av_sigmaI/netI 0.1581 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7363 _reflns_number_gt 4128 _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^)+(0.0363P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7363 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1431 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3871(3) 0.8825(2) 0.0945(2) 0.0231(9) Uani 1 1 d . . . H1A H 0.4367 0.8355 0.1159 0.035 Uiso 1 1 calc R . . H1B H 0.3864 0.8873 0.0417 0.035 Uiso 1 1 calc R . . H1C H 0.2971 0.8779 0.0985 0.035 Uiso 1 1 calc R . . C2 C 0.4516(3) 0.95627(19) 0.1375(2) 0.0205(9) Uani 1 1 d . . . C3 C 0.3686(3) 1.0285(2) 0.1062(2) 0.0263(9) Uani 1 1 d . . . H3A H 0.2799 1.0214 0.1116 0.039 Uiso 1 1 calc R . . H3B H 0.3650 1.0348 0.0531 0.039 Uiso 1 1 calc R . . H3C H 0.4078 1.0756 0.1337 0.039 Uiso 1 1 calc R . . C4 C 0.4579(3) 0.94898(19) 0.2204(2) 0.0189(8) Uani 1 1 d . . . C5 C 0.4109(3) 0.9969(2) 0.2663(2) 0.0222(9) Uani 1 1 d . . . H5 H 0.3639 1.0446 0.2522 0.027 Uiso 1 1 calc R . . C6 C 0.4443(3) 0.9629(2) 0.3387(2) 0.0237(9) Uani 1 1 d . . . H6 H 0.4232 0.9836 0.3817 0.028 Uiso 1 1 calc R . . C7 C 0.5126(3) 0.8946(2) 0.3358(2) 0.0184(8) Uani 1 1 d . . . C8 C 0.5468(4) 0.8612(2) 0.4703(2) 0.0323(10) Uani 1 1 d . . . H8A H 0.5867 0.8234 0.5097 0.048 Uiso 1 1 calc R . . H8B H 0.4521 0.8625 0.4638 0.048 Uiso 1 1 calc R . . H8C H 0.5835 0.9137 0.4844 0.048 Uiso 1 1 calc R . . C9 C 0.5751(3) 0.8360(2) 0.3969(2) 0.0214(9) Uani 1 1 d . . . C10 C 0.5169(3) 0.7533(2) 0.3762(2) 0.0269(10) Uani 1 1 d . . . H10A H 0.5301 0.7374 0.3279 0.040 Uiso 1 1 calc R . . H10B H 0.4232 0.7542 0.3728 0.040 Uiso 1 1 calc R . . H10C H 0.5606 0.7155 0.4148 0.040 Uiso 1 1 calc R . . C11 C 0.7229(3) 0.8338(2) 0.4085(2) 0.0193(8) Uani 1 1 d . . . C12 C 0.8202(3) 0.8749(2) 0.4568(2) 0.0203(9) Uani 1 1 d . . . H12 H 0.8089 0.9141 0.4912 0.024 Uiso 1 1 calc R . . C13 C 0.9413(3) 0.84870(19) 0.4465(2) 0.0198(8) Uani 1 1 d . . . H13 H 1.0254 0.8672 0.4729 0.024 Uiso 1 1 calc R . . C14 C 0.9157(3) 0.79214(19) 0.3919(2) 0.0165(8) Uani 1 1 d . . . C15 C 0.9481(3) 0.66051(19) 0.3371(2) 0.0218(9) Uani 1 1 d . . . H15A H 0.8666 0.6650 0.2973 0.033 Uiso 1 1 calc R . . H15B H 0.9301 0.6359 0.3811 0.033 Uiso 1 1 calc R . . H15C H 1.0105 0.6280 0.3196 0.033 Uiso 1 1 calc R . . C16 C 1.0065(3) 0.74331(19) 0.3579(2) 0.0179(8) Uani 1 1 d . . . C17 C 1.1380(3) 0.7328(2) 0.4170(2) 0.0212(9) Uani 1 1 d . . . H17A H 1.1971 0.7014 0.3959 0.032 Uiso 1 1 calc R . . H17B H 1.1235 0.7056 0.4608 0.032 Uiso 1 1 calc R . . H17C H 1.1770 0.7846 0.4320 0.032 Uiso 1 1 calc R . . C18 C 1.0296(3) 0.78620(19) 0.29061(19) 0.0161(8) Uani 1 1 d . . . C19 C 1.1406(3) 0.82081(19) 0.2809(2) 0.0206(8) Uani 1 1 d . . . H19 H 1.2246 0.8196 0.3154 0.025 Uiso 1 1 calc R . . C20 C 1.1078(3) 0.85879(19) 0.2102(2) 0.0197(8) Uani 1 1 d . . . H20 H 1.1662 0.8878 0.1893 0.024 Uiso 1 1 calc R . . C21 C 0.9773(3) 0.84642(19) 0.1770(2) 0.0178(8) Uani 1 1 d . . . C22 C 0.8274(3) 0.80383(19) 0.0545(2) 0.0222(9) Uani 1 1 d . . . H22A H 0.7748 0.7738 0.0811 0.033 Uiso 1 1 calc R . . H22B H 0.8958 0.7698 0.0448 0.033 Uiso 1 1 calc R . . H22C H 0.7712 0.8229 0.0069 0.033 Uiso 1 1 calc R . . C23 C 0.8914(3) 0.87502(19) 0.1030(2) 0.0181(8) Uani 1 1 d . . . C24 C 0.9770(3) 0.9187(2) 0.0614(2) 0.0244(9) Uani 1 1 d . . . H24A H 0.9224 0.9386 0.0137 0.037 Uiso 1 1 calc R . . H24B H 1.0429 0.8826 0.0519 0.037 Uiso 1 1 calc R . . H24C H 1.0206 0.9630 0.0919 0.037 Uiso 1 1 calc R . . C25 C 0.7855(3) 0.93086(19) 0.1127(2) 0.0161(8) Uani 1 1 d . . . C26 C 0.7752(3) 1.01143(19) 0.1051(2) 0.0208(9) Uani 1 1 d . . . H26 H 0.8395 1.0459 0.0955 0.025 Uiso 1 1 calc R . . C27 C 0.6511(3) 1.03392(19) 0.1141(2) 0.0204(9) Uani 1 1 d . . . H27 H 0.6181 1.0862 0.1118 0.024 Uiso 1 1 calc R . . C28 C 0.5878(3) 0.96731(19) 0.1265(2) 0.0175(8) Uani 1 1 d . . . C29 C 1.0563(4) 0.6418(2) 0.1670(2) 0.0257(9) Uani 1 1 d . . . H29 H 1.0548 0.6969 0.1577 0.031 Uiso 1 1 calc R . . C30 C 0.9415(4) 0.6023(2) 0.1621(2) 0.0317(10) Uani 1 1 d . . . H30 H 0.8607 0.6298 0.1495 0.038 Uiso 1 1 calc R . . C31 C 0.9445(4) 0.5227(2) 0.1757(2) 0.0386(11) Uani 1 1 d . . . H31 H 0.8654 0.4949 0.1724 0.046 Uiso 1 1 calc R . . C32 C 1.0618(5) 0.4833(2) 0.1942(2) 0.0398(11) Uani 1 1 d . . . H32 H 1.0646 0.4282 0.2036 0.048 Uiso 1 1 calc R . . C33 C 1.1756(4) 0.5249(2) 0.1990(2) 0.0339(10) Uani 1 1 d . . . H33 H 1.2574 0.4985 0.2124 0.041 Uiso 1 1 calc R . . C34 C 1.2914(4) 0.6470(2) 0.1803(2) 0.0365(11) Uani 1 1 d . . . H34A H 1.3703 0.6164 0.2053 0.044 Uiso 1 1 calc R . . H34B H 1.2954 0.6984 0.2061 0.044 Uiso 1 1 calc R . . C35 C 1.2872(4) 0.6599(2) 0.0990(2) 0.0319(10) Uani 1 1 d . . . H35A H 1.3677 0.6878 0.0961 0.038 Uiso 1 1 calc R . . H35B H 1.2119 0.6942 0.0758 0.038 Uiso 1 1 calc R . . C36 C 1.2757(3) 0.5836(2) 0.0546(2) 0.0313(10) Uani 1 1 d . . . H36A H 1.3535 0.5511 0.0747 0.047 Uiso 1 1 calc R . . H36B H 1.2683 0.5957 0.0020 0.047 Uiso 1 1 calc R . . H36C H 1.1977 0.5547 0.0586 0.047 Uiso 1 1 calc R . . N1 N 0.5200(3) 0.88624(16) 0.26352(17) 0.0187(7) Uani 1 1 d . . . H1 H 0.5584 0.8469 0.2469 0.022 Uiso 1 1 calc R . . N2 N 0.7818(2) 0.78387(16) 0.36869(16) 0.0184(7) Uani 1 1 d . . . H2 H 0.7400 0.7513 0.3335 0.022 Uiso 1 1 calc R . . N3 N 0.9313(2) 0.80128(14) 0.22678(16) 0.0156(7) Uani 1 1 d . . . H3 H 0.8503 0.7845 0.2188 0.019 Uiso 1 1 calc R . . N4 N 0.6709(2) 0.90498(15) 0.12691(16) 0.0174(7) Uani 1 1 d . . . H4 H 0.6535 0.8556 0.1351 0.021 Uiso 1 1 calc R . . N5 N 1.1708(3) 0.60303(17) 0.18467(17) 0.0244(7) Uani 1 1 d . . . Br1 Br 0.63043(3) 0.71653(2) 0.19048(2) 0.02020(12) 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 0.0173(18) 0.029(2) 0.023(2) -0.0017(18) 0.0048(17) -0.0023(16) C2 0.0193(18) 0.0144(19) 0.028(3) 0.0021(17) 0.0071(17) 0.0031(15) C3 0.0207(19) 0.025(2) 0.033(3) 0.0053(19) 0.0066(18) 0.0033(16) C4 0.0104(17) 0.0190(19) 0.025(2) 0.0018(17) 0.0012(16) 0.0023(15) C5 0.0167(18) 0.0158(19) 0.033(3) 0.0009(18) 0.0046(18) 0.0038(15) C6 0.0178(19) 0.023(2) 0.031(3) -0.0035(18) 0.0070(18) 0.0036(17) C7 0.0131(17) 0.025(2) 0.018(2) -0.0037(17) 0.0058(16) -0.0018(16) C8 0.027(2) 0.046(3) 0.028(3) 0.006(2) 0.0143(19) 0.0097(19) C9 0.0212(19) 0.024(2) 0.020(2) 0.0036(17) 0.0080(17) 0.0060(16) C10 0.0189(19) 0.026(2) 0.038(3) 0.0100(19) 0.0119(19) 0.0053(17) C11 0.0185(18) 0.023(2) 0.016(2) 0.0040(17) 0.0051(17) 0.0061(16) C12 0.0226(19) 0.024(2) 0.015(2) -0.0003(17) 0.0067(17) 0.0057(16) C13 0.0167(18) 0.021(2) 0.020(2) 0.0025(17) 0.0019(16) -0.0024(16) C14 0.0150(17) 0.0190(19) 0.016(2) 0.0050(17) 0.0054(15) 0.0007(15) C15 0.0223(19) 0.021(2) 0.023(2) 0.0070(17) 0.0093(17) 0.0059(16) C16 0.0146(17) 0.0196(19) 0.018(2) 0.0007(16) 0.0025(16) 0.0017(15) C17 0.0163(18) 0.026(2) 0.019(2) -0.0012(17) 0.0012(16) 0.0082(16) C18 0.0152(17) 0.0152(17) 0.018(2) 0.0008(17) 0.0045(15) 0.0019(16) C19 0.0148(18) 0.0232(19) 0.023(2) -0.0018(18) 0.0037(16) 0.0004(16) C20 0.0176(18) 0.0188(19) 0.023(2) 0.0001(17) 0.0065(17) -0.0022(16) C21 0.0187(18) 0.0135(19) 0.024(2) -0.0024(16) 0.0109(17) -0.0027(15) C22 0.0223(19) 0.026(2) 0.019(2) -0.0020(17) 0.0053(17) -0.0016(16) C23 0.0149(17) 0.0203(19) 0.019(2) -0.0022(16) 0.0051(16) -0.0034(15) C24 0.0221(19) 0.029(2) 0.022(2) 0.0056(18) 0.0070(17) -0.0009(17) C25 0.0179(18) 0.0165(19) 0.013(2) -0.0006(16) 0.0025(16) -0.0027(15) C26 0.0163(18) 0.0174(19) 0.028(2) -0.0016(17) 0.0040(17) -0.0057(15) C27 0.0224(19) 0.0127(18) 0.026(3) 0.0025(16) 0.0070(17) 0.0020(16) C28 0.0174(18) 0.0164(19) 0.017(2) 0.0018(16) 0.0014(16) 0.0032(15) C29 0.038(2) 0.016(2) 0.025(3) -0.0040(17) 0.0110(19) 0.0009(18) C30 0.036(2) 0.036(3) 0.027(3) -0.013(2) 0.016(2) -0.003(2) C31 0.057(3) 0.035(3) 0.029(3) -0.010(2) 0.020(2) -0.016(2) C32 0.078(3) 0.020(2) 0.027(3) -0.0001(19) 0.023(3) -0.008(2) C33 0.054(3) 0.026(2) 0.019(3) 0.0020(19) 0.004(2) 0.015(2) C34 0.026(2) 0.041(3) 0.037(3) -0.003(2) -0.001(2) -0.002(2) C35 0.020(2) 0.037(2) 0.037(3) 0.001(2) 0.0052(19) -0.0082(18) C36 0.023(2) 0.036(2) 0.036(3) 0.008(2) 0.0111(19) 0.0042(18) N1 0.0186(15) 0.0179(16) 0.022(2) 0.0021(14) 0.0090(14) 0.0089(13) N2 0.0151(14) 0.0215(15) 0.0191(19) -0.0040(15) 0.0053(13) -0.0011(14) N3 0.0102(14) 0.0159(16) 0.0207(19) -0.0013(13) 0.0043(13) -0.0020(12) N4 0.0187(15) 0.0104(15) 0.023(2) 0.0028(13) 0.0050(14) -0.0004(13) N5 0.0293(18) 0.0209(17) 0.022(2) 0.0004(14) 0.0044(15) 0.0017(14) Br1 0.01709(18) 0.01760(19) 0.0254(2) 0.00026(18) 0.00467(15) -0.00242(17) _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 1.543(5) . ? C2 C28 1.524(4) . ? C2 C4 1.525(5) . ? C2 C3 1.532(4) . ? C4 C5 1.363(5) . ? C4 N1 1.388(4) . ? C5 C6 1.418(5) . ? C6 C7 1.375(5) . ? C7 N1 1.371(4) . ? C7 C9 1.521(5) . ? C8 C9 1.530(5) . ? C9 C11 1.526(4) . ? C9 C10 1.540(5) . ? C11 C12 1.366(5) . ? C11 N2 1.377(4) . ? C12 C13 1.420(4) . ? C13 C14 1.370(5) . ? C14 N2 1.378(4) . ? C14 C16 1.527(4) . ? C15 C16 1.543(5) . ? C16 C18 1.520(5) . ? C16 C17 1.539(5) . ? C18 C19 1.369(4) . ? C18 N3 1.379(4) . ? C19 C20 1.419(5) . ? C20 C21 1.374(4) . ? C21 N3 1.384(4) . ? C21 C23 1.513(5) . ? C22 C23 1.551(5) . ? C23 C25 1.516(4) . ? C23 C24 1.530(4) . ? C25 C26 1.376(4) . ? C25 N4 1.382(4) . ? C26 C27 1.423(4) . ? C27 C28 1.366(4) . ? C28 N4 1.376(4) . ? C29 N5 1.344(4) . ? C29 C30 1.372(5) . ? C30 C31 1.372(5) . ? C31 C32 1.374(6) . ? C32 C33 1.381(5) . ? C33 N5 1.350(4) . ? C34 N5 1.502(4) . ? C34 C35 1.514(6) . ? C35 C36 1.522(5) . ? 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 C28 C2 C4 110.8(3) . . ? C28 C2 C3 108.7(3) . . ? C4 C2 C3 108.3(3) . . ? C28 C2 C1 109.7(3) . . ? C4 C2 C1 110.5(3) . . ? C3 C2 C1 108.8(3) . . ? C5 C4 N1 107.1(3) . . ? C5 C4 C2 130.9(3) . . ? N1 C4 C2 122.0(3) . . ? C4 C5 C6 107.9(3) . . ? C7 C6 C5 107.9(3) . . ? N1 C7 C6 107.0(3) . . ? N1 C7 C9 122.3(3) . . ? C6 C7 C9 130.7(3) . . ? C7 C9 C11 110.5(3) . . ? C7 C9 C8 109.3(3) . . ? C11 C9 C8 108.5(3) . . ? C7 C9 C10 110.1(3) . . ? C11 C9 C10 110.0(3) . . ? C8 C9 C10 108.4(3) . . ? C12 C11 N2 107.1(3) . . ? C12 C11 C9 130.5(3) . . ? N2 C11 C9 122.4(3) . . ? C11 C12 C13 107.8(3) . . ? C14 C13 C12 108.0(3) . . ? C13 C14 N2 106.8(3) . . ? C13 C14 C16 131.4(3) . . ? N2 C14 C16 121.8(3) . . ? C18 C16 C14 109.6(3) . . ? C18 C16 C17 109.1(3) . . ? C14 C16 C17 108.7(3) . . ? C18 C16 C15 111.8(3) . . ? C14 C16 C15 110.0(3) . . ? C17 C16 C15 107.5(3) . . ? C19 C18 N3 106.8(3) . . ? C19 C18 C16 130.1(3) . . ? N3 C18 C16 122.9(3) . . ? C18 C19 C20 107.9(3) . . ? C21 C20 C19 108.4(3) . . ? C20 C21 N3 106.1(3) . . ? C20 C21 C23 130.6(3) . . ? N3 C21 C23 123.2(3) . . ? C21 C23 C25 112.3(3) . . ? C21 C23 C24 108.5(3) . . ? C25 C23 C24 108.3(3) . . ? C21 C23 C22 110.0(3) . . ? C25 C23 C22 109.4(3) . . ? C24 C23 C22 108.2(3) . . ? C26 C25 N4 106.6(3) . . ? C26 C25 C23 130.5(3) . . ? N4 C25 C23 122.8(3) . . ? C25 C26 C27 107.8(3) . . ? C28 C27 C26 108.1(3) . . ? C27 C28 N4 107.1(3) . . ? C27 C28 C2 130.6(3) . . ? N4 C28 C2 122.3(3) . . ? N5 C29 C30 120.4(3) . . ? C31 C30 C29 119.5(4) . . ? C30 C31 C32 120.0(4) . . ? C31 C32 C33 119.1(4) . . ? N5 C33 C32 120.2(4) . . ? N5 C34 C35 109.0(3) . . ? C34 C35 C36 113.1(3) . . ? C7 N1 C4 110.0(3) . . ? C11 N2 C14 110.3(3) . . ? C18 N3 C21 110.8(3) . . ? C28 N4 C25 110.5(3) . . ? C29 N5 C33 120.9(3) . . ? C29 N5 C34 118.1(3) . . ? C33 N5 C34 120.7(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Br1 0.88 2.64 3.513(3) 169.4 . N2 H2 Br1 0.88 2.66 3.463(3) 151.5 . N3 H3 Br1 0.88 2.53 3.402(3) 171.3 . N4 H4 Br1 0.88 2.61 3.474(3) 167.0 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.750 _refine_diff_density_min -0.671 _refine_diff_density_rms 0.102 #===END data_2005sot1533 _database_code_depnum_ccdc_archive 'CCDC 294724' _chemical_compound_source 'Gareth Bates' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H48 Cl3 N5' _chemical_formula_weight 657.14 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 10.3713(4) _cell_length_b 16.0168(6) _cell_length_c 10.5997(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.974(2) _cell_angle_gamma 90.00 _cell_volume 1734.16(10) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4095 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 0.297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8804 _exptl_absorpt_correction_T_max 0.9853 _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 18240 reflections reduced R(int) from 0.0850 to 0.0477 Ratio of minimum to maximum apparent transmission: 0.824066 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 graphite _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 24575 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0771 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7755 _reflns_number_gt 6032 _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^)+(0.0469P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(4) _refine_ls_number_reflns 7755 _refine_ls_number_parameters 406 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.0917 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.003 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 N1 N 0.27899(19) 0.44873(12) 0.67051(16) 0.0178(4) Uani 1 1 d . . . H1 H 0.3442 0.4817 0.6601 0.021 Uiso 1 1 calc R . . N2 N 0.52890(18) 0.42921(12) 0.91647(16) 0.0163(4) Uani 1 1 d . . . H2 H 0.5395 0.4535 0.8445 0.020 Uiso 1 1 calc R . . N3 N 0.71871(18) 0.34622(12) 0.72018(16) 0.0172(4) Uani 1 1 d . . . H3 H 0.6866 0.3966 0.7025 0.021 Uiso 1 1 calc R . . N4 N 0.47439(18) 0.36529(11) 0.46962(16) 0.0160(4) Uani 1 1 d . . . H4 H 0.5006 0.4110 0.5126 0.019 Uiso 1 1 calc R . . C1 C 0.2077(2) 0.40064(14) 0.57512(19) 0.0157(5) Uani 1 1 d . . . C2 C 0.1164(2) 0.35817(15) 0.6299(2) 0.0184(5) Uani 1 1 d . . . H2A H 0.0536 0.3197 0.5878 0.022 Uiso 1 1 calc R . . C3 C 0.1326(2) 0.38205(15) 0.7612(2) 0.0188(5) Uani 1 1 d . . . H3A H 0.0821 0.3626 0.8219 0.023 Uiso 1 1 calc R . . C4 C 0.2339(2) 0.43803(14) 0.7845(2) 0.0168(5) Uani 1 1 d . . . C5 C 0.2974(2) 0.48290(14) 0.9063(2) 0.0171(5) Uani 1 1 d . . . C6 C 0.1984(2) 0.48653(16) 0.9990(2) 0.0232(6) Uani 1 1 d . . . H6A H 0.1743 0.4297 1.0199 0.035 Uiso 1 1 calc R . . H6B H 0.1199 0.5167 0.9584 0.035 Uiso 1 1 calc R . . H6C H 0.2380 0.5155 1.0777 0.035 Uiso 1 1 calc R . . C7 C 0.3331(2) 0.57302(15) 0.8768(2) 0.0192(5) Uani 1 1 d . . . H7A H 0.2551 0.6018 0.8317 0.029 Uiso 1 1 calc R . . H7B H 0.4008 0.5725 0.8229 0.029 Uiso 1 1 calc R . . H7C H 0.3661 0.6023 0.9571 0.029 Uiso 1 1 calc R . . C8 C 0.4164(2) 0.43409(14) 0.9698(2) 0.0166(5) Uani 1 1 d . . . C9 C 0.4393(2) 0.38856(15) 1.0806(2) 0.0193(5) Uani 1 1 d . . . H9 H 0.3795 0.3807 1.1381 0.023 Uiso 1 1 calc R . . C10 C 0.5676(2) 0.35518(15) 1.0948(2) 0.0210(5) Uani 1 1 d . . . H10 H 0.6088 0.3210 1.1634 0.025 Uiso 1 1 calc R . . C11 C 0.6221(2) 0.38086(15) 0.99193(19) 0.0166(5) Uani 1 1 d . . . C12 C 0.7587(2) 0.36717(15) 0.9613(2) 0.0179(5) Uani 1 1 d . . . C13 C 0.8414(3) 0.32217(17) 1.0751(2) 0.0254(6) Uani 1 1 d . . . H13A H 0.8451 0.3561 1.1525 0.038 Uiso 1 1 calc R . . H13B H 0.9302 0.3136 1.0577 0.038 Uiso 1 1 calc R . . H13C H 0.8017 0.2680 1.0878 0.038 Uiso 1 1 calc R . . C14 C 0.8238(2) 0.45228(16) 0.9450(2) 0.0232(5) Uani 1 1 d . . . H14A H 0.7695 0.4839 0.8765 0.035 Uiso 1 1 calc R . . H14B H 0.9107 0.4432 0.9230 0.035 Uiso 1 1 calc R . . H14C H 0.8325 0.4837 1.0254 0.035 Uiso 1 1 calc R . . C15 C 0.7581(2) 0.31475(15) 0.8425(2) 0.0174(5) Uani 1 1 d . . . C16 C 0.8008(2) 0.23493(16) 0.8289(2) 0.0247(6) Uani 1 1 d . . . H16 H 0.8332 0.1976 0.8966 0.030 Uiso 1 1 calc R . . C17 C 0.7880(3) 0.21769(16) 0.6956(2) 0.0255(6) Uani 1 1 d . . . H17 H 0.8107 0.1669 0.6588 0.031 Uiso 1 1 calc R . . C18 C 0.7371(2) 0.28716(15) 0.6298(2) 0.0177(5) Uani 1 1 d . . . C19 C 0.7027(2) 0.30410(14) 0.4866(2) 0.0180(5) Uani 1 1 d . . . C20 C 0.7664(3) 0.23488(15) 0.4174(2) 0.0227(6) Uani 1 1 d . . . H20A H 0.7302 0.1806 0.4359 0.034 Uiso 1 1 calc R . . H20B H 0.8612 0.2349 0.4475 0.034 Uiso 1 1 calc R . . H20C H 0.7482 0.2450 0.3249 0.034 Uiso 1 1 calc R . . C21 C 0.7594(2) 0.38924(15) 0.4545(2) 0.0207(5) Uani 1 1 d . . . H21A H 0.8541 0.3898 0.4849 0.031 Uiso 1 1 calc R . . H21B H 0.7183 0.4340 0.4966 0.031 Uiso 1 1 calc R . . H21C H 0.7415 0.3979 0.3616 0.031 Uiso 1 1 calc R . . C22 C 0.5559(2) 0.30276(15) 0.4411(2) 0.0169(5) Uani 1 1 d . . . C23 C 0.4775(2) 0.24282(15) 0.3733(2) 0.0206(5) Uani 1 1 d . . . H23 H 0.5065 0.1923 0.3405 0.025 Uiso 1 1 calc R . . C24 C 0.3461(2) 0.27008(15) 0.3612(2) 0.0209(5) Uani 1 1 d . . . H24 H 0.2712 0.2409 0.3188 0.025 Uiso 1 1 calc R . . C25 C 0.3456(2) 0.34593(15) 0.42111(19) 0.0165(5) Uani 1 1 d . . . C26 C 0.2329(2) 0.40292(15) 0.4382(2) 0.0179(5) Uani 1 1 d . . . C27 C 0.1082(2) 0.37322(18) 0.3484(2) 0.0269(6) Uani 1 1 d . . . H27A H 0.0874 0.3161 0.3711 0.040 Uiso 1 1 calc R . . H27B H 0.1229 0.3745 0.2596 0.040 Uiso 1 1 calc R . . H27C H 0.0351 0.4102 0.3574 0.040 Uiso 1 1 calc R . . C28 C 0.2621(3) 0.49315(15) 0.4017(2) 0.0229(6) Uani 1 1 d . . . H28A H 0.2747 0.4948 0.3122 0.034 Uiso 1 1 calc R . . H28B H 0.3417 0.5129 0.4573 0.034 Uiso 1 1 calc R . . H28C H 0.1884 0.5292 0.4123 0.034 Uiso 1 1 calc R . . C29 C 0.4023(2) 0.22668(16) 0.8226(2) 0.0232(6) Uani 1 1 d . . . H29 H 0.3922 0.2807 0.8568 0.028 Uiso 1 1 calc R . . C30 C 0.4360(3) 0.21852(17) 0.7039(2) 0.0257(6) Uani 1 1 d . . . H30 H 0.4483 0.2668 0.6553 0.031 Uiso 1 1 calc R . . C31 C 0.4520(2) 0.14003(17) 0.6548(2) 0.0267(6) Uani 1 1 d . . . H31 H 0.4748 0.1337 0.5723 0.032 Uiso 1 1 calc R . . C32 C 0.4344(2) 0.07102(16) 0.7277(2) 0.0248(6) Uani 1 1 d . . . H32 H 0.4467 0.0166 0.6963 0.030 Uiso 1 1 calc R . . C33 C 0.3988(2) 0.08123(15) 0.8456(2) 0.0226(6) Uani 1 1 d . . . H33 H 0.3851 0.0337 0.8952 0.027 Uiso 1 1 calc R . . N5 N 0.38350(19) 0.15820(12) 0.89115(17) 0.0198(4) Uani 1 1 d . . . C34 C 0.3392(3) 0.16978(17) 1.0165(2) 0.0310(7) Uani 1 1 d . . . H34A H 0.3523 0.1172 1.0661 0.037 Uiso 1 1 calc R . . H34B H 0.3928 0.2137 1.0663 0.037 Uiso 1 1 calc R . . C35 C 0.1984(3) 0.1940(2) 0.9982(3) 0.0489(9) Uani 1 1 d . . . H35A H 0.1457 0.1520 0.9451 0.073 Uiso 1 1 calc R . . H35B H 0.1866 0.2485 0.9556 0.073 Uiso 1 1 calc R . . H35C H 0.1704 0.1974 1.0817 0.073 Uiso 1 1 calc R . . C37 C 0.9232(3) 0.56074(18) 0.6195(2) 0.0351(7) Uani 1 1 d . . . H37A H 0.8345 0.5421 0.6296 0.042 Uiso 1 1 calc R . . H37B H 0.9816 0.5114 0.6303 0.042 Uiso 1 1 calc R . . Cl1 Cl 0.98055(7) 0.63478(4) 0.73853(6) 0.03421(17) Uani 1 1 d . . . Cl2 Cl 0.91700(8) 0.60207(5) 0.46403(7) 0.0460(2) Uani 1 1 d . . . Cl3 Cl 0.57492(5) 0.52574(3) 0.65629(5) 0.01877(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 N1 0.0163(11) 0.0218(11) 0.0160(10) 0.0006(8) 0.0045(8) -0.0052(9) N2 0.0175(11) 0.0199(11) 0.0119(9) 0.0000(8) 0.0032(8) 0.0006(8) N3 0.0210(11) 0.0146(11) 0.0159(10) -0.0001(8) 0.0025(8) 0.0046(9) N4 0.0175(11) 0.0161(11) 0.0141(9) -0.0011(8) 0.0023(8) -0.0020(9) C1 0.0162(13) 0.0150(13) 0.0150(11) 0.0023(9) 0.0005(9) 0.0023(10) C2 0.0156(13) 0.0181(13) 0.0209(12) -0.0019(10) 0.0011(9) -0.0023(10) C3 0.0186(13) 0.0223(14) 0.0168(11) 0.0028(10) 0.0065(9) -0.0001(11) C4 0.0164(13) 0.0192(13) 0.0152(11) 0.0010(10) 0.0041(9) 0.0033(10) C5 0.0161(13) 0.0199(14) 0.0158(12) -0.0009(9) 0.0044(9) 0.0009(10) C6 0.0220(14) 0.0305(15) 0.0182(12) -0.0034(11) 0.0060(10) 0.0004(11) C7 0.0188(14) 0.0187(13) 0.0204(12) -0.0029(10) 0.0041(10) 0.0027(10) C8 0.0164(13) 0.0181(13) 0.0157(11) -0.0032(9) 0.0040(9) -0.0011(10) C9 0.0210(14) 0.0220(14) 0.0162(11) 0.0011(10) 0.0067(10) -0.0015(11) C10 0.0245(15) 0.0223(14) 0.0148(12) -0.0002(10) -0.0004(10) 0.0004(11) C11 0.0186(13) 0.0186(13) 0.0120(11) -0.0021(9) 0.0013(9) 0.0033(10) C12 0.0174(13) 0.0205(14) 0.0158(11) -0.0020(10) 0.0029(9) -0.0009(10) C13 0.0207(14) 0.0339(16) 0.0201(13) -0.0019(11) -0.0006(10) 0.0056(12) C14 0.0194(14) 0.0274(14) 0.0226(12) -0.0063(10) 0.0033(10) -0.0014(11) C15 0.0166(13) 0.0207(14) 0.0153(12) 0.0019(9) 0.0040(9) -0.0008(10) C16 0.0299(16) 0.0237(15) 0.0201(13) 0.0033(10) 0.0028(10) 0.0078(12) C17 0.0373(17) 0.0196(15) 0.0196(13) -0.0006(10) 0.0049(11) 0.0061(12) C18 0.0213(14) 0.0160(13) 0.0162(12) -0.0008(9) 0.0042(9) 0.0012(10) C19 0.0216(14) 0.0167(13) 0.0163(12) -0.0002(9) 0.0044(10) 0.0038(11) C20 0.0312(15) 0.0229(14) 0.0150(12) -0.0017(10) 0.0067(10) 0.0072(12) C21 0.0215(14) 0.0245(14) 0.0167(12) 0.0001(10) 0.0050(10) 0.0005(11) C22 0.0241(14) 0.0160(13) 0.0118(11) 0.0010(9) 0.0065(9) 0.0003(10) C23 0.0287(15) 0.0164(13) 0.0185(12) -0.0027(10) 0.0090(10) 0.0011(11) C24 0.0236(14) 0.0244(14) 0.0143(12) -0.0017(10) 0.0023(10) -0.0063(11) C25 0.0187(13) 0.0217(14) 0.0100(11) 0.0022(9) 0.0046(9) -0.0021(11) C26 0.0179(13) 0.0211(14) 0.0146(11) 0.0014(10) 0.0022(9) -0.0014(11) C27 0.0225(15) 0.0420(18) 0.0152(12) -0.0023(11) 0.0006(10) -0.0017(12) C28 0.0267(15) 0.0221(14) 0.0206(12) 0.0059(10) 0.0065(10) 0.0050(11) C29 0.0234(15) 0.0181(14) 0.0289(14) 0.0031(10) 0.0069(11) -0.0016(11) C30 0.0270(15) 0.0226(15) 0.0288(14) 0.0080(11) 0.0083(11) -0.0009(11) C31 0.0282(15) 0.0331(16) 0.0197(13) 0.0004(12) 0.0065(10) 0.0018(13) C32 0.0274(15) 0.0212(14) 0.0256(13) -0.0026(11) 0.0035(11) 0.0025(12) C33 0.0250(15) 0.0178(14) 0.0241(13) 0.0046(11) 0.0017(10) -0.0010(11) N5 0.0239(12) 0.0182(12) 0.0180(10) 0.0025(8) 0.0060(8) -0.0011(9) C34 0.0424(18) 0.0306(16) 0.0231(14) 0.0012(11) 0.0147(12) -0.0019(13) C35 0.055(2) 0.050(2) 0.0501(19) 0.0158(15) 0.0336(16) 0.0208(17) C37 0.0378(18) 0.0308(16) 0.0383(16) -0.0009(12) 0.0106(13) -0.0041(13) Cl1 0.0309(4) 0.0320(4) 0.0393(4) -0.0027(3) 0.0049(3) 0.0024(3) Cl2 0.0447(5) 0.0528(5) 0.0391(4) 0.0015(3) 0.0036(3) -0.0084(4) Cl3 0.0219(3) 0.0149(3) 0.0205(3) 0.0009(2) 0.0065(2) 0.0001(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 C4 1.380(3) . ? N1 C1 1.379(3) . ? N2 C8 1.384(3) . ? N2 C11 1.380(3) . ? N3 C18 1.383(3) . ? N3 C15 1.385(3) . ? N4 C22 1.378(3) . ? N4 C25 1.381(3) . ? C1 C2 1.374(3) . ? C1 C26 1.518(3) . ? C2 C3 1.425(3) . ? C3 C4 1.371(3) . ? C4 C5 1.524(3) . ? C5 C8 1.516(3) . ? C5 C7 1.536(3) . ? C5 C6 1.540(3) . ? C8 C9 1.368(3) . ? C9 C10 1.418(3) . ? C10 C11 1.375(3) . ? C11 C12 1.524(3) . ? C12 C15 1.513(3) . ? C12 C13 1.533(3) . ? C12 C14 1.544(3) . ? C15 C16 1.368(3) . ? C16 C17 1.423(3) . ? C17 C18 1.370(3) . ? C18 C19 1.522(3) . ? C19 C22 1.516(3) . ? C19 C20 1.540(3) . ? C19 C21 1.546(3) . ? C22 C23 1.377(3) . ? C23 C24 1.416(3) . ? C24 C25 1.371(3) . ? C25 C26 1.519(3) . ? C26 C28 1.540(3) . ? C26 C27 1.542(3) . ? C29 N5 1.348(3) . ? C29 C30 1.370(3) . ? C30 C31 1.381(4) . ? C31 C32 1.379(3) . ? C32 C33 1.373(3) . ? C33 N5 1.344(3) . ? N5 C34 1.491(3) . ? C34 C35 1.491(4) . ? C37 Cl1 1.759(3) . ? C37 Cl2 1.766(3) . ? 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 C4 N1 C1 110.66(19) . . ? C8 N2 C11 110.48(18) . . ? C18 N3 C15 110.22(19) . . ? C22 N4 C25 110.23(18) . . ? C2 C1 N1 106.72(18) . . ? C2 C1 C26 131.4(2) . . ? N1 C1 C26 121.9(2) . . ? C1 C2 C3 107.9(2) . . ? C4 C3 C2 107.99(19) . . ? C3 C4 N1 106.76(18) . . ? C3 C4 C5 131.81(19) . . ? N1 C4 C5 121.4(2) . . ? C8 C5 C4 109.39(18) . . ? C8 C5 C7 111.63(19) . . ? C4 C5 C7 110.78(18) . . ? C8 C5 C6 108.52(18) . . ? C4 C5 C6 108.66(19) . . ? C7 C5 C6 107.77(18) . . ? C9 C8 N2 106.7(2) . . ? C9 C8 C5 131.5(2) . . ? N2 C8 C5 121.77(19) . . ? C8 C9 C10 108.19(19) . . ? C11 C10 C9 108.1(2) . . ? C10 C11 N2 106.6(2) . . ? C10 C11 C12 130.6(2) . . ? N2 C11 C12 122.74(19) . . ? C15 C12 C11 112.80(19) . . ? C15 C12 C13 108.36(19) . . ? C11 C12 C13 108.30(18) . . ? C15 C12 C14 109.63(18) . . ? C11 C12 C14 109.73(19) . . ? C13 C12 C14 107.9(2) . . ? C16 C15 N3 106.87(19) . . ? C16 C15 C12 130.6(2) . . ? N3 C15 C12 122.4(2) . . ? C15 C16 C17 108.0(2) . . ? C18 C17 C16 108.0(2) . . ? C17 C18 N3 106.85(19) . . ? C17 C18 C19 131.0(2) . . ? N3 C18 C19 122.2(2) . . ? C22 C19 C18 111.36(17) . . ? C22 C19 C20 109.14(19) . . ? C18 C19 C20 107.51(18) . . ? C22 C19 C21 109.95(19) . . ? C18 C19 C21 110.17(19) . . ? C20 C19 C21 108.65(18) . . ? C23 C22 N4 107.0(2) . . ? C23 C22 C19 130.2(2) . . ? N4 C22 C19 122.7(2) . . ? C22 C23 C24 107.7(2) . . ? C25 C24 C23 108.2(2) . . ? C24 C25 N4 106.9(2) . . ? C24 C25 C26 130.7(2) . . ? N4 C25 C26 122.4(2) . . ? C1 C26 C25 111.29(18) . . ? C1 C26 C28 109.68(19) . . ? C25 C26 C28 110.19(19) . . ? C1 C26 C27 108.55(18) . . ? C25 C26 C27 108.7(2) . . ? C28 C26 C27 108.3(2) . . ? N5 C29 C30 120.1(2) . . ? C29 C30 C31 119.9(2) . . ? C32 C31 C30 118.9(2) . . ? C33 C32 C31 119.8(2) . . ? N5 C33 C32 120.3(2) . . ? C33 N5 C29 121.05(19) . . ? C33 N5 C34 120.6(2) . . ? C29 N5 C34 118.3(2) . . ? C35 C34 N5 111.2(2) . . ? Cl1 C37 Cl2 111.70(15) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Cl3 0.88 2.50 3.335(2) 158.3 . N2 H2 Cl3 0.88 2.39 3.2680(18) 176.8 . N3 H3 Cl3 0.88 2.38 3.256(2) 173.2 . N4 H4 Cl3 0.88 2.43 3.3003(19) 172.4 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.233 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.055 #===END