# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Philip Gale' _publ_contact_author_email PHILIP.GALE@SOTON.AC.UK _publ_section_title ; Bis-cation salt complexation by meso-octamethylcalix[4]pyrrole: linking complexes in solution and in the solid state ; loop_ _publ_author_name 'Philip Gale' 'Nathan L. Bill' 'Claudia Caltagirone' 'Dustin E. Gross' 'Mark Light' 'Jonathan L. Sessler' # Attachment '625_670_731_new.cif' data_2007sot0625 _database_code_depnum_ccdc_archive 'CCDC 743462' _chemical_compound_source 'Claudia Caltagirone' _database_code_CSD 7SOT0625 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C28 H36 N4), C14 H18 N2, 2(C H2 Cl2), 2Br' _chemical_formula_sum 'C72 H94 Br2 Cl4 N10' _chemical_formula_weight 1401.19 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)/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 10.4058(2) _cell_length_b 19.7769(4) _cell_length_c 18.4439(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.8800(10) _cell_angle_gamma 90.00 _cell_volume 3759.81(11) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 65873 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Slab _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1468 _exptl_absorpt_coefficient_mu 1.266 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7126 _exptl_absorpt_correction_T_max 0.9511 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; ; _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 64143 _diffrn_reflns_av_R_equivalents 0.0754 _diffrn_reflns_av_sigmaI/netI 0.0588 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.48 _reflns_number_total 8589 _reflns_number_gt 6841 _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. A highly disordered DCM molecule was treated using SQUEEZE - Sluis, P. v.d. & Spek, A. L. (1990) Acta Cryst. A46, 194-201. ; _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^)+(0.0478P)^2^+3.5993P] 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 8589 _refine_ls_number_parameters 405 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1137 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.3914(2) 0.18553(14) 0.60881(13) 0.0197(5) Uani 1 1 d . . . C2 C 0.3295(3) 0.24315(14) 0.57979(14) 0.0240(6) Uani 1 1 d . . . H2 H 0.2876 0.2485 0.5310 0.029 Uiso 1 1 calc R . . C3 C 0.3398(3) 0.29303(14) 0.63575(14) 0.0241(6) Uani 1 1 d . . . H3 H 0.3055 0.3376 0.6310 0.029 Uiso 1 1 calc R . . C4 C 0.4074(2) 0.26576(14) 0.69772(13) 0.0211(5) Uani 1 1 d . . . C5 C 0.3689(3) 0.36297(15) 0.77725(15) 0.0277(6) Uani 1 1 d . . . H5A H 0.3978 0.3946 0.7419 0.041 Uiso 1 1 calc R . . H5B H 0.3874 0.3820 0.8266 0.041 Uiso 1 1 calc R . . H5C H 0.2754 0.3553 0.7651 0.041 Uiso 1 1 calc R . . C6 C 0.4411(2) 0.29567(14) 0.77421(14) 0.0223(5) Uani 1 1 d . . . C7 C 0.3941(3) 0.24717(15) 0.83038(14) 0.0251(6) Uani 1 1 d . . . H7A H 0.3014 0.2380 0.8167 0.038 Uiso 1 1 calc R . . H7B H 0.4083 0.2680 0.8791 0.038 Uiso 1 1 calc R . . H7C H 0.4428 0.2047 0.8312 0.038 Uiso 1 1 calc R . . C8 C 0.5858(2) 0.30862(14) 0.79344(13) 0.0225(6) Uani 1 1 d . . . C9 C 0.6530(3) 0.36761(15) 0.80521(15) 0.0267(6) Uani 1 1 d . . . H9 H 0.6164 0.4117 0.8021 0.032 Uiso 1 1 calc R . . C10 C 0.7872(3) 0.35222(16) 0.82295(16) 0.0305(6) Uani 1 1 d . . . H10 H 0.8556 0.3841 0.8333 0.037 Uiso 1 1 calc R . . C11 C 0.8001(3) 0.28344(15) 0.82240(14) 0.0251(6) Uani 1 1 d . . . C12 C 1.0360(3) 0.28439(19) 0.86658(17) 0.0378(8) Uani 1 1 d . . . H12A H 1.0497 0.3173 0.8286 0.057 Uiso 1 1 calc R . . H12B H 1.1140 0.2565 0.8783 0.057 Uiso 1 1 calc R . . H12C H 1.0183 0.3084 0.9106 0.057 Uiso 1 1 calc R . . C13 C 0.9202(2) 0.23897(16) 0.83871(14) 0.0266(6) Uani 1 1 d . . . C14 C 0.9021(3) 0.18720(18) 0.89906(15) 0.0351(7) Uani 1 1 d . . . H14A H 0.8927 0.2112 0.9446 0.053 Uiso 1 1 calc R . . H14B H 0.9779 0.1574 0.9071 0.053 Uiso 1 1 calc R . . H14C H 0.8241 0.1602 0.8838 0.053 Uiso 1 1 calc R . . C15 C 0.9493(2) 0.20250(14) 0.76999(14) 0.0227(6) Uani 1 1 d . . . C16 C 1.0334(2) 0.21807(14) 0.72105(14) 0.0230(6) Uani 1 1 d . . . H16 H 1.0892 0.2563 0.7234 0.028 Uiso 1 1 calc R . . C17 C 1.0223(2) 0.16693(14) 0.66617(14) 0.0223(5) Uani 1 1 d . . . H17 H 1.0693 0.1651 0.6255 0.027 Uiso 1 1 calc R . . C18 C 0.9318(2) 0.12062(14) 0.68216(14) 0.0212(5) Uani 1 1 d . . . C19 C 0.9799(3) 0.03189(16) 0.59468(16) 0.0304(6) Uani 1 1 d . . . H19A H 0.9465 -0.0085 0.5676 0.046 Uiso 1 1 calc R . . H19B H 1.0605 0.0206 0.6264 0.046 Uiso 1 1 calc R . . H19C H 0.9971 0.0672 0.5600 0.046 Uiso 1 1 calc R . . C20 C 0.8790(2) 0.05748(14) 0.64165(15) 0.0234(6) Uani 1 1 d . . . C21 C 0.8558(3) 0.00058(15) 0.69557(16) 0.0294(6) Uani 1 1 d . . . H21A H 0.7894 0.0149 0.7252 0.044 Uiso 1 1 calc R . . H21B H 0.9369 -0.0091 0.7276 0.044 Uiso 1 1 calc R . . H21C H 0.8264 -0.0403 0.6681 0.044 Uiso 1 1 calc R . . C22 C 0.7546(2) 0.07299(14) 0.59199(14) 0.0223(5) Uani 1 1 d . . . C23 C 0.7275(3) 0.07650(15) 0.51680(15) 0.0279(6) Uani 1 1 d . . . H23 H 0.7873 0.0689 0.4831 0.034 Uiso 1 1 calc R . . C24 C 0.5943(3) 0.09351(15) 0.49859(14) 0.0260(6) Uani 1 1 d . . . H24 H 0.5495 0.0991 0.4505 0.031 Uiso 1 1 calc R . . C25 C 0.5416(3) 0.10043(14) 0.56239(13) 0.0212(5) Uani 1 1 d . . . C26 C 0.3144(3) 0.11263(15) 0.50217(14) 0.0264(6) Uani 1 1 d . . . H26A H 0.2245 0.1211 0.5100 0.040 Uiso 1 1 calc R . . H26B H 0.3207 0.0677 0.4805 0.040 Uiso 1 1 calc R . . H26C H 0.3412 0.1470 0.4691 0.040 Uiso 1 1 calc R . . C27 C 0.4036(2) 0.11589(14) 0.57603(13) 0.0203(5) Uani 1 1 d . . . C28 C 0.3582(3) 0.06173(15) 0.62697(14) 0.0240(6) Uani 1 1 d . . . H28A H 0.4168 0.0612 0.6733 0.036 Uiso 1 1 calc R . . H28B H 0.3590 0.0173 0.6036 0.036 Uiso 1 1 calc R . . H28C H 0.2700 0.0722 0.6364 0.036 Uiso 1 1 calc R . . C29 C 0.6558(3) 0.33683(17) 0.61960(15) 0.0336(7) Uani 1 1 d . . . H29 H 0.6559 0.3634 0.6625 0.040 Uiso 1 1 calc R . . C30 C 0.7301(3) 0.27873(18) 0.62193(17) 0.0394(8) Uani 1 1 d . . . H30 H 0.7810 0.2652 0.6663 0.047 Uiso 1 1 calc R . . C31 C 0.7298(3) 0.24064(17) 0.55944(17) 0.0350(7) Uani 1 1 d . . . H31 H 0.7815 0.2010 0.5600 0.042 Uiso 1 1 calc R . . C32 C 0.6530(3) 0.26079(15) 0.49583(15) 0.0289(6) Uani 1 1 d . . . H32 H 0.6505 0.2347 0.4524 0.035 Uiso 1 1 calc R . . C33 C 0.5809(3) 0.31856(15) 0.49599(14) 0.0291(6) Uani 1 1 d . . . H33 H 0.5282 0.3326 0.4524 0.035 Uiso 1 1 calc R . . C34 C 0.5044(3) 0.41795(15) 0.55533(15) 0.0292(6) Uani 1 1 d . . . H34A H 0.5139 0.4384 0.6048 0.035 Uiso 1 1 calc R . . H34B H 0.4119 0.4060 0.5414 0.035 Uiso 1 1 calc R . . C35 C 0.5435(3) 0.46902(15) 0.50162(15) 0.0293(6) Uani 1 1 d . . . H35A H 0.5371 0.4483 0.4524 0.035 Uiso 1 1 calc R . . H35B H 0.6348 0.4827 0.5166 0.035 Uiso 1 1 calc R . . C36 C 0.2324(3) 0.08369(16) 0.81245(17) 0.0341(7) Uani 1 1 d . . . H36A H 0.1593 0.1079 0.7835 0.041 Uiso 1 1 calc R . . H36B H 0.3138 0.0990 0.7953 0.041 Uiso 1 1 calc R . . N1 N 0.4391(2) 0.20041(11) 0.68079(11) 0.0204(5) Uani 1 1 d . . . H1 H 0.4835 0.1721 0.7115 0.024 Uiso 1 1 calc R . . N2 N 0.6768(2) 0.25687(12) 0.80424(11) 0.0230(5) Uani 1 1 d . . . H2A H 0.6586 0.2135 0.8001 0.028 Uiso 1 1 calc R . . N3 N 0.8878(2) 0.14324(12) 0.74535(12) 0.0227(5) Uani 1 1 d . . . H3A H 0.8285 0.1226 0.7670 0.027 Uiso 1 1 calc R . . N4 N 0.6404(2) 0.08837(11) 0.61913(11) 0.0205(4) Uani 1 1 d . . . H4 H 0.6318 0.0902 0.6659 0.025 Uiso 1 1 calc R . . N5 N 0.5839(2) 0.35575(12) 0.55750(12) 0.0246(5) Uani 1 1 d . . . Br1 Br 0.59945(3) 0.085033(15) 0.806524(14) 0.02563(9) Uani 1 1 d . . . Cl1 Cl 0.23713(8) 0.10450(5) 0.90667(4) 0.0406(2) Uani 1 1 d . . . Cl2 Cl 0.21390(8) -0.00360(4) 0.79755(5) 0.0456(2) 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 0.0132(12) 0.0260(14) 0.0196(12) -0.0001(10) 0.0013(9) -0.0008(10) C2 0.0235(14) 0.0292(15) 0.0191(12) 0.0034(10) 0.0014(10) 0.0001(11) C3 0.0218(13) 0.0232(14) 0.0267(13) 0.0028(11) 0.0009(10) 0.0007(11) C4 0.0156(12) 0.0253(14) 0.0229(12) -0.0008(10) 0.0041(9) 0.0001(11) C5 0.0247(14) 0.0293(16) 0.0288(14) -0.0047(12) 0.0028(11) 0.0054(12) C6 0.0179(13) 0.0248(14) 0.0241(13) -0.0013(10) 0.0029(10) 0.0033(11) C7 0.0207(13) 0.0312(16) 0.0240(13) 0.0012(11) 0.0054(10) 0.0038(11) C8 0.0208(13) 0.0285(15) 0.0186(12) -0.0023(10) 0.0044(10) 0.0051(11) C9 0.0229(14) 0.0294(16) 0.0282(14) -0.0076(11) 0.0053(11) 0.0001(12) C10 0.0224(14) 0.0353(17) 0.0339(15) -0.0116(13) 0.0038(11) -0.0063(12) C11 0.0186(13) 0.0342(16) 0.0222(13) -0.0101(11) 0.0018(10) -0.0002(11) C12 0.0190(14) 0.055(2) 0.0389(16) -0.0218(15) 0.0014(12) -0.0024(14) C13 0.0169(13) 0.0387(17) 0.0237(13) -0.0087(12) 0.0012(10) 0.0013(12) C14 0.0269(15) 0.056(2) 0.0209(13) -0.0027(13) -0.0009(11) 0.0087(14) C15 0.0158(12) 0.0285(15) 0.0228(12) -0.0047(11) -0.0014(10) 0.0022(11) C16 0.0174(13) 0.0233(14) 0.0272(13) 0.0001(11) -0.0012(10) -0.0007(11) C17 0.0193(13) 0.0257(14) 0.0222(12) -0.0007(10) 0.0039(10) 0.0018(11) C18 0.0187(13) 0.0239(14) 0.0211(12) -0.0029(10) 0.0025(10) 0.0023(11) C19 0.0212(14) 0.0315(17) 0.0399(16) -0.0142(13) 0.0094(12) -0.0009(12) C20 0.0179(13) 0.0230(14) 0.0300(14) -0.0048(11) 0.0052(10) -0.0012(11) C21 0.0216(14) 0.0241(15) 0.0421(16) 0.0022(12) 0.0027(12) 0.0019(12) C22 0.0189(13) 0.0221(14) 0.0271(13) -0.0052(10) 0.0073(10) -0.0036(10) C23 0.0252(14) 0.0339(17) 0.0258(14) -0.0083(12) 0.0076(11) -0.0026(12) C24 0.0273(14) 0.0305(16) 0.0202(12) -0.0064(11) 0.0031(10) -0.0048(12) C25 0.0205(13) 0.0223(14) 0.0203(12) -0.0015(10) 0.0016(10) -0.0006(10) C26 0.0235(14) 0.0320(16) 0.0227(13) -0.0004(11) -0.0005(10) -0.0036(12) C27 0.0160(12) 0.0243(14) 0.0204(12) -0.0004(10) 0.0015(9) -0.0023(10) C28 0.0195(13) 0.0270(15) 0.0250(13) -0.0022(11) 0.0020(10) -0.0044(11) C29 0.0389(17) 0.0416(19) 0.0195(13) 0.0022(12) 0.0011(11) -0.0092(14) C30 0.0419(19) 0.043(2) 0.0302(16) 0.0097(14) -0.0070(13) 0.0011(15) C31 0.0310(16) 0.0309(17) 0.0424(17) 0.0080(13) 0.0029(13) 0.0002(13) C32 0.0308(15) 0.0285(16) 0.0279(14) 0.0015(11) 0.0064(11) -0.0006(12) C33 0.0350(16) 0.0320(16) 0.0197(13) 0.0016(11) 0.0021(11) -0.0006(13) C34 0.0301(15) 0.0330(16) 0.0256(14) -0.0026(12) 0.0075(11) 0.0010(13) C35 0.0324(16) 0.0284(16) 0.0285(14) -0.0052(12) 0.0092(12) -0.0044(13) C36 0.0341(16) 0.0326(17) 0.0351(16) 0.0038(13) 0.0027(12) 0.0042(14) N1 0.0194(11) 0.0228(12) 0.0181(10) 0.0011(8) -0.0004(8) 0.0044(9) N2 0.0167(11) 0.0269(13) 0.0253(11) -0.0039(9) 0.0026(8) -0.0005(9) N3 0.0182(11) 0.0271(13) 0.0236(11) -0.0029(9) 0.0055(8) -0.0030(9) N4 0.0187(11) 0.0267(12) 0.0168(10) -0.0011(9) 0.0042(8) -0.0020(9) N5 0.0230(12) 0.0293(13) 0.0212(11) 0.0006(9) 0.0023(9) -0.0048(10) Br1 0.02289(14) 0.03245(17) 0.02181(14) 0.00487(11) 0.00405(10) 0.00171(11) Cl1 0.0358(4) 0.0515(5) 0.0343(4) 0.0025(3) 0.0040(3) 0.0090(4) Cl2 0.0411(5) 0.0340(5) 0.0596(5) -0.0002(4) -0.0008(4) 0.0009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.380(4) . ? C1 N1 1.384(3) . ? C1 C27 1.516(4) . ? C2 C3 1.421(4) . ? C3 C4 1.368(4) . ? C4 N1 1.380(3) . ? C4 C6 1.526(3) . ? C5 C6 1.533(4) . ? C6 C8 1.521(4) . ? C6 C7 1.540(4) . ? C8 C9 1.362(4) . ? C8 N2 1.390(3) . ? C9 C10 1.423(4) . ? C10 C11 1.367(4) . ? C11 N2 1.385(3) . ? C11 C13 1.524(4) . ? C12 C13 1.534(4) . ? C13 C15 1.524(4) . ? C13 C14 1.543(4) . ? C15 C16 1.375(4) . ? C15 N3 1.382(4) . ? C16 C17 1.424(4) . ? C17 C18 1.374(4) . ? C18 N3 1.384(3) . ? C18 C20 1.519(4) . ? C19 C20 1.536(4) . ? C20 C22 1.511(4) . ? C20 C21 1.542(4) . ? C22 C23 1.378(4) . ? C22 N4 1.386(3) . ? C23 C24 1.421(4) . ? C24 C25 1.371(4) . ? C25 N4 1.383(3) . ? C25 C27 1.523(4) . ? C26 C27 1.541(3) . ? C27 C28 1.541(4) . ? C29 N5 1.333(4) . ? C29 C30 1.382(5) . ? C30 C31 1.376(5) . ? C31 C32 1.384(4) . ? C32 C33 1.367(4) . ? C33 N5 1.349(4) . ? C34 N5 1.480(4) . ? C34 C35 1.509(4) . ? C35 C35 1.519(6) 3_666 ? C36 Cl2 1.755(3) . ? C36 Cl1 1.780(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 C2 C1 N1 106.5(2) . . ? C2 C1 C27 130.9(2) . . ? N1 C1 C27 122.5(2) . . ? C1 C2 C3 107.9(2) . . ? C4 C3 C2 108.2(2) . . ? C3 C4 N1 107.0(2) . . ? C3 C4 C6 130.2(3) . . ? N1 C4 C6 122.7(2) . . ? C8 C6 C4 112.0(2) . . ? C8 C6 C5 108.6(2) . . ? C4 C6 C5 108.6(2) . . ? C8 C6 C7 110.1(2) . . ? C4 C6 C7 109.1(2) . . ? C5 C6 C7 108.3(2) . . ? C9 C8 N2 106.5(2) . . ? C9 C8 C6 130.7(3) . . ? N2 C8 C6 122.9(2) . . ? C8 C9 C10 108.6(3) . . ? C11 C10 C9 107.8(3) . . ? C10 C11 N2 106.9(2) . . ? C10 C11 C13 130.7(3) . . ? N2 C11 C13 122.5(3) . . ? C11 C13 C15 111.1(2) . . ? C11 C13 C12 108.3(3) . . ? C15 C13 C12 108.6(2) . . ? C11 C13 C14 110.3(2) . . ? C15 C13 C14 110.1(3) . . ? C12 C13 C14 108.4(2) . . ? C16 C15 N3 106.4(2) . . ? C16 C15 C13 131.0(3) . . ? N3 C15 C13 122.6(2) . . ? C15 C16 C17 108.1(2) . . ? C18 C17 C16 108.2(2) . . ? C17 C18 N3 106.3(2) . . ? C17 C18 C20 130.9(2) . . ? N3 C18 C20 122.7(2) . . ? C22 C20 C18 110.7(2) . . ? C22 C20 C19 108.6(2) . . ? C18 C20 C19 108.6(2) . . ? C22 C20 C21 110.0(2) . . ? C18 C20 C21 111.1(2) . . ? C19 C20 C21 107.6(2) . . ? C23 C22 N4 106.6(2) . . ? C23 C22 C20 131.3(2) . . ? N4 C22 C20 122.1(2) . . ? C22 C23 C24 107.9(2) . . ? C25 C24 C23 108.2(2) . . ? C24 C25 N4 106.8(2) . . ? C24 C25 C27 131.2(2) . . ? N4 C25 C27 122.0(2) . . ? C1 C27 C25 112.4(2) . . ? C1 C27 C26 108.5(2) . . ? C25 C27 C26 108.2(2) . . ? C1 C27 C28 109.8(2) . . ? C25 C27 C28 109.6(2) . . ? C26 C27 C28 108.2(2) . . ? N5 C29 C30 120.4(3) . . ? C31 C30 C29 119.4(3) . . ? C30 C31 C32 119.2(3) . . ? C33 C32 C31 119.5(3) . . ? N5 C33 C32 120.5(3) . . ? N5 C34 C35 111.9(2) . . ? C34 C35 C35 110.7(3) . 3_666 ? Cl2 C36 Cl1 111.60(17) . . ? C4 N1 C1 110.5(2) . . ? C11 N2 C8 110.2(2) . . ? C15 N3 C18 111.1(2) . . ? C25 N4 C22 110.5(2) . . ? C29 N5 C33 121.0(3) . . ? C29 N5 C34 120.2(2) . . ? C33 N5 C34 118.8(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Br1 0.88 2.63 3.508(2) 175.7 . N2 H2A Br1 0.88 2.62 3.494(2) 172.2 . N3 H3A Br1 0.88 2.69 3.540(2) 162.4 . N4 H4 Br1 0.88 2.66 3.540(2) 175.2 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.357 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.077 data_2007sot0670 _database_code_depnum_ccdc_archive 'CCDC 743463' _chemical_compound_source 'Claudia Caltagirone' _database_code_CSD 7SOT0670 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C72 H94 Br2 N10' _chemical_formula_weight 1259.39 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.8396(2) _cell_length_b 16.6349(3) _cell_length_c 18.3543(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.0800(10) _cell_angle_gamma 90.00 _cell_volume 3195.60(11) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7421 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1332 _exptl_absorpt_coefficient_mu 1.319 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8166 _exptl_absorpt_correction_T_max 0.9741 _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 31025 reflections reduced R(int) from 0.0922 to 0.0672 Ratio of minimum to maximum apparent transmission: 0.854667 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 36877 _diffrn_reflns_av_R_equivalents 0.0739 _diffrn_reflns_av_sigmaI/netI 0.0665 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7293 _reflns_number_gt 5430 _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^)+(0.0000P)^2^+8.4316P] 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 7293 _refine_ls_number_parameters 387 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0970 _refine_ls_R_factor_gt 0.0630 _refine_ls_wR_factor_ref 0.1200 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.147 _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 Br1 Br -0.11621(3) 0.77665(2) 0.19276(2) 0.02107(10) Uani 1 1 d . . . N1 N -0.2498(3) 0.61299(17) 0.26024(16) 0.0194(6) Uani 1 1 d . . . H901 H -0.2185 0.6563 0.2441 0.023 Uiso 1 1 calc R . . N2 N 0.0081(3) 0.70304(17) 0.37604(16) 0.0188(6) Uani 1 1 d . . . H902 H -0.0265 0.7288 0.3338 0.023 Uiso 1 1 calc R . . N3 N 0.1747(2) 0.67697(17) 0.24805(16) 0.0175(6) Uani 1 1 d . . . H903 H 0.0937 0.6909 0.2375 0.021 Uiso 1 1 calc R . . N4 N -0.0742(3) 0.58546(17) 0.13218(16) 0.0190(6) Uani 1 1 d . . . H904 H -0.0884 0.6369 0.1379 0.023 Uiso 1 1 calc R . . C1 C -0.3009(3) 0.5480(2) 0.2156(2) 0.0198(7) Uani 1 1 d . . . C2 C -0.3402(3) 0.4941(2) 0.2616(2) 0.0254(8) Uani 1 1 d . . . H2 H -0.3799 0.4436 0.2466 0.031 Uiso 1 1 calc R . . C3 C -0.3112(3) 0.5269(2) 0.3352(2) 0.0240(8) Uani 1 1 d . . . H3 H -0.3279 0.5022 0.3783 0.029 Uiso 1 1 calc R . . C4 C -0.2551(3) 0.6002(2) 0.3337(2) 0.0200(7) Uani 1 1 d . . . C5 C -0.2568(3) 0.7449(2) 0.3730(2) 0.0266(8) Uani 1 1 d . . . H5A H -0.2317 0.7619 0.3278 0.040 Uiso 1 1 calc R . . H5B H -0.2219 0.7827 0.4142 0.040 Uiso 1 1 calc R . . H5C H -0.3502 0.7442 0.3623 0.040 Uiso 1 1 calc R . . C6 C -0.2045(3) 0.6607(2) 0.3960(2) 0.0221(8) Uani 1 1 d . . . C7 C -0.2482(4) 0.6352(3) 0.4660(2) 0.0315(9) Uani 1 1 d . . . H7A H -0.3417 0.6348 0.4537 0.047 Uiso 1 1 calc R . . H7B H -0.2149 0.6733 0.5072 0.047 Uiso 1 1 calc R . . H7C H -0.2157 0.5813 0.4818 0.047 Uiso 1 1 calc R . . C8 C -0.0589(3) 0.6618(2) 0.4182(2) 0.0209(7) Uani 1 1 d . . . C9 C 0.0287(4) 0.6291(2) 0.4783(2) 0.0283(9) Uani 1 1 d . . . H9 H 0.0103 0.5967 0.5168 0.034 Uiso 1 1 calc R . . C10 C 0.1515(4) 0.6522(2) 0.4730(2) 0.0260(8) Uani 1 1 d . . . H10 H 0.2302 0.6382 0.5076 0.031 Uiso 1 1 calc R . . C11 C 0.1375(3) 0.6982(2) 0.40945(19) 0.0203(7) Uani 1 1 d . . . C12 C 0.3571(3) 0.7540(2) 0.4403(2) 0.0285(9) Uani 1 1 d . . . H12A H 0.3913 0.7013 0.4593 0.043 Uiso 1 1 calc R . . H12B H 0.3393 0.7853 0.4816 0.043 Uiso 1 1 calc R . . H12C H 0.4198 0.7826 0.4199 0.043 Uiso 1 1 calc R . . C13 C 0.2332(3) 0.7428(2) 0.3778(2) 0.0215(8) Uani 1 1 d . . . C14 C 0.1814(3) 0.8270(2) 0.3503(2) 0.0237(8) Uani 1 1 d . . . H14A H 0.2453 0.8560 0.3313 0.036 Uiso 1 1 calc R . . H14B H 0.1635 0.8569 0.3924 0.036 Uiso 1 1 calc R . . H14C H 0.1026 0.8214 0.3098 0.036 Uiso 1 1 calc R . . C15 C 0.2649(3) 0.6960(2) 0.31417(19) 0.0182(7) Uani 1 1 d . . . C16 C 0.3786(3) 0.6646(2) 0.3081(2) 0.0219(8) Uani 1 1 d . . . H16 H 0.4582 0.6686 0.3449 0.026 Uiso 1 1 calc R . . C17 C 0.3573(3) 0.6250(2) 0.2374(2) 0.0210(7) Uani 1 1 d . . . H17 H 0.4199 0.5980 0.2186 0.025 Uiso 1 1 calc R . . C18 C 0.2299(3) 0.6329(2) 0.20076(19) 0.0173(7) Uani 1 1 d . . . C19 C 0.2451(3) 0.5537(2) 0.0895(2) 0.0245(8) Uani 1 1 d . . . H19A H 0.3162 0.5870 0.0833 0.037 Uiso 1 1 calc R . . H19B H 0.1977 0.5328 0.0402 0.037 Uiso 1 1 calc R . . H19C H 0.2785 0.5087 0.1234 0.037 Uiso 1 1 calc R . . C20 C 0.1553(3) 0.6049(2) 0.12334(19) 0.0186(7) Uani 1 1 d . . . C21 C 0.1134(3) 0.6782(2) 0.0718(2) 0.0235(8) Uani 1 1 d . . . H21A H 0.0581 0.7127 0.0930 0.035 Uiso 1 1 calc R . . H21B H 0.0663 0.6601 0.0215 0.035 Uiso 1 1 calc R . . H21C H 0.1889 0.7086 0.0682 0.035 Uiso 1 1 calc R . . C22 C 0.0401(3) 0.5539(2) 0.12564(19) 0.0189(7) Uani 1 1 d . . . C23 C 0.0226(3) 0.4727(2) 0.1178(2) 0.0230(8) Uani 1 1 d . . . H23 H 0.0846 0.4348 0.1116 0.028 Uiso 1 1 calc R . . C24 C -0.1043(3) 0.4547(2) 0.1204(2) 0.0224(8) Uani 1 1 d . . . H24 H -0.1416 0.4027 0.1170 0.027 Uiso 1 1 calc R . . C25 C -0.1632(3) 0.5256(2) 0.12853(19) 0.0193(7) Uani 1 1 d . . . C26 C -0.3839(3) 0.4699(2) 0.0981(2) 0.0266(8) Uani 1 1 d . . . H26A H -0.3827 0.4641 0.0451 0.040 Uiso 1 1 calc R . . H26B H -0.4717 0.4794 0.1010 0.040 Uiso 1 1 calc R . . H26C H -0.3511 0.4207 0.1257 0.040 Uiso 1 1 calc R . . C27 C -0.2994(3) 0.5415(2) 0.1333(2) 0.0203(7) Uani 1 1 d . . . C28 C -0.3541(3) 0.6178(2) 0.0891(2) 0.0242(8) Uani 1 1 d . . . H28A H -0.3004 0.6640 0.1099 0.036 Uiso 1 1 calc R . . H28B H -0.4412 0.6270 0.0934 0.036 Uiso 1 1 calc R . . H28C H -0.3556 0.6110 0.0358 0.036 Uiso 1 1 calc R . . N5 N 0.2335(3) 0.42352(18) 0.32552(16) 0.0210(6) Uani 1 1 d . . . C29 C 0.1754(4) 0.3510(2) 0.3159(2) 0.0267(8) Uani 1 1 d . . . H29 H 0.2237 0.3039 0.3133 0.032 Uiso 1 1 calc R . . C30 C 0.0465(4) 0.3450(3) 0.3100(2) 0.0321(9) Uani 1 1 d . . . H30 H 0.0055 0.2941 0.3037 0.039 Uiso 1 1 calc R . . C31 C -0.0226(4) 0.4143(3) 0.3133(2) 0.0385(11) Uani 1 1 d . . . H31 H -0.1116 0.4112 0.3094 0.046 Uiso 1 1 calc R . . C32 C 0.0384(4) 0.4880(3) 0.3222(2) 0.0374(10) Uani 1 1 d . . . H32 H -0.0081 0.5359 0.3247 0.045 Uiso 1 1 calc R . . C33 C 0.1665(4) 0.4912(2) 0.3275(2) 0.0277(8) Uani 1 1 d . . . H33 H 0.2086 0.5417 0.3326 0.033 Uiso 1 1 calc R . . C34 C 0.3738(3) 0.4274(2) 0.3340(2) 0.0255(8) Uani 1 1 d . . . H34A H 0.3941 0.4778 0.3109 0.031 Uiso 1 1 calc R . . H34B H 0.3991 0.3819 0.3062 0.031 Uiso 1 1 calc R . . C35 C 0.4517(3) 0.4241(2) 0.4163(2) 0.0218(8) Uani 1 1 d . . . H35A H 0.4179 0.3800 0.4418 0.026 Uiso 1 1 calc R . . H35B H 0.5411 0.4106 0.4176 0.026 Uiso 1 1 calc R . . C36 C 0.4514(3) 0.5015(2) 0.46096(19) 0.0216(8) Uani 1 1 d . . . H36A H 0.3648 0.5104 0.4677 0.026 Uiso 1 1 calc R . . H36B H 0.4722 0.5473 0.4319 0.026 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 Br1 0.02132(17) 0.01671(17) 0.02429(18) 0.00131(15) 0.00434(13) -0.00045(15) N1 0.0196(14) 0.0179(15) 0.0218(16) 0.0018(12) 0.0076(12) -0.0026(12) N2 0.0182(14) 0.0221(16) 0.0150(14) 0.0032(12) 0.0023(12) -0.0014(12) N3 0.0103(13) 0.0210(15) 0.0198(15) 0.0018(12) 0.0017(11) 0.0005(11) N4 0.0192(14) 0.0153(14) 0.0230(16) -0.0037(12) 0.0066(12) -0.0003(12) C1 0.0154(16) 0.0177(17) 0.0262(19) -0.0003(15) 0.0052(14) 0.0016(14) C2 0.0207(18) 0.0181(18) 0.038(2) -0.0015(16) 0.0092(17) -0.0051(15) C3 0.0262(19) 0.0217(19) 0.029(2) 0.0030(16) 0.0154(16) -0.0025(15) C4 0.0208(17) 0.0176(17) 0.0246(19) 0.0004(15) 0.0116(15) 0.0006(14) C5 0.0233(18) 0.027(2) 0.031(2) -0.0048(16) 0.0104(16) 0.0006(15) C6 0.0245(18) 0.0213(18) 0.0236(19) -0.0007(15) 0.0115(16) -0.0021(15) C7 0.031(2) 0.037(2) 0.031(2) -0.0036(18) 0.0156(18) -0.0071(18) C8 0.0246(18) 0.0223(18) 0.0173(18) -0.0014(15) 0.0082(15) -0.0021(15) C9 0.033(2) 0.032(2) 0.023(2) 0.0060(17) 0.0110(17) -0.0001(17) C10 0.0262(18) 0.032(2) 0.0182(19) 0.0043(16) 0.0031(15) -0.0001(16) C11 0.0210(17) 0.0222(18) 0.0165(17) -0.0049(14) 0.0027(14) 0.0002(14) C12 0.0203(18) 0.038(2) 0.025(2) -0.0095(17) 0.0019(16) -0.0059(16) C13 0.0182(16) 0.0229(19) 0.0216(18) 0.0007(15) 0.0020(14) -0.0035(14) C14 0.0276(19) 0.0198(18) 0.0238(19) -0.0033(15) 0.0068(16) -0.0047(15) C15 0.0163(16) 0.0188(17) 0.0176(17) 0.0024(14) 0.0010(14) -0.0038(13) C16 0.0176(16) 0.0255(19) 0.0218(19) 0.0045(15) 0.0037(14) -0.0013(15) C17 0.0178(16) 0.0232(18) 0.0214(18) 0.0045(15) 0.0037(14) 0.0020(14) C18 0.0179(16) 0.0160(17) 0.0199(18) 0.0039(14) 0.0083(14) 0.0004(13) C19 0.0212(17) 0.030(2) 0.0228(19) -0.0003(16) 0.0064(15) 0.0025(15) C20 0.0178(16) 0.0204(18) 0.0173(17) -0.0004(14) 0.0040(14) -0.0007(14) C21 0.0224(17) 0.028(2) 0.0195(18) 0.0055(15) 0.0046(15) -0.0009(15) C22 0.0172(16) 0.0239(19) 0.0160(17) -0.0028(14) 0.0050(14) 0.0023(14) C23 0.0209(17) 0.0198(18) 0.030(2) -0.0041(15) 0.0098(16) 0.0034(14) C24 0.0221(17) 0.0187(18) 0.0249(19) -0.0032(15) 0.0035(15) -0.0038(14) C25 0.0194(17) 0.0199(18) 0.0178(17) -0.0032(14) 0.0036(14) -0.0032(14) C26 0.0186(17) 0.028(2) 0.033(2) -0.0101(17) 0.0055(16) -0.0067(15) C27 0.0156(16) 0.0211(18) 0.0240(19) -0.0015(15) 0.0051(14) -0.0018(14) C28 0.0182(17) 0.028(2) 0.0239(19) 0.0022(16) 0.0014(15) 0.0013(15) N5 0.0248(15) 0.0205(15) 0.0167(15) 0.0002(12) 0.0038(12) 0.0045(13) C29 0.033(2) 0.0213(19) 0.026(2) -0.0019(16) 0.0088(17) 0.0018(16) C30 0.029(2) 0.037(2) 0.030(2) -0.0018(18) 0.0071(18) -0.0034(18) C31 0.028(2) 0.061(3) 0.025(2) 0.001(2) 0.0035(18) 0.010(2) C32 0.036(2) 0.044(3) 0.031(2) -0.003(2) 0.0072(19) 0.022(2) C33 0.038(2) 0.0221(19) 0.023(2) 0.0033(16) 0.0081(17) 0.0097(17) C34 0.0256(19) 0.032(2) 0.0201(19) -0.0003(16) 0.0070(15) 0.0012(16) C35 0.0201(17) 0.0245(19) 0.0212(19) 0.0010(15) 0.0063(15) 0.0003(15) C36 0.0228(18) 0.0209(18) 0.0211(19) 0.0033(15) 0.0056(15) 0.0022(15) _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(4) . ? N1 C1 1.382(4) . ? N2 C8 1.376(4) . ? N2 C11 1.379(4) . ? N3 C15 1.382(4) . ? N3 C18 1.385(4) . ? N4 C25 1.375(4) . ? N4 C22 1.379(4) . ? C1 C2 1.373(5) . ? C1 C27 1.520(5) . ? C2 C3 1.415(5) . ? C3 C4 1.367(5) . ? C4 C6 1.515(5) . ? C5 C6 1.530(5) . ? C6 C8 1.524(5) . ? C6 C7 1.540(5) . ? C8 C9 1.367(5) . ? C9 C10 1.413(5) . ? C10 C11 1.371(5) . ? C11 C13 1.509(5) . ? C12 C13 1.534(5) . ? C13 C15 1.515(5) . ? C13 C14 1.544(5) . ? C15 C16 1.370(5) . ? C16 C17 1.419(5) . ? C17 C18 1.376(5) . ? C18 C20 1.514(5) . ? C19 C20 1.540(5) . ? C20 C22 1.519(5) . ? C20 C21 1.538(5) . ? C22 C23 1.367(5) . ? C23 C24 1.420(5) . ? C24 C25 1.367(5) . ? C25 C27 1.525(5) . ? C26 C27 1.538(5) . ? C27 C28 1.540(5) . ? N5 C33 1.345(5) . ? N5 C29 1.351(5) . ? N5 C34 1.490(4) . ? C29 C30 1.376(5) . ? C30 C31 1.384(6) . ? C31 C32 1.383(6) . ? C32 C33 1.367(6) . ? C34 C35 1.528(5) . ? C35 C36 1.526(5) . ? C36 C36 1.542(7) 3_666 ? 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 110.3(3) . . ? C8 N2 C11 110.2(3) . . ? C15 N3 C18 110.5(3) . . ? C25 N4 C22 110.8(3) . . ? C2 C1 N1 106.7(3) . . ? C2 C1 C27 130.5(3) . . ? N1 C1 C27 122.6(3) . . ? C1 C2 C3 107.9(3) . . ? C4 C3 C2 108.3(3) . . ? C3 C4 N1 106.8(3) . . ? C3 C4 C6 130.7(3) . . ? N1 C4 C6 122.5(3) . . ? C4 C6 C8 110.8(3) . . ? C4 C6 C5 111.3(3) . . ? C8 C6 C5 110.2(3) . . ? C4 C6 C7 108.6(3) . . ? C8 C6 C7 107.6(3) . . ? C5 C6 C7 108.1(3) . . ? C9 C8 N2 107.1(3) . . ? C9 C8 C6 131.7(3) . . ? N2 C8 C6 121.2(3) . . ? C8 C9 C10 107.8(3) . . ? C11 C10 C9 108.2(3) . . ? C10 C11 N2 106.6(3) . . ? C10 C11 C13 131.8(3) . . ? N2 C11 C13 121.5(3) . . ? C11 C13 C15 111.2(3) . . ? C11 C13 C12 109.1(3) . . ? C15 C13 C12 108.0(3) . . ? C11 C13 C14 110.1(3) . . ? C15 C13 C14 110.5(3) . . ? C12 C13 C14 107.9(3) . . ? C16 C15 N3 106.6(3) . . ? C16 C15 C13 130.4(3) . . ? N3 C15 C13 123.0(3) . . ? C15 C16 C17 108.4(3) . . ? C18 C17 C16 107.9(3) . . ? C17 C18 N3 106.6(3) . . ? C17 C18 C20 130.7(3) . . ? N3 C18 C20 122.6(3) . . ? C18 C20 C22 112.8(3) . . ? C18 C20 C21 109.4(3) . . ? C22 C20 C21 110.2(3) . . ? C18 C20 C19 108.1(3) . . ? C22 C20 C19 108.3(3) . . ? C21 C20 C19 107.9(3) . . ? C23 C22 N4 106.4(3) . . ? C23 C22 C20 129.9(3) . . ? N4 C22 C20 123.7(3) . . ? C22 C23 C24 108.3(3) . . ? C25 C24 C23 107.8(3) . . ? C24 C25 N4 106.8(3) . . ? C24 C25 C27 130.0(3) . . ? N4 C25 C27 123.2(3) . . ? C1 C27 C25 109.3(3) . . ? C1 C27 C26 108.3(3) . . ? C25 C27 C26 108.8(3) . . ? C1 C27 C28 111.2(3) . . ? C25 C27 C28 111.0(3) . . ? C26 C27 C28 108.1(3) . . ? C33 N5 C29 121.0(3) . . ? C33 N5 C34 120.3(3) . . ? C29 N5 C34 118.7(3) . . ? N5 C29 C30 120.2(4) . . ? C29 C30 C31 119.1(4) . . ? C32 C31 C30 119.7(4) . . ? C33 C32 C31 119.2(4) . . ? N5 C33 C32 120.8(4) . . ? N5 C34 C35 112.8(3) . . ? C36 C35 C34 115.1(3) . . ? C35 C36 C36 112.1(4) . 3_666 ? 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 H901 Br1 0.88 2.58 3.461(3) 175.8 . N2 H902 Br1 0.88 2.64 3.503(3) 167.1 . N3 H903 Br1 0.88 2.63 3.473(3) 160.9 . N4 H904 Br1 0.88 2.58 3.438(3) 164.4 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.532 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.100 data_2007sot0731 _database_code_depnum_ccdc_archive 'CCDC 743464' _chemical_compound_source 'Claudia Caltagirone' _database_code_CSD 7SOT0731 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C70 H96 Br2 N12' _chemical_formula_weight 1265.41 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.8915(7) _cell_length_b 16.6068(12) _cell_length_c 18.2330(11) _cell_angle_alpha 90.00 _cell_angle_beta 103.519(4) _cell_angle_gamma 90.00 _cell_volume 3206.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 99641 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1340 _exptl_absorpt_coefficient_mu 1.316 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8696 _exptl_absorpt_correction_T_max 0.9020 _exptl_absorpt_process_details ; SADABS V2.10 (Sheldrick, G.M., 2003) ; _exptl_special_details ; ; _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 31608 _diffrn_reflns_av_R_equivalents 0.1655 _diffrn_reflns_av_sigmaI/netI 0.1153 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5659 _reflns_number_gt 3813 _reflns_threshold_expression >2\s(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, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0283P)^2^+7.4552P] 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 SHELXL _refine_ls_extinction_coef 0.0042(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5659 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1118 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.1274 _refine_ls_wR_factor_gt 0.1107 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _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 Br1 Br -0.10147(4) 0.77719(3) 0.20525(3) 0.02421(17) Uani 1 1 d . . . N1 N -0.2232(3) 0.6095(2) 0.2732(2) 0.0245(9) Uani 1 1 d . . . H1 H -0.1923 0.6533 0.2573 0.029 Uiso 1 1 calc R . . N2 N 0.0293(3) 0.7017(2) 0.3859(2) 0.0241(10) Uani 1 1 d . . . H2 H -0.0070 0.7265 0.3437 0.029 Uiso 1 1 calc R . . N3 N 0.1903(3) 0.6849(2) 0.2515(2) 0.0220(9) Uani 1 1 d . . . H3 H 0.1109 0.7004 0.2421 0.026 Uiso 1 1 calc R . . N4 N -0.0563(3) 0.5900(2) 0.1394(2) 0.0232(9) Uani 1 1 d . . . H4 H -0.0696 0.6405 0.1499 0.028 Uiso 1 1 calc R . . C1 C -0.2750(4) 0.5458(3) 0.2278(3) 0.0247(11) Uani 1 1 d . . . C2 C -0.3129(5) 0.4899(3) 0.2726(3) 0.0296(12) Uani 1 1 d . . . H2A H -0.3526 0.4398 0.2570 0.035 Uiso 1 1 calc R . . C3 C -0.2818(4) 0.5208(3) 0.3471(3) 0.0286(12) Uani 1 1 d . . . H3A H -0.2970 0.4942 0.3903 0.034 Uiso 1 1 calc R . . C4 C -0.2268(4) 0.5945(3) 0.3475(3) 0.0219(11) Uani 1 1 d . . . C7 C -0.2328(5) 0.7377(3) 0.3915(3) 0.0294(12) Uani 1 1 d . . . H7A H -0.1984 0.7746 0.4332 0.044 Uiso 1 1 calc R . . H7B H -0.3249 0.7353 0.3834 0.044 Uiso 1 1 calc R . . H7C H -0.2107 0.7572 0.3455 0.044 Uiso 1 1 calc R . . C6 C -0.1767(5) 0.6528(3) 0.4109(3) 0.0269(12) Uani 1 1 d . . . C5 C -0.2173(5) 0.6231(3) 0.4816(3) 0.0343(13) Uani 1 1 d . . . H5A H -0.1841 0.5687 0.4945 0.051 Uiso 1 1 calc R . . H5B H -0.3097 0.6220 0.4716 0.051 Uiso 1 1 calc R . . H5C H -0.1840 0.6595 0.5238 0.051 Uiso 1 1 calc R . . C8 C -0.0339(4) 0.6577(3) 0.4292(3) 0.0242(11) Uani 1 1 d . . . C9 C 0.0567(5) 0.6276(3) 0.4891(3) 0.0311(12) Uani 1 1 d . . . H9 H 0.0417 0.5942 0.5284 0.037 Uiso 1 1 calc R . . C10 C 0.1759(5) 0.6555(3) 0.4813(3) 0.0286(12) Uani 1 1 d . . . H10 H 0.2550 0.6440 0.5146 0.034 Uiso 1 1 calc R . . C11 C 0.1574(4) 0.7019(3) 0.4175(3) 0.0220(11) Uani 1 1 d . . . C12 C 0.3723(4) 0.7628(3) 0.4423(3) 0.0311(13) Uani 1 1 d . . . H12A H 0.4092 0.7107 0.4608 0.047 Uiso 1 1 calc R . . H12B H 0.3548 0.7939 0.4844 0.047 Uiso 1 1 calc R . . H12C H 0.4318 0.7926 0.4196 0.047 Uiso 1 1 calc R . . C13 C 0.2477(4) 0.7489(3) 0.3822(3) 0.0258(12) Uani 1 1 d . . . C14 C 0.1920(4) 0.8321(3) 0.3563(3) 0.0273(12) Uani 1 1 d . . . H14A H 0.2525 0.8627 0.3351 0.041 Uiso 1 1 calc R . . H14B H 0.1746 0.8613 0.3995 0.041 Uiso 1 1 calc R . . H14C H 0.1133 0.8253 0.3177 0.041 Uiso 1 1 calc R . . C15 C 0.2798(4) 0.7027(3) 0.3170(3) 0.0226(11) Uani 1 1 d . . . C16 C 0.3901(4) 0.6690(3) 0.3092(3) 0.0270(12) Uani 1 1 d . . . H16 H 0.4685 0.6716 0.3453 0.032 Uiso 1 1 calc R . . C17 C 0.3685(4) 0.6296(3) 0.2383(3) 0.0247(11) Uani 1 1 d . . . H17 H 0.4298 0.6015 0.2187 0.030 Uiso 1 1 calc R . . C18 C 0.2425(4) 0.6392(3) 0.2029(2) 0.0200(11) Uani 1 1 d . . . C19 C 0.2595(5) 0.5650(3) 0.0885(3) 0.0293(12) Uani 1 1 d . . . H19A H 0.3326 0.5984 0.0862 0.044 Uiso 1 1 calc R . . H19B H 0.2150 0.5494 0.0374 0.044 Uiso 1 1 calc R . . H19C H 0.2880 0.5165 0.1183 0.044 Uiso 1 1 calc R . . C20 C 0.1696(4) 0.6130(3) 0.1259(2) 0.0230(11) Uani 1 1 d . . . C21 C 0.1281(4) 0.6884(3) 0.0771(3) 0.0270(12) Uani 1 1 d . . . H21A H 0.0688 0.7198 0.0986 0.041 Uiso 1 1 calc R . . H21B H 0.0868 0.6720 0.0256 0.041 Uiso 1 1 calc R . . H21C H 0.2023 0.7214 0.0761 0.041 Uiso 1 1 calc R . . C22 C 0.0561(4) 0.5604(3) 0.1273(3) 0.0258(12) Uani 1 1 d . . . C23 C 0.0368(5) 0.4798(3) 0.1127(3) 0.0289(12) Uani 1 1 d . . . H23 H 0.0969 0.4431 0.1017 0.035 Uiso 1 1 calc R . . C24 C -0.0884(4) 0.4607(3) 0.1167(3) 0.0280(12) Uani 1 1 d . . . H24 H -0.1262 0.4088 0.1095 0.034 Uiso 1 1 calc R . . C25 C -0.1448(4) 0.5289(3) 0.1328(3) 0.0241(11) Uani 1 1 d . . . C26 C -0.3637(5) 0.4723(3) 0.1085(3) 0.0354(13) Uani 1 1 d . . . H26A H -0.3286 0.4220 0.1327 0.053 Uiso 1 1 calc R . . H26B H -0.3678 0.4694 0.0543 0.053 Uiso 1 1 calc R . . H26C H -0.4488 0.4804 0.1163 0.053 Uiso 1 1 calc R . . C27 C -0.2785(4) 0.5433(3) 0.1432(3) 0.0258(12) Uani 1 1 d . . . C28 C -0.3356(4) 0.6209(3) 0.1031(3) 0.0290(12) Uani 1 1 d . . . H28A H -0.4223 0.6275 0.1089 0.043 Uiso 1 1 calc R . . H28B H -0.3362 0.6174 0.0494 0.043 Uiso 1 1 calc R . . H28C H -0.2847 0.6673 0.1255 0.043 Uiso 1 1 calc R . . N5 N 0.2371(3) 0.4316(2) 0.3261(2) 0.0219(9) Uani 1 1 d . . . N6 N 0.0454(4) 0.3880(2) 0.3096(2) 0.0259(10) Uani 1 1 d . . . C29 C 0.1644(4) 0.3669(3) 0.3114(3) 0.0251(11) Uani 1 1 d . . . H29 H 0.1923 0.3141 0.3035 0.030 Uiso 1 1 calc R . . C30 C -0.0643(5) 0.3331(3) 0.2951(3) 0.0369(13) Uani 1 1 d . . . H30A H -0.0397 0.2809 0.2779 0.055 Uiso 1 1 calc R . . H30B H -0.1326 0.3563 0.2561 0.055 Uiso 1 1 calc R . . H30C H -0.0933 0.3257 0.3416 0.055 Uiso 1 1 calc R . . C32 C 0.0427(4) 0.4692(3) 0.3233(3) 0.0271(12) Uani 1 1 d . . . H32 H -0.0296 0.5004 0.3252 0.033 Uiso 1 1 calc R . . C33 C 0.1622(5) 0.4962(3) 0.3337(3) 0.0282(12) Uani 1 1 d . . . H33 H 0.1897 0.5501 0.3443 0.034 Uiso 1 1 calc R . . C34 C 0.3751(4) 0.4323(3) 0.3323(3) 0.0258(11) Uani 1 1 d . . . H34A H 0.3977 0.4824 0.3091 0.031 Uiso 1 1 calc R . . H34B H 0.3974 0.3863 0.3035 0.031 Uiso 1 1 calc R . . C35 C 0.4528(4) 0.4273(3) 0.4136(2) 0.0239(11) Uani 1 1 d . . . H35A H 0.4193 0.3825 0.4390 0.029 Uiso 1 1 calc R . . H35B H 0.5408 0.4136 0.4126 0.029 Uiso 1 1 calc R . . C36 C 0.4550(4) 0.5032(3) 0.4611(2) 0.0221(11) Uani 1 1 d . . . H36A H 0.3687 0.5139 0.4673 0.027 Uiso 1 1 calc R . . H36B H 0.4807 0.5494 0.4338 0.027 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 Br1 0.0213(3) 0.0214(3) 0.0295(3) 0.0015(2) 0.00505(18) 0.0010(2) N1 0.024(2) 0.021(2) 0.030(2) 0.0021(18) 0.0097(18) -0.0051(18) N2 0.020(2) 0.028(3) 0.024(2) 0.0051(17) 0.0046(17) -0.0011(17) N3 0.016(2) 0.023(2) 0.025(2) -0.0012(18) 0.0006(17) 0.0020(17) N4 0.021(2) 0.016(2) 0.033(2) -0.0053(18) 0.0074(17) 0.0008(17) C1 0.015(2) 0.028(3) 0.031(3) -0.003(2) 0.005(2) 0.003(2) C2 0.026(3) 0.021(3) 0.043(3) 0.001(2) 0.012(2) -0.004(2) C3 0.025(3) 0.032(3) 0.031(3) 0.002(2) 0.012(2) -0.003(2) C4 0.018(2) 0.023(3) 0.027(3) 0.004(2) 0.011(2) 0.000(2) C7 0.026(3) 0.031(3) 0.034(3) -0.001(2) 0.011(2) -0.001(2) C6 0.031(3) 0.024(3) 0.029(3) 0.002(2) 0.013(2) 0.001(2) C5 0.031(3) 0.043(4) 0.032(3) -0.002(3) 0.013(2) -0.002(3) C8 0.028(3) 0.024(3) 0.024(3) -0.001(2) 0.012(2) 0.003(2) C9 0.031(3) 0.034(3) 0.028(3) 0.004(2) 0.007(2) 0.001(2) C10 0.027(3) 0.033(3) 0.024(3) 0.006(2) 0.004(2) 0.004(2) C11 0.022(3) 0.019(3) 0.024(3) -0.003(2) 0.004(2) 0.000(2) C12 0.027(3) 0.036(3) 0.028(3) -0.002(2) 0.002(2) -0.009(2) C13 0.021(3) 0.030(3) 0.025(3) 0.000(2) 0.003(2) -0.002(2) C14 0.027(3) 0.026(3) 0.030(3) -0.002(2) 0.009(2) -0.006(2) C15 0.018(2) 0.022(3) 0.026(3) 0.009(2) 0.003(2) -0.004(2) C16 0.018(3) 0.037(3) 0.025(3) 0.004(2) 0.004(2) -0.003(2) C17 0.018(3) 0.028(3) 0.030(3) 0.002(2) 0.009(2) 0.003(2) C18 0.017(2) 0.023(3) 0.020(2) 0.002(2) 0.0053(19) -0.002(2) C19 0.028(3) 0.031(3) 0.032(3) -0.005(2) 0.011(2) 0.000(2) C20 0.020(3) 0.029(3) 0.020(2) -0.001(2) 0.004(2) 0.003(2) C21 0.020(3) 0.034(3) 0.026(3) 0.004(2) 0.004(2) -0.003(2) C22 0.020(3) 0.030(3) 0.027(3) 0.001(2) 0.005(2) 0.003(2) C23 0.027(3) 0.029(3) 0.029(3) 0.000(2) 0.005(2) 0.004(2) C24 0.025(3) 0.024(3) 0.033(3) -0.002(2) 0.005(2) -0.002(2) C25 0.022(3) 0.028(3) 0.022(3) -0.004(2) 0.006(2) -0.002(2) C26 0.027(3) 0.040(4) 0.039(3) -0.012(3) 0.008(2) -0.009(3) C27 0.016(2) 0.029(3) 0.032(3) -0.003(2) 0.005(2) -0.003(2) C28 0.020(3) 0.035(3) 0.032(3) 0.000(2) 0.007(2) 0.002(2) N5 0.021(2) 0.021(2) 0.024(2) 0.0005(17) 0.0056(17) 0.0012(18) N6 0.024(2) 0.024(3) 0.028(2) -0.0022(18) 0.0028(18) -0.0014(19) C29 0.025(3) 0.020(3) 0.029(3) 0.000(2) 0.003(2) 0.003(2) C30 0.028(3) 0.039(4) 0.043(3) -0.007(3) 0.008(2) -0.010(3) C32 0.021(3) 0.030(3) 0.027(3) -0.003(2) 0.000(2) 0.001(2) C33 0.032(3) 0.024(3) 0.028(3) -0.004(2) 0.004(2) 0.004(2) C34 0.021(3) 0.031(3) 0.027(3) 0.000(2) 0.008(2) 0.005(2) C35 0.022(3) 0.024(3) 0.026(3) 0.001(2) 0.007(2) 0.002(2) C36 0.018(2) 0.022(3) 0.026(3) -0.001(2) 0.004(2) -0.004(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.379(6) . ? N1 C4 1.387(6) . ? N2 C8 1.374(6) . ? N2 C11 1.380(6) . ? N3 C15 1.385(6) . ? N3 C18 1.385(6) . ? N4 C22 1.384(6) . ? N4 C25 1.385(6) . ? C1 C2 1.363(7) . ? C1 C27 1.534(6) . ? C2 C3 1.417(7) . ? C3 C4 1.362(7) . ? C4 C6 1.508(7) . ? C7 C6 1.546(7) . ? C6 C8 1.515(7) . ? C6 C5 1.539(7) . ? C8 C9 1.382(6) . ? C9 C10 1.416(7) . ? C10 C11 1.370(6) . ? C11 C13 1.513(7) . ? C12 C13 1.549(6) . ? C13 C15 1.523(7) . ? C13 C14 1.538(7) . ? C15 C16 1.362(7) . ? C16 C17 1.418(7) . ? C17 C18 1.383(6) . ? C18 C20 1.507(6) . ? C19 C20 1.540(6) . ? C20 C22 1.518(7) . ? C20 C21 1.541(6) . ? C22 C23 1.372(7) . ? C23 C24 1.419(7) . ? C24 C25 1.353(7) . ? C25 C27 1.531(6) . ? C26 C27 1.542(7) . ? C27 C28 1.540(7) . ? N5 C29 1.324(6) . ? N5 C33 1.374(6) . ? N5 C34 1.481(6) . ? N6 C29 1.335(6) . ? N6 C32 1.372(6) . ? N6 C30 1.477(6) . ? C32 C33 1.347(7) . ? C34 C35 1.527(6) . ? C35 C36 1.526(6) . ? C36 C36 1.529(8) 3_666 ? 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 110.4(4) . . ? C8 N2 C11 110.7(4) . . ? C15 N3 C18 110.9(4) . . ? C22 N4 C25 110.5(4) . . ? C2 C1 N1 107.5(4) . . ? C2 C1 C27 130.1(5) . . ? N1 C1 C27 122.3(4) . . ? C1 C2 C3 106.8(5) . . ? C4 C3 C2 109.7(4) . . ? C3 C4 N1 105.6(4) . . ? C3 C4 C6 131.3(4) . . ? N1 C4 C6 123.1(4) . . ? C4 C6 C8 111.9(4) . . ? C4 C6 C5 108.2(4) . . ? C8 C6 C5 108.3(4) . . ? C4 C6 C7 110.9(4) . . ? C8 C6 C7 109.4(4) . . ? C5 C6 C7 108.0(4) . . ? N2 C8 C9 106.6(4) . . ? N2 C8 C6 121.9(4) . . ? C9 C8 C6 131.4(4) . . ? C8 C9 C10 107.7(4) . . ? C11 C10 C9 108.2(4) . . ? C10 C11 N2 106.7(4) . . ? C10 C11 C13 132.1(4) . . ? N2 C11 C13 121.1(4) . . ? C11 C13 C15 111.3(4) . . ? C11 C13 C14 110.2(4) . . ? C15 C13 C14 111.0(4) . . ? C11 C13 C12 109.0(4) . . ? C15 C13 C12 107.7(4) . . ? C14 C13 C12 107.5(4) . . ? C16 C15 N3 106.4(4) . . ? C16 C15 C13 131.1(4) . . ? N3 C15 C13 122.5(4) . . ? C15 C16 C17 108.8(4) . . ? C18 C17 C16 107.8(4) . . ? C17 C18 N3 106.0(4) . . ? C17 C18 C20 130.6(4) . . ? N3 C18 C20 123.3(4) . . ? C18 C20 C22 113.9(4) . . ? C18 C20 C19 108.1(4) . . ? C22 C20 C19 108.2(4) . . ? C18 C20 C21 108.8(4) . . ? C22 C20 C21 110.3(4) . . ? C19 C20 C21 107.3(4) . . ? C23 C22 N4 106.0(4) . . ? C23 C22 C20 130.3(4) . . ? N4 C22 C20 123.5(4) . . ? C22 C23 C24 108.3(5) . . ? C25 C24 C23 108.3(5) . . ? C24 C25 N4 106.9(4) . . ? C24 C25 C27 130.6(5) . . ? N4 C25 C27 122.5(4) . . ? C25 C27 C1 109.2(4) . . ? C25 C27 C28 111.2(4) . . ? C1 C27 C28 111.6(4) . . ? C25 C27 C26 109.1(4) . . ? C1 C27 C26 107.8(4) . . ? C28 C27 C26 107.9(4) . . ? C29 N5 C33 108.2(4) . . ? C29 N5 C34 124.8(4) . . ? C33 N5 C34 127.0(4) . . ? C29 N6 C32 108.4(4) . . ? C29 N6 C30 125.6(4) . . ? C32 N6 C30 126.0(4) . . ? N5 C29 N6 108.8(4) . . ? C33 C32 N6 106.9(4) . . ? C32 C33 N5 107.6(5) . . ? N5 C34 C35 113.3(4) . . ? C36 C35 C34 115.9(4) . . ? C35 C36 C36 113.1(5) . 3_666 ? 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 2.56 3.438(4) 177.3 . N2 H2 Br1 0.88 2.63 3.500(4) 169.4 . N3 H3 Br1 0.88 2.59 3.451(4) 166.6 . N4 H4 Br1 0.88 2.54 3.410(4) 169.3 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.423 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.085