# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Jan Kotek' _publ_contact_author_address ; Department of Inorganic Chemistry Charles University Hlavova 2030 Prague 12843 CZECH REPUBLIC ; _publ_contact_author_email MODREJ@NATUR.CUNI.CZ _publ_section_title ; Unsymmetrically substituted side-bridged cyclam derivatives and their Cu(II) and Zn(II) complexes ; loop_ _publ_author_name 'Jan Kotek' 'Jana Havlickova' 'Petr Hermann' 'Ivan Lukes' 'Jan Plutnar' data_pled _database_code_depnum_ccdc_archive 'CCDC 652360' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H31 Br Cu N5 O2, F6 P' _chemical_formula_sum 'C19 H31 Br Cu F6 N5 O2 P' _chemical_formula_weight 649.91 _chemical_compound_source 'synthesized by the authors' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9960(4) _cell_length_b 10.2570(8) _cell_length_c 17.8780(15) _cell_angle_alpha 73.592(3) _cell_angle_beta 84.539(5) _cell_angle_gamma 80.636(4) _cell_volume 1212.60(16) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 9051 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.47 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.780 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 658 _exptl_absorpt_coefficient_mu 2.688 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _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 9051 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0695 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5090 _reflns_number_gt 3452 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.2000P)^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 SHELXL _refine_ls_extinction_coef 0.32(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5090 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2134 _refine_ls_R_factor_gt 0.1759 _refine_ls_wR_factor_ref 0.5043 _refine_ls_wR_factor_gt 0.4889 _refine_ls_goodness_of_fit_ref 1.973 _refine_ls_restrained_S_all 1.973 _refine_ls_shift/su_max 0.002 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5076(3) 0.4085(2) 0.75798(14) 0.0710(10) Uani 1 1 d . . . Br1A Br 0.1381(7) 0.4825(9) 0.7092(6) 0.061(2) Uani 0.59(2) 1 d P . . Br1B Br 0.1021(9) 0.5324(9) 0.6679(9) 0.054(3) Uani 0.41(2) 1 d P . . N1 N 0.4414(15) 0.2569(10) 0.8582(6) 0.035(2) Uani 1 1 d . . . C2 C 0.370(2) 0.1317(16) 0.8516(9) 0.050(3) Uani 1 1 d . . . H21 H 0.2333 0.1541 0.8405 0.060 Uiso 1 1 calc R . . H22 H 0.3814 0.0620 0.9012 0.060 Uiso 1 1 calc R . . C3 C 0.480(3) 0.0739(15) 0.7880(9) 0.058(4) Uani 1 1 d . . . H31 H 0.6109 0.0394 0.8051 0.069 Uiso 1 1 calc R . . H32 H 0.4219 -0.0053 0.7873 0.069 Uiso 1 1 calc R . . C4 C 0.498(2) 0.1518(16) 0.7108(10) 0.059(4) Uani 1 1 d . . . H41 H 0.3693 0.1858 0.6918 0.070 Uiso 1 1 calc R . . H42 H 0.5631 0.0920 0.6799 0.070 Uiso 1 1 calc R . . N5 N 0.6089(14) 0.2736(11) 0.6966(7) 0.041(3) Uani 1 1 d . . . C6 C 0.5782(19) 0.3607(16) 0.6205(9) 0.050(4) Uani 1 1 d . . . H61 H 0.4421 0.3721 0.6102 0.060 Uiso 1 1 calc R . . H62 H 0.6524 0.3184 0.5827 0.060 Uiso 1 1 calc R . . C7 C 0.638(2) 0.5005(16) 0.6109(9) 0.055(4) Uani 1 1 d . . . H71 H 0.7784 0.4922 0.6084 0.066 Uiso 1 1 calc R . . H72 H 0.5923 0.5628 0.5622 0.066 Uiso 1 1 calc R . . N8 N 0.5574(15) 0.5580(12) 0.6766(7) 0.046(3) Uani 1 1 d . . . H81 H 0.4356 0.5958 0.6612 0.055 Uiso 1 1 calc R . . C9 C 0.639(2) 0.6796(13) 0.6801(8) 0.050(3) Uani 1 1 d . . . H91 H 0.6022 0.7569 0.6357 0.060 Uiso 1 1 calc R . . H92 H 0.7797 0.6606 0.6798 0.060 Uiso 1 1 calc R . . C10 C 0.5535(17) 0.7117(12) 0.7586(8) 0.039(3) Uani 1 1 d . . . H101 H 0.5765 0.8028 0.7578 0.047 Uiso 1 1 calc R . . H102 H 0.4143 0.7113 0.7625 0.047 Uiso 1 1 calc R . . C11 C 0.643(2) 0.6077(13) 0.8300(8) 0.045(3) Uani 1 1 d . . . H111 H 0.7830 0.5929 0.8213 0.054 Uiso 1 1 calc R . . H112 H 0.6138 0.6438 0.8751 0.054 Uiso 1 1 calc R . . N12 N 0.5686(13) 0.4784(9) 0.8453(5) 0.029(2) Uani 1 1 d . . . C13 C 0.3708(18) 0.4826(13) 0.8868(8) 0.042(3) Uani 1 1 d . . . H131 H 0.2851 0.5631 0.8600 0.050 Uiso 1 1 calc R . . H132 H 0.3801 0.4860 0.9400 0.050 Uiso 1 1 calc R . . C14 C 0.2911(19) 0.3491(14) 0.8864(11) 0.057(4) Uani 1 1 d . . . H141 H 0.2461 0.3037 0.9389 0.069 Uiso 1 1 calc R . . H142 H 0.1819 0.3727 0.8532 0.069 Uiso 1 1 calc R . . C15 C 0.7041(16) 0.3592(12) 0.8901(7) 0.035(3) Uani 1 1 d . . . H151 H 0.7284 0.3735 0.9395 0.041 Uiso 1 1 calc R . . H152 H 0.8269 0.3501 0.8606 0.041 Uiso 1 1 calc R . . C16 C 0.6093(19) 0.2296(12) 0.9043(8) 0.041(3) Uani 1 1 d . . . H161 H 0.7021 0.1577 0.8906 0.049 Uiso 1 1 calc R . . H162 H 0.5707 0.1977 0.9593 0.049 Uiso 1 1 calc R . . C20 C 0.8303(15) 0.2205(12) 0.7113(7) 0.033(3) Uani 1 1 d . . . H201 H 0.8933 0.2987 0.7102 0.040 Uiso 1 1 calc R . . H202 H 0.8397 0.1589 0.7636 0.040 Uiso 1 1 calc R . . C21 C 0.9423(16) 0.1475(12) 0.6556(7) 0.032(2) Uani 1 1 d . . . C22 C 0.9741(16) 0.0023(12) 0.6781(7) 0.036(3) Uani 1 1 d . . . H221 H 0.9221 -0.0461 0.7257 0.043 Uiso 1 1 calc R . . C23 C 1.0833(18) -0.0678(13) 0.6288(7) 0.037(3) Uani 1 1 d . . . H231 H 1.0951 -0.1630 0.6410 0.045 Uiso 1 1 calc R . . C24 C 1.1724(16) 0.0032(12) 0.5627(7) 0.036(3) Uani 1 1 d . . . C25 C 1.1448(17) 0.1465(12) 0.5384(7) 0.039(3) Uani 1 1 d . . . H251 H 1.1990 0.1930 0.4907 0.046 Uiso 1 1 calc R . . C26 C 1.0346(16) 0.2185(11) 0.5867(6) 0.030(2) Uani 1 1 d . . . H261 H 1.0224 0.3139 0.5733 0.036 Uiso 1 1 calc R . . N24 N 1.2958(14) -0.0655(14) 0.5077(7) 0.044(3) Uani 1 1 d . . . O241 O 1.3310(15) -0.1975(11) 0.5352(6) 0.060(3) Uani 1 1 d . . . O242 O 1.3483(12) -0.0041(10) 0.4462(6) 0.043(2) Uani 1 1 d . . . P3 P 1.0070(5) -0.1839(3) 0.91437(18) 0.0346(9) Uani 1 1 d . . . F4 F 1.0000(11) -0.1440(8) 0.9943(4) 0.0472(19) Uani 1 1 d . . . F5 F 1.0060(10) -0.3422(6) 0.9608(4) 0.0406(17) Uani 1 1 d . . . F6 F 1.0002(11) -0.0244(7) 0.8659(4) 0.0471(19) Uani 1 1 d . . . F7 F 1.0171(15) -0.2248(8) 0.8334(5) 0.061(2) Uani 1 1 d . . . F9 F 0.7712(10) -0.1670(8) 0.9180(6) 0.061(2) Uani 1 1 d . . . F10 F 1.2395(10) -0.2029(7) 0.9099(4) 0.0451(18) 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 Cu1 0.0665(16) 0.0656(15) 0.0863(18) -0.0321(12) -0.0113(11) 0.0001(11) Br1A 0.0365(17) 0.058(3) 0.098(5) -0.040(3) -0.016(2) 0.0063(19) Br1B 0.027(2) 0.039(3) 0.101(7) -0.025(4) -0.017(3) -0.0002(17) N1 0.040(6) 0.036(5) 0.034(5) -0.017(4) 0.003(4) -0.002(4) C2 0.033(7) 0.068(9) 0.065(9) -0.037(7) 0.010(6) -0.026(6) C3 0.069(10) 0.046(8) 0.061(10) -0.015(7) -0.002(7) -0.015(7) C4 0.039(8) 0.069(10) 0.096(12) -0.059(9) 0.020(7) -0.036(7) N5 0.022(5) 0.055(7) 0.061(7) -0.035(6) -0.006(4) -0.007(4) C6 0.033(7) 0.068(9) 0.069(10) -0.053(8) -0.001(6) -0.005(6) C7 0.054(9) 0.069(10) 0.053(8) -0.041(7) -0.013(6) 0.008(7) N8 0.029(5) 0.053(7) 0.059(7) -0.031(6) -0.011(4) 0.016(5) C9 0.073(10) 0.030(6) 0.045(8) -0.009(5) -0.015(6) 0.002(6) C10 0.032(6) 0.027(5) 0.065(8) -0.023(6) -0.008(5) 0.001(5) C11 0.051(8) 0.043(7) 0.057(8) -0.029(6) -0.002(6) -0.022(6) N12 0.029(5) 0.029(5) 0.037(5) -0.019(4) -0.003(4) -0.003(4) C13 0.033(7) 0.038(7) 0.059(8) -0.018(6) 0.003(5) -0.014(5) C14 0.024(6) 0.034(7) 0.114(13) -0.028(8) 0.014(7) -0.002(5) C15 0.020(5) 0.040(6) 0.046(7) -0.013(5) -0.009(4) -0.005(4) C16 0.043(7) 0.027(6) 0.055(8) -0.012(5) -0.008(6) -0.005(5) C20 0.021(5) 0.041(6) 0.046(7) -0.025(5) 0.008(4) -0.011(5) C21 0.025(5) 0.034(6) 0.042(6) -0.022(5) -0.002(4) 0.005(4) C22 0.024(6) 0.034(6) 0.049(7) -0.012(5) 0.002(5) -0.004(5) C23 0.046(7) 0.037(6) 0.033(6) -0.022(5) -0.004(5) 0.005(5) C24 0.018(5) 0.043(7) 0.058(8) -0.033(6) -0.019(5) 0.006(5) C25 0.034(6) 0.034(6) 0.039(7) -0.003(5) 0.014(5) -0.002(5) C26 0.035(6) 0.026(5) 0.028(6) -0.008(4) 0.002(4) 0.001(4) N24 0.020(5) 0.070(8) 0.053(7) -0.039(6) -0.018(5) 0.012(5) O241 0.055(6) 0.059(7) 0.076(7) -0.044(6) -0.006(5) 0.010(5) O242 0.023(4) 0.066(6) 0.047(6) -0.033(5) -0.005(4) 0.009(4) P3 0.0385(18) 0.0250(15) 0.0418(19) -0.0090(12) -0.0096(12) -0.0046(12) F4 0.056(5) 0.040(4) 0.052(4) -0.024(3) -0.005(3) -0.003(3) F5 0.051(4) 0.025(3) 0.041(4) -0.002(3) -0.003(3) -0.006(3) F6 0.054(5) 0.027(4) 0.060(5) -0.006(3) -0.015(3) -0.008(3) F7 0.095(7) 0.041(4) 0.052(5) -0.017(4) -0.023(4) -0.005(4) F9 0.023(4) 0.044(4) 0.116(7) -0.017(4) -0.033(4) 0.004(3) F10 0.038(4) 0.039(4) 0.059(5) -0.014(3) 0.008(3) -0.013(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 Cu1 N8 1.846(13) . ? Cu1 N12 1.997(9) . ? Cu1 N5 2.003(10) . ? Cu1 N1 2.085(10) . ? Cu1 Br1A 2.726(8) . ? Br1A Br1B 0.807(6) . ? N1 C16 1.443(17) . ? N1 C14 1.449(15) . ? N1 C2 1.491(16) . ? C2 C3 1.52(2) . ? C2 H21 0.9700 . ? C2 H22 0.9700 . ? C3 C4 1.39(2) . ? C3 H31 0.9700 . ? C3 H32 0.9700 . ? C4 N5 1.523(16) . ? C4 H41 0.9700 . ? C4 H42 0.9700 . ? N5 C6 1.414(19) . ? N5 C20 1.577(14) . ? C6 C7 1.52(2) . ? C6 H61 0.9700 . ? C6 H62 0.9700 . ? C7 N8 1.484(16) . ? C7 H71 0.9700 . ? C7 H72 0.9700 . ? N8 C9 1.473(18) . ? N8 H81 0.9100 . ? C9 C10 1.573(19) . ? C9 H91 0.9700 . ? C9 H92 0.9700 . ? C10 C11 1.53(2) . ? C10 H101 0.9700 . ? C10 H102 0.9700 . ? C11 N12 1.449(15) . ? C11 H111 0.9700 . ? C11 H112 0.9700 . ? N12 C15 1.500(15) . ? N12 C13 1.507(15) . ? C13 C14 1.561(17) . ? C13 H131 0.9700 . ? C13 H132 0.9700 . ? C14 H141 0.9700 . ? C14 H142 0.9700 . ? C15 C16 1.529(16) . ? C15 H151 0.9700 . ? C15 H152 0.9700 . ? C16 H161 0.9700 . ? C16 H162 0.9700 . ? C20 C21 1.500(15) . ? C20 H201 0.9700 . ? C20 H202 0.9700 . ? C21 C26 1.400(17) . ? C21 C22 1.414(16) . ? C22 C23 1.389(16) . ? C22 H221 0.9300 . ? C23 C24 1.355(19) . ? C23 H231 0.9300 . ? C24 C25 1.396(17) . ? C24 N24 1.495(15) . ? C25 C26 1.391(16) . ? C25 H251 0.9300 . ? C26 H261 0.9300 . ? N24 O242 1.161(15) . ? N24 O241 1.294(16) . ? P3 F4 1.588(8) . ? P3 F5 1.602(7) . ? P3 F10 1.603(8) . ? P3 F7 1.610(8) . ? P3 F6 1.616(7) . ? P3 F9 1.628(8) . ? 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 N8 Cu1 N12 97.8(4) . . ? N8 Cu1 N5 93.4(5) . . ? N12 Cu1 N5 142.8(4) . . ? N8 Cu1 N1 172.9(4) . . ? N12 Cu1 N1 76.1(4) . . ? N5 Cu1 N1 93.7(4) . . ? N8 Cu1 Br1A 83.5(4) . . ? N12 Cu1 Br1A 116.5(3) . . ? N5 Cu1 Br1A 99.9(3) . . ? N1 Cu1 Br1A 95.9(4) . . ? Br1B Br1A Cu1 128.0(5) . . ? C16 N1 C14 109.6(11) . . ? C16 N1 C2 114.5(10) . . ? C14 N1 C2 112.7(10) . . ? C16 N1 Cu1 104.5(8) . . ? C14 N1 Cu1 93.2(8) . . ? C2 N1 Cu1 120.2(8) . . ? N1 C2 C3 112.7(10) . . ? N1 C2 H21 109.1 . . ? C3 C2 H21 109.1 . . ? N1 C2 H22 109.1 . . ? C3 C2 H22 109.1 . . ? H21 C2 H22 107.8 . . ? C4 C3 C2 122.7(14) . . ? C4 C3 H31 106.7 . . ? C2 C3 H31 106.7 . . ? C4 C3 H32 106.7 . . ? C2 C3 H32 106.7 . . ? H31 C3 H32 106.6 . . ? C3 C4 N5 115.9(12) . . ? C3 C4 H41 108.3 . . ? N5 C4 H41 108.3 . . ? C3 C4 H42 108.3 . . ? N5 C4 H42 108.3 . . ? H41 C4 H42 107.4 . . ? C6 N5 C4 109.7(11) . . ? C6 N5 C20 112.8(9) . . ? C4 N5 C20 109.7(10) . . ? C6 N5 Cu1 98.9(8) . . ? C4 N5 Cu1 115.6(8) . . ? C20 N5 Cu1 109.8(6) . . ? N5 C6 C7 111.6(10) . . ? N5 C6 H61 109.3 . . ? C7 C6 H61 109.3 . . ? N5 C6 H62 109.3 . . ? C7 C6 H62 109.3 . . ? H61 C6 H62 108.0 . . ? N8 C7 C6 111.3(13) . . ? N8 C7 H71 109.4 . . ? C6 C7 H71 109.4 . . ? N8 C7 H72 109.4 . . ? C6 C7 H72 109.4 . . ? H71 C7 H72 108.0 . . ? C9 N8 C7 114.6(12) . . ? C9 N8 Cu1 127.9(9) . . ? C7 N8 Cu1 105.4(9) . . ? C9 N8 H81 101.6 . . ? C7 N8 H81 101.6 . . ? Cu1 N8 H81 101.6 . . ? N8 C9 C10 105.9(11) . . ? N8 C9 H91 110.5 . . ? C10 C9 H91 110.5 . . ? N8 C9 H92 110.5 . . ? C10 C9 H92 110.5 . . ? H91 C9 H92 108.7 . . ? C11 C10 C9 112.3(10) . . ? C11 C10 H101 109.1 . . ? C9 C10 H101 109.1 . . ? C11 C10 H102 109.1 . . ? C9 C10 H102 109.1 . . ? H101 C10 H102 107.9 . . ? N12 C11 C10 110.7(10) . . ? N12 C11 H111 109.5 . . ? C10 C11 H111 109.5 . . ? N12 C11 H112 109.5 . . ? C10 C11 H112 109.5 . . ? H111 C11 H112 108.1 . . ? C11 N12 C15 112.6(10) . . ? C11 N12 C13 111.9(9) . . ? C15 N12 C13 110.0(9) . . ? C11 N12 Cu1 121.1(8) . . ? C15 N12 Cu1 101.6(7) . . ? C13 N12 Cu1 98.3(7) . . ? N12 C13 C14 107.0(9) . . ? N12 C13 H131 110.3 . . ? C14 C13 H131 110.3 . . ? N12 C13 H132 110.3 . . ? C14 C13 H132 110.3 . . ? H131 C13 H132 108.6 . . ? N1 C14 C13 110.3(10) . . ? N1 C14 H141 109.6 . . ? C13 C14 H141 109.6 . . ? N1 C14 H142 109.6 . . ? C13 C14 H142 109.6 . . ? H141 C14 H142 108.1 . . ? N12 C15 C16 108.1(9) . . ? N12 C15 H151 110.1 . . ? C16 C15 H151 110.1 . . ? N12 C15 H152 110.1 . . ? C16 C15 H152 110.1 . . ? H151 C15 H152 108.4 . . ? N1 C16 C15 110.5(10) . . ? N1 C16 H161 109.5 . . ? C15 C16 H161 109.5 . . ? N1 C16 H162 109.5 . . ? C15 C16 H162 109.5 . . ? H161 C16 H162 108.1 . . ? C21 C20 N5 116.9(9) . . ? C21 C20 H201 108.1 . . ? N5 C20 H201 108.1 . . ? C21 C20 H202 108.1 . . ? N5 C20 H202 108.1 . . ? H201 C20 H202 107.3 . . ? C26 C21 C22 119.2(9) . . ? C26 C21 C20 121.7(10) . . ? C22 C21 C20 118.6(10) . . ? C23 C22 C21 119.8(11) . . ? C23 C22 H221 120.1 . . ? C21 C22 H221 120.1 . . ? C24 C23 C22 119.7(11) . . ? C24 C23 H231 120.1 . . ? C22 C23 H231 120.1 . . ? C23 C24 C25 122.1(10) . . ? C23 C24 N24 122.7(11) . . ? C25 C24 N24 115.1(12) . . ? C26 C25 C24 118.8(10) . . ? C26 C25 H251 120.6 . . ? C24 C25 H251 120.6 . . ? C25 C26 C21 120.0(10) . . ? C25 C26 H261 120.0 . . ? C21 C26 H261 120.0 . . ? O242 N24 O241 124.8(10) . . ? O242 N24 C24 122.0(12) . . ? O241 N24 C24 113.2(12) . . ? F4 P3 F5 90.7(4) . . ? F4 P3 F10 90.7(4) . . ? F5 P3 F10 91.6(4) . . ? F4 P3 F7 179.3(5) . . ? F5 P3 F7 89.3(4) . . ? F10 P3 F7 88.6(5) . . ? F4 P3 F6 90.6(4) . . ? F5 P3 F6 177.7(4) . . ? F10 P3 F6 90.3(4) . . ? F7 P3 F6 89.5(4) . . ? F4 P3 F9 90.3(5) . . ? F5 P3 F9 87.8(4) . . ? F10 P3 F9 178.9(5) . . ? F7 P3 F9 90.4(5) . . ? F6 P3 F9 90.2(4) . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.918 _refine_diff_density_max 2.544 _refine_diff_density_min -1.984 _refine_diff_density_rms 0.452 _publ_section_references ; A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori & M. Camalli (1994). J. Appl. Cryst. 27, 435. R.W. Hooft (1998). COLLECT. Nonius BV, Delft, The Netherlands. Z. Otwinowski & W. Minor (1997). Methods Enzymol. 276, 307. G.M. Sheldrick (1997). SHELXL97. University of Gottingen, Germany. A.L. Spek (1999). PLATON. Version 1999. Utrecht University, The Netherlands. ; # Attachment 'B709747F-redacoh.cif' data_redacoh _database_code_depnum_ccdc_archive 'CCDC 652361' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H34 Br N5 O4, Br, 2.5(H2 O)' _chemical_formula_sum 'C21 H39 Br N5 O6.50' _chemical_formula_weight 545.48 _chemical_compound_source 'synthesized by the authors' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.4788(4) _cell_length_b 19.7272(4) _cell_length_c 13.7214(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.7160(11) _cell_angle_gamma 90.00 _cell_volume 5224.88(19) _cell_formula_units_Z 8 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 28613 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2296 _exptl_absorpt_coefficient_mu 1.619 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.48056 _exptl_absorpt_correction_T_max 0.65102 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _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 36155 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5978 _reflns_number_gt 4839 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1030P)^2^+13.3827P] 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 5978 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1828 _refine_ls_wR_factor_gt 0.1680 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.167766(19) 0.359609(18) 0.12895(2) 0.04671(16) Uani 1 1 d . . . N1 N 0.28438(18) 0.01400(15) 0.1552(2) 0.0454(7) Uani 1 1 d . . . C2 C 0.3651(2) 0.0161(2) 0.1578(4) 0.0641(11) Uani 1 1 d . . . H21 H 0.3772 -0.0159 0.1092 0.077 Uiso 0.620(12) 1 d PR . . H22 H 0.3861 0.0000 0.2217 0.077 Uiso 0.620(12) 1 d PR . . H23 H 0.3835 -0.0275 0.1811 0.077 Uiso 0.380(12) 1 d PR . . H24 H 0.3751 0.0216 0.0909 0.077 Uiso 0.380(12) 1 d PR . . C3A C 0.4001(4) 0.0880(3) 0.1378(5) 0.0548(16) Uani 0.620(12) 1 d P . . H31 H 0.4475 0.0786 0.1273 0.066 Uiso 0.620(12) 1 d PR . . H32 H 0.3764 0.1045 0.0756 0.066 Uiso 0.620(12) 1 d PR . . C3B C 0.4021(6) 0.0702(5) 0.2183(9) 0.0548(16) Uani 0.38 1 d P . . H33 H 0.3879 0.0646 0.2829 0.066 Uiso 0.380(12) 1 d PR . . H34 H 0.4505 0.0569 0.2252 0.066 Uiso 0.380(12) 1 d PR . . C4 C 0.4033(3) 0.1426(2) 0.2025(6) 0.084(2) Uani 1 1 d . . . H41 H 0.4408 0.1717 0.1881 0.101 Uiso 0.620(12) 1 d PR . . H42 H 0.4170 0.1242 0.2678 0.101 Uiso 0.620(12) 1 d PR . . H43 H 0.4162 0.1492 0.1374 0.101 Uiso 0.380(12) 1 d PR . . H44 H 0.4408 0.1609 0.2486 0.101 Uiso 0.380(12) 1 d PR . . N5 N 0.34344(16) 0.18643(15) 0.2092(2) 0.0466(7) Uani 1 1 d . . . C6 C 0.3525(2) 0.2229(2) 0.3026(3) 0.0580(11) Uani 1 1 d . . . H61 H 0.3865 0.2585 0.2998 0.070 Uiso 1 1 calc R . . H62 H 0.3704 0.1919 0.3547 0.070 Uiso 1 1 calc R . . C7 C 0.2860(2) 0.25391(19) 0.3269(3) 0.0533(10) Uani 1 1 d . . . H71 H 0.2945 0.2772 0.3896 0.064 Uiso 1 1 calc R . . H72 H 0.2689 0.2868 0.2769 0.064 Uiso 1 1 calc R . . N8 N 0.23311(17) 0.19958(14) 0.3318(2) 0.0432(7) Uani 1 1 d . . . H81 H 0.2343 0.1715 0.2804 0.056 Uiso 1 1 calc R . . H82 H 0.2451 0.1753 0.3870 0.056 Uiso 1 1 calc R . . C9 C 0.1609(2) 0.22372(19) 0.3310(3) 0.0538(9) Uani 1 1 d . . . H91 H 0.1494 0.2552 0.2770 0.065 Uiso 1 1 calc R . . H92 H 0.1571 0.2477 0.3918 0.065 Uiso 1 1 calc R . . C10 C 0.1101(2) 0.1649(2) 0.3202(3) 0.0533(9) Uani 1 1 d . . . H101 H 0.0646 0.1817 0.3290 0.064 Uiso 1 1 calc R . . H102 H 0.1239 0.1323 0.3721 0.064 Uiso 1 1 calc R . . C11 C 0.1051(2) 0.1286(2) 0.2212(3) 0.0550(10) Uani 1 1 d . . . H111 H 0.0710 0.0925 0.2194 0.066 Uiso 1 1 calc R . . H112 H 0.0893 0.1604 0.1690 0.066 Uiso 1 1 calc R . . N12 N 0.17239(15) 0.09944(14) 0.2035(2) 0.0387(6) Uani 1 1 d . . . C13 C 0.1942(2) 0.04057(18) 0.2641(3) 0.0541(10) Uani 1 1 d . . . H131 H 0.1673 0.0012 0.2399 0.065 Uiso 1 1 calc R . . H132 H 0.1866 0.0488 0.3315 0.065 Uiso 1 1 calc R . . C14 C 0.2714(3) 0.0276(2) 0.2597(3) 0.0575(10) Uani 1 1 d . . . H141 H 0.2980 0.0668 0.2851 0.069 Uiso 1 1 calc R . . H142 H 0.2866 -0.0110 0.3007 0.069 Uiso 1 1 calc R . . C15 C 0.17581(19) 0.08115(19) 0.1006(3) 0.0430(8) Uani 1 1 d . . . H151 H 0.1577 0.1180 0.0579 0.052 Uiso 1 1 calc R . . H152 H 0.1476 0.0413 0.0833 0.052 Uiso 1 1 calc R . . C16 C 0.24933(19) 0.06704(17) 0.0862(3) 0.0418(7) Uani 1 1 d . . . H161 H 0.2756 0.1089 0.0953 0.050 Uiso 1 1 calc R . . H162 H 0.2503 0.0522 0.0190 0.050 Uiso 1 1 calc R . . C20 C 0.2622(3) -0.05649(19) 0.1268(3) 0.0578(11) Uani 1 1 d . . . H201 H 0.2130 -0.0594 0.1318 0.069 Uiso 1 1 calc R . . H202 H 0.2855 -0.0864 0.1768 0.069 Uiso 1 1 calc R . . C21 C 0.2727(2) -0.0871(2) 0.0256(3) 0.0504(9) Uani 1 1 d . . . O211 O 0.2577(3) -0.13962(18) 0.0110(3) 0.1001(17) Uani 1 1 d . . . O212 O 0.3047(2) -0.0501(2) -0.0285(3) 0.0862(11) Uani 1 1 d . . . C30 C 0.32632(17) 0.23209(17) 0.1235(2) 0.0389(7) Uani 1 1 d . . . H301 H 0.2830 0.2549 0.1297 0.047 Uiso 1 1 calc R . . H302 H 0.3191 0.2047 0.0643 0.047 Uiso 1 1 calc R . . C31 C 0.38092(17) 0.28544(17) 0.1112(2) 0.0376(7) Uani 1 1 d . . . C32 C 0.43625(19) 0.2705(2) 0.0610(3) 0.0459(8) Uani 1 1 d . . . H321 H 0.4390 0.2278 0.0331 0.055 Uiso 1 1 calc R . . C33 C 0.4870(2) 0.3172(2) 0.0514(3) 0.0521(9) Uani 1 1 d . . . H331 H 0.5238 0.3069 0.0173 0.063 Uiso 1 1 calc R . . C34 C 0.4818(2) 0.3796(2) 0.0935(3) 0.0576(11) Uani 1 1 d . . . N34 N 0.5370(3) 0.4295(3) 0.0863(4) 0.105(2) Uani 1 1 d . . . O341 O 0.5265(3) 0.4881(3) 0.1146(4) 0.144(3) Uani 1 1 d . . . O342 O 0.5887(3) 0.4110(3) 0.0520(4) 0.144(3) Uani 1 1 d . . . C35 C 0.4271(2) 0.3977(2) 0.1422(3) 0.0559(10) Uani 1 1 d . . . H351 H 0.4245 0.4408 0.1690 0.067 Uiso 1 1 calc R . . C36 C 0.3762(2) 0.35003(17) 0.1503(3) 0.0437(8) Uani 1 1 d . . . H361 H 0.3385 0.3612 0.1821 0.052 Uiso 1 1 calc R . . O1W O 0.0112(3) 0.2999(3) 0.1539(5) 0.140(2) Uani 1 1 d . . . O2W O 0.4382(3) 0.1242(7) 0.4945(6) 0.295(8) Uani 1 1 d . . . O3W O 0.4571(7) -0.0129(9) 0.4174(10) 0.186(8) Uani 0.50 1 d P . . 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 0.0567(2) 0.0486(2) 0.0347(2) -0.00303(14) 0.00553(15) -0.01041(15) N1 0.070(2) 0.0358(14) 0.0305(14) -0.0027(11) 0.0059(13) 0.0021(13) C2 0.068(3) 0.058(2) 0.064(3) -0.005(2) 0.002(2) 0.011(2) C3A 0.057(3) 0.048(3) 0.057(3) 0.002(2) -0.001(3) -0.001(2) C3B 0.057(3) 0.048(3) 0.057(3) 0.002(2) -0.001(3) -0.001(2) C4 0.047(2) 0.048(2) 0.159(6) 0.021(3) 0.023(3) 0.0007(18) N5 0.0449(16) 0.0401(15) 0.0547(18) 0.0078(13) 0.0063(13) -0.0044(12) C6 0.064(2) 0.062(2) 0.043(2) 0.0142(18) -0.0120(18) -0.024(2) C7 0.086(3) 0.0426(19) 0.0303(17) -0.0032(14) 0.0061(17) -0.0234(19) N8 0.0688(19) 0.0335(13) 0.0285(13) 0.0008(11) 0.0116(13) -0.0077(13) C9 0.076(3) 0.0416(19) 0.046(2) -0.0012(16) 0.0186(19) 0.0054(18) C10 0.063(2) 0.053(2) 0.048(2) -0.0018(18) 0.0238(18) 0.0023(18) C11 0.048(2) 0.070(3) 0.049(2) -0.0111(19) 0.0127(17) -0.0028(18) N12 0.0490(15) 0.0368(14) 0.0317(13) -0.0004(11) 0.0105(11) -0.0055(11) C13 0.092(3) 0.0369(18) 0.0371(19) 0.0022(15) 0.0218(19) -0.0048(18) C14 0.089(3) 0.045(2) 0.0367(19) -0.0016(15) 0.0028(19) 0.007(2) C15 0.0522(19) 0.0470(18) 0.0298(15) -0.0033(14) 0.0057(14) -0.0115(15) C16 0.057(2) 0.0348(16) 0.0348(16) 0.0038(13) 0.0104(14) -0.0032(14) C20 0.096(3) 0.0370(18) 0.039(2) -0.0009(15) 0.006(2) 0.0003(19) C21 0.068(2) 0.055(2) 0.0287(17) 0.0097(16) 0.0069(16) 0.0116(18) O211 0.204(5) 0.061(2) 0.0353(17) -0.0115(15) 0.014(2) 0.009(2) O212 0.127(3) 0.082(2) 0.0544(19) -0.0087(17) 0.030(2) -0.018(2) C30 0.0422(16) 0.0400(16) 0.0354(16) -0.0038(13) 0.0083(13) -0.0078(13) C31 0.0418(16) 0.0428(17) 0.0292(15) -0.0036(13) 0.0080(12) -0.0089(13) C32 0.0512(19) 0.0495(19) 0.0400(18) -0.0122(15) 0.0168(15) -0.0097(16) C33 0.0480(19) 0.069(3) 0.0420(19) -0.0142(18) 0.0164(16) -0.0166(18) C34 0.061(2) 0.072(3) 0.043(2) -0.0192(19) 0.0183(17) -0.038(2) N34 0.117(4) 0.119(4) 0.092(3) -0.059(3) 0.064(3) -0.087(3) O341 0.192(5) 0.119(4) 0.146(4) -0.083(3) 0.112(4) -0.123(4) O342 0.116(4) 0.172(5) 0.164(5) -0.088(4) 0.094(4) -0.104(4) C35 0.075(3) 0.052(2) 0.045(2) -0.0193(17) 0.0253(19) -0.0273(19) C36 0.055(2) 0.0420(18) 0.0373(18) -0.0080(14) 0.0194(15) -0.0102(15) O1W 0.101(3) 0.160(5) 0.178(6) -0.050(4) 0.082(4) -0.042(3) O2W 0.097(4) 0.59(2) 0.184(7) 0.261(11) -0.026(4) -0.085(7) O3W 0.127(9) 0.260(17) 0.154(11) 0.102(11) -0.042(8) -0.108(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C20 1.492(5) . ? N1 C16 1.511(4) . ? N1 C14 1.513(5) . ? N1 C2 1.568(6) . ? C2 C3B 1.478(12) . ? C2 C3A 1.614(8) . ? C2 H21 0.9700 . ? C2 H22 0.9700 . ? C2 H23 0.9700 . ? C2 H24 0.9700 . ? C3A C3B 1.155(13) . ? C3A C4 1.392(9) . ? C3A H24 1.5116 . ? C3A H31 0.9700 . ? C3A H32 0.9700 . ? C3A H34 1.5687 . ? C3A H43 1.2469 . ? C3B C4 1.446(11) . ? C3B H22 1.4209 . ? C3B H33 0.9700 . ? C3B H34 0.9700 . ? C3B H42 1.2770 . ? C4 N5 1.464(6) . ? C4 H41 0.9700 . ? C4 H42 0.9700 . ? C4 H43 0.9700 . ? C4 H44 0.9700 . ? N5 C6 1.459(5) . ? N5 C30 1.484(5) . ? C6 C7 1.510(7) . ? C6 H61 0.9700 . ? C6 H62 0.9700 . ? C7 N8 1.494(5) . ? C7 H71 0.9700 . ? C7 H72 0.9700 . ? N8 C9 1.483(5) . ? N8 H81 0.9000 . ? N8 H82 0.9000 . ? C9 C10 1.520(6) . ? C9 H91 0.9700 . ? C9 H92 0.9700 . ? C10 C11 1.527(6) . ? C10 H101 0.9700 . ? C10 H102 0.9700 . ? C11 N12 1.481(5) . ? C11 H111 0.9700 . ? C11 H112 0.9700 . ? N12 C13 1.458(5) . ? N12 C15 1.468(4) . ? C13 C14 1.534(6) . ? C13 H131 0.9700 . ? C13 H132 0.9700 . ? C14 H141 0.9700 . ? C14 H142 0.9700 . ? C15 C16 1.498(5) . ? C15 H151 0.9700 . ? C15 H152 0.9700 . ? C16 H161 0.9700 . ? C16 H162 0.9700 . ? C20 C21 1.552(5) . ? C20 H201 0.9700 . ? C20 H202 0.9700 . ? C21 O211 1.088(5) . ? C21 O212 1.264(5) . ? C30 C31 1.522(4) . ? C30 H301 0.9700 . ? C30 H302 0.9700 . ? C31 C32 1.387(5) . ? C31 C36 1.390(5) . ? C32 C33 1.370(5) . ? C32 H321 0.9300 . ? C33 C34 1.369(6) . ? C33 H331 0.9300 . ? C34 C35 1.378(6) . ? C34 N34 1.470(5) . ? N34 O342 1.223(7) . ? N34 O341 1.245(7) . ? C35 C36 1.381(5) . ? C35 H351 0.9300 . ? C36 H361 0.9300 . ? 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 C20 N1 C16 113.0(3) . . ? C20 N1 C14 109.5(3) . . ? C16 N1 C14 110.6(3) . . ? C20 N1 C2 106.6(3) . . ? C16 N1 C2 111.3(3) . . ? C14 N1 C2 105.6(3) . . ? C3B C2 N1 116.4(6) . . ? C3B C2 C3A 43.6(5) . . ? N1 C2 C3A 117.7(4) . . ? C3B C2 H21 135.2 . . ? N1 C2 H21 107.6 . . ? C3A C2 H21 107.9 . . ? C3B C2 H22 67.3 . . ? N1 C2 H22 108.2 . . ? C3A C2 H22 107.8 . . ? H21 C2 H22 107.2 . . ? C3B C2 H23 108.9 . . ? N1 C2 H23 108.1 . . ? C3A C2 H23 133.6 . . ? H21 C2 H23 62.3 . . ? H22 C2 H23 47.1 . . ? C3B C2 H24 107.8 . . ? N1 C2 H24 108.0 . . ? C3A C2 H24 66.2 . . ? H21 C2 H24 47.5 . . ? H22 C2 H24 141.2 . . ? H23 C2 H24 107.4 . . ? C3B C3A C4 68.5(7) . . ? C3B C3A C2 61.9(6) . . ? C4 C3A C2 123.7(6) . . ? C3B C3A H24 96.3 . . ? C4 C3A H24 157.8 . . ? C2 C3A H24 36.0 . . ? C3B C3A H31 100.0 . . ? C4 C3A H31 106.4 . . ? C2 C3A H31 106.8 . . ? H24 C3A H31 91.7 . . ? C3B C3A H32 153.3 . . ? C4 C3A H32 106.1 . . ? C2 C3A H32 106.3 . . ? H24 C3A H32 80.0 . . ? H31 C3A H32 106.5 . . ? C3B C3A H34 38.0 . . ? C4 C3A H34 81.1 . . ? C2 C3A H34 76.2 . . ? H24 C3A H34 96.9 . . ? H31 C3A H34 61.9 . . ? H32 C3A H34 168.1 . . ? C3B C3A H43 108.9 . . ? C4 C3A H43 42.7 . . ? C2 C3A H43 164.5 . . ? H24 C3A H43 154.7 . . ? H31 C3A H43 86.6 . . ? H32 C3A H43 76.3 . . ? H34 C3A H43 104.5 . . ? C3A C3B C4 63.5(7) . . ? C3A C3B C2 74.5(7) . . ? C4 C3B C2 130.2(9) . . ? C3A C3B H22 110.5 . . ? C4 C3B H22 167.3 . . ? C2 C3B H22 39.0 . . ? C3A C3B H33 158.7 . . ? C4 C3B H33 105.1 . . ? C2 C3B H33 104.7 . . ? H22 C3B H33 76.6 . . ? C3A C3B H34 94.8 . . ? C4 C3B H34 104.3 . . ? C2 C3B H34 104.8 . . ? H22 C3B H34 87.1 . . ? H33 C3B H34 105.9 . . ? C3A C3B H42 103.3 . . ? C4 C3B H42 41.1 . . ? C2 C3B H42 163.7 . . ? H22 C3B H42 146.2 . . ? H33 C3B H42 71.4 . . ? H34 C3B H42 91.4 . . ? C3A C4 C3B 48.0(6) . . ? C3A C4 N5 122.0(5) . . ? C3B C4 N5 123.1(6) . . ? C3A C4 H41 107.3 . . ? C3B C4 H41 130.0 . . ? N5 C4 H41 106.9 . . ? C3A C4 H42 106.5 . . ? C3B C4 H42 60.0 . . ? N5 C4 H42 106.6 . . ? H41 C4 H42 106.7 . . ? C3A C4 H43 60.7 . . ? C3B C4 H43 106.4 . . ? N5 C4 H43 106.6 . . ? H41 C4 H43 55.7 . . ? H42 C4 H43 145.9 . . ? C3A C4 H44 131.9 . . ? C3B C4 H44 107.2 . . ? N5 C4 H44 106.1 . . ? H41 C4 H44 52.4 . . ? H42 C4 H44 56.4 . . ? H43 C4 H44 106.5 . . ? C6 N5 C4 110.0(4) . . ? C6 N5 C30 112.6(3) . . ? C4 N5 C30 113.9(4) . . ? N5 C6 C7 112.8(3) . . ? N5 C6 H61 109.0 . . ? C7 C6 H61 109.0 . . ? N5 C6 H62 109.0 . . ? C7 C6 H62 109.0 . . ? H61 C6 H62 107.8 . . ? N8 C7 C6 109.7(3) . . ? N8 C7 H71 109.7 . . ? C6 C7 H71 109.7 . . ? N8 C7 H72 109.7 . . ? C6 C7 H72 109.7 . . ? H71 C7 H72 108.2 . . ? C9 N8 C7 115.3(3) . . ? C9 N8 H81 108.4 . . ? C7 N8 H81 108.4 . . ? C9 N8 H82 108.4 . . ? C7 N8 H82 108.4 . . ? H81 N8 H82 107.5 . . ? N8 C9 C10 111.1(3) . . ? N8 C9 H91 109.4 . . ? C10 C9 H91 109.4 . . ? N8 C9 H92 109.4 . . ? C10 C9 H92 109.4 . . ? H91 C9 H92 108.0 . . ? C9 C10 C11 114.1(3) . . ? C9 C10 H101 108.7 . . ? C11 C10 H101 108.7 . . ? C9 C10 H102 108.7 . . ? C11 C10 H102 108.7 . . ? H101 C10 H102 107.6 . . ? N12 C11 C10 112.0(3) . . ? N12 C11 H111 109.2 . . ? C10 C11 H111 109.2 . . ? N12 C11 H112 109.2 . . ? C10 C11 H112 109.2 . . ? H111 C11 H112 107.9 . . ? C13 N12 C15 107.8(3) . . ? C13 N12 C11 114.3(3) . . ? C15 N12 C11 114.1(3) . . ? N12 C13 C14 108.8(3) . . ? N12 C13 H131 109.9 . . ? C14 C13 H131 109.9 . . ? N12 C13 H132 109.9 . . ? C14 C13 H132 109.9 . . ? H131 C13 H132 108.3 . . ? N1 C14 C13 110.9(3) . . ? N1 C14 H141 109.5 . . ? C13 C14 H141 109.5 . . ? N1 C14 H142 109.5 . . ? C13 C14 H142 109.5 . . ? H141 C14 H142 108.1 . . ? N12 C15 C16 109.9(3) . . ? N12 C15 H151 109.7 . . ? C16 C15 H151 109.7 . . ? N12 C15 H152 109.7 . . ? C16 C15 H152 109.7 . . ? H151 C15 H152 108.2 . . ? C15 C16 N1 113.9(3) . . ? C15 C16 H161 108.8 . . ? N1 C16 H161 108.8 . . ? C15 C16 H162 108.8 . . ? N1 C16 H162 108.8 . . ? H161 C16 H162 107.7 . . ? N1 C20 C21 121.8(4) . . ? N1 C20 H201 106.9 . . ? C21 C20 H201 106.9 . . ? N1 C20 H202 106.9 . . ? C21 C20 H202 106.9 . . ? H201 C20 H202 106.7 . . ? O211 C21 O212 125.6(4) . . ? O211 C21 C20 118.1(4) . . ? O212 C21 C20 115.8(4) . . ? N5 C30 C31 114.9(3) . . ? N5 C30 H301 108.5 . . ? C31 C30 H301 108.5 . . ? N5 C30 H302 108.5 . . ? C31 C30 H302 108.5 . . ? H301 C30 H302 107.5 . . ? C32 C31 C36 118.8(3) . . ? C32 C31 C30 120.6(3) . . ? C36 C31 C30 120.6(3) . . ? C33 C32 C31 121.5(3) . . ? C33 C32 H321 119.2 . . ? C31 C32 H321 119.2 . . ? C34 C33 C32 118.1(4) . . ? C34 C33 H331 121.0 . . ? C32 C33 H331 121.0 . . ? C33 C34 C35 122.8(3) . . ? C33 C34 N34 118.6(4) . . ? C35 C34 N34 118.6(4) . . ? O342 N34 O341 125.1(4) . . ? O342 N34 C34 118.2(5) . . ? O341 N34 C34 116.7(5) . . ? C34 C35 C36 118.2(4) . . ? C34 C35 H351 120.9 . . ? C36 C35 H351 120.9 . . ? C35 C36 C31 120.6(3) . . ? C35 C36 H361 119.7 . . ? C31 C36 H361 119.7 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.907 _refine_diff_density_min -0.935 _refine_diff_density_rms 0.091 _publ_section_references ; A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori & M. Camalli (1994). J. Appl. Cryst. 27, 435. P. Coppens (1970). Crystallographic Computing (eds F.R. Ahmed, S.R. Hall & C.P. Huber), pp. 255-270, Copenhagen, Munksgaard. R.W. Hooft (1998). COLLECT. Nonius BV, Delft, The Netherlands. Z. Otwinowski & W. Minor (1997). Methods Enzymol. 276, 307. G.M. Sheldrick (1997). SHELXL97. University of Gottingen, Germany. A.L. Spek (1999). PLATON. Version 1999. Utrecht University, The Netherlands. ;