# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Kwok-yin Wong' _publ_contact_author_address ; Department of Applied Biology and Chemical Technology The Hong Kong Polytechnic University Hunghom Kowloon 000 HONG KONG ; _publ_contact_author_email BCKYWONG@POLYU.EDU.HK _publ_section_title ; A tricarbonyl rhenium(I) complex with a pendant ionic liquid moiety as robust and recyclable catalyst for chemical fixation of carbon dioxide in ionic liquid ; loop_ _publ_author_name 'Kwok-yin Wong.' 'Pak-Ho Chan.' 'Kwong-Chak Cheung.' 'Kam-Han Lee.' ; Wing-Leung Wong ; 'Zhong-Yuan Zhou.' # Attachment 'ReComplex_1.CIF' data_wlw6 _database_code_depnum_ccdc_archive 'CCDC 631247' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 F6 N4 O10 Re S2' _chemical_formula_weight 883.81 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 '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 10.800(2) _cell_length_b 16.235(3) _cell_length_c 18.666(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.601(3) _cell_angle_gamma 90.00 _cell_volume 3193.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 16955 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.838 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1736 _exptl_absorpt_coefficient_mu 4.027 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.724 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS; Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD Area Detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29441 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.53 _reflns_number_total 7313 _reflns_number_gt 5403 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0521P)^2^+8.7890P] 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 7313 _refine_ls_number_parameters 404 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.004 _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 Re1 Re 0.237938(12) 0.443630(8) 0.440376(7) 0.03930(3) Uani 1 1 d . . . S1 S 0.36054(12) 0.44912(8) 0.19138(6) 0.0773(3) Uani 1 1 d . . . S2 S 0.89415(10) 0.17470(7) 0.71600(6) 0.0643(3) Uani 1 1 d . . . O1W O 0.1923(2) 0.37108(15) 0.33838(12) 0.0482(7) Uani 1 1 d . . . H1WA H 0.2279 0.3915 0.3057 0.058 Uiso 1 1 d . . . H1WB H 0.1117 0.3720 0.3204 0.058 Uiso 1 1 d . . . O1 O 0.0100(3) 0.5588(2) 0.3982(2) 0.0932(12) Uani 1 1 d . . . O2 O 0.4072(3) 0.57184(17) 0.38793(17) 0.0749(10) Uani 1 1 d . . . O3 O 0.2945(3) 0.5318(2) 0.58780(16) 0.0751(10) Uani 1 1 d . . . O4 O 0.3067(4) 0.3863(3) 0.2294(2) 0.1180(14) Uani 1 1 d . . . O5 O 0.4448(5) 0.5024(4) 0.2393(3) 0.1865(17) Uani 1 1 d . . . O6 O 0.4045(3) 0.4200(2) 0.13019(17) 0.0891(11) Uani 1 1 d . . . O7 O 0.8347(3) 0.1416(2) 0.64657(16) 0.0820(10) Uani 1 1 d . . . O8 O 0.9872(4) 0.2373(3) 0.7136(3) 0.1285(16) Uani 1 1 d . . . O9 O 0.9380(3) 0.1158(2) 0.77127(17) 0.0853(11) Uani 1 1 d . . . N1 N 0.1334(2) 0.34450(18) 0.47990(13) 0.0412(7) Uani 1 1 d . . . N2 N 0.3155(2) 0.31602(19) 0.57150(14) 0.0434(7) Uani 1 1 d . . . N3 N 0.3890(2) 0.35194(16) 0.46674(14) 0.0385(7) Uani 1 1 d . . . N4 N 0.2493(3) 0.38828(18) 0.82026(15) 0.0686(11) Uani 1 1 d D . . C1 C 0.0106(3) 0.3281(3) 0.4480(2) 0.0626(12) Uani 1 1 d . . . H1A H -0.0273 0.3574 0.4062 0.075 Uiso 1 1 calc R . . C2 C -0.0594(4) 0.2709(3) 0.4743(2) 0.0636(10) Uani 1 1 d . . . H2A H -0.1432 0.2615 0.4505 0.076 Uiso 1 1 calc R . . C3 C -0.0069(4) 0.2270(3) 0.5357(2) 0.0845(15) Uani 1 1 d . . . H3A H -0.0539 0.1879 0.5546 0.101 Uiso 1 1 calc R . . C4 C 0.1180(4) 0.2424(3) 0.5688(2) 0.0615(12) Uani 1 1 d . . . H4A H 0.1565 0.2138 0.6109 0.074 Uiso 1 1 calc R . . C5 C 0.1854(3) 0.3002(2) 0.53920(17) 0.0437(9) Uani 1 1 d . . . C6 C 0.4713(3) 0.3410(2) 0.42208(19) 0.0469(9) Uani 1 1 d . . . H6A H 0.4611 0.3722 0.3794 0.056 Uiso 1 1 calc R . . C7 C 0.5696(4) 0.2853(3) 0.4379(2) 0.0663(10) Uani 1 1 d . . . H7A H 0.6254 0.2797 0.4067 0.080 Uiso 1 1 calc R . . C8 C 0.5845(4) 0.2382(3) 0.5000(2) 0.0658(12) Uani 1 1 d . . . H8A H 0.6510 0.2008 0.5116 0.079 Uiso 1 1 calc R . . C9 C 0.5009(3) 0.2467(2) 0.5448(2) 0.0539(10) Uani 1 1 d . . . H9A H 0.5088 0.2143 0.5866 0.065 Uiso 1 1 calc R . . C10 C 0.4039(3) 0.3043(2) 0.52720(17) 0.0406(8) Uani 1 1 d . . . C11 C 0.3595(3) 0.3021(2) 0.65131(17) 0.0513(10) Uani 1 1 d . . . H11A H 0.4500 0.3124 0.6658 0.062 Uiso 1 1 calc R . . H11B H 0.3443 0.2453 0.6629 0.062 Uiso 1 1 calc R . . C12 C 0.2889(4) 0.3595(3) 0.69379(18) 0.0590(11) Uani 1 1 d . . . H12A H 0.3223 0.4149 0.6931 0.071 Uiso 1 1 calc R . . H12B H 0.1998 0.3608 0.6696 0.071 Uiso 1 1 calc R . . C13 C 0.3012(5) 0.3332(3) 0.7701(2) 0.0768(10) Uani 1 1 d . . . H13A H 0.3907 0.3249 0.7912 0.092 Uiso 1 1 calc R . . H13B H 0.2601 0.2800 0.7696 0.092 Uiso 1 1 calc R . . C14 C 0.3306(6) 0.4565(3) 0.8446(3) 0.173(2) Uani 1 1 d D . . H14A H 0.2994 0.5056 0.8169 0.208 Uiso 1 1 calc R . . H14B H 0.4159 0.4452 0.8383 0.208 Uiso 1 1 calc R . . C15 C 0.3303(6) 0.4682(5) 0.9260(3) 0.198(4) Uani 1 1 d D . . H15A H 0.4137 0.4568 0.9562 0.238 Uiso 1 1 calc R . . H15B H 0.3070 0.5243 0.9353 0.238 Uiso 1 1 calc R . . C16 C 0.2341(5) 0.4085(3) 0.9432(3) 0.123(2) Uani 1 1 d D . . H16A H 0.1514 0.4339 0.9377 0.148 Uiso 1 1 calc R . . H16B H 0.2605 0.3865 0.9925 0.148 Uiso 1 1 calc R . . C17 C 0.2336(6) 0.3431(3) 0.8864(2) 0.1196(18) Uani 1 1 d D . . H17A H 0.1541 0.3129 0.8768 0.143 Uiso 1 1 calc R . . H17B H 0.3028 0.3046 0.9024 0.143 Uiso 1 1 calc R . . C18 C 0.1177(7) 0.4158(5) 0.7880(4) 0.154(2) Uani 1 1 d . . . H18A H 0.1201 0.4618 0.7560 0.231 Uiso 1 1 calc R . . H18B H 0.0769 0.4320 0.8266 0.231 Uiso 1 1 calc R . . H18C H 0.0713 0.3715 0.7605 0.231 Uiso 1 1 calc R . . C19 C 0.0957(4) 0.5153(3) 0.4128(2) 0.0589(11) Uani 1 1 d . . . C20 C 0.3417(4) 0.5240(2) 0.4059(2) 0.0544(11) Uani 1 1 d . . . C21 C 0.2751(4) 0.4978(2) 0.53291(19) 0.0515(10) Uani 1 1 d . . . C22 C 0.2295(7) 0.5134(4) 0.1516(5) 0.147(3) Uani 1 1 d . . . C23 C 0.7683(6) 0.2283(4) 0.7443(3) 0.109(2) Uani 1 1 d . . . F1 F 0.1757(4) 0.5435(3) 0.2048(3) 0.1735(19) Uani 1 1 d . . . F2 F 0.1396(5) 0.4691(4) 0.1069(4) 0.226(3) Uani 1 1 d . . . F3 F 0.2599(6) 0.5726(3) 0.1146(4) 0.216(3) Uani 1 1 d . . . F4 F 0.7202(5) 0.2865(3) 0.7019(2) 0.1982(19) Uani 1 1 d . . . F5 F 0.6760(4) 0.1761(4) 0.7494(3) 0.208(2) Uani 1 1 d . . . F6 F 0.8096(4) 0.2631(3) 0.8097(3) 0.1790(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 Re1 0.03827(6) 0.04399(7) 0.03368(6) 0.00001(6) 0.00360(5) 0.00056(6) S1 0.0826(6) 0.0902(8) 0.0706(6) -0.0244(5) 0.0418(5) -0.0162(6) S2 0.0577(5) 0.0714(6) 0.0564(5) -0.0036(5) -0.0034(5) -0.0108(5) O1W 0.0448(11) 0.0591(14) 0.0391(11) -0.0032(11) 0.0062(9) -0.0094(11) O1 0.086(2) 0.092(2) 0.094(2) 0.0027(18) 0.0021(19) 0.0450(17) O2 0.0928(19) 0.0600(16) 0.0721(18) 0.0044(14) 0.0183(16) -0.0288(15) O3 0.102(2) 0.0734(18) 0.0475(14) -0.0163(14) 0.0113(15) -0.0130(17) O4 0.145(2) 0.123(3) 0.112(2) 0.004(2) 0.0878(18) -0.001(3) O5 0.154(4) 0.241(4) 0.183(3) -0.144(3) 0.077(3) -0.101(3) O6 0.110(2) 0.098(2) 0.0722(17) -0.0126(17) 0.0494(15) 0.002(2) O7 0.098(2) 0.093(2) 0.0500(15) -0.0022(15) 0.0054(15) -0.0301(18) O8 0.109(2) 0.135(3) 0.136(3) -0.012(3) 0.016(2) -0.064(2) O9 0.095(2) 0.090(2) 0.0635(18) 0.0003(17) 0.0005(17) 0.0066(19) N1 0.0297(11) 0.0612(17) 0.0320(12) -0.0003(12) 0.0056(10) -0.0053(12) N2 0.0357(12) 0.0613(17) 0.0321(12) 0.0052(12) 0.0051(10) -0.0014(13) N3 0.0313(11) 0.0477(15) 0.0355(12) 0.0028(11) 0.0049(10) -0.0035(11) N4 0.110(3) 0.0491(17) 0.0372(15) -0.0062(14) -0.0040(17) 0.0270(18) C1 0.0338(16) 0.111(3) 0.0398(17) 0.008(2) 0.0013(14) -0.009(2) C2 0.0541(19) 0.062(2) 0.072(2) 0.010(2) 0.0084(18) -0.0207(18) C3 0.059(2) 0.131(4) 0.066(2) 0.017(3) 0.0198(18) -0.038(2) C4 0.058(2) 0.079(3) 0.0478(19) 0.0119(19) 0.0119(16) -0.012(2) C5 0.0361(14) 0.061(2) 0.0358(15) 0.0008(14) 0.0109(12) -0.0046(14) C6 0.0373(14) 0.059(2) 0.0480(16) 0.0038(16) 0.0166(13) -0.0058(15) C7 0.069(3) 0.071(3) 0.067(2) 0.008(2) 0.0346(16) 0.005(2) C8 0.0538(19) 0.071(2) 0.075(2) 0.009(2) 0.0176(18) 0.0239(19) C9 0.0481(18) 0.054(2) 0.058(2) 0.0103(17) 0.0088(16) 0.0076(16) C10 0.0397(15) 0.0428(17) 0.0373(15) 0.0003(13) 0.0038(13) -0.0074(13) C11 0.0472(18) 0.070(2) 0.0338(16) 0.0058(16) 0.0023(14) 0.0036(17) C12 0.062(2) 0.077(3) 0.0371(17) 0.0081(17) 0.0070(16) 0.013(2) C13 0.107(2) 0.066(2) 0.054(2) -0.002(2) 0.011(2) 0.040(2) C14 0.162(4) 0.184(4) 0.209(4) -0.155(3) 0.117(3) -0.102(4) C15 0.189(9) 0.202(8) 0.175(8) -0.078(6) -0.025(7) -0.025(8) C16 0.137(6) 0.163(6) 0.076(3) -0.012(3) 0.035(3) 0.055(4) C17 0.161(4) 0.109(4) 0.106(4) 0.025(3) 0.068(3) 0.014(4) C18 0.182(5) 0.172(5) 0.101(4) -0.057(4) 0.016(4) 0.071(5) C19 0.057(2) 0.064(2) 0.050(2) 0.0002(19) 0.0008(17) 0.0150(19) C20 0.067(2) 0.0474(19) 0.0420(18) -0.0037(16) -0.0042(17) -0.0040(18) C21 0.0580(19) 0.055(2) 0.0384(16) -0.0007(16) 0.0046(15) 0.0022(17) C22 0.187(5) 0.092(4) 0.198(6) -0.024(4) 0.117(4) -0.023(4) C23 0.113(4) 0.118(4) 0.077(3) -0.010(3) -0.020(3) 0.029(4) F1 0.149(3) 0.164(3) 0.227(4) -0.050(3) 0.083(3) 0.045(3) F2 0.141(4) 0.239(5) 0.257(6) -0.078(5) -0.042(4) 0.061(4) F3 0.209(3) 0.139(3) 0.318(7) 0.061(4) 0.097(4) 0.062(3) F4 0.235(4) 0.172(3) 0.142(3) -0.010(3) -0.058(3) 0.133(3) F5 0.154(6) 0.238(6) 0.268(4) -0.038(4) 0.125(3) -0.010(4) F6 0.166(3) 0.165(3) 0.185(3) -0.065(3) -0.006(3) 0.083(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 Re1 C21 1.901(4) . ? Re1 C19 1.907(4) . ? Re1 C20 1.919(4) . ? Re1 N3 2.184(3) . ? Re1 N1 2.185(3) . ? Re1 O1W 2.201(2) . ? S1 O6 1.410(4) . ? S1 O5 1.422(5) . ? S1 O4 1.436(4) . ? S1 C22 1.785(8) . ? S2 O9 1.411(3) . ? S2 O7 1.420(3) . ? S2 O8 1.438(4) . ? S2 C23 1.788(7) . ? O1W H1WA 0.8555 . ? O1W H1WB 0.8618 . ? O1 C19 1.149(5) . ? O2 C20 1.150(5) . ? O3 C21 1.142(5) . ? N1 C5 1.337(4) . ? N1 C1 1.356(4) . ? N2 C10 1.406(4) . ? N2 C5 1.426(4) . ? N2 C11 1.479(4) . ? N3 C10 1.349(4) . ? N3 C6 1.356(4) . ? N4 C14 1.424(5) . ? N4 C18 1.486(8) . ? N4 C13 1.490(5) . ? N4 C17 1.478(5) . ? C1 C2 1.355(6) . ? C1 H1A 0.9300 . ? C2 C3 1.362(6) . ? C2 H2A 0.9300 . ? C3 C4 1.378(5) . ? C3 H3A 0.9300 . ? C4 C5 1.375(5) . ? C4 H4A 0.9300 . ? C6 C7 1.377(5) . ? C6 H6A 0.9300 . ? C7 C8 1.367(6) . ? C7 H7A 0.9300 . ? C8 C9 1.365(6) . ? C8 H8A 0.9300 . ? C9 C10 1.389(5) . ? C9 H9A 0.9300 . ? C11 C12 1.530(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.465(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.533(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.506(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.499(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C22 F3 1.268(9) . ? C22 F2 1.343(9) . ? C22 F1 1.348(9) . ? C23 F4 1.268(7) . ? C23 F5 1.328(8) . ? C23 F6 1.331(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 Re1 C19 87.75(16) . . ? C21 Re1 C20 88.10(16) . . ? C19 Re1 C20 89.40(18) . . ? C21 Re1 N3 96.39(13) . . ? C19 Re1 N3 174.45(14) . . ? C20 Re1 N3 94.41(14) . . ? C21 Re1 N1 93.22(14) . . ? C19 Re1 N1 95.47(15) . . ? C20 Re1 N1 175.00(14) . . ? N3 Re1 N1 80.65(10) . . ? C21 Re1 O1W 175.02(13) . . ? C19 Re1 O1W 94.47(13) . . ? C20 Re1 O1W 96.37(13) . . ? N3 Re1 O1W 81.11(9) . . ? N1 Re1 O1W 82.14(9) . . ? O6 S1 O5 115.5(3) . . ? O6 S1 O4 114.0(2) . . ? O5 S1 O4 113.2(3) . . ? O6 S1 C22 103.6(3) . . ? O5 S1 C22 104.3(3) . . ? O4 S1 C22 104.6(3) . . ? O9 S2 O7 115.1(2) . . ? O9 S2 O8 112.1(2) . . ? O7 S2 O8 114.7(2) . . ? O9 S2 C23 105.6(3) . . ? O7 S2 C23 103.4(2) . . ? O8 S2 C23 104.3(3) . . ? Re1 O1W H1WA 111.0 . . ? Re1 O1W H1WB 110.1 . . ? H1WA O1W H1WB 106.7 . . ? C5 N1 C1 116.8(3) . . ? C5 N1 Re1 121.4(2) . . ? C1 N1 Re1 121.7(2) . . ? C10 N2 C5 117.4(3) . . ? C10 N2 C11 117.5(3) . . ? C5 N2 C11 117.9(3) . . ? C10 N3 C6 117.7(3) . . ? C10 N3 Re1 121.8(2) . . ? C6 N3 Re1 120.6(2) . . ? C14 N4 C18 111.3(4) . . ? C14 N4 C13 112.1(4) . . ? C18 N4 C13 112.5(4) . . ? C14 N4 C17 107.2(3) . . ? C18 N4 C17 102.4(5) . . ? C13 N4 C17 110.8(3) . . ? C2 C1 N1 123.1(4) . . ? C2 C1 H1A 118.5 . . ? N1 C1 H1A 118.5 . . ? C1 C2 C3 120.0(4) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? C2 C3 C4 118.0(4) . . ? C2 C3 H3A 121.0 . . ? C4 C3 H3A 121.0 . . ? C5 C4 C3 119.7(4) . . ? C5 C4 H4A 120.1 . . ? C3 C4 H4A 120.1 . . ? N1 C5 C4 122.4(3) . . ? N1 C5 N2 116.8(3) . . ? C4 C5 N2 120.8(3) . . ? N3 C6 C7 122.1(3) . . ? N3 C6 H6A 118.9 . . ? C7 C6 H6A 118.9 . . ? C8 C7 C6 119.5(4) . . ? C8 C7 H7A 120.3 . . ? C6 C7 H7A 120.3 . . ? C9 C8 C7 119.5(4) . . ? C9 C8 H8A 120.3 . . ? C7 C8 H8A 120.3 . . ? C8 C9 C10 119.2(4) . . ? C8 C9 H9A 120.4 . . ? C10 C9 H9A 120.4 . . ? N3 C10 C9 122.0(3) . . ? N3 C10 N2 116.3(3) . . ? C9 C10 N2 121.7(3) . . ? N2 C11 C12 110.0(3) . . ? N2 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? N2 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C13 C12 C11 112.1(3) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 C13 N4 118.0(3) . . ? C12 C13 H13A 107.8 . . ? N4 C13 H13A 107.8 . . ? C12 C13 H13B 107.8 . . ? N4 C13 H13B 107.8 . . ? H13A C13 H13B 107.2 . . ? N4 C14 C15 106.1(4) . . ? N4 C14 H14A 110.5 . . ? C15 C14 H14A 110.5 . . ? N4 C14 H14B 110.5 . . ? C15 C14 H14B 110.5 . . ? H14A C14 H14B 108.7 . . ? C16 C15 C14 106.4(5) . . ? C16 C15 H15A 110.5 . . ? C14 C15 H15A 110.5 . . ? C16 C15 H15B 110.5 . . ? C14 C15 H15B 110.5 . . ? H15A C15 H15B 108.6 . . ? C15 C16 C17 101.7(5) . . ? C15 C16 H16A 111.4 . . ? C17 C16 H16A 111.4 . . ? C15 C16 H16B 111.4 . . ? C17 C16 H16B 111.4 . . ? H16A C16 H16B 109.3 . . ? C16 C17 N4 104.8(4) . . ? C16 C17 H17A 110.8 . . ? N4 C17 H17A 110.8 . . ? C16 C17 H17B 110.8 . . ? N4 C17 H17B 110.8 . . ? H17A C17 H17B 108.9 . . ? N4 C18 H18A 109.5 . . ? N4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1 C19 Re1 178.2(4) . . ? O2 C20 Re1 177.3(3) . . ? O3 C21 Re1 178.0(4) . . ? F3 C22 F2 107.8(7) . . ? F3 C22 F1 109.3(6) . . ? F2 C22 F1 106.4(7) . . ? F3 C22 S1 113.2(6) . . ? F2 C22 S1 110.2(5) . . ? F1 C22 S1 109.6(6) . . ? F4 C23 F5 108.0(5) . . ? F4 C23 F6 105.4(5) . . ? F5 C23 F6 108.2(6) . . ? F4 C23 S2 114.3(5) . . ? F5 C23 S2 109.9(5) . . ? F6 C23 S2 110.7(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 Re1 N1 C5 -54.1(3) . . . . ? C19 Re1 N1 C5 -142.2(3) . . . . ? C20 Re1 N1 C5 51.1(15) . . . . ? N3 Re1 N1 C5 41.9(3) . . . . ? O1W Re1 N1 C5 124.1(3) . . . . ? C21 Re1 N1 C1 122.2(3) . . . . ? C19 Re1 N1 C1 34.1(3) . . . . ? C20 Re1 N1 C1 -132.6(14) . . . . ? N3 Re1 N1 C1 -141.9(3) . . . . ? O1W Re1 N1 C1 -59.7(3) . . . . ? C21 Re1 N3 C10 52.3(3) . . . . ? C19 Re1 N3 C10 -85.9(15) . . . . ? C20 Re1 N3 C10 140.9(2) . . . . ? N1 Re1 N3 C10 -39.9(2) . . . . ? O1W Re1 N3 C10 -123.3(2) . . . . ? C21 Re1 N3 C6 -127.9(3) . . . . ? C19 Re1 N3 C6 93.9(15) . . . . ? C20 Re1 N3 C6 -39.3(3) . . . . ? N1 Re1 N3 C6 139.9(2) . . . . ? O1W Re1 N3 C6 56.5(2) . . . . ? C5 N1 C1 C2 1.1(6) . . . . ? Re1 N1 C1 C2 -175.3(3) . . . . ? N1 C1 C2 C3 0.3(7) . . . . ? C1 C2 C3 C4 -0.6(7) . . . . ? C2 C3 C4 C5 -0.4(7) . . . . ? C1 N1 C5 C4 -2.2(5) . . . . ? Re1 N1 C5 C4 174.3(3) . . . . ? C1 N1 C5 N2 178.4(3) . . . . ? Re1 N1 C5 N2 -5.2(4) . . . . ? C3 C4 C5 N1 1.9(6) . . . . ? C3 C4 C5 N2 -178.7(4) . . . . ? C10 N2 C5 N1 -59.3(4) . . . . ? C11 N2 C5 N1 151.0(3) . . . . ? C10 N2 C5 C4 121.2(4) . . . . ? C11 N2 C5 C4 -28.5(5) . . . . ? C10 N3 C6 C7 -1.9(5) . . . . ? Re1 N3 C6 C7 178.3(3) . . . . ? N3 C6 C7 C8 1.0(6) . . . . ? C6 C7 C8 C9 0.7(6) . . . . ? C7 C8 C9 C10 -1.4(6) . . . . ? C6 N3 C10 C9 1.1(5) . . . . ? Re1 N3 C10 C9 -179.1(2) . . . . ? C6 N3 C10 N2 -178.8(3) . . . . ? Re1 N3 C10 N2 1.0(4) . . . . ? C8 C9 C10 N3 0.5(5) . . . . ? C8 C9 C10 N2 -179.6(3) . . . . ? C5 N2 C10 N3 61.5(4) . . . . ? C11 N2 C10 N3 -148.7(3) . . . . ? C5 N2 C10 C9 -118.4(4) . . . . ? C11 N2 C10 C9 31.4(5) . . . . ? C10 N2 C11 C12 148.2(3) . . . . ? C5 N2 C11 C12 -62.2(4) . . . . ? N2 C11 C12 C13 163.8(3) . . . . ? C11 C12 C13 N4 173.4(4) . . . . ? C14 N4 C13 C12 -77.7(5) . . . . ? C18 N4 C13 C12 48.8(6) . . . . ? C17 N4 C13 C12 162.7(4) . . . . ? C18 N4 C14 C15 93.5(5) . . . . ? C13 N4 C14 C15 -139.4(4) . . . . ? C17 N4 C14 C15 -17.7(6) . . . . ? N4 C14 C15 C16 -5.7(7) . . . . ? C14 C15 C16 C17 25.8(6) . . . . ? C15 C16 C17 N4 -36.6(6) . . . . ? C14 N4 C17 C16 34.8(6) . . . . ? C18 N4 C17 C16 -82.4(5) . . . . ? C13 N4 C17 C16 157.4(4) . . . . ? C21 Re1 C19 O1 -23(12) . . . . ? C20 Re1 C19 O1 -111(12) . . . . ? N3 Re1 C19 O1 115(12) . . . . ? N1 Re1 C19 O1 70(12) . . . . ? O1W Re1 C19 O1 152(12) . . . . ? C21 Re1 C20 O2 42(8) . . . . ? C19 Re1 C20 O2 130(8) . . . . ? N3 Re1 C20 O2 -54(8) . . . . ? N1 Re1 C20 O2 -63(9) . . . . ? O1W Re1 C20 O2 -135(8) . . . . ? C19 Re1 C21 O3 -1(11) . . . . ? C20 Re1 C21 O3 88(11) . . . . ? N3 Re1 C21 O3 -178(100) . . . . ? N1 Re1 C21 O3 -97(11) . . . . ? O1W Re1 C21 O3 -118(11) . . . . ? O6 S1 C22 F3 -59.5(7) . . . . ? O5 S1 C22 F3 61.7(7) . . . . ? O4 S1 C22 F3 -179.2(6) . . . . ? O6 S1 C22 F2 61.3(6) . . . . ? O5 S1 C22 F2 -177.4(6) . . . . ? O4 S1 C22 F2 -58.4(7) . . . . ? O6 S1 C22 F1 178.1(4) . . . . ? O5 S1 C22 F1 -60.7(6) . . . . ? O4 S1 C22 F1 58.4(5) . . . . ? O9 S2 C23 F4 177.4(4) . . . . ? O7 S2 C23 F4 -61.3(5) . . . . ? O8 S2 C23 F4 59.0(5) . . . . ? O9 S2 C23 F5 -61.0(5) . . . . ? O7 S2 C23 F5 60.3(5) . . . . ? O8 S2 C23 F5 -179.3(4) . . . . ? O9 S2 C23 F6 58.5(5) . . . . ? O7 S2 C23 F6 179.8(4) . . . . ? O8 S2 C23 F6 -59.8(5) . . . . ? 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 O1W H1WA O4 0.86 1.81 2.611(5) 154.5 . O1W H1WB O9 0.86 1.91 2.767(4) 172.4 4_465 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.091 _refine_diff_density_min -0.710 _refine_diff_density_rms 0.129 data_wlw1 _database_code_depnum_ccdc_archive 'CCDC 632736' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H25 I N4' _chemical_formula_sum 'C18 H25 I N4' _chemical_formula_weight 424.32 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' I I -0.4742 1.8119 '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 10.756(2) _cell_length_b 9.1086(19) _cell_length_c 19.236(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.476(4) _cell_angle_gamma 90.00 _cell_volume 1878.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 10554 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 1.710 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.724 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS; Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD Area Detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17082 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.57 _reflns_number_total 4337 _reflns_number_gt 3321 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0365P)^2^+0.4169P] 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 4337 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0750 _refine_ls_wR_factor_gt 0.0685 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 I1 I 0.744064(16) 0.380367(18) 0.637030(9) 0.05304(8) Uani 1 1 d . . . N1 N 0.3422(2) 0.1023(2) 0.68009(10) 0.0450(5) Uani 1 1 d . . . N2 N 0.57172(17) 0.35759(19) 0.83872(9) 0.0363(4) Uani 1 1 d . . . N3 N 0.3339(2) -0.0602(3) 0.58692(11) 0.0528(5) Uani 1 1 d . . . N4 N 0.1681(2) 0.2455(3) 0.64441(12) 0.0555(6) Uani 1 1 d . . . C1 C 0.3121(3) 0.1078(3) 0.75287(13) 0.0521(6) Uani 1 1 d . . . H1A H 0.3405 0.0178 0.7759 0.063 Uiso 1 1 calc R . . H1B H 0.2222 0.1126 0.7543 0.063 Uiso 1 1 calc R . . C2 C 0.3701(2) 0.2374(3) 0.79272(14) 0.0505(6) Uani 1 1 d . . . H2A H 0.3450 0.3274 0.7686 0.061 Uiso 1 1 calc R . . H2B H 0.3391 0.2406 0.8387 0.061 Uiso 1 1 calc R . . C3 C 0.5109(2) 0.2290(3) 0.80021(12) 0.0419(5) Uani 1 1 d . . . H3A H 0.5356 0.1394 0.8248 0.050 Uiso 1 1 calc R . . H3B H 0.5414 0.2238 0.7541 0.050 Uiso 1 1 calc R . . C4 C 0.7108(2) 0.3339(3) 0.85002(13) 0.0447(5) Uani 1 1 d . . . H4A H 0.7515 0.3577 0.8082 0.054 Uiso 1 1 calc R . . H4B H 0.7295 0.2328 0.8627 0.054 Uiso 1 1 calc R . . C5 C 0.7534(2) 0.4378(3) 0.90950(14) 0.0522(6) Uani 1 1 d . . . H5A H 0.7855 0.5284 0.8914 0.063 Uiso 1 1 calc R . . H5B H 0.8183 0.3925 0.9402 0.063 Uiso 1 1 calc R . . C6 C 0.6374(3) 0.4671(4) 0.94830(14) 0.0602(7) Uani 1 1 d . . . H6A H 0.6514 0.4386 0.9969 0.072 Uiso 1 1 calc R . . H6B H 0.6155 0.5704 0.9460 0.072 Uiso 1 1 calc R . . C7 C 0.5344(3) 0.3743(3) 0.91142(13) 0.0530(7) Uani 1 1 d . . . H7A H 0.5289 0.2793 0.9338 0.064 Uiso 1 1 calc R . . H7B H 0.4544 0.4233 0.9117 0.064 Uiso 1 1 calc R . . C8 C 0.5488(3) 0.4973(3) 0.79832(14) 0.0543(7) Uani 1 1 d . . . H8A H 0.4637 0.5273 0.8008 0.081 Uiso 1 1 calc R . . H8B H 0.5648 0.4813 0.7505 0.081 Uiso 1 1 calc R . . H8C H 0.6034 0.5727 0.8178 0.081 Uiso 1 1 calc R . . C9 C 0.3805(2) -0.0301(3) 0.65134(12) 0.0408(5) Uani 1 1 d . . . C10 C 0.4631(2) -0.1245(3) 0.68885(16) 0.0568(7) Uani 1 1 d . . . H10 H 0.4959 -0.1005 0.7336 0.068 Uiso 1 1 calc R . . C11 C 0.4945(3) -0.2533(3) 0.65798(19) 0.0682(9) Uani 1 1 d . . . H11 H 0.5488 -0.3185 0.6820 0.082 Uiso 1 1 calc R . . C12 C 0.4464(3) -0.2866(3) 0.5919(2) 0.0725(9) Uani 1 1 d . . . H12 H 0.4660 -0.3744 0.5706 0.087 Uiso 1 1 calc R . . C13 C 0.3689(3) -0.1867(3) 0.55839(18) 0.0681(8) Uani 1 1 d . . . H13 H 0.3383 -0.2075 0.5129 0.082 Uiso 1 1 calc R . . C14 C 0.2840(2) 0.2080(3) 0.63409(12) 0.0404(5) Uani 1 1 d . . . C15 C 0.3504(2) 0.2704(3) 0.58228(14) 0.0535(6) Uani 1 1 d . . . H15 H 0.4327 0.2436 0.5774 0.064 Uiso 1 1 calc R . . C16 C 0.2920(3) 0.3720(3) 0.53861(17) 0.0636(8) Uani 1 1 d . . . H16 H 0.3336 0.4142 0.5030 0.076 Uiso 1 1 calc R . . C17 C 0.1705(3) 0.4107(3) 0.54825(17) 0.0647(8) Uani 1 1 d . . . H17 H 0.1286 0.4792 0.5192 0.078 Uiso 1 1 calc R . . C18 C 0.1138(3) 0.3469(4) 0.60075(17) 0.0655(8) Uani 1 1 d . . . H18 H 0.0322 0.3746 0.6072 0.079 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 I1 0.06267(13) 0.04611(11) 0.05065(12) -0.00100(8) 0.00644(8) 0.00273(8) N1 0.0554(12) 0.0477(12) 0.0307(10) -0.0002(8) -0.0039(9) -0.0038(9) N2 0.0400(10) 0.0362(10) 0.0315(9) -0.0016(8) -0.0037(8) 0.0047(8) N3 0.0601(13) 0.0487(12) 0.0471(13) -0.0076(10) -0.0102(10) 0.0071(10) N4 0.0502(13) 0.0686(15) 0.0476(13) -0.0021(11) 0.0039(10) 0.0035(11) C1 0.0543(15) 0.0678(18) 0.0332(12) -0.0026(12) -0.0030(11) -0.0131(12) C2 0.0441(13) 0.0630(16) 0.0434(14) -0.0124(12) -0.0021(11) -0.0002(12) C3 0.0466(13) 0.0386(12) 0.0391(12) -0.0054(10) -0.0054(10) 0.0045(10) C4 0.0398(12) 0.0443(13) 0.0485(14) -0.0016(11) -0.0055(10) 0.0053(10) C5 0.0508(15) 0.0556(15) 0.0480(15) -0.0050(13) -0.0104(12) -0.0020(12) C6 0.0606(17) 0.0751(19) 0.0430(15) -0.0159(14) -0.0083(13) 0.0038(14) C7 0.0521(15) 0.0725(19) 0.0344(13) -0.0093(12) 0.0024(11) -0.0008(13) C8 0.0657(17) 0.0413(14) 0.0535(16) 0.0078(12) -0.0111(13) 0.0089(12) C9 0.0375(12) 0.0441(13) 0.0399(13) 0.0056(10) -0.0021(10) -0.0046(10) C10 0.0443(14) 0.0695(19) 0.0556(16) 0.0217(14) -0.0027(12) -0.0008(13) C11 0.0506(16) 0.0553(18) 0.101(3) 0.0371(18) 0.0186(17) 0.0117(13) C12 0.073(2) 0.0463(16) 0.102(3) -0.0016(17) 0.027(2) 0.0052(15) C13 0.078(2) 0.0580(18) 0.068(2) -0.0163(15) 0.0055(16) 0.0035(16) C14 0.0468(13) 0.0376(12) 0.0361(12) -0.0048(9) -0.0005(10) -0.0056(10) C15 0.0486(14) 0.0566(16) 0.0558(16) 0.0083(13) 0.0060(12) -0.0007(12) C16 0.073(2) 0.0545(17) 0.0625(18) 0.0163(14) 0.0038(15) -0.0042(15) C17 0.077(2) 0.0518(16) 0.0631(19) 0.0002(14) -0.0117(16) 0.0139(14) C18 0.0538(16) 0.078(2) 0.0634(19) -0.0081(16) -0.0055(14) 0.0160(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 C9 1.402(3) . ? N1 C14 1.420(3) . ? N1 C1 1.462(3) . ? N2 C7 1.492(3) . ? N2 C8 1.501(3) . ? N2 C3 1.507(3) . ? N2 C4 1.510(3) . ? N3 C9 1.329(3) . ? N3 C13 1.343(4) . ? N4 C14 1.322(3) . ? N4 C18 1.351(4) . ? C1 C2 1.515(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.511(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.527(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.527(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.524(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.395(3) . ? C10 C11 1.369(4) . ? C10 H10 0.9300 . ? C11 C12 1.368(5) . ? C11 H11 0.9300 . ? C12 C13 1.362(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.392(3) . ? C15 C16 1.369(4) . ? C15 H15 0.9300 . ? C16 C17 1.380(5) . ? C16 H16 0.9300 . ? C17 C18 1.351(5) . ? C17 H17 0.9300 . ? C18 H18 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 C9 N1 C14 117.82(19) . . ? C9 N1 C1 120.1(2) . . ? C14 N1 C1 117.0(2) . . ? C7 N2 C8 110.71(19) . . ? C7 N2 C3 113.65(19) . . ? C8 N2 C3 110.90(18) . . ? C7 N2 C4 102.44(18) . . ? C8 N2 C4 108.41(19) . . ? C3 N2 C4 110.31(17) . . ? C9 N3 C13 117.4(2) . . ? C14 N4 C18 116.8(2) . . ? N1 C1 C2 113.5(2) . . ? N1 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? N1 C1 H1B 108.9 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C3 C2 C1 112.3(2) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? N2 C3 C2 113.65(19) . . ? N2 C3 H3A 108.8 . . ? C2 C3 H3A 108.8 . . ? N2 C3 H3B 108.8 . . ? C2 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? N2 C4 C5 104.81(19) . . ? N2 C4 H4A 110.8 . . ? C5 C4 H4A 110.8 . . ? N2 C4 H4B 110.8 . . ? C5 C4 H4B 110.8 . . ? H4A C4 H4B 108.9 . . ? C4 C5 C6 105.4(2) . . ? C4 C5 H5A 110.7 . . ? C6 C5 H5A 110.7 . . ? C4 C5 H5B 110.7 . . ? C6 C5 H5B 110.7 . . ? H5A C5 H5B 108.8 . . ? C7 C6 C5 105.5(2) . . ? C7 C6 H6A 110.6 . . ? C5 C6 H6A 110.6 . . ? C7 C6 H6B 110.6 . . ? C5 C6 H6B 110.6 . . ? H6A C6 H6B 108.8 . . ? N2 C7 C6 104.7(2) . . ? N2 C7 H7A 110.8 . . ? C6 C7 H7A 110.8 . . ? N2 C7 H7B 110.8 . . ? C6 C7 H7B 110.8 . . ? H7A C7 H7B 108.9 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 C10 122.3(2) . . ? N3 C9 N1 116.3(2) . . ? C10 C9 N1 121.4(2) . . ? C11 C10 C9 118.1(3) . . ? C11 C10 H10 120.9 . . ? C9 C10 H10 120.9 . . ? C12 C11 C10 120.3(3) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 117.7(3) . . ? C13 C12 H12 121.2 . . ? C11 C12 H12 121.2 . . ? N3 C13 C12 124.1(3) . . ? N3 C13 H13 118.0 . . ? C12 C13 H13 118.0 . . ? N4 C14 C15 123.0(2) . . ? N4 C14 N1 117.2(2) . . ? C15 C14 N1 119.8(2) . . ? C16 C15 C14 118.6(3) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C17 119.0(3) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C18 C17 C16 118.6(3) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? C17 C18 N4 124.0(3) . . ? C17 C18 H18 118.0 . . ? N4 C18 H18 118.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 C1 C2 133.6(2) . . . . ? C14 N1 C1 C2 -72.3(3) . . . . ? N1 C1 C2 C3 -65.2(3) . . . . ? C7 N2 C3 C2 60.2(3) . . . . ? C8 N2 C3 C2 -65.3(3) . . . . ? C4 N2 C3 C2 174.6(2) . . . . ? C1 C2 C3 N2 179.1(2) . . . . ? C7 N2 C4 C5 -39.0(2) . . . . ? C8 N2 C4 C5 78.0(2) . . . . ? C3 N2 C4 C5 -160.4(2) . . . . ? N2 C4 C5 C6 22.6(3) . . . . ? C4 C5 C6 C7 2.3(3) . . . . ? C8 N2 C7 C6 -74.9(3) . . . . ? C3 N2 C7 C6 159.5(2) . . . . ? C4 N2 C7 C6 40.5(2) . . . . ? C5 C6 C7 N2 -26.6(3) . . . . ? C13 N3 C9 C10 0.2(4) . . . . ? C13 N3 C9 N1 -179.7(2) . . . . ? C14 N1 C9 N3 -15.3(3) . . . . ? C1 N1 C9 N3 138.6(2) . . . . ? C14 N1 C9 C10 164.8(2) . . . . ? C1 N1 C9 C10 -41.3(3) . . . . ? N3 C9 C10 C11 -1.2(4) . . . . ? N1 C9 C10 C11 178.7(2) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C10 C11 C12 C13 1.0(5) . . . . ? C9 N3 C13 C12 1.6(5) . . . . ? C11 C12 C13 N3 -2.1(5) . . . . ? C18 N4 C14 C15 1.4(4) . . . . ? C18 N4 C14 N1 179.5(2) . . . . ? C9 N1 C14 N4 118.7(2) . . . . ? C1 N1 C14 N4 -36.0(3) . . . . ? C9 N1 C14 C15 -63.1(3) . . . . ? C1 N1 C14 C15 142.1(2) . . . . ? N4 C14 C15 C16 -2.0(4) . . . . ? N1 C14 C15 C16 180.0(2) . . . . ? C14 C15 C16 C17 1.1(4) . . . . ? C15 C16 C17 C18 0.2(5) . . . . ? C16 C17 C18 N4 -0.8(5) . . . . ? C14 N4 C18 C17 0.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.483 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.071