# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/201 data_koto_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H24 N2' _chemical_formula_weight 244.37 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.4201(17) _cell_length_b 16.681(3) _cell_length_c 21.656(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3041.8(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 30 _exptl_crystal_description quader _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.067 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.063 _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 293(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 48 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10124 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2678 _reflns_number_gt 1655 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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 [0.00000+1.00000exp(5.00(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0631P)^2^+0.0000sin\q/\l] where P = 0.33333Fo^2^ + 0.66667Fc^2^ ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0057(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2678 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.1043 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 1.281 _refine_ls_restrained_S_all 1.281 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.05236(17) 0.83403(9) 0.39179(6) 0.0378(4) Uani 1 1 d . . . N2 N 0.16889(16) 0.78429(8) 0.36877(6) 0.0346(3) Uani 1 1 d . . . C1 C 0.0111(2) 0.83859(10) 0.45385(8) 0.0391(4) Uani 1 1 d . . . C2 C -0.0982(2) 0.89833(10) 0.45850(8) 0.0408(4) Uani 1 1 d . . . C3 C -0.1222(2) 0.93160(10) 0.39820(8) 0.0382(4) Uani 1 1 d . . . C4 C -0.02784(19) 0.89088(10) 0.35763(8) 0.0349(4) Uani 1 1 d . . . C5 C 0.0857(3) 0.78430(16) 0.50011(10) 0.0599(6) Uani 1 1 d . . . H5A H 0.025(3) 0.7851(16) 0.5398(13) 0.085(8) Uiso 1 1 d . . . H5B H 0.201(4) 0.7994(19) 0.5099(14) 0.107(10) Uiso 1 1 d . . . H5C H 0.084(4) 0.727(2) 0.4898(16) 0.131(13) Uiso 1 1 d . . . C6 C -0.1788(3) 0.92620(15) 0.51669(12) 0.0594(6) Uani 1 1 d . . . H6A H -0.298(4) 0.9279(17) 0.5110(13) 0.092(9) Uiso 1 1 d . . . H6B H -0.139(4) 0.9793(18) 0.5320(12) 0.093(9) Uiso 1 1 d . . . H6C H -0.166(4) 0.8872(18) 0.5497(14) 0.097(9) Uiso 1 1 d . . . C7 C -0.2282(3) 1.00137(13) 0.38365(14) 0.0569(6) Uani 1 1 d . . . H7A H -0.332(4) 0.9968(16) 0.4035(12) 0.086(8) Uiso 1 1 d . . . H7B H -0.176(3) 1.0531(17) 0.3997(12) 0.087(8) Uiso 1 1 d . . . H7C H -0.241(3) 1.0080(18) 0.3416(14) 0.094(10) Uiso 1 1 d . . . C8 C -0.0069(3) 0.89646(13) 0.28937(9) 0.0481(5) Uani 1 1 d . . . H8A H -0.064(3) 0.9442(15) 0.2743(10) 0.066(6) Uiso 1 1 d . . . H8B H -0.051(3) 0.8500(15) 0.2683(10) 0.066(7) Uiso 1 1 d . . . H8C H 0.098(3) 0.9010(15) 0.2778(12) 0.074(8) Uiso 1 1 d . . . C9 C 0.3279(2) 0.80455(10) 0.36439(7) 0.0338(4) Uani 1 1 d . . . C10 C 0.4036(2) 0.73909(10) 0.34021(7) 0.0341(4) Uani 1 1 d . . . C11 C 0.2879(2) 0.67771(10) 0.33066(7) 0.0351(4) Uani 1 1 d . . . C12 C 0.14366(19) 0.70695(10) 0.34875(7) 0.0343(4) Uani 1 1 d . . . C13 C 0.3869(3) 0.88413(13) 0.38505(11) 0.0521(5) Uani 1 1 d . . . H13A H 0.366(4) 0.8956(18) 0.4274(15) 0.104(10) Uiso 1 1 d . . . H13B H 0.347(4) 0.9247(19) 0.3638(14) 0.095(9) Uiso 1 1 d . . . H13C H 0.502(4) 0.886(2) 0.3798(14) 0.113(11) Uiso 1 1 d . . . C14 C 0.5779(2) 0.73164(15) 0.32763(10) 0.0506(5) Uani 1 1 d . . . H14A H 0.628(3) 0.6824(16) 0.3488(12) 0.080(8) Uiso 1 1 d . . . H14B H 0.603(3) 0.7300(14) 0.2818(12) 0.070(7) Uiso 1 1 d . . . H14C H 0.636(3) 0.7790(17) 0.3426(11) 0.077(8) Uiso 1 1 d . . . C15 C 0.3201(3) 0.59482(12) 0.30685(11) 0.0526(5) Uani 1 1 d . . . H15A H 0.374(3) 0.5600(17) 0.3363(13) 0.090(9) Uiso 1 1 d . . . H15B H 0.374(4) 0.592(2) 0.2682(18) 0.134(13) Uiso 1 1 d . . . H15C H 0.212(5) 0.567(2) 0.2957(17) 0.140(13) Uiso 1 1 d . . . C16 C -0.0173(3) 0.67046(15) 0.35047(12) 0.0560(5) Uani 1 1 d . . . H16A H -0.016(3) 0.612(2) 0.3385(13) 0.103(10) Uiso 1 1 d . . . H16B H -0.069(4) 0.680(2) 0.3905(16) 0.113(11) Uiso 1 1 d . . . H16C H -0.085(3) 0.6966(16) 0.3236(12) 0.082(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0365(8) 0.0384(8) 0.0385(7) 0.0005(6) 0.0053(6) 0.0103(6) N2 0.0300(7) 0.0309(7) 0.0429(8) -0.0026(6) 0.0042(6) 0.0032(6) C1 0.0398(9) 0.0394(9) 0.0382(9) 0.0018(7) 0.0064(7) 0.0006(8) C2 0.0403(9) 0.0315(9) 0.0505(10) -0.0042(7) 0.0139(8) -0.0053(8) C3 0.0319(9) 0.0260(8) 0.0567(10) -0.0013(7) 0.0028(8) -0.0021(7) C4 0.0323(8) 0.0298(8) 0.0426(9) 0.0018(7) -0.0037(7) -0.0001(7) C5 0.0705(15) 0.0635(15) 0.0456(11) 0.0144(10) 0.0046(10) 0.0098(12) C6 0.0663(15) 0.0484(12) 0.0636(14) -0.0132(11) 0.0296(12) -0.0068(11) C7 0.0470(13) 0.0327(10) 0.0908(18) 0.0040(11) 0.0056(12) 0.0072(9) C8 0.0589(14) 0.0425(11) 0.0428(11) 0.0011(8) -0.0057(9) 0.0013(10) C9 0.0318(8) 0.0334(8) 0.0363(8) 0.0029(7) -0.0004(7) -0.0017(7) C10 0.0319(9) 0.0374(9) 0.0330(8) 0.0061(6) 0.0011(7) 0.0050(7) C11 0.0437(10) 0.0295(8) 0.0322(8) 0.0028(6) -0.0008(7) 0.0052(7) C12 0.0346(9) 0.0300(8) 0.0382(9) 0.0019(6) -0.0012(6) -0.0019(7) C13 0.0565(13) 0.0392(10) 0.0606(13) -0.0030(10) -0.0032(11) -0.0107(10) C14 0.0352(10) 0.0650(13) 0.0515(11) 0.0095(10) 0.0059(8) 0.0095(10) C15 0.0733(15) 0.0338(10) 0.0507(12) -0.0021(8) 0.0025(11) 0.0124(10) C16 0.0444(11) 0.0557(13) 0.0681(14) -0.0007(11) -0.0003(10) -0.0153(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 N2 1.3783(19) . ? N1 C4 1.379(2) . ? N1 C1 1.390(2) . ? N2 C12 1.378(2) . ? N2 C9 1.384(2) . ? C1 C2 1.360(2) . ? C1 C5 1.490(3) . ? C2 C3 1.433(3) . ? C2 C6 1.505(3) . ? C3 C4 1.365(2) . ? C3 C7 1.501(3) . ? C4 C8 1.492(3) . ? C9 C10 1.369(2) . ? C9 C13 1.486(3) . ? C10 C11 1.428(2) . ? C10 C14 1.498(3) . ? C11 C12 1.366(2) . ? C11 C15 1.501(3) . ? C12 C16 1.486(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 N2 N1 C4 124.63(13) . . ? N2 N1 C1 124.09(13) . . ? C4 N1 C1 111.01(13) . . ? C12 N2 N1 124.60(14) . . ? C12 N2 C9 110.88(13) . . ? N1 N2 C9 124.49(14) . . ? C2 C1 N1 106.30(15) . . ? C2 C1 C5 132.93(17) . . ? N1 C1 C5 120.77(16) . . ? C1 C2 C3 108.16(15) . . ? C1 C2 C6 126.40(19) . . ? C3 C2 C6 125.43(18) . . ? C4 C3 C2 108.17(15) . . ? C4 C3 C7 126.65(18) . . ? C2 C3 C7 125.14(18) . . ? C3 C4 N1 106.35(14) . . ? C3 C4 C8 132.49(17) . . ? N1 C4 C8 121.11(16) . . ? C10 C9 N2 106.37(14) . . ? C10 C9 C13 132.21(17) . . ? N2 C9 C13 121.40(16) . . ? C9 C10 C11 108.05(15) . . ? C9 C10 C14 126.31(17) . . ? C11 C10 C14 125.62(16) . . ? C12 C11 C10 107.99(15) . . ? C12 C11 C15 126.03(18) . . ? C10 C11 C15 125.96(17) . . ? C11 C12 N2 106.71(14) . . ? C11 C12 C16 132.20(17) . . ? N2 C12 C16 121.09(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.145 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.030 data_pyr2hi4 _publ_contact_author_name 'Prof. Dr. G. Henkel' _publ_contact_author_address ; Gerhard-Mercator-Universit\"at Duisburg Institut f\"ur Synthesechemie Lotharstrasse 1 D-47048 Duisburg (Germany) ; _publ_contact_author_phone 'intl-code-49-203-3793186' _publ_contact_author_fax 'intl-code-49-203-3792110' _publ_contact_author_email 'biohenkel@uni-duisburg.de' _audit_creation_method SHELXTL+ _chemical_formula_sum 'C16 H25 I4 N2' _chemical_formula_weight 752.98 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.376(3) _cell_length_b 11.618(5) _cell_length_c 12.271(4) _cell_angle_alpha 86.16(3) _cell_angle_beta 84.31(3) _cell_angle_gamma 72.48(3) _cell_volume 1132.2 _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 18 _cell_measurement_theta_min 20 _cell_measurement_theta_max 40 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 694 _exptl_absorpt_coefficient_mu 5.504 _exptl_absorpt_correction_type 'psi scan' _exptl_absorpt_correction_T_min 0.308 _exptl_absorpt_correction_T_max 0.995 _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4RA' _diffrn_measurement_method '\w scans' _diffrn_standards_number 1 _diffrn_standards_interval_count 99 _diffrn_reflns_number 4940 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4940 _reflns_number_gt 4529 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'P3 (Siemens, 1991)' _computing_cell_refinement 'P3 (Siemens, 1991)' _computing_data_reduction 'P3 (Siemens, 1991)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL PLUS (Sheldrick, 1991)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo)+(0.0001)(Fo^2^)]' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method 'SHELXTL PLUS' _refine_ls_number_reflns 4940 _refine_ls_number_parameters 209 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_gt 0.0382 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv N(1) 0.0480(4) 0.5014(3) 0.7856(3) 0.024(1) C(1) 0.1562(5) 0.5742(3) 0.7803(3) 0.023(1) C(2) 0.0632(5) 0.6872(3) 0.7509(3) 0.024(1) C(3) -0.1015(5) 0.6845(3) 0.7318(4) 0.027(1) C(4) -0.1075(5) 0.5688(3) 0.7503(4) 0.025(1) C(5) 0.3315(5) 0.5242(4) 0.8129(4) 0.030(1) C(6) 0.1192(6) 0.7981(4) 0.7442(4) 0.036(2) C(7) -0.2430(6) 0.7920(4) 0.6986(4) 0.034(2) C(8) -0.2485(5) 0.5140(4) 0.7495(5) 0.038(2) N(2) 0.1082(4) 0.3767(3) 0.7816(3) 0.022(1) C(9) 0.0795(5) 0.3016(4) 0.8601(4) 0.027(1) C(10) 0.1592(6) 0.1792(3) 0.8255(4) 0.031(2) C(11) 0.2341(5) 0.1841(4) 0.7245(4) 0.030(1) C(12) 0.2098(5) 0.3129(3) 0.6874(4) 0.026(1) C(13) -0.0219(7) 0.3374(4) 0.9639(4) 0.039(2) C(14) 0.1541(8) 0.0712(4) 0.8975(5) 0.054(2) C(15) 0.3331(7) 0.0836(4) 0.6533(5) 0.046(2) C(16) 0.1317(6) 0.3571(4) 0.5808(4) 0.036(2) I(1) 0.15620(4) 0.88996(2) 0.40158(3) 0.0372(1) I(2) 0.33536(4) 0.82955(2) 0.18360(3) 0.0309(1) I(3) 0.52095(5) 0.76579(3) -0.02627(3) 0.0464(1) I(4) 0.39964(4) 0.61759(2) 0.48446(3) 0.0315(1) H(5a) 0.3866 0.5861 0.8038 0.086(14) H(5b) 0.3281 0.4967 0.8884 0.086(14) H(5c) 0.3923 0.4577 0.7681 0.086(14) H(6a) 0.2345 0.7768 0.7605 0.063(11) H(6b) 0.1083 0.8344 0.6717 0.063(11) H(6c) 0.0508 0.8544 0.7963 0.063(11) H(7a) -0.3404 0.7670 0.6910 0.037(8) H(7b) -0.2691 0.8518 0.7533 0.037(8) H(7c) -0.2093 0.8258 0.6298 0.037(8) H(8a) -0.3451 0.5733 0.7230 0.054(10) H(8b) -0.2142 0.4464 0.7026 0.054(10) H(8c) -0.2764 0.4872 0.8227 0.054(10) H(12) 0.3173 0.3274 0.6824 0.042(15) H(13a) -0.0597 0.4239 0.9664 0.058(10) H(13b) -0.1173 0.3072 0.9688 0.058(10) H(13c) 0.0448 0.3043 1.0242 0.058(10) H(14a) 0.2139 -0.0008 0.8596 0.093(15) H(14b) 0.2055 0.0726 0.9637 0.093(15) H(14c) 0.0393 0.0724 0.9152 0.093(15) H(15a) 0.3358 0.0074 0.6899 0.081(13) H(15b) 0.2822 0.0904 0.5856 0.081(13) H(15c) 0.4457 0.0886 0.6387 0.081(13) H(16a) 0.1241 0.4408 0.5675 0.049(9) H(16b) 0.2000 0.3110 0.5219 0.049(9) H(16c) 0.0213 0.3475 0.5853 0.049(9) loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N(1) 0.022(2) 0.018(1) 0.033(2) -0.008(1) 0.001(2) -0.003(1) C(1) 0.026(2) 0.024(2) 0.022(2) -0.014(2) 0.002(2) -0.004(2) C(2) 0.032(2) 0.025(2) 0.017(2) -0.014(2) 0.000(2) -0.002(2) C(3) 0.032(2) 0.025(2) 0.025(2) -0.010(2) -0.005(2) -0.002(2) C(4) 0.021(2) 0.026(2) 0.031(2) -0.009(2) 0.000(2) -0.006(2) C(5) 0.025(2) 0.032(2) 0.035(3) -0.012(2) -0.007(2) -0.003(2) C(6) 0.047(3) 0.021(2) 0.044(3) -0.018(2) 0.001(2) -0.001(2) C(7) 0.039(3) 0.028(2) 0.033(3) -0.007(2) -0.005(2) 0.000(2) C(8) 0.026(2) 0.032(2) 0.060(4) -0.014(2) -0.005(2) -0.006(2) N(2) 0.024(2) 0.020(1) 0.022(2) -0.009(1) -0.001(1) -0.002(1) C(9) 0.032(2) 0.030(2) 0.023(2) -0.015(2) 0.000(2) 0.000(2) C(10) 0.039(2) 0.022(2) 0.039(3) -0.015(2) -0.013(2) 0.005(2) C(11) 0.028(2) 0.026(2) 0.037(3) -0.005(2) -0.012(2) -0.008(2) C(12) 0.028(2) 0.030(2) 0.022(2) -0.009(2) -0.001(2) -0.003(2) C(13) 0.050(3) 0.051(3) 0.025(3) -0.028(2) 0.005(2) -0.003(2) C(14) 0.073(4) 0.032(2) 0.065(4) -0.026(3) -0.028(3) 0.017(3) C(15) 0.043(3) 0.033(2) 0.061(4) -0.004(2) -0.006(3) -0.018(2) C(16) 0.040(3) 0.046(3) 0.023(2) -0.014(2) -0.002(2) -0.002(2) I(1) 0.0393(2) 0.0267(2) 0.0399(2) -0.0038(1) 0.0022(1) 0.0020(1) I(2) 0.0324(2) 0.0265(2) 0.0343(2) -0.0074(1) -0.0112(1) 0.0016(1) I(3) 0.0565(2) 0.0513(2) 0.0285(2) -0.0097(2) -0.0094(2) -0.0028(2) I(4) 0.0331(2) 0.0317(2) 0.0280(2) -0.0089(1) 0.0026(1) -0.0006(1) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N(1) C(1) 1.408(6) . N(1) C(4) 1.396(5) . N(1) N(2) 1.386(4) . C(1) C(2) 1.355(5) . C(1) C(5) 1.492(6) . C(2) C(3) 1.432(7) . C(2) C(6) 1.492(7) . C(3) C(4) 1.363(6) . C(3) C(7) 1.506(6) . C(4) C(8) 1.503(7) . N(2) C(9) 1.311(6) . N(2) C(12) 1.466(5) . C(9) C(10) 1.449(6) . C(9) C(13) 1.469(7) . C(10) C(11) 1.338(7) . C(10) C(14) 1.494(7) . C(11) C(12) 1.494(6) . C(11) C(15) 1.491(7) . C(12) C(16) 1.509(7) . C(12) H(12) 0.960 . I(1) I(2) 2.953(1) . I(2) I(3) 2.892(1) . I(4) I(4) 2.768(1) 2_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 C(1) N(1) C(4) 109.8(3) . . C(1) N(1) N(2) 122.1(3) . . C(4) N(1) N(2) 123.2(4) . . N(1) C(1) C(2) 106.3(4) . . N(1) C(1) C(5) 120.9(3) . . C(2) C(1) C(5) 132.6(4) . . C(1) C(2) C(3) 108.8(4) . . C(1) C(2) C(6) 126.0(4) . . C(3) C(2) C(6) 125.1(3) . . C(2) C(3) C(4) 108.2(3) . . C(2) C(3) C(7) 125.4(4) . . C(4) C(3) C(7) 126.5(4) . . N(1) C(4) C(3) 106.7(4) . . N(1) C(4) C(8) 121.1(4) . . C(3) C(4) C(8) 131.8(4) . . N(1) N(2) C(9) 124.4(3) . . N(1) N(2) C(12) 123.8(3) . . C(9) N(2) C(12) 111.8(3) . . N(2) C(9) C(10) 108.6(4) . . N(2) C(9) C(13) 124.9(4) . . C(10) C(9) C(13) 126.5(4) . . C(9) C(10) C(11) 108.6(4) . . C(9) C(10) C(14) 122.3(4) . . C(11) C(10) C(14) 129.1(4) . . C(10) C(11) C(12) 109.6(4) . . C(10) C(11) C(15) 129.5(4) . . C(12) C(11) C(15) 120.9(4) . . N(2) C(12) C(11) 101.5(3) . . N(2) C(12) C(16) 112.3(3) . . N(2) C(12) H(12) 108.0 . . C(11) C(12) H(12) 107.9 . . C(16) C(12) H(12) 107.9 . . C(11) C(12) C(16) 118.6(4) . . I(1) I(2) I(3) 178.0(1) . . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.630 _refine_diff_density_min -1.303 _refine_diff_density_rms 0.132