# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers # This journal is © The Partner Organisations 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 N3' _chemical_formula_weight 303.40 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 15.3067(9) _cell_length_b 12.1443(7) _cell_length_c 18.1692(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3377.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9699 _exptl_absorpt_correction_T_max 0.9879 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 37170 _diffrn_reflns_av_R_equivalents 0.0709 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2975 _reflns_number_gt 2058 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0335P)^2^+0.7574P] 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 2975 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.11884(9) 0.61734(11) 0.13589(7) 0.0479(4) Uani 1 1 d . . . N2 N 0.17106(8) 0.68715(10) 0.17490(7) 0.0441(3) Uani 1 1 d . . . N3 N 0.16862(9) 0.53399(10) 0.23864(7) 0.0471(3) Uani 1 1 d . . . C1 C 0.07121(10) 0.42745(13) 0.15484(9) 0.0431(4) Uani 1 1 d . . . C2 C 0.06256(11) 0.33975(13) 0.20267(9) 0.0486(4) Uani 1 1 d . . . H2A H 0.0886 0.3427 0.2489 0.058 Uiso 1 1 calc R . . C3 C 0.01543(12) 0.24761(15) 0.18235(11) 0.0577(5) Uani 1 1 d . . . H3A H 0.0099 0.1890 0.2149 0.069 Uiso 1 1 calc R . . C4 C -0.02330(12) 0.24230(16) 0.11420(11) 0.0624(5) Uani 1 1 d . . . H4A H -0.0557 0.1806 0.1009 0.075 Uiso 1 1 calc R . . C5 C -0.01399(13) 0.32831(16) 0.06581(11) 0.0648(5) Uani 1 1 d . . . H5A H -0.0395 0.3245 0.0194 0.078 Uiso 1 1 calc R . . C6 C 0.03305(12) 0.42007(15) 0.08582(10) 0.0583(5) Uani 1 1 d . . . H6A H 0.0393 0.4778 0.0526 0.070 Uiso 1 1 calc R . . C7 C 0.25613(10) 0.68466(13) 0.29321(8) 0.0423(4) Uani 1 1 d . . . C8 C 0.23999(11) 0.78699(14) 0.32340(9) 0.0508(4) Uani 1 1 d . . . H8A H 0.1927 0.8282 0.3068 0.061 Uiso 1 1 calc R . . C9 C 0.29318(12) 0.82877(15) 0.37791(9) 0.0576(5) Uani 1 1 d . . . H9A H 0.2816 0.8977 0.3979 0.069 Uiso 1 1 calc R . . C10 C 0.36292(12) 0.76888(17) 0.40256(10) 0.0606(5) Uani 1 1 d . . . H10A H 0.3988 0.7972 0.4393 0.073 Uiso 1 1 calc R . . C11 C 0.38002(12) 0.66708(17) 0.37321(10) 0.0607(5) Uani 1 1 d . . . H11A H 0.4279 0.6268 0.3897 0.073 Uiso 1 1 calc R . . C12 C 0.32639(11) 0.62427(14) 0.31926(9) 0.0525(4) Uani 1 1 d . . . H12A H 0.3375 0.5545 0.3003 0.063 Uiso 1 1 calc R . . C13 C 0.18598(10) 0.79884(12) 0.14607(9) 0.0437(4) Uani 1 1 d . . . H13A H 0.2313 0.8339 0.1761 0.052 Uiso 1 1 calc R . . C14 C 0.10308(12) 0.86563(14) 0.15332(10) 0.0576(5) Uani 1 1 d . . . H14A H 0.0882 0.8728 0.2050 0.069 Uiso 1 1 calc R . . H14B H 0.0556 0.8271 0.1290 0.069 Uiso 1 1 calc R . . C15 C 0.11272(15) 0.97919(15) 0.11982(11) 0.0731(6) Uani 1 1 d . . . H15A H 0.0573 1.0177 0.1227 0.088 Uiso 1 1 calc R . . H15B H 0.1554 1.0210 0.1477 0.088 Uiso 1 1 calc R . . C16 C 0.14123(16) 0.97219(17) 0.04076(11) 0.0789(7) Uani 1 1 d . . . H16A H 0.1494 1.0459 0.0213 0.095 Uiso 1 1 calc R . . H16B H 0.0960 0.9364 0.0120 0.095 Uiso 1 1 calc R . . C17 C 0.22527(14) 0.90839(16) 0.03371(11) 0.0719(6) Uani 1 1 d . . . H17A H 0.2718 0.9486 0.0580 0.086 Uiso 1 1 calc R . . H17B H 0.2404 0.9017 -0.0179 0.086 Uiso 1 1 calc R . . C18 C 0.21826(12) 0.79429(15) 0.06729(9) 0.0576(5) Uani 1 1 d . . . H18A H 0.1784 0.7501 0.0382 0.069 Uiso 1 1 calc R . . H18B H 0.2751 0.7590 0.0661 0.069 Uiso 1 1 calc R . . C19 C 0.11952(10) 0.52678(13) 0.17641(9) 0.0433(4) Uani 1 1 d . . . C20 C 0.19917(10) 0.63625(13) 0.23628(8) 0.0423(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0528(8) 0.0417(8) 0.0492(8) 0.0002(7) -0.0122(7) -0.0042(7) N2 0.0500(8) 0.0388(7) 0.0435(7) 0.0012(6) -0.0087(6) -0.0043(6) N3 0.0529(8) 0.0406(8) 0.0478(8) 0.0018(6) -0.0099(7) -0.0028(7) C1 0.0431(9) 0.0391(9) 0.0473(9) -0.0032(8) -0.0061(8) 0.0016(7) C2 0.0515(10) 0.0459(10) 0.0484(9) -0.0018(8) -0.0042(8) -0.0016(8) C3 0.0633(11) 0.0436(10) 0.0661(12) -0.0006(9) 0.0002(10) -0.0067(9) C4 0.0601(12) 0.0498(11) 0.0772(14) -0.0169(10) -0.0069(10) -0.0075(9) C5 0.0729(13) 0.0591(13) 0.0626(12) -0.0099(10) -0.0210(10) -0.0065(10) C6 0.0684(12) 0.0505(11) 0.0558(11) 0.0019(9) -0.0174(9) -0.0042(9) C7 0.0456(9) 0.0420(9) 0.0391(8) 0.0026(7) -0.0020(7) -0.0051(8) C8 0.0551(10) 0.0503(11) 0.0469(9) -0.0018(8) -0.0046(8) 0.0003(8) C9 0.0680(12) 0.0569(11) 0.0479(10) -0.0115(9) -0.0036(9) -0.0037(10) C10 0.0597(12) 0.0772(14) 0.0449(10) -0.0072(10) -0.0084(9) -0.0106(10) C11 0.0538(11) 0.0760(14) 0.0522(11) 0.0008(10) -0.0135(9) 0.0057(10) C12 0.0577(11) 0.0498(10) 0.0502(10) -0.0015(8) -0.0065(9) 0.0034(9) C13 0.0505(10) 0.0365(9) 0.0442(9) 0.0016(7) -0.0042(8) -0.0049(8) C14 0.0621(12) 0.0499(11) 0.0608(11) 0.0035(9) 0.0047(9) 0.0071(9) C15 0.0976(16) 0.0474(11) 0.0745(14) 0.0045(10) -0.0015(12) 0.0135(11) C16 0.1174(19) 0.0561(12) 0.0631(13) 0.0152(10) -0.0127(13) -0.0003(13) C17 0.0938(16) 0.0681(13) 0.0537(11) 0.0104(10) 0.0088(11) -0.0156(12) C18 0.0652(12) 0.0564(11) 0.0511(10) 0.0002(9) 0.0062(9) -0.0032(9) C19 0.0459(9) 0.0406(9) 0.0433(9) 0.0000(8) -0.0054(8) 0.0008(8) C20 0.0452(9) 0.0411(9) 0.0406(9) 0.0007(7) -0.0040(7) 0.0008(7) _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 C19 1.3235(19) . ? N1 N2 1.3637(17) . ? N2 C20 1.3457(18) . ? N2 C13 1.4718(18) . ? N3 C20 1.3277(19) . ? N3 C19 1.3605(19) . ? C1 C2 1.381(2) . ? C1 C6 1.386(2) . ? C1 C19 1.468(2) . ? C2 C3 1.381(2) . ? C2 H2A 0.9300 . ? C3 C4 1.374(3) . ? C3 H3A 0.9300 . ? C4 C5 1.373(3) . ? C4 H4A 0.9300 . ? C5 C6 1.376(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.381(2) . ? C7 C12 1.385(2) . ? C7 C20 1.475(2) . ? C8 C9 1.379(2) . ? C8 H8A 0.9300 . ? C9 C10 1.367(2) . ? C9 H9A 0.9300 . ? C10 C11 1.372(3) . ? C10 H10A 0.9300 . ? C11 C12 1.380(2) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.512(2) . ? C13 C18 1.515(2) . ? C13 H13A 0.9800 . ? C14 C15 1.515(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.504(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.507(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.518(2) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? 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 C19 N1 N2 102.88(12) . . ? C20 N2 N1 109.42(12) . . ? C20 N2 C13 131.96(13) . . ? N1 N2 C13 118.61(12) . . ? C20 N3 C19 103.17(13) . . ? C2 C1 C6 118.62(15) . . ? C2 C1 C19 120.93(14) . . ? C6 C1 C19 120.45(15) . . ? C1 C2 C3 120.44(16) . . ? C1 C2 H2A 119.8 . . ? C3 C2 H2A 119.8 . . ? C4 C3 C2 120.27(17) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C5 C4 C3 119.77(17) . . ? C5 C4 H4A 120.1 . . ? C3 C4 H4A 120.1 . . ? C4 C5 C6 120.11(18) . . ? C4 C5 H5A 119.9 . . ? C6 C5 H5A 119.9 . . ? C5 C6 C1 120.79(17) . . ? C5 C6 H6A 119.6 . . ? C1 C6 H6A 119.6 . . ? C8 C7 C12 118.66(15) . . ? C8 C7 C20 122.12(15) . . ? C12 C7 C20 119.18(14) . . ? C9 C8 C7 120.73(17) . . ? C9 C8 H8A 119.6 . . ? C7 C8 H8A 119.6 . . ? C10 C9 C8 120.04(17) . . ? C10 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 . . ? C9 C10 C11 120.07(17) . . ? C9 C10 H10A 120.0 . . ? C11 C10 H10A 120.0 . . ? C10 C11 C12 120.14(17) . . ? C10 C11 H11A 119.9 . . ? C12 C11 H11A 119.9 . . ? C11 C12 C7 120.33(16) . . ? C11 C12 H12A 119.8 . . ? C7 C12 H12A 119.8 . . ? N2 C13 C14 109.46(13) . . ? N2 C13 C18 110.68(13) . . ? C14 C13 C18 112.06(14) . . ? N2 C13 H13A 108.2 . . ? C14 C13 H13A 108.2 . . ? C18 C13 H13A 108.2 . . ? C13 C14 C15 111.82(15) . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14B 109.3 . . ? C15 C14 H14B 109.3 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 111.14(16) . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C17 110.97(17) . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C16 C17 C18 112.01(16) . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C13 C18 C17 111.68(15) . . ? C13 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? C13 C18 H18B 109.3 . . ? C17 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? N1 C19 N3 114.40(14) . . ? N1 C19 C1 122.03(14) . . ? N3 C19 C1 123.57(14) . . ? N3 C20 N2 110.11(13) . . ? N3 C20 C7 123.94(14) . . ? N2 C20 C7 125.95(14) . . ? 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 C19 N1 N2 C20 -0.69(17) . . . . ? C19 N1 N2 C13 -179.93(13) . . . . ? C6 C1 C2 C3 -1.2(2) . . . . ? C19 C1 C2 C3 178.66(15) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 0.9(3) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? C2 C1 C6 C5 1.3(3) . . . . ? C19 C1 C6 C5 -178.52(17) . . . . ? C12 C7 C8 C9 0.6(2) . . . . ? C20 C7 C8 C9 178.30(15) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C8 C9 C10 C11 -0.1(3) . . . . ? C9 C10 C11 C12 -0.7(3) . . . . ? C10 C11 C12 C7 1.4(3) . . . . ? C8 C7 C12 C11 -1.4(2) . . . . ? C20 C7 C12 C11 -179.15(15) . . . . ? C20 N2 C13 C14 -108.27(19) . . . . ? N1 N2 C13 C14 70.76(18) . . . . ? C20 N2 C13 C18 127.73(18) . . . . ? N1 N2 C13 C18 -53.23(19) . . . . ? N2 C13 C14 C15 -176.19(14) . . . . ? C18 C13 C14 C15 -53.0(2) . . . . ? C13 C14 C15 C16 55.4(2) . . . . ? C14 C15 C16 C17 -56.6(2) . . . . ? C15 C16 C17 C18 55.8(2) . . . . ? N2 C13 C18 C17 174.16(15) . . . . ? C14 C13 C18 C17 51.7(2) . . . . ? C16 C17 C18 C13 -53.2(2) . . . . ? N2 N1 C19 N3 -0.01(18) . . . . ? N2 N1 C19 C1 -179.71(14) . . . . ? C20 N3 C19 N1 0.69(19) . . . . ? C20 N3 C19 C1 -179.61(15) . . . . ? C2 C1 C19 N1 -170.66(16) . . . . ? C6 C1 C19 N1 9.2(2) . . . . ? C2 C1 C19 N3 9.7(2) . . . . ? C6 C1 C19 N3 -170.51(16) . . . . ? C19 N3 C20 N2 -1.11(17) . . . . ? C19 N3 C20 C7 179.32(15) . . . . ? N1 N2 C20 N3 1.18(18) . . . . ? C13 N2 C20 N3 -179.71(15) . . . . ? N1 N2 C20 C7 -179.26(14) . . . . ? C13 N2 C20 C7 -0.2(3) . . . . ? C8 C7 C20 N3 -131.90(18) . . . . ? C12 C7 C20 N3 45.8(2) . . . . ? C8 C7 C20 N2 48.6(2) . . . . ? C12 C7 C20 N2 -133.71(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.105 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.027 _database_code_depnum_ccdc_archive 'CCDC 940098' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cd213697 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H16 I N3' _chemical_formula_weight 437.27 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)/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 12.2051(11) _cell_length_b 18.0249(18) _cell_length_c 8.7754(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.387(2) _cell_angle_gamma 90.00 _cell_volume 1809.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2837 _cell_measurement_theta_min 4.520 _cell_measurement_theta_max 46.475 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.213 _exptl_crystal_size_mid 0.154 _exptl_crystal_size_min 0.117 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.777 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.50254 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _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 '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 10832 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3550 _reflns_number_gt 2687 _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^)+(0.0547P)^2^+0.6724P] 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 3550 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1069 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.003 _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 1.09581(2) 0.509381(17) 1.29435(4) 0.07720(16) Uani 1 1 d . . . N1 N 0.6992(2) 0.61822(14) 0.7961(3) 0.0421(6) Uani 1 1 d . . . N2 N 0.5439(2) 0.68719(14) 0.7486(3) 0.0434(6) Uani 1 1 d . . . N3 N 0.6079(2) 0.69982(15) 0.9071(3) 0.0468(6) Uani 1 1 d . . . C1 C 0.8799(3) 0.59724(19) 1.1114(4) 0.0463(7) Uani 1 1 d . . . H1 H 0.8772 0.5650 1.0275 0.056 Uiso 1 1 calc R . . C2 C 0.9676(3) 0.59067(19) 1.2600(4) 0.0473(8) Uani 1 1 d . . . C3 C 0.9730(3) 0.6377(2) 1.3868(4) 0.0574(9) Uani 1 1 d . . . H3 H 1.0319 0.6327 1.4876 0.069 Uiso 1 1 calc R . . C4 C 0.8895(3) 0.6922(2) 1.3608(4) 0.0626(10) Uani 1 1 d . . . H4 H 0.8927 0.7245 1.4448 0.075 Uiso 1 1 calc R . . C5 C 0.8018(3) 0.6997(2) 1.2130(4) 0.0545(9) Uani 1 1 d . . . H5 H 0.7462 0.7370 1.1976 0.065 Uiso 1 1 calc R . . C6 C 0.7954(3) 0.65180(17) 1.0862(4) 0.0425(7) Uani 1 1 d . . . C7 C 0.7004(3) 0.65708(16) 0.9301(4) 0.0417(7) Uani 1 1 d . . . C8 C 0.5988(3) 0.63795(16) 0.6841(4) 0.0391(7) Uani 1 1 d . . . C9 C 0.5568(3) 0.61044(16) 0.5167(4) 0.0397(7) Uani 1 1 d . . . C10 C 0.4422(3) 0.58972(18) 0.4355(4) 0.0458(7) Uani 1 1 d . . . H10 H 0.3870 0.5955 0.4857 0.055 Uiso 1 1 calc R . . C11 C 0.4091(3) 0.56082(19) 0.2819(4) 0.0525(8) Uani 1 1 d . . . H11 H 0.3317 0.5472 0.2282 0.063 Uiso 1 1 calc R . . C12 C 0.4894(4) 0.5520(2) 0.2073(4) 0.0587(9) Uani 1 1 d . . . H12 H 0.4665 0.5323 0.1028 0.070 Uiso 1 1 calc R . . C13 C 0.6038(3) 0.5719(2) 0.2860(4) 0.0612(10) Uani 1 1 d . . . H13 H 0.6585 0.5657 0.2351 0.073 Uiso 1 1 calc R . . C14 C 0.6375(3) 0.60103(19) 0.4401(4) 0.0507(8) Uani 1 1 d . . . H14 H 0.7150 0.6145 0.4932 0.061 Uiso 1 1 calc R . . C15 C 0.4365(3) 0.72902(18) 0.6740(4) 0.0486(8) Uani 1 1 d . . . H15A H 0.4126 0.7244 0.5568 0.058 Uiso 1 1 calc R . . H15B H 0.4519 0.7811 0.7013 0.058 Uiso 1 1 calc R . . C16 C 0.3377(3) 0.70353(18) 0.7273(4) 0.0451(7) Uani 1 1 d . . . C17 C 0.3308(3) 0.6331(2) 0.7807(4) 0.0606(9) Uani 1 1 d . . . H17 H 0.3893 0.5990 0.7867 0.073 Uiso 1 1 calc R . . C18 C 0.2375(4) 0.6123(3) 0.8259(5) 0.0770(12) Uani 1 1 d . . . H18 H 0.2335 0.5642 0.8621 0.092 Uiso 1 1 calc R . . C19 C 0.1507(4) 0.6622(3) 0.8175(5) 0.0823(14) Uani 1 1 d . . . H19 H 0.0879 0.6482 0.8479 0.099 Uiso 1 1 calc R . . C20 C 0.1574(3) 0.7321(3) 0.7643(6) 0.0811(14) Uani 1 1 d . . . H20 H 0.0991 0.7663 0.7589 0.097 Uiso 1 1 calc R . . C21 C 0.2496(3) 0.7531(2) 0.7184(4) 0.0611(10) Uani 1 1 d . . . H21 H 0.2526 0.8010 0.6809 0.073 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 0.0554(2) 0.0750(2) 0.0889(3) 0.00561(14) 0.00963(15) 0.01782(12) N1 0.0400(13) 0.0375(14) 0.0478(15) -0.0001(12) 0.0140(12) 0.0007(11) N2 0.0463(14) 0.0382(15) 0.0434(15) 0.0023(12) 0.0128(12) 0.0054(12) N3 0.0508(15) 0.0422(16) 0.0451(16) -0.0003(12) 0.0139(12) 0.0048(12) C1 0.0454(17) 0.0460(19) 0.0477(19) -0.0025(15) 0.0164(15) -0.0021(14) C2 0.0397(17) 0.048(2) 0.054(2) 0.0047(15) 0.0162(15) 0.0002(14) C3 0.0512(19) 0.072(3) 0.0446(19) -0.0022(18) 0.0108(16) -0.0059(18) C4 0.064(2) 0.071(3) 0.052(2) -0.0175(19) 0.0206(18) -0.001(2) C5 0.053(2) 0.055(2) 0.055(2) -0.0071(17) 0.0193(17) 0.0031(16) C6 0.0433(16) 0.0389(17) 0.0479(18) -0.0009(14) 0.0190(14) -0.0034(13) C7 0.0436(16) 0.0334(16) 0.0487(18) 0.0008(14) 0.0171(14) -0.0016(13) C8 0.0430(16) 0.0292(16) 0.0486(18) 0.0021(13) 0.0202(14) -0.0018(12) C9 0.0459(17) 0.0276(15) 0.0465(17) 0.0029(13) 0.0171(14) 0.0008(12) C10 0.0478(18) 0.0413(18) 0.0482(19) 0.0038(15) 0.0167(15) 0.0028(14) C11 0.053(2) 0.048(2) 0.050(2) -0.0005(16) 0.0092(16) 0.0021(15) C12 0.081(3) 0.049(2) 0.045(2) -0.0060(16) 0.0195(19) 0.0022(19) C13 0.075(3) 0.057(2) 0.065(2) -0.0014(18) 0.040(2) 0.0026(19) C14 0.0532(19) 0.046(2) 0.057(2) 0.0000(16) 0.0243(17) 0.0012(15) C15 0.0552(19) 0.0368(18) 0.0502(19) 0.0045(14) 0.0139(16) 0.0131(15) C16 0.0472(17) 0.047(2) 0.0354(16) -0.0065(14) 0.0076(13) 0.0079(14) C17 0.062(2) 0.059(2) 0.065(2) 0.0091(19) 0.0269(19) 0.0107(18) C18 0.075(3) 0.089(3) 0.068(3) 0.011(2) 0.025(2) -0.009(2) C19 0.057(2) 0.126(5) 0.067(3) -0.025(3) 0.025(2) -0.013(3) C20 0.049(2) 0.104(4) 0.086(3) -0.037(3) 0.019(2) 0.008(2) C21 0.052(2) 0.060(2) 0.060(2) -0.0182(18) 0.0057(17) 0.0111(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C2 2.087(3) . ? N1 C8 1.325(4) . ? N1 C7 1.364(4) . ? N2 C8 1.350(4) . ? N2 N3 1.356(4) . ? N2 C15 1.455(4) . ? N3 C7 1.323(4) . ? C1 C2 1.374(5) . ? C1 C6 1.386(4) . ? C1 H1 0.9300 . ? C2 C3 1.382(5) . ? C3 C4 1.376(5) . ? C3 H3 0.9300 . ? C4 C5 1.371(5) . ? C4 H4 0.9300 . ? C5 C6 1.389(4) . ? C5 H5 0.9300 . ? C6 C7 1.458(4) . ? C8 C9 1.463(4) . ? C9 C14 1.382(4) . ? C9 C10 1.382(5) . ? C10 C11 1.368(5) . ? C10 H10 0.9300 . ? C11 C12 1.365(5) . ? C11 H11 0.9300 . ? C12 C13 1.373(5) . ? C12 H12 0.9300 . ? C13 C14 1.373(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.509(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.365(5) . ? C16 C21 1.378(4) . ? C17 C18 1.383(5) . ? C17 H17 0.9300 . ? C18 C19 1.373(7) . ? C18 H18 0.9300 . ? C19 C20 1.357(7) . ? C19 H19 0.9300 . ? C20 C21 1.374(6) . ? C20 H20 0.9300 . ? C21 H21 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 C8 N1 C7 103.4(2) . . ? C8 N2 N3 110.3(2) . . ? C8 N2 C15 130.8(3) . . ? N3 N2 C15 118.8(2) . . ? C7 N3 N2 102.4(2) . . ? C2 C1 C6 120.2(3) . . ? C2 C1 H1 119.9 . . ? C6 C1 H1 119.9 . . ? C1 C2 C3 120.9(3) . . ? C1 C2 I1 119.6(2) . . ? C3 C2 I1 119.4(3) . . ? C4 C3 C2 118.7(3) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C5 C4 C3 121.1(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 120.3(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 118.9(3) . . ? C1 C6 C7 120.0(3) . . ? C5 C6 C7 121.1(3) . . ? N3 C7 N1 114.5(3) . . ? N3 C7 C6 122.6(3) . . ? N1 C7 C6 122.9(3) . . ? N1 C8 N2 109.3(3) . . ? N1 C8 C9 124.3(3) . . ? N2 C8 C9 126.3(3) . . ? C14 C9 C10 118.7(3) . . ? C14 C9 C8 118.1(3) . . ? C10 C9 C8 123.1(3) . . ? C11 C10 C9 120.6(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 120.2(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.2(3) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 119.9(3) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C9 120.4(3) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? N2 C15 C16 113.2(3) . . ? N2 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? N2 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C21 118.8(3) . . ? C17 C16 C15 122.7(3) . . ? C21 C16 C15 118.5(3) . . ? C16 C17 C18 120.4(4) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 120.3(5) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 119.3(4) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C19 C20 C21 120.7(4) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C20 C21 C16 120.5(4) . . ? C20 C21 H21 119.8 . . ? C16 C21 H21 119.8 . . ? 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 C8 N2 N3 C7 0.4(3) . . . . ? C15 N2 N3 C7 -176.1(3) . . . . ? C6 C1 C2 C3 0.4(5) . . . . ? C6 C1 C2 I1 -178.9(2) . . . . ? C1 C2 C3 C4 -0.9(5) . . . . ? I1 C2 C3 C4 178.3(3) . . . . ? C2 C3 C4 C5 0.6(6) . . . . ? C3 C4 C5 C6 0.2(6) . . . . ? C2 C1 C6 C5 0.5(5) . . . . ? C2 C1 C6 C7 -178.0(3) . . . . ? C4 C5 C6 C1 -0.7(5) . . . . ? C4 C5 C6 C7 177.7(3) . . . . ? N2 N3 C7 N1 0.1(3) . . . . ? N2 N3 C7 C6 -179.6(3) . . . . ? C8 N1 C7 N3 -0.6(3) . . . . ? C8 N1 C7 C6 179.1(3) . . . . ? C1 C6 C7 N3 169.0(3) . . . . ? C5 C6 C7 N3 -9.5(5) . . . . ? C1 C6 C7 N1 -10.7(4) . . . . ? C5 C6 C7 N1 170.8(3) . . . . ? C7 N1 C8 N2 0.8(3) . . . . ? C7 N1 C8 C9 -179.8(3) . . . . ? N3 N2 C8 N1 -0.8(3) . . . . ? C15 N2 C8 N1 175.1(3) . . . . ? N3 N2 C8 C9 179.9(3) . . . . ? C15 N2 C8 C9 -4.2(5) . . . . ? N1 C8 C9 C14 -38.8(4) . . . . ? N2 C8 C9 C14 140.4(3) . . . . ? N1 C8 C9 C10 137.6(3) . . . . ? N2 C8 C9 C10 -43.2(5) . . . . ? C14 C9 C10 C11 -0.3(5) . . . . ? C8 C9 C10 C11 -176.7(3) . . . . ? C9 C10 C11 C12 0.2(5) . . . . ? C10 C11 C12 C13 0.1(5) . . . . ? C11 C12 C13 C14 -0.2(6) . . . . ? C12 C13 C14 C9 0.0(6) . . . . ? C10 C9 C14 C13 0.2(5) . . . . ? C8 C9 C14 C13 176.7(3) . . . . ? C8 N2 C15 C16 110.1(4) . . . . ? N3 N2 C15 C16 -74.2(4) . . . . ? N2 C15 C16 C17 -25.8(4) . . . . ? N2 C15 C16 C21 155.6(3) . . . . ? C21 C16 C17 C18 -0.4(5) . . . . ? C15 C16 C17 C18 -179.0(3) . . . . ? C16 C17 C18 C19 0.0(6) . . . . ? C17 C18 C19 C20 0.1(7) . . . . ? C18 C19 C20 C21 0.3(7) . . . . ? C19 C20 C21 C16 -0.8(6) . . . . ? C17 C16 C21 C20 0.8(5) . . . . ? C15 C16 C21 C20 179.5(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.632 _refine_diff_density_min -0.770 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 978691'