# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Lee, Kwang-Ming' _publ_contact_author_email kmlee@nknu.edu.tw _publ_section_title ; N, N'-Dihexyl benzimidazolium Salts. Anion-controlled Bilayer Structures via - Dimer or C-H--- Catermer Motifs ; loop_ _publ_author_name 'Kwang-Ming Lee' 'Ivan Lin' # END data_3 _database_code_depnum_ccdc_archive 'CCDC 134804' #TrackingRef 'CE-ART-04-2010-000105-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1,3-dihexyl-benzimidazolium hexaflorophosphate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H31 F6 N2 P' _chemical_formula_weight 432.43 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' 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' _cell_length_a 8.5636(15) _cell_length_b 9.392(6) _cell_length_c 28.1899(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2267.3(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 19 _cell_measurement_theta_min 4.84 _cell_measurement_theta_max 8.27 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9173 _exptl_absorpt_correction_T_max 0.9657 _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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 48 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4.82 _diffrn_reflns_number 2166 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0870 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 22.49 _reflns_number_total 1985 _reflns_number_gt 1056 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.1031P)^2^+3.7254P] 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 0.0033(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.8(6) _refine_ls_number_reflns 1985 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1643 _refine_ls_R_factor_gt 0.0829 _refine_ls_wR_factor_ref 0.2470 _refine_ls_wR_factor_gt 0.1889 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _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 P1 P 0.4668(4) 0.1693(4) 0.18830(14) 0.0732(11) Uani 1 1 d . . . F1 F 0.3882(19) 0.0786(13) 0.1522(4) 0.237(8) Uani 1 1 d . . . F2 F 0.5546(13) 0.2594(11) 0.2251(3) 0.175(5) Uani 1 1 d . . . F3 F 0.6252(11) 0.1547(15) 0.1621(4) 0.193(5) Uani 1 1 d . . . F4 F 0.4980(15) 0.0369(10) 0.2184(5) 0.200(6) Uani 1 1 d . . . F5 F 0.3117(9) 0.1777(13) 0.2149(3) 0.156(4) Uani 1 1 d . . . F6 F 0.4415(13) 0.3009(9) 0.1578(4) 0.175(5) Uani 1 1 d . . . N1 N 0.7196(11) 0.6384(11) 0.1744(4) 0.064(3) Uani 1 1 d . . . N2 N 0.9115(13) 0.4875(10) 0.1822(4) 0.074(3) Uani 1 1 d . B . C1 C 0.7594(15) 0.5048(13) 0.1740(4) 0.065(3) Uani 1 1 d . . . H1A H 0.6901 0.4302 0.1687 0.078 Uiso 1 1 calc R . . C2 C 0.9714(14) 0.6242(11) 0.1881(4) 0.059(3) Uani 1 1 d . . . C3 C 1.1261(15) 0.6648(16) 0.1980(4) 0.081(4) Uani 1 1 d . . . H3A H 1.2068 0.5993 0.2014 0.097 Uiso 1 1 calc R . . C4 C 1.1490(16) 0.8119(17) 0.2024(5) 0.085(4) Uani 1 1 d . . . H4A H 1.2482 0.8451 0.2100 0.103 Uiso 1 1 calc R . . C5 C 1.0316(18) 0.9091(13) 0.1959(5) 0.084(4) Uani 1 1 d . . . H5A H 1.0525 1.0061 0.1980 0.101 Uiso 1 1 calc R . . C6 C 0.8815(15) 0.8623(12) 0.1861(5) 0.073(4) Uani 1 1 d . . . H6A H 0.8011 0.9275 0.1818 0.087 Uiso 1 1 calc R . . C7 C 0.8528(13) 0.7197(12) 0.1829(4) 0.055(3) Uani 1 1 d . . . C8 C 0.5647(12) 0.6941(16) 0.1633(5) 0.091(4) Uani 1 1 d . . . H8A H 0.5427 0.7735 0.1843 0.109 Uiso 1 1 calc R . . H8B H 0.4879 0.6206 0.1697 0.109 Uiso 1 1 calc R . . C9 C 0.5463(18) 0.7426(19) 0.1132(6) 0.130(6) Uani 1 1 d . . . H9A H 0.4398 0.7750 0.1089 0.156 Uiso 1 1 calc R . . H9B H 0.6143 0.8239 0.1082 0.156 Uiso 1 1 calc R . . C10 C 0.581(2) 0.6355(18) 0.0762(5) 0.121(6) Uani 1 1 d . . . H10A H 0.6894 0.6070 0.0791 0.146 Uiso 1 1 calc R . . H10B H 0.5170 0.5520 0.0818 0.146 Uiso 1 1 calc R . . C11 C 0.553(2) 0.686(2) 0.0273(7) 0.151(7) Uani 1 1 d . . . H11A H 0.4434 0.7111 0.0247 0.181 Uiso 1 1 calc R . . H11B H 0.6122 0.7735 0.0230 0.181 Uiso 1 1 calc R . . C12 C 0.590(3) 0.594(2) -0.0106(6) 0.160(8) Uani 1 1 d . . . H12A H 0.5335 0.5060 -0.0057 0.192 Uiso 1 1 calc R . . H12B H 0.7003 0.5726 -0.0087 0.192 Uiso 1 1 calc R . . C13 C 0.556(3) 0.644(2) -0.0595(7) 0.206(10) Uani 1 1 d . . . H13A H 0.5772 0.5686 -0.0816 0.309 Uiso 1 1 calc R . . H13B H 0.6214 0.7244 -0.0668 0.309 Uiso 1 1 calc R . . H13C H 0.4485 0.6715 -0.0619 0.309 Uiso 1 1 calc R . . C14 C 0.9977(17) 0.3519(13) 0.1794(5) 0.101(5) Uani 1 1 d . . . H14A H 0.9283 0.2733 0.1867 0.122 Uiso 1 1 calc R A 1 H14B H 1.0821 0.3517 0.2024 0.122 Uiso 1 1 calc R A 1 C15 C 1.063(7) 0.334(6) 0.1298(16) 0.146(16) Uiso 0.55(5) 1 d P B 1 H15A H 1.1501 0.2699 0.1350 0.176 Uiso 0.55(5) 1 calc PR B 1 H15B H 0.9839 0.2770 0.1144 0.176 Uiso 0.55(5) 1 calc PR B 1 C16 C 1.109(4) 0.407(3) 0.0982(11) 0.103(12) Uiso 0.55(5) 1 d P B 1 H16A H 1.2099 0.4428 0.1085 0.123 Uiso 0.55(5) 1 calc PR B 1 H16B H 1.0399 0.4880 0.0970 0.123 Uiso 0.55(5) 1 calc PR B 1 C17 C 1.131(6) 0.363(6) 0.0488(18) 0.161(18) Uiso 0.55(5) 1 d P B 1 H17A H 1.1582 0.2623 0.0499 0.193 Uiso 0.55(5) 1 calc PR B 1 H17B H 1.2244 0.4118 0.0378 0.193 Uiso 0.55(5) 1 calc PR B 1 C18 C 1.018(5) 0.377(4) 0.0109(15) 0.143(17) Uiso 0.55(5) 1 d P B 1 H18A H 0.9705 0.4703 0.0146 0.171 Uiso 0.55(5) 1 calc PR B 1 H18B H 0.9360 0.3080 0.0173 0.171 Uiso 0.55(5) 1 calc PR B 1 C19 C 1.054(6) 0.363(5) -0.0364(16) 0.159(17) Uiso 0.55(5) 1 d P B 1 H19A H 0.9602 0.3543 -0.0546 0.238 Uiso 0.55(5) 1 calc PR B 1 H19B H 1.1180 0.2804 -0.0409 0.238 Uiso 0.55(5) 1 calc PR B 1 H19C H 1.1107 0.4463 -0.0467 0.238 Uiso 0.55(5) 1 calc PR B 1 C15A C 0.996(4) 0.288(3) 0.1319(9) 0.057(9) Uiso 0.45(5) 1 d P B 2 H15C H 1.0756 0.2143 0.1327 0.068 Uiso 0.45(5) 1 calc PR B 2 H15D H 0.8970 0.2389 0.1295 0.068 Uiso 0.45(5) 1 calc PR B 2 C16A C 1.014(7) 0.350(5) 0.0921(17) 0.137(19) Uiso 0.45(5) 1 d P B 2 H16C H 1.0958 0.4189 0.0990 0.165 Uiso 0.45(5) 1 calc PR B 2 H16D H 0.9195 0.4062 0.0894 0.165 Uiso 0.45(5) 1 calc PR B 2 C17A C 1.046(6) 0.314(5) 0.0436(16) 0.111(16) Uiso 0.45(5) 1 d P B 2 H17C H 0.9469 0.3028 0.0272 0.133 Uiso 0.45(5) 1 calc PR B 2 H17D H 1.0976 0.2219 0.0431 0.133 Uiso 0.45(5) 1 calc PR B 2 C18A C 1.143(9) 0.416(6) 0.016(2) 0.18(2) Uiso 0.45(5) 1 d P B 2 H18C H 1.2489 0.4211 0.0284 0.210 Uiso 0.45(5) 1 calc PR B 2 H18D H 1.0974 0.5106 0.0160 0.210 Uiso 0.45(5) 1 calc PR B 2 C19A C 1.136(8) 0.337(7) -0.039(2) 0.18(3) Uiso 0.45(5) 1 d P B 2 H19D H 1.1736 0.4030 -0.0620 0.277 Uiso 0.45(5) 1 calc PR B 2 H19E H 1.0302 0.3115 -0.0457 0.277 Uiso 0.45(5) 1 calc PR B 2 H19F H 1.2003 0.2537 -0.0385 0.277 Uiso 0.45(5) 1 calc PR B 2 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 P1 0.072(2) 0.0622(18) 0.085(2) -0.005(2) 0.000(2) -0.010(2) F1 0.34(2) 0.233(13) 0.132(9) -0.063(9) 0.052(11) -0.194(14) F2 0.219(11) 0.192(9) 0.115(7) -0.025(7) -0.028(7) -0.111(10) F3 0.116(7) 0.253(12) 0.211(12) 0.020(12) 0.067(8) 0.036(10) F4 0.177(11) 0.120(7) 0.303(17) 0.100(9) -0.002(12) 0.013(8) F5 0.088(6) 0.219(12) 0.162(8) 0.001(9) 0.045(5) 0.008(7) F6 0.171(9) 0.112(7) 0.241(12) 0.089(8) -0.043(9) -0.010(7) N1 0.049(6) 0.066(6) 0.077(7) -0.003(6) 0.007(5) -0.001(5) N2 0.075(8) 0.064(6) 0.085(8) 0.006(6) 0.014(7) 0.010(6) C1 0.059(8) 0.064(8) 0.072(9) -0.008(8) 0.018(7) -0.016(7) C2 0.064(8) 0.062(7) 0.051(6) 0.005(7) 0.012(8) -0.015(7) C3 0.073(9) 0.092(9) 0.078(9) -0.005(10) 0.004(8) 0.000(9) C4 0.066(9) 0.111(12) 0.079(10) 0.000(10) -0.003(7) -0.020(10) C5 0.082(9) 0.067(7) 0.103(11) 0.003(8) -0.004(10) -0.022(9) C6 0.072(9) 0.063(8) 0.083(10) 0.016(8) 0.001(9) 0.017(7) C7 0.039(6) 0.067(7) 0.061(8) 0.006(7) 0.008(7) 0.008(6) C8 0.045(7) 0.126(11) 0.102(11) -0.004(10) 0.003(7) 0.017(8) C9 0.114(13) 0.171(15) 0.105(13) -0.004(12) -0.028(11) 0.061(13) C10 0.136(14) 0.158(15) 0.071(10) -0.026(12) -0.015(10) -0.010(14) C11 0.151(16) 0.182(18) 0.120(15) 0.001(16) -0.026(14) 0.062(16) C12 0.18(2) 0.21(2) 0.096(14) 0.009(16) -0.014(14) -0.017(18) C13 0.25(3) 0.27(2) 0.102(13) -0.008(19) -0.016(16) 0.02(3) C14 0.113(12) 0.074(8) 0.117(12) -0.003(9) -0.005(10) 0.024(9) _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 P1 F1 1.488(11) . ? P1 F6 1.522(9) . ? P1 F5 1.527(8) . ? P1 F4 1.528(9) . ? P1 F2 1.537(9) . ? P1 F3 1.550(9) . ? N1 C1 1.301(13) . ? N1 C7 1.393(13) . ? N1 C8 1.460(13) . ? N2 C1 1.333(14) . ? N2 C2 1.392(13) . ? N2 C14 1.474(14) . ? C2 C7 1.363(13) . ? C2 C3 1.407(16) . ? C3 C4 1.401(17) . ? C4 C5 1.370(17) . ? C5 C6 1.386(16) . ? C6 C7 1.365(15) . ? C8 C9 1.493(18) . ? C9 C10 1.478(18) . ? C10 C11 1.48(2) . ? C11 C12 1.41(2) . ? C12 C13 1.48(2) . ? C14 C15A 1.47(3) . ? C14 C15 1.52(4) . ? C15 C16 1.19(5) . ? C16 C17 1.47(5) . ? C17 C18 1.45(8) . ? C18 C19 1.38(5) . ? C15A C16A 1.27(5) . ? C16A C17A 1.44(6) . ? C17A C18A 1.49(9) . ? C18A C19A 1.71(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 F1 P1 F6 90.8(7) . . ? F1 P1 F5 88.4(7) . . ? F6 P1 F5 96.4(6) . . ? F1 P1 F4 89.6(7) . . ? F6 P1 F4 178.0(8) . . ? F5 P1 F4 85.5(7) . . ? F1 P1 F2 177.5(9) . . ? F6 P1 F2 90.2(6) . . ? F5 P1 F2 93.7(7) . . ? F4 P1 F2 89.3(7) . . ? F1 P1 F3 91.1(8) . . ? F6 P1 F3 85.8(7) . . ? F5 P1 F3 177.7(8) . . ? F4 P1 F3 92.2(7) . . ? F2 P1 F3 86.7(6) . . ? C1 N1 C7 108.4(10) . . ? C1 N1 C8 125.6(11) . . ? C7 N1 C8 125.8(10) . . ? C1 N2 C2 105.6(10) . . ? C1 N2 C14 125.9(11) . . ? C2 N2 C14 128.2(10) . . ? N1 C1 N2 111.9(11) . . ? C7 C2 N2 108.6(10) . . ? C7 C2 C3 123.0(11) . . ? N2 C2 C3 128.4(12) . . ? C4 C3 C2 114.6(13) . . ? C3 C4 C5 122.9(13) . . ? C6 C5 C4 119.7(11) . . ? C7 C6 C5 119.4(11) . . ? C2 C7 C6 120.3(11) . . ? C2 C7 N1 105.6(9) . . ? C6 C7 N1 134.2(11) . . ? N1 C8 C9 114.0(10) . . ? C10 C9 C8 116.0(13) . . ? C11 C10 C9 113.9(16) . . ? C12 C11 C10 118.2(17) . . ? C11 C12 C13 118(2) . . ? N2 C14 C15A 113.4(14) . . ? N2 C14 C15 109.1(19) . . ? C15A C14 C15 28(2) . . ? C16 C15 C14 139(4) . . ? C15 C16 C17 127(4) . . ? C16 C17 C18 126(4) . . ? C17 C18 C19 123(4) . . ? C16A C15A C14 128(3) . . ? C15A C16A C17A 139(4) . . ? C16A C17A C18A 116(4) . . ? C17A C18A C19A 100(4) . . ? _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 0.934 _refine_diff_density_max 0.382 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.061 # Attachment 'CE-ART-04-2010-000105-1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 138176' #TrackingRef 'CE-ART-04-2010-000105-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H33 Br N2 O' _chemical_formula_weight 385.38 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.096(10) _cell_length_b 9.1414(14) _cell_length_c 13.805(3) _cell_angle_alpha 71.505(15) _cell_angle_beta 78.19(5) _cell_angle_gamma 76.70(3) _cell_volume 1048.6(11) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 21 _cell_measurement_theta_min 5.03 _cell_measurement_theta_max 12.73 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 1.967 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6067 _exptl_absorpt_correction_T_max 0.9971 _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 192 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 17.23 _diffrn_reflns_number 2838 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 22.48 _reflns_number_total 2632 _reflns_number_gt 1894 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0797P)^2^+1.0407P] 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 2632 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1516 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.044 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.16932(8) 0.62313(8) 0.07499(6) 0.0834(3) Uani 1 1 d . . . O1 O -0.0432(8) 0.3427(8) 0.1357(5) 0.148(2) Uani 1 1 d . . . H1O H 0.0311 0.3895 0.1275 0.222 Uiso 1 1 d R . . H2O H -0.1059 0.4271 0.1159 0.222 Uiso 1 1 d R . . N1 N 0.6161(5) -0.2636(5) 0.1330(3) 0.0528(11) Uani 1 1 d . . . N2 N 0.7521(5) -0.0990(5) 0.1378(3) 0.0551(11) Uani 1 1 d . . . C1 C 0.7537(7) -0.2436(7) 0.1362(4) 0.0589(15) Uani 1 1 d . . . H1A H 0.8407 -0.3208 0.1373 0.071 Uiso 1 1 calc R . . C2 C 0.6025(6) -0.0192(6) 0.1365(4) 0.0508(13) Uani 1 1 d . . . C3 C 0.5376(7) 0.1338(6) 0.1346(4) 0.0616(15) Uani 1 1 d . . . H3A H 0.5955 0.2049 0.1355 0.074 Uiso 1 1 calc R . . C4 C 0.3845(8) 0.1753(7) 0.1313(5) 0.0687(17) Uani 1 1 d . . . H4A H 0.3366 0.2769 0.1310 0.082 Uiso 1 1 calc R . . C5 C 0.2972(7) 0.0692(7) 0.1283(5) 0.0665(16) Uani 1 1 d . . . H5A H 0.1930 0.1025 0.1261 0.080 Uiso 1 1 calc R . . C6 C 0.3602(7) -0.0803(7) 0.1285(4) 0.0590(15) Uani 1 1 d . . . H6A H 0.3021 -0.1500 0.1258 0.071 Uiso 1 1 calc R . . C7 C 0.5160(6) -0.1243(6) 0.1329(4) 0.0493(13) Uani 1 1 d . . . C8 C 0.5728(7) -0.4102(6) 0.1332(5) 0.0672(16) Uani 1 1 d . . . H8A H 0.6623 -0.4768 0.1085 0.081 Uiso 1 1 calc R . . H8B H 0.4989 -0.3851 0.0860 0.081 Uiso 1 1 calc R . . C9 C 0.5054(8) -0.4986(7) 0.2391(5) 0.0777(19) Uani 1 1 d . . . H9A H 0.4224 -0.4281 0.2663 0.093 Uiso 1 1 calc R . . H9B H 0.4629 -0.5826 0.2327 0.093 Uiso 1 1 calc R . . C10 C 0.6180(8) -0.5671(8) 0.3144(5) 0.089(2) Uani 1 1 d . . . H10A H 0.6505 -0.4826 0.3282 0.107 Uiso 1 1 calc R . . H10B H 0.7072 -0.6272 0.2838 0.107 Uiso 1 1 calc R . . C11 C 0.5513(10) -0.6736(9) 0.4167(6) 0.105(2) Uani 1 1 d . . . H11A H 0.4613 -0.6131 0.4462 0.125 Uiso 1 1 calc R . . H11B H 0.5191 -0.7576 0.4023 0.125 Uiso 1 1 calc R . . C12 C 0.6559(11) -0.7429(11) 0.4936(7) 0.125(3) Uani 1 1 d . . . H12A H 0.6868 -0.6596 0.5098 0.150 Uiso 1 1 calc R . . H12B H 0.7467 -0.8031 0.4646 0.150 Uiso 1 1 calc R . . C13 C 0.5844(13) -0.8489(12) 0.5923(7) 0.148(4) Uani 1 1 d . . . H13A H 0.6563 -0.8900 0.6408 0.222 Uiso 1 1 calc R . . H13B H 0.5571 -0.9338 0.5771 0.222 Uiso 1 1 calc R . . H13C H 0.4946 -0.7897 0.6215 0.222 Uiso 1 1 calc R . . C14 C 0.8831(7) -0.0366(7) 0.1471(5) 0.0690(16) Uani 1 1 d . . . H14A H 0.8834 0.0671 0.0989 0.083 Uiso 1 1 calc R . . H14B H 0.9773 -0.1038 0.1292 0.083 Uiso 1 1 calc R . . C15 C 0.8762(8) -0.0269(8) 0.2561(5) 0.083(2) Uani 1 1 d . . . H15A H 0.9530 0.0316 0.2556 0.099 Uiso 1 1 calc R . . H15B H 0.7773 0.0320 0.2757 0.099 Uiso 1 1 calc R . . C16 C 0.9000(10) -0.1804(9) 0.3363(6) 0.099(2) Uani 1 1 d . . . H16A H 0.9998 -0.2389 0.3184 0.119 Uiso 1 1 calc R . . H16B H 0.8242 -0.2401 0.3370 0.119 Uiso 1 1 calc R . . C17 C 0.8885(11) -0.1624(11) 0.4454(6) 0.116(3) Uani 1 1 d . . . H17A H 0.9666 -0.1050 0.4441 0.139 Uiso 1 1 calc R . . H17B H 0.7904 -0.0990 0.4608 0.139 Uiso 1 1 calc R . . C18 C 0.9044(12) -0.3042(13) 0.5274(8) 0.138(3) Uani 1 1 d . . . H18A H 1.0036 -0.3666 0.5130 0.165 Uiso 1 1 calc R . . H18B H 0.8277 -0.3628 0.5280 0.165 Uiso 1 1 calc R . . C19 C 0.8896(14) -0.2841(14) 0.6322(7) 0.156(4) Uani 1 1 d . . . H19A H 0.9003 -0.3851 0.6823 0.234 Uiso 1 1 calc R . . H19B H 0.7911 -0.2240 0.6481 0.234 Uiso 1 1 calc R . . H19C H 0.9677 -0.2303 0.6337 0.234 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0798(5) 0.0686(5) 0.1128(6) -0.0351(4) -0.0191(4) -0.0166(3) O1 0.143(5) 0.136(5) 0.156(6) -0.003(4) -0.037(5) -0.050(4) N1 0.067(3) 0.044(3) 0.048(3) -0.013(2) -0.010(2) -0.008(2) N2 0.062(3) 0.055(3) 0.047(3) -0.011(2) -0.007(2) -0.013(2) C1 0.063(4) 0.058(4) 0.050(4) -0.015(3) -0.009(3) -0.001(3) C2 0.063(4) 0.049(3) 0.039(3) -0.011(2) -0.003(3) -0.014(3) C3 0.082(5) 0.046(3) 0.055(4) -0.013(3) -0.001(3) -0.018(3) C4 0.085(5) 0.050(3) 0.061(4) -0.015(3) -0.003(3) 0.000(3) C5 0.064(4) 0.066(4) 0.065(4) -0.019(3) -0.006(3) -0.009(3) C6 0.069(4) 0.059(4) 0.051(4) -0.015(3) -0.010(3) -0.016(3) C7 0.060(4) 0.046(3) 0.041(3) -0.010(2) -0.008(3) -0.009(3) C8 0.094(5) 0.048(3) 0.066(4) -0.019(3) -0.019(3) -0.013(3) C9 0.103(5) 0.053(4) 0.083(5) -0.015(3) -0.016(4) -0.028(3) C10 0.101(5) 0.077(5) 0.081(5) 0.000(4) -0.017(4) -0.024(4) C11 0.126(7) 0.097(6) 0.082(6) -0.007(5) -0.017(5) -0.027(5) C12 0.149(8) 0.117(7) 0.087(6) -0.009(5) -0.023(6) -0.006(6) C13 0.191(10) 0.139(8) 0.072(6) 0.006(6) -0.004(6) -0.009(7) C14 0.064(4) 0.073(4) 0.071(4) -0.012(3) -0.012(3) -0.024(3) C15 0.094(5) 0.088(5) 0.078(5) -0.022(4) -0.024(4) -0.031(4) C16 0.115(6) 0.104(6) 0.082(6) -0.019(5) -0.024(5) -0.027(5) C17 0.154(8) 0.110(7) 0.088(6) -0.014(5) -0.044(6) -0.027(6) C18 0.141(8) 0.151(9) 0.126(9) -0.035(7) -0.018(7) -0.040(7) C19 0.219(12) 0.185(10) 0.068(6) -0.030(6) -0.032(7) -0.041(9) _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 C1 1.318(7) . ? N1 C7 1.385(6) . ? N1 C8 1.480(7) . ? N2 C1 1.325(7) . ? N2 C2 1.389(7) . ? N2 C14 1.478(7) . ? C2 C3 1.381(7) . ? C2 C7 1.393(7) . ? C3 C4 1.363(8) . ? C4 C5 1.403(8) . ? C5 C6 1.354(8) . ? C6 C7 1.390(8) . ? C8 C9 1.509(8) . ? C9 C10 1.500(9) . ? C10 C11 1.536(9) . ? C11 C12 1.463(11) . ? C12 C13 1.519(11) . ? C14 C15 1.523(9) . ? C15 C16 1.488(9) . ? C16 C17 1.547(10) . ? C17 C18 1.425(12) . ? C18 C19 1.491(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C7 108.2(4) . . ? C1 N1 C8 126.6(5) . . ? C7 N1 C8 125.2(5) . . ? C1 N2 C2 107.7(4) . . ? C1 N2 C14 126.4(5) . . ? C2 N2 C14 125.8(5) . . ? N1 C1 N2 111.1(5) . . ? C3 C2 N2 131.9(5) . . ? C3 C2 C7 121.5(5) . . ? N2 C2 C7 106.5(4) . . ? C4 C3 C2 116.6(5) . . ? C3 C4 C5 121.9(5) . . ? C6 C5 C4 121.9(6) . . ? C5 C6 C7 116.7(5) . . ? N1 C7 C6 132.1(5) . . ? N1 C7 C2 106.5(5) . . ? C6 C7 C2 121.4(5) . . ? N1 C8 C9 112.4(5) . . ? C10 C9 C8 113.9(6) . . ? C9 C10 C11 112.5(6) . . ? C12 C11 C10 114.9(7) . . ? C11 C12 C13 112.4(8) . . ? N2 C14 C15 111.6(5) . . ? C16 C15 C14 115.2(6) . . ? C15 C16 C17 112.6(7) . . ? C18 C17 C16 116.2(8) . . ? C17 C18 C19 115.3(9) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 22.48 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.629 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.063 # END data_2 _database_code_depnum_ccdc_archive 'CCDC 780175' #TrackingRef 'CE-ART-04-2010-000105-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H64 I2 N4 O' _chemical_formula_weight 846.73 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' 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 9.288(7) _cell_length_b 13.7946(13) _cell_length_c 18.739(3) _cell_angle_alpha 69.402(14) _cell_angle_beta 76.16(3) _cell_angle_gamma 86.15(3) _cell_volume 2181.6(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21 _cell_measurement_theta_min 4.84 _cell_measurement_theta_max 12.62 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 1.471 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5907 _exptl_absorpt_correction_T_max 0.6666 _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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 198 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 99.94 _diffrn_reflns_number 8091 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7556 _reflns_number_gt 5021 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0900P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7556 _refine_ls_number_parameters 407 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1457 _refine_ls_wR_factor_gt 0.1363 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 O1 O 0.8006(6) -0.1292(4) 0.2399(4) 0.146(2) Uani 1 1 d . . . H2O H 0.8555 -0.1739 0.2254 0.219 Uiso 1 1 d R . . H1O H 0.7430 -0.1817 0.2556 0.219 Uiso 1 1 d R . . I1 I 0.51453(4) 0.67713(3) 0.33193(2) 0.08188(16) Uani 1 1 d . . . N3 N 0.2404(4) 0.3634(3) 0.4882(2) 0.0615(9) Uani 1 1 d . . . N4 N 0.0275(5) 0.3052(3) 0.5693(2) 0.0579(9) Uani 1 1 d . . . C1A C 0.1738(6) 0.3048(3) 0.5597(3) 0.0620(12) Uani 1 1 d . . . H1AA H 0.2232 0.2679 0.5985 0.074 Uiso 1 1 calc R . . C2A C -0.0055(5) 0.3696(3) 0.4993(2) 0.0511(10) Uani 1 1 d . . . C3A C -0.1413(6) 0.4000(3) 0.4781(3) 0.0658(12) Uani 1 1 d . . . H3AA H -0.2315 0.3755 0.5130 0.079 Uiso 1 1 calc R . . C4A C -0.1340(7) 0.4679(4) 0.4029(3) 0.0763(15) Uani 1 1 d . . . H4AA H -0.2211 0.4896 0.3862 0.092 Uiso 1 1 calc R . . C5A C 0.0032(7) 0.5046(4) 0.3513(3) 0.0803(16) Uani 1 1 d . . . H5AA H 0.0042 0.5505 0.3011 0.096 Uiso 1 1 calc R . . C6A C 0.1371(6) 0.4755(3) 0.3720(3) 0.0681(13) Uani 1 1 d . . . H6AA H 0.2271 0.5007 0.3371 0.082 Uiso 1 1 calc R . . C7A C 0.1304(6) 0.4069(3) 0.4472(3) 0.0588(11) Uani 1 1 d . . . C8A C -0.0823(7) 0.2460(4) 0.6401(3) 0.0751(15) Uani 1 1 d . . . H8AA H -0.1671 0.2891 0.6484 0.090 Uiso 1 1 calc R . . H8AB H -0.0388 0.2277 0.6852 0.090 Uiso 1 1 calc R . . C9A C -0.1333(7) 0.1496(4) 0.6336(3) 0.0810(16) Uani 1 1 d . . . H9AA H -0.1728 0.1683 0.5871 0.097 Uiso 1 1 calc R . . H9AB H -0.2132 0.1175 0.6786 0.097 Uiso 1 1 calc R . . C10A C -0.0126(7) 0.0719(4) 0.6290(4) 0.0939(18) Uani 1 1 d . . . H10A H 0.0301 0.0557 0.6742 0.113 Uiso 1 1 calc R . . H10B H 0.0651 0.1030 0.5825 0.113 Uiso 1 1 calc R . . C11A C -0.0660(8) -0.0283(5) 0.6261(4) 0.105(2) Uani 1 1 d . . . H11A H -0.1433 -0.0591 0.6728 0.126 Uiso 1 1 calc R . . H11B H -0.1102 -0.0115 0.5814 0.126 Uiso 1 1 calc R . . C12A C 0.0478(10) -0.1054(5) 0.6208(5) 0.124(3) Uani 1 1 d . . . H12C H 0.0926 -0.1222 0.6653 0.149 Uiso 1 1 calc R . . H12D H 0.1247 -0.0752 0.5738 0.149 Uiso 1 1 calc R . . C13A C -0.0089(12) -0.2042(6) 0.6188(6) 0.166(4) Uani 1 1 d . . . H13D H 0.0717 -0.2508 0.6151 0.249 Uiso 1 1 calc R . . H13E H -0.0515 -0.1887 0.5742 0.249 Uiso 1 1 calc R . . H13F H -0.0831 -0.2359 0.6659 0.249 Uiso 1 1 calc R . . C14A C 0.4013(6) 0.3818(4) 0.4579(3) 0.0766(14) Uani 1 1 d . . . H14A H 0.4498 0.3571 0.5014 0.092 Uiso 1 1 calc R . . H14B H 0.4212 0.4557 0.4327 0.092 Uiso 1 1 calc R . . C15A C 0.4657(8) 0.3279(5) 0.3998(4) 0.104(2) Uani 1 1 d . . . H15C H 0.4160 0.3535 0.3568 0.125 Uiso 1 1 calc R . . H15D H 0.5695 0.3482 0.3784 0.125 Uiso 1 1 calc R . . C16A C 0.4559(9) 0.2169(6) 0.4287(5) 0.119(2) Uani 1 1 d . . . H16C H 0.3531 0.1961 0.4537 0.143 Uiso 1 1 calc R . . H16D H 0.5125 0.1907 0.4686 0.143 Uiso 1 1 calc R . . C17A C 0.5118(10) 0.1638(7) 0.3664(5) 0.138(3) Uani 1 1 d . . . H17C H 0.4593 0.1941 0.3250 0.166 Uiso 1 1 calc R . . H17D H 0.6158 0.1826 0.3435 0.166 Uiso 1 1 calc R . . C18A C 0.4992(13) 0.0564(8) 0.3889(6) 0.165(4) Uani 1 1 d . . . H18C H 0.3958 0.0369 0.4130 0.198 Uiso 1 1 calc R . . H18D H 0.5545 0.0256 0.4291 0.198 Uiso 1 1 calc R . . C19A C 0.5485(12) 0.0103(8) 0.3291(7) 0.188(5) Uani 1 1 d . . . H19A H 0.5373 -0.0636 0.3526 0.283 Uiso 1 1 calc R . . H19B H 0.6509 0.0284 0.3045 0.283 Uiso 1 1 calc R . . H19C H 0.4900 0.0356 0.2907 0.283 Uiso 1 1 calc R . . I2 I 0.06931(4) 0.74853(3) 0.13744(2) 0.08581(17) Uani 1 1 d . . . N1 N -0.1937(4) 0.8946(3) -0.0354(2) 0.0619(10) Uani 1 1 d . . . N2 N -0.3908(4) 0.8045(3) 0.0421(2) 0.0604(9) Uani 1 1 d . . . C1B C -0.2459(6) 0.8169(4) 0.0311(3) 0.0661(12) Uani 1 1 d . . . H1BA H -0.1887 0.7770 0.0650 0.079 Uiso 1 1 calc R . . C2B C -0.4370(5) 0.8777(3) -0.0200(2) 0.0553(10) Uani 1 1 d . . . C3B C -0.5794(5) 0.8991(4) -0.0366(3) 0.0652(12) Uani 1 1 d . . . H3BA H -0.6631 0.8603 -0.0037 0.078 Uiso 1 1 calc R . . C4B C -0.5870(6) 0.9809(4) -0.1045(3) 0.0704(13) Uani 1 1 d . . . H4BA H -0.6782 0.9980 -0.1177 0.085 Uiso 1 1 calc R . . C5B C -0.4600(7) 1.0383(4) -0.1536(3) 0.0737(14) Uani 1 1 d . . . H5BA H -0.4694 1.0922 -0.1990 0.088 Uiso 1 1 calc R . . C6B C -0.3234(6) 1.0183(4) -0.1376(3) 0.0686(13) Uani 1 1 d . . . H6BA H -0.2404 1.0580 -0.1703 0.082 Uiso 1 1 calc R . . C7B C -0.3137(5) 0.9349(3) -0.0694(2) 0.0569(11) Uani 1 1 d . . . C8B C -0.4833(6) 0.7213(4) 0.1075(3) 0.0685(13) Uani 1 1 d . . . H8BA H -0.5797 0.7485 0.1239 0.082 Uiso 1 1 calc R . . H8BB H -0.4368 0.6985 0.1516 0.082 Uiso 1 1 calc R . . C9B C -0.5032(7) 0.6307(4) 0.0839(3) 0.0809(16) Uani 1 1 d . . . H9BA H -0.4064 0.6069 0.0640 0.097 Uiso 1 1 calc R . . H9BB H -0.5554 0.6529 0.0419 0.097 Uiso 1 1 calc R . . C10B C -0.5882(8) 0.5424(4) 0.1508(4) 0.0939(18) Uani 1 1 d . . . H10C H -0.6876 0.5643 0.1686 0.113 Uiso 1 1 calc R . . H10D H -0.5396 0.5224 0.1942 0.113 Uiso 1 1 calc R . . C11B C -0.5967(11) 0.4470(6) 0.1242(5) 0.132(3) Uani 1 1 d . . . H11C H -0.6481 0.4680 0.0819 0.158 Uiso 1 1 calc R . . H11D H -0.4965 0.4294 0.1032 0.158 Uiso 1 1 calc R . . C12B C -0.6672(12) 0.3580(6) 0.1822(5) 0.147(3) Uani 1 1 d . . . H12A H -0.7701 0.3736 0.2002 0.176 Uiso 1 1 calc R . . H12B H -0.6211 0.3397 0.2264 0.176 Uiso 1 1 calc R . . C13B C -0.6626(11) 0.2665(5) 0.1564(5) 0.144(3) Uani 1 1 d . . . H13A H -0.7134 0.2086 0.1991 0.216 Uiso 1 1 calc R . . H13B H -0.5612 0.2490 0.1400 0.216 Uiso 1 1 calc R . . H13C H -0.7101 0.2832 0.1134 0.216 Uiso 1 1 calc R . . C14B C -0.0362(5) 0.9252(4) -0.0697(3) 0.0733(14) Uani 1 1 d . . . H14C H 0.0180 0.9041 -0.0286 0.088 Uiso 1 1 calc R . . H14D H -0.0277 1.0000 -0.0939 0.088 Uiso 1 1 calc R . . C15B C 0.0309(6) 0.8764(5) -0.1302(3) 0.0861(16) Uani 1 1 d . . . H15A H 0.1271 0.9087 -0.1589 0.103 Uiso 1 1 calc R . . H15B H -0.0316 0.8904 -0.1673 0.103 Uiso 1 1 calc R . . C16B C 0.0501(8) 0.7591(5) -0.0958(4) 0.101(2) Uani 1 1 d . . . H16A H 0.1130 0.7455 -0.0589 0.121 Uiso 1 1 calc R . . H16B H -0.0461 0.7272 -0.0667 0.121 Uiso 1 1 calc R . . C17B C 0.1158(9) 0.7081(6) -0.1547(5) 0.118(2) Uani 1 1 d . . . H17A H 0.2166 0.7343 -0.1794 0.142 Uiso 1 1 calc R . . H17B H 0.0599 0.7287 -0.1951 0.142 Uiso 1 1 calc R . . C18B C 0.1192(12) 0.5913(7) -0.1227(6) 0.156(4) Uani 1 1 d . . . H18A H 0.0201 0.5646 -0.0939 0.187 Uiso 1 1 calc R . . H18B H 0.1835 0.5701 -0.0863 0.187 Uiso 1 1 calc R . . C19B C 0.1732(14) 0.5436(9) -0.1860(8) 0.202(5) Uani 1 1 d . . . H19D H 0.1752 0.4697 -0.1622 0.304 Uiso 1 1 calc R . . H19E H 0.2712 0.5697 -0.2149 0.304 Uiso 1 1 calc R . . H19F H 0.1073 0.5615 -0.2209 0.304 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 O1 0.122(4) 0.111(4) 0.204(6) -0.057(4) -0.032(4) 0.000(3) I1 0.0811(3) 0.0870(3) 0.0600(2) -0.00179(17) -0.01760(18) -0.00713(19) N3 0.072(3) 0.056(2) 0.055(2) -0.0191(18) -0.0130(19) -0.0001(19) N4 0.078(3) 0.049(2) 0.0431(19) -0.0140(16) -0.0093(18) 0.0003(18) C1A 0.080(3) 0.053(3) 0.052(3) -0.015(2) -0.017(2) 0.004(2) C2A 0.067(3) 0.041(2) 0.049(2) -0.0183(18) -0.015(2) 0.007(2) C3A 0.086(4) 0.050(3) 0.066(3) -0.024(2) -0.021(3) 0.004(2) C4A 0.103(4) 0.060(3) 0.078(4) -0.023(3) -0.051(3) 0.015(3) C5A 0.131(5) 0.050(3) 0.055(3) -0.006(2) -0.030(3) -0.002(3) C6A 0.096(4) 0.051(3) 0.050(3) -0.009(2) -0.013(3) -0.007(3) C7A 0.079(3) 0.044(2) 0.053(2) -0.017(2) -0.014(2) -0.005(2) C8A 0.096(4) 0.067(3) 0.048(3) -0.011(2) -0.002(3) 0.002(3) C9A 0.094(4) 0.071(3) 0.061(3) -0.008(3) -0.003(3) -0.012(3) C10A 0.110(5) 0.065(3) 0.092(4) -0.013(3) -0.016(4) -0.006(3) C11A 0.131(6) 0.070(4) 0.102(5) -0.020(3) -0.014(4) -0.013(4) C12A 0.170(8) 0.082(4) 0.123(6) -0.039(4) -0.038(6) 0.013(5) C13A 0.249(12) 0.092(5) 0.177(9) -0.071(6) -0.045(9) -0.009(6) C14A 0.077(4) 0.077(3) 0.075(3) -0.028(3) -0.011(3) -0.010(3) C15A 0.090(5) 0.099(5) 0.111(5) -0.037(4) 0.000(4) -0.004(4) C16A 0.122(6) 0.110(6) 0.115(6) -0.043(5) -0.002(5) 0.002(5) C17A 0.159(8) 0.118(6) 0.126(6) -0.055(5) -0.003(6) 0.044(6) C18A 0.178(10) 0.148(9) 0.172(9) -0.085(8) -0.001(8) -0.001(7) C19A 0.206(11) 0.188(10) 0.205(11) -0.135(10) -0.013(9) 0.020(9) I2 0.0758(3) 0.0939(3) 0.0675(2) 0.00142(19) -0.01998(18) -0.0132(2) N1 0.065(2) 0.060(2) 0.054(2) -0.0111(18) -0.0130(18) -0.0080(19) N2 0.073(3) 0.054(2) 0.048(2) -0.0091(17) -0.0132(18) -0.0055(19) C1B 0.074(3) 0.063(3) 0.059(3) -0.010(2) -0.025(2) -0.001(2) C2B 0.064(3) 0.051(2) 0.047(2) -0.0138(19) -0.012(2) -0.002(2) C3B 0.064(3) 0.063(3) 0.068(3) -0.022(2) -0.014(2) -0.003(2) C4B 0.081(3) 0.069(3) 0.062(3) -0.015(2) -0.030(3) 0.003(3) C5B 0.106(4) 0.063(3) 0.053(3) -0.012(2) -0.033(3) -0.002(3) C6B 0.092(4) 0.058(3) 0.048(2) -0.007(2) -0.013(2) -0.018(3) C7B 0.071(3) 0.051(2) 0.048(2) -0.014(2) -0.019(2) 0.000(2) C8B 0.090(4) 0.058(3) 0.042(2) -0.003(2) -0.008(2) -0.007(3) C9B 0.103(4) 0.059(3) 0.071(3) -0.012(3) -0.015(3) -0.010(3) C10B 0.110(5) 0.062(3) 0.094(4) -0.004(3) -0.024(4) -0.011(3) C11B 0.180(8) 0.096(5) 0.113(6) -0.017(4) -0.034(6) -0.051(5) C12B 0.215(10) 0.097(5) 0.116(6) -0.017(5) -0.034(7) -0.038(6) C13B 0.219(10) 0.088(5) 0.137(7) -0.051(5) -0.033(7) -0.024(6) C14B 0.062(3) 0.073(3) 0.076(3) -0.015(3) -0.013(3) -0.013(2) C15B 0.075(4) 0.093(4) 0.078(4) -0.020(3) -0.004(3) -0.019(3) C16B 0.102(5) 0.102(5) 0.090(4) -0.028(4) -0.017(4) 0.006(4) C17B 0.114(6) 0.126(6) 0.111(5) -0.048(5) -0.010(4) 0.006(5) C18B 0.176(9) 0.133(7) 0.171(9) -0.080(7) -0.030(7) 0.042(7) C19B 0.221(13) 0.178(10) 0.240(14) -0.111(11) -0.058(11) 0.030(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 N3 C1A 1.319(6) . ? N3 C7A 1.401(6) . ? N3 C14A 1.471(6) . ? N4 C1A 1.327(6) . ? N4 C2A 1.394(5) . ? N4 C8A 1.473(6) . ? C2A C7A 1.399(6) . ? C2A C3A 1.405(6) . ? C3A C4A 1.379(7) . ? C4A C5A 1.403(8) . ? C5A C6A 1.382(8) . ? C6A C7A 1.382(6) . ? C8A C9A 1.495(8) . ? C9A C10A 1.507(8) . ? C10A C11A 1.522(9) . ? C11A C12A 1.460(10) . ? C12A C13A 1.509(10) . ? C14A C15A 1.516(9) . ? C15A C16A 1.434(10) . ? C16A C17A 1.558(10) . ? C17A C18A 1.394(12) . ? C18A C19A 1.444(12) . ? N1 C1B 1.333(6) . ? N1 C7B 1.402(6) . ? N1 C14B 1.474(6) . ? N2 C1B 1.325(6) . ? N2 C2B 1.383(5) . ? N2 C8B 1.481(6) . ? C2B C7B 1.376(6) . ? C2B C3B 1.419(6) . ? C3B C4B 1.385(6) . ? C4B C5B 1.400(7) . ? C5B C6B 1.361(7) . ? C6B C7B 1.403(6) . ? C8B C9B 1.499(7) . ? C9B C10B 1.503(7) . ? C10B C11B 1.576(10) . ? C11B C12B 1.395(10) . ? C12B C13B 1.498(10) . ? C14B C15B 1.507(8) . ? C15B C16B 1.532(8) . ? C16B C17B 1.500(10) . ? C17B C18B 1.510(11) . ? C18B C19B 1.520(13) . ? 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 C1A N3 C7A 107.8(4) . . ? C1A N3 C14A 125.9(4) . . ? C7A N3 C14A 126.3(4) . . ? C1A N4 C2A 108.0(4) . . ? C1A N4 C8A 126.8(4) . . ? C2A N4 C8A 125.2(4) . . ? N3 C1A N4 111.4(4) . . ? N4 C2A C7A 106.3(4) . . ? N4 C2A C3A 131.7(4) . . ? C7A C2A C3A 121.9(4) . . ? C4A C3A C2A 116.6(5) . . ? C3A C4A C5A 120.8(5) . . ? C6A C5A C4A 122.8(5) . . ? C7A C6A C5A 116.7(5) . . ? C6A C7A C2A 121.2(5) . . ? C6A C7A N3 132.3(5) . . ? C2A C7A N3 106.4(4) . . ? N4 C8A C9A 111.8(4) . . ? C8A C9A C10A 113.6(5) . . ? C9A C10A C11A 113.7(6) . . ? C12A C11A C10A 115.5(7) . . ? C11A C12A C13A 114.2(8) . . ? N3 C14A C15A 112.1(5) . . ? C16A C15A C14A 117.0(6) . . ? C15A C16A C17A 115.9(7) . . ? C18A C17A C16A 119.5(8) . . ? C17A C18A C19A 117.9(10) . . ? C1B N1 C7B 107.5(4) . . ? C1B N1 C14B 125.6(4) . . ? C7B N1 C14B 126.6(4) . . ? C1B N2 C2B 108.3(4) . . ? C1B N2 C8B 124.9(4) . . ? C2B N2 C8B 126.6(4) . . ? N2 C1B N1 110.5(4) . . ? C7B C2B N2 107.2(4) . . ? C7B C2B C3B 121.3(4) . . ? N2 C2B C3B 131.4(4) . . ? C4B C3B C2B 116.4(5) . . ? C3B C4B C5B 121.2(5) . . ? C6B C5B C4B 122.6(4) . . ? C5B C6B C7B 116.9(5) . . ? C2B C7B N1 106.5(4) . . ? C2B C7B C6B 121.6(4) . . ? N1 C7B C6B 131.8(4) . . ? N2 C8B C9B 111.5(4) . . ? C8B C9B C10B 112.5(5) . . ? C9B C10B C11B 110.3(6) . . ? C12B C11B C10B 115.9(7) . . ? C11B C12B C13B 114.3(8) . . ? N1 C14B C15B 111.1(4) . . ? C14B C15B C16B 113.9(5) . . ? C17B C16B C15B 115.1(6) . . ? C16B C17B C18B 115.7(7) . . ? C17B C18B C19B 113.2(9) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.629 _refine_diff_density_min -0.881 _refine_diff_density_rms 0.082