# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_20130441 _audit_creation_date 2013-04-22 _audit_creation_method ; Olex2 1.2 (compiled Apr 9 2013 14:06:00, GUI svn.r4456) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(I), H2 O, 2(C13 H26 N3)' _chemical_formula_sum 'C26 H54 I2 N6 O' _chemical_formula_weight 720.55 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula C20H20N4O4 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 11.6885(2) _cell_length_b 16.3224(2) _cell_length_c 17.9468(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3423.96(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5245 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 66.9527 _cell_measurement_theta_min 3.6574 _exptl_absorpt_coefficient_mu 14.616 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.61371 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0886 _diffrn_reflns_av_unetI/netI 0.0745 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 12579 _diffrn_reflns_theta_full 67.06 _diffrn_reflns_theta_max 67.06 _diffrn_reflns_theta_min 3.66 _diffrn_ambient_temperature 291.15 _diffrn_detector_area_resol_mean 16.2312 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -77.00 -33.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 178.0000 -90.0000 44 #__ type_ start__ end____ width___ exp.time_ 2 omega -77.00 -52.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 178.0000 -30.0000 25 #__ type_ start__ end____ width___ exp.time_ 3 omega -11.00 16.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 30.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 4 omega -49.00 13.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 37.0000 -120.0000 62 #__ type_ start__ end____ width___ exp.time_ 5 omega -1.00 28.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 37.0000 90.0000 29 #__ type_ start__ end____ width___ exp.time_ 6 omega -48.00 30.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 30.0000 -60.0000 78 #__ type_ start__ end____ width___ exp.time_ 7 omega 35.00 117.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 56.0000 57.0000 0.0000 82 #__ type_ start__ end____ width___ exp.time_ 8 omega 84.00 130.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -61.0000 -180.0000 46 #__ type_ start__ end____ width___ exp.time_ 9 omega 52.00 77.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -61.0000 -180.0000 25 #__ type_ start__ end____ width___ exp.time_ 10 omega 107.00 176.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 77.0000 -30.0000 69 #__ type_ start__ end____ width___ exp.time_ 11 omega 54.00 90.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -30.0000 -30.0000 36 #__ type_ start__ end____ width___ exp.time_ 12 omega 126.00 176.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 61.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 13 omega 40.00 103.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -94.0000 -30.0000 63 #__ type_ start__ end____ width___ exp.time_ 14 omega 63.00 90.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -45.0000 90.0000 27 #__ type_ start__ end____ width___ exp.time_ 15 omega 82.00 108.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 178.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 16 omega 50.00 96.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 -45.0000 -60.0000 46 #__ type_ start__ end____ width___ exp.time_ 17 omega 82.00 177.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 112.0000 77.0000 30.0000 95 #__ type_ start__ end____ width___ exp.time_ 18 omega -72.00 26.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -37.0000 90.0000 98 #__ type_ start__ end____ width___ exp.time_ 19 omega 26.00 75.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 56.0000 77.0000 150.0000 49 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0935006000 _diffrn_orient_matrix_UB_12 0.0231897000 _diffrn_orient_matrix_UB_13 -0.0566950000 _diffrn_orient_matrix_UB_21 -0.0591468000 _diffrn_orient_matrix_UB_22 0.0830943000 _diffrn_orient_matrix_UB_23 -0.0132170000 _diffrn_orient_matrix_UB_31 0.0715201000 _diffrn_orient_matrix_UB_32 0.0382916000 _diffrn_orient_matrix_UB_33 0.0631345000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'Enhance (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5543 _reflns_number_total 6107 _reflns_odcompleteness_completeness 99.94 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.853 _refine_diff_density_min -0.912 _refine_diff_density_rms 0.110 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.009(8) _refine_ls_extinction_coef 0.00117(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 326 _refine_ls_number_reflns 6107 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0510 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0635P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1269 _refine_ls_wR_factor_ref 0.1320 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H,H) groups 2.a Riding coordinates: I1(O1,H1A,H1B) 2.b Ternary CH refined with riding coordinates: C2(H2), C2'(H2'), C6(H6), C6'(H6') 2.c Secondary CH2 refined with riding coordinates: C3(H3A,H3B), C3'(H3'A,H3'B), C5(H5A,H5B), C5'(H5'A,H5'B) 2.d Aromatic/amide H refined with riding coordinates: N1(H1), N1'(H1'), N3(H3), N3'(H3') 2.e Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C8'(H8'A,H8'B,H8'C), C9(H9A,H9B,H9C), C9'(H9'A,H9'B,H9'C), C10(H10A,H10B,H10C), C10'(H10D,H10E,H10F), C11(H11A,H11B,H11C), C11'(H11D,H11E, H11F), C12(H12A,H12B,H12C), C12'(H12D,H12E,H12F), C13(H13A,H13B,H13C), C13'(H13D,H13E,H13F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.52667(5) 0.39350(3) 0.54067(3) 0.06049(17) Uani 1 1 d . . . O1 O 0.45465(5) 0.27891(3) 0.69536(3) 0.0641(16) Uani 1 1 d R . . H1A H 0.4372 0.3024 0.6547 0.096 Uiso 1 1 d R . . H1B H 0.4374 0.3047 0.7349 0.096 Uiso 1 1 d R . . I1' I 0.11510(5) 0.61747(3) 0.35451(3) 0.06505(18) Uani 1 1 d . . . N1 N 0.8868(5) 0.3708(3) 0.3702(3) 0.0444(12) Uani 1 1 d . . . H1 H 0.8875 0.3271 0.3434 0.053 Uiso 1 1 calc R . . N1' N 0.4145(6) 0.7345(3) 0.5886(3) 0.0526(15) Uani 1 1 d . . . H1' H 0.4491 0.7806 0.5938 0.063 Uiso 1 1 calc R . . N2 N 0.8903(6) 0.4488(3) 0.4706(3) 0.0470(12) Uani 1 1 d . . . N2' N 0.3159(4) 0.6247(3) 0.6198(2) 0.0380(11) Uani 1 1 d . . . N3 N 0.9413(5) 0.3214(3) 0.4923(3) 0.0445(12) Uani 1 1 d . . . H3 H 0.9566 0.2707 0.4837 0.053 Uiso 1 1 calc R . . N3' N 0.3818(5) 0.6935(3) 0.7164(3) 0.0468(13) Uani 1 1 d . . . H3' H 0.4138 0.7325 0.7410 0.056 Uiso 1 1 calc R . . C1 C 0.7769(6) 0.4587(5) 0.2784(5) 0.0573(19) Uani 1 1 d . . . C1' C 0.4956(7) 0.6911(6) 0.4644(4) 0.059(2) Uani 1 1 d . . . C2 C 0.8612(5) 0.4542(4) 0.3435(4) 0.0449(14) Uani 1 1 d . . . H2 H 0.9334 0.4785 0.3266 0.054 Uiso 1 1 calc R . . C2' C 0.3900(6) 0.6937(4) 0.5161(3) 0.0458(14) Uani 1 1 d . . . H2' H 0.3295 0.7247 0.4909 0.055 Uiso 1 1 calc R . . C3 C 0.8270(6) 0.4976(4) 0.4163(4) 0.0524(16) Uani 1 1 d . . . H3A H 0.8513 0.5544 0.4166 0.063 Uiso 1 1 calc R . . H3B H 0.7452 0.4948 0.4248 0.063 Uiso 1 1 calc R . . C3' C 0.3403(5) 0.6109(4) 0.5402(3) 0.0419(13) Uani 1 1 d . . . H3'A H 0.2711 0.5980 0.5128 0.050 Uiso 1 1 calc R . . H3'B H 0.3953 0.5671 0.5333 0.050 Uiso 1 1 calc R . . C4 C 0.9086(5) 0.3745(4) 0.4421(3) 0.0389(12) Uani 1 1 d . . . C4' C 0.3757(5) 0.6898(3) 0.6422(3) 0.0354(11) Uani 1 1 d . . . C5 C 0.8809(6) 0.4428(4) 0.5510(4) 0.0490(15) Uani 1 1 d . . . H5A H 0.8018 0.4384 0.5667 0.059 Uiso 1 1 calc R . . H5B H 0.9161 0.4894 0.5755 0.059 Uiso 1 1 calc R . . C5' C 0.2985(6) 0.5690(4) 0.6804(3) 0.0412(13) Uani 1 1 d . . . H5'A H 0.3497 0.5224 0.6767 0.049 Uiso 1 1 calc R . . H5'B H 0.2201 0.5494 0.6815 0.049 Uiso 1 1 calc R . . C6 C 0.9483(6) 0.3621(4) 0.5665(3) 0.0408(13) Uani 1 1 d . . . H6 H 0.9058 0.3293 0.6029 0.049 Uiso 1 1 calc R . . C6' C 0.3259(5) 0.6211(4) 0.7503(3) 0.0365(12) Uani 1 1 d . . . H6' H 0.3824 0.5918 0.7806 0.044 Uiso 1 1 calc R . . C7 C 1.0726(6) 0.3731(4) 0.5944(3) 0.0429(14) Uani 1 1 d . . . C7' C 0.2250(5) 0.6460(3) 0.8006(3) 0.0328(12) Uani 1 1 d . . . C8 C 0.8304(9) 0.4180(6) 0.2099(5) 0.075(3) Uani 1 1 d . . . H8A H 0.9025 0.4435 0.1991 0.112 Uiso 1 1 calc R . . H8B H 0.7801 0.4242 0.1680 0.112 Uiso 1 1 calc R . . H8C H 0.8422 0.3608 0.2198 0.112 Uiso 1 1 calc R . . C8' C 0.4646(10) 0.6383(8) 0.3970(5) 0.102(4) Uani 1 1 d . . . H8'A H 0.4449 0.5841 0.4133 0.153 Uiso 1 1 calc R . . H8'B H 0.5288 0.6355 0.3637 0.153 Uiso 1 1 calc R . . H8'C H 0.4005 0.6622 0.3715 0.153 Uiso 1 1 calc R . . C9 C 0.7596(9) 0.5513(6) 0.2599(6) 0.080(3) Uani 1 1 d . . . H9A H 0.7233 0.5780 0.3013 0.120 Uiso 1 1 calc R . . H9B H 0.7122 0.5564 0.2165 0.120 Uiso 1 1 calc R . . H9C H 0.8325 0.5763 0.2506 0.120 Uiso 1 1 calc R . . C9' C 0.5230(10) 0.7796(7) 0.4419(5) 0.092(4) Uani 1 1 d . . . H9'A H 0.4567 0.8041 0.4195 0.138 Uiso 1 1 calc R . . H9'B H 0.5850 0.7799 0.4068 0.138 Uiso 1 1 calc R . . H9'C H 0.5444 0.8104 0.4853 0.138 Uiso 1 1 calc R . . C10 C 0.6630(8) 0.4198(8) 0.2980(6) 0.087(3) Uani 1 1 d . . . H10A H 0.6757 0.3655 0.3170 0.131 Uiso 1 1 calc R . . H10B H 0.6161 0.4169 0.2542 0.131 Uiso 1 1 calc R . . H10C H 0.6252 0.4523 0.3351 0.131 Uiso 1 1 calc R . . C10' C 0.5976(7) 0.6533(6) 0.5042(5) 0.073(2) Uani 1 1 d . . . H10D H 0.6146 0.6846 0.5482 0.109 Uiso 1 1 calc R . . H10E H 0.6628 0.6537 0.4717 0.109 Uiso 1 1 calc R . . H10F H 0.5799 0.5979 0.5180 0.109 Uiso 1 1 calc R . . C11 C 1.0648(8) 0.4038(5) 0.6758(4) 0.0601(19) Uani 1 1 d . . . H11A H 1.0386 0.4595 0.6763 0.090 Uiso 1 1 calc R . . H11B H 1.1390 0.4007 0.6986 0.090 Uiso 1 1 calc R . . H11C H 1.0121 0.3701 0.7031 0.090 Uiso 1 1 calc R . . C11' C 0.1343(6) 0.6923(5) 0.7572(4) 0.0511(16) Uani 1 1 d . . . H11D H 0.1661 0.7425 0.7386 0.077 Uiso 1 1 calc R . . H11E H 0.0709 0.7043 0.7894 0.077 Uiso 1 1 calc R . . H11F H 0.1086 0.6593 0.7162 0.077 Uiso 1 1 calc R . . C12 C 1.1324(8) 0.2903(5) 0.5932(5) 0.067(2) Uani 1 1 d . . . H12A H 1.0930 0.2531 0.6257 0.101 Uiso 1 1 calc R . . H12B H 1.2100 0.2967 0.6098 0.101 Uiso 1 1 calc R . . H12C H 1.1320 0.2689 0.5434 0.101 Uiso 1 1 calc R . . C12' C 0.1735(7) 0.5688(4) 0.8346(4) 0.0540(17) Uani 1 1 d . . . H12D H 0.1408 0.5356 0.7959 0.081 Uiso 1 1 calc R . . H12E H 0.1150 0.5836 0.8697 0.081 Uiso 1 1 calc R . . H12F H 0.2323 0.5383 0.8597 0.081 Uiso 1 1 calc R . . C13 C 1.1405(6) 0.4328(5) 0.5471(4) 0.0558(17) Uani 1 1 d . . . H13A H 1.1338 0.4179 0.4955 0.084 Uiso 1 1 calc R . . H13B H 1.2195 0.4313 0.5616 0.084 Uiso 1 1 calc R . . H13C H 1.1110 0.4872 0.5541 0.084 Uiso 1 1 calc R . . C13' C 0.2716(6) 0.7021(5) 0.8624(4) 0.0527(17) Uani 1 1 d . . . H13D H 0.3391 0.6780 0.8835 0.079 Uiso 1 1 calc R . . H13E H 0.2147 0.7085 0.9005 0.079 Uiso 1 1 calc R . . H13F H 0.2900 0.7547 0.8417 0.079 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0712(3) 0.0406(2) 0.0696(3) 0.0038(2) -0.0052(2) 0.0014(2) O1 0.096(5) 0.042(3) 0.054(3) -0.0014(19) -0.009(3) 0.019(3) I1' 0.0681(3) 0.0495(3) 0.0775(3) -0.0032(2) -0.0182(2) 0.0226(2) N1 0.047(3) 0.044(3) 0.042(2) -0.003(2) -0.008(2) 0.009(3) N1' 0.063(4) 0.041(3) 0.054(3) -0.010(2) 0.029(3) -0.020(3) N2 0.053(3) 0.040(3) 0.048(3) -0.003(2) 0.001(3) 0.010(3) N2' 0.040(3) 0.040(3) 0.034(2) -0.009(2) 0.0053(19) -0.015(2) N3 0.057(3) 0.032(2) 0.045(3) -0.003(2) -0.010(2) -0.003(2) N3' 0.048(3) 0.052(3) 0.040(2) -0.017(2) 0.010(2) -0.028(3) C1 0.036(3) 0.068(5) 0.068(4) 0.027(4) 0.001(3) 0.004(3) C1' 0.054(4) 0.084(5) 0.039(3) -0.012(3) 0.019(3) -0.026(4) C2 0.034(3) 0.044(3) 0.057(4) 0.006(3) 0.005(3) 0.006(3) C2' 0.041(3) 0.055(4) 0.041(3) 0.000(3) 0.010(3) -0.007(3) C3 0.044(4) 0.045(4) 0.068(4) 0.001(3) 0.003(3) 0.016(3) C3' 0.039(3) 0.047(3) 0.039(3) -0.012(3) 0.011(2) -0.006(3) C4 0.033(3) 0.039(3) 0.044(3) 0.000(2) 0.002(2) -0.004(2) C4' 0.027(3) 0.034(3) 0.045(3) -0.008(2) 0.006(3) -0.007(2) C5 0.043(3) 0.052(4) 0.052(3) -0.011(3) 0.008(3) 0.002(3) C5' 0.045(3) 0.031(3) 0.048(3) -0.005(2) 0.006(3) -0.008(3) C6 0.040(3) 0.044(3) 0.039(3) 0.001(2) 0.004(2) -0.012(3) C6' 0.031(3) 0.037(3) 0.042(3) 0.003(2) 0.001(2) -0.004(3) C7 0.045(3) 0.039(3) 0.045(3) 0.000(3) 0.000(3) -0.013(3) C7' 0.031(3) 0.032(3) 0.036(3) 0.005(2) 0.002(2) 0.005(2) C8 0.075(6) 0.088(7) 0.062(4) 0.014(4) -0.001(4) 0.014(5) C8' 0.093(7) 0.156(12) 0.056(4) -0.041(6) 0.035(5) -0.053(8) C9 0.073(6) 0.077(6) 0.091(6) 0.034(5) -0.011(5) 0.018(5) C9' 0.099(8) 0.115(9) 0.061(5) 0.023(5) 0.034(5) -0.039(7) C10 0.054(5) 0.114(9) 0.095(6) 0.039(6) -0.012(5) -0.024(5) C10' 0.050(4) 0.085(6) 0.084(6) -0.019(5) 0.013(4) -0.007(4) C11 0.066(5) 0.065(5) 0.049(3) -0.001(3) -0.008(3) -0.021(4) C11' 0.037(3) 0.063(4) 0.054(3) 0.009(3) -0.002(3) 0.014(3) C12 0.064(5) 0.055(4) 0.083(5) 0.000(4) -0.028(4) 0.006(4) C12' 0.056(4) 0.050(4) 0.056(4) 0.013(3) 0.017(3) 0.002(3) C13 0.048(4) 0.059(4) 0.061(4) 0.001(3) 0.010(3) -0.016(3) C13' 0.053(4) 0.062(4) 0.043(3) -0.012(3) -0.001(3) 0.007(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 H1A 0.8494 . ? O1 H1B 0.8499 . ? N1 H1 0.8600 . ? N1 C2 1.475(8) . ? N1 C4 1.317(8) . ? N1' H1' 0.8600 . ? N1' C2' 1.488(8) . ? N1' C4' 1.290(8) . ? N2 C3 1.460(9) . ? N2 C4 1.334(8) . ? N2 C5 1.450(8) . ? N2' C3' 1.474(7) . ? N2' C4' 1.334(7) . ? N2' C5' 1.433(8) . ? N3 H3 0.8600 . ? N3 C4 1.306(8) . ? N3 C6 1.492(8) . ? N3' H3' 0.8600 . ? N3' C4' 1.334(8) . ? N3' C6' 1.482(8) . ? C1 C2 1.529(10) . ? C1 C8 1.531(12) . ? C1 C9 1.560(11) . ? C1 C10 1.517(11) . ? C1' C2' 1.546(8) . ? C1' C8' 1.529(10) . ? C1' C9' 1.535(13) . ? C1' C10' 1.521(13) . ? C2 H2 0.9800 . ? C2 C3 1.539(9) . ? C2' H2' 0.9800 . ? C2' C3' 1.534(9) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3' H3'A 0.9700 . ? C3' H3'B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 C6 1.560(9) . ? C5' H5'A 0.9700 . ? C5' H5'B 0.9700 . ? C5' C6' 1.549(8) . ? C6 H6 0.9800 . ? C6 C7 1.547(9) . ? C6' H6' 0.9800 . ? C6' C7' 1.540(8) . ? C7 C11 1.548(9) . ? C7 C12 1.521(10) . ? C7 C13 1.517(9) . ? C7' C11' 1.516(8) . ? C7' C12' 1.525(8) . ? C7' C13' 1.537(9) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C8' H8'A 0.9600 . ? C8' H8'B 0.9600 . ? C8' H8'C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C9' H9'A 0.9600 . ? C9' H9'B 0.9600 . ? C9' H9'C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C10' H10D 0.9600 . ? C10' H10E 0.9600 . ? C10' H10F 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C11' H11D 0.9600 . ? C11' H11E 0.9600 . ? C11' H11F 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C12' H12D 0.9600 . ? C12' H12E 0.9600 . ? C12' H12F 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C13' H13D 0.9600 . ? C13' H13E 0.9600 . ? C13' H13F 0.9600 . ? 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 H1A O1 H1B 115.9 . . ? C2 N1 H1 125.8 . . ? C4 N1 H1 125.8 . . ? C4 N1 C2 108.4(5) . . ? C2' N1' H1' 125.3 . . ? C4' N1' H1' 125.3 . . ? C4' N1' C2' 109.4(5) . . ? C4 N2 C3 108.8(5) . . ? C4 N2 C5 109.4(5) . . ? C5 N2 C3 131.5(6) . . ? C4' N2' C3' 108.2(5) . . ? C4' N2' C5' 110.6(5) . . ? C5' N2' C3' 131.8(5) . . ? C4 N3 H3 125.2 . . ? C4 N3 C6 109.6(5) . . ? C6 N3 H3 125.2 . . ? C4' N3' H3' 124.7 . . ? C4' N3' C6' 110.5(5) . . ? C6' N3' H3' 124.7 . . ? C2 C1 C8 109.2(6) . . ? C2 C1 C9 107.1(7) . . ? C8 C1 C9 107.6(7) . . ? C10 C1 C2 111.6(6) . . ? C10 C1 C8 111.2(9) . . ? C10 C1 C9 109.9(8) . . ? C8' C1' C2' 107.6(6) . . ? C8' C1' C9' 111.8(8) . . ? C9' C1' C2' 107.3(7) . . ? C10' C1' C2' 110.8(6) . . ? C10' C1' C8' 109.3(9) . . ? C10' C1' C9' 110.0(8) . . ? N1 C2 C1 115.1(6) . . ? N1 C2 H2 107.4 . . ? N1 C2 C3 101.6(5) . . ? C1 C2 H2 107.4 . . ? C1 C2 C3 117.3(6) . . ? C3 C2 H2 107.4 . . ? N1' C2' C1' 112.6(6) . . ? N1' C2' H2' 108.2 . . ? N1' C2' C3' 102.8(5) . . ? C1' C2' H2' 108.2 . . ? C3' C2' C1' 116.5(6) . . ? C3' C2' H2' 108.2 . . ? N2 C3 C2 100.6(5) . . ? N2 C3 H3A 111.7 . . ? N2 C3 H3B 111.7 . . ? C2 C3 H3A 111.7 . . ? C2 C3 H3B 111.7 . . ? H3A C3 H3B 109.4 . . ? N2' C3' C2' 102.2(5) . . ? N2' C3' H3'A 111.3 . . ? N2' C3' H3'B 111.3 . . ? C2' C3' H3'A 111.3 . . ? C2' C3' H3'B 111.3 . . ? H3'A C3' H3'B 109.2 . . ? N1 C4 N2 112.7(6) . . ? N3 C4 N1 134.5(6) . . ? N3 C4 N2 112.7(5) . . ? N1' C4' N2' 114.1(5) . . ? N1' C4' N3' 134.5(6) . . ? N3' C4' N2' 111.4(5) . . ? N2 C5 H5A 111.5 . . ? N2 C5 H5B 111.5 . . ? N2 C5 C6 101.3(5) . . ? H5A C5 H5B 109.3 . . ? C6 C5 H5A 111.5 . . ? C6 C5 H5B 111.5 . . ? N2' C5' H5'A 111.0 . . ? N2' C5' H5'B 111.0 . . ? N2' C5' C6' 103.7(5) . . ? H5'A C5' H5'B 109.0 . . ? C6' C5' H5'A 111.0 . . ? C6' C5' H5'B 111.0 . . ? N3 C6 C5 100.9(5) . . ? N3 C6 H6 108.9 . . ? N3 C6 C7 113.1(5) . . ? C5 C6 H6 108.9 . . ? C7 C6 C5 115.7(5) . . ? C7 C6 H6 108.9 . . ? N3' C6' C5' 101.3(4) . . ? N3' C6' H6' 108.7 . . ? N3' C6' C7' 111.6(5) . . ? C5' C6' H6' 108.7 . . ? C7' C6' C5' 117.5(5) . . ? C7' C6' H6' 108.7 . . ? C6 C7 C11 106.7(6) . . ? C12 C7 C6 108.9(6) . . ? C12 C7 C11 109.1(6) . . ? C13 C7 C6 112.6(6) . . ? C13 C7 C11 110.5(6) . . ? C13 C7 C12 108.9(6) . . ? C11' C7' C6' 111.5(5) . . ? C11' C7' C12' 110.0(5) . . ? C11' C7' C13' 108.8(5) . . ? C12' C7' C6' 108.5(5) . . ? C12' C7' C13' 110.1(5) . . ? C13' C7' C6' 108.0(5) . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1' C8' H8'A 109.5 . . ? C1' C8' H8'B 109.5 . . ? C1' C8' H8'C 109.5 . . ? H8'A C8' H8'B 109.5 . . ? H8'A C8' H8'C 109.5 . . ? H8'B C8' H8'C 109.5 . . ? C1 C9 H9A 109.5 . . ? C1 C9 H9B 109.5 . . ? C1 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1' C9' H9'A 109.5 . . ? C1' C9' H9'B 109.5 . . ? C1' C9' H9'C 109.5 . . ? H9'A C9' H9'B 109.5 . . ? H9'A C9' H9'C 109.5 . . ? H9'B C9' H9'C 109.5 . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C1' C10' H10D 109.5 . . ? C1' C10' H10E 109.5 . . ? C1' C10' H10F 109.5 . . ? H10D C10' H10E 109.5 . . ? H10D C10' H10F 109.5 . . ? H10E C10' H10F 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7' C11' H11D 109.5 . . ? C7' C11' H11E 109.5 . . ? C7' C11' H11F 109.5 . . ? H11D C11' H11E 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C7' C12' H12D 109.5 . . ? C7' C12' H12E 109.5 . . ? C7' C12' H12F 109.5 . . ? H12D C12' H12E 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C7' C13' H13D 109.5 . . ? C7' C13' H13E 109.5 . . ? C7' C13' H13F 109.5 . . ? H13D C13' H13E 109.5 . . ? H13D C13' H13F 109.5 . . ? H13E C13' H13F 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A I1 0.85 2.74 3.452 142.7 . O1 H1B I1' 0.85 2.57 3.418 179.8 2_565 N1 H1 O1 0.86 2.02 2.825(5) 154.7 3_556 N1' H1' I1' 0.86 2.72 3.519(6) 155.4 3_566 N3 H3 I1 0.86 2.84 3.694(5) 175.0 3_556 N3' H3' O1 0.86 2.06 2.847(5) 151.8 4_656 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 N1 C2 C3 N2 26.6(7) . . . . ? N1' C2' C3' N2' 14.1(7) . . . . ? N2 C5 C6 N3 -22.1(6) . . . . ? N2 C5 C6 C7 100.3(6) . . . . ? N2' C5' C6' N3' -13.1(6) . . . . ? N2' C5' C6' C7' 108.7(6) . . . . ? N3 C6 C7 C11 -171.8(5) . . . . ? N3 C6 C7 C12 -54.1(7) . . . . ? N3 C6 C7 C13 66.7(7) . . . . ? N3' C6' C7' C11' 59.9(7) . . . . ? N3' C6' C7' C12' -178.9(5) . . . . ? N3' C6' C7' C13' -59.6(6) . . . . ? C1 C2 C3 N2 153.0(6) . . . . ? C1' C2' C3' N2' 137.7(6) . . . . ? C2 N1 C4 N2 6.2(8) . . . . ? C2 N1 C4 N3 -175.7(7) . . . . ? C2' N1' C4' N2' -5.9(8) . . . . ? C2' N1' C4' N3' 173.9(7) . . . . ? C3 N2 C4 N1 12.9(8) . . . . ? C3 N2 C4 N3 -165.6(6) . . . . ? C3 N2 C5 C6 163.9(7) . . . . ? C3' N2' C4' N1' 16.1(8) . . . . ? C3' N2' C4' N3' -163.8(6) . . . . ? C3' N2' C5' C6' 157.8(6) . . . . ? C4 N1 C2 C1 -149.0(6) . . . . ? C4 N1 C2 C3 -21.2(7) . . . . ? C4 N2 C3 C2 -24.8(7) . . . . ? C4 N2 C5 C6 23.9(7) . . . . ? C4 N3 C6 C5 14.7(7) . . . . ? C4 N3 C6 C7 -109.5(6) . . . . ? C4' N1' C2' C1' -132.3(7) . . . . ? C4' N1' C2' C3' -6.1(7) . . . . ? C4' N2' C3' C2' -18.2(7) . . . . ? C4' N2' C5' C6' 16.3(7) . . . . ? C4' N3' C6' C5' 6.5(7) . . . . ? C4' N3' C6' C7' -119.3(6) . . . . ? C5 N2 C3 C2 -165.1(7) . . . . ? C5 N2 C4 N1 162.4(6) . . . . ? C5 N2 C4 N3 -16.1(8) . . . . ? C5 C6 C7 C11 72.5(7) . . . . ? C5 C6 C7 C12 -169.8(6) . . . . ? C5 C6 C7 C13 -48.9(7) . . . . ? C5' N2' C3' C2' -160.4(6) . . . . ? C5' N2' C4' N1' 166.8(6) . . . . ? C5' N2' C4' N3' -13.0(7) . . . . ? C5' C6' C7' C11' -56.5(7) . . . . ? C5' C6' C7' C12' 64.8(7) . . . . ? C5' C6' C7' C13' -175.9(5) . . . . ? C6 N3 C4 N1 -178.3(7) . . . . ? C6 N3 C4 N2 -0.3(8) . . . . ? C6' N3' C4' N1' -176.4(7) . . . . ? C6' N3' C4' N2' 3.4(8) . . . . ? C8 C1 C2 N1 -64.9(8) . . . . ? C8 C1 C2 C3 175.6(7) . . . . ? C8' C1' C2' N1' 172.6(8) . . . . ? C8' C1' C2' C3' 54.2(10) . . . . ? C9 C1 C2 N1 178.8(6) . . . . ? C9 C1 C2 C3 59.3(9) . . . . ? C9' C1' C2' N1' -66.9(9) . . . . ? C9' C1' C2' C3' 174.7(7) . . . . ? C10 C1 C2 N1 58.5(10) . . . . ? C10 C1 C2 C3 -61.0(10) . . . . ? C10' C1' C2' N1' 53.2(9) . . . . ? C10' C1' C2' C3' -65.2(8) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 937953'