# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 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_exp_335 #TrackingRef 'exp_335.cif' _audit_creation_date 2012-10-29 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H18 I N O' _chemical_formula_sum 'C26 H18 I N O' _chemical_formula_weight 487.31 _chemical_melting_point ? 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.6284(4) _cell_length_b 11.7266(6) _cell_length_c 19.1651(9) _cell_angle_alpha 75.073(5) _cell_angle_beta 77.631(4) _cell_angle_gamma 87.141(4) _cell_volume 2042.32(17) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4658 _cell_measurement_temperature 293.83(10) _cell_measurement_theta_max 28.4848 _cell_measurement_theta_min 3.0168 _exptl_absorpt_coefficient_mu 1.585 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.96879 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light orange' _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 968 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_unetI/netI 0.0464 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 12142 _diffrn_reflns_theta_full 25.68 _diffrn_reflns_theta_max 25.68 _diffrn_reflns_theta_min 3.02 _diffrn_ambient_temperature 293.83(10) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.9175 _diffrn_measured_fraction_theta_max 0.9628 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 12.00 50.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -19.3492 57.0000 -150.0000 38 #__ type_ start__ end____ width___ exp.time_ 2 omega -13.00 14.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -19.3492 -99.0000 -30.0000 27 #__ type_ start__ end____ width___ exp.time_ 3 omega 39.00 66.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 -99.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 4 omega -1.00 42.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 57.0000 -60.0000 43 #__ type_ start__ end____ width___ exp.time_ 5 omega 36.00 61.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 178.0000 120.0000 25 #__ type_ start__ end____ width___ exp.time_ 6 omega 6.00 93.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 57.0000 -180.0000 87 #__ type_ start__ end____ width___ exp.time_ 7 omega -1.00 90.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 57.0000 90.0000 91 #__ type_ start__ end____ width___ exp.time_ 8 omega -48.00 -20.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 -57.0000 -60.0000 28 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0340843000 _diffrn_orient_matrix_UB_12 0.0258136000 _diffrn_orient_matrix_UB_13 -0.0370607000 _diffrn_orient_matrix_UB_21 -0.0216026000 _diffrn_orient_matrix_UB_22 -0.0485839000 _diffrn_orient_matrix_UB_23 -0.0108914000 _diffrn_orient_matrix_UB_31 -0.0637152000 _diffrn_orient_matrix_UB_32 0.0298660000 _diffrn_orient_matrix_UB_33 -0.0064604000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5491 _reflns_number_total 7160 _reflns_odcompleteness_completeness 91.75 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _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 0.617 _refine_diff_density_min -0.803 _refine_diff_density_rms 0.066 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 523 _refine_ls_number_reflns 7160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0393 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0227P)^2^+1.0796P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.0810 _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. ; _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 1.19609(3) 0.72403(3) 0.432003(17) 0.06094(11) Uani 1 1 d . . . I2 I 0.63268(3) 0.64883(3) 1.071436(18) 0.06133(11) Uani 1 1 d . . . O1 O 1.0570(3) 0.5140(3) 0.58749(16) 0.0553(8) Uani 1 1 d . . . O2 O 0.6556(3) 0.6086(3) 0.89912(17) 0.0599(8) Uani 1 1 d . . . N1 N 0.8417(3) 0.6085(3) 0.60556(17) 0.0391(8) Uani 1 1 d . . . N2 N 0.4368(3) 0.6912(3) 0.88920(16) 0.0384(8) Uani 1 1 d . . . C1 C 0.7135(4) 0.7933(3) 0.6131(2) 0.0392(9) Uani 1 1 d . . . C2 C 0.7870(5) 0.8128(4) 0.6636(2) 0.0528(11) Uani 1 1 d . . . H2 H 0.8653 0.7664 0.6732 0.063 Uiso 1 1 calc R . . C3 C 0.7449(6) 0.9009(5) 0.6998(3) 0.0724(15) Uani 1 1 d . . . H3 H 0.7946 0.9133 0.7338 0.087 Uiso 1 1 calc R . . C4 C 0.6298(6) 0.9699(5) 0.6856(3) 0.0766(17) Uani 1 1 d . . . H4 H 0.6025 1.0299 0.7093 0.092 Uiso 1 1 calc R . . C5 C 0.5546(5) 0.9500(4) 0.6359(3) 0.0652(14) Uani 1 1 d . . . H5 H 0.4757 0.9961 0.6272 0.078 Uiso 1 1 calc R . . C6 C 0.5946(4) 0.8625(4) 0.5988(2) 0.0468(11) Uani 1 1 d . . . C7 C 0.5204(4) 0.8431(4) 0.5443(3) 0.0541(12) Uani 1 1 d . . . H7 H 0.4519 0.8973 0.5293 0.065 Uiso 1 1 calc R . . C8 C 0.5461(4) 0.7517(4) 0.5150(2) 0.0491(11) Uani 1 1 d . . . H8 H 0.4999 0.7461 0.4780 0.059 Uiso 1 1 calc R . . C9 C 0.6480(4) 0.6568(3) 0.5399(2) 0.0353(9) Uani 1 1 d . . . H9 H 0.6929 0.6270 0.4972 0.042 Uiso 1 1 calc R . . C10 C 0.7673(4) 0.7069(3) 0.56667(19) 0.0338(9) Uani 1 1 d . . . C11 C 0.5688(4) 0.5542(3) 0.59854(19) 0.0340(9) Uani 1 1 d . . . C12 C 0.4381(4) 0.5175(3) 0.5903(2) 0.0394(9) Uani 1 1 d . . . H12 H 0.4000 0.5582 0.5503 0.047 Uiso 1 1 calc R . . C13 C 0.3654(5) 0.4225(4) 0.6402(2) 0.0513(11) Uani 1 1 d . . . H13 H 0.2795 0.3987 0.6336 0.062 Uiso 1 1 calc R . . C14 C 0.4204(5) 0.3626(4) 0.7002(3) 0.0614(13) Uani 1 1 d . . . H14 H 0.3711 0.2987 0.7344 0.074 Uiso 1 1 calc R . . C15 C 0.5485(5) 0.3974(4) 0.7096(2) 0.0540(12) Uani 1 1 d . . . H15 H 0.5849 0.3569 0.7503 0.065 Uiso 1 1 calc R . . C16 C 0.6236(4) 0.4925(3) 0.6587(2) 0.0389(9) Uani 1 1 d . . . C17 C 0.7665(4) 0.5249(4) 0.6700(2) 0.0466(10) Uani 1 1 d . . . H17A H 0.7518 0.5586 0.7122 0.056 Uiso 1 1 calc R . . H17B H 0.8232 0.4542 0.6804 0.056 Uiso 1 1 calc R . . C18 C 0.9769(4) 0.5945(4) 0.5691(2) 0.0420(10) Uani 1 1 d . . . C19 C 1.0016(4) 0.6977(3) 0.5039(2) 0.0374(9) Uani 1 1 d . . . C20 C 0.8862(4) 0.7636(3) 0.5004(2) 0.0361(9) Uani 1 1 d . . . C21 C 0.8669(4) 0.8701(3) 0.44219(19) 0.0363(9) Uani 1 1 d . . . C22 C 0.8570(4) 0.9823(4) 0.4542(2) 0.0432(10) Uani 1 1 d . . . H22 H 0.8576 0.9916 0.5008 0.052 Uiso 1 1 calc R . . C23 C 0.8462(4) 1.0802(4) 0.3972(3) 0.0572(12) Uani 1 1 d . . . H23 H 0.8406 1.1550 0.4058 0.069 Uiso 1 1 calc R . . C24 C 0.8436(5) 1.0679(5) 0.3283(3) 0.0650(13) Uani 1 1 d . . . H24 H 0.8359 1.1341 0.2903 0.078 Uiso 1 1 calc R . . C25 C 0.8527(5) 0.9568(5) 0.3155(2) 0.0603(13) Uani 1 1 d . . . H25 H 0.8502 0.9480 0.2689 0.072 Uiso 1 1 calc R . . C26 C 0.8654(4) 0.8588(4) 0.3719(2) 0.0482(11) Uani 1 1 d . . . H26 H 0.8730 0.7844 0.3628 0.058 Uiso 1 1 calc R . . C27 C 0.2814(4) 0.8641(3) 0.90334(19) 0.0352(9) Uani 1 1 d . . . C28 C 0.3887(4) 0.9432(4) 0.8632(2) 0.0467(10) Uani 1 1 d . . . H28 H 0.4809 0.9163 0.8508 0.056 Uiso 1 1 calc R . . C29 C 0.3598(5) 1.0623(4) 0.8413(2) 0.0583(12) Uani 1 1 d . . . H29 H 0.4326 1.1154 0.8147 0.070 Uiso 1 1 calc R . . C30 C 0.2224(5) 1.1022(4) 0.8590(2) 0.0562(12) Uani 1 1 d . . . H30 H 0.2023 1.1821 0.8440 0.067 Uiso 1 1 calc R . . C31 C 0.1156(5) 1.0233(4) 0.8990(2) 0.0523(12) Uani 1 1 d . . . H31 H 0.0235 1.0508 0.9105 0.063 Uiso 1 1 calc R . . C32 C 0.1420(4) 0.9038(4) 0.9224(2) 0.0394(10) Uani 1 1 d . . . C33 C 0.0319(4) 0.8207(4) 0.9680(2) 0.0465(11) Uani 1 1 d . . . H33 H -0.0555 0.8495 0.9876 0.056 Uiso 1 1 calc R . . C34 C 0.0519(4) 0.7060(4) 0.9826(2) 0.0477(11) Uani 1 1 d . . . H34 H -0.0178 0.6559 1.0159 0.057 Uiso 1 1 calc R . . C35 C 0.1862(4) 0.6542(4) 0.9463(2) 0.0373(9) Uani 1 1 d . . . H35 H 0.2027 0.5772 0.9784 0.045 Uiso 1 1 calc R . . C36 C 0.3143(4) 0.7351(3) 0.93513(19) 0.0348(9) Uani 1 1 d . . . C37 C 0.1684(4) 0.6365(3) 0.8721(2) 0.0393(9) Uani 1 1 d . . . C38 C 0.0353(5) 0.6099(4) 0.8625(2) 0.0518(11) Uani 1 1 d . . . H38 H -0.0431 0.6047 0.9011 0.062 Uiso 1 1 calc R . . C39 C 0.0177(5) 0.5912(4) 0.7972(3) 0.0632(13) Uani 1 1 d . . . H39 H -0.0719 0.5739 0.7917 0.076 Uiso 1 1 calc R . . C40 C 0.1338(6) 0.5982(4) 0.7394(3) 0.0651(14) Uani 1 1 d . . . H40 H 0.1227 0.5839 0.6953 0.078 Uiso 1 1 calc R . . C41 C 0.2646(5) 0.6261(4) 0.7471(2) 0.0528(12) Uani 1 1 d . . . H41 H 0.3419 0.6325 0.7077 0.063 Uiso 1 1 calc R . . C42 C 0.2835(4) 0.6451(3) 0.8127(2) 0.0378(9) Uani 1 1 d . . . C43 C 0.4299(4) 0.6771(4) 0.8175(2) 0.0476(11) Uani 1 1 d . . . H43A H 0.4958 0.6160 0.8060 0.057 Uiso 1 1 calc R . . H43B H 0.4599 0.7502 0.7807 0.057 Uiso 1 1 calc R . . C44 C 0.5454(4) 0.6539(4) 0.9240(2) 0.0422(10) Uani 1 1 d . . . C45 C 0.5005(4) 0.6801(3) 0.9970(2) 0.0399(9) Uani 1 1 d . . . C46 C 0.3704(4) 0.7244(3) 1.0057(2) 0.0370(9) Uani 1 1 d . . . C47 C 0.2021(5) 0.6921(5) 1.1273(2) 0.0666(14) Uani 1 1 d . . . H47 H 0.1860 0.6159 1.1247 0.080 Uiso 1 1 calc R . . C48 C 0.1348(6) 0.7302(6) 1.1886(3) 0.091(2) Uani 1 1 d . . . H48 H 0.0716 0.6806 1.2265 0.110 Uiso 1 1 calc R . . C49 C 0.1621(6) 0.8422(7) 1.1933(3) 0.096(2) Uani 1 1 d . . . H49 H 0.1186 0.8674 1.2349 0.115 Uiso 1 1 calc R . . C50 C 0.2515(6) 0.9149(6) 1.1379(4) 0.093(2) Uani 1 1 d . . . H50 H 0.2694 0.9902 1.1414 0.112 Uiso 1 1 calc R . . C51 C 0.3174(5) 0.8783(5) 1.0750(3) 0.0740(16) Uani 1 1 d . . . H51 H 0.3778 0.9294 1.0366 0.089 Uiso 1 1 calc R . . C52 C 0.2927(4) 0.7665(4) 1.0702(2) 0.0437(10) 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 I1 0.03067(16) 0.0846(3) 0.0675(2) -0.02677(18) -0.00157(14) 0.00357(14) I2 0.04642(18) 0.0802(3) 0.0705(2) -0.03143(18) -0.02884(16) 0.01553(15) O1 0.0444(17) 0.057(2) 0.067(2) -0.0146(16) -0.0238(15) 0.0197(15) O2 0.0379(17) 0.076(2) 0.072(2) -0.0362(18) -0.0070(15) 0.0178(15) N1 0.0347(18) 0.043(2) 0.0391(18) -0.0062(16) -0.0133(15) 0.0060(14) N2 0.0313(17) 0.048(2) 0.0370(17) -0.0186(16) -0.0010(14) 0.0049(14) C1 0.034(2) 0.045(3) 0.037(2) -0.0123(19) -0.0010(18) -0.0027(17) C2 0.050(3) 0.062(3) 0.047(2) -0.021(2) -0.004(2) -0.006(2) C3 0.087(4) 0.081(4) 0.055(3) -0.037(3) 0.000(3) -0.016(3) C4 0.091(4) 0.057(4) 0.071(4) -0.033(3) 0.028(3) -0.014(3) C5 0.056(3) 0.045(3) 0.073(3) -0.009(3) 0.028(3) 0.000(2) C6 0.035(2) 0.040(3) 0.052(3) -0.002(2) 0.009(2) -0.0017(18) C7 0.031(2) 0.046(3) 0.071(3) 0.009(2) -0.011(2) 0.0040(19) C8 0.038(2) 0.048(3) 0.052(3) 0.015(2) -0.019(2) -0.0096(19) C9 0.036(2) 0.038(2) 0.0321(19) -0.0047(18) -0.0119(17) 0.0015(17) C10 0.0299(19) 0.036(2) 0.035(2) -0.0049(18) -0.0107(17) 0.0044(16) C11 0.039(2) 0.034(2) 0.0280(18) -0.0081(17) -0.0045(17) 0.0035(17) C12 0.043(2) 0.039(3) 0.038(2) -0.0124(19) -0.0076(18) -0.0020(18) C13 0.045(3) 0.049(3) 0.058(3) -0.015(2) -0.005(2) -0.007(2) C14 0.054(3) 0.052(3) 0.060(3) 0.008(2) 0.004(2) -0.010(2) C15 0.052(3) 0.051(3) 0.047(2) 0.005(2) -0.008(2) 0.007(2) C16 0.039(2) 0.038(3) 0.039(2) -0.0096(19) -0.0064(18) 0.0049(17) C17 0.047(3) 0.050(3) 0.041(2) -0.003(2) -0.018(2) 0.003(2) C18 0.035(2) 0.049(3) 0.050(2) -0.021(2) -0.0169(19) 0.0038(19) C19 0.028(2) 0.044(3) 0.043(2) -0.019(2) -0.0051(17) -0.0003(17) C20 0.031(2) 0.045(3) 0.036(2) -0.0185(19) -0.0078(17) 0.0005(17) C21 0.0263(19) 0.047(3) 0.034(2) -0.0102(19) -0.0039(16) -0.0004(16) C22 0.035(2) 0.049(3) 0.046(2) -0.013(2) -0.0054(19) -0.0033(18) C23 0.042(3) 0.045(3) 0.077(3) -0.012(3) -0.003(2) -0.003(2) C24 0.057(3) 0.066(4) 0.060(3) 0.005(3) -0.013(3) 0.006(2) C25 0.060(3) 0.084(4) 0.032(2) -0.005(3) -0.010(2) -0.002(3) C26 0.048(3) 0.054(3) 0.046(2) -0.018(2) -0.009(2) -0.002(2) C27 0.033(2) 0.046(3) 0.0315(19) -0.0185(19) -0.0085(17) 0.0045(17) C28 0.042(2) 0.049(3) 0.050(2) -0.018(2) -0.006(2) 0.005(2) C29 0.063(3) 0.052(3) 0.058(3) -0.013(2) -0.007(2) -0.003(2) C30 0.072(3) 0.047(3) 0.053(3) -0.018(2) -0.017(3) 0.016(2) C31 0.047(3) 0.066(3) 0.052(3) -0.030(2) -0.015(2) 0.017(2) C32 0.038(2) 0.049(3) 0.038(2) -0.023(2) -0.0112(18) 0.0088(19) C33 0.031(2) 0.071(3) 0.045(2) -0.030(2) -0.0065(19) 0.006(2) C34 0.031(2) 0.065(3) 0.047(2) -0.022(2) 0.0014(19) -0.0032(19) C35 0.032(2) 0.043(3) 0.037(2) -0.0103(18) -0.0051(17) -0.0006(16) C36 0.0278(19) 0.044(3) 0.0339(19) -0.0133(18) -0.0047(16) 0.0050(16) C37 0.043(2) 0.036(2) 0.041(2) -0.0127(19) -0.0096(19) 0.0000(17) C38 0.050(3) 0.054(3) 0.054(3) -0.015(2) -0.015(2) -0.003(2) C39 0.064(3) 0.067(4) 0.072(3) -0.026(3) -0.033(3) -0.001(2) C40 0.084(4) 0.069(4) 0.060(3) -0.034(3) -0.035(3) 0.012(3) C41 0.061(3) 0.056(3) 0.047(2) -0.023(2) -0.015(2) 0.014(2) C42 0.046(2) 0.032(2) 0.036(2) -0.0112(18) -0.0083(18) 0.0095(17) C43 0.044(2) 0.058(3) 0.042(2) -0.023(2) 0.001(2) 0.001(2) C44 0.031(2) 0.044(3) 0.051(2) -0.015(2) -0.0046(19) 0.0014(18) C45 0.035(2) 0.043(3) 0.045(2) -0.015(2) -0.0098(18) -0.0005(17) C46 0.032(2) 0.044(3) 0.036(2) -0.0130(19) -0.0062(17) 0.0003(17) C47 0.078(4) 0.071(4) 0.038(2) -0.002(2) -0.004(2) 0.022(3) C48 0.076(4) 0.137(6) 0.040(3) -0.003(3) -0.002(3) 0.050(4) C49 0.067(4) 0.179(8) 0.064(4) -0.071(5) -0.029(3) 0.062(5) C50 0.058(3) 0.146(6) 0.113(5) -0.099(5) -0.019(3) 0.015(4) C51 0.050(3) 0.096(4) 0.092(4) -0.064(3) 0.000(3) -0.007(3) C52 0.039(2) 0.061(3) 0.038(2) -0.018(2) -0.0181(19) 0.015(2) _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 C19 2.057(4) . ? I2 C45 2.062(4) . ? O1 C18 1.218(4) . ? O2 C44 1.222(4) . ? N1 C10 1.451(4) . ? N1 C17 1.441(5) . ? N1 C18 1.363(5) . ? N2 C36 1.469(4) . ? N2 C43 1.442(4) . ? N2 C44 1.354(5) . ? C1 C2 1.382(5) . ? C1 C6 1.404(5) . ? C1 C10 1.518(5) . ? C2 H2 0.9300 . ? C2 C3 1.387(6) . ? C3 H3 0.9300 . ? C3 C4 1.372(7) . ? C4 H4 0.9300 . ? C4 C5 1.383(7) . ? C5 H5 0.9300 . ? C5 C6 1.387(6) . ? C6 C7 1.454(6) . ? C7 H7 0.9300 . ? C7 C8 1.323(6) . ? C8 H8 0.9300 . ? C8 C9 1.499(5) . ? C9 H9 0.9800 . ? C9 C10 1.551(5) . ? C9 C11 1.522(5) . ? C10 C20 1.543(5) . ? C11 C12 1.402(5) . ? C11 C16 1.387(5) . ? C12 H12 0.9300 . ? C12 C13 1.374(5) . ? C13 H13 0.9300 . ? C13 C14 1.380(6) . ? C14 H14 0.9300 . ? C14 C15 1.379(6) . ? C15 H15 0.9300 . ? C15 C16 1.392(5) . ? C16 C17 1.519(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.485(6) . ? C19 C20 1.325(5) . ? C20 C21 1.479(5) . ? C21 C22 1.387(5) . ? C21 C26 1.390(5) . ? C22 H22 0.9300 . ? C22 C23 1.382(6) . ? C23 H23 0.9300 . ? C23 C24 1.371(6) . ? C24 H24 0.9300 . ? C24 C25 1.382(6) . ? C25 H25 0.9300 . ? C25 C26 1.381(6) . ? C26 H26 0.9300 . ? C27 C28 1.381(5) . ? C27 C32 1.403(5) . ? C27 C36 1.523(5) . ? C28 H28 0.9300 . ? C28 C29 1.383(6) . ? C29 H29 0.9300 . ? C29 C30 1.383(6) . ? C30 H30 0.9300 . ? C30 C31 1.376(6) . ? C31 H31 0.9300 . ? C31 C32 1.385(6) . ? C32 C33 1.451(6) . ? C33 H33 0.9300 . ? C33 C34 1.315(5) . ? C34 H34 0.9300 . ? C34 C35 1.509(5) . ? C35 H35 0.9800 . ? C35 C36 1.538(5) . ? C35 C37 1.535(5) . ? C36 C46 1.535(5) . ? C37 C38 1.394(5) . ? C37 C42 1.394(5) . ? C38 H38 0.9300 . ? C38 C39 1.371(6) . ? C39 H39 0.9300 . ? C39 C40 1.384(6) . ? C40 H40 0.9300 . ? C40 C41 1.364(6) . ? C41 H41 0.9300 . ? C41 C42 1.384(5) . ? C42 C43 1.504(5) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 C45 1.480(5) . ? C45 C46 1.325(5) . ? C46 C52 1.487(5) . ? C47 H47 0.9300 . ? C47 C48 1.385(7) . ? C47 C52 1.377(6) . ? C48 H48 0.9300 . ? C48 C49 1.381(8) . ? C49 H49 0.9300 . ? C49 C50 1.346(9) . ? C50 H50 0.9300 . ? C50 C51 1.396(6) . ? C51 H51 0.9300 . ? C51 C52 1.374(6) . ? 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 C17 N1 C10 120.4(3) . . ? C18 N1 C10 113.7(3) . . ? C18 N1 C17 125.0(3) . . ? C43 N2 C36 121.1(3) . . ? C44 N2 C36 113.8(3) . . ? C44 N2 C43 124.7(3) . . ? C2 C1 C6 119.9(4) . . ? C2 C1 C10 121.2(3) . . ? C6 C1 C10 118.6(3) . . ? C1 C2 H2 119.8 . . ? C1 C2 C3 120.4(4) . . ? C3 C2 H2 119.8 . . ? C2 C3 H3 120.0 . . ? C4 C3 C2 120.1(5) . . ? C4 C3 H3 120.0 . . ? C3 C4 H4 120.1 . . ? C3 C4 C5 119.8(4) . . ? C5 C4 H4 120.1 . . ? C4 C5 H5 119.4 . . ? C4 C5 C6 121.3(5) . . ? C6 C5 H5 119.4 . . ? C1 C6 C7 119.3(4) . . ? C5 C6 C1 118.5(4) . . ? C5 C6 C7 122.2(4) . . ? C6 C7 H7 118.6 . . ? C8 C7 C6 122.8(4) . . ? C8 C7 H7 118.6 . . ? C7 C8 H8 119.2 . . ? C7 C8 C9 121.5(4) . . ? C9 C8 H8 119.2 . . ? C8 C9 H9 107.6 . . ? C8 C9 C10 111.0(3) . . ? C8 C9 C11 110.5(3) . . ? C10 C9 H9 107.6 . . ? C11 C9 H9 107.6 . . ? C11 C9 C10 112.3(3) . . ? N1 C10 C1 112.1(3) . . ? N1 C10 C9 108.2(3) . . ? N1 C10 C20 101.4(3) . . ? C1 C10 C9 113.3(3) . . ? C1 C10 C20 110.7(3) . . ? C20 C10 C9 110.4(3) . . ? C12 C11 C9 119.1(3) . . ? C16 C11 C9 122.4(3) . . ? C16 C11 C12 118.4(4) . . ? C11 C12 H12 119.4 . . ? C13 C12 C11 121.2(4) . . ? C13 C12 H12 119.4 . . ? C12 C13 H13 120.1 . . ? C12 C13 C14 119.7(4) . . ? C14 C13 H13 120.1 . . ? C13 C14 H14 120.0 . . ? C15 C14 C13 120.1(4) . . ? C15 C14 H14 120.0 . . ? C14 C15 H15 119.8 . . ? C14 C15 C16 120.5(4) . . ? C16 C15 H15 119.8 . . ? C11 C16 C15 120.1(4) . . ? C11 C16 C17 121.4(4) . . ? C15 C16 C17 118.5(4) . . ? N1 C17 C16 111.0(3) . . ? N1 C17 H17A 109.4 . . ? N1 C17 H17B 109.4 . . ? C16 C17 H17A 109.4 . . ? C16 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? O1 C18 N1 126.3(4) . . ? O1 C18 C19 129.0(4) . . ? N1 C18 C19 104.7(3) . . ? C18 C19 I1 120.7(2) . . ? C20 C19 I1 127.9(3) . . ? C20 C19 C18 111.5(3) . . ? C19 C20 C10 108.4(3) . . ? C19 C20 C21 127.5(4) . . ? C21 C20 C10 124.0(3) . . ? C22 C21 C20 122.3(3) . . ? C22 C21 C26 118.5(4) . . ? C26 C21 C20 119.2(4) . . ? C21 C22 H22 119.8 . . ? C23 C22 C21 120.5(4) . . ? C23 C22 H22 119.8 . . ? C22 C23 H23 119.7 . . ? C24 C23 C22 120.5(4) . . ? C24 C23 H23 119.7 . . ? C23 C24 H24 120.1 . . ? C23 C24 C25 119.8(5) . . ? C25 C24 H24 120.1 . . ? C24 C25 H25 120.1 . . ? C26 C25 C24 119.9(4) . . ? C26 C25 H25 120.1 . . ? C21 C26 H26 119.6 . . ? C25 C26 C21 120.8(4) . . ? C25 C26 H26 119.6 . . ? C28 C27 C32 120.2(4) . . ? C28 C27 C36 120.9(3) . . ? C32 C27 C36 118.5(4) . . ? C27 C28 H28 119.8 . . ? C27 C28 C29 120.4(4) . . ? C29 C28 H28 119.8 . . ? C28 C29 H29 120.1 . . ? C30 C29 C28 119.8(5) . . ? C30 C29 H29 120.1 . . ? C29 C30 H30 120.1 . . ? C31 C30 C29 119.7(4) . . ? C31 C30 H30 120.1 . . ? C30 C31 H31 119.2 . . ? C30 C31 C32 121.6(4) . . ? C32 C31 H31 119.2 . . ? C27 C32 C33 119.7(4) . . ? C31 C32 C27 118.2(4) . . ? C31 C32 C33 122.1(4) . . ? C32 C33 H33 119.0 . . ? C34 C33 C32 122.1(4) . . ? C34 C33 H33 119.0 . . ? C33 C34 H34 119.5 . . ? C33 C34 C35 121.1(4) . . ? C35 C34 H34 119.5 . . ? C34 C35 H35 108.7 . . ? C34 C35 C36 110.5(3) . . ? C34 C35 C37 109.6(3) . . ? C36 C35 H35 108.7 . . ? C37 C35 H35 108.7 . . ? C37 C35 C36 110.5(3) . . ? N2 C36 C27 113.0(3) . . ? N2 C36 C35 108.2(3) . . ? N2 C36 C46 100.8(3) . . ? C27 C36 C35 111.9(3) . . ? C27 C36 C46 108.9(3) . . ? C46 C36 C35 113.6(3) . . ? C38 C37 C35 120.4(3) . . ? C42 C37 C35 121.6(3) . . ? C42 C37 C38 118.0(4) . . ? C37 C38 H38 119.3 . . ? C39 C38 C37 121.3(4) . . ? C39 C38 H38 119.3 . . ? C38 C39 H39 120.1 . . ? C38 C39 C40 119.8(4) . . ? C40 C39 H39 120.1 . . ? C39 C40 H40 120.1 . . ? C41 C40 C39 119.9(4) . . ? C41 C40 H40 120.1 . . ? C40 C41 H41 119.6 . . ? C40 C41 C42 120.8(4) . . ? C42 C41 H41 119.6 . . ? C37 C42 C43 121.5(3) . . ? C41 C42 C37 120.2(4) . . ? C41 C42 C43 118.2(4) . . ? N2 C43 C42 112.9(3) . . ? N2 C43 H43A 109.0 . . ? N2 C43 H43B 109.0 . . ? C42 C43 H43A 109.0 . . ? C42 C43 H43B 109.0 . . ? H43A C43 H43B 107.8 . . ? O2 C44 N2 126.4(4) . . ? O2 C44 C45 128.6(4) . . ? N2 C44 C45 105.0(3) . . ? C44 C45 I2 121.4(3) . . ? C46 C45 I2 127.3(3) . . ? C46 C45 C44 111.3(3) . . ? C45 C46 C36 109.0(3) . . ? C45 C46 C52 126.6(3) . . ? C52 C46 C36 124.2(3) . . ? C48 C47 H47 119.9 . . ? C52 C47 H47 119.9 . . ? C52 C47 C48 120.3(5) . . ? C47 C48 H48 120.2 . . ? C49 C48 C47 119.7(6) . . ? C49 C48 H48 120.2 . . ? C48 C49 H49 119.9 . . ? C50 C49 C48 120.2(5) . . ? C50 C49 H49 119.9 . . ? C49 C50 H50 119.7 . . ? C49 C50 C51 120.5(6) . . ? C51 C50 H50 119.7 . . ? C50 C51 H51 120.1 . . ? C52 C51 C50 119.8(5) . . ? C52 C51 H51 120.1 . . ? C47 C52 C46 120.5(4) . . ? C51 C52 C46 119.9(4) . . ? C51 C52 C47 119.4(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I1 C19 C20 C10 179.6(2) . . . . ? I1 C19 C20 C21 2.6(6) . . . . ? I2 C45 C46 C36 178.5(3) . . . . ? I2 C45 C46 C52 2.9(7) . . . . ? O1 C18 C19 I1 -2.9(6) . . . . ? O1 C18 C19 C20 176.8(4) . . . . ? O2 C44 C45 I2 3.3(6) . . . . ? O2 C44 C45 C46 -176.9(4) . . . . ? N1 C10 C20 C19 3.2(4) . . . . ? N1 C10 C20 C21 -179.7(3) . . . . ? N1 C18 C19 I1 177.0(2) . . . . ? N1 C18 C19 C20 -3.4(4) . . . . ? N2 C36 C46 C45 -0.8(4) . . . . ? N2 C36 C46 C52 174.8(4) . . . . ? N2 C44 C45 I2 -176.7(3) . . . . ? N2 C44 C45 C46 3.1(5) . . . . ? C1 C2 C3 C4 -0.3(7) . . . . ? C1 C6 C7 C8 10.3(6) . . . . ? C1 C10 C20 C19 122.3(3) . . . . ? C1 C10 C20 C21 -60.5(4) . . . . ? C2 C1 C6 C5 0.4(6) . . . . ? C2 C1 C6 C7 178.5(4) . . . . ? C2 C1 C10 N1 32.5(5) . . . . ? C2 C1 C10 C9 155.3(4) . . . . ? C2 C1 C10 C20 -80.0(5) . . . . ? C2 C3 C4 C5 1.1(8) . . . . ? C3 C4 C5 C6 -1.2(7) . . . . ? C4 C5 C6 C1 0.4(6) . . . . ? C4 C5 C6 C7 -177.6(4) . . . . ? C5 C6 C7 C8 -171.7(4) . . . . ? C6 C1 C2 C3 -0.5(6) . . . . ? C6 C1 C10 N1 -153.8(3) . . . . ? C6 C1 C10 C9 -31.0(5) . . . . ? C6 C1 C10 C20 93.7(4) . . . . ? C6 C7 C8 C9 4.0(6) . . . . ? C7 C8 C9 C10 -30.2(5) . . . . ? C7 C8 C9 C11 95.1(4) . . . . ? C8 C9 C10 N1 166.9(3) . . . . ? C8 C9 C10 C1 41.9(4) . . . . ? C8 C9 C10 C20 -82.9(4) . . . . ? C8 C9 C11 C12 40.4(5) . . . . ? C8 C9 C11 C16 -142.1(4) . . . . ? C9 C10 C20 C19 -111.4(3) . . . . ? C9 C10 C20 C21 65.7(4) . . . . ? C9 C11 C12 C13 177.4(3) . . . . ? C9 C11 C16 C15 -178.3(3) . . . . ? C9 C11 C16 C17 0.7(5) . . . . ? C10 N1 C17 C16 42.6(5) . . . . ? C10 N1 C18 O1 -174.4(4) . . . . ? C10 N1 C18 C19 5.7(4) . . . . ? C10 C1 C2 C3 173.1(4) . . . . ? C10 C1 C6 C5 -173.3(4) . . . . ? C10 C1 C6 C7 4.7(6) . . . . ? C10 C9 C11 C12 165.0(3) . . . . ? C10 C9 C11 C16 -17.5(5) . . . . ? C10 C20 C21 C22 74.4(5) . . . . ? C10 C20 C21 C26 -108.7(4) . . . . ? C11 C9 C10 N1 42.6(4) . . . . ? C11 C9 C10 C1 -82.3(4) . . . . ? C11 C9 C10 C20 152.8(3) . . . . ? C11 C12 C13 C14 0.9(6) . . . . ? C11 C16 C17 N1 -10.5(5) . . . . ? C12 C11 C16 C15 -0.7(5) . . . . ? C12 C11 C16 C17 178.2(3) . . . . ? C12 C13 C14 C15 -0.6(7) . . . . ? C13 C14 C15 C16 -0.3(7) . . . . ? C14 C15 C16 C11 1.0(6) . . . . ? C14 C15 C16 C17 -178.0(4) . . . . ? C15 C16 C17 N1 168.4(3) . . . . ? C16 C11 C12 C13 -0.2(5) . . . . ? C17 N1 C10 C1 66.0(4) . . . . ? C17 N1 C10 C9 -59.6(4) . . . . ? C17 N1 C10 C20 -175.8(3) . . . . ? C17 N1 C18 O1 -4.7(6) . . . . ? C17 N1 C18 C19 175.4(3) . . . . ? C18 N1 C10 C1 -123.7(3) . . . . ? C18 N1 C10 C9 110.6(3) . . . . ? C18 N1 C10 C20 -5.6(4) . . . . ? C18 N1 C17 C16 -126.5(4) . . . . ? C18 C19 C20 C10 0.0(4) . . . . ? C18 C19 C20 C21 -177.1(3) . . . . ? C19 C20 C21 C22 -109.0(4) . . . . ? C19 C20 C21 C26 67.9(5) . . . . ? C20 C21 C22 C23 176.7(3) . . . . ? C20 C21 C26 C25 -177.7(4) . . . . ? C21 C22 C23 C24 0.7(6) . . . . ? C22 C21 C26 C25 -0.7(6) . . . . ? C22 C23 C24 C25 -0.3(7) . . . . ? C23 C24 C25 C26 -0.5(7) . . . . ? C24 C25 C26 C21 1.1(7) . . . . ? C26 C21 C22 C23 -0.1(6) . . . . ? C27 C28 C29 C30 -0.7(6) . . . . ? C27 C32 C33 C34 -11.3(6) . . . . ? C27 C36 C46 C45 -119.9(4) . . . . ? C27 C36 C46 C52 55.8(5) . . . . ? C28 C27 C32 C31 0.9(5) . . . . ? C28 C27 C32 C33 -176.6(3) . . . . ? C28 C27 C36 N2 -32.2(5) . . . . ? C28 C27 C36 C35 -154.6(3) . . . . ? C28 C27 C36 C46 78.9(4) . . . . ? C28 C29 C30 C31 0.6(7) . . . . ? C29 C30 C31 C32 0.2(6) . . . . ? C30 C31 C32 C27 -1.0(6) . . . . ? C30 C31 C32 C33 176.5(4) . . . . ? C31 C32 C33 C34 171.3(4) . . . . ? C32 C27 C28 C29 -0.1(6) . . . . ? C32 C27 C36 N2 154.7(3) . . . . ? C32 C27 C36 C35 32.2(4) . . . . ? C32 C27 C36 C46 -94.2(4) . . . . ? C32 C33 C34 C35 -6.1(6) . . . . ? C33 C34 C35 C36 35.0(5) . . . . ? C33 C34 C35 C37 -87.1(5) . . . . ? C34 C35 C36 N2 -170.9(3) . . . . ? C34 C35 C36 C27 -45.8(4) . . . . ? C34 C35 C36 C46 78.1(4) . . . . ? C34 C35 C37 C38 -31.8(5) . . . . ? C34 C35 C37 C42 148.9(4) . . . . ? C35 C36 C46 C45 114.7(4) . . . . ? C35 C36 C46 C52 -69.7(5) . . . . ? C35 C37 C38 C39 -178.6(4) . . . . ? C35 C37 C42 C41 178.6(4) . . . . ? C35 C37 C42 C43 -2.5(6) . . . . ? C36 N2 C43 C42 -31.8(5) . . . . ? C36 N2 C44 O2 176.3(4) . . . . ? C36 N2 C44 C45 -3.7(4) . . . . ? C36 C27 C28 C29 -173.1(4) . . . . ? C36 C27 C32 C31 174.1(3) . . . . ? C36 C27 C32 C33 -3.4(5) . . . . ? C36 C35 C37 C38 -153.8(4) . . . . ? C36 C35 C37 C42 26.9(5) . . . . ? C36 C46 C52 C47 91.2(5) . . . . ? C36 C46 C52 C51 -92.5(5) . . . . ? C37 C35 C36 N2 -49.4(4) . . . . ? C37 C35 C36 C27 75.7(4) . . . . ? C37 C35 C36 C46 -160.4(3) . . . . ? C37 C38 C39 C40 0.3(7) . . . . ? C37 C42 C43 N2 2.8(5) . . . . ? C38 C37 C42 C41 -0.8(6) . . . . ? C38 C37 C42 C43 178.1(4) . . . . ? C38 C39 C40 C41 -1.4(7) . . . . ? C39 C40 C41 C42 1.4(7) . . . . ? C40 C41 C42 C37 -0.3(6) . . . . ? C40 C41 C42 C43 -179.2(4) . . . . ? C41 C42 C43 N2 -178.3(4) . . . . ? C42 C37 C38 C39 0.8(6) . . . . ? C43 N2 C36 C27 -68.2(4) . . . . ? C43 N2 C36 C35 56.3(5) . . . . ? C43 N2 C36 C46 175.7(3) . . . . ? C43 N2 C44 O2 3.8(7) . . . . ? C43 N2 C44 C45 -176.2(4) . . . . ? C44 N2 C36 C27 119.0(4) . . . . ? C44 N2 C36 C35 -116.5(4) . . . . ? C44 N2 C36 C46 3.0(4) . . . . ? C44 N2 C43 C42 140.2(4) . . . . ? C44 C45 C46 C36 -1.3(5) . . . . ? C44 C45 C46 C52 -176.9(4) . . . . ? C45 C46 C52 C47 -93.9(5) . . . . ? C45 C46 C52 C51 82.4(6) . . . . ? C47 C48 C49 C50 1.3(8) . . . . ? C48 C47 C52 C46 177.2(4) . . . . ? C48 C47 C52 C51 0.9(7) . . . . ? C48 C49 C50 C51 0.1(9) . . . . ? C49 C50 C51 C52 -1.0(8) . . . . ? C50 C51 C52 C46 -175.8(4) . . . . ? C50 C51 C52 C47 0.5(7) . . . . ? C52 C47 C48 C49 -1.8(8) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 928528' ####################################################################### # # 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_wanglj_0117 #TrackingRef 'wanglj_0117.cif' _audit_creation_date 2013-03-01 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H16 I N O' _chemical_formula_sum 'C22 H16 I N O' _chemical_formula_weight 437.26 _chemical_melting_point ? 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' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _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' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' _cell_length_a 10.5172(8) _cell_length_b 17.5717(6) _cell_length_c 20.0963(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3713.9(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2440 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.8110 _cell_measurement_theta_min 3.6260 _exptl_absorpt_coefficient_mu 1.733 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.69184 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1728 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.25 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_unetI/netI 0.0624 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 13199 _diffrn_reflns_theta_full 28.55 _diffrn_reflns_theta_max 28.55 _diffrn_reflns_theta_min 3.03 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.9970 _diffrn_measured_fraction_theta_max 0.9080 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 8.00 77.00 1.5000 12.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 57.0000 -30.0000 46 #__ type_ start__ end____ width___ exp.time_ 2 omega -51.00 6.00 1.5000 12.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 -38.0000 0.0000 38 #__ type_ start__ end____ width___ exp.time_ 3 omega 10.00 41.50 1.5000 12.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 -99.0000 -30.0000 21 #__ type_ start__ end____ width___ exp.time_ 4 omega 38.00 98.00 1.5000 12.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 -178.0000 -90.0000 40 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0214669000 _diffrn_orient_matrix_UB_12 -0.0104219000 _diffrn_orient_matrix_UB_13 0.0321938000 _diffrn_orient_matrix_UB_21 -0.0090184000 _diffrn_orient_matrix_UB_22 0.0379438000 _diffrn_orient_matrix_UB_23 0.0110904000 _diffrn_orient_matrix_UB_31 -0.0632917000 _diffrn_orient_matrix_UB_32 -0.0089314000 _diffrn_orient_matrix_UB_33 0.0093158000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2224 _reflns_number_total 4308 _reflns_odcompleteness_completeness 99.70 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _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 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 1.391 _refine_diff_density_min -0.623 _refine_diff_density_rms 0.087 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 4308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1465 _refine_ls_R_factor_gt 0.0741 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0254P)^2^+14.9618P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1273 _refine_ls_wR_factor_ref 0.1546 _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: H22 of C22, H21 of C21, H20 of C20, H19 of C19, H18 of C18, H5 of C5, H6 of C6, H7 of C7, H8 of C8, H11 of C11, H12 of C12, H13 of C13, H14 of C14, H15 of C15, {H16A,H16B} of C16 2.a Secondary CH2 refined with riding coordinates: C16(H16A,H16B) 2.b Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _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 0.56830(6) 0.61350(3) 0.37707(3) 0.0772(2) Uani 1 1 d . . . O1 O 0.8216(5) 0.5241(3) 0.3497(3) 0.0749(17) Uani 1 1 d . . . N1 N 0.7577(6) 0.4023(3) 0.3355(3) 0.0503(15) Uani 1 1 d . . . C1 C 0.7329(8) 0.4782(4) 0.3477(4) 0.0554(19) Uani 1 1 d . . . C2 C 0.6014(7) 0.4979(4) 0.3587(4) 0.0503(18) Uani 1 1 d . . . C3 C 0.5053(6) 0.4469(4) 0.3584(3) 0.0434(16) Uani 1 1 d . . . C4 C 0.5356(7) 0.3680(4) 0.3442(3) 0.0471(18) Uani 1 1 d . . . C5 C 0.4394(7) 0.3121(4) 0.3403(3) 0.0511(18) Uani 1 1 d . . . H5 H 0.3556 0.3261 0.3483 0.061 Uiso 1 1 calc R . . C6 C 0.4659(9) 0.2387(5) 0.3253(4) 0.066(2) Uani 1 1 d . . . H6 H 0.4014 0.2028 0.3219 0.079 Uiso 1 1 calc R . . C7 C 0.5944(9) 0.2181(5) 0.3149(4) 0.070(2) Uani 1 1 d . . . H7 H 0.6143 0.1677 0.3057 0.084 Uiso 1 1 calc R . . C8 C 0.6897(8) 0.2705(4) 0.3182(4) 0.060(2) Uani 1 1 d . . . H8 H 0.7734 0.2555 0.3112 0.072 Uiso 1 1 calc R . . C9 C 0.6619(7) 0.3472(4) 0.3323(3) 0.0479(17) Uani 1 1 d . . . C10 C 0.3718(7) 0.4689(4) 0.3729(4) 0.0536(18) Uani 1 1 d . . . C11 C 0.2964(8) 0.5030(4) 0.3259(5) 0.070(2) Uani 1 1 d . . . H11 H 0.3286 0.5119 0.2835 0.084 Uiso 1 1 calc R . . C12 C 0.1737(10) 0.5241(6) 0.3407(7) 0.096(3) Uani 1 1 d . . . H12 H 0.1235 0.5474 0.3085 0.115 Uiso 1 1 calc R . . C13 C 0.1250(11) 0.5105(7) 0.4041(8) 0.107(4) Uani 1 1 d . . . H13 H 0.0418 0.5239 0.4144 0.128 Uiso 1 1 calc R . . C14 C 0.1997(12) 0.4778(6) 0.4500(6) 0.101(4) Uani 1 1 d . . . H14 H 0.1673 0.4695 0.4925 0.121 Uiso 1 1 calc R . . C15 C 0.3232(9) 0.4560(5) 0.4362(4) 0.070(2) Uani 1 1 d . . . H15 H 0.3730 0.4331 0.4688 0.084 Uiso 1 1 calc R . . C16 C 0.8903(7) 0.3794(5) 0.3248(4) 0.060(2) Uani 1 1 d . . . H16A H 0.9396 0.4242 0.3133 0.072 Uiso 1 1 calc R . . H16B H 0.8936 0.3448 0.2872 0.072 Uiso 1 1 calc R . . C17 C 0.9513(6) 0.3413(4) 0.3840(4) 0.0490(17) Uani 1 1 d . . . C18 C 1.0612(7) 0.3009(4) 0.3754(4) 0.061(2) Uani 1 1 d . . . H18 H 1.0948 0.2953 0.3329 0.073 Uiso 1 1 calc R . . C19 C 1.1235(9) 0.2679(5) 0.4292(5) 0.078(3) Uani 1 1 d . . . H19 H 1.1974 0.2399 0.4225 0.094 Uiso 1 1 calc R . . C20 C 1.0758(9) 0.2768(5) 0.4919(5) 0.085(3) Uani 1 1 d . . . H20 H 1.1178 0.2555 0.5281 0.101 Uiso 1 1 calc R . . C21 C 0.9668(10) 0.3169(5) 0.5012(5) 0.083(3) Uani 1 1 d . . . H21 H 0.9341 0.3227 0.5439 0.099 Uiso 1 1 calc R . . C22 C 0.9040(8) 0.3490(5) 0.4478(4) 0.066(2) Uani 1 1 d . . . H22 H 0.8291 0.3760 0.4548 0.080 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 0.0831(4) 0.0427(3) 0.1059(5) -0.0032(3) -0.0009(4) -0.0010(3) O1 0.053(4) 0.063(3) 0.109(5) 0.005(3) -0.002(3) -0.012(3) N1 0.052(4) 0.044(4) 0.055(4) 0.003(3) -0.001(3) 0.006(3) C1 0.054(5) 0.053(5) 0.059(5) 0.008(4) 0.003(4) -0.007(4) C2 0.051(5) 0.039(4) 0.061(5) 0.004(3) -0.002(4) 0.003(3) C3 0.041(4) 0.043(4) 0.046(4) 0.006(3) -0.002(3) 0.003(3) C4 0.057(5) 0.041(4) 0.043(4) 0.005(3) -0.004(3) -0.001(3) C5 0.051(5) 0.054(4) 0.049(4) 0.005(3) -0.006(4) -0.005(4) C6 0.082(7) 0.049(5) 0.067(5) 0.006(4) -0.013(5) -0.015(4) C7 0.102(8) 0.046(5) 0.063(5) -0.005(4) -0.015(5) 0.009(5) C8 0.062(5) 0.053(5) 0.065(5) -0.008(4) -0.008(4) 0.014(4) C9 0.062(5) 0.045(4) 0.037(4) 0.003(3) -0.005(4) 0.003(4) C10 0.050(4) 0.045(4) 0.066(5) -0.005(4) -0.005(4) -0.001(3) C11 0.068(6) 0.052(5) 0.090(6) -0.005(4) -0.021(5) 0.016(4) C12 0.061(7) 0.080(7) 0.147(11) -0.021(7) -0.040(7) 0.017(5) C13 0.050(7) 0.095(9) 0.175(13) -0.059(9) 0.012(8) -0.004(6) C14 0.084(9) 0.105(9) 0.113(9) -0.043(7) 0.033(7) -0.021(7) C15 0.066(6) 0.070(6) 0.074(6) -0.008(5) 0.009(5) 0.005(5) C16 0.056(5) 0.069(5) 0.056(5) 0.001(4) 0.010(4) 0.003(4) C17 0.046(4) 0.046(4) 0.056(5) -0.009(3) 0.000(4) -0.004(3) C18 0.048(5) 0.054(4) 0.080(5) -0.003(4) 0.008(5) 0.003(4) C19 0.058(6) 0.073(6) 0.104(8) 0.016(6) -0.008(6) 0.020(5) C20 0.082(7) 0.083(7) 0.089(7) 0.018(6) -0.017(6) 0.014(6) C21 0.096(8) 0.089(7) 0.063(6) 0.013(5) -0.001(5) 0.014(6) C22 0.063(6) 0.073(6) 0.062(5) 0.004(4) 0.002(4) 0.012(4) _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 2.094(7) . ? O1 C1 1.234(8) . ? N1 C1 1.380(9) . ? N1 C9 1.400(9) . ? N1 C16 1.467(9) . ? C1 C2 1.443(10) . ? C2 C3 1.351(9) . ? C3 C4 1.451(9) . ? C3 C10 1.485(10) . ? C4 C5 1.412(9) . ? C4 C9 1.398(10) . ? C5 H5 0.9300 . ? C5 C6 1.354(10) . ? C6 H6 0.9300 . ? C6 C7 1.414(11) . ? C7 H7 0.9300 . ? C7 C8 1.362(11) . ? C8 H8 0.9300 . ? C8 C9 1.407(9) . ? C10 C11 1.372(10) . ? C10 C15 1.389(11) . ? C11 H11 0.9300 . ? C11 C12 1.375(12) . ? C12 H12 0.9300 . ? C12 C13 1.394(15) . ? C13 H13 0.9300 . ? C13 C14 1.342(15) . ? C14 H14 0.9300 . ? C14 C15 1.383(13) . ? C15 H15 0.9300 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 C17 1.509(10) . ? C17 C18 1.368(9) . ? C17 C22 1.381(10) . ? C18 H18 0.9300 . ? C18 C19 1.390(11) . ? C19 H19 0.9300 . ? C19 C20 1.366(12) . ? C20 H20 0.9300 . ? C20 C21 1.359(12) . ? C21 H21 0.9300 . ? C21 C22 1.382(11) . ? C22 H22 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 C1 N1 C9 122.7(6) . . ? C1 N1 C16 118.1(6) . . ? C9 N1 C16 119.2(6) . . ? O1 C1 N1 119.6(7) . . ? O1 C1 C2 124.2(7) . . ? N1 C1 C2 116.1(6) . . ? C1 C2 I1 114.8(5) . . ? C3 C2 I1 121.3(5) . . ? C3 C2 C1 123.9(6) . . ? C2 C3 C4 118.1(6) . . ? C2 C3 C10 122.3(6) . . ? C4 C3 C10 119.7(6) . . ? C5 C4 C3 121.2(7) . . ? C9 C4 C3 119.5(6) . . ? C9 C4 C5 119.3(7) . . ? C4 C5 H5 119.1 . . ? C6 C5 C4 121.9(7) . . ? C6 C5 H5 119.1 . . ? C5 C6 H6 120.9 . . ? C5 C6 C7 118.2(7) . . ? C7 C6 H6 120.9 . . ? C6 C7 H7 119.2 . . ? C8 C7 C6 121.5(8) . . ? C8 C7 H7 119.2 . . ? C7 C8 H8 119.9 . . ? C7 C8 C9 120.3(8) . . ? C9 C8 H8 119.9 . . ? N1 C9 C8 121.5(7) . . ? C4 C9 N1 119.7(6) . . ? C4 C9 C8 118.8(7) . . ? C11 C10 C3 121.7(8) . . ? C11 C10 C15 119.3(8) . . ? C15 C10 C3 119.0(7) . . ? C10 C11 H11 119.6 . . ? C10 C11 C12 120.7(10) . . ? C12 C11 H11 119.6 . . ? C11 C12 H12 120.1 . . ? C11 C12 C13 119.7(10) . . ? C13 C12 H12 120.1 . . ? C12 C13 H13 120.4 . . ? C14 C13 C12 119.2(11) . . ? C14 C13 H13 120.4 . . ? C13 C14 H14 119.0 . . ? C13 C14 C15 122.0(11) . . ? C15 C14 H14 119.0 . . ? C10 C15 H15 120.5 . . ? C14 C15 C10 119.0(9) . . ? C14 C15 H15 120.5 . . ? N1 C16 H16A 108.7 . . ? N1 C16 H16B 108.7 . . ? N1 C16 C17 114.2(6) . . ? H16A C16 H16B 107.6 . . ? C17 C16 H16A 108.7 . . ? C17 C16 H16B 108.7 . . ? C18 C17 C16 119.3(7) . . ? C18 C17 C22 118.3(8) . . ? C22 C17 C16 122.3(7) . . ? C17 C18 H18 119.5 . . ? C17 C18 C19 121.0(8) . . ? C19 C18 H18 119.5 . . ? C18 C19 H19 120.1 . . ? C20 C19 C18 119.8(8) . . ? C20 C19 H19 120.1 . . ? C19 C20 H20 120.1 . . ? C21 C20 C19 119.8(9) . . ? C21 C20 H20 120.1 . . ? C20 C21 H21 119.7 . . ? C20 C21 C22 120.5(9) . . ? C22 C21 H21 119.7 . . ? C17 C22 C21 120.6(8) . . ? C17 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? 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 I1 C2 C3 C4 179.0(5) . . . . ? I1 C2 C3 C10 -1.8(10) . . . . ? O1 C1 C2 I1 1.1(10) . . . . ? O1 C1 C2 C3 -177.9(8) . . . . ? N1 C1 C2 I1 180.0(5) . . . . ? N1 C1 C2 C3 1.0(11) . . . . ? N1 C16 C17 C18 163.7(7) . . . . ? N1 C16 C17 C22 -19.8(10) . . . . ? C1 N1 C9 C4 -2.4(10) . . . . ? C1 N1 C9 C8 178.6(7) . . . . ? C1 N1 C16 C17 102.6(8) . . . . ? C1 C2 C3 C4 -2.0(11) . . . . ? C1 C2 C3 C10 177.2(7) . . . . ? C2 C3 C4 C5 -177.3(7) . . . . ? C2 C3 C4 C9 0.9(10) . . . . ? C2 C3 C10 C11 79.2(9) . . . . ? C2 C3 C10 C15 -99.4(9) . . . . ? C3 C4 C5 C6 178.2(7) . . . . ? C3 C4 C9 N1 1.2(10) . . . . ? C3 C4 C9 C8 -179.7(6) . . . . ? C3 C10 C11 C12 -178.8(7) . . . . ? C3 C10 C15 C14 178.8(7) . . . . ? C4 C3 C10 C11 -101.6(8) . . . . ? C4 C3 C10 C15 79.8(9) . . . . ? C4 C5 C6 C7 1.5(11) . . . . ? C5 C4 C9 N1 179.5(6) . . . . ? C5 C4 C9 C8 -1.5(10) . . . . ? C5 C6 C7 C8 -1.6(12) . . . . ? C6 C7 C8 C9 0.0(12) . . . . ? C7 C8 C9 N1 -179.5(7) . . . . ? C7 C8 C9 C4 1.5(11) . . . . ? C9 N1 C1 O1 -179.7(7) . . . . ? C9 N1 C1 C2 1.3(10) . . . . ? C9 N1 C16 C17 -78.1(8) . . . . ? C9 C4 C5 C6 -0.1(11) . . . . ? C10 C3 C4 C5 3.4(10) . . . . ? C10 C3 C4 C9 -178.3(6) . . . . ? C10 C11 C12 C13 -0.3(14) . . . . ? C11 C10 C15 C14 0.2(12) . . . . ? C11 C12 C13 C14 0.9(16) . . . . ? C12 C13 C14 C15 -1.0(17) . . . . ? C13 C14 C15 C10 0.5(15) . . . . ? C15 C10 C11 C12 -0.3(12) . . . . ? C16 N1 C1 O1 -0.4(10) . . . . ? C16 N1 C1 C2 -179.3(6) . . . . ? C16 N1 C9 C4 178.2(6) . . . . ? C16 N1 C9 C8 -0.8(10) . . . . ? C16 C17 C18 C19 177.0(7) . . . . ? C16 C17 C22 C21 -176.2(8) . . . . ? C17 C18 C19 C20 -1.0(13) . . . . ? C18 C17 C22 C21 0.3(12) . . . . ? C18 C19 C20 C21 0.9(15) . . . . ? C19 C20 C21 C22 -0.3(16) . . . . ? C20 C21 C22 C17 -0.4(14) . . . . ? C22 C17 C18 C19 0.4(11) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 928529'