# Electronic Supplementary Material (ESI) for Chemical Communications # 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_1_7_4 _audit_creation_date 2013-04-18T11:23:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_melting_point ? _chemical_formula_moiety 'C64 H96 N4 O8, 5.5 (C Br Cl3), 4.75 (Br), 2.5(O)' _chemical_formula_sum 'C69.50 H96 Br10.25 Cl16.50 N4 O10.50' _chemical_formula_weight 2559.5 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' _space_group_IT_number 14 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.7068(4) _cell_length_b 31.1489(9) _cell_length_c 18.8860(5) _cell_angle_alpha 90 _cell_angle_beta 90.783(2) _cell_angle_gamma 90 _cell_volume 10415.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123.0(1) _cell_measurement_reflns_used 19653 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.283 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.632 _exptl_crystal_F_000 5057 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.415 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Sheldrick, G. M. SADABS 2008/2; University of G\"ottingen: G\"ottingen, Germany, 2008. ; _exptl_absorpt_correction_T_min 0.4531 _exptl_absorpt_correction_T_max 0.7457 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123.0(1) _diffrn_source 'Enraf Nonius FR590' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Bruker-Nonius Kappa Apex II Diffractometer' _diffrn_measurement_method '\w and \f scans' _diffrn_reflns_av_unetI/netI 0.0883 _diffrn_reflns_av_R_equivalents 0.0755 _diffrn_reflns_number 76288 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.323 _diffrn_reflns_theta_max 25.498 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_full 0.954 _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_Laue_measured_fraction_full 0.954 _diffrn_reflns_Laue_measured_fraction_max 0.952 _diffrn_reflns_point_group_measured_fraction_full 0.954 _diffrn_reflns_point_group_measured_fraction_max 0.952 _reflns_number_total 18449 _reflns_number_gt 10680 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'MERCURY (Macrae et al., 2006)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.1959P)^2^+108.2777P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 18449 _refine_ls_number_parameters 1097 _refine_ls_number_restraints 90 _refine_ls_R_factor_all 0.1835 _refine_ls_R_factor_gt 0.1163 _refine_ls_wR_factor_ref 0.3863 _refine_ls_wR_factor_gt 0.3326 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.178 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 4.171 _refine_diff_density_min -2.307 _refine_diff_density_rms 0.243 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group N30 N 0.2732(7) 0.2588(3) -0.0764(5) 0.032(3) Uani 1 d . . H30A H 0.2186 0.2654 -0.0732 0.039 Uiso 1 calc . . H30B H 0.292 0.2527 -0.0278 0.039 Uiso 1 calc . . N32 N 0.4318(6) 0.2643(3) 0.2266(6) 0.028(2) Uani 1 d . . H32A H 0.3803 0.2549 0.2395 0.033 Uiso 1 calc . . H32B H 0.4313 0.2708 0.1753 0.033 Uiso 1 calc . . N34 N 0.0908(6) 0.2664(3) 0.3531(5) 0.031(2) Uani 1 d . . H34A H 0.1455 0.2726 0.3501 0.037 Uiso 1 calc . . H34B H 0.072 0.2602 0.3046 0.037 Uiso 1 calc . . N36 N -0.0689(6) 0.2657(3) 0.0557(6) 0.031(2) Uani 1 d . . H36A H -0.0703 0.2729 0.1068 0.037 Uiso 1 calc . . H36B H -0.0169 0.2562 0.0449 0.037 Uiso 1 calc . . O4 O 0.4163(5) 0.3396(3) -0.0010(5) 0.032(2) Uani 1 d . . H4 H 0.4143 0.3131 0.0071 0.047 Uiso 1 calc . . O6 O 0.1782(5) 0.3334(3) -0.1175(5) 0.034(2) Uani 1 d . . H6 H 0.1329 0.3351 -0.1053 0.051 Uiso 1 calc . . O11 O 0.3340(5) 0.3431(3) 0.3562(4) 0.032(2) Uani 1 d . . H11 H 0.3523 0.3182 0.3589 0.047 Uiso 1 calc . . O13 O 0.4620(5) 0.3389(3) 0.1374(4) 0.0283(19) Uani 1 d . . H13 H 0.4498 0.3406 0.0944 0.042 Uiso 1 calc . . O18 O -0.0501(5) 0.3467(3) 0.2764(5) 0.033(2) Uani 1 d . . H18 H -0.0482 0.3198 0.2727 0.05 Uiso 1 calc . . O20 O 0.1888(5) 0.3411(3) 0.3945(4) 0.033(2) Uani 1 d . . H20 H 0.2347 0.3446 0.3851 0.049 Uiso 1 calc . . O25 O 0.0308(5) 0.3390(3) -0.0789(4) 0.032(2) Uani 1 d . . H25 H 0.0302 0.3121 -0.0754 0.048 Uiso 1 calc . . O27 O -0.0982(5) 0.3436(3) 0.1386(5) 0.032(2) Uani 1 d . . H27 H -0.0908 0.3496 0.1815 0.048 Uiso 1 calc . . C1 C 0.2005(7) 0.3919(4) -0.0321(6) 0.029(3) Uani 1 d . . C2 C 0.2523(7) 0.4094(4) 0.0149(6) 0.026(3) Uani 1 d . . H2 H 0.2384 0.4345 0.0403 0.031 Uiso 1 calc . . C3 C 0.3247(7) 0.3921(4) 0.0270(6) 0.027(3) Uani 1 d . . C4 C 0.3440(7) 0.3553(4) -0.0116(7) 0.029(3) Uani 1 d . . C5 C 0.2948(7) 0.3367(4) -0.0592(6) 0.028(3) Uani 1 d . . C6 C 0.2233(7) 0.3547(4) -0.0688(7) 0.025(3) Uani 1 d . . C7 C 0.3794(7) 0.4130(4) 0.0789(6) 0.026(3) Uani 1 d . . H7 H 0.4313 0.4043 0.0644 0.032 Uiso 1 calc . . C8 C 0.3678(7) 0.3952(4) 0.1534(6) 0.027(3) Uani 1 d . . C9 C 0.3170(7) 0.4118(4) 0.2002(6) 0.027(3) Uani 1 d . . H9 H 0.2881 0.4361 0.1856 0.032 Uiso 1 calc . . C10 C 0.3050(7) 0.3954(4) 0.2679(7) 0.034(3) Uani 1 d . . C11 C 0.3463(7) 0.3599(4) 0.2878(7) 0.029(3) Uani 1 d . . C12 C 0.3996(7) 0.3417(4) 0.2434(7) 0.029(3) Uani 1 d . . C13 C 0.4090(7) 0.3590(4) 0.1771(6) 0.023(3) Uani 1 d . . C14 C 0.2473(7) 0.4163(4) 0.3168(6) 0.028(3) Uani 1 d . . H14 H 0.2636 0.4087 0.3661 0.034 Uiso 1 calc . . C15 C 0.1677(7) 0.3973(4) 0.3070(7) 0.030(3) Uani 1 d . . C16 C 0.1151(7) 0.4151(4) 0.2585(6) 0.028(3) Uani 1 d . . H16 H 0.1296 0.4397 0.2324 0.033 Uiso 1 calc . . C17 C 0.0425(7) 0.3982(4) 0.2468(7) 0.029(3) Uani 1 d . . C18 C 0.0232(8) 0.3630(4) 0.2868(7) 0.032(3) Uani 1 d . . C19 C 0.0717(7) 0.3444(4) 0.3341(7) 0.027(3) Uani 1 d . . C20 C 0.1437(7) 0.3619(4) 0.3427(6) 0.027(3) Uani 1 d . . C21 C -0.0085(7) 0.4179(4) 0.1921(7) 0.028(3) Uani 1 d . . H21 H -0.0612 0.4116 0.2076 0.034 Uiso 1 calc . . C22 C 0.0000(7) 0.3958(4) 0.1185(7) 0.029(3) Uani 1 d . . C23 C 0.0535(7) 0.4116(4) 0.0714(7) 0.031(3) Uani 1 d . . H23 H 0.0831 0.4358 0.0847 0.038 Uiso 1 calc . . C24 C 0.0644(7) 0.3931(4) 0.0059(6) 0.026(3) Uani 1 d . . C25 C 0.0213(7) 0.3574(4) -0.0120(6) 0.026(3) Uani 1 d . . C26 C -0.0340(7) 0.3411(4) 0.0333(7) 0.032(3) Uani 1 d . . C27 C -0.0434(7) 0.3617(4) 0.0993(7) 0.027(3) Uani 1 d . . C28 C 0.1243(7) 0.4099(4) -0.0457(6) 0.029(3) Uani 1 d . . H28 H 0.1085 0.4001 -0.094 0.035 Uiso 1 calc . . C29 C 0.3135(7) 0.2983(4) -0.1038(7) 0.029(3) Uani 1 d . . H29A H 0.3687 0.2934 -0.1026 0.035 Uiso 1 calc . . H29B H 0.2978 0.3037 -0.1535 0.035 Uiso 1 calc . . C31 C 0.4512(8) 0.3052(4) 0.2675(7) 0.030(3) Uani 1 d . . H31A H 0.4451 0.3002 0.3189 0.037 Uiso 1 calc . . H31B H 0.5045 0.3131 0.2592 0.037 Uiso 1 calc . . C33 C 0.0519(8) 0.3054(4) 0.3796(7) 0.032(3) Uani 1 d . . H33A H 0.0674 0.3108 0.4293 0.038 Uiso 1 calc . . H33B H -0.0034 0.3007 0.3782 0.038 Uiso 1 calc . . C35 C -0.0862(7) 0.3048(4) 0.0142(7) 0.034(3) Uani 1 d . . H35A H -0.139 0.3137 0.0228 0.04 Uiso 1 calc . . H35B H -0.0816 0.2984 -0.0369 0.04 Uiso 1 calc . . C37 C 0.2826(8) 0.2185(4) -0.1211(7) 0.031(3) Uani 1 d . . H37 H 0.3372 0.2146 -0.1322 0.038 Uiso 1 calc . . C38 C 0.2556(9) 0.1809(4) -0.0768(8) 0.041(3) Uani 1 d . . H38A H 0.2024 0.1854 -0.0632 0.049 Uiso 1 calc . . H38B H 0.2867 0.1787 -0.033 0.049 Uiso 1 calc . . C39 C 0.2626(11) 0.1394(5) -0.1203(9) 0.057(4) Uani 1 d . . H39A H 0.2429 0.1149 -0.0927 0.068 Uiso 1 calc . . H39B H 0.3164 0.1338 -0.1303 0.068 Uiso 1 calc . . C40 C 0.2186(11) 0.1434(5) -0.1893(10) 0.064(5) Uani 1 d . . H40A H 0.2249 0.1167 -0.2171 0.077 Uiso 1 calc . . H40B H 0.1642 0.1466 -0.179 0.077 Uiso 1 calc . . C41 C 0.2447(9) 0.1818(5) -0.2334(8) 0.049(4) Uani 1 d . . H41A H 0.2134 0.184 -0.2771 0.059 Uiso 1 calc . . H41B H 0.298 0.1777 -0.2472 0.059 Uiso 1 calc . . C42 C 0.2373(8) 0.2228(4) -0.1898(7) 0.038(3) Uani 1 d . . H42A H 0.1835 0.2281 -0.1792 0.046 Uiso 1 calc . . H42B H 0.2562 0.2476 -0.2173 0.046 Uiso 1 calc . . C43 C 0.4853(8) 0.2285(4) 0.2406(7) 0.036(3) Uani 1 d . . H43 H 0.4938 0.2257 0.2928 0.043 Uiso 1 calc . . C44 C 0.5612(8) 0.2368(4) 0.2050(8) 0.037(3) Uani 1 d . . H44A H 0.5828 0.2642 0.2224 0.045 Uiso 1 calc . . H44B H 0.5535 0.2391 0.1531 0.045 Uiso 1 calc . . C45 C 0.6157(8) 0.2000(5) 0.2218(8) 0.047(4) Uani 1 d . . H45A H 0.6245 0.1982 0.2736 0.057 Uiso 1 calc . . H45B H 0.6648 0.2053 0.199 0.057 Uiso 1 calc . . C46 C 0.5813(10) 0.1568(5) 0.1941(9) 0.057(5) Uani 1 d . . H46A H 0.576 0.158 0.1418 0.068 Uiso 1 calc . . H46B H 0.6159 0.1329 0.2062 0.068 Uiso 1 calc . . C47 C 0.5073(10) 0.1487(5) 0.2250(9) 0.052(4) Uani 1 d . . H47A H 0.5137 0.1444 0.2767 0.063 Uiso 1 calc . . H47B H 0.4861 0.122 0.2046 0.063 Uiso 1 calc . . C48 C 0.4508(9) 0.1862(4) 0.2116(8) 0.044(4) Uani 1 d . . H48A H 0.4026 0.1802 0.2355 0.052 Uiso 1 calc . . H48B H 0.4402 0.1891 0.1602 0.052 Uiso 1 calc . . C49 C 0.0802(7) 0.2259(4) 0.3989(6) 0.028(3) Uani 1 d . . H49 H 0.0252 0.223 0.4094 0.034 Uiso 1 calc . . C50 C 0.1037(8) 0.1878(4) 0.3566(8) 0.039(3) Uani 1 d . . H50A H 0.157 0.1911 0.3423 0.047 Uiso 1 calc . . H50B H 0.0721 0.1858 0.3131 0.047 Uiso 1 calc . . C51 C 0.0951(9) 0.1467(4) 0.4004(8) 0.043(4) Uani 1 d . . H51A H 0.1135 0.1218 0.3729 0.052 Uiso 1 calc . . H51B H 0.041 0.1419 0.4106 0.052 Uiso 1 calc . . C52 C 0.1405(11) 0.1503(5) 0.4709(9) 0.058(5) Uani 1 d . . H52A H 0.1327 0.1241 0.4995 0.069 Uiso 1 calc . . H52B H 0.1951 0.1526 0.4607 0.069 Uiso 1 calc . . C53 C 0.1151(8) 0.1897(5) 0.5126(7) 0.040(3) Uani 1 d . . H53A H 0.1461 0.1923 0.5565 0.047 Uiso 1 calc . . H53B H 0.0618 0.186 0.5265 0.047 Uiso 1 calc . . C54 C 0.1227(8) 0.2311(5) 0.4687(8) 0.041(3) Uani 1 d . . H54A H 0.1018 0.2557 0.4952 0.049 Uiso 1 calc . . H54B H 0.1767 0.237 0.4596 0.049 Uiso 1 calc . . C55 C -0.1237(8) 0.2282(4) 0.0411(7) 0.033(3) Uani 1 d . . H55 H -0.1306 0.225 -0.0113 0.04 Uiso 1 calc . . C56 C -0.0880(9) 0.1876(4) 0.0702(9) 0.043(4) Uani 1 d . . H56A H -0.0758 0.1915 0.1211 0.052 Uiso 1 calc . . H56B H -0.0402 0.1818 0.0452 0.052 Uiso 1 calc . . C57 C -0.1416(9) 0.1493(5) 0.0608(9) 0.052(4) Uani 1 d . . H57A H -0.1488 0.1432 0.0097 0.062 Uiso 1 calc . . H57B H -0.1192 0.1236 0.0836 0.062 Uiso 1 calc . . C58 C -0.2150(9) 0.1587(6) 0.0926(8) 0.054(4) Uani 1 d . . H58A H -0.2079 0.1629 0.1443 0.064 Uiso 1 calc . . H58B H -0.2491 0.1339 0.0854 0.064 Uiso 1 calc . . C59 C -0.2524(9) 0.1993(5) 0.0606(8) 0.043(4) Uani 1 d . . H59A H -0.3014 0.2048 0.0835 0.052 Uiso 1 calc . . H59B H -0.2617 0.1952 0.0092 0.052 Uiso 1 calc . . C60 C -0.1984(8) 0.2377(5) 0.0731(7) 0.038(3) Uani 1 d . . H60A H -0.2202 0.2639 0.0514 0.046 Uiso 1 calc . . H60B H -0.1919 0.2428 0.1245 0.046 Uiso 1 calc . . C61 C 0.3770(8) 0.4629(4) 0.0772(7) 0.031(3) Uani 1 d . . H61A H 0.3835 0.4726 0.0277 0.037 Uiso 1 calc . . H61B H 0.3264 0.4725 0.0925 0.037 Uiso 1 calc . . C62 C 0.4359(9) 0.4845(5) 0.1232(9) 0.053(4) Uani 1 d . . H62A H 0.4309 0.5157 0.1189 0.079 Uiso 1 calc . . H62B H 0.4863 0.4757 0.1079 0.079 Uiso 1 calc . . H62C H 0.4289 0.476 0.1726 0.079 Uiso 1 calc . . C63 C 0.2466(8) 0.4656(4) 0.3136(7) 0.032(3) Uani 1 d . . H63A H 0.2991 0.4761 0.3188 0.038 Uiso 1 calc . . H63B H 0.2277 0.4746 0.2663 0.038 Uiso 1 calc . . C64 C 0.2004(11) 0.4863(6) 0.3675(9) 0.063(5) Uani 1 d . . H64A H 0.2019 0.5175 0.3611 0.094 Uiso 1 calc . . H64B H 0.2202 0.479 0.4147 0.094 Uiso 1 calc . . H64C H 0.1481 0.4763 0.3629 0.094 Uiso 1 calc . . C65 C -0.0032(8) 0.4669(4) 0.1865(7) 0.034(3) Uani 1 d . . H65A H 0.0497 0.4749 0.1767 0.04 Uiso 1 calc . . H65B H -0.035 0.4767 0.1461 0.04 Uiso 1 calc . . C66 C -0.0284(9) 0.4897(5) 0.2533(8) 0.048(4) Uani 1 d . . H66A H -0.0233 0.5208 0.247 0.071 Uiso 1 calc . . H66B H 0.0032 0.4804 0.2934 0.071 Uiso 1 calc . . H66C H -0.0813 0.4826 0.2625 0.071 Uiso 1 calc . . C67 C 0.1249(8) 0.4600(4) -0.0476(7) 0.035(3) Uani 1 d . . H67A H 0.0723 0.4705 -0.0519 0.042 Uiso 1 calc . . H67B H 0.1462 0.4709 -0.0022 0.042 Uiso 1 calc . . C68 C 0.1702(8) 0.4780(5) -0.1077(8) 0.042(3) Uani 1 d . . H68A H 0.1687 0.5095 -0.1061 0.063 Uiso 1 calc . . H68B H 0.1486 0.468 -0.1529 0.063 Uiso 1 calc . . H68C H 0.2226 0.4682 -0.1033 0.063 Uiso 1 calc . . Br1 Br 0.4246(2) 0.24100(13) 0.0274(2) 0.0339(8) Uani 0.75 d A 1 Br1' Br 0.3984(7) 0.2425(4) 0.0460(6) 0.042(3) Uani 0.25 d B 2 Br2 Br 0.2979(3) 0.24427(18) 0.3408(3) 0.0432(11) Uani 0.75 d C 1 Br2' Br 0.3162(9) 0.2422(5) 0.3615(8) 0.031(2) Uani 0.25 d D 2 Br3 Br -0.0620(2) 0.24820(17) 0.2518(3) 0.0349(9) Uani 0.75 d E 1 Br3' Br -0.0378(7) 0.2485(5) 0.2350(7) 0.036(3) Uani 0.25 d F 2 Br4 Br 0.0557(3) 0.23939(13) -0.0691(2) 0.0614(11) Uani 0.75 d G 1 Br4' Br 0.0741(6) 0.2418(3) -0.0446(4) 0.0207(17) Uani 0.25 d H 2 C1A C 0.4951(5) 0.0825(3) 0.0072(4) 0.081(6) Uani 1 d . . Br1A Br 0.45016(10) 0.13855(5) 0.01677(9) 0.0524(5) Uani 1 d . . Cl1A Cl 0.5940(4) 0.0859(2) 0.0098(4) 0.1142(16) Uani 0.8 d I 1 Cl2A Cl 0.4634(5) 0.0502(2) 0.0770(4) 0.1142(16) Uani 0.8 d I 1 Cl3A Cl 0.4646(5) 0.0622(2) -0.0751(3) 0.1142(16) Uani 0.8 d I 1 Cl1' Cl 0.5488(7) 0.0703(7) 0.0834(5) 0.1142(16) Uani 0.2 d I 2 Cl2' Cl 0.4174(8) 0.0473(7) -0.0018(6) 0.1142(16) Uani 0.2 d I 2 Cl3' Cl 0.5553(6) 0.0716(8) -0.0662(5) 0.1142(16) Uani 0.2 d I 2 C1B C 0.3382(6) 0.0758(4) 0.3621(8) 0.043(4) Uani 1 d . . Br1B Br 0.32487(8) 0.13742(5) 0.35870(8) 0.0434(4) Uani 1 d . . Cl1B Cl 0.3630(3) 0.05689(15) 0.2779(3) 0.0779(15) Uani 1 d . . Cl2B Cl 0.4089(3) 0.06258(15) 0.4229(4) 0.095(2) Uani 1 d . . Cl3B Cl 0.2526(3) 0.05117(15) 0.3852(4) 0.0868(17) Uani 1 d . . C1C C -0.1096(6) 0.0848(3) 0.2759(8) 0.053(4) Uani 1 d . . Br1C Br -0.08134(10) 0.14444(5) 0.26651(9) 0.0532(5) Uani 1 d . . Cl1C Cl -0.0970(3) 0.06866(13) 0.3642(2) 0.0656(13) Uani 1 d . . Cl2C Cl -0.2069(4) 0.0815(2) 0.2551(4) 0.112(2) Uani 1 d . . Cl3C Cl -0.0569(4) 0.05336(15) 0.2194(3) 0.103(2) Uani 1 d . . C1D C 0.0111(6) 0.0708(2) -0.1037(5) 0.093(7) Uani 1 d . . Br1D Br 0.02551(12) 0.13093(7) -0.08610(11) 0.0723(6) Uani 1 d . . Cl1D Cl -0.0605(6) 0.0510(2) -0.0507(4) 0.148(4) Uani 1 d . . Cl2D Cl -0.0060(4) 0.06185(18) -0.1938(3) 0.0926(18) Uani 1 d . . Cl3D Cl 0.0939(5) 0.0419(2) -0.0835(4) 0.129(3) Uani 1 d . . C1E C 0.6741(8) 0.4302(4) 0.1353(7) 0.040(3) Uani 1 d . . Br1E Br 0.76481(9) 0.39766(5) 0.12454(9) 0.0480(4) Uani 1 d . . Cl1E Cl 0.59670(16) 0.39385(9) 0.14860(15) 0.0267(6) Uani 1 d . . Cl3E Cl 0.6559(2) 0.46077(11) 0.05800(19) 0.0452(9) Uani 1 d . . Cl2E Cl 0.6828(2) 0.46490(12) 0.20825(19) 0.0474(9) Uani 1 d . . C1F C 0.1621(5) 0.1061(4) 0.1346(6) 0.071(13) Uani 0.5 d . . Br1F Br 0.2643(3) 0.11927(19) 0.1079(3) 0.118(2) Uani 0.5 d . . Cl1F Cl 0.1619(6) 0.0994(5) 0.2266(4) 0.097(4) Uani 0.5 d . . Cl2F Cl 0.1233(8) 0.0576(4) 0.1026(7) 0.105(4) Uani 0.5 d . . Cl3F Cl 0.1115(9) 0.1481(5) 0.0941(11) 0.154(7) Uani 0.5 d . . O1W O 0.2745(5) 0.4561(3) 0.5442(5) 0.047(3) Uani 1 d . . O2W O 0.2161(6) 0.5203(4) 0.6377(6) 0.064(3) Uani 1 d . . O3W O 0.1580(12) 0.4440(6) 0.6467(14) 0.067(8) Uani 0.5 d . . Br1G Br 0.0931(5) 0.2656(3) 0.1627(4) 0.051(2) Uani 0.2 d J 1 Br2G Br 0.2528(10) 0.2544(4) 0.1103(8) 0.045(2) Uani 0.1 d K 2 Br3G Br 0.1884(6) 0.3352(3) 0.1531(5) 0.045(2) Uani 0.15 d L 3 Br4G Br 0.1384(6) 0.2621(3) 0.0586(5) 0.070(3) Uani 0.2 d M 4 Br5G Br 0.2308(9) 0.2617(6) 0.2139(9) 0.056(4) Uani 0.1 d N 5 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 N30 0.048(7) 0.024(6) 0.025(6) -0.005(4) 0.003(5) 0.002(5) N32 0.025(6) 0.024(5) 0.035(6) 0.001(4) 0.008(4) 0.006(4) N34 0.036(6) 0.032(6) 0.025(6) 0.002(5) 0.000(5) -0.002(5) N36 0.032(6) 0.026(6) 0.036(6) 0.002(5) 0.006(5) -0.006(5) O4 0.033(5) 0.029(5) 0.033(5) -0.004(4) 0.007(4) 0.006(4) O6 0.026(5) 0.035(5) 0.041(5) -0.012(4) -0.001(4) 0.001(4) O11 0.029(5) 0.033(5) 0.033(5) 0.004(4) 0.006(4) 0.007(4) O13 0.027(5) 0.028(5) 0.030(5) 0.000(4) 0.008(4) 0.001(4) O18 0.032(5) 0.027(5) 0.040(5) 0.007(4) 0.007(4) -0.004(4) O20 0.033(5) 0.039(5) 0.026(5) 0.006(4) 0.005(4) -0.002(4) O25 0.034(5) 0.030(5) 0.031(5) 0.000(4) 0.007(4) 0.002(4) O27 0.026(5) 0.036(5) 0.034(5) 0.003(4) 0.003(4) -0.003(4) C1 0.040(8) 0.025(6) 0.022(6) -0.003(5) 0.015(6) -0.006(6) C2 0.031(7) 0.018(6) 0.030(7) 0.003(5) 0.010(5) 0.001(5) C3 0.023(7) 0.030(7) 0.028(7) -0.005(5) -0.001(5) -0.001(5) C4 0.025(7) 0.033(7) 0.029(7) 0.011(5) 0.007(5) 0.007(6) C5 0.034(7) 0.025(6) 0.025(6) 0.002(5) 0.009(5) 0.011(5) C6 0.022(7) 0.018(6) 0.035(7) -0.002(5) 0.001(5) -0.006(5) C7 0.021(7) 0.024(6) 0.034(7) 0.005(5) -0.002(5) 0.002(5) C8 0.023(7) 0.024(6) 0.033(7) 0.002(5) -0.003(5) -0.005(5) C9 0.027(7) 0.022(6) 0.032(7) 0.000(5) 0.001(5) -0.002(5) C10 0.034(8) 0.031(7) 0.037(8) -0.001(6) 0.005(6) -0.012(6) C11 0.031(7) 0.023(6) 0.033(7) -0.003(5) -0.003(6) -0.005(5) C12 0.024(7) 0.031(7) 0.031(7) 0.001(5) -0.001(5) -0.004(5) C13 0.025(7) 0.016(6) 0.030(7) -0.007(5) 0.003(5) -0.003(5) C14 0.022(7) 0.039(8) 0.025(6) -0.005(5) 0.006(5) 0.005(5) C15 0.026(7) 0.034(7) 0.031(7) -0.010(6) 0.009(5) 0.010(6) C16 0.028(7) 0.025(6) 0.030(7) 0.004(5) 0.006(5) 0.005(5) C17 0.036(8) 0.021(6) 0.031(7) 0.002(5) 0.005(6) 0.003(5) C18 0.042(8) 0.024(7) 0.030(7) -0.004(5) 0.011(6) 0.002(6) C19 0.020(7) 0.029(7) 0.032(7) 0.002(5) 0.010(5) -0.001(5) C20 0.034(7) 0.026(7) 0.021(6) 0.001(5) 0.012(5) 0.004(5) C21 0.028(7) 0.021(6) 0.036(7) 0.002(5) 0.001(5) -0.002(5) C22 0.030(7) 0.019(6) 0.037(7) -0.003(5) 0.006(6) 0.009(5) C23 0.020(7) 0.028(7) 0.046(8) 0.007(6) 0.003(6) -0.002(5) C24 0.027(7) 0.028(7) 0.023(6) 0.008(5) 0.009(5) 0.001(5) C25 0.027(7) 0.029(7) 0.022(6) 0.003(5) 0.006(5) 0.010(5) C26 0.034(8) 0.021(6) 0.040(8) 0.012(6) 0.006(6) 0.000(5) C27 0.017(6) 0.032(7) 0.032(7) 0.004(5) 0.003(5) 0.008(5) C28 0.032(7) 0.031(7) 0.024(6) 0.003(5) -0.005(5) 0.003(6) C29 0.036(7) 0.024(6) 0.028(7) -0.008(5) 0.008(6) 0.004(5) C31 0.039(8) 0.023(7) 0.029(7) -0.002(5) -0.002(6) 0.009(6) C33 0.037(8) 0.027(7) 0.031(7) -0.006(5) 0.012(6) -0.003(6) C35 0.029(7) 0.026(7) 0.046(8) 0.006(6) 0.001(6) -0.001(6) C37 0.041(8) 0.018(6) 0.036(7) -0.009(5) 0.010(6) 0.004(6) C38 0.053(9) 0.027(7) 0.041(8) -0.005(6) -0.001(7) -0.003(6) C39 0.072(12) 0.037(9) 0.061(11) -0.002(8) 0.021(9) -0.001(8) C40 0.088(14) 0.034(9) 0.071(12) -0.028(8) 0.024(10) -0.018(9) C41 0.054(10) 0.046(9) 0.048(9) -0.017(7) 0.001(7) -0.013(8) C42 0.042(8) 0.034(8) 0.039(8) -0.008(6) 0.012(6) 0.004(6) C43 0.048(9) 0.031(7) 0.029(7) 0.002(6) 0.012(6) 0.015(6) C44 0.039(8) 0.032(7) 0.042(8) -0.003(6) 0.000(6) 0.007(6) C45 0.032(8) 0.059(10) 0.050(9) 0.009(8) -0.006(7) 0.022(7) C46 0.064(11) 0.058(11) 0.049(10) -0.011(8) -0.002(8) 0.039(9) C47 0.076(12) 0.032(8) 0.049(9) 0.009(7) 0.006(8) 0.014(8) C48 0.055(10) 0.030(8) 0.046(9) 0.006(6) 0.015(7) 0.004(7) C49 0.032(7) 0.029(7) 0.024(6) 0.005(5) 0.008(5) -0.005(5) C50 0.039(8) 0.030(7) 0.049(9) 0.003(6) 0.006(7) 0.004(6) C51 0.062(10) 0.026(7) 0.043(9) 0.012(6) 0.019(7) 0.003(7) C52 0.077(12) 0.034(9) 0.063(11) 0.022(8) 0.016(9) 0.010(8) C53 0.039(8) 0.054(9) 0.026(7) 0.018(6) 0.003(6) 0.013(7) C54 0.036(8) 0.039(8) 0.047(9) 0.013(7) -0.004(7) -0.002(6) C55 0.037(8) 0.030(7) 0.033(7) -0.004(6) 0.010(6) -0.012(6) C56 0.050(9) 0.020(7) 0.059(9) 0.005(6) 0.015(7) 0.002(6) C57 0.063(11) 0.034(8) 0.058(10) 0.003(7) 0.015(8) 0.005(7) C58 0.059(11) 0.063(11) 0.039(9) 0.006(8) -0.001(8) -0.020(9) C59 0.058(10) 0.037(8) 0.035(8) 0.008(6) -0.006(7) -0.014(7) C60 0.031(8) 0.048(9) 0.037(8) -0.003(6) 0.003(6) -0.005(6) C61 0.041(8) 0.023(7) 0.028(7) 0.003(5) -0.001(6) 0.001(6) C62 0.054(10) 0.031(8) 0.073(11) -0.001(8) -0.004(8) -0.006(7) C63 0.035(8) 0.027(7) 0.033(7) -0.008(5) 0.002(6) -0.004(6) C64 0.079(13) 0.045(10) 0.064(11) -0.012(8) 0.015(9) 0.002(9) C65 0.042(8) 0.027(7) 0.032(7) 0.003(6) 0.007(6) 0.009(6) C66 0.058(10) 0.043(9) 0.043(9) -0.004(7) 0.014(7) 0.013(7) C67 0.033(8) 0.027(7) 0.044(8) 0.009(6) -0.004(6) -0.004(6) C68 0.038(8) 0.033(8) 0.054(9) 0.017(7) 0.005(7) -0.004(6) Br1 0.040(2) 0.0281(12) 0.0332(18) 0.0003(11) 0.0059(11) 0.0042(13) Br1' 0.058(8) 0.029(4) 0.038(6) -0.001(4) -0.011(4) 0.008(5) Br2 0.043(3) 0.0302(14) 0.057(3) 0.003(2) 0.0226(19) -0.0012(16) Br2' 0.037(6) 0.024(4) 0.033(6) 0.006(4) -0.005(3) -0.001(4) Br3 0.037(2) 0.0311(13) 0.037(2) 0.0029(13) 0.0040(13) -0.0044(15) Br3' 0.049(8) 0.025(3) 0.033(6) 0.006(4) -0.007(5) -0.009(5) Br4 0.073(3) 0.0418(17) 0.070(3) 0.011(2) 0.039(2) 0.0154(19) Br4' 0.022(3) 0.028(3) 0.012(4) -0.005(3) -0.006(2) 0.001(2) C1A 0.114(17) 0.057(12) 0.074(13) -0.001(10) 0.030(12) 0.029(12) Br1A 0.0702(11) 0.0372(8) 0.0500(9) 0.0038(7) 0.0099(8) 0.0034(8) Cl1A 0.158(4) 0.066(2) 0.120(3) 0.011(2) 0.050(3) 0.021(3) Cl2A 0.158(4) 0.066(2) 0.120(3) 0.011(2) 0.050(3) 0.021(3) Cl3A 0.158(4) 0.066(2) 0.120(3) 0.011(2) 0.050(3) 0.021(3) Cl1' 0.158(4) 0.066(2) 0.120(3) 0.011(2) 0.050(3) 0.021(3) Cl2' 0.158(4) 0.066(2) 0.120(3) 0.011(2) 0.050(3) 0.021(3) Cl3' 0.158(4) 0.066(2) 0.120(3) 0.011(2) 0.050(3) 0.021(3) C1B 0.037(8) 0.024(7) 0.069(10) 0.005(7) 0.018(7) 0.001(6) Br1B 0.0463(9) 0.0304(8) 0.0537(9) -0.0012(6) 0.0102(7) -0.0034(6) Cl1B 0.102(4) 0.047(3) 0.085(3) -0.016(2) 0.020(3) 0.003(3) Cl2B 0.109(4) 0.042(3) 0.131(5) 0.000(3) -0.066(4) 0.005(3) Cl3B 0.067(3) 0.046(3) 0.148(5) 0.012(3) 0.026(3) -0.019(2) C1C 0.085(12) 0.043(9) 0.033(8) 0.002(7) 0.007(8) -0.006(9) Br1C 0.0706(12) 0.0370(9) 0.0522(10) 0.0023(7) 0.0050(8) -0.0036(8) Cl1C 0.111(4) 0.041(2) 0.044(2) 0.0084(18) 0.003(2) 0.002(2) Cl2C 0.099(4) 0.085(4) 0.150(6) 0.060(4) -0.045(4) -0.043(3) Cl3C 0.176(6) 0.038(2) 0.095(4) -0.011(2) 0.082(4) 0.006(3) C1D 0.112(18) 0.061(13) 0.105(17) 0.013(12) 0.017(14) -0.009(13) Br1D 0.0759(14) 0.0633(12) 0.0783(13) 0.0068(10) 0.0174(10) 0.0063(10) Cl1D 0.227(8) 0.074(4) 0.147(6) -0.016(4) 0.119(6) -0.046(5) Cl2D 0.137(5) 0.068(3) 0.072(3) -0.006(3) 0.022(3) 0.031(3) Cl3D 0.163(7) 0.084(4) 0.140(6) -0.005(4) -0.046(5) 0.052(5) C1E 0.051(9) 0.025(7) 0.044(8) -0.001(6) -0.003(7) 0.003(6) Br1E 0.0457(9) 0.0417(9) 0.0569(10) 0.0026(7) 0.0089(7) 0.0029(7) Cl1E 0.0239(16) 0.0240(15) 0.0325(16) 0.0001(12) 0.0080(12) -0.0004(12) Cl3E 0.056(2) 0.0366(19) 0.043(2) 0.0087(16) 0.0033(17) 0.0036(17) Cl2E 0.064(3) 0.0336(19) 0.045(2) -0.0049(16) 0.0075(18) 0.0007(17) C1F 0.08(3) 0.10(3) 0.030(17) 0.018(17) -0.002(16) 0.07(2) Br1F 0.121(4) 0.100(4) 0.134(5) 0.066(4) 0.051(4) 0.022(3) Cl1F 0.062(6) 0.197(12) 0.033(5) -0.017(6) -0.001(4) -0.006(7) Cl2F 0.106(9) 0.099(9) 0.111(9) -0.047(8) -0.008(7) 0.007(7) Cl3F 0.118(10) 0.102(9) 0.240(15) 0.018(9) -0.110(10) 0.043(8) O1W 0.044(6) 0.033(5) 0.063(7) 0.006(5) 0.023(5) 0.010(4) O2W 0.037(6) 0.089(9) 0.066(8) -0.011(7) 0.018(5) 0.017(6) O3W 0.043(12) 0.032(11) 0.13(2) 0.023(12) 0.065(13) 0.022(10) Br1G 0.054(5) 0.064(5) 0.035(4) -0.009(3) 0.024(3) -0.030(4) Br2G 0.074(6) 0.021(4) 0.042(4) -0.012(3) 0.013(4) 0.017(4) Br3G 0.074(6) 0.021(4) 0.042(4) -0.012(3) 0.013(4) 0.017(4) Br4G 0.085(7) 0.075(6) 0.051(5) -0.004(4) 0.019(5) 0.003(5) Br5G 0.044(9) 0.058(10) 0.066(11) 0.013(8) -0.004(8) 0.014(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N30 C29 1.516(16) . ? N30 C37 1.524(15) . ? N30 H30A 0.99 . ? N30 H30B 0.99 . ? N32 C43 1.484(16) . ? N32 C31 1.528(16) . ? N32 H32A 0.99 . ? N32 H32B 0.99 . ? N34 C33 1.487(16) . ? N34 C49 1.542(15) . ? N34 H34A 0.99 . ? N34 H34B 0.99 . ? N36 C35 1.480(16) . ? N36 C55 1.540(16) . ? N36 H36A 0.99 . ? N36 H36B 0.99 . ? O4 C4 1.382(15) . ? O4 H4 0.84 . ? O6 C6 1.380(14) . ? O6 H6 0.84 . ? O11 C11 1.413(15) . ? O11 H11 0.84 . ? O13 C13 1.362(14) . ? O13 H13 0.84 . ? O18 C18 1.403(16) . ? O18 H18 0.84 . ? O20 C20 1.412(15) . ? O20 H20 0.84 . ? O25 C25 1.399(14) . ? O25 H25 0.84 . ? O27 C27 1.352(15) . ? O27 H27 0.84 . ? C1 C2 1.380(17) . ? C1 C6 1.411(17) . ? C1 C28 1.480(18) . ? C2 C3 1.407(17) . ? C2 H2 0.95 . ? C3 C4 1.403(18) . ? C3 C7 1.516(17) . ? C4 C5 1.373(18) . ? C5 C6 1.394(17) . ? C5 C29 1.502(16) . ? C7 C8 1.529(17) . ? C7 C61 1.556(16) . ? C7 H7 1 . ? C8 C9 1.373(17) . ? C8 C13 1.412(17) . ? C9 C10 1.398(18) . ? C9 H9 0.95 . ? C10 C11 1.375(18) . ? C10 C14 1.532(18) . ? C11 C12 1.392(18) . ? C12 C13 1.374(17) . ? C12 C31 1.524(17) . ? C14 C63 1.538(18) . ? C14 C15 1.537(18) . ? C14 H14 1 . ? C15 C20 1.362(18) . ? C15 C16 1.411(17) . ? C16 C17 1.403(18) . ? C16 H16 0.95 . ? C17 C18 1.380(17) . ? C17 C21 1.493(17) . ? C18 C19 1.359(18) . ? C19 C20 1.395(18) . ? C19 C33 1.531(17) . ? C21 C65 1.531(17) . ? C21 C22 1.561(17) . ? C21 H21 1 . ? C22 C27 1.360(18) . ? C22 C23 1.398(18) . ? C23 C24 1.380(18) . ? C23 H23 0.95 . ? C24 C25 1.389(17) . ? C24 C28 1.542(17) . ? C25 C26 1.404(17) . ? C26 C27 1.411(18) . ? C26 C35 1.501(18) . ? C28 C67 1.562(17) . ? C28 H28 1 . ? C29 H29A 0.99 . ? C29 H29B 0.99 . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? C33 H33A 0.99 . ? C33 H33B 0.99 . ? C35 H35A 0.99 . ? C35 H35B 0.99 . ? C37 C38 1.521(19) . ? C37 C42 1.522(19) . ? C37 H37 1 . ? C38 C39 1.54(2) . ? C38 H38A 0.99 . ? C38 H38B 0.99 . ? C39 C40 1.51(3) . ? C39 H39A 0.99 . ? C39 H39B 0.99 . ? C40 C41 1.53(2) . ? C40 H40A 0.99 . ? C40 H40B 0.99 . ? C41 C42 1.527(19) . ? C41 H41A 0.99 . ? C41 H41B 0.99 . ? C42 H42A 0.99 . ? C42 H42B 0.99 . ? C43 C44 1.53(2) . ? C43 C48 1.55(2) . ? C43 H43 1 . ? C44 C45 1.530(18) . ? C44 H44A 0.99 . ? C44 H44B 0.99 . ? C45 C46 1.56(2) . ? C45 H45A 0.99 . ? C45 H45B 0.99 . ? C46 C47 1.46(2) . ? C46 H46A 0.99 . ? C46 H46B 0.99 . ? C47 C48 1.56(2) . ? C47 H47A 0.99 . ? C47 H47B 0.99 . ? C48 H48A 0.99 . ? C48 H48B 0.99 . ? C49 C50 1.494(18) . ? C49 C54 1.517(19) . ? C49 H49 1 . ? C50 C51 1.533(18) . ? C50 H50A 0.99 . ? C50 H50B 0.99 . ? C51 C52 1.55(2) . ? C51 H51A 0.99 . ? C51 H51B 0.99 . ? C52 C53 1.53(2) . ? C52 H52A 0.99 . ? C52 H52B 0.99 . ? C53 C54 1.541(19) . ? C53 H53A 0.99 . ? C53 H53B 0.99 . ? C54 H54A 0.99 . ? C54 H54B 0.99 . ? C55 C60 1.492(19) . ? C55 C56 1.515(19) . ? C55 H55 1 . ? C56 C57 1.53(2) . ? C56 H56A 0.99 . ? C56 H56B 0.99 . ? C57 C58 1.47(2) . ? C57 H57A 0.99 . ? C57 H57B 0.99 . ? C58 C59 1.55(2) . ? C58 H58A 0.99 . ? C58 H58B 0.99 . ? C59 C60 1.548(19) . ? C59 H59A 0.99 . ? C59 H59B 0.99 . ? C60 H60A 0.99 . ? C60 H60B 0.99 . ? C61 C62 1.506(19) . ? C61 H61A 0.99 . ? C61 H61B 0.99 . ? C62 H62A 0.98 . ? C62 H62B 0.98 . ? C62 H62C 0.98 . ? C63 C64 1.46(2) . ? C63 H63A 0.99 . ? C63 H63B 0.99 . ? C64 H64A 0.98 . ? C64 H64B 0.98 . ? C64 H64C 0.98 . ? C65 C66 1.519(18) . ? C65 H65A 0.99 . ? C65 H65B 0.99 . ? C66 H66A 0.98 . ? C66 H66B 0.98 . ? C66 H66C 0.98 . ? C67 C68 1.507(19) . ? C67 H67A 0.99 . ? C67 H67B 0.99 . ? C68 H68A 0.98 . ? C68 H68B 0.98 . ? C68 H68C 0.98 . ? C1A Cl1' 1.756(7) . ? C1A Cl3A 1.757(7) . ? C1A Cl1A 1.754(7) . ? C1A Cl2A 1.759(7) . ? C1A Cl2' 1.766(7) . ? C1A Cl3' 1.793(7) . ? C1A Br1A 1.927(8) . ? C1B Cl2B 1.737(16) . ? C1B Cl1B 1.755(16) . ? C1B Cl3B 1.759(8) . ? C1B Br1B 1.936(13) . ? C1C Cl3C 1.730(14) . ? C1C Cl1C 1.753(14) . ? C1C Cl2C 1.765(9) . ? C1C Br1C 1.932(7) . ? C1D Cl1D 1.737(9) . ? C1D Cl2D 1.746(9) . ? C1D Cl3D 1.757(9) . ? C1D Br1D 1.919(7) . ? C1E Cl2E 1.756(14) . ? C1E Cl3E 1.769(14) . ? C1E Cl1E 1.798(15) . ? C1E Br1E 1.913(14) . ? C1F Cl1F 1.750(9) . ? C1F Cl3F 1.755(9) . ? C1F Cl2F 1.762(9) . ? C1F Br1F 1.929(8) . ? 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 C29 N30 C37 115.0(10) . . ? C29 N30 H30A 108.5 . . ? C37 N30 H30A 108.5 . . ? C29 N30 H30B 108.5 . . ? C37 N30 H30B 108.5 . . ? H30A N30 H30B 107.5 . . ? C43 N32 C31 113.4(10) . . ? C43 N32 H32A 108.9 . . ? C31 N32 H32A 108.9 . . ? C43 N32 H32B 108.9 . . ? C31 N32 H32B 108.9 . . ? H32A N32 H32B 107.7 . . ? C33 N34 C49 114.8(9) . . ? C33 N34 H34A 108.6 . . ? C49 N34 H34A 108.6 . . ? C33 N34 H34B 108.6 . . ? C49 N34 H34B 108.6 . . ? H34A N34 H34B 107.6 . . ? C35 N36 C55 113.8(10) . . ? C35 N36 H36A 108.8 . . ? C55 N36 H36A 108.8 . . ? C35 N36 H36B 108.8 . . ? C55 N36 H36B 108.8 . . ? H36A N36 H36B 107.7 . . ? C4 O4 H4 109.5 . . ? C6 O6 H6 109.5 . . ? C11 O11 H11 109.5 . . ? C13 O13 H13 109.5 . . ? C18 O18 H18 109.5 . . ? C20 O20 H20 109.5 . . ? C25 O25 H25 109.5 . . ? C27 O27 H27 109.5 . . ? C2 C1 C6 116.7(12) . . ? C2 C1 C28 123.8(11) . . ? C6 C1 C28 119.5(11) . . ? C1 C2 C3 123.3(11) . . ? C1 C2 H2 118.4 . . ? C3 C2 H2 118.4 . . ? C4 C3 C2 117.2(11) . . ? C4 C3 C7 121.9(11) . . ? C2 C3 C7 120.9(11) . . ? O4 C4 C5 121.5(11) . . ? O4 C4 C3 116.5(11) . . ? C5 C4 C3 121.9(11) . . ? C4 C5 C6 118.8(11) . . ? C4 C5 C29 124.2(11) . . ? C6 C5 C29 117.0(11) . . ? O6 C6 C1 123.7(11) . . ? O6 C6 C5 114.1(10) . . ? C1 C6 C5 122.2(11) . . ? C8 C7 C3 110.2(10) . . ? C8 C7 C61 112.2(10) . . ? C3 C7 C61 113.5(10) . . ? C8 C7 H7 106.8 . . ? C3 C7 H7 106.8 . . ? C61 C7 H7 106.8 . . ? C9 C8 C13 116.0(11) . . ? C9 C8 C7 123.5(11) . . ? C13 C8 C7 120.5(11) . . ? C8 C9 C10 124.0(12) . . ? C8 C9 H9 118 . . ? C10 C9 H9 118 . . ? C11 C10 C9 117.3(12) . . ? C11 C10 C14 122.3(12) . . ? C9 C10 C14 120.4(12) . . ? C10 C11 C12 121.7(12) . . ? C10 C11 O11 117.3(11) . . ? C12 C11 O11 121.0(11) . . ? C11 C12 C13 118.7(12) . . ? C11 C12 C31 122.1(11) . . ? C13 C12 C31 119.0(11) . . ? O13 C13 C12 114.4(11) . . ? O13 C13 C8 123.3(11) . . ? C12 C13 C8 122.2(11) . . ? C63 C14 C15 112.0(10) . . ? C63 C14 C10 114.0(10) . . ? C15 C14 C10 112.4(10) . . ? C63 C14 H14 105.9 . . ? C15 C14 H14 105.9 . . ? C10 C14 H14 105.9 . . ? C20 C15 C16 115.6(12) . . ? C20 C15 C14 122.9(12) . . ? C16 C15 C14 121.5(12) . . ? C17 C16 C15 123.4(12) . . ? C17 C16 H16 118.3 . . ? C15 C16 H16 118.3 . . ? C18 C17 C16 116.4(12) . . ? C18 C17 C21 123.6(12) . . ? C16 C17 C21 120.0(11) . . ? C19 C18 C17 122.7(13) . . ? C19 C18 O18 120.8(11) . . ? C17 C18 O18 116.5(12) . . ? C18 C19 C20 118.6(11) . . ? C18 C19 C33 124.0(11) . . ? C20 C19 C33 117.4(11) . . ? C15 C20 C19 123.3(12) . . ? C15 C20 O20 122.5(11) . . ? C19 C20 O20 114.1(10) . . ? C17 C21 C65 114.7(10) . . ? C17 C21 C22 111.7(10) . . ? C65 C21 C22 111.8(10) . . ? C17 C21 H21 106 . . ? C65 C21 H21 106 . . ? C22 C21 H21 106 . . ? C27 C22 C23 119.5(12) . . ? C27 C22 C21 121.4(11) . . ? C23 C22 C21 119.1(11) . . ? C22 C23 C24 121.8(12) . . ? C22 C23 H23 119.1 . . ? C24 C23 H23 119.1 . . ? C25 C24 C23 118.0(11) . . ? C25 C24 C28 120.0(11) . . ? C23 C24 C28 122.0(11) . . ? C24 C25 O25 118.3(10) . . ? C24 C25 C26 121.7(11) . . ? O25 C25 C26 119.8(11) . . ? C27 C26 C25 117.8(12) . . ? C27 C26 C35 118.3(11) . . ? C25 C26 C35 123.8(12) . . ? C22 C27 O27 125.9(12) . . ? C22 C27 C26 121.1(12) . . ? O27 C27 C26 113.0(11) . . ? C1 C28 C24 113.3(10) . . ? C1 C28 C67 112.1(11) . . ? C24 C28 C67 111.0(10) . . ? C1 C28 H28 106.6 . . ? C24 C28 H28 106.6 . . ? C67 C28 H28 106.6 . . ? C5 C29 N30 110.2(10) . . ? C5 C29 H29A 109.6 . . ? N30 C29 H29A 109.6 . . ? C5 C29 H29B 109.6 . . ? N30 C29 H29B 109.6 . . ? H29A C29 H29B 108.1 . . ? C12 C31 N32 109.9(10) . . ? C12 C31 H31A 109.7 . . ? N32 C31 H31A 109.7 . . ? C12 C31 H31B 109.7 . . ? N32 C31 H31B 109.7 . . ? H31A C31 H31B 108.2 . . ? N34 C33 C19 110.5(10) . . ? N34 C33 H33A 109.6 . . ? C19 C33 H33A 109.6 . . ? N34 C33 H33B 109.6 . . ? C19 C33 H33B 109.6 . . ? H33A C33 H33B 108.1 . . ? N36 C35 C26 111.7(11) . . ? N36 C35 H35A 109.3 . . ? C26 C35 H35A 109.3 . . ? N36 C35 H35B 109.3 . . ? C26 C35 H35B 109.3 . . ? H35A C35 H35B 107.9 . . ? N30 C37 C38 107.0(10) . . ? N30 C37 C42 109.9(10) . . ? C38 C37 C42 111.8(11) . . ? N30 C37 H37 109.4 . . ? C38 C37 H37 109.4 . . ? C42 C37 H37 109.4 . . ? C37 C38 C39 109.0(12) . . ? C37 C38 H38A 109.9 . . ? C39 C38 H38A 109.9 . . ? C37 C38 H38B 109.9 . . ? C39 C38 H38B 109.9 . . ? H38A C38 H38B 108.3 . . ? C38 C39 C40 110.4(13) . . ? C38 C39 H39A 109.6 . . ? C40 C39 H39A 109.6 . . ? C38 C39 H39B 109.6 . . ? C40 C39 H39B 109.6 . . ? H39A C39 H39B 108.1 . . ? C41 C40 C39 112.0(14) . . ? C41 C40 H40A 109.2 . . ? C39 C40 H40A 109.2 . . ? C41 C40 H40B 109.2 . . ? C39 C40 H40B 109.2 . . ? H40A C40 H40B 107.9 . . ? C40 C41 C42 109.4(13) . . ? C40 C41 H41A 109.8 . . ? C42 C41 H41A 109.8 . . ? C40 C41 H41B 109.8 . . ? C42 C41 H41B 109.8 . . ? H41A C41 H41B 108.2 . . ? C41 C42 C37 109.7(12) . . ? C41 C42 H42A 109.7 . . ? C37 C42 H42A 109.7 . . ? C41 C42 H42B 109.7 . . ? C37 C42 H42B 109.7 . . ? H42A C42 H42B 108.2 . . ? N32 C43 C44 111.0(11) . . ? N32 C43 C48 109.1(11) . . ? C44 C43 C48 109.4(11) . . ? N32 C43 H43 109.1 . . ? C44 C43 H43 109.1 . . ? C48 C43 H43 109.1 . . ? C43 C44 C45 109.7(12) . . ? C43 C44 H44A 109.7 . . ? C45 C44 H44A 109.7 . . ? C43 C44 H44B 109.7 . . ? C45 C44 H44B 109.7 . . ? H44A C44 H44B 108.2 . . ? C44 C45 C46 109.5(12) . . ? C44 C45 H45A 109.8 . . ? C46 C45 H45A 109.8 . . ? C44 C45 H45B 109.8 . . ? C46 C45 H45B 109.8 . . ? H45A C45 H45B 108.2 . . ? C47 C46 C45 111.1(13) . . ? C47 C46 H46A 109.4 . . ? C45 C46 H46A 109.4 . . ? C47 C46 H46B 109.4 . . ? C45 C46 H46B 109.4 . . ? H46A C46 H46B 108 . . ? C46 C47 C48 112.5(13) . . ? C46 C47 H47A 109.1 . . ? C48 C47 H47A 109.1 . . ? C46 C47 H47B 109.1 . . ? C48 C47 H47B 109.1 . . ? H47A C47 H47B 107.8 . . ? C47 C48 C43 109.3(13) . . ? C47 C48 H48A 109.8 . . ? C43 C48 H48A 109.8 . . ? C47 C48 H48B 109.8 . . ? C43 C48 H48B 109.8 . . ? H48A C48 H48B 108.3 . . ? C50 C49 C54 114.3(12) . . ? C50 C49 N34 108.2(10) . . ? C54 C49 N34 109.7(10) . . ? C50 C49 H49 108.2 . . ? C54 C49 H49 108.2 . . ? N34 C49 H49 108.2 . . ? C49 C50 C51 110.1(11) . . ? C49 C50 H50A 109.6 . . ? C51 C50 H50A 109.6 . . ? C49 C50 H50B 109.6 . . ? C51 C50 H50B 109.6 . . ? H50A C50 H50B 108.2 . . ? C50 C51 C52 110.4(12) . . ? C50 C51 H51A 109.6 . . ? C52 C51 H51A 109.6 . . ? C50 C51 H51B 109.6 . . ? C52 C51 H51B 109.6 . . ? H51A C51 H51B 108.1 . . ? C53 C52 C51 110.3(12) . . ? C53 C52 H52A 109.6 . . ? C51 C52 H52A 109.6 . . ? C53 C52 H52B 109.6 . . ? C51 C52 H52B 109.6 . . ? H52A C52 H52B 108.1 . . ? C52 C53 C54 111.4(12) . . ? C52 C53 H53A 109.3 . . ? C54 C53 H53A 109.3 . . ? C52 C53 H53B 109.3 . . ? C54 C53 H53B 109.3 . . ? H53A C53 H53B 108 . . ? C49 C54 C53 109.4(11) . . ? C49 C54 H54A 109.8 . . ? C53 C54 H54A 109.8 . . ? C49 C54 H54B 109.8 . . ? C53 C54 H54B 109.8 . . ? H54A C54 H54B 108.2 . . ? C60 C55 C56 112.7(12) . . ? C60 C55 N36 109.7(10) . . ? C56 C55 N36 108.0(11) . . ? C60 C55 H55 108.8 . . ? C56 C55 H55 108.8 . . ? N36 C55 H55 108.8 . . ? C55 C56 C57 110.6(13) . . ? C55 C56 H56A 109.5 . . ? C57 C56 H56A 109.5 . . ? C55 C56 H56B 109.5 . . ? C57 C56 H56B 109.5 . . ? H56A C56 H56B 108.1 . . ? C58 C57 C56 110.4(13) . . ? C58 C57 H57A 109.6 . . ? C56 C57 H57A 109.6 . . ? C58 C57 H57B 109.6 . . ? C56 C57 H57B 109.6 . . ? H57A C57 H57B 108.1 . . ? C57 C58 C59 112.3(13) . . ? C57 C58 H58A 109.1 . . ? C59 C58 H58A 109.1 . . ? C57 C58 H58B 109.1 . . ? C59 C58 H58B 109.1 . . ? H58A C58 H58B 107.9 . . ? C58 C59 C60 108.2(12) . . ? C58 C59 H59A 110.1 . . ? C60 C59 H59A 110.1 . . ? C58 C59 H59B 110.1 . . ? C60 C59 H59B 110.1 . . ? H59A C59 H59B 108.4 . . ? C55 C60 C59 109.6(12) . . ? C55 C60 H60A 109.8 . . ? C59 C60 H60A 109.8 . . ? C55 C60 H60B 109.8 . . ? C59 C60 H60B 109.8 . . ? H60A C60 H60B 108.2 . . ? C62 C61 C7 114.5(11) . . ? C62 C61 H61A 108.6 . . ? C7 C61 H61A 108.6 . . ? C62 C61 H61B 108.6 . . ? C7 C61 H61B 108.6 . . ? H61A C61 H61B 107.6 . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C64 C63 C14 114.7(12) . . ? C64 C63 H63A 108.6 . . ? C14 C63 H63A 108.6 . . ? C64 C63 H63B 108.6 . . ? C14 C63 H63B 108.6 . . ? H63A C63 H63B 107.6 . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C66 C65 C21 112.9(11) . . ? C66 C65 H65A 109 . . ? C21 C65 H65A 109 . . ? C66 C65 H65B 109 . . ? C21 C65 H65B 109 . . ? H65A C65 H65B 107.8 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C68 C67 C28 113.1(12) . . ? C68 C67 H67A 109 . . ? C28 C67 H67A 109 . . ? C68 C67 H67B 109 . . ? C28 C67 H67B 109 . . ? H67A C67 H67B 107.8 . . ? C67 C68 H68A 109.5 . . ? C67 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? C67 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 109.5 . . ? Cl3A C1A Cl1A 109.9(4) . . ? Cl3A C1A Cl2A 111.0(5) . . ? Cl1A C1A Cl2A 110.1(4) . . ? Cl1' C1A Cl2' 110.9(6) . . ? Cl1' C1A Cl3' 105.8(6) . . ? Cl2' C1A Cl3' 106.2(6) . . ? Cl1' C1A Br1A 109.8(9) . . ? Cl3A C1A Br1A 106.7(5) . . ? Cl1A C1A Br1A 110.9(5) . . ? Cl2A C1A Br1A 108.2(4) . . ? Cl2' C1A Br1A 104.4(9) . . ? Cl3' C1A Br1A 119.6(9) . . ? Cl2B C1B Cl1B 109.4(7) . . ? Cl2B C1B Cl3B 110.4(8) . . ? Cl1B C1B Cl3B 107.8(8) . . ? Cl2B C1B Br1B 110.1(7) . . ? Cl1B C1B Br1B 109.5(7) . . ? Cl3B C1B Br1B 109.6(7) . . ? Cl3C C1C Cl1C 111.2(6) . . ? Cl3C C1C Cl2C 111.3(8) . . ? Cl1C C1C Cl2C 107.8(7) . . ? Cl3C C1C Br1C 110.2(6) . . ? Cl1C C1C Br1C 109.4(6) . . ? Cl2C C1C Br1C 106.8(5) . . ? Cl1D C1D Cl2D 112.7(6) . . ? Cl1D C1D Cl3D 107.9(7) . . ? Cl2D C1D Cl3D 105.2(6) . . ? Cl1D C1D Br1D 110.0(5) . . ? Cl2D C1D Br1D 110.2(5) . . ? Cl3D C1D Br1D 110.7(5) . . ? Cl2E C1E Cl3E 109.3(8) . . ? Cl2E C1E Cl1E 109.7(8) . . ? Cl3E C1E Cl1E 108.9(7) . . ? Cl2E C1E Br1E 110.2(7) . . ? Cl3E C1E Br1E 110.0(7) . . ? Cl1E C1E Br1E 108.9(7) . . ? Cl1F C1F Cl3F 120.9(12) . . ? Cl1F C1F Cl2F 103.5(8) . . ? Cl3F C1F Cl2F 107.1(9) . . ? Cl1F C1F Br1F 107.4(7) . . ? Cl3F C1F Br1F 101.6(8) . . ? Cl2F C1F Br1F 117.1(9) . . ? 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 C6 C1 C2 C3 0.0(17) . . . . ? C28 C1 C2 C3 -179.8(12) . . . . ? C1 C2 C3 C4 0.5(18) . . . . ? C1 C2 C3 C7 179.5(11) . . . . ? C2 C3 C4 O4 177.6(10) . . . . ? C7 C3 C4 O4 -1.3(17) . . . . ? C2 C3 C4 C5 -0.3(18) . . . . ? C7 C3 C4 C5 -179.2(11) . . . . ? O4 C4 C5 C6 -178.3(11) . . . . ? C3 C4 C5 C6 -0.5(18) . . . . ? O4 C4 C5 C29 -0.2(19) . . . . ? C3 C4 C5 C29 177.7(12) . . . . ? C2 C1 C6 O6 -179.9(11) . . . . ? C28 C1 C6 O6 -0.1(18) . . . . ? C2 C1 C6 C5 -0.9(17) . . . . ? C28 C1 C6 C5 178.9(11) . . . . ? C4 C5 C6 O6 -179.8(11) . . . . ? C29 C5 C6 O6 1.9(16) . . . . ? C4 C5 C6 C1 1.1(18) . . . . ? C29 C5 C6 C1 -177.2(11) . . . . ? C4 C3 C7 C8 -92.6(14) . . . . ? C2 C3 C7 C8 88.5(14) . . . . ? C4 C3 C7 C61 140.5(12) . . . . ? C2 C3 C7 C61 -38.4(16) . . . . ? C3 C7 C8 C9 -87.7(14) . . . . ? C61 C7 C8 C9 39.9(16) . . . . ? C3 C7 C8 C13 90.7(13) . . . . ? C61 C7 C8 C13 -141.7(11) . . . . ? C13 C8 C9 C10 0.4(18) . . . . ? C7 C8 C9 C10 178.9(11) . . . . ? C8 C9 C10 C11 -1.1(19) . . . . ? C8 C9 C10 C14 179.6(11) . . . . ? C9 C10 C11 C12 1.9(18) . . . . ? C14 C10 C11 C12 -178.8(11) . . . . ? C9 C10 C11 O11 -179.8(10) . . . . ? C14 C10 C11 O11 -0.5(18) . . . . ? C10 C11 C12 C13 -2.2(18) . . . . ? O11 C11 C12 C13 179.6(10) . . . . ? C10 C11 C12 C31 173.6(12) . . . . ? O11 C11 C12 C31 -4.6(18) . . . . ? C11 C12 C13 O13 -179.5(10) . . . . ? C31 C12 C13 O13 4.5(16) . . . . ? C11 C12 C13 C8 1.5(18) . . . . ? C31 C12 C13 C8 -174.5(11) . . . . ? C9 C8 C13 O13 -179.5(10) . . . . ? C7 C8 C13 O13 1.9(17) . . . . ? C9 C8 C13 C12 -0.6(17) . . . . ? C7 C8 C13 C12 -179.2(11) . . . . ? C11 C10 C14 C63 141.1(12) . . . . ? C9 C10 C14 C63 -39.6(16) . . . . ? C11 C10 C14 C15 -90.1(15) . . . . ? C9 C10 C14 C15 89.2(14) . . . . ? C63 C14 C15 C20 -143.0(12) . . . . ? C10 C14 C15 C20 87.1(14) . . . . ? C63 C14 C15 C16 38.6(15) . . . . ? C10 C14 C15 C16 -91.3(14) . . . . ? C20 C15 C16 C17 0.1(18) . . . . ? C14 C15 C16 C17 178.7(11) . . . . ? C15 C16 C17 C18 1.3(18) . . . . ? C15 C16 C17 C21 -177.3(11) . . . . ? C16 C17 C18 C19 -1.6(18) . . . . ? C21 C17 C18 C19 177.0(12) . . . . ? C16 C17 C18 O18 178.5(10) . . . . ? C21 C17 C18 O18 -2.9(18) . . . . ? C17 C18 C19 C20 0.4(19) . . . . ? O18 C18 C19 C20 -179.7(11) . . . . ? C17 C18 C19 C33 179.7(12) . . . . ? O18 C18 C19 C33 -0.4(19) . . . . ? C16 C15 C20 C19 -1.4(17) . . . . ? C14 C15 C20 C19 -179.9(11) . . . . ? C16 C15 C20 O20 -178.1(10) . . . . ? C14 C15 C20 O20 3.4(18) . . . . ? C18 C19 C20 C15 1.2(19) . . . . ? C33 C19 C20 C15 -178.1(11) . . . . ? C18 C19 C20 O20 178.1(10) . . . . ? C33 C19 C20 O20 -1.2(15) . . . . ? C18 C17 C21 C65 144.4(12) . . . . ? C16 C17 C21 C65 -37.1(16) . . . . ? C18 C17 C21 C22 -87.1(15) . . . . ? C16 C17 C21 C22 91.4(13) . . . . ? C17 C21 C22 C27 90.4(14) . . . . ? C65 C21 C22 C27 -139.5(12) . . . . ? C17 C21 C22 C23 -89.7(13) . . . . ? C65 C21 C22 C23 40.4(15) . . . . ? C27 C22 C23 C24 -1.0(18) . . . . ? C21 C22 C23 C24 179.1(11) . . . . ? C22 C23 C24 C25 -1.1(18) . . . . ? C22 C23 C24 C28 -178.9(11) . . . . ? C23 C24 C25 O25 178.5(10) . . . . ? C28 C24 C25 O25 -3.6(17) . . . . ? C23 C24 C25 C26 2.4(18) . . . . ? C28 C24 C25 C26 -179.8(11) . . . . ? C24 C25 C26 C27 -1.6(18) . . . . ? O25 C25 C26 C27 -177.7(10) . . . . ? C24 C25 C26 C35 175.0(12) . . . . ? O25 C25 C26 C35 -1.1(18) . . . . ? C23 C22 C27 O27 -178.5(11) . . . . ? C21 C22 C27 O27 1.4(19) . . . . ? C23 C22 C27 C26 1.8(18) . . . . ? C21 C22 C27 C26 -178.3(11) . . . . ? C25 C26 C27 C22 -0.5(18) . . . . ? C35 C26 C27 C22 -177.3(11) . . . . ? C25 C26 C27 O27 179.8(10) . . . . ? C35 C26 C27 O27 3.0(16) . . . . ? C2 C1 C28 C24 -87.4(14) . . . . ? C6 C1 C28 C24 92.9(14) . . . . ? C2 C1 C28 C67 39.3(16) . . . . ? C6 C1 C28 C67 -140.5(12) . . . . ? C25 C24 C28 C1 -92.7(14) . . . . ? C23 C24 C28 C1 85.0(15) . . . . ? C25 C24 C28 C67 140.1(12) . . . . ? C23 C24 C28 C67 -42.2(15) . . . . ? C4 C5 C29 N30 106.8(14) . . . . ? C6 C5 C29 N30 -75.0(14) . . . . ? C37 N30 C29 C5 175.2(10) . . . . ? C11 C12 C31 N32 113.2(13) . . . . ? C13 C12 C31 N32 -71.0(14) . . . . ? C43 N32 C31 C12 173.0(10) . . . . ? C49 N34 C33 C19 175.1(10) . . . . ? C18 C19 C33 N34 106.8(14) . . . . ? C20 C19 C33 N34 -74.0(14) . . . . ? C55 N36 C35 C26 176.8(10) . . . . ? C27 C26 C35 N36 -72.7(15) . . . . ? C25 C26 C35 N36 110.7(14) . . . . ? C29 N30 C37 C38 166.3(11) . . . . ? C29 N30 C37 C42 -72.1(14) . . . . ? N30 C37 C38 C39 178.9(12) . . . . ? C42 C37 C38 C39 58.5(16) . . . . ? C37 C38 C39 C40 -56.6(18) . . . . ? C38 C39 C40 C41 57.3(19) . . . . ? C39 C40 C41 C42 -57.2(19) . . . . ? C40 C41 C42 C37 56.9(17) . . . . ? N30 C37 C42 C41 -178.1(11) . . . . ? C38 C37 C42 C41 -59.4(15) . . . . ? C31 N32 C43 C44 -72.8(14) . . . . ? C31 N32 C43 C48 166.7(11) . . . . ? N32 C43 C44 C45 178.7(11) . . . . ? C48 C43 C44 C45 -61.0(15) . . . . ? C43 C44 C45 C46 59.6(16) . . . . ? C44 C45 C46 C47 -57.4(17) . . . . ? C45 C46 C47 C48 56.0(18) . . . . ? C46 C47 C48 C43 -56.4(17) . . . . ? N32 C43 C48 C47 179.1(11) . . . . ? C44 C43 C48 C47 57.6(15) . . . . ? C33 N34 C49 C50 164.8(11) . . . . ? C33 N34 C49 C54 -69.9(14) . . . . ? C54 C49 C50 C51 56.8(15) . . . . ? N34 C49 C50 C51 179.3(11) . . . . ? C49 C50 C51 C52 -56.0(16) . . . . ? C50 C51 C52 C53 56.8(17) . . . . ? C51 C52 C53 C54 -56.6(17) . . . . ? C50 C49 C54 C53 -55.6(15) . . . . ? N34 C49 C54 C53 -177.2(10) . . . . ? C52 C53 C54 C49 54.6(16) . . . . ? C35 N36 C55 C60 -72.3(14) . . . . ? C35 N36 C55 C56 164.6(11) . . . . ? C60 C55 C56 C57 55.7(16) . . . . ? N36 C55 C56 C57 177.0(11) . . . . ? C55 C56 C57 C58 -54.7(17) . . . . ? C56 C57 C58 C59 58.0(18) . . . . ? C57 C58 C59 C60 -59.3(17) . . . . ? C56 C55 C60 C59 -57.6(15) . . . . ? N36 C55 C60 C59 -178.0(10) . . . . ? C58 C59 C60 C55 57.2(16) . . . . ? C8 C7 C61 C62 59.7(15) . . . . ? C3 C7 C61 C62 -174.5(12) . . . . ? C15 C14 C63 C64 59.9(16) . . . . ? C10 C14 C63 C64 -171.0(13) . . . . ? C17 C21 C65 C66 -64.3(15) . . . . ? C22 C21 C65 C66 167.3(11) . . . . ? C1 C28 C67 C68 64.3(14) . . . . ? C24 C28 C67 C68 -167.8(11) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 967819' ####################################################################### # # 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_8@4 _audit_creation_date 2013-09-24T20:49:25-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_melting_point ? _chemical_formula_moiety 'C80 H128 N4 O8, 4(Cl), C4 H8 O2' _chemical_formula_sum 'C84 H136 Cl4 N4 O10' _chemical_formula_weight 1503.76 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.9721(4) _cell_length_b 16.4049(5) _cell_length_c 20.2775(5) _cell_angle_alpha 77.8360(10) _cell_angle_beta 83.606(2) _cell_angle_gamma 63.8360(10) _cell_volume 4368.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 123.0(1) _cell_measurement_reflns_used 10856 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 28.7 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.23 _exptl_crystal_density_diffrn 1.143 _exptl_crystal_F_000 1632 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Sheldrick, G. M. SADABS 2008/2; University of G\"ottingen: G\"ottingen, Germany, 2008. ; _exptl_absorpt_correction_T_min 0.5759 _exptl_absorpt_correction_T_max 0.7457 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123.0(1) _diffrn_source 'Enraf Nonius FR590' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Bruker-Nonius Kappa Apex II Diffractometer' _diffrn_measurement_method '\w and \f scans' _diffrn_reflns_av_unetI/netI 0.0846 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_number 32607 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.584 _diffrn_reflns_theta_max 25.499 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.995 _reflns_number_total 16172 _reflns_number_gt 10486 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'MERCURY (Macrae et al., 2006)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1796P)^2^+14.2628P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 16172 _refine_ls_number_parameters 973 _refine_ls_number_restraints 111 _refine_ls_R_factor_all 0.1560 _refine_ls_R_factor_gt 0.1087 _refine_ls_wR_factor_ref 0.3413 _refine_ls_wR_factor_gt 0.2918 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.875 _refine_diff_density_min -1.074 _refine_diff_density_rms 0.107 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group N30 N 0.0984(3) 0.6985(3) 0.3569(2) 0.0340(10) Uani 1 d . . H30A H 0.0474 0.6784 0.3499 0.041 Uiso 1 calc . . H30B H 0.1456 0.6873 0.3179 0.041 Uiso 1 calc . . N32 N 0.4485(4) 0.6778(3) 0.1563(2) 0.0462(12) Uani 1 d . . H32A H 0.4145 0.6775 0.201 0.055 Uiso 1 calc . . H32B H 0.4002 0.6889 0.122 0.055 Uiso 1 calc . . N34 N 0.1755(3) 0.6010(3) -0.0129(2) 0.0336(10) Uani 1 d . . H34A H 0.2447 0.5845 -0.0015 0.04 Uiso 1 calc . . H34B H 0.1308 0.6335 0.0223 0.04 Uiso 1 calc . . N36 N -0.2106(3) 0.5603(3) 0.3197(2) 0.0300(9) Uani 1 d . . H36A H -0.2049 0.5909 0.2728 0.036 Uiso 1 calc . . H36B H -0.1701 0.5724 0.3484 0.036 Uiso 1 calc . . O4 O 0.3630(3) 0.5604(3) 0.38146(19) 0.0357(8) Uani 1 d . . H4 H 0.334 0.6074 0.3522 0.054 Uiso 1 calc . . O6 O 0.0698(2) 0.5080(2) 0.44741(16) 0.0301(8) Uani 1 d . . H6 H 0.0327 0.5537 0.42 0.045 Uiso 1 calc . . O11 O 0.4950(3) 0.4779(3) 0.07483(17) 0.0347(8) Uani 1 d . . H11 H 0.4566 0.534 0.0632 0.052 Uiso 1 calc . . O13 O 0.5192(3) 0.5348(3) 0.29148(18) 0.0358(8) Uani 1 d . . H13 H 0.4809 0.5417 0.3255 0.054 Uiso 1 calc . . O18 O 0.0580(3) 0.4397(3) 0.08388(18) 0.0389(9) Uani 1 d . . H18 H 0.0294 0.4213 0.1178 0.058 Uiso 1 calc . . O20 O 0.3621(3) 0.4497(3) 0.01105(16) 0.0323(8) Uani 1 d . . H20 H 0.4064 0.4555 0.0291 0.049 Uiso 1 calc . . O25 O -0.0572(2) 0.4243(3) 0.42741(16) 0.0310(8) Uani 1 d . . H25 H -0.025 0.4392 0.4502 0.047 Uiso 1 calc . . O27 O -0.0579(3) 0.4037(3) 0.19625(16) 0.0330(8) Uani 1 d . . H27 H -0.1083 0.4546 0.1947 0.049 Uiso 1 calc . . C1 C 0.2197(3) 0.3865(3) 0.4185(2) 0.0257(10) Uani 1 d . . C2 C 0.3190(4) 0.3555(3) 0.3982(2) 0.0276(10) Uani 1 d . . H2 H 0.3553 0.2926 0.3936 0.033 Uiso 1 calc . . C3 C 0.3680(4) 0.4131(4) 0.3842(2) 0.0282(11) Uani 1 d . . C4 C 0.3132(4) 0.5051(4) 0.3910(2) 0.0283(10) Uani 1 d . . C5 C 0.2122(4) 0.5399(3) 0.4108(2) 0.0275(10) Uani 1 d . . C6 C 0.1675(4) 0.4789(4) 0.4242(2) 0.0278(10) Uani 1 d . . C7 C 0.4778(4) 0.3785(4) 0.3621(2) 0.0303(11) Uani 1 d . . H7 H 0.5054 0.4136 0.3816 0.036 Uiso 1 calc . . C8 C 0.4853(3) 0.4044(3) 0.2852(2) 0.0278(10) Uani 1 d . . C9 C 0.4751(4) 0.3534(4) 0.2429(2) 0.0300(11) Uani 1 d . . H9 H 0.464 0.3007 0.2628 0.036 Uiso 1 calc . . C10 C 0.4802(3) 0.3745(3) 0.1727(2) 0.0286(11) Uani 1 d . . C11 C 0.4935(3) 0.4542(4) 0.1440(2) 0.0297(11) Uani 1 d . . C12 C 0.5084(4) 0.5062(4) 0.1849(2) 0.0294(11) Uani 1 d . . C13 C 0.5041(4) 0.4808(4) 0.2549(2) 0.0297(11) Uani 1 d . . C14 C 0.4716(3) 0.3145(3) 0.1284(2) 0.0274(10) Uani 1 d . . H14 H 0.5032 0.3278 0.0838 0.033 Uiso 1 calc . . C15 C 0.3627(4) 0.3429(3) 0.1147(2) 0.0259(10) Uani 1 d . . C16 C 0.3051(4) 0.3053(3) 0.1577(2) 0.0280(10) Uani 1 d . . H16 H 0.3366 0.2584 0.1951 0.034 Uiso 1 calc . . C17 C 0.2042(4) 0.3325(3) 0.1488(2) 0.0266(10) Uani 1 d . . C18 C 0.1568(4) 0.4044(4) 0.0955(2) 0.0291(11) Uani 1 d . . C19 C 0.2122(4) 0.4425(3) 0.0494(2) 0.0281(10) Uani 1 d . . C20 C 0.3140(4) 0.4102(3) 0.0596(2) 0.0279(10) Uani 1 d . . C21 C 0.1475(4) 0.2835(3) 0.1931(2) 0.0282(10) Uani 1 d . . H21 H 0.0936 0.29 0.1646 0.034 Uiso 1 calc . . C22 C 0.0948(4) 0.3283(3) 0.2538(2) 0.0273(10) Uani 1 d . . C23 C 0.1470(4) 0.3143(3) 0.3112(2) 0.0281(10) Uani 1 d . . H23 H 0.2175 0.2818 0.3096 0.034 Uiso 1 calc . . C24 C 0.1020(4) 0.3453(3) 0.3706(2) 0.0255(10) Uani 1 d . . C25 C -0.0014(4) 0.3938(3) 0.3714(2) 0.0273(10) Uani 1 d . . C26 C -0.0579(4) 0.4134(3) 0.3139(2) 0.0266(10) Uani 1 d . . C27 C -0.0079(4) 0.3832(4) 0.2553(2) 0.0276(10) Uani 1 d . . C28 C 0.1647(4) 0.3247(3) 0.4316(2) 0.0277(10) Uani 1 d . . H28 H 0.1175 0.3428 0.4706 0.033 Uiso 1 calc . . C29 C 0.1544(4) 0.6385(4) 0.4196(3) 0.0316(11) Uani 1 d . . H29A H 0.2006 0.6621 0.4303 0.038 Uiso 1 calc . . H29B H 0.1067 0.6417 0.458 0.038 Uiso 1 calc . . C31 C 0.5346(4) 0.5855(4) 0.1554(3) 0.0363(12) Uani 1 d . . H31A H 0.5895 0.5807 0.1813 0.044 Uiso 1 calc . . H31B H 0.5587 0.5807 0.1082 0.044 Uiso 1 calc . . C33 C 0.1647(4) 0.5134(4) -0.0117(2) 0.0340(12) Uani 1 d . . H33A H 0.0932 0.5276 -0.0115 0.041 Uiso 1 calc . . H33B H 0.1963 0.4881 -0.0529 0.041 Uiso 1 calc . . C35 C -0.1687(4) 0.4585(3) 0.3218(2) 0.0283(10) Uani 1 d . . H35A H -0.1882 0.4294 0.3654 0.034 Uiso 1 calc . . H35B H -0.1984 0.4472 0.2854 0.034 Uiso 1 calc . . C37 C 0.0479(4) 0.8006(4) 0.3565(3) 0.0393(13) Uani 1 d . . H37 H 0.0997 0.8223 0.36 0.047 Uiso 1 calc . . C38 C -0.0025(5) 0.8470(4) 0.2890(3) 0.0505(15) Uani 1 d . . H38A H -0.0491 0.8213 0.2829 0.061 Uiso 1 calc . . H38B H 0.0484 0.8337 0.2522 0.061 Uiso 1 calc . . C39 C -0.0597(6) 0.9516(4) 0.2843(4) 0.0623(19) Uani 1 d . . H39A H -0.0123 0.9786 0.2846 0.075 Uiso 1 calc . . H39B H -0.0958 0.9791 0.2413 0.075 Uiso 1 calc . . C40 C -0.1332(5) 0.9746(5) 0.3427(4) 0.0609(18) Uani 1 d . . H40A H -0.1843 0.9526 0.3401 0.073 Uiso 1 calc . . H40B H -0.1672 1.0424 0.34 0.073 Uiso 1 calc . . C41 C -0.0798(5) 0.9292(5) 0.4097(4) 0.0541(17) Uani 1 d . . H41A H -0.1288 0.9445 0.4474 0.065 Uiso 1 calc . . H41B H -0.031 0.9536 0.4132 0.065 Uiso 1 calc . . C42 C -0.0259(5) 0.8242(4) 0.4152(3) 0.0456(14) Uani 1 d . . H42A H 0.0097 0.796 0.4584 0.055 Uiso 1 calc . . H42B H -0.0749 0.7991 0.4145 0.055 Uiso 1 calc . . C43 C 0.4804(7) 0.7551(5) 0.1420(5) 0.089(3) Uani 1 d . . H43 H 0.5282 0.7415 0.178 0.107 Uiso 1 calc . . C44 C 0.5355(8) 0.7595(7) 0.0762(5) 0.089(3) Uani 1 d . . H44A H 0.4944 0.7646 0.0392 0.107 Uiso 1 calc . . H44B H 0.5979 0.7021 0.0769 0.107 Uiso 1 calc . . C45 C 0.5600(9) 0.8430(8) 0.0636(6) 0.115(4) Uani 1 d . . H45A H 0.6082 0.8337 0.0973 0.138 Uiso 1 calc . . H45B H 0.5915 0.8482 0.0182 0.138 Uiso 1 calc . . C46 C 0.4686(10) 0.9304(9) 0.0680(7) 0.145(5) Uani 1 d . . H46A H 0.4865 0.9831 0.0586 0.174 Uiso 1 calc . . H46B H 0.421 0.9407 0.0335 0.174 Uiso 1 calc . . C47 C 0.4212(11) 0.9256(8) 0.1358(6) 0.125(4) Uani 1 d . . H47A H 0.3609 0.9839 0.1381 0.15 Uiso 1 calc . . H47B H 0.4678 0.9174 0.1703 0.15 Uiso 1 calc . . C48 C 0.3936(8) 0.8458(6) 0.1496(7) 0.120(4) Uani 1 d . . H48A H 0.3657 0.8406 0.1961 0.144 Uiso 1 calc . . H48B H 0.341 0.8585 0.1182 0.144 Uiso 1 calc . . C49 C 0.1514(4) 0.6660(4) -0.0803(3) 0.0395(13) Uani 1 d . . H49 H 0.0926 0.666 -0.0993 0.047 Uiso 1 calc . . C50 C 0.2406(5) 0.6306(4) -0.1277(3) 0.0432(14) Uani 1 d . . H50A H 0.2535 0.5678 -0.1334 0.052 Uiso 1 calc . . H50B H 0.3001 0.6263 -0.1076 0.052 Uiso 1 calc . . C51 C 0.2228(6) 0.6946(5) -0.1971(3) 0.0573(17) Uani 1 d . . H51A H 0.2832 0.6718 -0.2261 0.069 Uiso 1 calc . . H51B H 0.1673 0.6944 -0.2193 0.069 Uiso 1 calc . . C52 C 0.1977(7) 0.7924(5) -0.1887(4) 0.071(2) Uani 1 d . . H52A H 0.1819 0.8339 -0.2332 0.085 Uiso 1 calc . . H52B H 0.2562 0.7935 -0.1712 0.085 Uiso 1 calc . . C53 C 0.1087(6) 0.8271(5) -0.1399(4) 0.070(2) Uani 1 d . . H53A H 0.0486 0.8321 -0.1597 0.084 Uiso 1 calc . . H53B H 0.0962 0.8895 -0.1335 0.084 Uiso 1 calc . . C54 C 0.1271(6) 0.7628(4) -0.0720(3) 0.0571(18) Uani 1 d . . H54A H 0.1831 0.7626 -0.05 0.068 Uiso 1 calc . . H54B H 0.0671 0.7853 -0.0426 0.068 Uiso 1 calc . . C55 C -0.3177(4) 0.6027(4) 0.3429(3) 0.0334(11) Uani 1 d . . H55 H -0.3556 0.5801 0.3196 0.04 Uiso 1 calc . . C56 C -0.3297(4) 0.5745(4) 0.4187(3) 0.0372(12) Uani 1 d . . H56A H -0.2922 0.5954 0.4431 0.045 Uiso 1 calc . . H56B H -0.3024 0.5064 0.431 0.045 Uiso 1 calc . . C57 C -0.4400(4) 0.6179(5) 0.4391(3) 0.0475(15) Uani 1 d . . H57A H -0.4757 0.5917 0.4183 0.057 Uiso 1 calc . . H57B H -0.447 0.6024 0.4887 0.057 Uiso 1 calc . . C58 C -0.4868(5) 0.7222(5) 0.4172(3) 0.0532(17) Uani 1 d . . H58A H -0.5591 0.7471 0.4279 0.064 Uiso 1 calc . . H58B H -0.4573 0.7492 0.4427 0.064 Uiso 1 calc . . C59 C -0.4710(5) 0.7504(5) 0.3417(3) 0.0521(16) Uani 1 d . . H59A H -0.4973 0.8185 0.3298 0.063 Uiso 1 calc . . H59B H -0.508 0.7306 0.3159 0.063 Uiso 1 calc . . C60 C -0.3603(4) 0.7066(4) 0.3221(3) 0.0400(13) Uani 1 d . . H60A H -0.3519 0.723 0.2727 0.048 Uiso 1 calc . . H60B H -0.3241 0.7307 0.3445 0.048 Uiso 1 calc . . C61 C 0.5415(3) 0.2751(4) 0.3889(3) 0.0382(13) Uani 1 d . . H61A H 0.5267 0.2618 0.4377 0.046 Uiso 1 calc . . H61B H 0.5209 0.2384 0.3662 0.046 Uiso 1 calc . . C62 C 0.6511(3) 0.2432(4) 0.3792(3) 0.0522(17) Uani 1 d . . H62A H 0.6852 0.1785 0.4028 0.063 Uiso 1 calc . . H62B H 0.6682 0.2446 0.3305 0.063 Uiso 1 calc . . C63 C 0.6893(5) 0.3027(5) 0.4057(6) 0.134(3) Uani 1 d . . H63A H 0.643 0.3327 0.4412 0.161 Uiso 1 calc . . H63B H 0.6913 0.3519 0.3685 0.161 Uiso 1 calc . . C64 C 0.7935(4) 0.2442(8) 0.4346(4) 0.134(3) Uani 1 d . . H64A H 0.7926 0.1913 0.4684 0.161 Uiso 1 calc . . H64B H 0.8113 0.282 0.4581 0.161 Uiso 1 calc . . C65 C 0.8728(5) 0.2078(9) 0.3811(5) 0.134(3) Uani 1 d . . H65C H 0.8574 0.1666 0.3598 0.161 Uiso 1 calc . . H65D H 0.8702 0.2605 0.3456 0.161 Uiso 1 calc . . C66 C 0.9766(5) 0.1558(8) 0.4078(5) 0.111(4) Uani 1 d . . H66A H 1.0206 0.1195 0.3748 0.166 Uiso 1 calc . . H66B H 0.9762 0.1143 0.4503 0.166 Uiso 1 calc . . H66C H 1.0006 0.1996 0.4157 0.166 Uiso 1 calc . . C67 C 0.5306(4) 0.2113(4) 0.1558(3) 0.0358(12) Uani 1 d . . H67A H 0.595 0.2013 0.1725 0.043 Uiso 1 calc . . H67B H 0.4933 0.1925 0.1947 0.043 Uiso 1 calc . . C68 C 0.5506(5) 0.1507(4) 0.1045(3) 0.0522(16) Uani 1 d . . H68A H 0.5904 0.1678 0.0666 0.063 Uiso 1 calc . . H68B H 0.4863 0.1629 0.0864 0.063 Uiso 1 calc . . C69 C 0.6060(6) 0.0467(5) 0.1324(4) 0.0639(19) Uani 1 d . . H69A H 0.5672 0.03 0.1712 0.077 Uiso 1 calc . . H69B H 0.609 0.012 0.0971 0.077 Uiso 1 calc . . C70 C 0.7089(7) 0.0171(6) 0.1545(6) 0.096(3) Uani 1 d . . H70A H 0.7048 0.032 0.1999 0.115 Uiso 1 calc . . H70B H 0.7387 0.0541 0.1234 0.115 Uiso 1 calc . . C71 C 0.7781(8) -0.0838(6) 0.1574(5) 0.107(3) Uani 1 d . . H71A H 0.7754 -0.1038 0.1152 0.129 Uiso 1 calc . . H71B H 0.8475 -0.0951 0.1638 0.129 Uiso 1 calc . . C72 C 0.7425(10) -0.1350(9) 0.2165(6) 0.124(4) Uani 1 d . . H72A H 0.7469 -0.1153 0.2579 0.186 Uiso 1 calc . . H72B H 0.7841 -0.2015 0.2203 0.186 Uiso 1 calc . . H72C H 0.6732 -0.1217 0.2099 0.186 Uiso 1 calc . . C73 C 0.2111(4) 0.1791(4) 0.2140(3) 0.0359(12) Uani 1 d . . H73A H 0.2455 0.1531 0.1736 0.043 Uiso 1 calc . . H73B H 0.2625 0.1687 0.2456 0.043 Uiso 1 calc . . C74 C 0.1482(5) 0.1289(4) 0.2478(4) 0.0584(18) Uani 1 d . . H74A H 0.1253 0.1467 0.2925 0.07 Uiso 1 calc . . H74B H 0.0883 0.1515 0.2205 0.07 Uiso 1 calc . . C75 C 0.1969(7) 0.0264(5) 0.2576(5) 0.091(3) Uani 1 d . . H75A H 0.2143 0.0087 0.2125 0.109 Uiso 1 calc . . H75B H 0.1473 0.0036 0.2787 0.109 Uiso 1 calc . . C76 C 0.2891(8) -0.0235(7) 0.2995(6) 0.129(4) Uani 1 d . . H76A H 0.3187 -0.0895 0.2957 0.154 Uiso 1 calc . . H76B H 0.3378 0.001 0.2795 0.154 Uiso 1 calc . . C77 C 0.2760(12) -0.0174(10) 0.3723(7) 0.142(5) Uani 1 d . . H77A H 0.2339 0.0476 0.3771 0.17 Uiso 1 calc . . H77B H 0.3418 -0.0361 0.3912 0.17 Uiso 1 calc . . C78 C 0.2293(11) -0.0772(9) 0.4122(9) 0.163(6) Uani 1 d . . H78A H 0.1567 -0.0439 0.4092 0.244 Uiso 1 calc . . H78B H 0.2483 -0.0927 0.4595 0.244 Uiso 1 calc . . H78C H 0.2523 -0.134 0.3939 0.244 Uiso 1 calc . . C79 C 0.2308(4) 0.2212(4) 0.4502(3) 0.0321(11) Uani 1 d . . H79A H 0.1883 0.188 0.4556 0.039 Uiso 1 calc . . H79B H 0.2779 0.2017 0.4121 0.039 Uiso 1 calc . . C80 C 0.2901(4) 0.1917(4) 0.5140(3) 0.0352(12) Uani 1 d . . H80A H 0.2447 0.2188 0.5509 0.042 Uiso 1 calc . . H80B H 0.3406 0.2165 0.5063 0.042 Uiso 1 calc . . C81 C 0.3419(4) 0.0876(4) 0.5357(3) 0.0394(13) Uani 1 d . . H81A H 0.2906 0.0642 0.5493 0.047 Uiso 1 calc . . H81B H 0.3793 0.0602 0.4964 0.047 Uiso 1 calc . . C82 C 0.4129(4) 0.0549(4) 0.5933(3) 0.0410(13) Uani 1 d . . H82A H 0.3774 0.0865 0.6313 0.049 Uiso 1 calc . . H82B H 0.4681 0.0727 0.5783 0.049 Uiso 1 calc . . C83 C 0.4561(5) -0.0490(4) 0.6181(3) 0.0468(15) Uani 1 d . . H83A H 0.4019 -0.0659 0.6382 0.056 Uiso 1 calc . . H83B H 0.4848 -0.0807 0.5791 0.056 Uiso 1 calc . . C84 C 0.5366(5) -0.0823(5) 0.6703(3) 0.0524(16) Uani 1 d . . H84A H 0.5925 -0.0695 0.6496 0.079 Uiso 1 calc . . H84B H 0.5599 -0.1489 0.6862 0.079 Uiso 1 calc . . H84C H 0.5091 -0.0499 0.7084 0.079 Uiso 1 calc . . Cl1 Cl 0.28078(14) 0.72789(13) 0.27910(11) 0.0792(7) Uani 1 d . . Cl2 Cl 0.34910(12) 0.67484(11) 0.03045(8) 0.0516(4) Uani 1 d . . Cl3 Cl -0.22106(10) 0.59542(10) 0.16628(6) 0.0415(4) Uani 1 d . . Cl4 Cl -0.09382(12) 0.65946(11) 0.36552(10) 0.0563(5) Uani 1 d . . O1 O 0.1154(6) 0.6329(8) 0.1181(5) 0.058(3) Uani 0.65 d A 1 O2 O 0.1096(5) 0.5806(6) 0.2586(4) 0.0579(19) Uani 0.65 d A 1 C85 C 0.1959(8) 0.6127(10) 0.1591(5) 0.066(3) Uani 0.65 d A 1 H85A H 0.1892 0.6705 0.1715 0.079 Uiso 0.65 calc A 1 H85B H 0.2592 0.5872 0.1333 0.079 Uiso 0.65 calc A 1 C86 C 0.1987(8) 0.5450(8) 0.2218(5) 0.060(3) Uani 0.65 d A 1 H86A H 0.2084 0.4861 0.2098 0.072 Uiso 0.65 calc A 1 H86B H 0.2553 0.5324 0.2496 0.072 Uiso 0.65 calc A 1 C87 C 0.0305(8) 0.5977(10) 0.2184(5) 0.073(4) Uani 0.65 d A 1 H87A H -0.0327 0.6218 0.2445 0.088 Uiso 0.65 calc A 1 H87B H 0.0394 0.5388 0.2068 0.088 Uiso 0.65 calc A 1 C88 C 0.0239(8) 0.6652(10) 0.1548(6) 0.072(4) Uani 0.65 d A 1 H88A H -0.0306 0.673 0.1271 0.087 Uiso 0.65 calc A 1 H88B H 0.009 0.726 0.1658 0.087 Uiso 0.65 calc A 1 O1' O 0.0693(11) 0.6535(11) 0.1123(7) 0.036(4) Uani 0.35 d B 2 O2' O 0.1567(10) 0.6155(9) 0.2373(5) 0.045(3) Uani 0.35 d B 2 C85' C 0.1083(12) 0.7103(11) 0.1286(8) 0.051(5) Uani 0.35 d B 2 H85C H 0.0544 0.762 0.1474 0.061 Uiso 0.35 calc B 2 H85D H 0.1349 0.7368 0.087 0.061 Uiso 0.35 calc B 2 C86' C 0.1898(13) 0.6575(14) 0.1790(7) 0.052(5) Uani 0.35 d B 2 H86C H 0.2466 0.6097 0.1586 0.062 Uiso 0.35 calc B 2 H86D H 0.2134 0.7001 0.191 0.062 Uiso 0.35 calc B 2 C87' C 0.1209(15) 0.5568(11) 0.2207(10) 0.053(5) Uani 0.35 d B 2 H87C H 0.0959 0.5283 0.262 0.063 Uiso 0.35 calc B 2 H87D H 0.1756 0.5069 0.2008 0.063 Uiso 0.35 calc B 2 C88' C 0.0389(11) 0.6100(12) 0.1716(7) 0.036(4) Uani 0.35 d B 2 H88C H 0.0147 0.5676 0.16 0.043 Uiso 0.35 calc B 2 H88D H -0.0171 0.6573 0.1929 0.043 Uiso 0.35 calc 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 N30 0.034(2) 0.035(2) 0.034(2) -0.0107(19) 0.0041(18) -0.014(2) N32 0.060(3) 0.040(3) 0.040(3) -0.002(2) 0.005(2) -0.027(3) N34 0.038(2) 0.033(2) 0.027(2) -0.0059(18) -0.0048(18) -0.011(2) N36 0.026(2) 0.038(2) 0.029(2) -0.0103(18) -0.0023(17) -0.0147(19) O4 0.033(2) 0.044(2) 0.040(2) -0.0065(16) 0.0002(16) -0.0260(18) O6 0.0285(18) 0.038(2) 0.0258(17) -0.0053(14) 0.0015(14) -0.0163(16) O11 0.041(2) 0.039(2) 0.0270(17) 0.0007(15) -0.0026(15) -0.0228(18) O13 0.037(2) 0.048(2) 0.0331(19) -0.0081(16) 0.0010(15) -0.0269(18) O18 0.0288(19) 0.060(3) 0.0288(18) -0.0006(17) -0.0034(15) -0.0220(18) O20 0.034(2) 0.040(2) 0.0273(17) -0.0005(15) -0.0017(14) -0.0219(17) O25 0.0298(18) 0.043(2) 0.0252(17) -0.0101(15) 0.0033(14) -0.0198(16) O27 0.0278(18) 0.044(2) 0.0276(17) -0.0122(15) -0.0062(14) -0.0126(16) C1 0.025(2) 0.033(3) 0.020(2) -0.0006(19) -0.0024(18) -0.014(2) C2 0.033(3) 0.030(3) 0.021(2) -0.0026(19) -0.0017(19) -0.015(2) C3 0.024(2) 0.037(3) 0.026(2) 0.000(2) -0.0037(19) -0.017(2) C4 0.027(2) 0.036(3) 0.027(2) -0.002(2) -0.0020(19) -0.020(2) C5 0.026(2) 0.033(3) 0.026(2) -0.004(2) -0.0009(19) -0.016(2) C6 0.026(2) 0.040(3) 0.021(2) -0.006(2) 0.0002(18) -0.018(2) C7 0.026(2) 0.041(3) 0.026(2) 0.000(2) -0.0032(19) -0.018(2) C8 0.021(2) 0.034(3) 0.028(2) 0.000(2) -0.0028(19) -0.013(2) C9 0.026(2) 0.033(3) 0.031(3) -0.001(2) 0.000(2) -0.014(2) C10 0.020(2) 0.032(3) 0.033(3) -0.003(2) 0.0010(19) -0.012(2) C11 0.022(2) 0.036(3) 0.028(2) 0.002(2) -0.0015(19) -0.013(2) C12 0.030(3) 0.035(3) 0.028(2) -0.003(2) -0.003(2) -0.018(2) C13 0.027(2) 0.035(3) 0.031(3) -0.005(2) 0.000(2) -0.018(2) C14 0.024(2) 0.032(3) 0.026(2) -0.004(2) 0.0009(19) -0.013(2) C15 0.029(2) 0.027(2) 0.023(2) -0.0065(19) -0.0012(19) -0.012(2) C16 0.030(3) 0.031(3) 0.023(2) -0.0063(19) 0.0004(19) -0.013(2) C17 0.030(3) 0.031(3) 0.023(2) -0.0070(19) 0.0004(19) -0.016(2) C18 0.029(3) 0.037(3) 0.024(2) -0.008(2) -0.0004(19) -0.015(2) C19 0.030(3) 0.035(3) 0.020(2) -0.0020(19) -0.0030(19) -0.016(2) C20 0.033(3) 0.028(3) 0.025(2) -0.0051(19) 0.002(2) -0.016(2) C21 0.028(2) 0.035(3) 0.027(2) -0.007(2) -0.0003(19) -0.017(2) C22 0.030(3) 0.032(3) 0.024(2) -0.0053(19) 0.0012(19) -0.017(2) C23 0.026(2) 0.028(3) 0.030(2) -0.004(2) 0.001(2) -0.012(2) C24 0.030(3) 0.029(3) 0.022(2) -0.0012(19) 0.0004(19) -0.019(2) C25 0.034(3) 0.033(3) 0.022(2) -0.0030(19) 0.0002(19) -0.021(2) C26 0.027(2) 0.027(3) 0.028(2) -0.0034(19) 0.0005(19) -0.015(2) C27 0.029(3) 0.038(3) 0.025(2) -0.004(2) -0.0041(19) -0.022(2) C28 0.031(3) 0.035(3) 0.021(2) -0.0038(19) 0.0009(19) -0.019(2) C29 0.034(3) 0.034(3) 0.032(3) -0.012(2) 0.000(2) -0.017(2) C31 0.036(3) 0.040(3) 0.037(3) -0.002(2) 0.002(2) -0.022(3) C33 0.039(3) 0.042(3) 0.025(2) -0.002(2) -0.004(2) -0.021(3) C35 0.027(2) 0.036(3) 0.027(2) -0.009(2) -0.0011(19) -0.017(2) C37 0.037(3) 0.037(3) 0.048(3) -0.012(2) 0.008(2) -0.020(3) C38 0.057(4) 0.037(3) 0.051(4) -0.005(3) 0.000(3) -0.015(3) C39 0.066(5) 0.036(4) 0.074(5) -0.003(3) 0.001(4) -0.016(3) C40 0.054(4) 0.037(4) 0.088(5) -0.013(3) -0.001(4) -0.016(3) C41 0.042(3) 0.050(4) 0.077(5) -0.030(3) 0.012(3) -0.020(3) C42 0.044(3) 0.043(3) 0.051(3) -0.015(3) 0.009(3) -0.019(3) C43 0.107(6) 0.051(4) 0.089(5) 0.000(4) 0.044(5) -0.031(4) C44 0.118(8) 0.097(7) 0.073(5) 0.016(5) -0.016(5) -0.075(6) C45 0.131(7) 0.109(7) 0.119(7) 0.015(5) -0.010(6) -0.077(6) C46 0.176(9) 0.120(8) 0.160(9) -0.001(6) -0.015(7) -0.090(7) C47 0.160(12) 0.118(9) 0.145(11) -0.058(8) 0.014(9) -0.093(9) C48 0.145(8) 0.077(6) 0.134(7) -0.016(5) 0.023(6) -0.053(6) C49 0.046(3) 0.036(3) 0.034(3) 0.003(2) -0.014(2) -0.017(3) C50 0.052(4) 0.044(3) 0.035(3) 0.004(2) -0.002(3) -0.027(3) C51 0.070(4) 0.056(4) 0.045(4) 0.008(3) -0.004(3) -0.033(4) C52 0.087(6) 0.056(5) 0.071(5) 0.017(4) -0.018(4) -0.041(4) C53 0.088(6) 0.032(3) 0.080(5) 0.006(3) -0.040(4) -0.015(4) C54 0.072(5) 0.038(3) 0.052(4) -0.004(3) -0.025(3) -0.011(3) C55 0.025(2) 0.047(3) 0.031(3) -0.010(2) -0.001(2) -0.016(2) C56 0.031(3) 0.050(3) 0.034(3) -0.011(2) 0.001(2) -0.020(3) C57 0.039(3) 0.079(5) 0.033(3) -0.021(3) 0.007(2) -0.030(3) C58 0.031(3) 0.066(4) 0.052(4) -0.023(3) 0.000(3) -0.007(3) C59 0.038(3) 0.054(4) 0.053(4) -0.013(3) -0.005(3) -0.007(3) C60 0.037(3) 0.043(3) 0.036(3) -0.007(2) -0.006(2) -0.012(3) C61 0.035(3) 0.042(3) 0.032(3) 0.002(2) 0.000(2) -0.016(3) C62 0.035(3) 0.052(4) 0.049(4) 0.013(3) 0.000(3) -0.010(3) C63 0.121(5) 0.143(5) 0.148(5) -0.019(4) -0.016(4) -0.066(4) C64 0.121(5) 0.143(5) 0.148(5) -0.019(4) -0.016(4) -0.066(4) C65 0.121(5) 0.143(5) 0.148(5) -0.019(4) -0.016(4) -0.066(4) C66 0.051(5) 0.160(11) 0.085(6) -0.034(7) 0.020(5) -0.012(6) C67 0.032(3) 0.032(3) 0.040(3) -0.001(2) 0.000(2) -0.013(2) C68 0.059(4) 0.048(4) 0.051(4) -0.011(3) 0.001(3) -0.024(3) C69 0.084(5) 0.048(4) 0.068(5) -0.018(3) -0.008(4) -0.032(4) C70 0.082(5) 0.066(5) 0.126(7) -0.013(5) -0.034(5) -0.013(4) C71 0.093(7) 0.107(8) 0.106(8) -0.022(6) -0.005(6) -0.026(6) C72 0.122(4) 0.125(4) 0.125(4) -0.017(2) -0.003(2) -0.055(2) C73 0.039(3) 0.038(3) 0.035(3) -0.011(2) 0.002(2) -0.019(2) C74 0.074(5) 0.049(4) 0.062(4) -0.006(3) 0.010(4) -0.039(4) C75 0.102(7) 0.075(6) 0.099(7) 0.020(5) -0.024(6) -0.050(6) C76 0.146(8) 0.137(8) 0.123(8) -0.033(6) -0.014(6) -0.072(7) C77 0.158(9) 0.138(8) 0.129(8) -0.045(7) 0.002(7) -0.055(7) C78 0.135(10) 0.084(8) 0.226(14) 0.028(8) 0.016(10) -0.037(7) C79 0.032(3) 0.035(3) 0.031(3) 0.000(2) -0.006(2) -0.017(2) C80 0.040(3) 0.035(3) 0.029(3) 0.002(2) -0.007(2) -0.017(2) C81 0.039(3) 0.038(3) 0.040(3) 0.003(2) -0.005(2) -0.019(3) C82 0.038(3) 0.038(3) 0.039(3) 0.007(2) -0.006(2) -0.015(3) C83 0.045(3) 0.038(3) 0.049(3) 0.006(3) -0.007(3) -0.015(3) C84 0.052(4) 0.051(4) 0.044(3) 0.011(3) -0.009(3) -0.020(3) Cl1 0.0538(10) 0.0566(11) 0.0833(13) 0.0188(9) 0.0301(9) -0.0053(8) Cl2 0.0517(9) 0.0437(8) 0.0453(8) 0.0011(6) -0.0018(7) -0.0117(7) Cl3 0.0383(7) 0.0521(9) 0.0305(7) -0.0068(6) -0.0036(5) -0.0158(6) Cl4 0.0495(9) 0.0375(8) 0.0882(12) -0.0001(7) -0.0320(8) -0.0224(7) O1 0.050(6) 0.075(6) 0.044(5) -0.018(4) 0.004(5) -0.020(6) O2 0.065(5) 0.074(5) 0.036(4) -0.012(4) 0.002(3) -0.030(4) C85 0.053(7) 0.113(11) 0.046(6) -0.023(7) 0.011(5) -0.048(7) C86 0.057(7) 0.064(8) 0.052(6) -0.018(5) -0.015(5) -0.013(6) C87 0.057(8) 0.130(12) 0.054(7) -0.029(7) 0.007(6) -0.055(8) C88 0.054(7) 0.087(10) 0.052(8) -0.017(7) -0.010(6) -0.004(7) O1' 0.034(9) 0.057(10) 0.034(7) -0.025(7) 0.017(8) -0.031(8) O2' 0.060(8) 0.069(9) 0.031(6) -0.027(6) 0.020(5) -0.046(7) C85' 0.080(13) 0.064(12) 0.045(9) -0.039(9) 0.026(9) -0.057(11) C86' 0.057(9) 0.068(9) 0.046(8) -0.026(7) 0.007(7) -0.037(7) C87' 0.072(17) 0.070(14) 0.036(11) -0.031(9) 0.006(10) -0.041(12) C88' 0.034(7) 0.049(8) 0.031(8) -0.009(6) 0.010(6) -0.024(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N30 C29 1.507(7) . ? N30 C37 1.503(7) . ? N30 H30A 0.99 . ? N30 H30B 0.99 . ? N32 C31 1.496(7) . ? N32 C43 1.506(7) . ? N32 H32A 0.99 . ? N32 H32B 0.99 . ? N34 C33 1.510(7) . ? N34 C49 1.513(6) . ? N34 H34A 0.99 . ? N34 H34B 0.99 . ? N36 C35 1.496(6) . ? N36 C55 1.505(6) . ? N36 H36A 0.99 . ? N36 H36B 0.99 . ? O4 C4 1.382(6) . ? O4 H4 0.84 . ? O6 C6 1.384(6) . ? O6 H6 0.84 . ? O11 C11 1.374(6) . ? O11 H11 0.84 . ? O13 C13 1.371(6) . ? O13 H13 0.84 . ? O18 C18 1.359(6) . ? O18 H18 0.84 . ? O20 C20 1.376(6) . ? O20 H20 0.84 . ? O25 C25 1.377(6) . ? O25 H25 0.84 . ? O27 C27 1.384(6) . ? O27 H27 0.84 . ? C1 C2 1.387(7) . ? C1 C6 1.389(7) . ? C1 C28 1.535(7) . ? C2 C3 1.401(7) . ? C2 H2 0.95 . ? C3 C4 1.393(7) . ? C3 C7 1.532(7) . ? C4 C5 1.404(7) . ? C5 C6 1.400(7) . ? C5 C29 1.500(7) . ? C7 C8 1.532(6) . ? C7 C61 1.544(7) . ? C7 H7 1 . ? C8 C9 1.380(7) . ? C8 C13 1.405(7) . ? C9 C10 1.394(7) . ? C9 H9 0.95 . ? C10 C11 1.405(7) . ? C10 C14 1.518(7) . ? C11 C12 1.405(7) . ? C12 C13 1.396(7) . ? C12 C31 1.508(7) . ? C14 C15 1.525(7) . ? C14 C67 1.532(7) . ? C14 H14 1 . ? C15 C16 1.400(7) . ? C15 C20 1.397(7) . ? C16 C17 1.396(7) . ? C16 H16 0.95 . ? C17 C18 1.400(7) . ? C17 C21 1.516(6) . ? C18 C19 1.410(7) . ? C19 C20 1.399(7) . ? C19 C33 1.501(7) . ? C21 C22 1.527(7) . ? C21 C73 1.538(7) . ? C21 H21 1 . ? C22 C23 1.396(7) . ? C22 C27 1.398(7) . ? C23 C24 1.392(7) . ? C23 H23 0.95 . ? C24 C25 1.395(7) . ? C24 C28 1.526(7) . ? C25 C26 1.414(7) . ? C26 C27 1.394(7) . ? C26 C35 1.494(7) . ? C28 C79 1.527(7) . ? C28 H28 1 . ? C29 H29A 0.99 . ? C29 H29B 0.99 . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? C33 H33A 0.99 . ? C33 H33B 0.99 . ? C35 H35A 0.99 . ? C35 H35B 0.99 . ? C37 C42 1.521(8) . ? C37 C38 1.518(9) . ? C37 H37 1 . ? C38 C39 1.530(9) . ? C38 H38A 0.99 . ? C38 H38B 0.99 . ? C39 C40 1.513(10) . ? C39 H39A 0.99 . ? C39 H39B 0.99 . ? C40 C41 1.526(10) . ? C40 H40A 0.99 . ? C40 H40B 0.99 . ? C41 C42 1.530(9) . ? C41 H41A 0.99 . ? C41 H41B 0.99 . ? C42 H42A 0.99 . ? C42 H42B 0.99 . ? C43 C44 1.496(12) . ? C43 C48 1.507(8) . ? C43 H43 1 . ? C44 C45 1.534(13) . ? C44 H44A 0.99 . ? C44 H44B 0.99 . ? C45 C46 1.494(19) . ? C45 H45A 0.99 . ? C45 H45B 0.99 . ? C46 C47 1.479(19) . ? C46 H46A 0.99 . ? C46 H46B 0.99 . ? C47 C48 1.503(18) . ? C47 H47A 0.99 . ? C47 H47B 0.99 . ? C48 H48A 0.99 . ? C48 H48B 0.99 . ? C49 C54 1.506(8) . ? C49 C50 1.519(8) . ? C49 H49 1 . ? C50 C51 1.538(8) . ? C50 H50A 0.99 . ? C50 H50B 0.99 . ? C51 C52 1.521(10) . ? C51 H51A 0.99 . ? C51 H51B 0.99 . ? C52 C53 1.535(12) . ? C52 H52A 0.99 . ? C52 H52B 0.99 . ? C53 C54 1.517(7) . ? C53 H53A 0.99 . ? C53 H53B 0.99 . ? C54 H54A 0.99 . ? C54 H54B 0.99 . ? C55 C60 1.512(8) . ? C55 C56 1.523(7) . ? C55 H55 1 . ? C56 C57 1.530(8) . ? C56 H56A 0.99 . ? C56 H56B 0.99 . ? C57 C58 1.518(10) . ? C57 H57A 0.99 . ? C57 H57B 0.99 . ? C58 C59 1.527(9) . ? C58 H58A 0.99 . ? C58 H58B 0.99 . ? C59 C60 1.530(8) . ? C59 H59A 0.99 . ? C59 H59B 0.99 . ? C60 H60A 0.99 . ? C60 H60B 0.99 . ? C61 C62 1.489(4) . ? C61 H61A 0.99 . ? C61 H61B 0.99 . ? C62 C63 1.533(5) . ? C62 H62A 0.99 . ? C62 H62B 0.99 . ? C63 C64 1.531(13) . ? C63 H63A 0.99 . ? C63 H63B 0.99 . ? C64 C65 1.518(14) . ? C64 H64A 0.99 . ? C64 H64B 0.99 . ? C65 C66 1.503(15) . ? C65 H65C 0.99 . ? C65 H65D 0.99 . ? C66 H66A 0.98 . ? C66 H66B 0.98 . ? C66 H66C 0.98 . ? C67 C68 1.505(8) . ? C67 H67A 0.99 . ? C67 H67B 0.99 . ? C68 C69 1.538(10) . ? C68 H68A 0.99 . ? C68 H68B 0.99 . ? C69 C70 1.488(12) . ? C69 H69A 0.99 . ? C69 H69B 0.99 . ? C70 C71 1.508(8) . ? C70 H70A 0.99 . ? C70 H70B 0.99 . ? C71 C72 1.502(9) . ? C71 H71A 0.99 . ? C71 H71B 0.99 . ? C72 H72A 0.98 . ? C72 H72B 0.98 . ? C72 H72C 0.98 . ? C73 C74 1.529(8) . ? C73 H73A 0.99 . ? C73 H73B 0.99 . ? C74 C75 1.486(7) . ? C74 H74A 0.99 . ? C74 H74B 0.99 . ? C75 C76 1.506(8) . ? C75 H75A 0.99 . ? C75 H75B 0.99 . ? C76 C77 1.487(17) . ? C76 H76A 0.99 . ? C76 H76B 0.99 . ? C77 C78 1.50(2) . ? C77 H77A 0.99 . ? C77 H77B 0.99 . ? C78 H78A 0.98 . ? C78 H78B 0.98 . ? C78 H78C 0.98 . ? C79 C80 1.521(7) . ? C79 H79A 0.99 . ? C79 H79B 0.99 . ? C80 C81 1.517(8) . ? C80 H80A 0.99 . ? C80 H80B 0.99 . ? C81 C82 1.514(8) . ? C81 H81A 0.99 . ? C81 H81B 0.99 . ? C82 C83 1.521(8) . ? C82 H82A 0.99 . ? C82 H82B 0.99 . ? C83 C84 1.527(9) . ? C83 H83A 0.99 . ? C83 H83B 0.99 . ? C84 H84A 0.98 . ? C84 H84B 0.98 . ? C84 H84C 0.98 . ? O1 C88 1.419(8) . ? O1 C85 1.417(9) . ? O2 C86 1.397(8) . ? O2 C87 1.405(8) . ? C85 C86 1.493(9) . ? C85 H85A 0.99 . ? C85 H85B 0.99 . ? C86 H86A 0.99 . ? C86 H86B 0.99 . ? C87 C88 1.493(9) . ? C87 H87A 0.99 . ? C87 H87B 0.99 . ? C88 H88A 0.99 . ? C88 H88B 0.99 . ? O1' C85' 1.405(9) . ? O1' C88' 1.401(10) . ? O2' C87' 1.400(9) . ? O2' C86' 1.395(9) . ? C85' C86' 1.503(10) . ? C85' H85C 0.99 . ? C85' H85D 0.99 . ? C86' H86C 0.99 . ? C86' H86D 0.99 . ? C87' C88' 1.490(10) . ? C87' H87C 0.99 . ? C87' H87D 0.99 . ? C88' H88C 0.99 . ? C88' H88D 0.99 . ? 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 C29 N30 C37 116.3(4) . . ? C29 N30 H30A 108.2 . . ? C37 N30 H30A 108.2 . . ? C29 N30 H30B 108.2 . . ? C37 N30 H30B 108.2 . . ? H30A N30 H30B 107.4 . . ? C31 N32 C43 112.2(5) . . ? C31 N32 H32A 109.2 . . ? C43 N32 H32A 109.2 . . ? C31 N32 H32B 109.2 . . ? C43 N32 H32B 109.2 . . ? H32A N32 H32B 107.9 . . ? C33 N34 C49 113.6(4) . . ? C33 N34 H34A 108.9 . . ? C49 N34 H34A 108.9 . . ? C33 N34 H34B 108.9 . . ? C49 N34 H34B 108.9 . . ? H34A N34 H34B 107.7 . . ? C35 N36 C55 113.8(4) . . ? C35 N36 H36A 108.8 . . ? C55 N36 H36A 108.8 . . ? C35 N36 H36B 108.8 . . ? C55 N36 H36B 108.8 . . ? H36A N36 H36B 107.7 . . ? C4 O4 H4 109.5 . . ? C6 O6 H6 109.5 . . ? C11 O11 H11 109.5 . . ? C13 O13 H13 109.5 . . ? C18 O18 H18 109.5 . . ? C20 O20 H20 109.5 . . ? C25 O25 H25 109.5 . . ? C27 O27 H27 109.5 . . ? C2 C1 C6 117.9(4) . . ? C2 C1 C28 122.9(4) . . ? C6 C1 C28 119.1(4) . . ? C1 C2 C3 122.7(5) . . ? C1 C2 H2 118.7 . . ? C3 C2 H2 118.7 . . ? C2 C3 C4 117.6(4) . . ? C2 C3 C7 122.6(5) . . ? C4 C3 C7 119.8(4) . . ? O4 C4 C3 117.6(4) . . ? O4 C4 C5 120.5(5) . . ? C3 C4 C5 121.8(4) . . ? C4 C5 C6 117.9(5) . . ? C4 C5 C29 121.5(4) . . ? C6 C5 C29 120.6(4) . . ? O6 C6 C1 117.3(4) . . ? O6 C6 C5 120.5(4) . . ? C1 C6 C5 122.1(4) . . ? C3 C7 C8 109.3(4) . . ? C3 C7 C61 114.1(4) . . ? C8 C7 C61 112.8(4) . . ? C3 C7 H7 106.7 . . ? C8 C7 H7 106.7 . . ? C61 C7 H7 106.7 . . ? C9 C8 C13 117.2(4) . . ? C9 C8 C7 121.6(4) . . ? C13 C8 C7 121.1(4) . . ? C8 C9 C10 123.9(5) . . ? C8 C9 H9 118 . . ? C10 C9 H9 118 . . ? C9 C10 C11 117.4(5) . . ? C9 C10 C14 121.9(4) . . ? C11 C10 C14 120.6(4) . . ? O11 C11 C10 118.2(5) . . ? O11 C11 C12 121.1(4) . . ? C10 C11 C12 120.7(4) . . ? C13 C12 C11 119.1(4) . . ? C13 C12 C31 119.0(5) . . ? C11 C12 C31 121.8(4) . . ? O13 C13 C12 115.8(4) . . ? O13 C13 C8 122.8(4) . . ? C12 C13 C8 121.5(5) . . ? C10 C14 C15 110.7(4) . . ? C10 C14 C67 112.0(4) . . ? C15 C14 C67 114.3(4) . . ? C10 C14 H14 106.4 . . ? C15 C14 H14 106.4 . . ? C67 C14 H14 106.4 . . ? C16 C15 C20 116.2(4) . . ? C16 C15 C14 122.0(4) . . ? C20 C15 C14 121.7(4) . . ? C15 C16 C17 123.9(4) . . ? C15 C16 H16 118.1 . . ? C17 C16 H16 118.1 . . ? C18 C17 C16 118.0(4) . . ? C18 C17 C21 120.3(4) . . ? C16 C17 C21 121.6(4) . . ? O18 C18 C17 123.2(4) . . ? O18 C18 C19 116.5(4) . . ? C17 C18 C19 120.3(4) . . ? C20 C19 C18 119.0(4) . . ? C20 C19 C33 119.9(4) . . ? C18 C19 C33 121.0(4) . . ? O20 C20 C19 114.7(4) . . ? O20 C20 C15 122.8(4) . . ? C19 C20 C15 122.5(4) . . ? C17 C21 C22 113.6(4) . . ? C17 C21 C73 113.0(4) . . ? C22 C21 C73 111.7(4) . . ? C17 C21 H21 105.9 . . ? C22 C21 H21 105.9 . . ? C73 C21 H21 105.9 . . ? C23 C22 C27 116.9(4) . . ? C23 C22 C21 121.2(4) . . ? C27 C22 C21 121.8(4) . . ? C24 C23 C22 124.0(5) . . ? C24 C23 H23 118 . . ? C22 C23 H23 118 . . ? C23 C24 C25 116.9(4) . . ? C23 C24 C28 120.5(4) . . ? C25 C24 C28 122.6(4) . . ? O25 C25 C24 123.9(4) . . ? O25 C25 C26 114.5(4) . . ? C24 C25 C26 121.6(4) . . ? C27 C26 C25 118.5(4) . . ? C27 C26 C35 123.9(4) . . ? C25 C26 C35 117.4(4) . . ? C26 C27 O27 121.6(4) . . ? C26 C27 C22 121.7(4) . . ? O27 C27 C22 116.7(4) . . ? C79 C28 C24 110.7(4) . . ? C79 C28 C1 115.3(4) . . ? C24 C28 C1 109.1(4) . . ? C79 C28 H28 107.1 . . ? C24 C28 H28 107.1 . . ? C1 C28 H28 107.1 . . ? C5 C29 N30 111.4(4) . . ? C5 C29 H29A 109.3 . . ? N30 C29 H29A 109.3 . . ? C5 C29 H29B 109.3 . . ? N30 C29 H29B 109.3 . . ? H29A C29 H29B 108 . . ? N32 C31 C12 112.8(4) . . ? N32 C31 H31A 109 . . ? C12 C31 H31A 109 . . ? N32 C31 H31B 109 . . ? C12 C31 H31B 109 . . ? H31A C31 H31B 107.8 . . ? C19 C33 N34 111.2(4) . . ? C19 C33 H33A 109.4 . . ? N34 C33 H33A 109.4 . . ? C19 C33 H33B 109.4 . . ? N34 C33 H33B 109.4 . . ? H33A C33 H33B 108 . . ? C26 C35 N36 113.4(4) . . ? C26 C35 H35A 108.9 . . ? N36 C35 H35A 108.9 . . ? C26 C35 H35B 108.9 . . ? N36 C35 H35B 108.9 . . ? H35A C35 H35B 107.7 . . ? N30 C37 C42 111.8(4) . . ? N30 C37 C38 107.3(5) . . ? C42 C37 C38 111.7(5) . . ? N30 C37 H37 108.6 . . ? C42 C37 H37 108.6 . . ? C38 C37 H37 108.6 . . ? C37 C38 C39 111.5(6) . . ? C37 C38 H38A 109.3 . . ? C39 C38 H38A 109.3 . . ? C37 C38 H38B 109.3 . . ? C39 C38 H38B 109.3 . . ? H38A C38 H38B 108 . . ? C40 C39 C38 110.8(6) . . ? C40 C39 H39A 109.5 . . ? C38 C39 H39A 109.5 . . ? C40 C39 H39B 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 108.1 . . ? C39 C40 C41 110.4(6) . . ? C39 C40 H40A 109.6 . . ? C41 C40 H40A 109.6 . . ? C39 C40 H40B 109.6 . . ? C41 C40 H40B 109.6 . . ? H40A C40 H40B 108.1 . . ? C40 C41 C42 110.8(5) . . ? C40 C41 H41A 109.5 . . ? C42 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? C42 C41 H41B 109.5 . . ? H41A C41 H41B 108.1 . . ? C37 C42 C41 109.5(5) . . ? C37 C42 H42A 109.8 . . ? C41 C42 H42A 109.8 . . ? C37 C42 H42B 109.8 . . ? C41 C42 H42B 109.8 . . ? H42A C42 H42B 108.2 . . ? C44 C43 N32 113.2(7) . . ? C44 C43 C48 113.0(8) . . ? N32 C43 C48 110.9(6) . . ? C44 C43 H43 106.4 . . ? N32 C43 H43 106.4 . . ? C48 C43 H43 106.4 . . ? C43 C44 C45 110.0(9) . . ? C43 C44 H44A 109.7 . . ? C45 C44 H44A 109.7 . . ? C43 C44 H44B 109.7 . . ? C45 C44 H44B 109.7 . . ? H44A C44 H44B 108.2 . . ? C46 C45 C44 111.4(10) . . ? C46 C45 H45A 109.3 . . ? C44 C45 H45A 109.3 . . ? C46 C45 H45B 109.3 . . ? C44 C45 H45B 109.3 . . ? H45A C45 H45B 108 . . ? C47 C46 C45 110.6(11) . . ? C47 C46 H46A 109.5 . . ? C45 C46 H46A 109.5 . . ? C47 C46 H46B 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 108.1 . . ? C46 C47 C48 109.3(10) . . ? C46 C47 H47A 109.8 . . ? C48 C47 H47A 109.8 . . ? C46 C47 H47B 109.8 . . ? C48 C47 H47B 109.8 . . ? H47A C47 H47B 108.3 . . ? C43 C48 C47 113.2(9) . . ? C43 C48 H48A 108.9 . . ? C47 C48 H48A 108.9 . . ? C43 C48 H48B 108.9 . . ? C47 C48 H48B 108.9 . . ? H48A C48 H48B 107.8 . . ? C54 C49 C50 111.0(5) . . ? C54 C49 N34 110.6(4) . . ? C50 C49 N34 108.2(4) . . ? C54 C49 H49 109 . . ? C50 C49 H49 109 . . ? N34 C49 H49 109 . . ? C49 C50 C51 111.4(5) . . ? C49 C50 H50A 109.4 . . ? C51 C50 H50A 109.4 . . ? C49 C50 H50B 109.4 . . ? C51 C50 H50B 109.4 . . ? H50A C50 H50B 108 . . ? C52 C51 C50 109.9(6) . . ? C52 C51 H51A 109.7 . . ? C50 C51 H51A 109.7 . . ? C52 C51 H51B 109.7 . . ? C50 C51 H51B 109.7 . . ? H51A C51 H51B 108.2 . . ? C51 C52 C53 110.9(6) . . ? C51 C52 H52A 109.5 . . ? C53 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? C53 C52 H52B 109.5 . . ? H52A C52 H52B 108 . . ? C52 C53 C54 111.5(6) . . ? C52 C53 H53A 109.3 . . ? C54 C53 H53A 109.3 . . ? C52 C53 H53B 109.3 . . ? C54 C53 H53B 109.3 . . ? H53A C53 H53B 108 . . ? C49 C54 C53 110.8(5) . . ? C49 C54 H54A 109.5 . . ? C53 C54 H54A 109.5 . . ? C49 C54 H54B 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 108.1 . . ? N36 C55 C60 109.4(4) . . ? N36 C55 C56 112.0(4) . . ? C60 C55 C56 111.3(4) . . ? N36 C55 H55 108 . . ? C60 C55 H55 108 . . ? C56 C55 H55 108 . . ? C55 C56 C57 109.6(4) . . ? C55 C56 H56A 109.8 . . ? C57 C56 H56A 109.8 . . ? C55 C56 H56B 109.8 . . ? C57 C56 H56B 109.8 . . ? H56A C56 H56B 108.2 . . ? C58 C57 C56 111.7(5) . . ? C58 C57 H57A 109.3 . . ? C56 C57 H57A 109.3 . . ? C58 C57 H57B 109.3 . . ? C56 C57 H57B 109.3 . . ? H57A C57 H57B 107.9 . . ? C59 C58 C57 111.6(5) . . ? C59 C58 H58A 109.3 . . ? C57 C58 H58A 109.3 . . ? C59 C58 H58B 109.3 . . ? C57 C58 H58B 109.3 . . ? H58A C58 H58B 108 . . ? C58 C59 C60 110.8(5) . . ? C58 C59 H59A 109.5 . . ? C60 C59 H59A 109.5 . . ? C58 C59 H59B 109.5 . . ? C60 C59 H59B 109.5 . . ? H59A C59 H59B 108.1 . . ? C55 C60 C59 110.1(5) . . ? C55 C60 H60A 109.6 . . ? C59 C60 H60A 109.6 . . ? C55 C60 H60B 109.6 . . ? C59 C60 H60B 109.6 . . ? H60A C60 H60B 108.2 . . ? C62 C61 C7 115.4(4) . . ? C62 C61 H61A 108.4 . . ? C7 C61 H61A 108.4 . . ? C62 C61 H61B 108.4 . . ? C7 C61 H61B 108.4 . . ? H61A C61 H61B 107.5 . . ? C63 C62 C61 112.7(5) . . ? C63 C62 H62A 109.1 . . ? C61 C62 H62A 109.1 . . ? C63 C62 H62B 109.1 . . ? C61 C62 H62B 109.1 . . ? H62A C62 H62B 107.8 . . ? C62 C63 C64 111.0(7) . . ? C62 C63 H63A 109.4 . . ? C64 C63 H63A 109.4 . . ? C62 C63 H63B 109.4 . . ? C64 C63 H63B 109.4 . . ? H63A C63 H63B 108 . . ? C63 C64 C65 113.1(8) . . ? C63 C64 H64A 109 . . ? C65 C64 H64A 109 . . ? C63 C64 H64B 109 . . ? C65 C64 H64B 109 . . ? H64A C64 H64B 107.8 . . ? C66 C65 C64 113.8(5) . . ? C66 C65 H65C 108.8 . . ? C64 C65 H65C 108.8 . . ? C66 C65 H65D 108.8 . . ? C64 C65 H65D 108.8 . . ? H65C C65 H65D 107.7 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C68 C67 C14 113.7(5) . . ? C68 C67 H67A 108.8 . . ? C14 C67 H67A 108.8 . . ? C68 C67 H67B 108.8 . . ? C14 C67 H67B 108.8 . . ? H67A C67 H67B 107.7 . . ? C67 C68 C69 114.1(6) . . ? C67 C68 H68A 108.7 . . ? C69 C68 H68A 108.7 . . ? C67 C68 H68B 108.7 . . ? C69 C68 H68B 108.7 . . ? H68A C68 H68B 107.6 . . ? C70 C69 C68 114.3(6) . . ? C70 C69 H69A 108.7 . . ? C68 C69 H69A 108.7 . . ? C70 C69 H69B 108.7 . . ? C68 C69 H69B 108.7 . . ? H69A C69 H69B 107.6 . . ? C69 C70 C71 115.9(8) . . ? C69 C70 H70A 108.3 . . ? C71 C70 H70A 108.3 . . ? C69 C70 H70B 108.3 . . ? C71 C70 H70B 108.3 . . ? H70A C70 H70B 107.4 . . ? C72 C71 C70 105.9(9) . . ? C72 C71 H71A 110.6 . . ? C70 C71 H71A 110.6 . . ? C72 C71 H71B 110.6 . . ? C70 C71 H71B 110.6 . . ? H71A C71 H71B 108.7 . . ? C71 C72 H72A 109.5 . . ? C71 C72 H72B 109.5 . . ? H72A C72 H72B 109.5 . . ? C71 C72 H72C 109.5 . . ? H72A C72 H72C 109.5 . . ? H72B C72 H72C 109.5 . . ? C74 C73 C21 111.9(4) . . ? C74 C73 H73A 109.2 . . ? C21 C73 H73A 109.2 . . ? C74 C73 H73B 109.2 . . ? C21 C73 H73B 109.2 . . ? H73A C73 H73B 107.9 . . ? C75 C74 C73 116.8(6) . . ? C75 C74 H74A 108.1 . . ? C73 C74 H74A 108.1 . . ? C75 C74 H74B 108.1 . . ? C73 C74 H74B 108.1 . . ? H74A C74 H74B 107.3 . . ? C74 C75 C76 117.4(7) . . ? C74 C75 H75A 108 . . ? C76 C75 H75A 108 . . ? C74 C75 H75B 108 . . ? C76 C75 H75B 108 . . ? H75A C75 H75B 107.2 . . ? C77 C76 C75 116.7(11) . . ? C77 C76 H76A 108.1 . . ? C75 C76 H76A 108.1 . . ? C77 C76 H76B 108.1 . . ? C75 C76 H76B 108.1 . . ? H76A C76 H76B 107.3 . . ? C76 C77 C78 112.9(13) . . ? C76 C77 H77A 109 . . ? C78 C77 H77A 109 . . ? C76 C77 H77B 109 . . ? C78 C77 H77B 109 . . ? H77A C77 H77B 107.8 . . ? C77 C78 H78A 109.5 . . ? C77 C78 H78B 109.5 . . ? H78A C78 H78B 109.5 . . ? C77 C78 H78C 109.5 . . ? H78A C78 H78C 109.5 . . ? H78B C78 H78C 109.5 . . ? C80 C79 C28 115.2(4) . . ? C80 C79 H79A 108.5 . . ? C28 C79 H79A 108.5 . . ? C80 C79 H79B 108.5 . . ? C28 C79 H79B 108.5 . . ? H79A C79 H79B 107.5 . . ? C79 C80 C81 112.9(5) . . ? C79 C80 H80A 109 . . ? C81 C80 H80A 109 . . ? C79 C80 H80B 109 . . ? C81 C80 H80B 109 . . ? H80A C80 H80B 107.8 . . ? C82 C81 C80 114.5(5) . . ? C82 C81 H81A 108.6 . . ? C80 C81 H81A 108.6 . . ? C82 C81 H81B 108.6 . . ? C80 C81 H81B 108.6 . . ? H81A C81 H81B 107.6 . . ? C81 C82 C83 113.1(5) . . ? C81 C82 H82A 109 . . ? C83 C82 H82A 109 . . ? C81 C82 H82B 109 . . ? C83 C82 H82B 109 . . ? H82A C82 H82B 107.8 . . ? C84 C83 C82 112.4(5) . . ? C84 C83 H83A 109.1 . . ? C82 C83 H83A 109.1 . . ? C84 C83 H83B 109.1 . . ? C82 C83 H83B 109.1 . . ? H83A C83 H83B 107.9 . . ? C83 C84 H84A 109.5 . . ? C83 C84 H84B 109.5 . . ? H84A C84 H84B 109.5 . . ? C83 C84 H84C 109.5 . . ? H84A C84 H84C 109.5 . . ? H84B C84 H84C 109.5 . . ? C88 O1 C85 110.7(9) . . ? C86 O2 C87 108.8(10) . . ? O1 C85 C86 111.3(9) . . ? O1 C85 H85A 109.4 . . ? C86 C85 H85A 109.4 . . ? O1 C85 H85B 109.4 . . ? C86 C85 H85B 109.4 . . ? H85A C85 H85B 108 . . ? O2 C86 C85 109.7(8) . . ? O2 C86 H86A 109.7 . . ? C85 C86 H86A 109.7 . . ? O2 C86 H86B 109.7 . . ? C85 C86 H86B 109.7 . . ? H86A C86 H86B 108.2 . . ? O2 C87 C88 112.5(9) . . ? O2 C87 H87A 109.1 . . ? C88 C87 H87A 109.1 . . ? O2 C87 H87B 109.1 . . ? C88 C87 H87B 109.1 . . ? H87A C87 H87B 107.8 . . ? O1 C88 C87 109.6(10) . . ? O1 C88 H88A 109.8 . . ? C87 C88 H88A 109.8 . . ? O1 C88 H88B 109.8 . . ? C87 C88 H88B 109.8 . . ? H88A C88 H88B 108.2 . . ? C85' O1' C88' 109.5(14) . . ? C87' O2' C86' 109.8(14) . . ? O1' C85' C86' 111.5(15) . . ? O1' C85' H85C 109.3 . . ? C86' C85' H85C 109.3 . . ? O1' C85' H85D 109.3 . . ? C86' C85' H85D 109.3 . . ? H85C C85' H85D 108 . . ? O2' C86' C85' 111.3(13) . . ? O2' C86' H86C 109.4 . . ? C85' C86' H86C 109.4 . . ? O2' C86' H86D 109.4 . . ? C85' C86' H86D 109.4 . . ? H86C C86' H86D 108 . . ? O2' C87' C88' 110.0(14) . . ? O2' C87' H87C 109.7 . . ? C88' C87' H87C 109.7 . . ? O2' C87' H87D 109.7 . . ? C88' C87' H87D 109.7 . . ? H87C C87' H87D 108.2 . . ? O1' C88' C87' 112.4(14) . . ? O1' C88' H88C 109.1 . . ? C87' C88' H88C 109.1 . . ? O1' C88' H88D 109.1 . . ? C87' C88' H88D 109.1 . . ? H88C C88' H88D 107.9 . . ? 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 C6 C1 C2 C3 0.7(7) . . . . ? C28 C1 C2 C3 177.9(4) . . . . ? C1 C2 C3 C4 -0.2(7) . . . . ? C1 C2 C3 C7 179.6(4) . . . . ? C2 C3 C4 O4 175.9(4) . . . . ? C7 C3 C4 O4 -4.0(7) . . . . ? C2 C3 C4 C5 -0.4(7) . . . . ? C7 C3 C4 C5 179.7(4) . . . . ? O4 C4 C5 C6 -175.6(4) . . . . ? C3 C4 C5 C6 0.6(7) . . . . ? O4 C4 C5 C29 2.3(7) . . . . ? C3 C4 C5 C29 178.5(4) . . . . ? C2 C1 C6 O6 -177.2(4) . . . . ? C28 C1 C6 O6 5.5(6) . . . . ? C2 C1 C6 C5 -0.5(7) . . . . ? C28 C1 C6 C5 -177.9(4) . . . . ? C4 C5 C6 O6 176.5(4) . . . . ? C29 C5 C6 O6 -1.5(7) . . . . ? C4 C5 C6 C1 -0.1(7) . . . . ? C29 C5 C6 C1 -178.1(4) . . . . ? C2 C3 C7 C8 98.8(5) . . . . ? C4 C3 C7 C8 -81.3(6) . . . . ? C2 C3 C7 C61 -28.5(7) . . . . ? C4 C3 C7 C61 151.3(5) . . . . ? C3 C7 C8 C9 -79.9(6) . . . . ? C61 C7 C8 C9 48.1(6) . . . . ? C3 C7 C8 C13 100.8(5) . . . . ? C61 C7 C8 C13 -131.1(5) . . . . ? C13 C8 C9 C10 -1.5(7) . . . . ? C7 C8 C9 C10 179.2(4) . . . . ? C8 C9 C10 C11 -2.0(7) . . . . ? C8 C9 C10 C14 178.1(4) . . . . ? C9 C10 C11 O11 -177.6(4) . . . . ? C14 C10 C11 O11 2.3(7) . . . . ? C9 C10 C11 C12 4.5(7) . . . . ? C14 C10 C11 C12 -175.6(4) . . . . ? O11 C11 C12 C13 178.6(4) . . . . ? C10 C11 C12 C13 -3.6(7) . . . . ? O11 C11 C12 C31 -4.9(7) . . . . ? C10 C11 C12 C31 172.8(5) . . . . ? C11 C12 C13 O13 -179.9(4) . . . . ? C31 C12 C13 O13 3.5(7) . . . . ? C11 C12 C13 C8 0.0(7) . . . . ? C31 C12 C13 C8 -176.5(5) . . . . ? C9 C8 C13 O13 -177.6(4) . . . . ? C7 C8 C13 O13 1.7(7) . . . . ? C9 C8 C13 C12 2.5(7) . . . . ? C7 C8 C13 C12 -178.2(4) . . . . ? C9 C10 C14 C15 86.5(5) . . . . ? C11 C10 C14 C15 -93.4(5) . . . . ? C9 C10 C14 C67 -42.2(6) . . . . ? C11 C10 C14 C67 137.8(5) . . . . ? C10 C14 C15 C16 -88.5(5) . . . . ? C67 C14 C15 C16 39.1(6) . . . . ? C10 C14 C15 C20 89.5(5) . . . . ? C67 C14 C15 C20 -143.0(5) . . . . ? C20 C15 C16 C17 -1.2(7) . . . . ? C14 C15 C16 C17 176.9(4) . . . . ? C15 C16 C17 C18 -2.9(7) . . . . ? C15 C16 C17 C21 174.4(4) . . . . ? C16 C17 C18 O18 -176.8(4) . . . . ? C21 C17 C18 O18 5.9(7) . . . . ? C16 C17 C18 C19 5.0(7) . . . . ? C21 C17 C18 C19 -172.4(4) . . . . ? O18 C18 C19 C20 178.7(4) . . . . ? C17 C18 C19 C20 -3.0(7) . . . . ? O18 C18 C19 C33 -4.1(7) . . . . ? C17 C18 C19 C33 174.2(5) . . . . ? C18 C19 C20 O20 178.4(4) . . . . ? C33 C19 C20 O20 1.1(7) . . . . ? C18 C19 C20 C15 -1.4(7) . . . . ? C33 C19 C20 C15 -178.6(5) . . . . ? C16 C15 C20 O20 -176.3(4) . . . . ? C14 C15 C20 O20 5.6(7) . . . . ? C16 C15 C20 C19 3.4(7) . . . . ? C14 C15 C20 C19 -174.7(4) . . . . ? C18 C17 C21 C22 -89.2(5) . . . . ? C16 C17 C21 C22 93.5(5) . . . . ? C18 C17 C21 C73 142.2(5) . . . . ? C16 C17 C21 C73 -35.1(6) . . . . ? C17 C21 C22 C23 -78.3(6) . . . . ? C73 C21 C22 C23 51.0(6) . . . . ? C17 C21 C22 C27 103.2(5) . . . . ? C73 C21 C22 C27 -127.6(5) . . . . ? C27 C22 C23 C24 5.4(7) . . . . ? C21 C22 C23 C24 -173.2(4) . . . . ? C22 C23 C24 C25 -0.7(7) . . . . ? C22 C23 C24 C28 178.3(4) . . . . ? C23 C24 C25 O25 176.2(4) . . . . ? C28 C24 C25 O25 -2.8(7) . . . . ? C23 C24 C25 C26 -1.9(7) . . . . ? C28 C24 C25 C26 179.1(4) . . . . ? O25 C25 C26 C27 -178.6(4) . . . . ? C24 C25 C26 C27 -0.2(7) . . . . ? O25 C25 C26 C35 -3.5(6) . . . . ? C24 C25 C26 C35 174.8(4) . . . . ? C25 C26 C27 O27 -176.8(4) . . . . ? C35 C26 C27 O27 8.5(7) . . . . ? C25 C26 C27 C22 5.3(7) . . . . ? C35 C26 C27 C22 -169.4(5) . . . . ? C23 C22 C27 C26 -7.7(7) . . . . ? C21 C22 C27 C26 171.0(4) . . . . ? C23 C22 C27 O27 174.3(4) . . . . ? C21 C22 C27 O27 -7.1(7) . . . . ? C23 C24 C28 C79 -53.6(6) . . . . ? C25 C24 C28 C79 125.4(5) . . . . ? C23 C24 C28 C1 74.2(5) . . . . ? C25 C24 C28 C1 -106.8(5) . . . . ? C2 C1 C28 C79 24.7(6) . . . . ? C6 C1 C28 C79 -158.1(4) . . . . ? C2 C1 C28 C24 -100.6(5) . . . . ? C6 C1 C28 C24 76.6(5) . . . . ? C4 C5 C29 N30 95.3(5) . . . . ? C6 C5 C29 N30 -86.8(5) . . . . ? C37 N30 C29 C5 -172.7(4) . . . . ? C43 N32 C31 C12 166.8(6) . . . . ? C13 C12 C31 N32 -79.4(6) . . . . ? C11 C12 C31 N32 104.2(6) . . . . ? C20 C19 C33 N34 -60.0(6) . . . . ? C18 C19 C33 N34 122.8(5) . . . . ? C49 N34 C33 C19 166.3(4) . . . . ? C27 C26 C35 N36 -105.6(5) . . . . ? C25 C26 C35 N36 79.6(5) . . . . ? C55 N36 C35 C26 -166.9(4) . . . . ? C29 N30 C37 C42 -57.7(6) . . . . ? C29 N30 C37 C38 179.5(5) . . . . ? N30 C37 C38 C39 177.9(5) . . . . ? C42 C37 C38 C39 55.1(7) . . . . ? C37 C38 C39 C40 -54.9(8) . . . . ? C38 C39 C40 C41 56.6(8) . . . . ? C39 C40 C41 C42 -58.8(7) . . . . ? N30 C37 C42 C41 -176.4(5) . . . . ? C38 C37 C42 C41 -56.2(7) . . . . ? C40 C41 C42 C37 58.0(7) . . . . ? C31 N32 C43 C44 57.0(9) . . . . ? C31 N32 C43 C48 -174.8(8) . . . . ? N32 C43 C44 C45 176.8(8) . . . . ? C48 C43 C44 C45 49.6(12) . . . . ? C43 C44 C45 C46 -54.4(13) . . . . ? C44 C45 C46 C47 60.4(15) . . . . ? C45 C46 C47 C48 -59.5(16) . . . . ? C44 C43 C48 C47 -51.5(14) . . . . ? N32 C43 C48 C47 -179.9(9) . . . . ? C46 C47 C48 C43 55.2(16) . . . . ? C33 N34 C49 C54 159.4(5) . . . . ? C33 N34 C49 C50 -78.8(6) . . . . ? C54 C49 C50 C51 -57.1(7) . . . . ? N34 C49 C50 C51 -178.7(5) . . . . ? C49 C50 C51 C52 56.3(8) . . . . ? C50 C51 C52 C53 -55.3(8) . . . . ? C51 C52 C53 C54 56.0(9) . . . . ? C50 C49 C54 C53 56.6(8) . . . . ? N34 C49 C54 C53 176.8(6) . . . . ? C52 C53 C54 C49 -56.2(9) . . . . ? C35 N36 C55 C60 -165.3(4) . . . . ? C35 N36 C55 C56 70.8(5) . . . . ? N36 C55 C56 C57 -178.8(5) . . . . ? C60 C55 C56 C57 58.4(6) . . . . ? C55 C56 C57 C58 -55.7(6) . . . . ? C56 C57 C58 C59 54.5(7) . . . . ? C57 C58 C59 C60 -54.4(7) . . . . ? N36 C55 C60 C59 176.6(4) . . . . ? C56 C55 C60 C59 -59.1(6) . . . . ? C58 C59 C60 C55 56.4(7) . . . . ? C3 C7 C61 C62 -169.3(5) . . . . ? C8 C7 C61 C62 65.2(6) . . . . ? C7 C61 C62 C63 51.9(8) . . . . ? C61 C62 C63 C64 145.8(6) . . . . ? C62 C63 C64 C65 68.2(10) . . . . ? C63 C64 C65 C66 176.0(10) . . . . ? C10 C14 C67 C68 -162.3(5) . . . . ? C15 C14 C67 C68 70.8(6) . . . . ? C14 C67 C68 C69 -177.6(5) . . . . ? C67 C68 C69 C70 -64.9(9) . . . . ? C68 C69 C70 C71 -158.2(8) . . . . ? C69 C70 C71 C72 -71.2(12) . . . . ? C17 C21 C73 C74 -169.9(5) . . . . ? C22 C21 C73 C74 60.6(6) . . . . ? C21 C73 C74 C75 167.9(6) . . . . ? C73 C74 C75 C76 59.3(12) . . . . ? C74 C75 C76 C77 66.5(14) . . . . ? C75 C76 C77 C78 75.3(15) . . . . ? C24 C28 C79 C80 -175.0(4) . . . . ? C1 C28 C79 C80 60.6(6) . . . . ? C28 C79 C80 C81 171.3(4) . . . . ? C79 C80 C81 C82 172.0(5) . . . . ? C80 C81 C82 C83 174.6(5) . . . . ? C81 C82 C83 C84 173.2(5) . . . . ? C88 O1 C85 C86 56.1(15) . . . . ? C87 O2 C86 C85 59.6(13) . . . . ? O1 C85 C86 O2 -59.1(15) . . . . ? C86 O2 C87 C88 -59.9(14) . . . . ? C85 O1 C88 C87 -53.7(15) . . . . ? O2 C87 C88 O1 56.7(15) . . . . ? C88' O1' C85' C86' 54.3(18) . . . . ? C87' O2' C86' C85' 58(2) . . . . ? O1' C85' C86' O2' -56(2) . . . . ? C86' O2' C87' C88' -58(2) . . . . ? C85' O1' C88' C87' -56(2) . . . . ? O2' C87' C88' O1' 58(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 967820' ####################################################################### # # 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_5_7_4.5 _audit_creation_date 2013-07-31T18:50:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_melting_point ? _chemical_formula_moiety 'C64 H72 N4 O8, 4.5(C Br Cl3), C H Cl3, 4(Cl), 1.5(O)' _chemical_formula_sum 'C69.50 H73 Br4.50 Cl20.50 N4 O9.50' _chemical_formula_weight 2202.63 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 15.6587(6) _cell_length_b 15.7044(6) _cell_length_c 20.3684(6) _cell_angle_alpha 92.294(3) _cell_angle_beta 110.286(3) _cell_angle_gamma 98.735(3) _cell_volume 4620.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123.0(1) _cell_measurement_reflns_used 12244 _cell_measurement_theta_min 3.516 _cell_measurement_theta_max 76.405 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.583 _exptl_crystal_F_000 2200 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 8.263 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.154 _exptl_absorpt_correction_T_max 0.636 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123.0(1) _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator mirror _diffrn_detector_area_resol_mean 10.3953 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_unetI/netI 0.0497 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_number 27133 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.057 _diffrn_reflns_theta_max 66.997 _diffrn_reflns_theta_full 67.684 _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_Laue_measured_fraction_full 0.975 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_point_group_measured_fraction_full 0.975 _diffrn_reflns_point_group_measured_fraction_max 0.990 _reflns_number_total 16316 _reflns_number_gt 12955 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlisPro, Agilent Technologies, 2013' _computing_cell_refinement 'CrysAlisPro, Agilent Technologies, 2013' _computing_data_reduction 'CrysAlisPro, Agilent Technologies, 2013' _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'MERCURY (Macrae et al., 2006)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 16316 _refine_ls_number_parameters 1119 _refine_ls_number_restraints 133 _refine_ls_R_factor_all 0.1560 _refine_ls_R_factor_gt 0.1389 _refine_ls_wR_factor_ref 0.4264 _refine_ls_wR_factor_gt 0.3954 _refine_ls_goodness_of_fit_ref 1.798 _refine_ls_restrained_S_all 1.814 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 4.379 _refine_diff_density_min -3.345 _refine_diff_density_rms 0.261 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group N30 N 0.4408(5) 0.2908(4) 0.4882(4) 0.0320(13) Uani 1 d . . H30A H 0.4507 0.3199 0.4486 0.038 Uiso 1 calc . . H30B H 0.3936 0.2379 0.4682 0.038 Uiso 1 calc . . N32 N 0.2305(5) 0.0108(4) 0.2390(4) 0.0388(16) Uani 1 d . . H32A H 0.1991 0.0197 0.1891 0.047 Uiso 1 calc . . H32B H 0.2658 0.0675 0.2643 0.047 Uiso 1 calc . . N34 N 0.1271(5) 0.1914(4) -0.0262(4) 0.0331(14) Uani 1 d . . H34A H 0.1536 0.2523 -0.0068 0.04 Uiso 1 calc . . H34B H 0.1471 0.1548 0.0128 0.04 Uiso 1 calc . . N36 N 0.4129(4) 0.4511(4) 0.2369(3) 0.0310(13) Uani 1 d . . H36A H 0.4314 0.4647 0.2884 0.037 Uiso 1 calc . . H36B H 0.3749 0.3923 0.2242 0.037 Uiso 1 calc . . O4 O 0.2652(5) 0.2153(4) 0.5026(3) 0.0390(13) Uani 1 d . . H4 H 0.2339 0.1693 0.4781 0.058 Uiso 1 calc . . O6 O 0.3499(4) 0.5057(3) 0.4584(3) 0.0329(12) Uani 1 d . . H6 H 0.3702 0.5255 0.5009 0.049 Uiso 1 calc . . O11 O 0.0242(5) 0.0086(3) 0.1533(3) 0.0423(14) Uani 1 d . . H11 H 0.0024 0.0337 0.1171 0.063 Uiso 1 calc . . O13 O 0.1805(5) 0.0828(4) 0.3982(3) 0.0397(13) Uani 1 d . . H13 H 0.2329 0.0951 0.395 0.06 Uiso 1 calc . . O18 O 0.0478(4) 0.3528(3) -0.0176(3) 0.0326(11) Uani 1 d . . H18 H 0.0824 0.3976 0.0069 0.049 Uiso 1 calc . . O20 O -0.0508(5) 0.0695(4) 0.0322(3) 0.0458(15) Uani 1 d . . H20 H -0.0917 0.0522 -0.0074 0.069 Uiso 1 calc . . O25 O 0.3432(4) 0.5377(3) 0.3274(3) 0.0294(11) Uani 1 d . . H25 H 0.3362 0.5516 0.3652 0.044 Uiso 1 calc . . O27 O 0.1791(4) 0.4656(3) 0.0832(2) 0.0270(10) Uani 1 d . . H27 H 0.2277 0.4484 0.0839 0.04 Uiso 1 calc . . C1 C 0.1958(6) 0.4336(4) 0.4002(4) 0.0266(14) Uani 1 d . . C2 C 0.1287(6) 0.3585(5) 0.3874(4) 0.0295(15) Uani 1 d . . H2 H 0.0685 0.3581 0.354 0.035 Uiso 1 calc . . C3 C 0.1471(6) 0.2840(5) 0.4219(4) 0.0321(16) Uani 1 d . . C4 C 0.2376(6) 0.2851(5) 0.4677(4) 0.0327(16) Uani 1 d . . C5 C 0.3078(6) 0.3580(5) 0.4816(4) 0.0301(15) Uani 1 d . . C6 C 0.2849(6) 0.4317(4) 0.4484(4) 0.0266(14) Uani 1 d . . C7 C 0.0711(6) 0.2050(5) 0.4072(5) 0.0357(17) Uani 1 d . . H7 H 0.0942 0.1667 0.4452 0.043 Uiso 1 calc . . C8 C 0.0554(6) 0.1530(4) 0.3383(5) 0.0331(16) Uani 1 d . . C9 C -0.0129(6) 0.1635(5) 0.2760(5) 0.0351(17) Uani 1 d . . H9 H -0.0523 0.2034 0.2773 0.042 Uiso 1 calc . . C10 C -0.0276(6) 0.1186(4) 0.2108(5) 0.0326(16) Uani 1 d . . C11 C 0.0302(6) 0.0596(5) 0.2113(5) 0.0361(17) Uani 1 d . . C12 C 0.0998(6) 0.0471(5) 0.2739(5) 0.0351(17) Uani 1 d . . C13 C 0.1137(6) 0.0949(4) 0.3361(5) 0.0351(17) Uani 1 d . . C14 C -0.1045(6) 0.1312(5) 0.1445(5) 0.0369(18) Uani 1 d . . H14 H -0.1285 0.0733 0.1164 0.044 Uiso 1 calc . . C15 C -0.0645(5) 0.1907(5) 0.1005(4) 0.0315(16) Uani 1 d . . C16 C -0.0474(5) 0.2817(4) 0.1157(4) 0.0270(14) Uani 1 d . . H16 H -0.0613 0.3047 0.1539 0.032 Uiso 1 calc . . C17 C -0.0115(5) 0.3395(4) 0.0778(4) 0.0258(14) Uani 1 d . . C18 C 0.0118(5) 0.3031(5) 0.0230(4) 0.0290(14) Uani 1 d . . C19 C -0.0038(6) 0.2135(5) 0.0068(4) 0.0332(16) Uani 1 d . . C20 C -0.0424(5) 0.1590(5) 0.0450(4) 0.0326(16) Uani 1 d . . C21 C 0.0046(5) 0.4364(4) 0.0960(4) 0.0237(13) Uani 1 d . . H21 H 0.0147 0.4641 0.0554 0.028 Uiso 1 calc . . C22 C 0.0936(5) 0.4649(4) 0.1598(4) 0.0225(13) Uani 1 d . . C23 C 0.0935(5) 0.4769(4) 0.2273(4) 0.0206(12) Uani 1 d . . H23 H 0.0357 0.4687 0.2338 0.025 Uiso 1 calc . . C24 C 0.1744(5) 0.5006(4) 0.2868(4) 0.0218(13) Uani 1 d . . C25 C 0.2590(5) 0.5120(4) 0.2760(4) 0.0239(13) Uani 1 d . . C26 C 0.2621(5) 0.5006(4) 0.2080(3) 0.0208(12) Uani 1 d . . C27 C 0.1796(5) 0.4759(4) 0.1510(4) 0.0214(12) Uani 1 d . . C28 C 0.1733(5) 0.5127(4) 0.3612(4) 0.0247(14) Uani 1 d . . H28 H 0.2241 0.5621 0.3869 0.03 Uiso 1 calc . . C29 C 0.4045(6) 0.3495(5) 0.5271(4) 0.0336(16) Uani 1 d . . H29A H 0.4449 0.4071 0.5393 0.04 Uiso 1 calc . . H29B H 0.404 0.3257 0.5713 0.04 Uiso 1 calc . . C31 C 0.1570(7) -0.0220(5) 0.2707(5) 0.0389(18) Uani 1 d . . H31A H 0.1158 -0.0745 0.2416 0.047 Uiso 1 calc . . H31B H 0.1878 -0.038 0.3187 0.047 Uiso 1 calc . . C33 C 0.0245(6) 0.1813(5) -0.0515(4) 0.0381(18) Uani 1 d . . H33A H 0.0024 0.2148 -0.0925 0.046 Uiso 1 calc . . H33B H -0.0037 0.1196 -0.0666 0.046 Uiso 1 calc . . C35 C 0.3543(5) 0.5156(4) 0.1996(4) 0.0252(13) Uani 1 d . . H35A H 0.3868 0.5752 0.2195 0.03 Uiso 1 calc . . H35B H 0.3454 0.5098 0.149 0.03 Uiso 1 calc . . C37 C 0.5299(6) 0.2649(5) 0.5331(5) 0.0358(17) Uani 1 d . . H37A H 0.5773 0.3176 0.5533 0.043 Uiso 1 calc . . H37B H 0.552 0.2294 0.5031 0.043 Uiso 1 calc . . C38 C 0.5194(6) 0.2140(5) 0.5922(5) 0.0385(18) Uani 1 d . . C39 C 0.4792(7) 0.1257(6) 0.5763(6) 0.047(2) Uani 1 d . . H39 H 0.4604 0.0982 0.5298 0.057 Uiso 1 calc . . C40 C 0.4676(8) 0.0794(6) 0.6310(6) 0.055(3) Uani 1 d . . H40 H 0.4391 0.0201 0.621 0.067 Uiso 1 calc . . C41 C 0.4966(8) 0.1175(8) 0.6989(6) 0.057(3) Uani 1 d . . H41 H 0.4898 0.0846 0.7355 0.069 Uiso 1 calc . . C42 C 0.5359(8) 0.2049(7) 0.7131(6) 0.054(2) Uani 1 d . . H42 H 0.5544 0.2327 0.7594 0.065 Uiso 1 calc . . C43 C 0.5482(7) 0.2516(6) 0.6593(5) 0.044(2) Uani 1 d . . H43 H 0.5772 0.3108 0.6697 0.052 Uiso 1 calc . . C44 C 0.2968(6) -0.0504(6) 0.2431(6) 0.046(2) Uani 1 d . . H44A H 0.3272 -0.0599 0.293 0.055 Uiso 1 calc . . H44B H 0.3454 -0.0229 0.2262 0.055 Uiso 1 calc . . C45 C 0.2524(6) -0.1376(5) 0.2009(5) 0.0389(18) Uani 1 d . . C46 C 0.2193(8) -0.2064(6) 0.2327(5) 0.049(2) Uani 1 d . . H46 H 0.2237 -0.1973 0.2802 0.059 Uiso 1 calc . . C47 C 0.1808(8) -0.2869(6) 0.1961(6) 0.055(3) Uani 1 d . . H47 H 0.1566 -0.3326 0.2173 0.066 Uiso 1 calc . . C48 C 0.1779(7) -0.2997(5) 0.1267(5) 0.048(2) Uani 1 d . . H48 H 0.1529 -0.3552 0.1012 0.057 Uiso 1 calc . . C49 C 0.2106(7) -0.2333(5) 0.0952(5) 0.047(2) Uani 1 d . . H49 H 0.2077 -0.243 0.0481 0.057 Uiso 1 calc . . C50 C 0.2485(6) -0.1506(6) 0.1326(5) 0.0394(18) Uani 1 d . . H50 H 0.2711 -0.1045 0.1108 0.047 Uiso 1 calc . . C51 C 0.1670(8) 0.1685(6) -0.0800(5) 0.045(2) Uani 1 d . . H51A H 0.1463 0.1061 -0.0962 0.054 Uiso 1 calc . . H51B H 0.2353 0.1795 -0.0582 0.054 Uiso 1 calc . . C52 C 0.1380(6) 0.2206(6) -0.1425(5) 0.0374(17) Uani 1 d . . C53 C 0.1812(11) 0.3056(7) -0.1357(6) 0.068(3) Uani 1 d . . H53 H 0.2281 0.3302 -0.0924 0.082 Uiso 1 calc . . C54 C 0.1567(12) 0.3548(8) -0.1913(6) 0.087(5) Uani 1 d . . H54 H 0.1871 0.413 -0.1869 0.105 Uiso 1 calc . . C55 C 0.0880(9) 0.3193(10) -0.2533(7) 0.077(4) Uani 1 d . . H55 H 0.0703 0.3538 -0.2914 0.092 Uiso 1 calc . . C56 C 0.0449(12) 0.2355(14) -0.2611(9) 0.095(5) Uani 1 d . . H56 H -0.0037 0.2121 -0.3039 0.114 Uiso 1 calc . . C57 C 0.0733(10) 0.1835(10) -0.2045(7) 0.076(4) Uani 1 d . . H57 H 0.0474 0.1237 -0.2102 0.092 Uiso 1 calc . . C58 C 0.4977(6) 0.4510(7) 0.2192(5) 0.043(2) Uani 1 d . . H58A H 0.4794 0.4249 0.1702 0.051 Uiso 1 calc . . H58B H 0.5369 0.4143 0.2505 0.051 Uiso 1 calc . . C59 C 0.5535(6) 0.5401(7) 0.2267(5) 0.044(2) Uani 1 d . . C60 C 0.5981(6) 0.5883(6) 0.2912(4) 0.0398(18) Uani 1 d . . H60 H 0.5954 0.5637 0.3325 0.048 Uiso 1 calc . . C61 C 0.6463(7) 0.6712(8) 0.2974(5) 0.052(2) Uani 1 d . . H61 H 0.6763 0.7027 0.3425 0.063 Uiso 1 calc . . C62 C 0.6511(10) 0.7083(10) 0.2388(5) 0.080(4) Uani 1 d . . H62 H 0.688 0.7637 0.2434 0.096 Uiso 1 calc . . C63 C 0.6026(12) 0.6652(9) 0.1738(6) 0.088(4) Uani 1 d . . H63 H 0.5999 0.6936 0.133 0.105 Uiso 1 calc . . C64 C 0.5572(9) 0.5802(9) 0.1666(5) 0.083(5) Uani 1 d . . H64 H 0.5286 0.5491 0.1213 0.099 Uiso 1 calc . . C65 C -0.0174(7) 0.2283(6) 0.4129(6) 0.047(2) Uani 1 d . . H65A H -0.0027 0.2619 0.4582 0.07 Uiso 1 calc . . H65B H -0.0612 0.1752 0.4096 0.07 Uiso 1 calc . . H65C H -0.0451 0.2628 0.3747 0.07 Uiso 1 calc . . C66 C -0.1868(6) 0.1607(6) 0.1566(6) 0.046(2) Uani 1 d . . H66A H -0.2336 0.167 0.1113 0.069 Uiso 1 calc . . H66B H -0.1661 0.2164 0.1857 0.069 Uiso 1 calc . . H66C H -0.2136 0.1175 0.1807 0.069 Uiso 1 calc . . C67 C -0.0802(5) 0.4671(5) 0.1045(4) 0.0326(16) Uani 1 d . . H67A H -0.0666 0.53 0.1161 0.049 Uiso 1 calc . . H67B H -0.0945 0.4389 0.1425 0.049 Uiso 1 calc . . H67C H -0.1334 0.4518 0.0605 0.049 Uiso 1 calc . . C68 C 0.0830(6) 0.5380(5) 0.3626(4) 0.0346(17) Uani 1 d . . H68A H 0.0857 0.5446 0.4114 0.052 Uiso 1 calc . . H68B H 0.0308 0.4926 0.3355 0.052 Uiso 1 calc . . H68C H 0.0749 0.5928 0.3419 0.052 Uiso 1 calc . . Cl1 Cl 0.3660(7) 0.1071(4) 0.3873(4) 0.0369(15) Uani 0.6 d A 1 Cl'1 Cl 0.3607(11) 0.1281(8) 0.3743(7) 0.056(3) Uani 0.4 d B 2 Cl2 Cl 0.19537(17) 0.05418(13) 0.08060(12) 0.0501(6) Uani 1 d . . Cl3 Cl 0.29775(15) 0.34368(14) 0.05675(12) 0.0441(5) Uani 1 d . . Cl4 Cl 0.51170(15) 0.41953(13) 0.40060(9) 0.0394(5) Uani 1 d . . C1A C 0.6275(4) 0.3807(4) 0.0453(4) 0.053(2) Uani 1 d . . Br1A Br 0.6607(3) 0.48993(19) 0.0140(2) 0.0377(7) Uani 0.65 d C 1 ClA' Cl 0.6380(12) 0.4773(11) 0.0042(12) 0.058(5) Uani 0.35 d C 2 Cl1A Cl 0.5096(6) 0.3634(11) 0.0365(8) 0.048(3) Uani 0.65 d C 1 BrA' Br 0.4975(5) 0.3541(8) 0.0306(6) 0.056(3) Uani 0.35 d C 2 Cl2A Cl 0.6962(2) 0.3820(4) 0.1347(2) 0.0985(15) Uani 1 d . . Cl3A Cl 0.6526(3) 0.2996(2) -0.0035(3) 0.0975(14) Uani 1 d . . C1B C 0.8293(4) 0.4823(4) 0.3915(3) 0.057(3) Uani 1 d . . Br1B Br 0.71535(12) 0.43779(11) 0.40273(9) 0.0791(5) Uani 1 d . . Cl1B Cl 0.86499(15) 0.59271(12) 0.42705(12) 0.0423(5) Uani 1 d . . Cl2B Cl 0.9103(2) 0.4191(2) 0.43787(19) 0.0702(8) Uani 1 d . . Cl3B Cl 0.8073(3) 0.4656(3) 0.30004(14) 0.0795(10) Uani 1 d . . C1C C 0.2333(5) -0.1713(5) 0.4741(4) 0.071(3) Uani 1 d . . Br1C Br 0.31518(10) -0.07851(8) 0.45657(8) 0.0696(4) Uani 1 d . . Cl1C Cl 0.1236(3) -0.1430(5) 0.4494(3) 0.1183(19) Uani 1 d . . Cl2C Cl 0.2283(3) -0.2625(2) 0.4192(3) 0.1035(14) Uani 1 d . . Cl3C Cl 0.2794(4) -0.1863(3) 0.5634(2) 0.1089(16) Uani 1 d . . C1D C 0.5695(9) 0.1658(7) 0.2410(8) 0.058(6) Uani 0.5 d D 1 Br1D Br 0.49052(16) 0.15455(12) 0.29476(10) 0.0473(5) Uani 0.5 d D 1 Cl1D Cl 0.6344(7) 0.0801(6) 0.2529(5) 0.084(2) Uani 0.5 d D 1 Cl2D Cl 0.6521(5) 0.2625(3) 0.2714(3) 0.0666(15) Uani 0.5 d D 1 Cl3D Cl 0.5034(9) 0.1739(8) 0.1521(6) 0.120(3) Uani 0.5 d D 1 C1D' C 0.5336(6) 0.1804(6) 0.2359(5) 0.061(7) Uani 0.5 d E 2 BrD' Br 0.4114(2) 0.1308(2) 0.17041(16) 0.0813(8) Uani 0.5 d E 2 Cl1' Cl 0.5279(6) 0.2499(5) 0.3039(4) 0.0792(18) Uani 0.5 d E 2 Cl2' Cl 0.5941(7) 0.2400(6) 0.1893(5) 0.097(2) Uani 0.5 d E 2 Cl3' Cl 0.5897(9) 0.0930(6) 0.2674(7) 0.118(3) Uani 0.5 d E 2 C1E C 0.3839(7) 0.0409(7) -0.0834(5) 0.085(9) Uani 0.5 d . . Br1E Br 0.3289(3) 0.0316(3) -0.0119(2) 0.0952(10) Uani 0.5 d . . Cl1E Cl 0.4807(7) 0.1241(7) -0.0441(7) 0.165(7) Uani 0.5 d . . Cl2E Cl 0.3019(4) 0.0693(3) -0.1597(2) 0.0542(12) Uani 0.5 d . . Cl3E Cl 0.4180(10) -0.0594(8) -0.0935(9) 0.203(9) Uani 0.5 d . . C1F C 0.1454(12) 0.0759(8) 0.6049(12) 0.096(5) Uani 0.5 d F 1 H1F H 0.1181 0.048 0.5554 0.115 Uiso 0.5 calc F 1 Cl1F Cl 0.2657(9) 0.0793(11) 0.6331(8) 0.076(5) Uani 0.5 d F 1 Cl2F Cl 0.1218(3) 0.1818(2) 0.6034(3) 0.0446(10) Uani 0.5 d F 1 Cl3F Cl 0.0876(7) 0.0159(6) 0.6546(5) 0.075(2) Uani 0.5 d F 1 C1F' C 0.1347(8) 0.0704(10) 0.6108(4) 0.096(5) Uani 0.5 d G 2 H1F' H 0.1297 0.1331 0.6137 0.115 Uiso 0.5 calc G 2 Cl4F Cl 0.0493(5) 0.0201(4) 0.5304(3) 0.084(2) Uani 0.5 d G 2 Cl5F Cl 0.2488(6) 0.0645(11) 0.6141(6) 0.053(3) Uani 0.5 d G 2 Cl6F Cl 0.1140(6) 0.0270(7) 0.6841(4) 0.070(2) Uani 0.5 d G 2 O1W O 0.3068(9) 0.2876(7) 0.2015(6) 0.042(3) Uani 0.5 d H 1 O2W O 0.2131(13) 0.2622(10) 0.2178(12) 0.077(5) Uani 0.5 d I 2 O3W O 0.5173(12) 0.1101(12) -0.1150(10) 0.068(5) Uani 0.5 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 N30 0.036(4) 0.028(3) 0.034(3) 0.006(2) 0.012(3) 0.010(3) N32 0.038(4) 0.026(3) 0.050(4) -0.001(3) 0.014(3) 0.005(3) N34 0.033(3) 0.028(3) 0.034(3) 0.003(2) 0.006(3) 0.006(2) N36 0.026(3) 0.040(3) 0.025(3) 0.003(3) 0.005(3) 0.010(3) O4 0.054(4) 0.029(3) 0.039(3) 0.014(2) 0.019(3) 0.014(2) O6 0.044(3) 0.028(2) 0.024(2) 0.0040(19) 0.010(2) 0.002(2) O11 0.048(4) 0.024(2) 0.048(3) -0.001(2) 0.009(3) 0.007(2) O13 0.044(3) 0.032(3) 0.047(3) 0.008(2) 0.020(3) 0.010(2) O18 0.037(3) 0.030(2) 0.026(2) -0.005(2) 0.008(2) -0.001(2) O20 0.053(4) 0.022(3) 0.044(3) -0.008(2) -0.003(3) 0.002(2) O25 0.029(3) 0.031(2) 0.020(2) 0.0013(19) 0.003(2) -0.002(2) O27 0.027(3) 0.035(2) 0.019(2) -0.0009(18) 0.009(2) 0.003(2) C1 0.038(4) 0.021(3) 0.029(3) 0.008(3) 0.021(3) 0.010(3) C2 0.038(4) 0.025(3) 0.033(4) 0.006(3) 0.021(3) 0.006(3) C3 0.044(5) 0.026(3) 0.037(4) 0.009(3) 0.027(4) 0.008(3) C4 0.049(5) 0.023(3) 0.035(4) 0.012(3) 0.023(4) 0.010(3) C5 0.038(4) 0.028(3) 0.029(3) 0.007(3) 0.016(3) 0.011(3) C6 0.043(4) 0.022(3) 0.021(3) 0.002(2) 0.018(3) 0.008(3) C7 0.043(5) 0.029(4) 0.042(4) 0.011(3) 0.025(4) 0.002(3) C8 0.035(4) 0.020(3) 0.052(5) 0.009(3) 0.027(4) -0.001(3) C9 0.038(4) 0.023(3) 0.054(5) 0.011(3) 0.027(4) 0.004(3) C10 0.029(4) 0.021(3) 0.047(4) 0.001(3) 0.017(3) -0.004(3) C11 0.039(4) 0.019(3) 0.050(5) 0.006(3) 0.016(4) 0.002(3) C12 0.030(4) 0.022(3) 0.052(5) 0.008(3) 0.012(4) 0.004(3) C13 0.045(5) 0.018(3) 0.051(5) 0.011(3) 0.028(4) 0.004(3) C14 0.029(4) 0.022(3) 0.058(5) 0.008(3) 0.016(4) -0.002(3) C15 0.021(3) 0.025(3) 0.043(4) 0.007(3) 0.007(3) -0.002(3) C16 0.022(3) 0.022(3) 0.038(4) 0.006(3) 0.012(3) 0.002(3) C17 0.019(3) 0.022(3) 0.031(3) 0.001(3) 0.002(3) 0.004(2) C18 0.024(3) 0.029(3) 0.029(3) 0.000(3) 0.005(3) 0.002(3) C19 0.029(4) 0.033(4) 0.031(4) -0.005(3) 0.003(3) 0.007(3) C20 0.026(4) 0.021(3) 0.042(4) -0.002(3) 0.003(3) 0.003(3) C21 0.021(3) 0.020(3) 0.026(3) 0.003(2) 0.001(3) 0.006(2) C22 0.019(3) 0.018(3) 0.028(3) 0.004(2) 0.004(3) 0.005(2) C23 0.019(3) 0.018(3) 0.025(3) 0.003(2) 0.009(3) 0.002(2) C24 0.027(3) 0.018(3) 0.025(3) 0.007(2) 0.012(3) 0.009(2) C25 0.023(3) 0.020(3) 0.028(3) 0.004(2) 0.010(3) 0.001(2) C26 0.020(3) 0.024(3) 0.018(3) 0.004(2) 0.006(3) 0.003(2) C27 0.021(3) 0.022(3) 0.022(3) 0.003(2) 0.009(3) 0.001(2) C28 0.036(4) 0.019(3) 0.025(3) 0.007(2) 0.016(3) 0.009(3) C29 0.048(5) 0.028(3) 0.026(3) 0.006(3) 0.011(3) 0.013(3) C31 0.047(5) 0.028(3) 0.042(4) 0.002(3) 0.014(4) 0.014(3) C33 0.038(4) 0.038(4) 0.031(4) -0.010(3) 0.006(3) 0.004(3) C35 0.022(3) 0.030(3) 0.022(3) 0.005(3) 0.006(3) 0.003(3) C37 0.034(4) 0.029(3) 0.043(4) 0.001(3) 0.012(4) 0.004(3) C38 0.033(4) 0.029(4) 0.050(5) 0.015(3) 0.007(4) 0.011(3) C39 0.045(5) 0.031(4) 0.056(5) 0.007(4) 0.009(4) 0.002(4) C40 0.052(6) 0.034(4) 0.073(7) 0.021(5) 0.015(5) -0.003(4) C41 0.047(6) 0.066(6) 0.060(6) 0.036(5) 0.016(5) 0.012(5) C42 0.056(6) 0.051(5) 0.047(5) 0.012(4) 0.006(5) 0.015(5) C43 0.045(5) 0.034(4) 0.049(5) 0.012(4) 0.013(4) 0.006(4) C44 0.031(4) 0.034(4) 0.059(5) -0.014(4) 0.000(4) 0.010(3) C45 0.043(5) 0.026(3) 0.044(4) -0.004(3) 0.008(4) 0.012(3) C46 0.073(7) 0.029(4) 0.047(5) 0.008(4) 0.017(5) 0.023(4) C47 0.058(6) 0.032(4) 0.068(6) 0.006(4) 0.011(5) 0.015(4) C48 0.051(5) 0.023(3) 0.053(5) -0.006(3) -0.003(4) 0.009(3) C49 0.055(6) 0.047(5) 0.034(4) -0.001(4) 0.002(4) 0.028(4) C50 0.039(5) 0.036(4) 0.046(5) 0.004(3) 0.016(4) 0.014(3) C51 0.061(6) 0.032(4) 0.047(5) 0.004(3) 0.024(4) 0.012(4) C52 0.035(4) 0.040(4) 0.042(4) 0.004(3) 0.020(4) 0.006(3) C53 0.115(11) 0.041(5) 0.050(6) 0.005(4) 0.032(7) 0.013(6) C54 0.166(17) 0.055(7) 0.070(8) 0.022(6) 0.067(10) 0.042(9) C55 0.075(7) 0.103(8) 0.066(6) 0.034(6) 0.031(5) 0.038(6) C56 0.077(8) 0.128(9) 0.069(7) 0.016(7) 0.019(6) -0.002(7) C57 0.072(7) 0.089(7) 0.057(6) 0.015(5) 0.023(5) -0.023(5) C58 0.035(4) 0.063(5) 0.034(4) -0.007(4) 0.016(4) 0.013(4) C59 0.023(4) 0.077(6) 0.029(4) 0.000(4) 0.010(3) 0.004(4) C60 0.033(4) 0.060(5) 0.028(4) 0.005(4) 0.013(3) 0.011(4) C61 0.041(5) 0.070(6) 0.043(5) 0.011(5) 0.015(4) -0.002(5) C62 0.067(8) 0.098(10) 0.056(7) 0.015(7) 0.017(6) -0.031(7) C63 0.099(8) 0.103(8) 0.062(6) 0.027(6) 0.041(6) -0.011(6) C64 0.059(7) 0.146(13) 0.026(4) -0.007(6) 0.019(5) -0.039(8) C65 0.052(6) 0.042(4) 0.064(6) 0.011(4) 0.042(5) 0.007(4) C66 0.032(4) 0.042(4) 0.072(6) 0.021(4) 0.028(4) 0.005(3) C67 0.026(4) 0.032(3) 0.036(4) 0.004(3) 0.006(3) 0.006(3) C68 0.042(5) 0.036(4) 0.036(4) 0.009(3) 0.023(4) 0.018(3) Cl1 0.044(3) 0.028(2) 0.042(3) 0.0044(17) 0.019(2) 0.0068(19) Cl'1 0.041(4) 0.056(6) 0.058(6) -0.029(5) 0.009(4) 0.005(5) Cl2 0.0560(14) 0.0301(9) 0.0464(11) 0.0046(8) -0.0026(10) 0.0043(8) Cl3 0.0324(10) 0.0441(10) 0.0513(12) -0.0056(9) 0.0106(9) 0.0063(8) Cl4 0.0424(11) 0.0418(10) 0.0264(8) 0.0072(7) 0.0053(8) 0.0010(8) C1A 0.041(5) 0.065(6) 0.052(5) 0.006(5) 0.014(4) 0.013(4) Br1A 0.0234(19) 0.0497(10) 0.0367(12) -0.0005(9) 0.0083(13) 0.0038(11) ClA' 0.019(7) 0.091(9) 0.053(8) 0.008(6) 0.007(6) -0.007(5) Cl1A 0.027(3) 0.071(4) 0.039(3) -0.013(3) 0.009(2) -0.005(2) BrA' 0.040(3) 0.076(5) 0.064(6) 0.027(5) 0.027(3) 0.022(3) Cl2A 0.0504(17) 0.151(4) 0.076(2) 0.056(2) 0.0018(15) 0.0043(19) Cl3A 0.082(2) 0.0648(18) 0.169(4) -0.007(2) 0.074(3) 0.0149(16) C1B 0.063(7) 0.058(6) 0.055(6) -0.004(5) 0.030(5) 0.009(5) Br1B 0.0791(10) 0.0840(9) 0.0823(10) 0.0094(7) 0.0406(8) 0.0099(7) Cl1B 0.0427(11) 0.0329(9) 0.0529(12) 0.0037(8) 0.0187(9) 0.0077(8) Cl2B 0.0704(18) 0.0746(17) 0.085(2) 0.0207(15) 0.0418(16) 0.0341(15) Cl3B 0.086(2) 0.112(3) 0.0364(12) -0.0059(14) 0.0333(14) -0.0186(18) C1C 0.052(7) 0.072(7) 0.072(8) 0.021(6) 0.007(6) -0.002(6) Br1C 0.0706(9) 0.0557(7) 0.0785(9) 0.0022(6) 0.0259(7) 0.0021(6) Cl1C 0.0495(19) 0.202(6) 0.119(3) 0.065(4) 0.036(2) 0.044(3) Cl2C 0.107(3) 0.0491(16) 0.124(3) -0.0156(18) 0.014(3) -0.0061(17) Cl3C 0.126(4) 0.115(3) 0.0574(18) 0.048(2) 0.000(2) 0.005(3) C1D 0.061(8) 0.058(7) 0.056(7) 0.008(5) 0.023(5) 0.009(5) Br1D 0.0579(12) 0.0433(9) 0.0446(10) 0.0018(8) 0.0226(9) 0.0110(8) Cl1D 0.088(3) 0.082(3) 0.090(3) 0.0074(18) 0.0411(19) 0.0145(18) Cl2D 0.092(4) 0.044(2) 0.069(3) 0.017(2) 0.036(3) 0.003(2) Cl3D 0.123(4) 0.124(4) 0.113(4) 0.016(2) 0.042(2) 0.014(2) C1D' 0.033(11) 0.038(9) 0.087(17) 0.017(10) -0.009(10) 0.000(8) BrD' 0.083(2) 0.0866(19) 0.0647(15) -0.0015(14) 0.0209(14) 0.0031(15) Cl1' 0.083(4) 0.077(4) 0.063(3) -0.004(3) 0.009(3) 0.012(3) Cl2' 0.104(6) 0.081(4) 0.111(6) 0.020(4) 0.049(5) 0.001(4) Cl3' 0.129(7) 0.070(4) 0.129(7) 0.037(4) 0.009(5) 0.019(4) C1E 0.08(2) 0.073(16) 0.10(2) 0.010(15) 0.021(17) 0.038(15) Br1E 0.096(2) 0.097(2) 0.088(2) 0.0130(18) 0.0154(18) 0.0425(19) Cl1E 0.143(11) 0.125(9) 0.219(16) -0.056(10) 0.103(11) -0.072(8) Cl2E 0.088(4) 0.042(2) 0.045(2) 0.0114(18) 0.033(2) 0.028(2) Cl3E 0.167(13) 0.237(16) 0.218(15) -0.033(12) 0.070(11) 0.085(12) C1F 0.104(9) 0.082(8) 0.108(9) 0.025(7) 0.045(7) 0.010(7) Cl1F 0.045(4) 0.079(9) 0.103(10) 0.062(8) 0.019(5) 0.013(4) Cl2F 0.049(2) 0.0275(16) 0.075(3) 0.0269(18) 0.040(2) 0.0094(15) Cl3F 0.088(6) 0.063(4) 0.078(5) 0.021(4) 0.048(5) -0.023(4) C1F' 0.104(9) 0.082(8) 0.108(9) 0.025(7) 0.045(7) 0.010(7) Cl4F 0.096(5) 0.050(3) 0.066(3) 0.001(2) -0.013(4) 0.001(3) Cl5F 0.042(5) 0.054(4) 0.060(4) 0.018(3) 0.011(3) 0.012(3) Cl6F 0.068(5) 0.071(5) 0.056(4) 0.026(4) 0.017(4) -0.021(3) O1W 0.045(7) 0.032(5) 0.031(5) -0.005(4) -0.003(5) -0.001(5) O2W 0.065(8) 0.043(6) 0.109(9) 0.026(6) 0.013(7) 0.009(6) O3W 0.062(10) 0.072(10) 0.070(10) -0.025(8) 0.039(9) -0.019(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N30 C29 1.487(10) . ? N30 C37 1.505(11) . ? N30 H30A 0.99 . ? N30 H30B 0.99 . ? N32 C44 1.503(11) . ? N32 C31 1.539(12) . ? N32 H32A 0.99 . ? N32 H32B 0.99 . ? N34 C51 1.493(12) . ? N34 C33 1.488(11) . ? N34 H34A 0.99 . ? N34 H34B 0.99 . ? N36 C58 1.492(10) . ? N36 C35 1.519(9) . ? N36 H36A 0.99 . ? N36 H36B 0.99 . ? O4 C4 1.373(9) . ? O4 H4 0.84 . ? O6 C6 1.381(10) . ? O6 H6 0.84 . ? O11 C11 1.368(11) . ? O11 H11 0.84 . ? O13 C13 1.375(11) . ? O13 H13 0.84 . ? O18 C18 1.362(10) . ? O18 H18 0.84 . ? O20 C20 1.397(9) . ? O20 H20 0.84 . ? O25 C25 1.357(9) . ? O25 H25 0.84 . ? O27 C27 1.380(8) . ? O27 H27 0.84 . ? C1 C2 1.404(11) . ? C1 C6 1.406(11) . ? C1 C28 1.523(8) . ? C2 C3 1.406(10) . ? C2 H2 0.95 . ? C3 C4 1.398(13) . ? C3 C7 1.524(11) . ? C4 C5 1.406(12) . ? C5 C6 1.394(10) . ? C5 C29 1.507(12) . ? C7 C8 1.517(12) . ? C7 C65 1.527(13) . ? C7 H7 1 . ? C8 C9 1.382(13) . ? C8 C13 1.395(12) . ? C9 C10 1.406(12) . ? C9 H9 0.95 . ? C10 C11 1.389(12) . ? C10 C14 1.511(12) . ? C11 C12 1.405(12) . ? C12 C13 1.378(13) . ? C12 C31 1.521(11) . ? C14 C15 1.532(11) . ? C14 C66 1.526(12) . ? C14 H14 1 . ? C15 C20 1.388(12) . ? C15 C16 1.414(10) . ? C16 C17 1.392(10) . ? C16 H16 0.95 . ? C17 C18 1.413(11) . ? C17 C21 1.514(9) . ? C18 C19 1.397(11) . ? C19 C20 1.387(13) . ? C19 C33 1.499(11) . ? C21 C22 1.529(9) . ? C21 C67 1.539(10) . ? C21 H21 1 . ? C22 C23 1.381(10) . ? C22 C27 1.407(10) . ? C23 C24 1.403(10) . ? C23 H23 0.95 . ? C24 C25 1.403(10) . ? C24 C28 1.526(9) . ? C25 C26 1.409(10) . ? C26 C27 1.392(10) . ? C26 C35 1.496(9) . ? C28 C68 1.535(10) . ? C28 H28 1 . ? C29 H29A 0.99 . ? C29 H29B 0.99 . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? C33 H33A 0.99 . ? C33 H33B 0.99 . ? C35 H35A 0.99 . ? C35 H35B 0.99 . ? C37 C38 1.513(12) . ? C37 H37A 0.99 . ? C37 H37B 0.99 . ? C38 C43 1.359(14) . ? C38 C39 1.409(12) . ? C39 C40 1.404(15) . ? C39 H39 0.95 . ? C40 C41 1.375(18) . ? C40 H40 0.95 . ? C41 C42 1.391(17) . ? C41 H41 0.95 . ? C42 C43 1.395(15) . ? C42 H42 0.95 . ? C43 H43 0.95 . ? C44 C45 1.516(11) . ? C44 H44A 0.99 . ? C44 H44B 0.99 . ? C45 C46 1.405(14) . ? C45 C50 1.377(13) . ? C46 C47 1.377(14) . ? C46 H46 0.95 . ? C47 C48 1.404(16) . ? C47 H47 0.95 . ? C48 C49 1.371(9) . ? C48 H48 0.95 . ? C49 C50 1.411(13) . ? C49 H49 0.95 . ? C50 H50 0.95 . ? C51 C52 1.513(13) . ? C51 H51A 0.99 . ? C51 H51B 0.99 . ? C52 C57 1.355(16) . ? C52 C53 1.381(15) . ? C53 C54 1.373(9) . ? C53 H53 0.95 . ? C54 C55 1.372(19) . ? C54 H54 0.95 . ? C55 C56 1.36(2) . ? C55 H55 0.95 . ? C56 C57 1.42(2) . ? C56 H56 0.95 . ? C57 H57 0.95 . ? C58 C59 1.505(15) . ? C58 H58A 0.99 . ? C58 H58B 0.99 . ? C59 C60 1.383(13) . ? C59 C64 1.413(14) . ? C60 C61 1.381(15) . ? C60 H60 0.95 . ? C61 C62 1.368(9) . ? C61 H61 0.95 . ? C62 C63 1.365(9) . ? C62 H62 0.95 . ? C63 C64 1.39(2) . ? C63 H63 0.95 . ? C64 H64 0.95 . ? C65 H65A 0.98 . ? C65 H65B 0.98 . ? C65 H65C 0.98 . ? C66 H66A 0.98 . ? C66 H66B 0.98 . ? C66 H66C 0.98 . ? C67 H67A 0.98 . ? C67 H67B 0.98 . ? C67 H67C 0.98 . ? C68 H68A 0.98 . ? C68 H68B 0.98 . ? C68 H68C 0.98 . ? C1A Cl3A 1.756(7) . ? C1A Cl2A 1.761(7) . ? C1A Cl1A 1.769(9) . ? C1A ClA' 1.776(10) . ? C1A Br1A 1.915(7) . ? C1A BrA' 1.928(9) . ? C1B Cl2B 1.764(6) . ? C1B Cl3B 1.775(6) . ? C1B Cl1B 1.780(6) . ? C1B Br1B 1.908(6) . ? C1C Cl1C 1.748(8) . ? C1C Cl3C 1.749(8) . ? C1C Cl2C 1.757(8) . ? C1C Br1C 1.920(8) . ? C1D Cl3D 1.768(10) . ? C1D Cl2D 1.770(10) . ? C1D Cl1D 1.781(10) . ? C1D Br1D 1.910(18) . ? C1D' Cl2' 1.760(9) . ? C1D' Cl1' 1.763(9) . ? C1D' Cl3' 1.766(9) . ? C1D' BrD' 1.934(9) . ? C1E Cl2E 1.764(9) . ? C1E Cl3E 1.764(9) . ? C1E Cl1E 1.766(9) . ? C1E Br1E 1.933(9) . ? Cl1E O3W 1.75(2) . ? C1F Cl2F 1.757(10) . ? C1F Cl3F 1.785(10) . ? C1F Cl1F 1.760(10) . ? C1F H1F 1 . ? C1F' Cl6F 1.774(5) . ? C1F' Cl5F 1.782(10) . ? C1F' Cl4F 1.775(5) . ? C1F' H1F' 1 . ? Cl4F Cl4F 1.622(11) 2_556 ? Cl4F Cl5F 2.950(8) . ? Cl4F Cl6F 2.929(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 C29 N30 C37 113.7(6) . . ? C29 N30 H30A 108.8 . . ? C37 N30 H30A 108.8 . . ? C29 N30 H30B 108.8 . . ? C37 N30 H30B 108.8 . . ? H30A N30 H30B 107.7 . . ? C44 N32 C31 113.0(7) . . ? C44 N32 H32A 109 . . ? C31 N32 H32A 109 . . ? C44 N32 H32B 109 . . ? C31 N32 H32B 109 . . ? H32A N32 H32B 107.8 . . ? C51 N34 C33 115.9(7) . . ? C51 N34 H34A 108.3 . . ? C33 N34 H34A 108.3 . . ? C51 N34 H34B 108.3 . . ? C33 N34 H34B 108.3 . . ? H34A N34 H34B 107.4 . . ? C58 N36 C35 113.4(6) . . ? C58 N36 H36A 108.9 . . ? C35 N36 H36A 108.9 . . ? C58 N36 H36B 108.9 . . ? C35 N36 H36B 108.9 . . ? H36A N36 H36B 107.7 . . ? C4 O4 H4 109.5 . . ? C6 O6 H6 109.5 . . ? C11 O11 H11 109.5 . . ? C13 O13 H13 109.5 . . ? C18 O18 H18 109.5 . . ? C20 O20 H20 109.5 . . ? C25 O25 H25 109.5 . . ? C27 O27 H27 109.5 . . ? C2 C1 C6 117.5(6) . . ? C2 C1 C28 120.9(7) . . ? C6 C1 C28 121.5(6) . . ? C1 C2 C3 122.5(8) . . ? C1 C2 H2 118.8 . . ? C3 C2 H2 118.8 . . ? C4 C3 C2 117.3(7) . . ? C4 C3 C7 122.3(7) . . ? C2 C3 C7 120.3(8) . . ? O4 C4 C5 114.7(8) . . ? O4 C4 C3 122.9(7) . . ? C5 C4 C3 122.4(7) . . ? C4 C5 C6 118.0(7) . . ? C4 C5 C29 117.8(7) . . ? C6 C5 C29 124.0(7) . . ? O6 C6 C5 121.7(7) . . ? O6 C6 C1 116.1(6) . . ? C5 C6 C1 122.1(7) . . ? C3 C7 C8 111.5(6) . . ? C3 C7 C65 112.2(7) . . ? C8 C7 C65 113.4(8) . . ? C3 C7 H7 106.4 . . ? C8 C7 H7 106.4 . . ? C65 C7 H7 106.4 . . ? C9 C8 C13 117.9(8) . . ? C9 C8 C7 122.3(7) . . ? C13 C8 C7 119.7(8) . . ? C10 C9 C8 124.0(8) . . ? C10 C9 H9 118 . . ? C8 C9 H9 118 . . ? C9 C10 C11 116.3(8) . . ? C9 C10 C14 121.8(7) . . ? C11 C10 C14 121.8(8) . . ? O11 C11 C12 114.8(7) . . ? O11 C11 C10 124.3(8) . . ? C12 C11 C10 121.0(8) . . ? C11 C12 C13 120.6(8) . . ? C11 C12 C31 117.7(8) . . ? C13 C12 C31 121.7(8) . . ? O13 C13 C8 118.2(8) . . ? O13 C13 C12 121.5(7) . . ? C8 C13 C12 120.2(8) . . ? C10 C14 C15 109.4(6) . . ? C10 C14 C66 114.5(8) . . ? C15 C14 C66 112.8(7) . . ? C10 C14 H14 106.5 . . ? C15 C14 H14 106.5 . . ? C66 C14 H14 106.5 . . ? C20 C15 C16 116.8(7) . . ? C20 C15 C14 122.5(7) . . ? C16 C15 C14 120.7(7) . . ? C17 C16 C15 123.7(7) . . ? C17 C16 H16 118.1 . . ? C15 C16 H16 118.1 . . ? C16 C17 C18 116.7(6) . . ? C16 C17 C21 121.5(7) . . ? C18 C17 C21 121.8(7) . . ? O18 C18 C17 122.3(6) . . ? O18 C18 C19 116.7(7) . . ? C17 C18 C19 121.0(7) . . ? C20 C19 C18 119.8(7) . . ? C20 C19 C33 123.3(7) . . ? C18 C19 C33 116.9(8) . . ? C19 C20 O20 119.3(7) . . ? C19 C20 C15 121.9(7) . . ? O20 C20 C15 118.4(7) . . ? C17 C21 C22 110.1(5) . . ? C17 C21 C67 112.5(6) . . ? C22 C21 C67 113.4(6) . . ? C17 C21 H21 106.8 . . ? C22 C21 H21 106.8 . . ? C67 C21 H21 106.8 . . ? C23 C22 C27 117.8(6) . . ? C23 C22 C21 122.4(6) . . ? C27 C22 C21 119.8(6) . . ? C24 C23 C22 123.4(6) . . ? C24 C23 H23 118.3 . . ? C22 C23 H23 118.3 . . ? C23 C24 C25 117.4(6) . . ? C23 C24 C28 122.8(6) . . ? C25 C24 C28 119.8(6) . . ? O25 C25 C24 124.8(6) . . ? O25 C25 C26 114.1(6) . . ? C24 C25 C26 121.0(6) . . ? C27 C26 C25 119.1(6) . . ? C27 C26 C35 122.3(6) . . ? C25 C26 C35 118.6(6) . . ? O27 C27 C26 121.1(6) . . ? O27 C27 C22 117.5(6) . . ? C26 C27 C22 121.3(6) . . ? C1 C28 C24 111.2(5) . . ? C1 C28 C68 112.1(6) . . ? C24 C28 C68 112.7(6) . . ? C1 C28 H28 106.8 . . ? C24 C28 H28 106.8 . . ? C68 C28 H28 106.8 . . ? N30 C29 C5 109.2(6) . . ? N30 C29 H29A 109.8 . . ? C5 C29 H29A 109.8 . . ? N30 C29 H29B 109.8 . . ? C5 C29 H29B 109.8 . . ? H29A C29 H29B 108.3 . . ? C12 C31 N32 110.9(6) . . ? C12 C31 H31A 109.5 . . ? N32 C31 H31A 109.5 . . ? C12 C31 H31B 109.5 . . ? N32 C31 H31B 109.5 . . ? H31A C31 H31B 108.1 . . ? C19 C33 N34 109.2(6) . . ? C19 C33 H33A 109.8 . . ? N34 C33 H33A 109.8 . . ? C19 C33 H33B 109.8 . . ? N34 C33 H33B 109.8 . . ? H33A C33 H33B 108.3 . . ? C26 C35 N36 110.8(5) . . ? C26 C35 H35A 109.5 . . ? N36 C35 H35A 109.5 . . ? C26 C35 H35B 109.5 . . ? N36 C35 H35B 109.5 . . ? H35A C35 H35B 108.1 . . ? N30 C37 C38 112.5(7) . . ? N30 C37 H37A 109.1 . . ? C38 C37 H37A 109.1 . . ? N30 C37 H37B 109.1 . . ? C38 C37 H37B 109.1 . . ? H37A C37 H37B 107.8 . . ? C43 C38 C39 120.2(9) . . ? C43 C38 C37 121.5(7) . . ? C39 C38 C37 118.3(8) . . ? C38 C39 C40 118.0(10) . . ? C38 C39 H39 121 . . ? C40 C39 H39 121 . . ? C39 C40 C41 121.8(9) . . ? C39 C40 H40 119.1 . . ? C41 C40 H40 119.1 . . ? C42 C41 C40 119.0(9) . . ? C42 C41 H41 120.5 . . ? C40 C41 H41 120.5 . . ? C41 C42 C43 119.9(10) . . ? C41 C42 H42 120.1 . . ? C43 C42 H42 120.1 . . ? C38 C43 C42 121.1(9) . . ? C38 C43 H43 119.4 . . ? C42 C43 H43 119.4 . . ? N32 C44 C45 114.4(7) . . ? N32 C44 H44A 108.7 . . ? C45 C44 H44A 108.7 . . ? N32 C44 H44B 108.7 . . ? C45 C44 H44B 108.7 . . ? H44A C44 H44B 107.6 . . ? C46 C45 C50 119.9(8) . . ? C46 C45 C44 119.9(9) . . ? C50 C45 C44 120.1(9) . . ? C45 C46 C47 121.1(10) . . ? C45 C46 H46 119.4 . . ? C47 C46 H46 119.4 . . ? C48 C47 C46 118.5(10) . . ? C48 C47 H47 120.8 . . ? C46 C47 H47 120.8 . . ? C47 C48 C49 121.0(8) . . ? C47 C48 H48 119.5 . . ? C49 C48 H48 119.5 . . ? C48 C49 C50 120.2(8) . . ? C48 C49 H49 119.9 . . ? C50 C49 H49 119.9 . . ? C45 C50 C49 119.2(8) . . ? C45 C50 H50 120.4 . . ? C49 C50 H50 120.4 . . ? N34 C51 C52 111.7(7) . . ? N34 C51 H51A 109.3 . . ? C52 C51 H51A 109.3 . . ? N34 C51 H51B 109.3 . . ? C52 C51 H51B 109.3 . . ? H51A C51 H51B 107.9 . . ? C57 C52 C53 120.7(10) . . ? C57 C52 C51 120.7(9) . . ? C53 C52 C51 118.6(9) . . ? C54 C53 C52 120.2(12) . . ? C54 C53 H53 119.9 . . ? C52 C53 H53 119.9 . . ? C55 C54 C53 119.6(12) . . ? C55 C54 H54 120.2 . . ? C53 C54 H54 120.2 . . ? C54 C55 C56 121.1(13) . . ? C54 C55 H55 119.5 . . ? C56 C55 H55 119.5 . . ? C55 C56 C57 119.2(15) . . ? C55 C56 H56 120.4 . . ? C57 C56 H56 120.4 . . ? C52 C57 C56 119.0(13) . . ? C52 C57 H57 120.5 . . ? C56 C57 H57 120.5 . . ? N36 C58 C59 113.1(7) . . ? N36 C58 H58A 109 . . ? C59 C58 H58A 109 . . ? N36 C58 H58B 109 . . ? C59 C58 H58B 109 . . ? H58A C58 H58B 107.8 . . ? C60 C59 C64 117.1(10) . . ? C60 C59 C58 122.1(8) . . ? C64 C59 C58 120.7(8) . . ? C59 C60 C61 121.8(9) . . ? C59 C60 H60 119.1 . . ? C61 C60 H60 119.1 . . ? C62 C61 C60 120.3(10) . . ? C62 C61 H61 119.8 . . ? C60 C61 H61 119.8 . . ? C63 C62 C61 119.6(11) . . ? C63 C62 H62 120.2 . . ? C61 C62 H62 120.2 . . ? C62 C63 C64 120.7(11) . . ? C62 C63 H63 119.6 . . ? C64 C63 H63 119.6 . . ? C59 C64 C63 120.1(10) . . ? C59 C64 H64 119.9 . . ? C63 C64 H64 119.9 . . ? C7 C65 H65A 109.5 . . ? C7 C65 H65B 109.5 . . ? H65A C65 H65B 109.5 . . ? C7 C65 H65C 109.5 . . ? H65A C65 H65C 109.5 . . ? H65B C65 H65C 109.5 . . ? C14 C66 H66A 109.5 . . ? C14 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? C14 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C21 C67 H67A 109.5 . . ? C21 C67 H67B 109.5 . . ? H67A C67 H67B 109.5 . . ? C21 C67 H67C 109.5 . . ? H67A C67 H67C 109.5 . . ? H67B C67 H67C 109.5 . . ? C28 C68 H68A 109.5 . . ? C28 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? C28 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 109.5 . . ? Cl3A C1A Cl2A 108.7(5) . . ? Cl3A C1A Cl1A 112.2(6) . . ? Cl2A C1A Cl1A 109.1(6) . . ? Cl3A C1A ClA' 106.9(10) . . ? Cl2A C1A ClA' 118.0(8) . . ? Cl3A C1A Br1A 108.1(4) . . ? Cl2A C1A Br1A 108.4(4) . . ? Cl1A C1A Br1A 110.3(7) . . ? Cl3A C1A BrA' 107.7(5) . . ? Cl2A C1A BrA' 111.5(5) . . ? ClA' C1A BrA' 103.6(8) . . ? Cl2B C1B Cl3B 110.0(4) . . ? Cl2B C1B Cl1B 110.9(3) . . ? Cl3B C1B Cl1B 114.3(4) . . ? Cl2B C1B Br1B 106.7(3) . . ? Cl3B C1B Br1B 105.6(3) . . ? Cl1B C1B Br1B 109.0(3) . . ? Cl1C C1C Cl3C 113.1(5) . . ? Cl1C C1C Cl2C 108.9(5) . . ? Cl3C C1C Cl2C 112.5(5) . . ? Cl1C C1C Br1C 108.0(4) . . ? Cl3C C1C Br1C 107.5(4) . . ? Cl2C C1C Br1C 106.5(4) . . ? Cl3D C1D Cl2D 107.0(9) . . ? Cl3D C1D Cl1D 113.7(10) . . ? Cl2D C1D Cl1D 105.8(7) . . ? Cl3D C1D Br1D 109.5(8) . . ? Cl2D C1D Br1D 110.1(8) . . ? Cl1D C1D Br1D 110.7(8) . . ? Cl2' C1D' Cl1' 109.1(7) . . ? Cl2' C1D' Cl3' 108.5(8) . . ? Cl1' C1D' Cl3' 112.8(8) . . ? Cl2' C1D' BrD' 108.2(6) . . ? Cl1' C1D' BrD' 111.4(6) . . ? Cl3' C1D' BrD' 106.7(6) . . ? Cl2E C1E Cl3E 114.9(7) . . ? Cl2E C1E Cl1E 113.0(7) . . ? Cl3E C1E Cl1E 111.4(7) . . ? Cl2E C1E Br1E 107.8(5) . . ? Cl3E C1E Br1E 106.4(8) . . ? Cl1E C1E Br1E 102.3(7) . . ? O3W Cl1E C1E 90.9(8) . . ? Cl2F C1F Cl3F 109.3(8) . . ? Cl2F C1F Cl1F 109.7(11) . . ? Cl3F C1F Cl1F 115.6(10) . . ? Cl2F C1F H1F 107.3 . . ? Cl3F C1F H1F 107.3 . . ? Cl1F C1F H1F 107.3 . . ? Cl6F C1F' Cl5F 111.2(7) . . ? Cl6F C1F' Cl4F 111.2(5) . . ? Cl5F C1F' Cl4F 112.1(7) . . ? Cl6F C1F' H1F' 107.3 . . ? Cl5F C1F' H1F' 107.3 . . ? Cl4F C1F' H1F' 107.3 . . ? Cl4F Cl4F C1F' 162.5(9) 2_556 . ? Cl4F Cl4F Cl5F 163.1(8) 2_556 . ? Cl4F Cl4F Cl6F 132.2(7) 2_556 . ? Cl5F Cl4F Cl6F 59.9(2) . . ? 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 C6 C1 C2 C3 1.6(10) . . . . ? C28 C1 C2 C3 179.4(6) . . . . ? C1 C2 C3 C4 -3.4(11) . . . . ? C1 C2 C3 C7 178.6(7) . . . . ? C2 C3 C4 O4 -177.6(7) . . . . ? C7 C3 C4 O4 0.4(12) . . . . ? C2 C3 C4 C5 2.4(11) . . . . ? C7 C3 C4 C5 -179.7(7) . . . . ? O4 C4 C5 C6 -179.6(6) . . . . ? C3 C4 C5 C6 0.5(11) . . . . ? O4 C4 C5 C29 4.9(10) . . . . ? C3 C4 C5 C29 -175.0(7) . . . . ? C4 C5 C6 O6 -179.1(6) . . . . ? C29 C5 C6 O6 -3.9(11) . . . . ? C4 C5 C6 C1 -2.5(10) . . . . ? C29 C5 C6 C1 172.7(7) . . . . ? C2 C1 C6 O6 178.3(6) . . . . ? C28 C1 C6 O6 0.4(9) . . . . ? C2 C1 C6 C5 1.5(10) . . . . ? C28 C1 C6 C5 -176.4(6) . . . . ? C4 C3 C7 C8 -99.6(9) . . . . ? C2 C3 C7 C8 78.3(9) . . . . ? C4 C3 C7 C65 131.9(8) . . . . ? C2 C3 C7 C65 -50.2(10) . . . . ? C3 C7 C8 C9 -95.9(9) . . . . ? C65 C7 C8 C9 31.9(10) . . . . ? C3 C7 C8 C13 81.4(9) . . . . ? C65 C7 C8 C13 -150.8(7) . . . . ? C13 C8 C9 C10 0.5(11) . . . . ? C7 C8 C9 C10 177.9(7) . . . . ? C8 C9 C10 C11 1.3(11) . . . . ? C8 C9 C10 C14 178.8(7) . . . . ? C9 C10 C11 O11 178.1(7) . . . . ? C14 C10 C11 O11 0.6(12) . . . . ? C9 C10 C11 C12 -0.7(11) . . . . ? C14 C10 C11 C12 -178.2(7) . . . . ? O11 C11 C12 C13 179.5(7) . . . . ? C10 C11 C12 C13 -1.6(12) . . . . ? O11 C11 C12 C31 -1.9(11) . . . . ? C10 C11 C12 C31 177.0(7) . . . . ? C9 C8 C13 O13 -178.6(6) . . . . ? C7 C8 C13 O13 4.0(10) . . . . ? C9 C8 C13 C12 -2.9(10) . . . . ? C7 C8 C13 C12 179.7(7) . . . . ? C11 C12 C13 O13 179.0(7) . . . . ? C31 C12 C13 O13 0.5(12) . . . . ? C11 C12 C13 C8 3.5(11) . . . . ? C31 C12 C13 C8 -175.0(7) . . . . ? C9 C10 C14 C15 101.7(9) . . . . ? C11 C10 C14 C15 -80.9(9) . . . . ? C9 C10 C14 C66 -26.0(10) . . . . ? C11 C10 C14 C66 151.4(7) . . . . ? C10 C14 C15 C20 97.3(9) . . . . ? C66 C14 C15 C20 -134.1(9) . . . . ? C10 C14 C15 C16 -82.1(9) . . . . ? C66 C14 C15 C16 46.5(11) . . . . ? C20 C15 C16 C17 0.9(11) . . . . ? C14 C15 C16 C17 -179.7(7) . . . . ? C15 C16 C17 C18 -2.4(11) . . . . ? C15 C16 C17 C21 179.4(7) . . . . ? C16 C17 C18 O18 -179.7(7) . . . . ? C21 C17 C18 O18 -1.6(11) . . . . ? C16 C17 C18 C19 2.1(11) . . . . ? C21 C17 C18 C19 -179.8(6) . . . . ? O18 C18 C19 C20 -178.5(7) . . . . ? C17 C18 C19 C20 -0.3(11) . . . . ? O18 C18 C19 C33 2.6(10) . . . . ? C17 C18 C19 C33 -179.2(7) . . . . ? C18 C19 C20 O20 -174.9(7) . . . . ? C33 C19 C20 O20 4.0(12) . . . . ? C18 C19 C20 C15 -1.4(12) . . . . ? C33 C19 C20 C15 177.4(8) . . . . ? C16 C15 C20 C19 1.2(12) . . . . ? C14 C15 C20 C19 -178.3(7) . . . . ? C16 C15 C20 O20 174.6(7) . . . . ? C14 C15 C20 O20 -4.8(12) . . . . ? C16 C17 C21 C22 78.6(8) . . . . ? C18 C17 C21 C22 -99.5(8) . . . . ? C16 C17 C21 C67 -49.0(9) . . . . ? C18 C17 C21 C67 133.0(7) . . . . ? C17 C21 C22 C23 -96.9(7) . . . . ? C67 C21 C22 C23 30.1(9) . . . . ? C17 C21 C22 C27 80.2(8) . . . . ? C67 C21 C22 C27 -152.8(6) . . . . ? C27 C22 C23 C24 1.0(9) . . . . ? C21 C22 C23 C24 178.1(6) . . . . ? C22 C23 C24 C25 -0.3(9) . . . . ? C22 C23 C24 C28 -179.3(6) . . . . ? C23 C24 C25 O25 177.7(6) . . . . ? C28 C24 C25 O25 -3.4(9) . . . . ? C23 C24 C25 C26 0.5(9) . . . . ? C28 C24 C25 C26 179.5(6) . . . . ? O25 C25 C26 C27 -178.8(6) . . . . ? C24 C25 C26 C27 -1.4(9) . . . . ? O25 C25 C26 C35 1.2(9) . . . . ? C24 C25 C26 C35 178.6(6) . . . . ? C25 C26 C27 O27 178.8(6) . . . . ? C35 C26 C27 O27 -1.3(10) . . . . ? C25 C26 C27 C22 2.1(9) . . . . ? C35 C26 C27 C22 -177.9(6) . . . . ? C23 C22 C27 O27 -178.6(5) . . . . ? C21 C22 C27 O27 4.1(8) . . . . ? C23 C22 C27 C26 -1.9(9) . . . . ? C21 C22 C27 C26 -179.1(6) . . . . ? C2 C1 C28 C24 -78.3(8) . . . . ? C6 C1 C28 C24 99.5(8) . . . . ? C2 C1 C28 C68 48.9(9) . . . . ? C6 C1 C28 C68 -133.3(7) . . . . ? C23 C24 C28 C1 100.3(7) . . . . ? C25 C24 C28 C1 -78.7(8) . . . . ? C23 C24 C28 C68 -26.6(8) . . . . ? C25 C24 C28 C68 154.5(6) . . . . ? C37 N30 C29 C5 -169.7(6) . . . . ? C4 C5 C29 N30 68.8(9) . . . . ? C6 C5 C29 N30 -106.4(8) . . . . ? C11 C12 C31 N32 77.9(9) . . . . ? C13 C12 C31 N32 -103.5(9) . . . . ? C44 N32 C31 C12 172.6(7) . . . . ? C20 C19 C33 N34 -105.0(9) . . . . ? C18 C19 C33 N34 73.9(9) . . . . ? C51 N34 C33 C19 -175.4(7) . . . . ? C27 C26 C35 N36 -116.4(7) . . . . ? C25 C26 C35 N36 63.6(8) . . . . ? C58 N36 C35 C26 168.7(6) . . . . ? C29 N30 C37 C38 62.7(9) . . . . ? N30 C37 C38 C43 -101.7(9) . . . . ? N30 C37 C38 C39 78.6(10) . . . . ? C43 C38 C39 C40 1.8(15) . . . . ? C37 C38 C39 C40 -178.5(9) . . . . ? C38 C39 C40 C41 -1.7(17) . . . . ? C39 C40 C41 C42 1.9(18) . . . . ? C40 C41 C42 C43 -2.1(17) . . . . ? C39 C38 C43 C42 -2.2(15) . . . . ? C37 C38 C43 C42 178.2(9) . . . . ? C41 C42 C43 C38 2.3(17) . . . . ? C31 N32 C44 C45 63.8(11) . . . . ? N32 C44 C45 C46 -90.9(11) . . . . ? N32 C44 C45 C50 92.2(11) . . . . ? C50 C45 C46 C47 -1.6(15) . . . . ? C44 C45 C46 C47 -178.4(9) . . . . ? C45 C46 C47 C48 2.1(16) . . . . ? C46 C47 C48 C49 -1.6(16) . . . . ? C47 C48 C49 C50 0.5(15) . . . . ? C46 C45 C50 C49 0.4(14) . . . . ? C44 C45 C50 C49 177.3(8) . . . . ? C48 C49 C50 C45 0.1(14) . . . . ? C33 N34 C51 C52 56.9(10) . . . . ? N34 C51 C52 C57 -105.2(12) . . . . ? N34 C51 C52 C53 77.2(12) . . . . ? C57 C52 C53 C54 2(2) . . . . ? C51 C52 C53 C54 180.0(12) . . . . ? C52 C53 C54 C55 1(2) . . . . ? C53 C54 C55 C56 -1(2) . . . . ? C54 C55 C56 C57 -2(3) . . . . ? C53 C52 C57 C56 -5(2) . . . . ? C51 C52 C57 C56 177.2(13) . . . . ? C55 C56 C57 C52 5(3) . . . . ? C35 N36 C58 C59 50.2(9) . . . . ? N36 C58 C59 C60 66.6(12) . . . . ? N36 C58 C59 C64 -109.2(11) . . . . ? C64 C59 C60 C61 -1.7(16) . . . . ? C58 C59 C60 C61 -177.6(9) . . . . ? C59 C60 C61 C62 0.1(18) . . . . ? C60 C61 C62 C63 5(2) . . . . ? C61 C62 C63 C64 -8(3) . . . . ? C60 C59 C64 C63 -1(2) . . . . ? C58 C59 C64 C63 174.7(13) . . . . ? C62 C63 C64 C59 6(3) . . . . ? Cl2E C1E Cl1E O3W -68.9(10) . . . . ? Cl3E C1E Cl1E O3W 62.2(12) . . . . ? Br1E C1E Cl1E O3W 175.5(10) . . . . ? Cl6F C1F' Cl4F Cl4F 47(3) . . . 2_556 ? Cl5F C1F' Cl4F Cl4F 172(2) . . . 2_556 ? Cl6F C1F' Cl4F Cl5F -125.2(14) . . . . ? Cl5F C1F' Cl4F Cl6F 125.2(14) . . . . ? Cl6F C1F' Cl5F Cl4F 125.2(12) . . . . ? Cl5F C1F' Cl6F Cl4F -125.7(14) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 967821' ####################################################################### # # 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_6_7_3 _audit_creation_date 2013-07-31T19:33:43-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_melting_point ? _chemical_formula_moiety 'C72 H88 N4 O8, 3 (C Br Cl3), 4(Br)' _chemical_formula_sum 'C75 H88 Br7 Cl9 N4 O8' _chemical_formula_weight 2051.91 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.3897(13) _cell_length_b 13.9188(3) _cell_length_c 27.2095(12) _cell_angle_alpha 90 _cell_angle_beta 128.814(7) _cell_angle_gamma 90 _cell_volume 8672.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 123.0(1) _cell_measurement_reflns_used 8924 _cell_measurement_theta_min 3.854 _cell_measurement_theta_max 75.954 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.571 _exptl_crystal_F_000 4112 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 6.858 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.68646 _exptl_absorpt_correction_T_max 1.00000 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123.0(1) _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator mirror _diffrn_detector_area_resol_mean 5.1977 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_unetI/netI 0.0295 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_number 13872 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.480 _diffrn_reflns_theta_max 66.995 _diffrn_reflns_theta_full 67.684 _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_Laue_measured_fraction_full 0.973 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_point_group_measured_fraction_full 0.973 _diffrn_reflns_point_group_measured_fraction_max 0.988 _reflns_number_total 7651 _reflns_number_gt 6898 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlisPro, Agilent Technologies, 2013' _computing_cell_refinement 'CrysAlisPro, Agilent Technologies, 2013' _computing_data_reduction 'CrysAlisPro, Agilent Technologies, 2013' _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'MERCURY (Macrae et al., 2006)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0836P)^2^+72.8678P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7651 _refine_ls_number_parameters 480 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1579 _refine_ls_wR_factor_gt 0.1519 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.585 _refine_diff_density_min -2.035 _refine_diff_density_rms 0.123 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group N16 N 0.36167(17) 0.6337(3) 0.2265(2) 0.0283(8) Uani 1 d . . H16A H 0.4042 0.6332 0.2488 0.034 Uiso 1 calc . . H16B H 0.3418 0.6502 0.1818 0.034 Uiso 1 calc . . N18 N 0.37115(16) 0.6795(3) 0.00672(18) 0.0241(8) Uani 1 d . . H18A H 0.3692 0.6512 0.0388 0.029 Uiso 1 calc . . H18B H 0.4125 0.6949 0.0278 0.029 Uiso 1 calc . . O3 O 0.30610(12) 0.8033(2) 0.14669(13) 0.0227(6) Uani 1 d . . H3 H 0.3031 0.8226 0.1155 0.034 Uiso 1 calc . . O5 O 0.55591(13) 0.8079(2) 0.12910(13) 0.0219(6) Uani 1 d . . H5 H 0.5489 0.7499 0.1304 0.033 Uiso 1 calc . . O11 O 0.44170(12) 0.8395(2) 0.02607(13) 0.0210(6) Uani 1 d . . H11 H 0.4784 0.8388 0.0514 0.032 Uiso 1 calc . . O13 O 0.28957(12) 0.8472(2) 0.04143(13) 0.0217(6) Uani 1 d . . H13 H 0.2616 0.8727 0.0074 0.033 Uiso 1 calc . . C1 C 0.58575(16) 0.9844(3) 0.24430(19) 0.0167(8) Uani 1 d . . H1 H 0.572 1.046 0.2445 0.02 Uiso 1 calc . . C2 C 0.36992(16) 0.9429(3) 0.19809(18) 0.0158(8) Uani 1 d . . C3 C 0.35024(16) 0.8528(3) 0.19976(19) 0.0182(8) Uani 1 d . . C4 C 0.37364(16) 0.8055(3) 0.25668(19) 0.0178(8) Uani 1 d . . C5 C 0.58100(16) 0.8505(3) 0.18688(18) 0.0170(8) Uani 1 d . . C6 C 0.56045(16) 0.9413(3) 0.18664(18) 0.0148(7) Uani 1 d . . C7 C 0.34440(16) 0.9939(3) 0.13602(18) 0.0177(8) Uani 1 d . . H7 H 0.3017 0.9789 0.1063 0.021 Uiso 1 calc . . C8 C 0.37108(16) 0.9535(3) 0.10685(18) 0.0169(8) Uani 1 d . . C9 C 0.42575(16) 0.9829(3) 0.12746(18) 0.0159(7) Uani 1 d . . H9 H 0.4466 1.0285 0.1607 0.019 Uiso 1 calc . . C10 C 0.45153(16) 0.9490(3) 0.10190(18) 0.0160(8) Uani 1 d . . C11 C 0.42115(17) 0.8798(3) 0.05490(18) 0.0171(8) Uani 1 d . . C12 C 0.36631(17) 0.8464(3) 0.03313(18) 0.0176(8) Uani 1 d . . C13 C 0.34204(16) 0.8842(3) 0.05935(18) 0.0175(8) Uani 1 d . . C14 C 0.51062(16) 0.9877(3) 0.12465(17) 0.0151(7) Uani 1 d . . H14 H 0.5152 0.968 0.0926 0.018 Uiso 1 calc . . C15 C 0.34861(18) 0.7108(3) 0.25478(19) 0.0205(8) Uani 1 d . . H15A H 0.3058 0.7171 0.2296 0.025 Uiso 1 calc . . H15B H 0.3651 0.6919 0.2982 0.025 Uiso 1 calc . . C17 C 0.33653(17) 0.7709(3) -0.0171(2) 0.0217(8) Uani 1 d . . H17A H 0.2971 0.7587 -0.0304 0.026 Uiso 1 calc . . H17B H 0.3321 0.7938 -0.0543 0.026 Uiso 1 calc . . C19 C 0.3430(2) 0.5340(3) 0.2292(2) 0.0304(10) Uani 1 d . . H19A H 0.3669 0.5135 0.2738 0.037 Uiso 1 calc . . H19B H 0.3508 0.4888 0.2071 0.037 Uiso 1 calc . . C20 C 0.27923(19) 0.5281(3) 0.1997(2) 0.0252(9) Uani 1 d . . C21 C 0.2356(2) 0.5306(4) 0.1343(2) 0.0315(10) Uani 1 d . . H21 H 0.2458 0.5373 0.1076 0.038 Uiso 1 calc . . C22 C 0.1774(2) 0.5235(4) 0.1085(2) 0.0361(11) Uani 1 d . . H22 H 0.1478 0.526 0.064 0.043 Uiso 1 calc . . C23 C 0.1622(2) 0.5128(4) 0.1472(3) 0.0383(12) Uani 1 d . . H23 H 0.1223 0.508 0.1293 0.046 Uiso 1 calc . . C24 C 0.2047(2) 0.5090(4) 0.2112(3) 0.0433(13) Uani 1 d . . H24 H 0.1942 0.5006 0.2376 0.052 Uiso 1 calc . . C25 C 0.2633(2) 0.5174(4) 0.2378(2) 0.0360(11) Uani 1 d . . H25 H 0.2925 0.5159 0.2823 0.043 Uiso 1 calc . . C26 C 0.3507(2) 0.6055(3) -0.0437(2) 0.0293(10) Uani 1 d . . H26A H 0.3093 0.59 -0.0651 0.035 Uiso 1 calc . . H26B H 0.3738 0.5459 -0.0236 0.035 Uiso 1 calc . . C27 C 0.3567(2) 0.6390(3) -0.0920(3) 0.0317(11) Uani 1 d . . C28 C 0.4100(3) 0.6295(4) -0.0808(3) 0.0418(13) Uani 1 d . . H28 H 0.4428 0.6024 -0.0423 0.05 Uiso 1 calc . . C29 C 0.4147(3) 0.6596(5) -0.1260(4) 0.0515(16) Uani 1 d . . H29 H 0.4509 0.6525 -0.1183 0.062 Uiso 1 calc . . C30 C 0.3682(3) 0.6992(5) -0.1814(3) 0.0528(16) Uani 1 d . . H30 H 0.3722 0.7196 -0.2119 0.063 Uiso 1 calc . . C31 C 0.3154(3) 0.7095(5) -0.1933(3) 0.0508(15) Uani 1 d . . H31 H 0.2832 0.7381 -0.2315 0.061 Uiso 1 calc . . C32 C 0.3098(2) 0.6780(4) -0.1491(3) 0.0392(12) Uani 1 d . . H32 H 0.273 0.6831 -0.158 0.047 Uiso 1 calc . . C33 C 0.35024(18) 1.1039(3) 0.1431(2) 0.0210(8) Uani 1 d . . H33A H 0.3389 1.125 0.1688 0.025 Uiso 1 calc . . H33B H 0.3917 1.1215 0.1661 0.025 Uiso 1 calc . . C34 C 0.3132(2) 1.1571(4) 0.0806(2) 0.0291(10) Uani 1 d . . H34A H 0.2725 1.1331 0.0547 0.035 Uiso 1 calc . . H34B H 0.3283 1.1443 0.0574 0.035 Uiso 1 calc . . C35 C 0.3138(2) 1.2648(4) 0.0907(3) 0.0392(12) Uani 1 d . . H35A H 0.2992 1.2774 0.1142 0.059 Uiso 1 calc . . H35B H 0.2886 1.2973 0.0497 0.059 Uiso 1 calc . . H35C H 0.3538 1.2891 0.1147 0.059 Uiso 1 calc . . C36 C 0.51243(18) 1.0982(3) 0.12687(19) 0.0194(8) Uani 1 d . . H36A H 0.5064 1.1203 0.157 0.023 Uiso 1 calc . . H36B H 0.5517 1.1198 0.1429 0.023 Uiso 1 calc . . C37 C 0.46662(19) 1.1456(3) 0.0629(2) 0.0248(9) Uani 1 d . . H37A H 0.4273 1.1253 0.0472 0.03 Uiso 1 calc . . H37B H 0.4691 1.2162 0.0685 0.03 Uiso 1 calc . . C38 C 0.4739(2) 1.1207(4) 0.0135(2) 0.0369(12) Uani 1 d . . H38A H 0.514 1.1348 0.0304 0.055 Uiso 1 calc . . H38B H 0.4466 1.1591 -0.0246 0.055 Uiso 1 calc . . H38C H 0.4657 1.0523 0.003 0.055 Uiso 1 calc . . Br1 Br 0.32904(2) 0.58512(5) 0.08306(3) 0.04088(17) Uani 1 d . . Br2 Br 0.49018(3) 0.59593(4) 0.39309(4) 0.0614(2) Uani 1 d . . C1A C 0.3365(2) 0.6704(4) 0.4251(3) 0.0330(10) Uani 1 d . . Br1A Br 0.39958(2) 0.63180(4) 0.42469(3) 0.03510(16) Uani 1 d . . Cl1A Cl 0.35638(6) 0.65124(11) 0.50034(7) 0.0444(3) Uani 1 d . . Cl2A Cl 0.31991(6) 0.79330(10) 0.40350(8) 0.0506(4) Uani 1 d . . Cl3A Cl 0.27412(5) 0.60012(9) 0.36858(6) 0.0373(3) Uani 1 d . . C1B C 0.5 0.37361(19) 0.25 0.0388(17) Uani 1 d . . Br1B Br 0.43750(14) 0.4509(3) 0.18048(15) 0.0746(11) Uani 0.5 d A 1 Cl1' Cl 0.44139(10) 0.4458(2) 0.18907(16) 0.0207(6) Uani 0.65 d A 2 Cl1B Cl 0.52679(11) 0.29953(18) 0.22075(10) 0.0792(8) Uani 0.85 d A . 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 N16 0.0264(19) 0.0233(19) 0.042(2) -0.0049(16) 0.0244(18) -0.0071(15) N18 0.0222(17) 0.0224(18) 0.0290(19) -0.0013(15) 0.0166(16) -0.0018(14) O3 0.0177(14) 0.0306(16) 0.0168(13) -0.0007(12) 0.0094(12) -0.0086(12) O5 0.0241(15) 0.0205(14) 0.0187(14) -0.0038(11) 0.0124(12) 0.0019(12) O11 0.0179(13) 0.0271(15) 0.0224(14) -0.0050(12) 0.0147(12) -0.0032(12) O13 0.0123(13) 0.0332(16) 0.0174(13) 0.0027(12) 0.0082(11) -0.0042(12) C1 0.0123(17) 0.0195(19) 0.0223(19) -0.0017(16) 0.0129(16) -0.0018(15) C2 0.0113(17) 0.0212(19) 0.0191(19) 0.0033(15) 0.0116(16) 0.0038(14) C3 0.0115(17) 0.025(2) 0.0187(19) -0.0023(16) 0.0101(16) -0.0035(15) C4 0.0138(17) 0.021(2) 0.0200(19) 0.0011(16) 0.0115(16) -0.0006(15) C5 0.0153(18) 0.022(2) 0.0183(18) -0.0026(15) 0.0126(16) -0.0024(15) C6 0.0105(17) 0.0205(19) 0.0163(18) -0.0002(15) 0.0099(15) -0.0016(14) C7 0.0125(17) 0.027(2) 0.0159(18) 0.0028(16) 0.0097(15) 0.0018(15) C8 0.0149(18) 0.022(2) 0.0153(18) 0.0043(15) 0.0102(16) 0.0030(15) C9 0.0150(18) 0.0175(18) 0.0168(18) 0.0020(15) 0.0107(16) -0.0004(15) C10 0.0119(17) 0.0178(19) 0.0170(18) 0.0028(15) 0.0085(15) -0.0001(14) C11 0.0171(18) 0.022(2) 0.0159(18) 0.0013(15) 0.0120(16) 0.0001(15) C12 0.0162(18) 0.0192(19) 0.0165(18) -0.0003(15) 0.0097(16) -0.0033(15) C13 0.0113(17) 0.024(2) 0.0158(18) 0.0025(15) 0.0078(15) -0.0017(15) C14 0.0146(18) 0.0176(19) 0.0141(17) -0.0010(14) 0.0095(15) -0.0029(15) C15 0.0194(19) 0.024(2) 0.0203(19) 0.0001(16) 0.0134(17) -0.0036(16) C17 0.0182(19) 0.022(2) 0.023(2) -0.0023(17) 0.0124(17) -0.0019(16) C19 0.025(2) 0.023(2) 0.038(3) 0.0029(19) 0.018(2) -0.0029(18) C20 0.026(2) 0.018(2) 0.032(2) 0.0001(17) 0.0183(19) -0.0062(17) C21 0.033(2) 0.030(2) 0.033(2) 0.005(2) 0.021(2) -0.008(2) C22 0.029(2) 0.034(3) 0.034(3) 0.006(2) 0.014(2) -0.008(2) C23 0.029(2) 0.035(3) 0.050(3) -0.003(2) 0.024(2) -0.008(2) C24 0.047(3) 0.051(3) 0.051(3) -0.016(3) 0.040(3) -0.020(3) C25 0.038(3) 0.041(3) 0.031(2) -0.006(2) 0.022(2) -0.014(2) C26 0.033(2) 0.023(2) 0.038(3) -0.0075(19) 0.025(2) -0.0056(19) C27 0.037(3) 0.024(2) 0.048(3) -0.015(2) 0.034(2) -0.0100(19) C28 0.039(3) 0.040(3) 0.061(3) -0.012(3) 0.038(3) -0.008(2) C29 0.054(4) 0.050(3) 0.082(5) -0.021(3) 0.058(4) -0.018(3) C30 0.078(4) 0.045(3) 0.069(4) -0.018(3) 0.062(4) -0.022(3) C31 0.068(4) 0.053(4) 0.046(3) 0.000(3) 0.042(3) 0.005(3) C32 0.041(3) 0.045(3) 0.041(3) -0.004(2) 0.030(3) 0.003(2) C33 0.0193(19) 0.024(2) 0.023(2) 0.0045(17) 0.0148(17) 0.0046(16) C34 0.028(2) 0.033(2) 0.027(2) 0.0101(19) 0.018(2) 0.0072(19) C35 0.046(3) 0.034(3) 0.036(3) 0.011(2) 0.025(2) 0.008(2) C36 0.0200(19) 0.019(2) 0.0217(19) 0.0005(16) 0.0145(17) -0.0032(16) C37 0.026(2) 0.022(2) 0.032(2) 0.0057(17) 0.020(2) 0.0028(17) C38 0.044(3) 0.044(3) 0.033(3) 0.016(2) 0.030(2) 0.015(2) Br1 0.0297(3) 0.0600(4) 0.0371(3) 0.0232(3) 0.0229(2) 0.0141(2) Br2 0.0326(3) 0.0325(3) 0.1157(6) -0.0175(3) 0.0448(4) -0.0057(2) C1A 0.034(2) 0.032(3) 0.045(3) -0.001(2) 0.031(2) 0.000(2) Br1A 0.0339(3) 0.0350(3) 0.0442(3) 0.0068(2) 0.0282(3) 0.0007(2) Cl1A 0.0524(8) 0.0509(8) 0.0447(7) -0.0137(6) 0.0376(6) -0.0119(6) Cl2A 0.0440(7) 0.0286(6) 0.0772(10) 0.0044(6) 0.0370(7) 0.0053(5) Cl3A 0.0309(6) 0.0437(7) 0.0423(6) -0.0057(5) 0.0254(5) -0.0053(5) C1B 0.033(4) 0.029(4) 0.045(4) 0 0.020(3) 0 Br1B 0.0744(18) 0.079(2) 0.0537(15) 0.0109(12) 0.0320(13) -0.0025(14) Cl1' 0.0109(10) 0.0178(12) 0.0254(12) 0.0059(9) 0.0075(9) 0.0012(8) Cl1B 0.0865(15) 0.0806(15) 0.0589(11) -0.0135(11) 0.0399(11) 0.0382(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N16 C15 1.504(6) . ? N16 C19 1.511(6) . ? N16 H16A 0.99 . ? N16 H16B 0.99 . ? N18 C17 1.499(5) . ? N18 C26 1.506(6) . ? N18 H18A 0.99 . ? N18 H18B 0.99 . ? O3 C3 1.376(5) . ? O3 H3 0.84 . ? O5 C5 1.383(5) . ? O5 H5 0.84 . ? O11 C11 1.374(5) . ? O11 H11 0.84 . ? O13 C13 1.393(5) . ? O13 H13 0.84 . ? C1 C6 1.383(5) . ? C1 C2 1.389(6) 2_655 ? C1 H1 0.95 . ? C2 C1 1.389(6) 2_655 ? C2 C3 1.393(6) . ? C2 C7 1.527(5) . ? C3 C4 1.403(6) . ? C4 C5 1.400(6) 2_655 ? C4 C15 1.495(6) . ? C5 C6 1.399(6) . ? C5 C4 1.400(6) 2_655 ? C6 C14 1.520(5) . ? C7 C8 1.530(5) . ? C7 C33 1.538(6) . ? C7 H7 1 . ? C8 C9 1.391(5) . ? C8 C13 1.394(6) . ? C9 C10 1.393(5) . ? C9 H9 0.95 . ? C10 C11 1.390(6) . ? C10 C14 1.530(5) . ? C11 C12 1.402(6) . ? C12 C13 1.390(6) . ? C12 C17 1.497(6) . ? C14 C36 1.539(5) . ? C14 H14 1 . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C19 C20 1.510(6) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 C25 1.389(7) . ? C20 C21 1.396(7) . ? C21 C22 1.385(7) . ? C21 H21 0.95 . ? C22 C23 1.386(8) . ? C22 H22 0.95 . ? C23 C24 1.367(8) . ? C23 H23 0.95 . ? C24 C25 1.392(8) . ? C24 H24 0.95 . ? C25 H25 0.95 . ? C26 C27 1.506(7) . ? C26 H26A 0.99 . ? C26 H26B 0.99 . ? C27 C32 1.387(8) . ? C27 C28 1.401(7) . ? C28 C29 1.386(9) . ? C28 H28 0.95 . ? C29 C30 1.365(10) . ? C29 H29 0.95 . ? C30 C31 1.380(9) . ? C30 H30 0.95 . ? C31 C32 1.384(8) . ? C31 H31 0.95 . ? C32 H32 0.95 . ? C33 C34 1.517(6) . ? C33 H33A 0.99 . ? C33 H33B 0.99 . ? C34 C35 1.523(7) . ? C34 H34A 0.99 . ? C34 H34B 0.99 . ? C35 H35A 0.98 . ? C35 H35B 0.98 . ? C35 H35C 0.98 . ? C36 C37 1.530(6) . ? C36 H36A 0.99 . ? C36 H36B 0.99 . ? C37 C38 1.526(6) . ? C37 H37A 0.99 . ? C37 H37B 0.99 . ? C38 H38A 0.98 . ? C38 H38B 0.98 . ? C38 H38C 0.98 . ? C1A Cl1A 1.762(5) . ? C1A Cl3A 1.773(5) . ? C1A Cl2A 1.775(5) . ? C1A Br1A 1.937(5) . ? C1B Cl1B 1.761(2) 2_655 ? C1B Cl1B 1.761(2) . ? C1B Cl1' 1.7733(10) 2_655 ? C1B Cl1' 1.7733(10) . ? C1B Br1B 1.9371(10) . ? C1B Br1B 1.9372(10) 2_655 ? 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 C15 N16 C19 114.4(4) . . ? C15 N16 H16A 108.7 . . ? C19 N16 H16A 108.7 . . ? C15 N16 H16B 108.7 . . ? C19 N16 H16B 108.7 . . ? H16A N16 H16B 107.6 . . ? C17 N18 C26 114.3(3) . . ? C17 N18 H18A 108.7 . . ? C26 N18 H18A 108.7 . . ? C17 N18 H18B 108.7 . . ? C26 N18 H18B 108.7 . . ? H18A N18 H18B 107.6 . . ? C3 O3 H3 109.5 . . ? C5 O5 H5 109.5 . . ? C11 O11 H11 109.5 . . ? C13 O13 H13 109.5 . . ? C6 C1 C2 123.8(4) . 2_655 ? C6 C1 H1 118.1 . . ? C2 C1 H1 118.1 2_655 . ? C1 C2 C3 116.9(4) 2_655 . ? C1 C2 C7 121.2(4) 2_655 . ? C3 C2 C7 121.9(4) . . ? O3 C3 C2 123.6(4) . . ? O3 C3 C4 114.3(4) . . ? C2 C3 C4 122.1(4) . . ? C5 C4 C3 118.2(4) 2_655 . ? C5 C4 C15 122.8(4) 2_655 . ? C3 C4 C15 119.0(4) . . ? O5 C5 C6 117.4(3) . . ? O5 C5 C4 121.2(4) . 2_655 ? C6 C5 C4 121.4(4) . 2_655 ? C1 C6 C5 117.6(4) . . ? C1 C6 C14 122.2(4) . . ? C5 C6 C14 120.2(3) . . ? C2 C7 C8 110.2(3) . . ? C2 C7 C33 112.7(3) . . ? C8 C7 C33 112.2(3) . . ? C2 C7 H7 107.1 . . ? C8 C7 H7 107.1 . . ? C33 C7 H7 107.1 . . ? C9 C8 C13 117.3(4) . . ? C9 C8 C7 121.4(4) . . ? C13 C8 C7 121.4(3) . . ? C10 C9 C8 123.5(4) . . ? C10 C9 H9 118.3 . . ? C8 C9 H9 118.3 . . ? C11 C10 C9 117.2(3) . . ? C11 C10 C14 121.9(3) . . ? C9 C10 C14 120.9(3) . . ? O11 C11 C10 123.3(3) . . ? O11 C11 C12 115.1(4) . . ? C10 C11 C12 121.6(4) . . ? C13 C12 C11 118.8(4) . . ? C13 C12 C17 122.7(4) . . ? C11 C12 C17 118.5(4) . . ? O13 C13 C12 119.5(4) . . ? O13 C13 C8 118.7(4) . . ? C12 C13 C8 121.6(4) . . ? C6 C14 C10 111.0(3) . . ? C6 C14 C36 113.3(3) . . ? C10 C14 C36 111.7(3) . . ? C6 C14 H14 106.8 . . ? C10 C14 H14 106.8 . . ? C36 C14 H14 106.8 . . ? C4 C15 N16 111.6(3) . . ? C4 C15 H15A 109.3 . . ? N16 C15 H15A 109.3 . . ? C4 C15 H15B 109.3 . . ? N16 C15 H15B 109.3 . . ? H15A C15 H15B 108 . . ? N18 C17 C12 110.6(3) . . ? N18 C17 H17A 109.5 . . ? C12 C17 H17A 109.5 . . ? N18 C17 H17B 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? N16 C19 C20 113.1(4) . . ? N16 C19 H19A 109 . . ? C20 C19 H19A 109 . . ? N16 C19 H19B 109 . . ? C20 C19 H19B 109 . . ? H19A C19 H19B 107.8 . . ? C25 C20 C21 118.9(4) . . ? C25 C20 C19 119.8(4) . . ? C21 C20 C19 121.3(4) . . ? C22 C21 C20 120.0(5) . . ? C22 C21 H21 120 . . ? C20 C21 H21 120 . . ? C21 C22 C23 120.3(5) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 120.0(5) . . ? C24 C23 H23 120 . . ? C22 C23 H23 120 . . ? C23 C24 C25 120.2(5) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C20 C25 C24 120.5(5) . . ? C20 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? N18 C26 C27 112.7(4) . . ? N18 C26 H26A 109 . . ? C27 C26 H26A 109 . . ? N18 C26 H26B 109 . . ? C27 C26 H26B 109 . . ? H26A C26 H26B 107.8 . . ? C32 C27 C28 118.2(5) . . ? C32 C27 C26 121.4(4) . . ? C28 C27 C26 120.4(5) . . ? C29 C28 C27 119.9(6) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C30 C29 C28 120.9(5) . . ? C30 C29 H29 119.5 . . ? C28 C29 H29 119.5 . . ? C29 C30 C31 120.1(6) . . ? C29 C30 H30 120 . . ? C31 C30 H30 120 . . ? C30 C31 C32 119.5(6) . . ? C30 C31 H31 120.2 . . ? C32 C31 H31 120.2 . . ? C27 C32 C31 121.4(5) . . ? C27 C32 H32 119.3 . . ? C31 C32 H32 119.3 . . ? C34 C33 C7 113.6(4) . . ? C34 C33 H33A 108.9 . . ? C7 C33 H33A 108.9 . . ? C34 C33 H33B 108.9 . . ? C7 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? C33 C34 C35 111.1(4) . . ? C33 C34 H34A 109.4 . . ? C35 C34 H34A 109.4 . . ? C33 C34 H34B 109.4 . . ? C35 C34 H34B 109.4 . . ? H34A C34 H34B 108 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C37 C36 C14 113.7(3) . . ? C37 C36 H36A 108.8 . . ? C14 C36 H36A 108.8 . . ? C37 C36 H36B 108.8 . . ? C14 C36 H36B 108.8 . . ? H36A C36 H36B 107.7 . . ? C38 C37 C36 113.3(4) . . ? C38 C37 H37A 108.9 . . ? C36 C37 H37A 108.9 . . ? C38 C37 H37B 108.9 . . ? C36 C37 H37B 108.9 . . ? H37A C37 H37B 107.7 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? Cl1A C1A Cl3A 109.5(3) . . ? Cl1A C1A Cl2A 110.6(3) . . ? Cl3A C1A Cl2A 108.9(3) . . ? Cl1A C1A Br1A 110.0(3) . . ? Cl3A C1A Br1A 108.4(3) . . ? Cl2A C1A Br1A 109.3(2) . . ? Cl1B C1B Cl1B 108.3(2) 2_655 . ? Cl1B C1B Cl1' 110.88(16) 2_655 2_655 ? Cl1B C1B Cl1' 107.86(15) . 2_655 ? Cl1B C1B Cl1' 107.86(15) 2_655 . ? Cl1B C1B Cl1' 110.88(16) . . ? Cl1' C1B Cl1' 111.0(3) 2_655 . ? Cl1B C1B Br1B 110.33(16) 2_655 . ? Cl1B C1B Br1B 107.61(16) . . ? Cl1B C1B Br1B 107.61(16) 2_655 2_655 ? Cl1B C1B Br1B 110.33(16) . 2_655 ? Br1B C1B Br1B 112.6(3) . 2_655 ? 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 C1 C2 C3 O3 179.0(3) 2_655 . . . ? C7 C2 C3 O3 -1.2(6) . . . . ? C1 C2 C3 C4 0.1(6) 2_655 . . . ? C7 C2 C3 C4 179.9(3) . . . . ? O3 C3 C4 C5 179.7(3) . . . 2_655 ? C2 C3 C4 C5 -1.3(6) . . . 2_655 ? O3 C3 C4 C15 -1.5(5) . . . . ? C2 C3 C4 C15 177.5(4) . . . . ? C2 C1 C6 C5 0.1(6) 2_655 . . . ? C2 C1 C6 C14 177.9(3) 2_655 . . . ? O5 C5 C6 C1 -179.5(3) . . . . ? C4 C5 C6 C1 -1.3(5) 2_655 . . . ? O5 C5 C6 C14 2.6(5) . . . . ? C4 C5 C6 C14 -179.2(3) 2_655 . . . ? C1 C2 C7 C8 99.8(4) 2_655 . . . ? C3 C2 C7 C8 -79.9(4) . . . . ? C1 C2 C7 C33 -26.4(5) 2_655 . . . ? C3 C2 C7 C33 153.9(4) . . . . ? C2 C7 C8 C9 -80.6(5) . . . . ? C33 C7 C8 C9 45.9(5) . . . . ? C2 C7 C8 C13 98.2(4) . . . . ? C33 C7 C8 C13 -135.3(4) . . . . ? C13 C8 C9 C10 2.0(6) . . . . ? C7 C8 C9 C10 -179.2(4) . . . . ? C8 C9 C10 C11 -2.3(6) . . . . ? C8 C9 C10 C14 177.2(4) . . . . ? C9 C10 C11 O11 -179.3(4) . . . . ? C14 C10 C11 O11 1.2(6) . . . . ? C9 C10 C11 C12 1.2(6) . . . . ? C14 C10 C11 C12 -178.3(4) . . . . ? O11 C11 C12 C13 -179.3(4) . . . . ? C10 C11 C12 C13 0.2(6) . . . . ? O11 C11 C12 C17 1.1(5) . . . . ? C10 C11 C12 C17 -179.3(4) . . . . ? C11 C12 C13 O13 -175.6(3) . . . . ? C17 C12 C13 O13 3.9(6) . . . . ? C11 C12 C13 C8 -0.6(6) . . . . ? C17 C12 C13 C8 178.9(4) . . . . ? C9 C8 C13 O13 174.6(3) . . . . ? C7 C8 C13 O13 -4.3(6) . . . . ? C9 C8 C13 C12 -0.4(6) . . . . ? C7 C8 C13 C12 -179.3(4) . . . . ? C1 C6 C14 C10 -96.3(4) . . . . ? C5 C6 C14 C10 81.5(4) . . . . ? C1 C6 C14 C36 30.4(5) . . . . ? C5 C6 C14 C36 -151.8(3) . . . . ? C11 C10 C14 C6 -101.1(4) . . . . ? C9 C10 C14 C6 79.4(4) . . . . ? C11 C10 C14 C36 131.3(4) . . . . ? C9 C10 C14 C36 -48.2(5) . . . . ? C5 C4 C15 N16 -113.2(4) 2_655 . . . ? C3 C4 C15 N16 68.0(5) . . . . ? C19 N16 C15 C4 174.0(4) . . . . ? C26 N18 C17 C12 -169.2(3) . . . . ? C13 C12 C17 N18 -115.3(4) . . . . ? C11 C12 C17 N18 64.2(5) . . . . ? C15 N16 C19 C20 55.0(5) . . . . ? N16 C19 C20 C25 -107.7(5) . . . . ? N16 C19 C20 C21 74.0(6) . . . . ? C25 C20 C21 C22 0.6(7) . . . . ? C19 C20 C21 C22 178.9(5) . . . . ? C20 C21 C22 C23 -0.7(8) . . . . ? C21 C22 C23 C24 -0.1(8) . . . . ? C22 C23 C24 C25 1.0(9) . . . . ? C21 C20 C25 C24 0.3(8) . . . . ? C19 C20 C25 C24 -178.1(5) . . . . ? C23 C24 C25 C20 -1.1(9) . . . . ? C17 N18 C26 C27 63.1(5) . . . . ? N18 C26 C27 C32 -97.3(5) . . . . ? N18 C26 C27 C28 84.1(5) . . . . ? C32 C27 C28 C29 0.6(8) . . . . ? C26 C27 C28 C29 179.3(5) . . . . ? C27 C28 C29 C30 0.4(9) . . . . ? C28 C29 C30 C31 -0.2(9) . . . . ? C29 C30 C31 C32 -1.1(10) . . . . ? C28 C27 C32 C31 -1.9(8) . . . . ? C26 C27 C32 C31 179.4(5) . . . . ? C30 C31 C32 C27 2.2(9) . . . . ? C2 C7 C33 C34 -166.3(3) . . . . ? C8 C7 C33 C34 68.5(4) . . . . ? C7 C33 C34 C35 171.6(4) . . . . ? C6 C14 C36 C37 173.5(3) . . . . ? C10 C14 C36 C37 -60.1(4) . . . . ? C14 C36 C37 C38 -61.6(5) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 967822'