# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_mb250710 _database_code_depnum_ccdc_archive 'CCDC 864483' #TrackingRef '9247_web_deposit_cif_file_0_MiquelBarcelo-Oliver_1327507456.compound 1.cif' _audit_creation_date 2010-07-26T14:47:41-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1-hexyl-5-methylpyrimidine-2,4(1H,3H)-dione ; _chemical_name_common N1-hexylthymine _chemical_melting_point ? _chemical_formula_moiety 'C11 H18 N2 O2' _chemical_formula_sum 'C11 H18 N2 O2' _chemical_formula_weight 210.27 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6964(8) _cell_length_b 17.7522(4) _cell_length_c 22.7940(12) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4732.9(4) _cell_formula_units_Z 16 _cell_measurement_reflns_used 5139 _cell_measurement_theta_min 2.4566 _cell_measurement_theta_max 32.7587 _cell_measurement_temperature 183(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.18 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1824 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_min 0.87269 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur Ruby' _diffrn_measurement_method '/o oscillation scan' _diffrn_detector_area_resol_mean 10.4498 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_unetI/netI 0.0293 _diffrn_reflns_number 16777 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.68 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 4483 _reflns_number_gt 2464 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlis RED (Oxford, 2007)' _computing_cell_refinement 'CrysAlis RED (Oxford, 2007)' _computing_data_reduction 'CrysAlis RED (Oxford, 2007)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1086P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4483 _refine_ls_number_parameters 313 _refine_ls_number_restraints 138 _refine_ls_R_factor_all 0.1085 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1982 _refine_ls_wR_factor_gt 0.1795 _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.038 _refine_ls_shift/su_mean 0.004 _refine_diff_density_max 0.337 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # 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' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.65724(4) 0.48806(3) 0.07064(3) 0.04457(18) Uani 1 1 d . . . C2 C 0.55266(5) 0.52288(4) 0.06896(3) 0.0466(2) Uani 1 1 d . . . O2 O 0.46213(4) 0.48975(3) 0.06422(2) 0.05996(18) Uani 1 1 d . . . N3 N 0.55756(4) 0.60048(3) 0.07367(3) 0.04459(18) Uani 1 1 d . . . H3 H 0.4918 0.6245 0.0726 0.054 Uiso 1 1 calc R . . C4 C 0.65413(5) 0.64428(4) 0.07982(3) 0.0413(2) Uani 1 1 d . . . O4 O 0.64594(3) 0.71345(2) 0.08305(2) 0.05344(16) Uani 1 1 d . . . C5 C 0.76051(5) 0.60350(3) 0.08181(3) 0.0412(2) Uani 1 1 d . . . C51 C 0.87019(5) 0.64696(4) 0.08747(4) 0.0561(3) Uani 1 1 d . . . H51A H 0.8731 0.6713 0.126 0.084 Uiso 1 1 calc R . . H51B H 0.8738 0.6854 0.0567 0.084 Uiso 1 1 calc R . . H51C H 0.9351 0.6125 0.0834 0.084 Uiso 1 1 calc R . . C6 C 0.75638(5) 0.52828(4) 0.07739(3) 0.0435(2) Uani 1 1 d . . . H6 H 0.8264 0.5012 0.079 0.052 Uiso 1 1 calc R . . C7 C 0.66394(6) 0.40471(4) 0.06684(4) 0.0562(3) Uani 1 1 d . . . H7A H 0.5927 0.3854 0.0488 0.067 Uiso 1 1 calc R . . H7B H 0.7284 0.3907 0.0409 0.067 Uiso 1 1 calc R . . C8 C 0.67996(7) 0.36853(4) 0.12415(4) 0.0732(3) Uani 1 1 d U B . H8A H 0.7472 0.3913 0.1437 0.088 Uiso 1 1 calc R . . H8B H 0.6967 0.3144 0.118 0.088 Uiso 1 1 calc R . . C9 C 0.57708(10) 0.37560(5) 0.16452(5) 0.0992(4) Uani 1 1 d DU . . H9A H 0.5661 0.4294 0.1743 0.119 Uiso 1 1 calc R A 1 H9B H 0.5082 0.3585 0.1431 0.119 Uiso 1 1 calc R A 1 C10 C 0.58606(13) 0.33300(7) 0.21879(6) 0.1468(5) Uani 0.7 1 d PDU B 1 H10A H 0.6598 0.3472 0.237 0.176 Uiso 0.7 1 calc PR B 1 H10B H 0.5927 0.2793 0.2076 0.176 Uiso 0.7 1 calc PR B 1 C11 C 0.49780(18) 0.33707(11) 0.26611(8) 0.1436(8) Uani 0.7 1 d PDU B 1 H11A H 0.4765 0.3901 0.2738 0.172 Uiso 0.7 1 calc PR B 1 H11B H 0.5276 0.3147 0.3029 0.172 Uiso 0.7 1 calc PR B 1 C12 C 0.39263(17) 0.29213(11) 0.24404(9) 0.1498(8) Uani 0.7 1 d PDU B 1 H12A H 0.4155 0.2402 0.2353 0.225 Uiso 0.7 1 calc PR B 1 H12B H 0.3625 0.3158 0.2084 0.225 Uiso 0.7 1 calc PR B 1 H12C H 0.3334 0.2919 0.2744 0.225 Uiso 0.7 1 calc PR B 1 C10' C 0.58606(13) 0.33300(7) 0.21879(6) 0.1468(5) Uani 0.3 1 d PDU B 2 H10C H 0.6411 0.3571 0.2459 0.176 Uiso 0.3 1 calc PR B 2 H10D H 0.6114 0.2808 0.2109 0.176 Uiso 0.3 1 calc PR B 2 C11' C 0.4572(3) 0.3338(2) 0.24652(15) 0.1107(12) Uani 0.3 1 d PDU B 2 H11C H 0.4395 0.3843 0.2625 0.133 Uiso 0.3 1 calc PR B 2 H11D H 0.4004 0.3218 0.2157 0.133 Uiso 0.3 1 calc PR B 2 C12' C 0.4524(4) 0.2770(3) 0.29368(17) 0.1542(15) Uani 0.3 1 d PDU B 2 H12D H 0.4325 0.2278 0.2769 0.231 Uiso 0.3 1 calc PR B 2 H12E H 0.3945 0.2916 0.3225 0.231 Uiso 0.3 1 calc PR B 2 H12F H 0.5272 0.2736 0.3129 0.231 Uiso 0.3 1 calc PR B 2 N21 N 0.33989(4) 0.90872(3) 0.06514(3) 0.04215(17) Uani 1 1 d . . . C22 C 0.44491(5) 0.87377(4) 0.06672(3) 0.0443(2) Uani 1 1 d . . . O22 O 0.53488(3) 0.90828(3) 0.06574(3) 0.06103(18) Uani 1 1 d . . . N23 N 0.44056(4) 0.79636(3) 0.06916(3) 0.04523(18) Uani 1 1 d . . . H23 H 0.5065 0.7727 0.0714 0.054 Uiso 1 1 calc R . . C24 C 0.34381(5) 0.75193(4) 0.06850(3) 0.0410(2) Uani 1 1 d . . . O24 O 0.35220(3) 0.68276(2) 0.07048(2) 0.05361(17) Uani 1 1 d . . . C25 C 0.23669(5) 0.79199(4) 0.06496(3) 0.0413(2) Uani 1 1 d . . . C251 C 0.12823(5) 0.74716(4) 0.06267(4) 0.0523(2) Uani 1 1 d . . . H25A H 0.0639 0.7808 0.0542 0.078 Uiso 1 1 calc R . . H25B H 0.1158 0.7224 0.1006 0.078 Uiso 1 1 calc R . . H25C H 0.1341 0.709 0.0318 0.078 Uiso 1 1 calc R . . C26 C 0.24012(5) 0.86750(4) 0.06433(3) 0.0420(2) Uani 1 1 d . . . H26 H 0.1697 0.8941 0.0633 0.05 Uiso 1 1 calc R . . C27 C 0.33660(6) 0.99177(4) 0.06661(4) 0.0514(2) Uani 1 1 d . . . H27A H 0.2616 1.0091 0.0517 0.062 Uiso 1 1 calc R . . H27B H 0.3965 1.0118 0.0402 0.062 Uiso 1 1 calc R . . C28 C 0.35487(6) 1.02329(4) 0.12733(4) 0.0687(3) Uani 1 1 d U D . H28A H 0.3545 1.079 0.125 0.082 Uiso 1 1 calc R . . H28B H 0.4313 1.0076 0.1414 0.082 Uiso 1 1 calc R . . C29 C 0.26597(8) 0.99865(6) 0.17193(4) 0.0958(4) Uani 1 1 d DU . . H29A H 0.2715 0.9433 0.1767 0.115 Uiso 1 1 calc R C 3 H29B H 0.1893 1.0098 0.1558 0.115 Uiso 1 1 calc R C 3 C30 C 0.27484(13) 1.03471(8) 0.23239(6) 0.1446(5) Uani 0.75 1 d PDU D 3 H30A H 0.2381 1.0005 0.261 0.174 Uiso 0.75 1 calc PR D 3 H30B H 0.3568 1.0379 0.2429 0.174 Uiso 0.75 1 calc PR D 3 C31 C 0.22672(15) 1.10651(9) 0.23940(8) 0.1387(7) Uani 0.75 1 d PDU D 3 H31A H 0.2554 1.1408 0.2085 0.166 Uiso 0.75 1 calc PR D 3 H31B H 0.2485 1.1276 0.278 0.166 Uiso 0.75 1 calc PR D 3 C32 C 0.08625(16) 1.09927(12) 0.23489(9) 0.1599(8) Uani 0.75 1 d PDU D 3 H32A H 0.0564 1.0769 0.2711 0.24 Uiso 0.75 1 calc PR D 3 H32B H 0.0661 1.0671 0.2015 0.24 Uiso 0.75 1 calc PR D 3 H32C H 0.0529 1.1494 0.2294 0.24 Uiso 0.75 1 calc PR D 3 C30' C 0.27484(13) 1.03471(8) 0.23239(6) 0.1446(5) Uani 0.25 1 d PDU D 4 H30C H 0.3177 1 0.2583 0.174 Uiso 0.25 1 calc PR D 4 H30D H 0.3206 1.0814 0.2287 0.174 Uiso 0.25 1 calc PR D 4 C31' C 0.1674(4) 1.0536(2) 0.26124(17) 0.1160(13) Uani 0.25 1 d PDU D 4 H31C H 0.1793 1.0599 0.304 0.139 Uiso 0.25 1 calc PR D 4 H31D H 0.1104 1.0132 0.2549 0.139 Uiso 0.25 1 calc PR D 4 C32' C 0.1241(5) 1.1310(3) 0.2326(3) 0.1791(17) Uani 0.25 1 d PDU D 4 H32D H 0.1696 1.1729 0.2479 0.269 Uiso 0.25 1 calc PR D 4 H32E H 0.0434 1.1388 0.2423 0.269 Uiso 0.25 1 calc PR D 4 H32F H 0.1329 1.1285 0.1898 0.269 Uiso 0.25 1 calc PR D 4 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0269(3) 0.0226(3) 0.0843(4) -0.0059(3) 0.0026(3) 0.0005(2) C2 0.0277(3) 0.0305(3) 0.0817(5) -0.0043(4) 0.0053(3) -0.0021(3) O2 0.0251(2) 0.0351(3) 0.1197(4) -0.0034(3) 0.0012(3) -0.0090(2) N3 0.0192(2) 0.0268(3) 0.0878(4) -0.0019(3) -0.0003(3) 0.0013(2) C4 0.0248(3) 0.0275(3) 0.0715(5) -0.0022(3) 0.0004(3) 0.0000(3) O4 0.0275(2) 0.0230(2) 0.1098(4) -0.0032(3) -0.0044(2) 0.00220(19) C5 0.0218(3) 0.0288(3) 0.0728(5) -0.0026(3) -0.0003(3) 0.0004(3) C51 0.0225(3) 0.0356(4) 0.1104(6) -0.0017(4) -0.0047(4) -0.0016(3) C6 0.0215(3) 0.0303(3) 0.0787(5) -0.0036(3) -0.0008(3) 0.0038(3) C7 0.0389(3) 0.0226(3) 0.1070(6) -0.0148(4) 0.0087(4) 0.0006(3) C8 0.0756(5) 0.0284(4) 0.1156(7) 0.0028(5) 0.0073(5) 0.0074(4) C9 0.1277(8) 0.0580(5) 0.1120(7) 0.0058(6) 0.0190(6) 0.0087(6) C10 0.1972(11) 0.1022(8) 0.1411(9) 0.0178(7) 0.0448(8) 0.0092(9) C11 0.1971(16) 0.1144(13) 0.1195(12) -0.0087(11) 0.0318(12) 0.0175(12) C12 0.1600(14) 0.1442(15) 0.1452(15) 0.0225(13) 0.0398(13) 0.0222(12) C10' 0.1972(11) 0.1022(8) 0.1411(9) 0.0178(7) 0.0448(8) 0.0092(9) C11' 0.122(2) 0.114(2) 0.096(2) -0.0070(17) -0.0063(16) -0.012(2) C12' 0.157(3) 0.178(3) 0.127(2) 0.0346(19) 0.012(2) 0.004(2) N21 0.0254(2) 0.0243(3) 0.0768(4) -0.0018(3) -0.0009(3) 0.0008(2) C22 0.0257(3) 0.0279(3) 0.0795(5) -0.0017(4) -0.0016(3) -0.0009(3) O22 0.0240(2) 0.0344(2) 0.1246(5) 0.0031(3) -0.0031(3) -0.0084(2) N23 0.0193(2) 0.0271(3) 0.0893(4) -0.0026(3) -0.0012(3) 0.0014(2) C24 0.0250(3) 0.0289(3) 0.0692(5) -0.0043(3) 0.0026(3) 0.0005(3) O24 0.0262(2) 0.0242(2) 0.1104(4) -0.0026(3) 0.0013(2) 0.0010(2) C25 0.0238(3) 0.0283(3) 0.0718(5) -0.0029(3) 0.0006(3) 0.0005(3) C251 0.0235(3) 0.0339(4) 0.0994(6) 0.0008(4) 0.0003(4) 0.0005(3) C26 0.0208(3) 0.0325(3) 0.0727(5) -0.0022(3) 0.0011(3) 0.0025(3) C27 0.0338(3) 0.0236(3) 0.0969(6) 0.0037(4) -0.0025(4) -0.0002(3) C28 0.0564(4) 0.0336(4) 0.1161(7) -0.0155(5) -0.0147(5) -0.0007(4) C29 0.0827(6) 0.1017(7) 0.1031(7) -0.0374(6) 0.0032(6) -0.0028(6) C30 0.1383(10) 0.1570(10) 0.1385(9) -0.0491(8) -0.0190(8) 0.0199(8) C31 0.1612(14) 0.1086(10) 0.1464(13) -0.0452(10) -0.0033(12) -0.0047(11) C32 0.1386(12) 0.1677(15) 0.1735(15) -0.0480(13) 0.0287(12) 0.0130(12) C30' 0.1383(10) 0.1570(10) 0.1385(9) -0.0491(8) -0.0190(8) 0.0199(8) C31' 0.141(2) 0.115(2) 0.092(2) -0.0265(18) 0.0122(18) 0.002(2) C32' 0.184(3) 0.170(3) 0.184(3) 0.011(2) 0.004(3) 0.037(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.3704(8) . ? N1 C2 1.3711(8) . ? N1 C7 1.4843(8) . ? C2 O2 1.2160(8) . ? C2 N3 1.3828(8) . ? N3 C4 1.3785(8) . ? N3 H3 0.88 . ? C4 O4 1.2338(8) . ? C4 C5 1.4402(8) . ? C5 C6 1.3400(9) . ? C5 C51 1.5023(9) . ? C51 H51A 0.98 . ? C51 H51B 0.98 . ? C51 H51C 0.98 . ? C6 H6 0.95 . ? C7 C8 1.4676(12) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 C9 1.5201(14) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.4537(17) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.495(2) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.550(3) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C11' C12' 1.475(5) . ? C11' H11C 0.99 . ? C11' H11D 0.99 . ? C12' H12D 0.98 . ? C12' H12E 0.98 . ? C12' H12F 0.98 . ? N21 C22 1.3766(8) . ? N21 C26 1.3776(8) . ? N21 C27 1.4751(8) . ? C22 O22 1.2178(7) . ? C22 N23 1.3763(8) . ? N23 C24 1.3795(8) . ? N23 H23 0.88 . ? C24 O24 1.2326(8) . ? C24 C25 1.4429(8) . ? C25 C26 1.3410(9) . ? C25 C251 1.4985(8) . ? C251 H25A 0.98 . ? C251 H25B 0.98 . ? C251 H25C 0.98 . ? C26 H26 0.95 . ? C27 C28 1.5080(12) . ? C27 H27A 0.99 . ? C27 H27B 0.99 . ? C28 C29 1.5185(13) . ? C28 H28A 0.99 . ? C28 H28B 0.99 . ? C29 C30 1.5231(16) . ? C29 H29A 0.99 . ? C29 H29B 0.99 . ? C30 C31 1.403(2) . ? C30 H30A 0.99 . ? C30 H30B 0.99 . ? C31 C32 1.651(3) . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? C32 H32A 0.98 . ? C32 H32B 0.98 . ? C32 H32C 0.98 . ? C31' C32' 1.603(6) . ? C31' H31C 0.99 . ? C31' H31D 0.99 . ? C32' H32D 0.98 . ? C32' H32E 0.98 . ? C32' H32F 0.98 . ? 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 C6 N1 C2 121.55(5) . . ? C6 N1 C7 118.77(5) . . ? C2 N1 C7 119.66(5) . . ? O2 C2 N1 124.15(6) . . ? O2 C2 N3 121.65(6) . . ? N1 C2 N3 114.20(5) . . ? C4 N3 C2 127.14(5) . . ? C4 N3 H3 116.4 . . ? C2 N3 H3 116.4 . . ? O4 C4 N3 120.26(5) . . ? O4 C4 C5 124.43(6) . . ? N3 C4 C5 115.32(5) . . ? C6 C5 C4 117.86(5) . . ? C6 C5 C51 123.29(6) . . ? C4 C5 C51 118.84(5) . . ? C5 C51 H51A 109.5 . . ? C5 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C5 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C5 C6 N1 123.93(6) . . ? C5 C6 H6 118 . . ? N1 C6 H6 118 . . ? C8 C7 N1 113.03(6) . . ? C8 C7 H7A 109 . . ? N1 C7 H7A 109 . . ? C8 C7 H7B 109 . . ? N1 C7 H7B 109 . . ? H7A C7 H7B 107.8 . . ? C7 C8 C9 113.68(7) . . ? C7 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? C7 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C10 C9 C8 114.52(10) . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? C8 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C9 C10 C11 122.61(13) . . ? C9 C10 H10A 106.7 . . ? C11 C10 H10A 106.7 . . ? C9 C10 H10B 106.7 . . ? C11 C10 H10B 106.7 . . ? H10A C10 H10B 106.6 . . ? C10 C11 C12 106.80(15) . . ? C10 C11 H11A 110.4 . . ? C12 C11 H11A 110.4 . . ? C10 C11 H11B 110.4 . . ? C12 C11 H11B 110.4 . . ? H11A C11 H11B 108.6 . . ? C12' C11' H11C 110.1 . . ? C12' C11' H11D 110.1 . . ? H11C C11' H11D 108.4 . . ? C11' C12' H12D 109.5 . . ? C11' C12' H12E 109.5 . . ? H12D C12' H12E 109.5 . . ? C11' C12' H12F 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? C22 N21 C26 121.11(5) . . ? C22 N21 C27 118.24(5) . . ? C26 N21 C27 120.61(5) . . ? O22 C22 N23 122.34(6) . . ? O22 C22 N21 122.94(6) . . ? N23 C22 N21 114.72(5) . . ? C22 N23 C24 126.92(5) . . ? C22 N23 H23 116.5 . . ? C24 N23 H23 116.5 . . ? O24 C24 N23 120.25(5) . . ? O24 C24 C25 124.21(5) . . ? N23 C24 C25 115.54(6) . . ? C26 C25 C24 117.86(5) . . ? C26 C25 C251 123.77(5) . . ? C24 C25 C251 118.37(6) . . ? C25 C251 H25A 109.5 . . ? C25 C251 H25B 109.5 . . ? H25A C251 H25B 109.5 . . ? C25 C251 H25C 109.5 . . ? H25A C251 H25C 109.5 . . ? H25B C251 H25C 109.5 . . ? C25 C26 N21 123.79(6) . . ? C25 C26 H26 118.1 . . ? N21 C26 H26 118.1 . . ? N21 C27 C28 112.83(6) . . ? N21 C27 H27A 109 . . ? C28 C27 H27A 109 . . ? N21 C27 H27B 109 . . ? C28 C27 H27B 109 . . ? H27A C27 H27B 107.8 . . ? C27 C28 C29 114.23(7) . . ? C27 C28 H28A 108.7 . . ? C29 C28 H28A 108.7 . . ? C27 C28 H28B 108.7 . . ? C29 C28 H28B 108.7 . . ? H28A C28 H28B 107.6 . . ? C28 C29 C30 115.98(9) . . ? C28 C29 H29A 108.3 . . ? C30 C29 H29A 108.3 . . ? C28 C29 H29B 108.3 . . ? C30 C29 H29B 108.3 . . ? H29A C29 H29B 107.4 . . ? C31 C30 C29 117.24(13) . . ? C31 C30 H30A 108 . . ? C29 C30 H30A 108 . . ? C31 C30 H30B 108 . . ? C29 C30 H30B 108 . . ? H30A C30 H30B 107.2 . . ? C30 C31 C32 108.75(14) . . ? C30 C31 H31A 109.9 . . ? C32 C31 H31A 109.9 . . ? C30 C31 H31B 109.9 . . ? C32 C31 H31B 109.9 . . ? H31A C31 H31B 108.3 . . ? C32' C31' H31C 110.4 . . ? C32' C31' H31D 110.4 . . ? H31C C31' H31D 108.6 . . ? 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 N1 C2 O2 -178.48(7) . . . . ? C7 N1 C2 O2 -0.31(11) . . . . ? C6 N1 C2 N3 0.98(10) . . . . ? C7 N1 C2 N3 179.15(6) . . . . ? O2 C2 N3 C4 179.28(7) . . . . ? N1 C2 N3 C4 -0.19(11) . . . . ? C2 N3 C4 O4 179.39(7) . . . . ? C2 N3 C4 C5 -0.41(11) . . . . ? O4 C4 C5 C6 -179.55(7) . . . . ? N3 C4 C5 C6 0.24(10) . . . . ? O4 C4 C5 C51 -0.77(11) . . . . ? N3 C4 C5 C51 179.02(7) . . . . ? C4 C5 C6 N1 0.54(11) . . . . ? C51 C5 C6 N1 -178.18(7) . . . . ? C2 N1 C6 C5 -1.21(11) . . . . ? C7 N1 C6 C5 -179.40(7) . . . . ? C6 N1 C7 C8 77.96(8) . . . . ? C2 N1 C7 C8 -100.27(8) . . . . ? N1 C7 C8 C9 67.94(8) . . . . ? C7 C8 C9 C10 173.35(9) . . . . ? C8 C9 C10 C11 175.40(13) . . . . ? C9 C10 C11 C12 74.06(18) . . . . ? C26 N21 C22 O22 177.79(7) . . . . ? C27 N21 C22 O22 -4.50(11) . . . . ? C26 N21 C22 N23 -1.86(10) . . . . ? C27 N21 C22 N23 175.86(6) . . . . ? O22 C22 N23 C24 -177.70(7) . . . . ? N21 C22 N23 C24 1.94(11) . . . . ? C22 N23 C24 O24 179.42(7) . . . . ? C22 N23 C24 C25 -0.11(11) . . . . ? O24 C24 C25 C26 178.64(7) . . . . ? N23 C24 C25 C26 -1.85(10) . . . . ? O24 C24 C25 C251 -0.89(11) . . . . ? N23 C24 C25 C251 178.62(7) . . . . ? C24 C25 C26 N21 1.97(11) . . . . ? C251 C25 C26 N21 -178.53(7) . . . . ? C22 N21 C26 C25 -0.03(11) . . . . ? C27 N21 C26 C25 -177.69(7) . . . . ? C22 N21 C27 C28 -78.16(8) . . . . ? C26 N21 C27 C28 99.57(7) . . . . ? N21 C27 C28 C29 -60.48(8) . . . . ? C27 C28 C29 C30 -174.68(8) . . . . ? C28 C29 C30 C31 81.99(15) . . . . ? C29 C30 C31 C32 68.83(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 O24 0.88 1.93 2.8123(6) 176.7 . N23 H23 O4 0.88 1.96 2.8350(6) 173.8 . data_pm166b _database_code_depnum_ccdc_archive 'CCDC 864484' #TrackingRef '- compound 3 new.cif' _audit_creation_date 2012-05-25T11:23:21-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H18 N3 O, Br' _chemical_formula_sum 'C10 H18 Br N3 O' _chemical_formula_weight 276.18 _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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6850(10) _cell_length_b 8.004(3) _cell_length_c 12.907(6) _cell_angle_alpha 89.62(5) _cell_angle_beta 84.50(3) _cell_angle_gamma 81.14(3) _cell_volume 679.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 16.5 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.35 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.03 0 0 -1 0.03 0 1 0 0.06 0 -1 0 0.06 1 0 0 0.25 -1 0 0 0.25 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.009 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; a grid of 8 x 8 x 8 = 512 sampling points was used ; _exptl_absorpt_correction_T_min 0.3444 _exptl_absorpt_correction_T_max 0.8375 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.025288 _diffrn_orient_matrix_ub_12 0.057086 _diffrn_orient_matrix_ub_13 0.069721 _diffrn_orient_matrix_ub_21 -0.04774 _diffrn_orient_matrix_ub_22 -0.103415 _diffrn_orient_matrix_ub_23 0.031176 _diffrn_orient_matrix_ub_31 0.14203 _diffrn_orient_matrix_ub_32 -0.045047 _diffrn_orient_matrix_ub_33 0.01497 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled \w scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 -1 0 -1 -1 2 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_unetI/netI 0.0947 _diffrn_reflns_number 2785 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 2661 _reflns_number_gt 1532 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2661 _refine_ls_number_parameters 229 _refine_ls_number_restraints 417 _refine_ls_R_factor_all 0.1309 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1344 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 0.959 _refine_ls_shift/su_max 0.047 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.401 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.094 #----------------------------------------------------------------------------# # 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' 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' Br Br -0.2901 2.4595 '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.27880(7) 0.37201(6) -0.07834(5) 0.0682(2) Uani 1 1 d . . . N1 N 0.1950(5) 0.2067(5) 0.1814(4) 0.0568(11) Uani 1 1 d U . . C2 C 0.3768(7) 0.1049(6) 0.1547(5) 0.0617(15) Uani 1 1 d U A . O2 O 0.5403(5) 0.1462(4) 0.1630(4) 0.0846(13) Uani 1 1 d U . . N3 N 0.3604(5) -0.0526(4) 0.1171(3) 0.0558(12) Uani 1 1 d U . . H3 H 0.4721 -0.1193 0.0996 0.067 Uiso 1 1 calc R A . C4 C 0.1853(6) -0.1126(6) 0.1052(4) 0.0485(13) Uani 1 1 d U A . N4 N 0.1918(6) -0.2619(5) 0.0672(4) 0.0636(13) Uani 1 1 d U . . H4A H 0.3071 -0.3233 0.0494 0.076 Uiso 1 1 calc R A . H4B H 0.0807 -0.3003 0.0595 0.076 Uiso 1 1 calc R . . C5 C 0.0027(6) -0.0020(6) 0.1354(4) 0.0570(14) Uani 1 1 d U . . H5 H -0.1231 -0.0358 0.1304 0.068 Uiso 1 1 calc R A . C6 C 0.0148(6) 0.1516(6) 0.1711(4) 0.0547(14) Uani 1 1 d U A . H6 H -0.1053 0.2246 0.1898 0.066 Uiso 1 1 calc R . . C7 C 0.2003(8) 0.3794(6) 0.2187(5) 0.0699(16) Uani 0.5 1 d PDU A 1 H7A H 0.0997 0.4562 0.1853 0.084 Uiso 0.5 1 calc PR A 1 H7B H 0.3325 0.4091 0.1956 0.084 Uiso 0.5 1 calc PR A 1 C8 C 0.162(3) 0.4097(15) 0.3344(9) 0.092(5) Uani 0.5 1 d PDU A 1 H8A H 0.2589 0.3341 0.371 0.11 Uiso 0.5 1 calc PR A 1 H8B H 0.0256 0.3926 0.3597 0.11 Uiso 0.5 1 calc PR A 1 C9 C 0.193(3) 0.611(2) 0.3506(16) 0.142(7) Uani 0.5 1 d PDU A 1 H9A H 0.1283 0.6781 0.2968 0.17 Uiso 0.5 1 calc PR A 1 H9B H 0.123 0.651 0.4172 0.17 Uiso 0.5 1 calc PR A 1 C10 C 0.371(3) 0.633(2) 0.348(2) 0.139(6) Uani 0.5 1 d PDU A 1 H10A H 0.4316 0.6215 0.2764 0.167 Uiso 0.5 1 calc PR A 1 H10B H 0.4446 0.5462 0.3884 0.167 Uiso 0.5 1 calc PR A 1 C11 C 0.393(3) 0.814(2) 0.3916(16) 0.137(7) Uani 0.5 1 d PDU A 1 H11A H 0.3055 0.8999 0.3565 0.165 Uiso 0.5 1 calc PR A 1 H11B H 0.346 0.8202 0.4652 0.165 Uiso 0.5 1 calc PR A 1 C12 C 0.590(3) 0.848(2) 0.3783(14) 0.155(7) Uani 0.5 1 d PDU A 1 H12A H 0.6736 0.7734 0.4209 0.232 Uiso 0.5 1 calc PR A 1 H12B H 0.5919 0.9631 0.3983 0.232 Uiso 0.5 1 calc PR A 1 H12C H 0.642 0.8314 0.3066 0.232 Uiso 0.5 1 calc PR A 1 C7' C 0.2003(8) 0.3794(6) 0.2187(5) 0.0699(16) Uani 0.25 1 d PDU A 2 H7'1 H 0.0654 0.4446 0.2186 0.084 Uiso 0.25 1 calc PR A 2 H7'2 H 0.2914 0.4322 0.1705 0.084 Uiso 0.25 1 calc PR A 2 C8' C 0.268(5) 0.387(3) 0.3258(14) 0.089(7) Uani 0.25 1 d PDU A 2 H8'1 H 0.4142 0.3846 0.3211 0.107 Uiso 0.25 1 calc PR A 2 H8'2 H 0.2362 0.2891 0.3653 0.107 Uiso 0.25 1 calc PR A 2 C9' C 0.151(4) 0.562(3) 0.385(2) 0.113(7) Uani 0.25 1 d PDU A 2 H9'1 H 0.0905 0.6384 0.3339 0.135 Uiso 0.25 1 calc PR A 2 H9'2 H 0.0417 0.5351 0.4342 0.135 Uiso 0.25 1 calc PR A 2 C10' C 0.265(6) 0.635(3) 0.432(3) 0.146(8) Uani 0.25 1 d PDU A 2 H10C H 0.3992 0.6155 0.3941 0.176 Uiso 0.25 1 calc PR A 2 H10D H 0.2763 0.5838 0.4997 0.176 Uiso 0.25 1 calc PR A 2 C11' C 0.200(7) 0.833(3) 0.448(3) 0.162(11) Uani 0.25 1 d PDU A 2 H11C H 0.2683 0.8904 0.3922 0.195 Uiso 0.25 1 calc PR A 2 H11D H 0.0551 0.8606 0.4437 0.195 Uiso 0.25 1 calc PR A 2 C12' C 0.245(8) 0.892(5) 0.542(3) 0.225(19) Uani 0.25 1 d PDU A 2 H12D H 0.1215 0.93 0.5843 0.337 Uiso 0.25 1 calc PR A 2 H12E H 0.3207 0.984 0.5292 0.337 Uiso 0.25 1 calc PR A 2 H12F H 0.3255 0.8025 0.5763 0.337 Uiso 0.25 1 calc PR A 2 C7" C 0.2003(8) 0.3794(6) 0.2187(5) 0.0699(16) Uani 0.25 1 d PDU A 3 H7"1 H 0.0778 0.455 0.2052 0.084 Uiso 0.25 1 calc PR A 3 H7"2 H 0.3177 0.4236 0.186 0.084 Uiso 0.25 1 calc PR A 3 C8" C 0.214(5) 0.357(3) 0.3339(12) 0.081(7) Uani 0.25 1 d PDU A 3 H8"1 H 0.3307 0.2727 0.3453 0.097 Uiso 0.25 1 calc PR A 3 H8"2 H 0.093 0.3158 0.3651 0.097 Uiso 0.25 1 calc PR A 3 C9" C 0.236(5) 0.535(4) 0.390(2) 0.105(7) Uani 0.25 1 d PDU A 3 H9"1 H 0.121 0.618 0.3746 0.126 Uiso 0.25 1 calc PR A 3 H9"2 H 0.2229 0.5178 0.4647 0.126 Uiso 0.25 1 calc PR A 3 C10" C 0.390(5) 0.599(4) 0.369(4) 0.134(9) Uani 0.25 1 d PDU A 3 H10E H 0.3996 0.628 0.2954 0.161 Uiso 0.25 1 calc PR A 3 H10F H 0.5083 0.5164 0.38 0.161 Uiso 0.25 1 calc PR A 3 C11" C 0.394(6) 0.765(4) 0.436(4) 0.156(9) Uani 0.25 1 d PDU A 3 H11E H 0.3922 0.7338 0.5091 0.188 Uiso 0.25 1 calc PR A 3 H11F H 0.521 0.8069 0.4168 0.188 Uiso 0.25 1 calc PR A 3 C12" C 0.235(6) 0.892(4) 0.424(4) 0.186(15) Uani 0.25 1 d PDU A 3 H12G H 0.2866 0.9962 0.4104 0.279 Uiso 0.25 1 calc PR A 3 H12H H 0.1445 0.9039 0.4872 0.279 Uiso 0.25 1 calc PR A 3 H12I H 0.1629 0.8648 0.3676 0.279 Uiso 0.25 1 calc PR A 3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0343(3) 0.0552(3) 0.1146(5) -0.0202(3) -0.0096(3) -0.0027(2) N1 0.036(2) 0.046(2) 0.089(3) -0.008(2) -0.006(2) -0.0064(17) C2 0.032(2) 0.053(3) 0.100(5) -0.002(3) -0.003(3) -0.010(2) O2 0.0328(18) 0.063(2) 0.161(4) -0.017(2) -0.013(2) -0.0132(16) N3 0.0222(17) 0.042(2) 0.101(4) -0.005(2) 0.0010(19) -0.0018(15) C4 0.033(2) 0.047(3) 0.066(4) 0.006(3) -0.008(2) -0.006(2) N4 0.036(2) 0.047(2) 0.109(4) -0.007(2) -0.010(2) -0.0098(17) C5 0.027(2) 0.062(3) 0.082(4) -0.006(3) -0.004(2) -0.008(2) C6 0.031(2) 0.055(3) 0.074(4) -0.005(3) -0.001(2) 0.004(2) C7 0.056(3) 0.054(3) 0.099(5) -0.013(3) -0.004(3) -0.011(2) C8 0.107(10) 0.061(7) 0.104(9) -0.037(7) -0.001(8) -0.006(7) C9 0.165(12) 0.140(12) 0.126(12) -0.013(11) -0.027(11) -0.033(11) C10 0.178(12) 0.119(10) 0.128(12) -0.006(10) 0.009(11) -0.061(10) C11 0.179(15) 0.122(12) 0.125(14) -0.012(10) -0.017(12) -0.065(12) C12 0.210(19) 0.172(17) 0.108(14) -0.014(12) -0.019(14) -0.105(15) C7' 0.056(3) 0.054(3) 0.099(5) -0.013(3) -0.004(3) -0.011(2) C8' 0.089(9) 0.082(9) 0.098(9) -0.013(7) -0.008(7) -0.016(7) C9' 0.140(13) 0.097(13) 0.109(14) -0.001(12) 0.017(12) -0.060(12) C10' 0.171(14) 0.137(13) 0.139(15) -0.005(14) 0.000(13) -0.055(13) C11' 0.190(19) 0.153(19) 0.16(2) -0.011(18) -0.002(18) -0.079(18) C12' 0.28(4) 0.26(4) 0.16(4) 0.04(3) -0.02(4) -0.11(4) C7" 0.056(3) 0.054(3) 0.099(5) -0.013(3) -0.004(3) -0.011(2) C8" 0.075(13) 0.058(12) 0.107(13) -0.024(11) 0.001(11) -0.010(11) C9" 0.115(9) 0.096(9) 0.105(9) -0.011(7) -0.006(7) -0.023(7) C10" 0.161(15) 0.124(14) 0.120(15) -0.005(14) -0.002(14) -0.037(14) C11" 0.165(11) 0.152(11) 0.156(11) -0.001(8) -0.013(8) -0.037(8) C12" 0.23(3) 0.16(3) 0.20(3) 0.04(3) 0.01(3) -0.14(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.363(6) . ? N1 C2 1.371(6) . ? N1 C7 1.474(6) . ? C2 O2 1.204(5) . ? C2 N3 1.377(6) . ? N3 C4 1.354(5) . ? N3 H3 0.86 . ? C4 N4 1.288(6) . ? C4 C5 1.417(6) . ? N4 H4A 0.86 . ? N4 H4B 0.86 . ? C5 C6 1.332(6) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 C8 1.505(12) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C9 1.668(15) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 C10 1.227(17) . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 C11 1.591(17) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C12 1.38(2) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C12 H12C 0.96 . ? C8' C9' 1.656(18) . ? C8' H8'1 0.97 . ? C8' H8'2 0.97 . ? C9' C10' 1.23(2) . ? C9' H9'1 0.97 . ? C9' H9'2 0.97 . ? C10' C11' 1.58(2) . ? C10' H10C 0.97 . ? C10' H10D 0.97 . ? C11' C12' 1.37(3) . ? C11' H11C 0.97 . ? C11' H11D 0.97 . ? C12' H12D 0.96 . ? C12' H12E 0.96 . ? C12' H12F 0.96 . ? C8" C9" 1.641(17) . ? C8" H8"1 0.97 . ? C8" H8"2 0.97 . ? C9" C10" 1.23(2) . ? C9" H9"1 0.97 . ? C9" H9"2 0.97 . ? C10" C11" 1.60(2) . ? C10" H10E 0.97 . ? C10" H10F 0.97 . ? C11" C12" 1.38(3) . ? C11" H11E 0.97 . ? C11" H11F 0.97 . ? C12" H12G 0.96 . ? C12" H12H 0.96 . ? C12" H12I 0.96 . ? 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 C6 N1 C2 121.1(4) . . ? C6 N1 C7 121.0(4) . . ? C2 N1 C7 117.9(4) . . ? O2 C2 N1 123.9(5) . . ? O2 C2 N3 121.3(4) . . ? N1 C2 N3 114.8(4) . . ? C4 N3 C2 126.2(4) . . ? C4 N3 H3 116.9 . . ? C2 N3 H3 116.9 . . ? N4 C4 N3 119.9(4) . . ? N4 C4 C5 123.9(4) . . ? N3 C4 C5 116.2(4) . . ? C4 N4 H4A 120 . . ? C4 N4 H4B 120 . . ? H4A N4 H4B 120 . . ? C6 C5 C4 118.6(4) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 N1 123.1(4) . . ? C5 C6 H6 118.5 . . ? N1 C6 H6 118.5 . . ? N1 C7 C8 116.8(7) . . ? N1 C7 H7A 108.1 . . ? C8 C7 H7A 108.1 . . ? N1 C7 H7B 108.1 . . ? C8 C7 H7B 108.1 . . ? H7A C7 H7B 107.3 . . ? C7 C8 C9 104.7(10) . . ? C7 C8 H8A 110.8 . . ? C9 C8 H8A 110.8 . . ? C7 C8 H8B 110.8 . . ? C9 C8 H8B 110.8 . . ? H8A C8 H8B 108.9 . . ? C10 C9 C8 114.4(15) . . ? C10 C9 H9A 108.7 . . ? C8 C9 H9A 108.7 . . ? C10 C9 H9B 108.7 . . ? C8 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C9 C10 C11 112.5(16) . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 113.0(16) . . ? C12 C11 H11A 109 . . ? C10 C11 H11A 109 . . ? C12 C11 H11B 109 . . ? C10 C11 H11B 109 . . ? H11A C11 H11B 107.8 . . ? C9' C8' H8'1 109.8 . . ? C9' C8' H8'2 109.8 . . ? H8'1 C8' H8'2 108.3 . . ? C10' C9' C8' 113(2) . . ? C10' C9' H9'1 109 . . ? C8' C9' H9'1 109 . . ? C10' C9' H9'2 109 . . ? C8' C9' H9'2 109 . . ? H9'1 C9' H9'2 107.8 . . ? C9' C10' C11' 116(3) . . ? C9' C10' H10C 108.2 . . ? C11' C10' H10C 108.2 . . ? C9' C10' H10D 108.2 . . ? C11' C10' H10D 108.2 . . ? H10C C10' H10D 107.4 . . ? C12' C11' C10' 114(3) . . ? C12' C11' H11C 108.8 . . ? C10' C11' H11C 108.7 . . ? C12' C11' H11D 108.8 . . ? C10' C11' H11D 108.8 . . ? H11C C11' H11D 107.7 . . ? C11' C12' H12D 109.5 . . ? C11' C12' H12E 109.5 . . ? H12D C12' H12E 109.5 . . ? C11' C12' H12F 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? C9" C8" H8"1 109.4 . . ? C9" C8" H8"2 109.4 . . ? H8"1 C8" H8"2 108 . . ? C10" C9" C8" 119(2) . . ? C10" C9" H9"1 107.5 . . ? C8" C9" H9"1 107.5 . . ? C10" C9" H9"2 107.5 . . ? C8" C9" H9"2 107.5 . . ? H9"1 C9" H9"2 107 . . ? C9" C10" C11" 113(2) . . ? C9" C10" H10E 109 . . ? C11" C10" H10E 109 . . ? C9" C10" H10F 109 . . ? C11" C10" H10F 109 . . ? H10E C10" H10F 107.8 . . ? C12" C11" C10" 114(3) . . ? C12" C11" H11E 108.8 . . ? C10" C11" H11E 108.8 . . ? C12" C11" H11F 108.8 . . ? C10" C11" H11F 108.8 . . ? H11E C11" H11F 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 O2 -179.3(6) . . . . ? C7 N1 C2 O2 2.5(9) . . . . ? C6 N1 C2 N3 0.3(8) . . . . ? C7 N1 C2 N3 -177.9(5) . . . . ? O2 C2 N3 C4 179.5(5) . . . . ? N1 C2 N3 C4 -0.1(8) . . . . ? C2 N3 C4 N4 178.7(5) . . . . ? C2 N3 C4 C5 -0.6(8) . . . . ? N4 C4 C5 C6 -178.1(5) . . . . ? N3 C4 C5 C6 1.1(8) . . . . ? C4 C5 C6 N1 -1.0(8) . . . . ? C2 N1 C6 C5 0.3(8) . . . . ? C7 N1 C6 C5 178.4(5) . . . . ? C6 N1 C7 C8 79.9(10) . . . . ? C2 N1 C7 C8 -101.9(9) . . . . ? N1 C7 C8 C9 176.7(9) . . . . ? C7 C8 C9 C10 -79(2) . . . . ? C8 C9 C10 C11 -165.4(16) . . . . ? C9 C10 C11 C12 -173(2) . . . . ? C8' C9' C10' C11' 154(3) . . . . ? C9' C10' C11' C12' 144(5) . . . . ? C8" C9" C10" C11" -176(3) . . . . ? C9" C10" C11" C12" -60(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3 Br1 0.86 2.41 3.239(4) 161.1 2_655 N4 H4A Br1 0.86 2.8 3.530(4) 144.2 2_655 N4 H4A Br1 0.86 2.99 3.433(4) 114 1_545 N4 H4B Br1 0.86 2.54 3.385(4) 165.7 2 # END of CIF data_mb280710 _database_code_depnum_ccdc_archive 'CCDC 864485' #TrackingRef '9249_web_deposit_cif_file_2_MiquelBarcelo-Oliver_1327507456.compound 4.cif' _audit_creation_date 2010-07-29T17:03:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C10 H18 N3 O), 2(C10 H17 N3 O), Cl6 Hg2' _chemical_formula_sum 'C40 H70 Cl6 Hg2 N12 O4' _chemical_formula_weight 1396.96 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.4416(2) _cell_length_b 28.1838(11) _cell_length_c 25.9487(6) _cell_angle_alpha 90 _cell_angle_beta 91.616(3) _cell_angle_gamma 90 _cell_volume 5440.1(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 12249 _cell_measurement_theta_min 2.6718 _cell_measurement_theta_max 29.3042 _cell_measurement_temperature 183(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2752 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.981 _exptl_absorpt_correction_T_min 0.45739 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur Ruby' _diffrn_measurement_method '/o oscillation scan' _diffrn_detector_area_resol_mean 10.4498 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_unetI/netI 0.0637 _diffrn_reflns_number 32624 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 11114 _reflns_number_gt 6669 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlis RED (Oxford, 2007)' _computing_cell_refinement 'CrysAlis RED (Oxford, 2007)' _computing_data_reduction 'CrysAlis RED (Oxford, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1003P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 11114 _refine_ls_number_parameters 671 _refine_ls_number_restraints 289 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.052 _refine_ls_wR_factor_ref 0.1652 _refine_ls_wR_factor_gt 0.1555 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.967 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 2.399 _refine_diff_density_min -1.164 _refine_diff_density_rms 0.162 #----------------------------------------------------------------------------# # 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' 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' Hg Hg -2.3894 9.2266 '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg1 Hg 0.57741(3) 0.194019(9) 0.378403(9) 0.05420(8) Uani 1 1 d . . . Hg2 Hg 0.79410(3) 0.310706(9) 0.340325(9) 0.05491(8) Uani 1 1 d . . . Cl1 Cl 0.35754(16) 0.14748(4) 0.32776(4) 0.0335(3) Uani 1 1 d . . . Cl2 Cl 0.66020(17) 0.16006(5) 0.46206(5) 0.0403(3) Uani 1 1 d . . . Cl3 Cl 0.69816(19) 0.35471(5) 0.26303(5) 0.0493(4) Uani 1 1 d . . . Cl4 Cl 1.02942(18) 0.34874(5) 0.39196(5) 0.0430(4) Uani 1 1 d . . . Cl5 Cl 0.86567(12) 0.21850(4) 0.32759(3) 0.0173(2) Uani 1 1 d . . . Cl6 Cl 0.50593(15) 0.28640(4) 0.38798(4) 0.0305(3) Uani 1 1 d . . . N1 N 0.1416(6) 0.34048(16) 0.22316(17) 0.0462(13) Uani 1 1 d D . . C2 C 0.0658(5) 0.3151(2) 0.18226(19) 0.0440(16) Uani 1 1 d D . . O2 O -0.0086(5) 0.33459(14) 0.14594(16) 0.0618(13) Uani 1 1 d D . . N3 N 0.0774(5) 0.26603(15) 0.18523(16) 0.0370(12) Uani 1 1 d D . . C4 C 0.1566(7) 0.2414(2) 0.22505(19) 0.0395(15) Uani 1 1 d D . . N4 N 0.1587(6) 0.19551(15) 0.22308(17) 0.0438(13) Uani 1 1 d D . . H4A H 0.1095 0.1807 0.1964 0.053 Uiso 1 1 calc R . . H4B H 0.2093 0.1791 0.2485 0.053 Uiso 1 1 calc R . . C5 C 0.2372(7) 0.2681(2) 0.2660(2) 0.0468(16) Uani 1 1 d D . . H5 H 0.2982 0.2528 0.2941 0.056 Uiso 1 1 calc R . . C6 C 0.2240(7) 0.3178(2) 0.2638(2) 0.0522(18) Uani 1 1 d D . . H6 H 0.2738 0.3361 0.2914 0.063 Uiso 1 1 calc R . . C7 C 0.1353(8) 0.3913(2) 0.2214(3) 0.0589(19) Uani 1 1 d . B . H7A H 0.1394 0.4038 0.257 0.071 Uiso 1 1 calc R . . H7B H 0.0196 0.4013 0.205 0.071 Uiso 1 1 calc R . . C8 C 0.2855(10) 0.4128(2) 0.1924(3) 0.078(2) Uani 1 1 d DU . . H8A H 0.2687 0.4045 0.1555 0.094 Uiso 1 1 calc R A 5 H8B H 0.3997 0.3982 0.2048 0.094 Uiso 1 1 calc R A 5 C9 C 0.3035(15) 0.4661(3) 0.1968(3) 0.151(4) Uani 0.5 1 d PDU B 5 H9A H 0.2705 0.4761 0.2319 0.182 Uiso 0.5 1 calc PR B 5 H9B H 0.4306 0.4751 0.192 0.182 Uiso 0.5 1 calc PR B 5 C10 C 0.188(2) 0.4918(4) 0.1584(8) 0.184(8) Uani 0.5 1 d PDU B 5 H10A H 0.0627 0.4875 0.1692 0.221 Uiso 0.5 1 calc PR B 5 H10B H 0.1987 0.4745 0.1254 0.221 Uiso 0.5 1 calc PR B 5 C11 C 0.209(3) 0.5438(4) 0.1458(6) 0.141(7) Uani 0.5 1 d PDU B 5 H11A H 0.3378 0.55 0.1407 0.169 Uiso 0.5 1 calc PR B 5 H11B H 0.1453 0.5497 0.1123 0.169 Uiso 0.5 1 calc PR B 5 C12 C 0.145(3) 0.5788(5) 0.1822(7) 0.127(8) Uani 0.5 1 d PDU B 5 H12A H 0.0518 0.5646 0.2032 0.191 Uiso 0.5 1 calc PR B 5 H12B H 0.095 0.6061 0.1633 0.191 Uiso 0.5 1 calc PR B 5 H12C H 0.2456 0.5893 0.2046 0.191 Uiso 0.5 1 calc PR B 5 C9' C 0.3035(15) 0.4661(3) 0.1968(3) 0.151(4) Uani 0.5 1 d PDU B 6 H9'1 H 0.2727 0.4747 0.2325 0.182 Uiso 0.5 1 calc PR B 6 H9'2 H 0.4325 0.4737 0.1932 0.182 Uiso 0.5 1 calc PR B 6 C10' C 0.205(3) 0.4977(3) 0.1632(6) 0.136(8) Uani 0.5 1 d PDU B 6 H10C H 0.0746 0.4912 0.1656 0.163 Uiso 0.5 1 calc PR B 6 H10D H 0.2392 0.492 0.1272 0.163 Uiso 0.5 1 calc PR B 6 C11' C 0.2410(19) 0.5494(3) 0.1771(5) 0.086(5) Uani 0.5 1 d PDU B 6 H11C H 0.2252 0.5549 0.2143 0.103 Uiso 0.5 1 calc PR B 6 H11D H 0.3646 0.5587 0.1681 0.103 Uiso 0.5 1 calc PR B 6 C12' C 0.108(2) 0.5758(5) 0.1463(6) 0.087(5) Uani 0.5 1 d PDU B 6 H12D H 0.1404 0.6095 0.1462 0.13 Uiso 0.5 1 calc PR B 6 H12E H -0.0107 0.572 0.1611 0.13 Uiso 0.5 1 calc PR B 6 H12F H 0.105 0.5637 0.1108 0.13 Uiso 0.5 1 calc PR B 6 H3 H 0.024(7) 0.239(3) 0.149(3) 0.13 Uiso 1 1 d D . . N21 N 0.5613(5) 0.15822(15) 0.15914(15) 0.0365(11) Uani 1 1 d . . . C22 C 0.4759(7) 0.18172(19) 0.11752(19) 0.0360(14) Uani 1 1 d . . . O22 O 0.4118(5) 0.15828(13) 0.08193(13) 0.0435(10) Uani 1 1 d . . . N23 N 0.4653(5) 0.22982(15) 0.11817(15) 0.0360(11) Uani 1 1 d . . . C24 C 0.5401(7) 0.25546(19) 0.15838(18) 0.0369(14) Uani 1 1 d . . . N24 N 0.5257(6) 0.30149(15) 0.15732(17) 0.0426(13) Uani 1 1 d . . . H24A H 0.469 0.3155 0.1313 0.051 Uiso 1 1 calc R . . H24B H 0.5726 0.3186 0.1827 0.051 Uiso 1 1 calc R . . C25 C 0.6269(7) 0.2319(2) 0.2007(2) 0.0441(15) Uani 1 1 d . . . H25 H 0.6785 0.2491 0.2289 0.053 Uiso 1 1 calc R . . C26 C 0.6331(7) 0.1835(2) 0.1992(2) 0.0485(17) Uani 1 1 d . . . H26 H 0.6897 0.167 0.2271 0.058 Uiso 1 1 calc R . . C27 C 0.5648(7) 0.1067(2) 0.1610(2) 0.0490(17) Uani 1 1 d . D . H27A H 0.6782 0.0961 0.1782 0.059 Uiso 1 1 calc R . . H27B H 0.5616 0.094 0.1254 0.059 Uiso 1 1 calc R . . C28 C 0.4068(9) 0.0871(2) 0.1898(2) 0.0580(18) Uani 1 1 d DU . . H28A H 0.2935 0.0976 0.1725 0.07 Uiso 1 1 calc R C 1 H28B H 0.4095 0.1001 0.2253 0.07 Uiso 1 1 calc R C 1 C29 C 0.4094(9) 0.0328(2) 0.1925(3) 0.078(2) Uani 0.7 1 d PDU D 1 H29A H 0.3957 0.0199 0.1571 0.094 Uiso 0.7 1 calc PR D 1 H29B H 0.5279 0.0224 0.2067 0.094 Uiso 0.7 1 calc PR D 1 C30 C 0.2638(12) 0.0121(4) 0.2252(4) 0.096(3) Uani 0.7 1 d PDU D 1 H30A H 0.2898 -0.0219 0.2316 0.115 Uiso 0.7 1 calc PR D 1 H30B H 0.2653 0.0285 0.259 0.115 Uiso 0.7 1 calc PR D 1 C31 C 0.0793(13) 0.0167(4) 0.2004(5) 0.107(4) Uani 0.7 1 d PDU D 1 H31A H 0.068 0.0483 0.1839 0.129 Uiso 0.7 1 calc PR D 1 H31B H -0.0119 0.0147 0.2273 0.129 Uiso 0.7 1 calc PR D 1 C32 C 0.0417(19) -0.0212(5) 0.1605(5) 0.144(6) Uani 0.7 1 d PDU D 1 H32A H 0.073 -0.0093 0.1264 0.216 Uiso 0.7 1 calc PR D 1 H32B H -0.0862 -0.0295 0.1603 0.216 Uiso 0.7 1 calc PR D 1 H32C H 0.1138 -0.0494 0.1688 0.216 Uiso 0.7 1 calc PR D 1 C29' C 0.4094(9) 0.0328(2) 0.1925(3) 0.078(2) Uani 0.3 1 d PDU D 2 H29C H 0.3871 0.0193 0.1577 0.094 Uiso 0.3 1 calc PR D 2 H29D H 0.5289 0.0218 0.2053 0.094 Uiso 0.3 1 calc PR D 2 C30' C 0.267(2) 0.0160(6) 0.2282(7) 0.137(6) Uani 0.3 1 d PDU D 2 H30C H 0.3248 0.0071 0.2616 0.164 Uiso 0.3 1 calc PR D 2 H30D H 0.184 0.0427 0.2347 0.164 Uiso 0.3 1 calc PR D 2 C31' C 0.159(2) -0.0251(7) 0.2088(10) 0.209(9) Uani 0.3 1 d PDU D 2 H31C H 0.1066 -0.0414 0.2387 0.251 Uiso 0.3 1 calc PR D 2 H31D H 0.2404 -0.0478 0.1922 0.251 Uiso 0.3 1 calc PR D 2 C32' C 0.009(3) -0.0132(12) 0.1712(11) 0.180(11) Uani 0.3 1 d PDU D 2 H32D H -0.0811 0.006 0.1884 0.271 Uiso 0.3 1 calc PR D 2 H32E H -0.0468 -0.0426 0.1583 0.271 Uiso 0.3 1 calc PR D 2 H32F H 0.0572 0.0046 0.1423 0.271 Uiso 0.3 1 calc PR D 2 N41 N -0.1151(6) 0.13916(17) 0.06160(16) 0.0464(13) Uani 1 1 d . . . C42 C -0.0557(7) 0.1661(2) 0.10219(19) 0.0393(14) Uani 1 1 d . . . O42 O 0.0102(5) 0.14528(13) 0.14185(14) 0.0488(11) Uani 1 1 d . . . N43 N -0.0671(6) 0.21391(16) 0.10076(15) 0.0373(12) Uani 1 1 d . . . C44 C -0.1442(7) 0.2345(2) 0.05962(19) 0.0408(15) Uani 1 1 d . . . N44 N -0.1548(6) 0.28185(18) 0.05868(17) 0.0482(14) Uani 1 1 d . . . H44A H -0.1114 0.2986 0.0848 0.058 Uiso 1 1 calc R . . H44B H -0.2051 0.2963 0.0319 0.058 Uiso 1 1 calc R . . C45 C -0.2098(8) 0.2080(2) 0.0169(2) 0.0538(18) Uani 1 1 d . . . H45 H -0.2628 0.2228 -0.0126 0.065 Uiso 1 1 calc R . . C46 C -0.1930(8) 0.1604(2) 0.0204(2) 0.0560(18) Uani 1 1 d . . . H46 H -0.2379 0.1413 -0.0072 0.067 Uiso 1 1 calc R . . C47 C -0.1025(10) 0.0872(2) 0.0630(3) 0.067(2) Uani 1 1 d . . . H47A H -0.187 0.0736 0.0368 0.081 Uiso 1 1 calc R . . H47B H -0.1383 0.0757 0.0973 0.081 Uiso 1 1 calc R . . C48 C 0.1057(13) 0.0685(3) 0.0516(3) 0.110(3) Uani 1 1 d U . . H48A H 0.191 0.0867 0.0739 0.132 Uiso 1 1 calc R . . H48B H 0.1153 0.0348 0.0618 0.132 Uiso 1 1 calc R . . C49 C 0.1577(12) 0.0726(3) 0.0018(4) 0.104(3) Uani 1 1 d U . . H49A H 0.1304 0.1056 -0.0091 0.125 Uiso 1 1 calc R . . H49B H 0.0776 0.0518 -0.0192 0.125 Uiso 1 1 calc R . . C50 C 0.3561(15) 0.0619(3) -0.0149(5) 0.176(3) Uani 1 1 d U . . H50A H 0.386 0.029 -0.0046 0.211 Uiso 1 1 calc R . . H50B H 0.4383 0.0832 0.0048 0.211 Uiso 1 1 calc R . . C51 C 0.3972(16) 0.0677(6) -0.0752(6) 0.244(6) Uani 1 1 d U . . H51A H 0.3322 0.0424 -0.0946 0.293 Uiso 1 1 calc R . . H51B H 0.3474 0.0985 -0.0872 0.293 Uiso 1 1 calc R . . C52 C 0.5539(14) 0.0661(4) -0.0861(6) 0.192(5) Uani 1 1 d U . . H52A H 0.6152 0.0419 -0.065 0.287 Uiso 1 1 calc R . . H52B H 0.6098 0.0971 -0.0795 0.287 Uiso 1 1 calc R . . H52C H 0.5636 0.058 -0.1227 0.287 Uiso 1 1 calc R . . N61 N 0.1766(6) 0.34254(16) -0.00520(16) 0.0415(12) Uani 1 1 d D . . C62 C 0.2708(5) 0.32186(19) 0.03517(19) 0.0413(15) Uani 1 1 d D . . O62 O 0.3292(5) 0.34443(14) 0.07208(15) 0.0574(12) Uani 1 1 d D . . N63 N 0.2976(6) 0.27358(15) 0.03296(16) 0.0405(12) Uani 1 1 d D . . C64 C 0.2351(7) 0.24628(19) -0.00830(19) 0.0373(14) Uani 1 1 d D . . N64 N 0.2601(6) 0.20068(15) -0.00528(16) 0.0419(13) Uani 1 1 d D . . H64A H 0.3147 0.1884 0.0221 0.05 Uiso 1 1 calc R . . H64B H 0.2224 0.1821 -0.0306 0.05 Uiso 1 1 calc R . . C65 C 0.1475(7) 0.2692(2) -0.0502(2) 0.0406(15) Uani 1 1 d D . . H65 H 0.108 0.252 -0.08 0.049 Uiso 1 1 calc R . . C66 C 0.1217(7) 0.3168(2) -0.0464(2) 0.0462(16) Uani 1 1 d D . . H66 H 0.062 0.3327 -0.0743 0.055 Uiso 1 1 calc R . . C67 C 0.1384(8) 0.3933(2) -0.0038(2) 0.0531(17) Uani 1 1 d . F . H67A H 0.1494 0.4046 0.0323 0.064 Uiso 1 1 calc R . . H67B H 0.0132 0.3989 -0.0162 0.064 Uiso 1 1 calc R . . C68 C 0.2653(10) 0.4214(2) -0.0368(3) 0.071(2) Uani 1 1 d DU . . H68A H 0.259 0.4092 -0.0726 0.086 Uiso 1 1 calc R E 3 H68B H 0.3902 0.4174 -0.0233 0.086 Uiso 1 1 calc R E 3 C69 C 0.2151(11) 0.4747(2) -0.0366(3) 0.094(3) Uani 0.5 1 d PDU F 3 H69A H 0.0824 0.4773 -0.0377 0.113 Uiso 0.5 1 calc PR F 3 H69B H 0.2588 0.4886 -0.0035 0.113 Uiso 0.5 1 calc PR F 3 C70 C 0.288(2) 0.5045(3) -0.0804(6) 0.106(5) Uani 0.5 1 d PDU F 3 H70A H 0.421 0.5039 -0.079 0.127 Uiso 0.5 1 calc PR F 3 H70B H 0.2463 0.4912 -0.114 0.127 Uiso 0.5 1 calc PR F 3 C71 C 0.2212(15) 0.5552(3) -0.0750(5) 0.067(4) Uani 0.5 1 d PDU F 3 H71A H 0.0909 0.557 -0.0836 0.08 Uiso 0.5 1 calc PR F 3 H71B H 0.2416 0.5665 -0.0392 0.08 Uiso 0.5 1 calc PR F 3 C72 C 0.3242(18) 0.5850(4) -0.1115(6) 0.090(5) Uani 0.5 1 d PDU F 3 H72A H 0.2854 0.5776 -0.147 0.135 Uiso 0.5 1 calc PR F 3 H72B H 0.4529 0.5783 -0.1069 0.135 Uiso 0.5 1 calc PR F 3 H72C H 0.3019 0.6186 -0.1044 0.135 Uiso 0.5 1 calc PR F 3 C69' C 0.2151(11) 0.4747(2) -0.0366(3) 0.094(3) Uani 0.5 1 d PDU F 4 H69C H 0.2058 0.4866 -0.0009 0.113 Uiso 0.5 1 calc PR F 4 H69D H 0.0989 0.48 -0.0552 0.113 Uiso 0.5 1 calc PR F 4 C70' C 0.3709(19) 0.5001(3) -0.0646(5) 0.092(4) Uani 0.5 1 d PDU F 4 H70C H 0.4847 0.4885 -0.0485 0.11 Uiso 0.5 1 calc PR F 4 H70D H 0.3676 0.4885 -0.1006 0.11 Uiso 0.5 1 calc PR F 4 C71' C 0.385(2) 0.5529(4) -0.0670(7) 0.143(7) Uani 0.5 1 d PDU F 4 H71C H 0.507 0.5624 -0.0772 0.171 Uiso 0.5 1 calc PR F 4 H71D H 0.3616 0.5669 -0.0329 0.171 Uiso 0.5 1 calc PR F 4 C72' C 0.248(2) 0.5702(7) -0.1062(7) 0.138(7) Uani 0.5 1 d PDU F 4 H72D H 0.254 0.551 -0.1375 0.207 Uiso 0.5 1 calc PR F 4 H72E H 0.2723 0.6035 -0.1145 0.207 Uiso 0.5 1 calc PR F 4 H72F H 0.1274 0.5676 -0.092 0.207 Uiso 0.5 1 calc PR F 4 H63 H 0.386(8) 0.248(4) 0.066(3) 0.207 Uiso 1 1 d 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 Hg1 0.05309(15) 0.07204(17) 0.03684(12) 0.00382(11) -0.00994(11) -0.01145(12) Hg2 0.05299(15) 0.07210(17) 0.03902(13) 0.00300(11) -0.00975(11) -0.01178(12) Cl1 0.0364(6) 0.0438(7) 0.0194(5) 0.0002(5) -0.0165(5) -0.0043(5) Cl2 0.0410(7) 0.0541(8) 0.0254(6) 0.0037(6) -0.0083(5) -0.0136(6) Cl3 0.0567(8) 0.0632(9) 0.0273(6) 0.0045(6) -0.0148(6) -0.0184(7) Cl4 0.0451(7) 0.0475(8) 0.0354(7) 0.0002(6) -0.0178(6) -0.0020(6) Cl5 0.0123(5) 0.0292(5) 0.0106(4) -0.0018(4) 0.0043(4) 0.0001(4) Cl6 0.0238(6) 0.0427(7) 0.0252(6) -0.0010(5) 0.0061(5) 0.0022(5) N1 0.040(3) 0.052(3) 0.047(3) -0.008(2) -0.001(2) -0.004(2) C2 0.030(3) 0.064(4) 0.038(3) -0.001(3) -0.003(2) 0.003(3) O2 0.076(3) 0.049(2) 0.059(3) 0.000(2) -0.027(2) 0.004(2) N3 0.027(2) 0.047(3) 0.036(2) -0.001(2) -0.0036(19) -0.0020(19) C4 0.028(3) 0.058(3) 0.033(3) -0.001(3) 0.005(2) -0.004(2) N4 0.054(3) 0.047(3) 0.030(2) 0.002(2) -0.009(2) -0.003(2) C5 0.035(3) 0.070(4) 0.035(3) 0.004(3) -0.001(2) -0.004(3) C6 0.038(3) 0.087(5) 0.031(3) -0.014(3) 0.006(3) -0.014(3) C7 0.052(4) 0.055(4) 0.069(4) -0.025(3) -0.014(3) 0.003(3) C8 0.113(6) 0.054(3) 0.067(5) -0.008(3) 0.008(4) -0.020(4) C9 0.284(12) 0.057(3) 0.114(7) -0.016(4) 0.027(7) -0.001(6) C10 0.138(16) 0.065(5) 0.35(2) -0.013(8) -0.025(13) 0.045(9) C11 0.182(19) 0.068(6) 0.168(14) -0.036(6) -0.069(12) 0.006(9) C12 0.180(19) 0.056(7) 0.145(15) 0.021(8) 0.003(14) 0.016(11) C9' 0.284(12) 0.057(3) 0.114(7) -0.016(4) 0.027(7) -0.001(6) C10' 0.24(2) 0.036(5) 0.132(14) -0.035(6) -0.018(13) -0.015(8) C11' 0.125(11) 0.047(5) 0.082(10) -0.028(6) -0.041(8) -0.015(7) C12' 0.119(12) 0.063(7) 0.078(10) 0.017(8) -0.003(9) -0.004(7) N21 0.035(2) 0.049(3) 0.025(2) 0.002(2) -0.0028(19) -0.001(2) C22 0.026(3) 0.051(3) 0.031(3) -0.004(2) 0.005(2) -0.004(2) O22 0.053(2) 0.049(2) 0.0280(18) -0.0043(17) -0.0069(17) -0.0063(18) N23 0.030(2) 0.047(3) 0.031(2) 0.000(2) 0.0017(19) -0.0093(19) C24 0.027(3) 0.057(3) 0.027(3) -0.005(3) 0.006(2) -0.007(2) N24 0.055(3) 0.044(3) 0.028(2) -0.003(2) -0.010(2) -0.009(2) C25 0.036(3) 0.065(4) 0.031(3) -0.003(3) -0.006(2) -0.011(3) C26 0.025(3) 0.081(4) 0.038(3) 0.006(3) -0.009(2) 0.002(3) C27 0.043(3) 0.065(4) 0.038(3) 0.003(3) -0.001(3) 0.005(3) C28 0.071(4) 0.054(3) 0.049(4) 0.002(3) -0.002(3) 0.003(3) C29 0.101(4) 0.053(3) 0.081(5) 0.010(4) 0.004(4) -0.004(3) C30 0.124(6) 0.093(6) 0.072(7) -0.019(5) 0.019(5) -0.051(6) C31 0.106(5) 0.069(7) 0.149(10) -0.007(6) 0.033(7) -0.015(6) C32 0.115(10) 0.172(12) 0.145(11) -0.050(8) 0.000(8) -0.048(10) C29' 0.101(4) 0.053(3) 0.081(5) 0.010(4) 0.004(4) -0.004(3) C30' 0.089(10) 0.142(10) 0.180(17) 0.112(8) 0.020(7) 0.009(9) C31' 0.151(11) 0.203(15) 0.27(2) 0.111(15) 0.021(11) -0.066(10) C32' 0.263(18) 0.14(2) 0.14(2) 0.091(16) -0.001(13) -0.100(17) N41 0.050(3) 0.058(3) 0.031(2) -0.005(2) -0.001(2) -0.007(2) C42 0.034(3) 0.055(3) 0.029(3) -0.001(3) 0.004(2) -0.001(3) O42 0.055(2) 0.051(2) 0.040(2) -0.0016(19) 0.0016(19) -0.0039(19) N43 0.035(2) 0.052(3) 0.024(2) 0.004(2) -0.0054(18) -0.002(2) C44 0.029(3) 0.064(4) 0.030(3) -0.001(3) 0.007(2) -0.007(3) N44 0.040(3) 0.070(3) 0.035(3) 0.008(2) -0.006(2) -0.001(2) C45 0.045(3) 0.091(5) 0.025(3) -0.003(3) -0.007(3) -0.016(3) C46 0.048(3) 0.076(4) 0.044(3) -0.017(3) 0.000(3) -0.020(3) C47 0.090(5) 0.062(4) 0.051(4) -0.012(3) 0.012(4) -0.018(4) C48 0.153(7) 0.060(5) 0.116(5) -0.005(5) -0.004(5) -0.013(5) C49 0.125(5) 0.064(5) 0.125(5) 0.036(5) -0.001(5) -0.006(5) C50 0.202(6) 0.094(6) 0.234(6) -0.059(7) 0.047(6) 0.076(6) C51 0.137(6) 0.297(17) 0.304(8) 0.054(14) 0.117(7) 0.099(10) C52 0.103(6) 0.195(11) 0.277(11) -0.119(10) 0.021(7) -0.012(8) N61 0.039(2) 0.049(3) 0.036(2) 0.001(2) 0.008(2) -0.001(2) C62 0.041(3) 0.047(3) 0.036(3) -0.009(3) -0.001(3) -0.005(3) O62 0.077(3) 0.047(2) 0.047(2) -0.002(2) -0.008(2) -0.002(2) N63 0.048(3) 0.041(2) 0.033(2) -0.002(2) -0.008(2) -0.011(2) C64 0.034(3) 0.050(3) 0.029(3) 0.003(2) 0.010(2) -0.009(2) N64 0.051(3) 0.050(3) 0.024(2) -0.001(2) -0.007(2) -0.003(2) C65 0.034(3) 0.054(3) 0.033(3) 0.002(3) -0.006(2) 0.004(3) C66 0.034(3) 0.058(4) 0.046(3) 0.001(3) -0.002(3) 0.000(3) C67 0.056(4) 0.055(4) 0.049(4) -0.003(3) 0.000(3) 0.006(3) C68 0.082(5) 0.040(3) 0.093(5) 0.000(3) 0.027(4) 0.004(3) C69 0.128(6) 0.053(3) 0.104(6) 0.008(4) 0.018(5) 0.018(4) C70 0.105(12) 0.059(5) 0.156(12) 0.042(6) 0.018(10) 0.018(7) C71 0.044(7) 0.060(5) 0.098(10) 0.008(6) 0.005(7) 0.007(5) C72 0.078(10) 0.048(6) 0.145(14) 0.016(7) 0.038(9) 0.007(7) C69' 0.128(6) 0.053(3) 0.104(6) 0.008(4) 0.018(5) 0.018(4) C70' 0.194(12) 0.036(5) 0.048(8) 0.009(5) 0.031(8) 0.005(6) C71' 0.199(14) 0.051(6) 0.176(16) 0.036(10) -0.026(10) -0.007(8) C72' 0.170(16) 0.127(12) 0.118(14) 0.070(10) 0.054(10) 0.062(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Hg1 Cl2 2.4358(12) . ? Hg1 Cl1 2.4501(11) . ? Hg1 Cl5 2.6411(10) . ? Hg1 Cl6 2.6704(12) . ? Hg2 Cl4 2.4246(13) . ? Hg2 Cl3 2.4475(13) . ? Hg2 Cl6 2.5975(11) . ? Hg2 Cl5 2.6752(10) . ? N1 C6 1.364(7) . ? N1 C2 1.386(7) . ? N1 C7 1.435(7) . ? C2 O2 1.211(6) . ? C2 N3 1.389(7) . ? N3 C4 1.365(7) . ? N3 H3 1.27(7) . ? C4 N4 1.293(7) . ? C4 C5 1.422(8) . ? N4 H4A 0.88 . ? N4 H4B 0.88 . ? C5 C6 1.404(8) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C8 1.492(9) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 C9 1.514(10) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.486(14) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.511(13) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.453(15) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C10' C11' 1.522(12) . ? C10' H10C 0.99 . ? C10' H10D 0.99 . ? C11' C12' 1.459(14) . ? C11' H11C 0.99 . ? C11' H11D 0.99 . ? C12' H12D 0.98 . ? C12' H12E 0.98 . ? C12' H12F 0.98 . ? N21 C26 1.358(7) . ? N21 C22 1.403(6) . ? N21 C27 1.453(7) . ? C22 O22 1.222(6) . ? C22 N23 1.358(7) . ? N23 C24 1.374(6) . ? C24 N24 1.302(7) . ? C24 C25 1.423(7) . ? N24 H24A 0.88 . ? N24 H24B 0.88 . ? C25 C26 1.363(8) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? C27 C28 1.516(8) . ? C27 H27A 0.99 . ? C27 H27B 0.99 . ? C28 C29 1.533(8) . ? C28 H28A 0.99 . ? C28 H28B 0.99 . ? C29 C30 1.511(10) . ? C29 H29A 0.99 . ? C29 H29B 0.99 . ? C30 C31 1.505(12) . ? C30 H30A 0.99 . ? C30 H30B 0.99 . ? C31 C32 1.508(13) . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? C32 H32A 0.98 . ? C32 H32B 0.98 . ? C32 H32C 0.98 . ? C30' C31' 1.488(17) . ? C30' H30C 0.99 . ? C30' H30D 0.99 . ? C31' C32' 1.497(18) . ? C31' H31C 0.99 . ? C31' H31D 0.99 . ? C32' H32D 0.98 . ? C32' H32E 0.98 . ? C32' H32F 0.98 . ? N41 C46 1.343(7) . ? N41 C42 1.363(7) . ? N41 C47 1.467(8) . ? C42 O42 1.271(6) . ? C42 N43 1.350(7) . ? N43 C44 1.331(7) . ? C44 N44 1.336(7) . ? C44 C45 1.412(8) . ? N44 H44A 0.88 . ? N44 H44B 0.88 . ? C45 C46 1.349(9) . ? C45 H45 0.95 . ? C46 H46 0.95 . ? C47 C48 1.671(11) . ? C47 H47A 0.99 . ? C47 H47B 0.99 . ? C48 C49 1.365(12) . ? C48 H48A 0.99 . ? C48 H48B 0.99 . ? C49 C50 1.579(13) . ? C49 H49A 0.99 . ? C49 H49B 0.99 . ? C50 C51 1.611(19) . ? C50 H50A 0.99 . ? C50 H50B 0.99 . ? C51 C52 1.208(14) . ? C51 H51A 0.99 . ? C51 H51B 0.99 . ? C52 H52A 0.98 . ? C52 H52B 0.98 . ? C52 H52C 0.98 . ? N61 C66 1.346(7) . ? N61 C62 1.374(7) . ? N61 C67 1.459(7) . ? C62 O62 1.220(6) . ? C62 N63 1.377(7) . ? N63 C64 1.388(6) . ? N63 H63 1.28(9) . ? C64 N64 1.300(7) . ? C64 C65 1.409(7) . ? N64 H64A 0.88 . ? N64 H64B 0.88 . ? C65 C66 1.360(8) . ? C65 H65 0.95 . ? C66 H66 0.95 . ? C67 C68 1.517(9) . ? C67 H67A 0.99 . ? C67 H67B 0.99 . ? C68 C69 1.547(9) . ? C68 H68A 0.99 . ? C68 H68B 0.99 . ? C69 C70 1.524(13) . ? C69 H69A 0.99 . ? C69 H69B 0.99 . ? C70 C71 1.523(12) . ? C70 H70A 0.99 . ? C70 H70B 0.99 . ? C71 C72 1.492(13) . ? C71 H71A 0.99 . ? C71 H71B 0.99 . ? C72 H72A 0.98 . ? C72 H72B 0.98 . ? C72 H72C 0.98 . ? C70' C71' 1.494(12) . ? C70' H70C 0.99 . ? C70' H70D 0.99 . ? C71' C72' 1.500(16) . ? C71' H71C 0.99 . ? C71' H71D 0.99 . ? C72' H72D 0.98 . ? C72' H72E 0.98 . ? C72' H72F 0.98 . ? 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 Cl2 Hg1 Cl1 114.57(4) . . ? Cl2 Hg1 Cl5 111.04(4) . . ? Cl1 Hg1 Cl5 114.31(4) . . ? Cl2 Hg1 Cl6 110.26(4) . . ? Cl1 Hg1 Cl6 116.11(4) . . ? Cl5 Hg1 Cl6 87.62(3) . . ? Cl4 Hg2 Cl3 114.72(5) . . ? Cl4 Hg2 Cl6 116.52(4) . . ? Cl3 Hg2 Cl6 107.35(4) . . ? Cl4 Hg2 Cl5 110.77(4) . . ? Cl3 Hg2 Cl5 116.46(4) . . ? Cl6 Hg2 Cl5 88.42(3) . . ? Hg1 Cl5 Hg2 91.42(3) . . ? Hg2 Cl6 Hg1 92.49(4) . . ? C6 N1 C2 120.9(5) . . ? C6 N1 C7 120.5(5) . . ? C2 N1 C7 118.5(5) . . ? O2 C2 N1 122.0(5) . . ? O2 C2 N3 121.4(5) . . ? N1 C2 N3 116.6(4) . . ? C4 N3 C2 125.0(4) . . ? C4 N3 H3 111(3) . . ? C2 N3 H3 123(3) . . ? N4 C4 N3 119.0(5) . . ? N4 C4 C5 123.6(5) . . ? N3 C4 C5 117.4(5) . . ? C4 N4 H4A 120 . . ? C4 N4 H4B 120 . . ? H4A N4 H4B 120 . . ? C6 C5 C4 118.0(5) . . ? C6 C5 H5 121 . . ? C4 C5 H5 121 . . ? N1 C6 C5 121.9(5) . . ? N1 C6 H6 119 . . ? C5 C6 H6 119 . . ? N1 C7 C8 113.4(5) . . ? N1 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N1 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C9 115.5(7) . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8A 108.4 . . ? C7 C8 H8B 108.4 . . ? C9 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C10 C9 C8 112.6(8) . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C9 C10 C11 123.9(13) . . ? C9 C10 H10A 106.3 . . ? C11 C10 H10A 106.3 . . ? C9 C10 H10B 106.4 . . ? C11 C10 H10B 106.4 . . ? H10A C10 H10B 106.4 . . ? C12 C11 C10 118.7(14) . . ? C12 C11 H11A 107.6 . . ? C10 C11 H11A 107.6 . . ? C12 C11 H11B 107.6 . . ? C10 C11 H11B 107.6 . . ? H11A C11 H11B 107.1 . . ? C11' C10' H10C 109.3 . . ? C11' C10' H10D 109.3 . . ? H10C C10' H10D 108 . . ? C12' C11' C10' 104.3(11) . . ? C12' C11' H11C 110.9 . . ? C10' C11' H11C 110.9 . . ? C12' C11' H11D 110.9 . . ? C10' C11' H11D 110.9 . . ? H11C C11' H11D 108.9 . . ? C26 N21 C22 120.0(5) . . ? C26 N21 C27 119.6(4) . . ? C22 N21 C27 120.3(4) . . ? O22 C22 N23 121.8(5) . . ? O22 C22 N21 119.0(5) . . ? N23 C22 N21 119.1(4) . . ? C22 N23 C24 120.8(4) . . ? N24 C24 N23 118.5(5) . . ? N24 C24 C25 121.2(5) . . ? N23 C24 C25 120.3(5) . . ? C24 N24 H24A 120 . . ? C24 N24 H24B 120 . . ? H24A N24 H24B 120 . . ? C26 C25 C24 117.4(5) . . ? C26 C25 H25 121.3 . . ? C24 C25 H25 121.3 . . ? N21 C26 C25 122.3(5) . . ? N21 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? N21 C27 C28 111.5(5) . . ? N21 C27 H27A 109.3 . . ? C28 C27 H27A 109.3 . . ? N21 C27 H27B 109.3 . . ? C28 C27 H27B 109.3 . . ? H27A C27 H27B 108 . . ? C27 C28 C29 112.2(5) . . ? C27 C28 H28A 109.2 . . ? C29 C28 H28A 109.2 . . ? C27 C28 H28B 109.2 . . ? C29 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? C30 C29 C28 113.7(7) . . ? C30 C29 H29A 108.8 . . ? C28 C29 H29A 108.8 . . ? C30 C29 H29B 108.8 . . ? C28 C29 H29B 108.8 . . ? H29A C29 H29B 107.7 . . ? C31 C30 C29 112.7(8) . . ? C31 C30 H30A 109 . . ? C29 C30 H30A 109 . . ? C31 C30 H30B 109 . . ? C29 C30 H30B 109 . . ? H30A C30 H30B 107.8 . . ? C30 C31 C32 112.5(9) . . ? C30 C31 H31A 109.1 . . ? C32 C31 H31A 109.1 . . ? C30 C31 H31B 109.1 . . ? C32 C31 H31B 109.1 . . ? H31A C31 H31B 107.8 . . ? C31' C30' H30C 108.6 . . ? C31' C30' H30D 108.5 . . ? H30C C30' H30D 107.5 . . ? C30' C31' C32' 115.5(18) . . ? C30' C31' H31C 108.4 . . ? C32' C31' H31C 108.4 . . ? C30' C31' H31D 108.4 . . ? C32' C31' H31D 108.4 . . ? H31C C31' H31D 107.5 . . ? C31' C32' H32D 109.5 . . ? C31' C32' H32E 109.5 . . ? H32D C32' H32E 109.5 . . ? C31' C32' H32F 109.5 . . ? H32D C32' H32F 109.5 . . ? H32E C32' H32F 109.5 . . ? C46 N41 C42 119.3(5) . . ? C46 N41 C47 119.4(5) . . ? C42 N41 C47 121.2(5) . . ? O42 C42 N43 120.4(5) . . ? O42 C42 N41 118.5(5) . . ? N43 C42 N41 121.1(5) . . ? C44 N43 C42 118.9(4) . . ? N43 C44 N44 118.3(5) . . ? N43 C44 C45 121.9(5) . . ? N44 C44 C45 119.7(5) . . ? C44 N44 H44A 120 . . ? C44 N44 H44B 120 . . ? H44A N44 H44B 120 . . ? C46 C45 C44 116.4(5) . . ? C46 C45 H45 121.8 . . ? C44 C45 H45 121.8 . . ? N41 C46 C45 122.2(5) . . ? N41 C46 H46 118.9 . . ? C45 C46 H46 118.9 . . ? N41 C47 C48 111.7(5) . . ? N41 C47 H47A 109.3 . . ? C48 C47 H47A 109.3 . . ? N41 C47 H47B 109.3 . . ? C48 C47 H47B 109.3 . . ? H47A C47 H47B 107.9 . . ? C49 C48 C47 115.5(7) . . ? C49 C48 H48A 108.4 . . ? C47 C48 H48A 108.4 . . ? C49 C48 H48B 108.4 . . ? C47 C48 H48B 108.4 . . ? H48A C48 H48B 107.5 . . ? C48 C49 C50 122.4(9) . . ? C48 C49 H49A 106.7 . . ? C50 C49 H49A 106.7 . . ? C48 C49 H49B 106.7 . . ? C50 C49 H49B 106.7 . . ? H49A C49 H49B 106.6 . . ? C49 C50 C51 116.8(9) . . ? C49 C50 H50A 108.1 . . ? C51 C50 H50A 108.1 . . ? C49 C50 H50B 108.1 . . ? C51 C50 H50B 108.1 . . ? H50A C50 H50B 107.3 . . ? C52 C51 C50 115.7(14) . . ? C52 C51 H51A 108.4 . . ? C50 C51 H51A 108.4 . . ? C52 C51 H51B 108.3 . . ? C50 C51 H51B 108.4 . . ? H51A C51 H51B 107.4 . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C66 N61 C62 120.9(5) . . ? C66 N61 C67 119.6(5) . . ? C62 N61 C67 119.5(4) . . ? O62 C62 N61 122.7(5) . . ? O62 C62 N63 119.9(5) . . ? N61 C62 N63 117.3(4) . . ? C62 N63 C64 122.3(4) . . ? C62 N63 H63 127(5) . . ? C64 N63 H63 111(5) . . ? N64 C64 N63 117.2(5) . . ? N64 C64 C65 124.1(5) . . ? N63 C64 C65 118.7(5) . . ? C64 N64 H64A 120 . . ? C64 N64 H64B 120 . . ? H64A N64 H64B 120 . . ? C66 C65 C64 117.3(5) . . ? C66 C65 H65 121.4 . . ? C64 C65 H65 121.4 . . ? N61 C66 C65 123.3(5) . . ? N61 C66 H66 118.3 . . ? C65 C66 H66 118.3 . . ? N61 C67 C68 111.9(5) . . ? N61 C67 H67A 109.2 . . ? C68 C67 H67A 109.2 . . ? N61 C67 H67B 109.2 . . ? C68 C67 H67B 109.2 . . ? H67A C67 H67B 107.9 . . ? C67 C68 C69 110.6(6) . . ? C67 C68 H68A 109.5 . . ? C69 C68 H68A 109.5 . . ? C67 C68 H68B 109.5 . . ? C69 C68 H68B 109.5 . . ? H68A C68 H68B 108.1 . . ? C70 C69 C68 116.1(7) . . ? C70 C69 H69A 108.3 . . ? C68 C69 H69A 108.2 . . ? C70 C69 H69B 108.2 . . ? C68 C69 H69B 108.2 . . ? H69A C69 H69B 107.4 . . ? C71 C70 C69 109.0(10) . . ? C71 C70 H70A 109.9 . . ? C69 C70 H70A 109.9 . . ? C71 C70 H70B 109.9 . . ? C69 C70 H70B 109.9 . . ? H70A C70 H70B 108.3 . . ? C72 C71 C70 107.2(10) . . ? C72 C71 H71A 110.3 . . ? C70 C71 H71A 110.3 . . ? C72 C71 H71B 110.3 . . ? C70 C71 H71B 110.3 . . ? H71A C71 H71B 108.5 . . ? C71' C70' H70C 106.8 . . ? C71' C70' H70D 106.8 . . ? H70C C70' H70D 106.7 . . ? C70' C71' C72' 107.8(13) . . ? C70' C71' H71C 110.1 . . ? C72' C71' H71C 110.1 . . ? C70' C71' H71D 110.1 . . ? C72' C71' H71D 110.1 . . ? H71C C71' H71D 108.5 . . ? 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 Cl2 Hg1 Cl5 Hg2 -109.34(4) . . . . ? Cl1 Hg1 Cl5 Hg2 119.16(4) . . . . ? Cl6 Hg1 Cl5 Hg2 1.47(3) . . . . ? Cl4 Hg2 Cl5 Hg1 116.35(4) . . . . ? Cl3 Hg2 Cl5 Hg1 -110.14(4) . . . . ? Cl6 Hg2 Cl5 Hg1 -1.51(3) . . . . ? Cl4 Hg2 Cl6 Hg1 -111.01(4) . . . . ? Cl3 Hg2 Cl6 Hg1 118.78(4) . . . . ? Cl5 Hg2 Cl6 Hg1 1.49(3) . . . . ? Cl2 Hg1 Cl6 Hg2 110.06(4) . . . . ? Cl1 Hg1 Cl6 Hg2 -117.52(4) . . . . ? Cl5 Hg1 Cl6 Hg2 -1.52(3) . . . . ? C6 N1 C2 O2 179.7(5) . . . . ? C7 N1 C2 O2 -1.7(6) . . . . ? C6 N1 C2 N3 0.4(6) . . . . ? C7 N1 C2 N3 179.0(4) . . . . ? O2 C2 N3 C4 -179.1(4) . . . . ? N1 C2 N3 C4 0.1(6) . . . . ? C2 N3 C4 N4 -179.9(4) . . . . ? C2 N3 C4 C5 -1.6(7) . . . . ? N4 C4 C5 C6 -179.4(5) . . . . ? N3 C4 C5 C6 2.4(7) . . . . ? C2 N1 C6 C5 0.5(8) . . . . ? C7 N1 C6 C5 -178.0(5) . . . . ? C4 C5 C6 N1 -2.0(8) . . . . ? C6 N1 C7 C8 93.7(7) . . . . ? C2 N1 C7 C8 -84.9(6) . . . . ? N1 C7 C8 C9 -170.2(6) . . . . ? C7 C8 C9 C10 -86.1(12) . . . . ? C8 C9 C10 C11 -165.7(15) . . . . ? C9 C10 C11 C12 -75(2) . . . . ? C26 N21 C22 O22 -179.9(5) . . . . ? C27 N21 C22 O22 -3.2(7) . . . . ? C26 N21 C22 N23 -0.5(7) . . . . ? C27 N21 C22 N23 176.2(4) . . . . ? O22 C22 N23 C24 -179.3(5) . . . . ? N21 C22 N23 C24 1.4(7) . . . . ? C22 N23 C24 N24 -179.7(5) . . . . ? C22 N23 C24 C25 -1.4(7) . . . . ? N24 C24 C25 C26 178.8(5) . . . . ? N23 C24 C25 C26 0.5(7) . . . . ? C22 N21 C26 C25 -0.4(8) . . . . ? C27 N21 C26 C25 -177.1(5) . . . . ? C24 C25 C26 N21 0.4(8) . . . . ? C26 N21 C27 C28 84.8(6) . . . . ? C22 N21 C27 C28 -91.9(6) . . . . ? N21 C27 C28 C29 -179.5(5) . . . . ? C27 C28 C29 C30 174.6(6) . . . . ? C28 C29 C30 C31 71.3(10) . . . . ? C29 C30 C31 C32 80.6(12) . . . . ? C46 N41 C42 O42 176.8(5) . . . . ? C47 N41 C42 O42 -0.6(8) . . . . ? C46 N41 C42 N43 -2.8(8) . . . . ? C47 N41 C42 N43 179.8(5) . . . . ? O42 C42 N43 C44 -177.0(5) . . . . ? N41 C42 N43 C44 2.6(7) . . . . ? C42 N43 C44 N44 180.0(4) . . . . ? C42 N43 C44 C45 -1.8(7) . . . . ? N43 C44 C45 C46 1.1(8) . . . . ? N44 C44 C45 C46 179.4(5) . . . . ? C42 N41 C46 C45 2.2(8) . . . . ? C47 N41 C46 C45 179.6(6) . . . . ? C44 C45 C46 N41 -1.3(8) . . . . ? C46 N41 C47 C48 104.3(7) . . . . ? C42 N41 C47 C48 -78.3(7) . . . . ? N41 C47 C48 C49 -72.8(8) . . . . ? C47 C48 C49 C50 173.3(7) . . . . ? C48 C49 C50 C51 179.3(10) . . . . ? C49 C50 C51 C52 169.7(12) . . . . ? C66 N61 C62 O62 176.8(5) . . . . ? C67 N61 C62 O62 -2.1(6) . . . . ? C66 N61 C62 N63 -3.5(6) . . . . ? C67 N61 C62 N63 177.6(4) . . . . ? O62 C62 N63 C64 -179.5(4) . . . . ? N61 C62 N63 C64 0.7(6) . . . . ? C62 N63 C64 N64 -176.7(4) . . . . ? C62 N63 C64 C65 2.6(7) . . . . ? N64 C64 C65 C66 176.1(5) . . . . ? N63 C64 C65 C66 -3.2(7) . . . . ? C62 N61 C66 C65 3.0(8) . . . . ? C67 N61 C66 C65 -178.2(5) . . . . ? C64 C65 C66 N61 0.5(8) . . . . ? C66 N61 C67 C68 -77.7(7) . . . . ? C62 N61 C67 C68 101.2(6) . . . . ? N61 C67 C68 C69 177.1(5) . . . . ? C67 C68 C69 C70 -160.9(9) . . . . ? C68 C69 C70 C71 178.4(9) . . . . ? C69 C70 C71 C72 168.6(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4A O42 0.88 1.87 2.745(6) 176 . N4 H4B Cl1 0.88 2.47 3.343(4) 169.4 . N3 H3 N43 1.27(7) 1.57(7) 2.826(6) 168(6) . N24 H24A O62 0.88 2 2.883(6) 176.7 . N24 H24B Cl3 0.88 2.48 3.350(4) 170.3 . N63 H63 N23 1.28(9) 1.55(9) 2.795(6) 160(8) . N44 H44A O2 0.88 2.02 2.895(6) 177.9 . N44 H44B Cl2 0.88 2.39 3.266(5) 176.5 4_465 N64 H64A O22 0.88 1.89 2.771(5) 174.4 . N64 H64B Cl4 0.88 2.59 3.426(4) 159.8 4_465 # END of CIF