# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data__BCHDSulfone _database_code_depnum_ccdc_archive 'CCDC 887832' #TrackingRef '11999_web_deposit_cif_file_0_HidemitsuUno_1340112161.BCHDSulfone.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C17 H20 O3 S' _chemical_formula_moiety 'C17 H20 O3 S' _chemical_formula_weight 304.40 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 32.099(6) _cell_length_b 6.2507(5) _cell_length_c 18.637(3) _cell_angle_alpha 90.0000 _cell_angle_beta 122.027(6) _cell_angle_gamma 90.0000 _cell_volume 3170.2(8) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4614 _cell_measurement_theta_min 3.33 _cell_measurement_theta_max 27.47 _cell_measurement_temperature 150(2) #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296.00 _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.874 _exptl_absorpt_correction_T_max 0.979 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 150(2) _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku Mercury-8' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 14.6199 _diffrn_reflns_number 11735 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Coordinates of hydrogen atoms on the bicyclo[2.2.1]heptadiene moiety are refined isotropically. Aromatic hydrogen atoms are allowed to ride on the attached carbon atoms with 1.2 x Beq, and the bond lengths are refined. Hydrogen atoms of the t-butyl group are allowed to ride on the attached carbon atoms, rotate about the C-C bonds, and stretch the bond lengths to seek the best positions. ; _reflns_number_total 3619 _reflns_number_gt 3172 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0988 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 3619 _refine_ls_number_parameters 231 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0468P)^2^+1.7522P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_diff_density_max 0.280 _refine_diff_density_min -0.410 _refine_ls_extinction_method none _iucr_refine_instructions_details ; TITL _BCHDSulfone CELL 0.71070 32.09900 6.25070 18.63700 90.000 122.027 90.000 ZERR 8 0.00540 0.00050 0.00240 0.000 0.005 0.000 LATT 7 SYMM -X, +Y, .50-Z SFAC C H O S UNIT 136 160 24 8 MERG 2 SHEL 99999.000000 0.000000 FMAP 2 PLAN -25 SIZE 0.10 0.50 0.50 ACTA BOND $H CONF WPDB -2 L.S. 5 TEMP -123.10 HTAB WGHT 0.046800 1.752200 FVAR 3.52371 0.00000 S1 4 0.110452 0.191112 0.616662 11.00000 0.02231 0.02999 = 0.02137 0.00211 0.00920 0.00143 O1 3 0.148682 0.540632 0.471873 11.00000 0.03444 0.05382 = 0.02446 0.00962 0.01634 0.01302 O2 3 0.093226 0.333228 0.656078 11.00000 0.03333 0.04761 = 0.02704 -0.00475 0.01760 0.00183 O3 3 0.129726 -0.014787 0.654554 11.00000 0.03007 0.03358 = 0.03433 0.01179 0.00978 0.00264 C1 1 0.184865 0.231488 0.574287 11.00000 0.02432 0.03016 = 0.02472 -0.00373 0.01100 -0.00038 H1 2 0.170673 0.106531 0.535571 11.00000 0.02796 C2 1 0.155073 0.325176 0.608916 11.00000 0.02146 0.02846 = 0.01950 -0.00012 0.00780 0.00089 C3 1 0.171254 0.522427 0.637444 11.00000 0.02771 0.02863 = 0.02149 -0.00109 0.00869 0.00138 H3 2 0.160546 0.616743 0.664224 11.00000 0.03788 C4 1 0.212914 0.564598 0.622723 11.00000 0.03014 0.02891 = 0.03198 -0.00059 0.01232 -0.00479 H4 2 0.222408 0.713363 0.625139 11.00000 0.03911 C5 1 0.254335 0.407599 0.677418 11.00000 0.02386 0.04175 = 0.02884 0.00063 0.00853 -0.00295 H5 2 0.286140 0.447870 0.722957 11.00000 0.03670 C6 1 0.237997 0.211669 0.649205 11.00000 0.02406 0.03602 = 0.02871 0.00224 0.01148 0.00286 H6 2 0.256057 0.071964 0.671810 11.00000 0.04148 C7 1 0.191773 0.445636 0.536896 11.00000 0.02608 0.03837 = 0.02715 0.00391 0.01367 0.00250 H7 2 0.216773 0.425814 0.521845 11.00000 0.02947 C8 1 0.062077 0.149240 0.510892 11.00000 0.01924 0.02885 = 0.02450 0.00067 0.01045 0.00054 C9 1 0.054821 -0.050500 0.474566 11.00000 0.02502 0.03048 = 0.03929 -0.00328 0.00965 0.00342 AFIX 48 H9 2 0.075633 -0.160072 0.503765 11.00000 -1.20000 AFIX 0 C10 1 0.015206 -0.081062 0.392711 11.00000 0.03217 0.03981 = 0.04300 -0.01517 0.01151 -0.00256 AFIX 48 H10 2 0.009518 -0.220517 0.366561 11.00000 -1.20000 AFIX 0 C11 1 -0.016049 0.085251 0.348432 11.00000 0.02579 0.05120 = 0.02809 -0.00489 0.00699 -0.00058 AFIX 48 H11 2 -0.043686 0.062161 0.291220 11.00000 -1.20000 AFIX 0 C12 1 -0.008253 0.285331 0.385112 11.00000 0.03349 0.04231 = 0.03330 0.00532 0.00499 0.00973 AFIX 48 H12 2 -0.029621 0.398768 0.354625 11.00000 -1.20000 AFIX 0 C13 1 0.031061 0.318158 0.466765 11.00000 0.03403 0.02980 = 0.03119 -0.00067 0.00877 0.00637 AFIX 48 H13 2 0.036698 0.455154 0.492253 11.00000 -1.20000 AFIX 0 C14 1 0.140608 0.540241 0.387170 11.00000 0.03395 0.04218 = 0.02225 0.00196 0.01535 0.00179 C15 1 0.089686 0.638157 0.333737 11.00000 0.03923 0.06271 = 0.02735 0.00926 0.01683 0.01143 AFIX 138 H15A 2 0.065571 0.545875 0.335888 11.00000 -1.50000 H15B 2 0.081065 0.651338 0.274830 11.00000 -1.50000 H15C 2 0.089495 0.780569 0.355942 11.00000 -1.50000 AFIX 0 C16 1 0.141019 0.314429 0.358146 11.00000 0.04177 0.04584 = 0.04181 -0.00899 0.01753 -0.00199 AFIX 138 H16A 2 0.173289 0.253705 0.393459 11.00000 -1.50000 H16B 2 0.132612 0.317132 0.300290 11.00000 -1.50000 H16C 2 0.117416 0.228851 0.362232 11.00000 -1.50000 AFIX 0 C17 1 0.178873 0.680627 0.385705 11.00000 0.04568 0.04870 = 0.03716 0.00620 0.02254 -0.00347 AFIX 138 H17A 2 0.178720 0.825663 0.408064 11.00000 -1.50000 H17B 2 0.170945 0.693694 0.326317 11.00000 -1.50000 H17C 2 0.212075 0.614687 0.421772 11.00000 -1.50000 HKLF 4 REM _BCHDSulfone REM R1 = 0.0377 for 3172 Fo > 4sig(Fo) and 0.0429 for all 3619 data REM 231 parameters refined using 0 restraints END WGHT 0.0468 1.7520 REM Highest difference peak 0.282, deepest hole -0.413, 1-sigma level 0.042 Q1 1 0.0813 0.1661 0.5538 11.00000 0.05 0.28 Q2 1 0.1310 0.3069 0.5922 11.00000 0.05 0.23 Q3 1 0.1419 0.4049 0.4597 11.00000 0.05 0.23 Q4 1 0.1646 0.2815 0.5932 11.00000 0.05 0.22 Q5 1 0.2032 0.5162 0.5788 11.00000 0.05 0.21 Q6 1 0.1684 0.3782 0.6400 11.00000 0.05 0.21 Q7 1 0.1099 0.4174 0.6185 11.00000 0.05 0.20 Q8 1 0.2128 0.2226 0.6098 11.00000 0.05 0.19 Q9 1 0.1894 0.3205 0.5519 11.00000 0.05 0.19 Q10 1 0.0496 0.2225 0.4987 11.00000 0.05 0.19 Q11 1 0.2518 0.3137 0.6487 11.00000 0.05 0.17 Q12 1 0.0129 0.0253 0.3619 11.00000 0.05 0.17 Q13 1 0.1137 0.5882 0.3611 11.00000 0.05 0.17 Q14 1 0.2363 0.5157 0.6560 11.00000 0.05 0.17 Q15 1 0.0671 -0.2061 0.5319 11.00000 0.05 0.16 Q16 1 0.1910 0.5617 0.6293 11.00000 0.05 0.16 Q17 1 0.1404 0.4320 0.3685 11.00000 0.05 0.15 Q18 1 0.1520 0.4387 0.5985 11.00000 0.05 0.15 Q19 1 0.0180 0.3106 0.4200 11.00000 0.05 0.15 Q20 1 -0.0113 0.1766 0.3764 11.00000 0.05 0.14 Q21 1 0.0368 -0.0599 0.4240 11.00000 0.05 0.14 Q22 1 0.0626 0.3157 0.6241 11.00000 0.05 0.13 Q23 1 0.0697 0.4418 0.3302 11.00000 0.05 0.13 Q24 1 0.1747 0.0325 0.7125 11.00000 0.05 0.13 Q25 1 0.0068 0.2933 0.4368 11.00000 0.05 0.12 ; 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.1246 0.1234 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S1 S 0.110452(12) 0.19111(5) 0.61666(2) 0.02572(12) Uani 1 1 d . . . O1 O 0.14868(4) 0.54063(19) 0.47187(6) 0.0372(3) Uani 1 1 d . . . O2 O 0.09323(4) 0.33323(18) 0.65608(6) 0.0352(3) Uani 1 1 d . . . O3 O 0.12973(4) -0.01479(17) 0.65455(6) 0.0362(3) Uani 1 1 d . . . C1 C 0.18486(5) 0.2315(2) 0.57429(9) 0.0274(3) Uani 1 1 d . . . H1 H 0.1707(5) 0.107(2) 0.5356(9) 0.028(4) Uiso 1 1 d . . . C2 C 0.15507(5) 0.3252(2) 0.60892(8) 0.0246(3) Uani 1 1 d . . . C3 C 0.17125(5) 0.5224(2) 0.63744(8) 0.0281(3) Uani 1 1 d . . . H3 H 0.1605(6) 0.617(3) 0.6642(11) 0.038(4) Uiso 1 1 d . . . C4 C 0.21291(5) 0.5646(2) 0.62272(9) 0.0324(3) Uani 1 1 d . . . H4 H 0.2224(6) 0.713(3) 0.6251(10) 0.039(5) Uiso 1 1 d . . . C5 C 0.25433(5) 0.4076(3) 0.67742(9) 0.0342(3) Uani 1 1 d . . . H5 H 0.2861(6) 0.448(3) 0.7230(10) 0.037(4) Uiso 1 1 d . . . C6 C 0.23800(5) 0.2117(2) 0.64920(9) 0.0308(3) Uani 1 1 d . . . H6 H 0.2561(6) 0.072(3) 0.6718(10) 0.041(5) Uiso 1 1 d . . . C7 C 0.19177(5) 0.4456(2) 0.53690(9) 0.0308(3) Uani 1 1 d . . . H7 H 0.2168(6) 0.426(2) 0.5218(9) 0.029(4) Uiso 1 1 d . . . C8 C 0.06208(5) 0.1492(2) 0.51089(8) 0.0248(3) Uani 1 1 d . . . C9 C 0.05482(5) -0.0505(2) 0.47457(10) 0.0352(3) Uani 1 1 d . . . H9 H 0.0756(4) -0.160(2) 0.5038(6) 0.042 Uiso 1 1 calc R . . C10 C 0.01521(6) -0.0811(3) 0.39271(11) 0.0425(4) Uani 1 1 d . . . H10 H 0.00952(13) -0.221(3) 0.3666(5) 0.051 Uiso 1 1 calc R . . C11 C -0.01605(5) 0.0853(3) 0.34843(10) 0.0386(4) Uani 1 1 d . . . H11 H -0.0437(5) 0.0622(5) 0.2912(11) 0.046 Uiso 1 1 calc R . . C12 C -0.00825(6) 0.2853(3) 0.38511(10) 0.0426(4) Uani 1 1 d . . . H12 H -0.0296(4) 0.399(2) 0.3546(6) 0.051 Uiso 1 1 calc R . . C13 C 0.03106(6) 0.3182(2) 0.46677(10) 0.0359(3) Uani 1 1 d . . . H13 H 0.03670(12) 0.455(3) 0.4923(5) 0.043 Uiso 1 1 calc R . . C14 C 0.14061(5) 0.5402(2) 0.38717(9) 0.0326(3) Uani 1 1 d . . . C15 C 0.08969(6) 0.6382(3) 0.33374(10) 0.0435(4) Uani 1 1 d . . . H15A H 0.0656(3) 0.5459(14) 0.3359(6) 0.065 Uiso 1 1 calc R . . H15B H 0.0811(2) 0.6513(19) 0.2748(7) 0.065 Uiso 1 1 calc R . . H15C H 0.08950(13) 0.7806(18) 0.3559(5) 0.065 Uiso 1 1 calc R . . C16 C 0.14102(7) 0.3144(3) 0.35815(11) 0.0454(4) Uani 1 1 d . . . H16A H 0.1733(4) 0.2537(10) 0.3935(6) 0.068 Uiso 1 1 calc R . . H16B H 0.1326(5) 0.3171(3) 0.3003(7) 0.068 Uiso 1 1 calc R . . H16C H 0.1174(4) 0.2289(12) 0.3622(8) 0.068 Uiso 1 1 calc R . . C17 C 0.17887(7) 0.6806(3) 0.38571(11) 0.0436(4) Uani 1 1 d . . . H17A H 0.1787(3) 0.8257(17) 0.4081(8) 0.065 Uiso 1 1 calc R . . H17B H 0.1709(3) 0.6937(17) 0.3263(7) 0.065 Uiso 1 1 calc R . . H17C H 0.2121(4) 0.6147(13) 0.4218(7) 0.065 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.02231(18) 0.0300(2) 0.02137(18) 0.00211(12) 0.00920(14) 0.00143(12) O1 0.0344(6) 0.0538(7) 0.0245(5) 0.0096(5) 0.0163(4) 0.0130(5) O2 0.0333(5) 0.0476(6) 0.0270(5) -0.0048(4) 0.0176(5) 0.0018(5) O3 0.0301(5) 0.0336(5) 0.0343(5) 0.0118(4) 0.0098(4) 0.0026(4) C1 0.0243(6) 0.0302(7) 0.0247(7) -0.0037(6) 0.0110(6) -0.0004(5) C2 0.0215(6) 0.0285(7) 0.0195(6) -0.0001(5) 0.0078(5) 0.0009(5) C3 0.0277(7) 0.0286(7) 0.0215(6) -0.0011(5) 0.0087(5) 0.0014(5) C4 0.0301(7) 0.0289(7) 0.0320(7) -0.0006(6) 0.0123(6) -0.0048(6) C5 0.0239(7) 0.0417(8) 0.0288(7) 0.0006(6) 0.0085(6) -0.0030(6) C6 0.0241(7) 0.0360(8) 0.0287(7) 0.0022(6) 0.0115(6) 0.0029(6) C7 0.0261(7) 0.0384(8) 0.0271(7) 0.0039(6) 0.0137(6) 0.0025(6) C8 0.0192(6) 0.0288(6) 0.0245(6) 0.0007(5) 0.0105(5) 0.0005(5) C9 0.0250(7) 0.0305(7) 0.0393(8) -0.0033(6) 0.0096(6) 0.0034(6) C10 0.0322(8) 0.0398(9) 0.0430(9) -0.0152(7) 0.0115(7) -0.0026(7) C11 0.0258(7) 0.0512(9) 0.0281(7) -0.0049(7) 0.0070(6) -0.0006(7) C12 0.0335(8) 0.0423(9) 0.0333(8) 0.0053(7) 0.0050(7) 0.0097(7) C13 0.0340(8) 0.0298(7) 0.0312(8) -0.0007(6) 0.0088(6) 0.0064(6) C14 0.0339(7) 0.0422(8) 0.0223(7) 0.0020(6) 0.0154(6) 0.0018(6) C15 0.0392(9) 0.0627(11) 0.0273(8) 0.0093(7) 0.0168(7) 0.0114(8) C16 0.0418(9) 0.0458(10) 0.0418(9) -0.0090(7) 0.0175(8) -0.0020(7) C17 0.0457(9) 0.0487(10) 0.0372(9) 0.0062(7) 0.0225(8) -0.0035(8) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # 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 S1 O2 1.4371(10) . ? S1 O3 1.4403(10) . ? S1 C2 1.7303(14) . ? S1 C8 1.7660(13) . ? O1 C7 1.3987(17) . ? O1 C14 1.4578(16) . ? C1 C2 1.5260(18) . ? C1 C6 1.5323(19) . ? C1 C7 1.578(2) . ? C1 H1 0.995(15) . ? C2 C3 1.3341(19) . ? C3 C4 1.524(2) . ? C3 H3 0.947(17) . ? C4 C5 1.527(2) . ? C4 C7 1.556(2) . ? C4 H4 0.972(18) . ? C5 C6 1.326(2) . ? C5 H5 0.952(17) . ? C6 H6 1.009(18) . ? C7 H7 0.988(16) . ? C8 C9 1.3799(19) . ? C8 C13 1.3835(19) . ? C9 C10 1.387(2) . ? C9 H9 0.9088 . ? C10 C11 1.375(2) . ? C10 H10 0.9676 . ? C11 C12 1.383(2) . ? C11 H11 0.9703 . ? C12 C13 1.383(2) . ? C12 H12 0.9395 . ? C13 H13 0.9490 . ? C14 C16 1.514(2) . ? C14 C15 1.520(2) . ? C14 C17 1.522(2) . ? C15 H15A 0.9831 . ? C15 H15B 0.9831 . ? C15 H15C 0.9831 . ? C16 H16A 0.9629 . ? C16 H16B 0.9629 . ? C16 H16C 0.9629 . ? C17 H17A 0.9989 . ? C17 H17B 0.9989 . ? C17 H17C 0.9989 . ? 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 O2 S1 O3 118.91(7) . . ? O2 S1 C2 107.65(7) . . ? O3 S1 C2 108.32(6) . . ? O2 S1 C8 108.26(6) . . ? O3 S1 C8 108.04(6) . . ? C2 S1 C8 104.80(6) . . ? C7 O1 C14 117.63(11) . . ? C2 C1 C6 106.86(11) . . ? C2 C1 C7 97.33(11) . . ? C6 C1 C7 97.00(11) . . ? C2 C1 H1 117.4(9) . . ? C6 C1 H1 117.2(9) . . ? C7 C1 H1 117.6(9) . . ? C3 C2 C1 108.93(12) . . ? C3 C2 S1 125.37(11) . . ? C1 C2 S1 125.56(10) . . ? C2 C3 C4 106.35(13) . . ? C2 C3 H3 127.7(10) . . ? C4 C3 H3 125.8(10) . . ? C3 C4 C5 107.77(12) . . ? C3 C4 C7 99.00(11) . . ? C5 C4 C7 97.46(12) . . ? C3 C4 H4 116.1(10) . . ? C5 C4 H4 116.3(10) . . ? C7 C4 H4 117.4(10) . . ? C6 C5 C4 107.91(13) . . ? C6 C5 H5 127.5(10) . . ? C4 C5 H5 124.6(10) . . ? C5 C6 C1 107.56(13) . . ? C5 C6 H6 128.0(10) . . ? C1 C6 H6 124.5(10) . . ? O1 C7 C4 112.31(12) . . ? O1 C7 C1 115.89(12) . . ? C4 C7 C1 92.19(11) . . ? O1 C7 H7 112.7(9) . . ? C4 C7 H7 112.0(9) . . ? C1 C7 H7 110.1(9) . . ? C9 C8 C13 121.19(13) . . ? C9 C8 S1 120.10(11) . . ? C13 C8 S1 118.68(11) . . ? C8 C9 C10 118.82(14) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 120.51(15) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.26(14) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C13 119.89(15) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C8 119.33(14) . . ? C12 C13 H13 120.3 . . ? C8 C13 H13 120.3 . . ? O1 C14 C16 110.99(13) . . ? O1 C14 C15 102.74(11) . . ? C16 C14 C15 110.57(14) . . ? O1 C14 C17 109.68(12) . . ? C16 C14 C17 111.79(13) . . ? C15 C14 C17 110.72(14) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 C6 C1 C2 C3 64.31(14) . . . . ? C7 C1 C2 C3 -35.32(13) . . . . ? C6 C1 C2 S1 -111.61(12) . . . . ? C7 C1 C2 S1 148.76(10) . . . . ? O2 S1 C2 C3 2.08(14) . . . . ? O3 S1 C2 C3 -127.69(12) . . . . ? C8 S1 C2 C3 117.17(12) . . . . ? O2 S1 C2 C1 177.35(11) . . . . ? O3 S1 C2 C1 47.58(13) . . . . ? C8 S1 C2 C1 -67.56(12) . . . . ? C1 C2 C3 C4 -0.32(14) . . . . ? S1 C2 C3 C4 175.61(10) . . . . ? C2 C3 C4 C5 -64.28(15) . . . . ? C2 C3 C4 C7 36.60(14) . . . . ? C3 C4 C5 C6 65.04(16) . . . . ? C7 C4 C5 C6 -36.95(15) . . . . ? C4 C5 C6 C1 0.06(16) . . . . ? C2 C1 C6 C5 -63.66(15) . . . . ? C7 C1 C6 C5 36.21(14) . . . . ? C14 O1 C7 C4 144.61(13) . . . . ? C14 O1 C7 C1 -111.21(14) . . . . ? C3 C4 C7 O1 64.81(14) . . . . ? C5 C4 C7 O1 174.22(12) . . . . ? C3 C4 C7 C1 -54.41(12) . . . . ? C5 C4 C7 C1 55.00(12) . . . . ? C2 C1 C7 O1 -62.95(14) . . . . ? C6 C1 C7 O1 -171.03(12) . . . . ? C2 C1 C7 C4 53.21(11) . . . . ? C6 C1 C7 C4 -54.87(11) . . . . ? O2 S1 C8 C9 -141.43(12) . . . . ? O3 S1 C8 C9 -11.43(14) . . . . ? C2 S1 C8 C9 103.90(13) . . . . ? O2 S1 C8 C13 36.59(13) . . . . ? O3 S1 C8 C13 166.59(12) . . . . ? C2 S1 C8 C13 -78.08(13) . . . . ? C13 C8 C9 C10 -0.9(2) . . . . ? S1 C8 C9 C10 177.10(12) . . . . ? C8 C9 C10 C11 0.4(2) . . . . ? C9 C10 C11 C12 0.1(3) . . . . ? C10 C11 C12 C13 -0.2(3) . . . . ? C11 C12 C13 C8 -0.2(3) . . . . ? C9 C8 C13 C12 0.8(2) . . . . ? S1 C8 C13 C12 -177.23(13) . . . . ? C7 O1 C14 C16 57.51(17) . . . . ? C7 O1 C14 C15 175.71(13) . . . . ? C7 O1 C14 C17 -66.50(17) . . . . ? #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data_BCODpyrroleOtBu _database_code_depnum_ccdc_archive 'CCDC 887833' #TrackingRef '12000_web_deposit_cif_file_0_HidemitsuUno_1340112451.BCHDPyrrole.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C16 H21 N O3' _chemical_formula_moiety 'C16 H21 N O3' _chemical_formula_weight 275.35 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 8.651(4) _cell_length_b 9.558(4) _cell_length_c 17.186(7) _cell_angle_alpha 90.0000 _cell_angle_beta 94.300(6) _cell_angle_gamma 90.0000 _cell_volume 1417.1(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5154 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 31.02 _cell_measurement_temperature 120(2) #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.080 _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592.00 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_T_max 0.993 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 120(0) _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Saturn724' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.222 _diffrn_reflns_number 22439 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_standards_number 0 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Hydrogen atoms are refined isotropically except for H9, Biso value of which rides on the attached carbon atom. ; _reflns_number_total 3266 _reflns_number_gt 3139 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0950 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 3264 _refine_ls_number_parameters 255 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.6124P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_diff_density_max 0.300 _refine_diff_density_min -0.280 _refine_ls_extinction_method none _iucr_refine_instructions_details ; TITL BCODpyrroleOtBu CELL 0.71075 8.65090 9.55840 17.18590 90.000 94.300 90.000 ZERR 4 0.00340 0.00380 0.00650 0.000 0.005 0.000 LATT 1 SYMM -X, .50+Y, .50-Z SFAC C H N O UNIT 64 84 4 12 SHEL 99999.000000 0.769625 L.S. 5 FMAP 2 PLAN -5 WPDB -2 HTAB BOND $H CONF TEMP -152.8 ACTA SIZE 0.200 0.120 0.080 WGHT 0.046600 0.612400 FVAR 0.71128 0.02482 0.03738 0.02903 0.02591 0.02650 O1 4 0.326679 0.822076 0.482543 11.00000 0.01298 0.01444 = 0.01422 0.00337 0.00173 0.00211 O2 4 0.644648 0.655291 0.706942 11.00000 0.01526 0.01942 = 0.01956 -0.00139 -0.00474 0.00245 O3 4 0.718844 0.435243 0.679062 11.00000 0.02212 0.02050 = 0.03103 -0.00066 -0.00698 0.00711 N1 3 0.453990 0.409820 0.572398 11.00000 0.01641 0.01374 = 0.01771 0.00043 0.00082 0.00258 H1 2 0.523564 0.343511 0.564171 11.00000 0.02757 C1 1 0.487296 0.527775 0.617700 11.00000 0.01489 0.01476 = 0.01442 0.00145 0.00232 0.00011 C2 1 0.315761 0.428056 0.529192 11.00000 0.01746 0.01441 = 0.01532 0.00060 0.00101 -0.00193 H2 2 0.279203 0.355568 0.493301 11.00000 0.02082 C3 1 0.259459 0.557490 0.547249 11.00000 0.01335 0.01510 = 0.01363 0.00132 0.00137 -0.00100 C4 1 0.125392 0.658297 0.533200 11.00000 0.01217 0.01680 = 0.01437 0.00071 -0.00002 -0.00009 H4 2 0.053972 0.646418 0.485923 11.00000 0.01736 C5 1 0.049752 0.671473 0.610889 11.00000 0.01440 0.02148 = 0.01849 0.00303 0.00395 0.00229 H5 2 -0.054301 0.636096 0.619866 11.00000 0.02732 C6 1 0.151351 0.731798 0.662592 11.00000 0.01730 0.02022 = 0.01555 0.00125 0.00354 0.00383 H6 2 0.138196 0.751885 0.717423 11.00000 0.02472 C7 1 0.300826 0.761683 0.622409 11.00000 0.01408 0.01545 = 0.01288 -0.00037 0.00040 0.00120 H7 2 0.370679 0.830754 0.647653 11.00000 0.01606 C8 1 0.366773 0.620466 0.602250 11.00000 0.01335 0.01422 = 0.01233 0.00152 0.00175 -0.00034 C9 1 0.220278 0.799329 0.540175 11.00000 0.01309 0.01481 = 0.01359 -0.00031 0.00135 0.00141 H9 2 0.150520 0.881011 0.544571 11.00000 -1.20000 C10 1 0.627597 0.531304 0.669818 11.00000 0.01468 0.01681 = 0.01603 0.00313 0.00209 0.00111 C11 1 0.772011 0.663652 0.766890 11.00000 0.01522 0.02387 = 0.01538 0.00229 -0.00240 0.00107 H11A 2 0.863833 0.616953 0.747954 11.00000 21.00000 H11B 2 0.738448 0.612730 0.812891 11.00000 21.00000 C12 1 0.800407 0.815965 0.783860 11.00000 0.02144 0.02555 = 0.02147 -0.00523 -0.00541 0.00518 H12A 2 0.838406 0.864479 0.736986 11.00000 31.00000 H12B 2 0.879058 0.826205 0.828893 11.00000 31.00000 H12C 2 0.707350 0.861878 0.797951 11.00000 31.00000 C13 1 0.278358 0.922293 0.421039 11.00000 0.01441 0.01331 = 0.01417 0.00268 -0.00120 0.00098 C14 1 0.279154 1.070477 0.454205 11.00000 0.02127 0.01324 = 0.02045 -0.00013 -0.00146 0.00143 H14A 2 0.200935 1.083846 0.494787 11.00000 41.00000 H14B 2 0.247269 1.137967 0.411521 11.00000 41.00000 H14C 2 0.383865 1.095340 0.477558 11.00000 41.00000 C15 1 0.119347 0.882579 0.382938 11.00000 0.01582 0.02024 = 0.01739 0.00139 -0.00263 -0.00046 H15A 2 0.121895 0.784878 0.363841 11.00000 51.00000 H15B 2 0.095613 0.944413 0.337866 11.00000 51.00000 H15C 2 0.034998 0.893739 0.419626 11.00000 51.00000 C16 1 0.401236 0.908804 0.362320 11.00000 0.01855 0.01886 = 0.01718 0.00430 0.00169 0.00138 H16A 2 0.508244 0.924435 0.388625 11.00000 61.00000 H16B 2 0.381706 0.980152 0.321352 11.00000 61.00000 H16C 2 0.398371 0.815540 0.336904 11.00000 61.00000 HKLF 4 REM BCODpyrroleOtBu REM R1 = 0.0396 for 3139 Fo > 4sig(Fo) and 0.0413 for all 3264 data REM 255 parameters refined using 0 restraints END WGHT 0.0466 0.6118 REM Highest difference peak 0.297, deepest hole -0.277, 1-sigma level 0.046 Q1 1 0.3211 0.5958 0.5699 11.00000 0.05 0.30 Q2 1 0.1641 0.7308 0.5333 11.00000 0.05 0.25 Q3 1 0.2331 0.7466 0.6459 11.00000 0.05 0.24 Q4 1 0.2687 0.4878 0.5413 11.00000 0.05 0.24 Q5 1 0.3420 0.9184 0.3923 11.00000 0.05 0.23 ; 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.32668(8) 0.82208(8) 0.48254(4) 0.01384(17) Uani 1 1 d . . . O2 O 0.64465(9) 0.65529(8) 0.70694(4) 0.01839(18) Uani 1 1 d . . . O3 O 0.71884(10) 0.43524(9) 0.67906(5) 0.0250(2) Uani 1 1 d . . . N1 N 0.45399(11) 0.40982(10) 0.57240(5) 0.0160(2) Uani 1 1 d . . . H1 H 0.5236(18) 0.3435(17) 0.5642(9) 0.028(4) Uiso 1 1 d . . . C1 C 0.48730(12) 0.52778(11) 0.61770(6) 0.0146(2) Uani 1 1 d . . . C2 C 0.31576(12) 0.42806(11) 0.52919(6) 0.0157(2) Uani 1 1 d . . . H2 H 0.2792(16) 0.3556(15) 0.4933(8) 0.021(3) Uiso 1 1 d . . . C3 C 0.25946(12) 0.55749(11) 0.54725(6) 0.0140(2) Uani 1 1 d . . . C4 C 0.12539(12) 0.65830(11) 0.53320(6) 0.0145(2) Uani 1 1 d . . . H4 H 0.0540(16) 0.6464(14) 0.4859(8) 0.017(3) Uiso 1 1 d . . . C5 C 0.04975(13) 0.67147(12) 0.61089(6) 0.0180(2) Uani 1 1 d . . . H5 H -0.0543(18) 0.6361(16) 0.6199(8) 0.027(4) Uiso 1 1 d . . . C6 C 0.15135(13) 0.73180(12) 0.66259(6) 0.0176(2) Uani 1 1 d . . . H6 H 0.1382(16) 0.7519(16) 0.7174(9) 0.025(4) Uiso 1 1 d . . . C7 C 0.30083(12) 0.76168(11) 0.62241(6) 0.0142(2) Uani 1 1 d . . . H7 H 0.3707(16) 0.8308(14) 0.6477(8) 0.016(3) Uiso 1 1 d . . . C8 C 0.36677(12) 0.62047(11) 0.60225(6) 0.0133(2) Uani 1 1 d . . . C9 C 0.22028(12) 0.79933(11) 0.54018(6) 0.0138(2) Uani 1 1 d . . . H9 H 0.1505(16) 0.8810(15) 0.5446(8) 0.017 Uiso 1 1 d xyz . . C10 C 0.62760(12) 0.53130(11) 0.66982(6) 0.0158(2) Uani 1 1 d . . . C11 C 0.77201(13) 0.66365(12) 0.76689(6) 0.0183(2) Uani 1 1 d . . . H11A H 0.8638(17) 0.6170(16) 0.7480(8) 0.025(3) Uiso 1 1 d . . . H11B H 0.7384(17) 0.6127(16) 0.8129(9) 0.025(3) Uiso 1 1 d . . . C12 C 0.80041(14) 0.81596(13) 0.78386(7) 0.0232(3) Uani 1 1 d . . . H12A H 0.838(2) 0.8645(18) 0.7370(10) 0.037(3) Uiso 1 1 d . . . H12B H 0.879(2) 0.8262(17) 0.8289(10) 0.037(3) Uiso 1 1 d . . . H12C H 0.707(2) 0.8619(18) 0.7980(10) 0.037(3) Uiso 1 1 d . . . C13 C 0.27836(12) 0.92229(11) 0.42104(6) 0.0141(2) Uani 1 1 d . . . C14 C 0.27915(14) 1.07048(12) 0.45421(7) 0.0185(2) Uani 1 1 d . . . H14A H 0.2009(18) 1.0838(16) 0.4948(9) 0.029(2) Uiso 1 1 d . . . H14B H 0.2473(18) 1.1380(17) 0.4115(9) 0.029(2) Uiso 1 1 d . . . H14C H 0.3839(18) 1.0953(17) 0.4776(9) 0.029(2) Uiso 1 1 d . . . C15 C 0.11935(13) 0.88258(12) 0.38294(6) 0.0180(2) Uani 1 1 d . . . H15A H 0.1219(17) 0.7849(17) 0.3638(8) 0.026(2) Uiso 1 1 d . . . H15B H 0.0956(17) 0.9444(16) 0.3379(9) 0.026(2) Uiso 1 1 d . . . H15C H 0.0350(17) 0.8937(16) 0.4196(9) 0.026(2) Uiso 1 1 d . . . C16 C 0.40124(13) 0.90880(12) 0.36232(6) 0.0182(2) Uani 1 1 d . . . H16A H 0.5082(18) 0.9244(16) 0.3886(9) 0.026(2) Uiso 1 1 d . . . H16B H 0.3817(17) 0.9802(16) 0.3214(9) 0.026(2) Uiso 1 1 d . . . H16C H 0.3984(17) 0.8155(16) 0.3369(9) 0.026(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0130(3) 0.0144(4) 0.0142(3) 0.0034(3) 0.0017(3) 0.0021(3) O2 0.0153(4) 0.0194(4) 0.0196(4) -0.0014(3) -0.0047(3) 0.0025(3) O3 0.0221(4) 0.0205(4) 0.0310(5) -0.0007(3) -0.0070(3) 0.0071(3) N1 0.0164(4) 0.0137(4) 0.0177(4) 0.0004(3) 0.0008(3) 0.0026(3) C1 0.0149(5) 0.0148(5) 0.0144(5) 0.0015(4) 0.0023(4) 0.0001(4) C2 0.0175(5) 0.0144(5) 0.0153(5) 0.0006(4) 0.0010(4) -0.0019(4) C3 0.0134(5) 0.0151(5) 0.0136(5) 0.0013(4) 0.0014(4) -0.0010(4) C4 0.0122(5) 0.0168(5) 0.0144(5) 0.0007(4) 0.0000(4) -0.0001(4) C5 0.0144(5) 0.0215(5) 0.0185(5) 0.0030(4) 0.0039(4) 0.0023(4) C6 0.0173(5) 0.0202(5) 0.0155(5) 0.0012(4) 0.0035(4) 0.0038(4) C7 0.0141(5) 0.0154(5) 0.0129(5) -0.0004(4) 0.0004(4) 0.0012(4) C8 0.0133(5) 0.0142(5) 0.0123(4) 0.0015(4) 0.0018(4) -0.0003(4) C9 0.0131(5) 0.0148(5) 0.0136(5) -0.0003(4) 0.0014(4) 0.0014(4) C10 0.0147(5) 0.0168(5) 0.0160(5) 0.0031(4) 0.0021(4) 0.0011(4) C11 0.0152(5) 0.0239(6) 0.0154(5) 0.0023(4) -0.0024(4) 0.0011(4) C12 0.0214(6) 0.0256(6) 0.0215(6) -0.0052(5) -0.0054(4) 0.0052(5) C13 0.0144(5) 0.0133(5) 0.0142(5) 0.0027(4) -0.0012(4) 0.0010(4) C14 0.0213(5) 0.0132(5) 0.0205(5) -0.0001(4) -0.0015(4) 0.0014(4) C15 0.0158(5) 0.0202(5) 0.0174(5) 0.0014(4) -0.0026(4) -0.0005(4) C16 0.0185(5) 0.0189(5) 0.0172(5) 0.0043(4) 0.0017(4) 0.0014(4) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # 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 O1 C9 1.4185(13) . ? O1 C13 1.4640(12) . ? O2 C10 1.3488(14) . ? O2 C11 1.4531(13) . ? O3 C10 1.2135(14) . ? N1 C2 1.3706(14) . ? N1 C1 1.3881(14) . ? N1 H1 0.893(16) . ? C1 C8 1.3788(15) . ? C1 C10 1.4538(15) . ? C2 C3 1.3736(16) . ? C2 H2 0.965(15) . ? C3 C8 1.4093(15) . ? C3 C4 1.5132(15) . ? C4 C5 1.5355(15) . ? C4 C9 1.5782(15) . ? C4 H4 0.990(14) . ? C5 C6 1.3332(17) . ? C5 H5 0.984(15) . ? C6 C7 1.5377(15) . ? C6 H6 0.977(14) . ? C7 C8 1.5156(15) . ? C7 C9 1.5699(15) . ? C7 H7 0.975(14) . ? C9 H9 0.993(14) . ? C11 C12 1.5014(18) . ? C11 H11A 0.987(15) . ? C11 H11B 0.990(15) . ? C12 H12A 1.006(17) . ? C12 H12B 0.996(17) . ? C12 H12C 0.964(17) . ? C13 C16 1.5251(15) . ? C13 C15 1.5264(15) . ? C13 C14 1.5266(15) . ? C14 H14A 1.016(16) . ? C14 H14B 1.000(16) . ? C14 H14C 0.992(16) . ? C15 H15A 0.991(16) . ? C15 H15B 0.984(15) . ? C15 H15C 1.005(15) . ? C16 H16A 1.010(15) . ? C16 H16B 0.986(16) . ? C16 H16C 0.992(15) . ? 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 C9 O1 C13 116.06(8) . . ? C10 O2 C11 115.72(8) . . ? C2 N1 C1 109.67(9) . . ? C2 N1 H1 125.2(10) . . ? C1 N1 H1 123.5(10) . . ? C8 C1 N1 106.96(9) . . ? C8 C1 C10 133.48(10) . . ? N1 C1 C10 119.54(9) . . ? N1 C2 C3 107.57(9) . . ? N1 C2 H2 119.1(9) . . ? C3 C2 H2 133.3(9) . . ? C2 C3 C8 108.02(9) . . ? C2 C3 C4 144.88(10) . . ? C8 C3 C4 107.07(9) . . ? C3 C4 C5 106.56(8) . . ? C3 C4 C9 98.26(8) . . ? C5 C4 C9 96.72(8) . . ? C3 C4 H4 118.8(8) . . ? C5 C4 H4 116.3(8) . . ? C9 C4 H4 116.7(8) . . ? C6 C5 C4 108.20(10) . . ? C6 C5 H5 127.5(9) . . ? C4 C5 H5 124.2(9) . . ? C5 C6 C7 108.40(10) . . ? C5 C6 H6 127.5(9) . . ? C7 C6 H6 124.0(9) . . ? C8 C7 C6 106.31(9) . . ? C8 C7 C9 98.49(8) . . ? C6 C7 C9 96.63(8) . . ? C8 C7 H7 118.3(8) . . ? C6 C7 H7 116.1(8) . . ? C9 C7 H7 117.6(8) . . ? C1 C8 C3 107.78(10) . . ? C1 C8 C7 145.13(10) . . ? C3 C8 C7 107.06(9) . . ? O1 C9 C7 113.34(8) . . ? O1 C9 C4 116.04(8) . . ? C7 C9 C4 93.77(8) . . ? O1 C9 H9 111.2(8) . . ? C7 C9 H9 110.1(8) . . ? C4 C9 H9 111.2(8) . . ? O3 C10 O2 123.77(10) . . ? O3 C10 C1 124.61(10) . . ? O2 C10 C1 111.62(9) . . ? O2 C11 C12 107.18(9) . . ? O2 C11 H11A 109.1(9) . . ? C12 C11 H11A 112.2(9) . . ? O2 C11 H11B 106.7(9) . . ? C12 C11 H11B 112.0(9) . . ? H11A C11 H11B 109.4(12) . . ? C11 C12 H12A 110.5(10) . . ? C11 C12 H12B 109.8(10) . . ? H12A C12 H12B 109.4(14) . . ? C11 C12 H12C 111.3(10) . . ? H12A C12 H12C 108.7(14) . . ? H12B C12 H12C 107.1(14) . . ? O1 C13 C16 104.30(8) . . ? O1 C13 C15 110.26(8) . . ? C16 C13 C15 110.22(9) . . ? O1 C13 C14 110.15(9) . . ? C16 C13 C14 109.98(9) . . ? C15 C13 C14 111.69(9) . . ? C13 C14 H14A 112.9(9) . . ? C13 C14 H14B 109.4(9) . . ? H14A C14 H14B 105.1(12) . . ? C13 C14 H14C 110.6(9) . . ? H14A C14 H14C 109.1(12) . . ? H14B C14 H14C 109.6(13) . . ? C13 C15 H15A 109.6(9) . . ? C13 C15 H15B 108.5(9) . . ? H15A C15 H15B 108.3(12) . . ? C13 C15 H15C 112.2(8) . . ? H15A C15 H15C 110.1(12) . . ? H15B C15 H15C 108.2(12) . . ? C13 C16 H16A 110.6(8) . . ? C13 C16 H16B 108.9(9) . . ? H16A C16 H16B 108.6(12) . . ? C13 C16 H16C 111.8(9) . . ? H16A C16 H16C 108.8(12) . . ? H16B C16 H16C 108.1(12) . . ? 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 C2 N1 C1 C8 0.19(11) . . . . ? C2 N1 C1 C10 178.80(9) . . . . ? C1 N1 C2 C3 -0.50(12) . . . . ? N1 C2 C3 C8 0.62(12) . . . . ? N1 C2 C3 C4 -176.87(14) . . . . ? C2 C3 C4 C5 113.36(16) . . . . ? C8 C3 C4 C5 -64.14(11) . . . . ? C2 C3 C4 C9 -147.05(15) . . . . ? C8 C3 C4 C9 35.45(10) . . . . ? C3 C4 C5 C6 65.40(12) . . . . ? C9 C4 C5 C6 -35.32(11) . . . . ? C4 C5 C6 C7 -0.25(12) . . . . ? C5 C6 C7 C8 -64.96(11) . . . . ? C5 C6 C7 C9 35.93(11) . . . . ? N1 C1 C8 C3 0.20(11) . . . . ? C10 C1 C8 C3 -178.14(11) . . . . ? N1 C1 C8 C7 177.57(14) . . . . ? C10 C1 C8 C7 -0.8(2) . . . . ? C2 C3 C8 C1 -0.51(12) . . . . ? C4 C3 C8 C1 177.98(8) . . . . ? C2 C3 C8 C7 -178.93(8) . . . . ? C4 C3 C8 C7 -0.44(11) . . . . ? C6 C7 C8 C1 -112.84(16) . . . . ? C9 C7 C8 C1 147.65(15) . . . . ? C6 C7 C8 C3 64.54(10) . . . . ? C9 C7 C8 C3 -34.97(10) . . . . ? C13 O1 C9 C7 -149.31(8) . . . . ? C13 O1 C9 C4 103.80(10) . . . . ? C8 C7 C9 O1 -66.87(10) . . . . ? C6 C7 C9 O1 -174.52(8) . . . . ? C8 C7 C9 C4 53.63(9) . . . . ? C6 C7 C9 C4 -54.02(8) . . . . ? C3 C4 C9 O1 64.43(10) . . . . ? C5 C4 C9 O1 172.31(8) . . . . ? C3 C4 C9 C7 -53.87(8) . . . . ? C5 C4 C9 C7 54.01(9) . . . . ? C11 O2 C10 O3 -6.82(15) . . . . ? C11 O2 C10 C1 173.29(8) . . . . ? C8 C1 C10 O3 175.89(11) . . . . ? N1 C1 C10 O3 -2.29(16) . . . . ? C8 C1 C10 O2 -4.22(17) . . . . ? N1 C1 C10 O2 177.60(9) . . . . ? C10 O2 C11 C12 163.72(9) . . . . ? C9 O1 C13 C16 -171.76(8) . . . . ? C9 O1 C13 C15 -53.46(11) . . . . ? C9 O1 C13 C14 70.26(11) . . . . ? #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data__2OHBCHDPyrrole _database_code_depnum_ccdc_archive 'CCDC 887834' #TrackingRef '12001_web_deposit_cif_file_0_HidemitsuUno_1340112602.OHBCHDPyrrole.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C12 H13 N O3' _chemical_formula_moiety 'C12 H13 N O3' _chemical_formula_weight 219.24 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 10.023(2) _cell_length_b 12.899(3) _cell_length_c 9.2210(18) _cell_angle_alpha 90.0000 _cell_angle_beta 115.590(3) _cell_angle_gamma 90.0000 _cell_volume 1075.2(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2879 _cell_measurement_theta_min 3.16 _cell_measurement_theta_max 27.48 _cell_measurement_temperature 150(2) #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.150 _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464.00 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.887 _exptl_absorpt_correction_T_max 0.985 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 150(2) _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku Mercury-8' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 14.6199 _diffrn_reflns_number 12699 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Hydrogen atoms are placed at the calculated position and the bond lengths are refined by AFIX *8 commands. ; _reflns_number_total 2450 _reflns_number_gt 2181 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1699 _refine_ls_wR_factor_gt 0.1602 _refine_ls_goodness_of_fit_ref 1.177 _refine_ls_restrained_S_all 1.177 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_hydrogen_treatment refxyz _refine_ls_number_reflns 2450 _refine_ls_number_parameters 166 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0920P)^2^+0.4198P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_diff_density_max 0.320 _refine_diff_density_min -0.270 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.023(6) _iucr_refine_instructions_details ; TITL _2OHBCHDPyrrole CELL 0.71070 10.02320 12.89870 9.22100 90.000 115.590 90.000 ZERR 4 0.00210 0.00240 0.00180 0.000 0.002 0.000 LATT 1 SYMM -X, .50+Y, .50-Z SFAC C H N O UNIT 48 52 4 12 SHEL 99999.000000 0.000000 L.S. 5 FMAP 2 PLAN -25 WPDB -2 HTAB BOND $H CONF TEMP -123.1 ACTA SIZE 0.350 0.300 0.150 WGHT 0.092000 0.419800 EXTI 0.022506 FVAR 2.88173 O1 4 0.397846 0.744890 0.212042 11.00000 0.02830 0.02473 = 0.03071 0.00217 0.00619 -0.00521 AFIX 148 H1 2 0.444416 0.688520 0.276110 11.00000 -1.50000 AFIX 0 O2 4 0.235381 0.491144 0.493506 11.00000 0.03925 0.03322 = 0.02821 0.00172 0.01707 0.00030 O3 4 0.393040 0.358477 0.526472 11.00000 0.03623 0.03768 = 0.03318 0.01161 0.00989 0.00529 N1 3 0.396664 0.407349 0.232122 11.00000 0.02714 0.02422 = 0.03226 0.00458 0.01274 0.00445 AFIX 48 H1A 2 0.443541 0.350394 0.272149 11.00000 -1.20000 AFIX 0 C1 1 0.318586 0.464468 0.297129 11.00000 0.02343 0.02390 = 0.02666 -0.00013 0.00988 -0.00077 C2 1 0.388935 0.453858 0.096030 11.00000 0.02799 0.02708 = 0.02993 0.00133 0.01491 0.00198 AFIX 48 H2 2 0.432714 0.429601 0.029574 11.00000 -1.20000 AFIX 0 C3 1 0.305816 0.542579 0.072840 11.00000 0.02653 0.02313 = 0.02573 0.00057 0.01187 -0.00155 C4 1 0.242727 0.637141 -0.033607 11.00000 0.02795 0.02508 = 0.02360 0.00085 0.01094 -0.00065 AFIX 18 H4 2 0.289712 0.657884 -0.107263 11.00000 -1.20000 AFIX 0 C5 1 0.074491 0.625069 -0.109491 11.00000 0.02875 0.02641 = 0.02635 0.00075 0.00678 0.00158 AFIX 48 H5 2 0.010524 0.615997 -0.223977 11.00000 -1.20000 AFIX 0 C6 1 0.030193 0.629044 0.007205 11.00000 0.02441 0.02414 = 0.03237 0.00123 0.00856 0.00201 AFIX 48 H6 2 -0.069627 0.622802 -0.006727 11.00000 -1.20000 AFIX 0 C7 1 0.166083 0.645308 0.167668 11.00000 0.02650 0.02286 = 0.02636 -0.00089 0.01087 0.00016 AFIX 18 H7 2 0.148640 0.672692 0.259494 11.00000 -1.20000 AFIX 0 C8 1 0.260853 0.548609 0.197978 11.00000 0.02294 0.02268 = 0.02374 0.00037 0.00910 -0.00219 C9 1 0.254538 0.716340 0.101255 11.00000 0.02459 0.02229 = 0.02756 0.00083 0.00813 -0.00044 AFIX 18 H9 2 0.195568 0.779676 0.051031 11.00000 -1.20000 AFIX 0 C10 1 0.321112 0.431550 0.448645 11.00000 0.02617 0.02782 = 0.02500 0.00027 0.00737 -0.00416 C11 1 0.239597 0.467566 0.648809 11.00000 0.04595 0.04625 = 0.02761 -0.00399 0.01833 -0.00976 AFIX 28 H11A 2 0.212045 0.528680 0.690295 11.00000 -1.20000 H11B 2 0.339523 0.449085 0.722826 11.00000 -1.20000 AFIX 0 C12 1 0.136970 0.379993 0.639621 11.00000 0.05195 0.06010 = 0.04507 0.00085 0.02499 -0.01785 AFIX 138 H12A 2 0.169258 0.315099 0.603399 11.00000 -1.50000 H12B 2 0.033348 0.398126 0.560658 11.00000 -1.50000 H12C 2 0.139777 0.368278 0.748671 11.00000 -1.50000 HKLF 4 REM _2OHBCHDPyrrole REM R1 = 0.0578 for 2181 Fo > 4sig(Fo) and 0.0626 for all 2450 data REM 166 parameters refined using 0 restraints END WGHT 0.0923 0.4189 REM Highest difference peak 0.316, deepest hole -0.275, 1-sigma level 0.059 Q1 1 0.2383 0.6791 0.0231 11.00000 0.05 0.28 Q2 1 0.2148 0.5842 0.2032 11.00000 0.05 0.21 Q3 1 0.1425 0.5655 0.6429 11.00000 0.05 0.20 Q4 1 0.4446 0.5396 0.1584 11.00000 0.05 0.20 Q5 1 0.2077 0.6927 0.1245 11.00000 0.05 0.20 Q6 1 0.1174 0.5759 0.0948 11.00000 0.05 0.19 Q7 1 0.4198 0.8630 0.2333 11.00000 0.05 0.19 Q8 1 0.3330 0.6116 -0.2183 11.00000 0.05 0.18 Q9 1 0.3551 0.7619 0.3223 11.00000 0.05 0.18 Q10 1 0.3206 0.2951 0.5779 11.00000 0.05 0.18 Q11 1 0.3822 0.5471 0.3106 11.00000 0.05 0.18 Q12 1 0.3273 0.8139 0.2325 11.00000 0.05 0.17 Q13 1 0.2702 0.5591 0.7074 11.00000 0.05 0.17 Q14 1 0.2356 0.5482 0.3215 11.00000 0.05 0.17 Q15 1 0.2375 0.6443 -0.1723 11.00000 0.05 0.17 Q16 1 0.4025 0.8313 0.1364 11.00000 0.05 0.17 Q17 1 0.3221 0.4919 0.7556 11.00000 0.05 0.16 Q18 1 0.0874 0.6026 -0.2346 11.00000 0.05 0.16 Q19 1 0.3311 0.2971 0.3856 11.00000 0.05 0.16 Q20 1 0.4387 0.7534 0.0972 11.00000 0.05 0.16 Q21 1 0.3014 0.8749 0.1411 11.00000 0.05 0.16 Q22 1 0.2462 0.8708 0.1504 11.00000 0.05 0.16 Q23 1 0.3977 0.6083 0.0629 11.00000 0.05 0.15 Q24 1 0.1554 0.6250 0.6963 11.00000 0.05 0.15 Q25 1 0.4982 0.3670 0.0279 11.00000 0.05 0.15 ; 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.39785(12) 0.74489(9) 0.21204(13) 0.0302(3) Uani 1 1 d . . . H1 H 0.4444(16) 0.6885(16) 0.276(2) 0.045 Uiso 1 1 calc R . . O2 O 0.23538(13) 0.49114(9) 0.49351(14) 0.0327(3) Uani 1 1 d . . . O3 O 0.39304(14) 0.35848(10) 0.52647(15) 0.0375(3) Uani 1 1 d . . . N1 N 0.39666(15) 0.40735(11) 0.23212(16) 0.0279(3) Uani 1 1 d . . . H1A H 0.4435(12) 0.3504(15) 0.2721(11) 0.033 Uiso 1 1 calc R . . C1 C 0.31859(16) 0.46447(11) 0.29713(18) 0.0250(4) Uani 1 1 d . . . C2 C 0.38893(17) 0.45386(12) 0.09603(19) 0.0275(4) Uani 1 1 d . . . H2 H 0.4327(10) 0.4296(6) 0.0296(15) 0.033 Uiso 1 1 calc R . . C3 C 0.30582(17) 0.54258(11) 0.07284(17) 0.0249(3) Uani 1 1 d . . . C4 C 0.24273(17) 0.63714(12) -0.03361(18) 0.0256(3) Uani 1 1 d . . . H4 H 0.2897(10) 0.6579(4) -0.1073(15) 0.031 Uiso 1 1 calc R . . C5 C 0.07449(18) 0.62507(12) -0.10949(19) 0.0290(4) Uani 1 1 d . . . H5 H 0.0105(14) 0.6160(2) -0.224(3) 0.035 Uiso 1 1 calc R . . C6 C 0.03019(17) 0.62904(12) 0.00720(19) 0.0283(4) Uani 1 1 d . . . H6 H -0.070(2) 0.62280(18) -0.0067(4) 0.034 Uiso 1 1 calc R . . C7 C 0.16608(16) 0.64531(12) 0.16767(18) 0.0254(3) Uani 1 1 d . . . H7 H 0.1486(4) 0.6727(6) 0.2595(19) 0.031 Uiso 1 1 calc R . . C8 C 0.26085(16) 0.54861(11) 0.19798(17) 0.0235(3) Uani 1 1 d . . . C9 C 0.25454(16) 0.71634(12) 0.10125(18) 0.0259(3) Uani 1 1 d . . . H9 H 0.1956(12) 0.7797(13) 0.0510(11) 0.031 Uiso 1 1 calc R . . C10 C 0.32111(17) 0.43155(12) 0.44864(18) 0.0276(4) Uani 1 1 d . . . C11 C 0.2396(2) 0.46757(16) 0.6488(2) 0.0391(4) Uani 1 1 d . . . H11A H 0.2120(5) 0.5287(11) 0.6903(8) 0.047 Uiso 1 1 calc R . . H11B H 0.3395(18) 0.4491(4) 0.7228(14) 0.047 Uiso 1 1 calc R . . C12 C 0.1370(3) 0.37999(19) 0.6396(3) 0.0509(5) Uani 1 1 d . . . H12A H 0.1693(13) 0.3151(11) 0.603(2) 0.076 Uiso 1 1 calc R . . H12B H 0.0333(18) 0.3981(7) 0.561(2) 0.076 Uiso 1 1 calc R . . H12C H 0.1398(16) 0.3683(10) 0.7487(19) 0.076 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0283(6) 0.0247(6) 0.0307(6) 0.0022(4) 0.0062(5) -0.0052(4) O2 0.0393(6) 0.0332(6) 0.0282(6) 0.0017(4) 0.0171(5) 0.0003(5) O3 0.0362(7) 0.0377(7) 0.0332(6) 0.0116(5) 0.0099(5) 0.0053(5) N1 0.0271(7) 0.0242(7) 0.0323(7) 0.0046(5) 0.0127(5) 0.0044(5) C1 0.0234(7) 0.0239(7) 0.0267(7) -0.0001(5) 0.0099(6) -0.0008(5) C2 0.0280(7) 0.0271(8) 0.0299(8) 0.0013(6) 0.0149(6) 0.0020(6) C3 0.0265(7) 0.0231(7) 0.0257(7) 0.0006(5) 0.0119(6) -0.0015(5) C4 0.0280(7) 0.0251(7) 0.0236(7) 0.0009(5) 0.0109(6) -0.0007(5) C5 0.0287(7) 0.0264(8) 0.0264(7) 0.0007(5) 0.0068(6) 0.0016(6) C6 0.0244(7) 0.0241(7) 0.0324(8) 0.0012(5) 0.0086(6) 0.0020(5) C7 0.0265(7) 0.0229(7) 0.0264(7) -0.0009(5) 0.0109(6) 0.0002(5) C8 0.0229(7) 0.0227(7) 0.0237(7) 0.0004(5) 0.0091(5) -0.0022(5) C9 0.0246(7) 0.0223(7) 0.0276(7) 0.0008(5) 0.0081(6) -0.0004(5) C10 0.0262(7) 0.0278(8) 0.0250(7) 0.0003(5) 0.0074(6) -0.0042(6) C11 0.0459(10) 0.0462(10) 0.0276(8) -0.0040(7) 0.0183(7) -0.0098(8) C12 0.0520(12) 0.0601(13) 0.0451(11) 0.0008(9) 0.0250(9) -0.0178(10) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.4053(17) . ? O1 H1 0.9259 . ? O2 C10 1.344(2) . ? O2 C11 1.447(2) . ? O3 C10 1.215(2) . ? N1 C2 1.363(2) . ? N1 C1 1.386(2) . ? N1 H1A 0.8642 . ? C1 C8 1.375(2) . ? C1 C10 1.450(2) . ? C2 C3 1.377(2) . ? C2 H2 0.9478 . ? C3 C8 1.411(2) . ? C3 C4 1.521(2) . ? C4 C5 1.529(2) . ? C4 C9 1.574(2) . ? C4 H4 1.0154 . ? C5 C6 1.331(2) . ? C5 H5 0.9770 . ? C6 C7 1.532(2) . ? C6 H6 0.9555 . ? C7 C8 1.519(2) . ? C7 C9 1.571(2) . ? C7 H7 1.0001 . ? C9 H9 0.9974 . ? C11 C12 1.505(3) . ? C11 H11A 0.9671 . ? C11 H11B 0.9671 . ? C12 H12A 1.0051 . ? C12 H12B 1.0051 . ? C12 H12C 1.0051 . ? 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 C9 O1 H1 109.5 . . ? C10 O2 C11 115.79(14) . . ? C2 N1 C1 110.26(13) . . ? C2 N1 H1A 124.9 . . ? C1 N1 H1A 124.9 . . ? C8 C1 N1 106.62(13) . . ? C8 C1 C10 134.33(15) . . ? N1 C1 C10 118.89(14) . . ? N1 C2 C3 107.39(13) . . ? N1 C2 H2 126.3 . . ? C3 C2 H2 126.3 . . ? C2 C3 C8 107.73(13) . . ? C2 C3 C4 145.24(14) . . ? C8 C3 C4 107.03(12) . . ? C3 C4 C5 106.41(12) . . ? C3 C4 C9 98.17(11) . . ? C5 C4 C9 96.86(12) . . ? C3 C4 H4 117.3 . . ? C5 C4 H4 117.3 . . ? C9 C4 H4 117.3 . . ? C6 C5 C4 108.26(13) . . ? C6 C5 H5 125.9 . . ? C4 C5 H5 125.9 . . ? C5 C6 C7 108.56(13) . . ? C5 C6 H6 125.7 . . ? C7 C6 H6 125.7 . . ? C8 C7 C6 106.84(12) . . ? C8 C7 C9 97.89(11) . . ? C6 C7 C9 96.85(11) . . ? C8 C7 H7 117.3 . . ? C6 C7 H7 117.3 . . ? C9 C7 H7 117.3 . . ? C1 C8 C3 107.99(13) . . ? C1 C8 C7 145.13(14) . . ? C3 C8 C7 106.87(12) . . ? O1 C9 C7 116.17(12) . . ? O1 C9 C4 116.67(12) . . ? C7 C9 C4 93.84(11) . . ? O1 C9 H9 109.7 . . ? C7 C9 H9 109.7 . . ? C4 C9 H9 109.7 . . ? O3 C10 O2 123.84(15) . . ? O3 C10 C1 123.73(16) . . ? O2 C10 C1 112.43(13) . . ? O2 C11 C12 112.02(15) . . ? O2 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? O2 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 C2 N1 C1 C8 0.09(17) . . . . ? C2 N1 C1 C10 -176.04(13) . . . . ? C1 N1 C2 C3 0.42(18) . . . . ? N1 C2 C3 C8 -0.75(17) . . . . ? N1 C2 C3 C4 179.2(2) . . . . ? C2 C3 C4 C5 114.6(2) . . . . ? C8 C3 C4 C5 -65.41(15) . . . . ? C2 C3 C4 C9 -145.7(2) . . . . ? C8 C3 C4 C9 34.26(14) . . . . ? C3 C4 C5 C6 64.76(15) . . . . ? C9 C4 C5 C6 -35.88(15) . . . . ? C4 C5 C6 C7 0.67(16) . . . . ? C5 C6 C7 C8 -65.54(15) . . . . ? C5 C6 C7 C9 34.87(15) . . . . ? N1 C1 C8 C3 -0.55(16) . . . . ? C10 C1 C8 C3 174.71(16) . . . . ? N1 C1 C8 C7 178.34(19) . . . . ? C10 C1 C8 C7 -6.4(3) . . . . ? C2 C3 C8 C1 0.81(17) . . . . ? C4 C3 C8 C1 -179.15(12) . . . . ? C2 C3 C8 C7 -178.52(12) . . . . ? C4 C3 C8 C7 1.52(15) . . . . ? C6 C7 C8 C1 -116.0(2) . . . . ? C9 C7 C8 C1 144.4(2) . . . . ? C6 C7 C8 C3 62.94(15) . . . . ? C9 C7 C8 C3 -36.72(14) . . . . ? C8 C7 C9 O1 -67.46(15) . . . . ? C6 C7 C9 O1 -175.60(13) . . . . ? C8 C7 C9 C4 54.83(12) . . . . ? C6 C7 C9 C4 -53.30(12) . . . . ? C3 C4 C9 O1 67.94(15) . . . . ? C5 C4 C9 O1 175.68(12) . . . . ? C3 C4 C9 C7 -53.96(12) . . . . ? C5 C4 C9 C7 53.78(12) . . . . ? C11 O2 C10 O3 3.7(2) . . . . ? C11 O2 C10 C1 -176.05(13) . . . . ? C8 C1 C10 O3 -171.74(16) . . . . ? N1 C1 C10 O3 3.1(2) . . . . ? C8 C1 C10 O2 8.1(2) . . . . ? N1 C1 C10 O2 -177.13(13) . . . . ? C10 O2 C11 C12 -83.3(2) . . . . ? #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1 O3 . . 3_666 2.7602(16) 0.926 1.943 146.2 no N1 H1A O1 . . 2_645 2.8253(19) 0.864 2.049 149.0 no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data_20120128_2 _database_code_depnum_ccdc_archive 'CCDC 887837' #TrackingRef '12002_web_deposit_cif_file_0_HidemitsuUno_1340113272.Diazafluvalene.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C38 H26 N2 O4' _chemical_formula_moiety 'C38 H26 N2 O4' _chemical_formula_weight 574.63 _chemical_melting_point ? _chemical_absolute_configuration unk #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 3.86191(15) _cell_length_b 21.4583(9) _cell_length_c 16.3912(7) _cell_angle_alpha 90.0000 _cell_angle_beta 93.240(7) _cell_angle_gamma 90.0000 _cell_volume 1356.17(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 8786 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 68.25 _cell_measurement_temperature 100 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.270 _exptl_crystal_size_mid 0.040 _exptl_crystal_size_min 0.010 _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600.00 _exptl_absorpt_coefficient_mu 0.738 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.671 _exptl_absorpt_correction_T_max 0.993 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 100 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 15809 _diffrn_reflns_av_R_equivalents 0.0914 _diffrn_reflns_theta_max 68.25 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. This compound is obtained as very thin platelet crystals, which are tend to pile up. The crystal measured is also accompanied some very thin tiny platelet crystals. Some of diffractions from these crystals cannot be separated. Therefore, Rmerge values are rather high and the positive large electron density is observed. ; _reflns_number_total 4905 _reflns_number_gt 3931 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_all 0.1051 _refine_ls_R_factor_gt 0.0948 _refine_ls_wR_factor_ref 0.2327 _refine_ls_wR_factor_gt 0.2188 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 4904 _refine_ls_number_parameters 397 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1657P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_diff_density_max 1.040 _refine_diff_density_min -0.310 _refine_ls_extinction_method none 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0095(9) 0.08040(15) 0.44355(19) 0.0368(8) Uani 1.0 2 d . . . O2 O 0.2497(8) 0.13770(14) 0.54625(18) 0.0282(7) Uani 1.0 2 d . . . O3 O 1.2881(9) 0.49050(15) 0.31261(19) 0.0332(8) Uani 1.0 2 d . . . O4 O 1.0187(9) 0.43430(15) 0.21286(18) 0.0305(8) Uani 1.0 2 d . . . N1 N 0.4843(10) 0.22112(16) 0.4406(3) 0.0277(9) Uani 1.0 2 d . . . N2 N 0.7869(10) 0.35298(16) 0.3197(2) 0.0270(9) Uani 1.0 2 d . . . C1 C 0.5379(12) 0.2606(2) 0.3748(3) 0.0264(9) Uani 1.0 2 d . . . C2 C 0.2974(11) 0.17418(19) 0.4126(3) 0.0262(9) Uani 1.0 2 d . . . C3 C 0.2122(11) 0.17751(19) 0.3253(3) 0.0262(9) Uani 1.0 2 d . . . C4 C 0.0291(11) 0.1401(2) 0.2703(3) 0.0264(9) Uani 1.0 2 d . . . C5 C -0.0107(11) 0.1596(2) 0.1871(3) 0.0280(10) Uani 1.0 2 d . . . C6 C -0.1887(11) 0.1224(2) 0.1281(3) 0.0275(10) Uani 1.0 2 d . . . C7 C -0.2421(11) 0.14162(19) 0.0461(3) 0.0243(10) Uani 1.0 2 d . . . C8 C -0.4215(12) 0.1054(3) -0.0145(4) 0.0349(12) Uani 1.0 2 d . . . C9 C -0.4694(13) 0.1252(3) -0.0921(3) 0.0364(11) Uani 1.0 2 d . . . C10 C -0.3409(13) 0.1842(3) -0.1150(3) 0.0359(12) Uani 1.0 2 d . . . C11 C -0.1694(12) 0.2222(2) -0.0589(3) 0.0302(10) Uani 1.0 2 d . . . C12 C -0.1119(11) 0.2022(2) 0.0233(3) 0.0275(10) Uani 1.0 2 d . . . C13 C 0.0688(12) 0.2380(2) 0.0824(3) 0.0279(10) Uani 1.0 2 d . . . C14 C 0.1238(11) 0.21901(19) 0.1638(3) 0.0244(9) Uani 1.0 2 d . . . C15 C 0.3188(11) 0.2566(2) 0.2221(3) 0.0267(10) Uani 1.0 2 d . . . C16 C 0.3628(12) 0.2357(2) 0.3004(3) 0.0253(9) Uani 1.0 2 d . . . C17 C 0.7272(11) 0.3136(2) 0.3860(3) 0.0247(9) Uani 1.0 2 d . . . C18 C 0.9774(12) 0.3998(2) 0.3473(3) 0.0276(10) Uani 1.0 2 d . . . C19 C 1.0536(11) 0.39780(19) 0.4346(3) 0.0257(9) Uani 1.0 2 d . . . C20 C 1.2223(11) 0.4362(2) 0.4897(3) 0.0271(10) Uani 1.0 2 d . . . C21 C 1.2575(11) 0.41740(18) 0.5738(3) 0.0265(10) Uani 1.0 2 d . . . C22 C 1.4234(12) 0.4557(2) 0.6322(3) 0.0278(10) Uani 1.0 2 d . . . C23 C 1.4736(11) 0.43667(19) 0.7133(3) 0.0234(9) Uani 1.0 2 d . . . C24 C 1.6421(12) 0.4748(3) 0.7756(3) 0.0309(11) Uani 1.0 2 d . . . C25 C 1.6910(12) 0.4550(3) 0.8545(3) 0.0329(11) Uani 1.0 2 d . . . C26 C 1.5781(12) 0.3947(3) 0.8772(3) 0.0315(11) Uani 1.0 2 d . . . C27 C 1.4087(13) 0.3568(3) 0.8202(3) 0.0328(11) Uani 1.0 2 d . . . C28 C 1.3522(12) 0.3761(2) 0.7376(3) 0.0278(10) Uani 1.0 2 d . . . C29 C 1.1789(12) 0.3383(2) 0.6790(3) 0.0276(10) Uani 1.0 2 d . . . C30 C 1.1231(11) 0.3579(2) 0.5978(3) 0.0267(10) Uani 1.0 2 d . . . C31 C 0.9431(11) 0.3194(2) 0.5389(3) 0.0270(10) Uani 1.0 2 d . . . C32 C 0.9041(11) 0.33982(19) 0.4603(3) 0.0266(9) Uani 1.0 2 d . . . C33 C 0.1705(11) 0.1247(2) 0.4672(3) 0.0281(10) Uani 1.0 2 d . . . C34 C 0.1115(12) 0.0947(2) 0.6042(3) 0.0316(10) Uani 1.0 2 d . . . C35 C 0.1760(14) 0.1239(3) 0.6874(3) 0.0420(12) Uani 1.0 2 d . . . C36 C 1.1108(11) 0.44750(19) 0.2916(3) 0.0270(10) Uani 1.0 2 d . . . C37 C 1.1653(13) 0.4743(3) 0.1523(3) 0.0346(11) Uani 1.0 2 d . . . C38 C 1.0893(15) 0.4436(3) 0.0714(3) 0.0480(14) Uani 1.0 2 d . . . H4 H -0.0692 0.1020 0.2874 0.0317 Uiso 1.0 2 calc R . . H6 H -0.2758 0.0831 0.1439 0.0330 Uiso 1.0 2 calc R . . H8 H -0.5110 0.0659 0.0001 0.0419 Uiso 1.0 2 calc R . . H9 H -0.5894 0.0996 -0.1317 0.0437 Uiso 1.0 2 calc R . . H10 H -0.3743 0.1976 -0.1701 0.0431 Uiso 1.0 2 calc R . . H11 H -0.0891 0.2620 -0.0751 0.0362 Uiso 1.0 2 calc R . . H13 H 0.1591 0.2771 0.0667 0.0335 Uiso 1.0 2 calc R . . H15 H 0.4152 0.2953 0.2065 0.0321 Uiso 1.0 2 calc R . . H20 H 1.3151 0.4748 0.4728 0.0325 Uiso 1.0 2 calc R . . H22 H 1.5038 0.4956 0.6166 0.0333 Uiso 1.0 2 calc R . . H24 H 1.7222 0.5150 0.7614 0.0371 Uiso 1.0 2 calc R . . H25 H 1.8008 0.4816 0.8944 0.0395 Uiso 1.0 2 calc R . . H26 H 1.6198 0.3805 0.9318 0.0378 Uiso 1.0 2 calc R . . H27 H 1.3281 0.3171 0.8363 0.0393 Uiso 1.0 2 calc R . . H29 H 1.0974 0.2986 0.6946 0.0331 Uiso 1.0 2 calc R . . H31 H 0.8519 0.2802 0.5541 0.0324 Uiso 1.0 2 calc R . . H34A H 0.2301 0.0539 0.6019 0.0379 Uiso 1.0 2 calc R . . H34B H -0.1400 0.0883 0.5921 0.0379 Uiso 1.0 2 calc R . . H35A H 0.4264 0.1276 0.6999 0.0629 Uiso 1.0 2 calc R . . H35B H 0.0737 0.0978 0.7287 0.0629 Uiso 1.0 2 calc R . . H35C H 0.0700 0.1654 0.6876 0.0629 Uiso 1.0 2 calc R . . H37A H 1.4187 0.4788 0.1635 0.0415 Uiso 1.0 2 calc R . . H37B H 1.0581 0.5162 0.1530 0.0415 Uiso 1.0 2 calc R . . H38A H 1.2105 0.4035 0.0703 0.0719 Uiso 1.0 2 calc R . . H38B H 1.1687 0.4704 0.0278 0.0719 Uiso 1.0 2 calc R . . H38C H 0.8390 0.4367 0.0630 0.0719 Uiso 1.0 2 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.046(2) 0.0344(19) 0.0297(18) -0.0069(16) -0.0019(15) 0.0015(14) O2 0.0246(15) 0.0307(17) 0.0290(17) -0.0046(14) -0.0004(13) 0.0035(13) O3 0.0408(19) 0.0317(17) 0.0269(16) -0.0059(15) 0.0014(14) -0.0017(13) O4 0.0354(17) 0.0327(17) 0.0234(17) -0.0061(14) 0.0006(13) 0.0026(13) N1 0.034(3) 0.0232(19) 0.026(2) 0.0002(16) 0.0024(16) -0.0010(14) N2 0.030(2) 0.0268(19) 0.0239(19) 0.0022(16) 0.0041(15) -0.0006(14) C1 0.027(2) 0.028(2) 0.025(3) 0.0047(18) 0.0014(17) -0.0004(16) C2 0.027(2) 0.024(3) 0.028(3) 0.0015(18) 0.0045(17) 0.0006(17) C3 0.023(2) 0.024(3) 0.032(3) 0.0022(17) 0.0037(18) -0.0001(18) C4 0.029(3) 0.032(3) 0.019(2) 0.0016(19) 0.0016(17) -0.0006(17) C5 0.024(3) 0.032(3) 0.028(3) 0.0043(18) 0.0062(18) 0.0021(18) C6 0.028(3) 0.027(3) 0.027(3) -0.0017(18) 0.0004(18) -0.0019(18) C7 0.023(2) 0.020(2) 0.030(3) 0.0007(18) 0.0061(17) -0.0014(17) C8 0.035(3) 0.033(3) 0.036(3) 0.000(2) -0.004(2) -0.009(2) C9 0.035(3) 0.043(3) 0.032(3) 0.001(3) 0.004(2) -0.005(2) C10 0.043(3) 0.036(3) 0.029(3) -0.001(3) -0.000(2) -0.0020(19) C11 0.037(3) 0.025(3) 0.029(3) -0.0008(19) -0.0022(19) 0.0005(18) C12 0.022(3) 0.031(3) 0.029(3) 0.0004(17) -0.0021(18) -0.0022(17) C13 0.029(3) 0.029(3) 0.026(3) 0.0009(19) 0.0047(18) -0.0003(18) C14 0.018(2) 0.026(2) 0.029(3) 0.0014(17) 0.0003(16) -0.0017(17) C15 0.027(2) 0.027(2) 0.027(3) 0.0009(17) 0.0044(18) -0.0013(17) C16 0.027(2) 0.023(2) 0.026(3) 0.0033(17) 0.0023(17) -0.0047(16) C17 0.022(2) 0.028(3) 0.025(3) 0.0050(16) 0.0060(17) 0.0009(16) C18 0.030(3) 0.032(3) 0.021(2) -0.0019(19) 0.0043(17) -0.0028(18) C19 0.024(2) 0.025(3) 0.027(3) 0.0034(18) -0.0008(17) 0.0020(17) C20 0.025(2) 0.022(2) 0.034(3) -0.0036(17) 0.0029(18) -0.0013(18) C21 0.027(3) 0.026(3) 0.027(3) 0.0018(18) -0.0002(18) -0.0033(17) C22 0.030(3) 0.028(3) 0.025(3) -0.0029(18) -0.0000(18) -0.0017(17) C23 0.021(2) 0.017(2) 0.032(3) -0.0011(17) 0.0001(17) -0.0003(17) C24 0.028(3) 0.042(3) 0.023(3) 0.011(2) 0.0043(18) 0.0041(19) C25 0.028(3) 0.042(3) 0.028(3) 0.002(2) -0.0029(18) -0.0050(19) C26 0.029(3) 0.038(3) 0.028(3) -0.005(2) 0.0027(19) 0.0007(19) C27 0.042(3) 0.034(3) 0.023(3) 0.006(2) 0.0089(19) -0.0007(18) C28 0.030(3) 0.031(3) 0.022(3) 0.0016(19) 0.0039(18) -0.0003(17) C29 0.030(3) 0.027(3) 0.026(3) -0.0001(18) 0.0030(17) -0.0005(18) C30 0.023(2) 0.034(3) 0.024(3) 0.0029(18) 0.0055(17) -0.0036(18) C31 0.027(3) 0.026(3) 0.029(3) 0.0024(17) 0.0036(18) 0.0025(18) C32 0.025(2) 0.025(3) 0.029(3) 0.0025(18) 0.0020(17) 0.0006(18) C33 0.023(2) 0.030(3) 0.032(3) 0.0014(19) 0.0036(18) 0.0043(19) C34 0.032(3) 0.038(3) 0.025(3) -0.0039(19) -0.0025(19) 0.0040(18) C35 0.040(3) 0.056(4) 0.029(3) -0.011(3) 0.002(2) 0.001(3) C36 0.028(3) 0.023(3) 0.030(3) 0.0028(18) 0.0042(18) -0.0001(18) C37 0.038(3) 0.040(3) 0.027(3) -0.006(2) 0.008(2) 0.0040(19) C38 0.052(4) 0.065(4) 0.027(3) -0.015(3) 0.005(3) 0.001(3) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O1 C33 1.189(6) yes . . O2 C33 1.343(6) yes . . O2 C34 1.448(6) yes . . O3 C36 1.188(6) yes . . O4 C36 1.350(6) yes . . O4 C37 1.451(6) yes . . N1 C1 1.397(6) yes . . N1 C2 1.307(6) yes . . N2 C17 1.405(6) yes . . N2 C18 1.310(6) yes . . C1 C16 1.461(6) yes . . C1 C17 1.358(7) yes . . C2 C3 1.451(6) yes . . C2 C33 1.490(6) yes . . C3 C4 1.373(6) yes . . C3 C16 1.446(6) yes . . C4 C5 1.426(7) yes . . C5 C6 1.403(6) yes . . C5 C14 1.438(6) yes . . C6 C7 1.410(7) yes . . C7 C8 1.411(7) yes . . C7 C12 1.450(6) yes . . C8 C9 1.345(8) yes . . C9 C10 1.418(8) yes . . C10 C11 1.371(7) yes . . C11 C12 1.420(7) yes . . C12 C13 1.393(7) yes . . C13 C14 1.399(7) yes . . C14 C15 1.433(6) yes . . C15 C16 1.361(6) yes . . C17 C32 1.474(6) yes . . C18 C19 1.445(6) yes . . C18 C36 1.483(7) yes . . C19 C20 1.362(6) yes . . C19 C32 1.445(6) yes . . C20 C21 1.435(7) yes . . C21 C22 1.391(6) yes . . C21 C30 1.441(6) yes . . C22 C23 1.394(7) yes . . C23 C24 1.435(7) yes . . C23 C28 1.445(6) yes . . C24 C25 1.364(7) yes . . C25 C26 1.423(7) yes . . C26 C27 1.376(7) yes . . C27 C28 1.421(6) yes . . C28 C29 1.398(6) yes . . C29 C30 1.401(6) yes . . C30 C31 1.423(6) yes . . C31 C32 1.361(7) yes . . C34 C35 1.508(7) yes . . C37 C38 1.496(7) yes . . C4 H4 0.950 no . . C6 H6 0.950 no . . C8 H8 0.950 no . . C9 H9 0.950 no . . C10 H10 0.950 no . . C11 H11 0.950 no . . C13 H13 0.950 no . . C15 H15 0.950 no . . C20 H20 0.950 no . . C22 H22 0.950 no . . C24 H24 0.950 no . . C25 H25 0.950 no . . C26 H26 0.950 no . . C27 H27 0.950 no . . C29 H29 0.950 no . . C31 H31 0.950 no . . C34 H34A 0.990 no . . C34 H34B 0.990 no . . C35 H35A 0.980 no . . C35 H35B 0.980 no . . C35 H35C 0.980 no . . C37 H37A 0.990 no . . C37 H37B 0.990 no . . C38 H38A 0.980 no . . C38 H38B 0.980 no . . C38 H38C 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C33 O2 C34 115.4(4) yes . . . C36 O4 C37 116.0(4) yes . . . C1 N1 C2 107.4(4) yes . . . C17 N2 C18 107.9(4) yes . . . N1 C1 C16 109.9(4) yes . . . N1 C1 C17 120.4(4) yes . . . C16 C1 C17 129.7(4) yes . . . N1 C2 C3 113.5(4) yes . . . N1 C2 C33 122.1(4) yes . . . C3 C2 C33 124.3(4) yes . . . C2 C3 C4 134.3(4) yes . . . C2 C3 C16 104.4(4) yes . . . C4 C3 C16 121.3(4) yes . . . C3 C4 C5 118.7(4) yes . . . C4 C5 C6 121.0(4) yes . . . C4 C5 C14 119.6(4) yes . . . C6 C5 C14 119.4(4) yes . . . C5 C6 C7 122.1(4) yes . . . C6 C7 C8 123.3(4) yes . . . C6 C7 C12 118.3(4) yes . . . C8 C7 C12 118.4(4) yes . . . C7 C8 C9 121.9(5) yes . . . C8 C9 C10 120.0(5) yes . . . C9 C10 C11 121.2(5) yes . . . C10 C11 C12 119.9(4) yes . . . C7 C12 C11 118.6(4) yes . . . C7 C12 C13 118.8(4) yes . . . C11 C12 C13 122.6(4) yes . . . C12 C13 C14 123.1(4) yes . . . C5 C14 C13 118.3(4) yes . . . C5 C14 C15 120.4(4) yes . . . C13 C14 C15 121.2(4) yes . . . C14 C15 C16 118.5(4) yes . . . C1 C16 C3 104.8(4) yes . . . C1 C16 C15 133.9(4) yes . . . C3 C16 C15 121.3(4) yes . . . N2 C17 C1 120.6(4) yes . . . N2 C17 C32 108.7(4) yes . . . C1 C17 C32 130.7(4) yes . . . N2 C18 C19 113.4(4) yes . . . N2 C18 C36 121.7(4) yes . . . C19 C18 C36 124.8(4) yes . . . C18 C19 C20 134.6(4) yes . . . C18 C19 C32 104.6(4) yes . . . C20 C19 C32 120.8(4) yes . . . C19 C20 C21 118.9(4) yes . . . C20 C21 C22 120.7(4) yes . . . C20 C21 C30 119.7(4) yes . . . C22 C21 C30 119.6(4) yes . . . C21 C22 C23 121.2(4) yes . . . C22 C23 C24 123.0(4) yes . . . C22 C23 C28 119.8(4) yes . . . C24 C23 C28 117.3(4) yes . . . C23 C24 C25 122.0(5) yes . . . C24 C25 C26 120.2(5) yes . . . C25 C26 C27 120.1(5) yes . . . C26 C27 C28 121.1(5) yes . . . C23 C28 C27 119.3(4) yes . . . C23 C28 C29 118.8(4) yes . . . C27 C28 C29 121.8(4) yes . . . C28 C29 C30 121.4(4) yes . . . C21 C30 C29 119.1(4) yes . . . C21 C30 C31 119.9(4) yes . . . C29 C30 C31 120.9(4) yes . . . C30 C31 C32 118.6(4) yes . . . C17 C32 C19 105.2(4) yes . . . C17 C32 C31 132.9(4) yes . . . C19 C32 C31 121.9(4) yes . . . O1 C33 O2 124.6(4) yes . . . O1 C33 C2 123.9(4) yes . . . O2 C33 C2 111.5(4) yes . . . O2 C34 C35 106.3(4) yes . . . O3 C36 O4 123.8(4) yes . . . O3 C36 C18 124.9(5) yes . . . O4 C36 C18 111.2(4) yes . . . O4 C37 C38 106.3(4) yes . . . C3 C4 H4 120.635 no . . . C5 C4 H4 120.641 no . . . C5 C6 H6 118.963 no . . . C7 C6 H6 118.957 no . . . C7 C8 H8 119.059 no . . . C9 C8 H8 119.057 no . . . C8 C9 H9 120.002 no . . . C10 C9 H9 119.997 no . . . C9 C10 H10 119.402 no . . . C11 C10 H10 119.397 no . . . C10 C11 H11 120.032 no . . . C12 C11 H11 120.044 no . . . C12 C13 H13 118.462 no . . . C14 C13 H13 118.464 no . . . C14 C15 H15 120.753 no . . . C16 C15 H15 120.742 no . . . C19 C20 H20 120.559 no . . . C21 C20 H20 120.543 no . . . C21 C22 H22 119.418 no . . . C23 C22 H22 119.404 no . . . C23 C24 H24 118.998 no . . . C25 C24 H24 118.987 no . . . C24 C25 H25 119.897 no . . . C26 C25 H25 119.895 no . . . C25 C26 H26 119.975 no . . . C27 C26 H26 119.966 no . . . C26 C27 H27 119.466 no . . . C28 C27 H27 119.454 no . . . C28 C29 H29 119.302 no . . . C30 C29 H29 119.308 no . . . C30 C31 H31 120.700 no . . . C32 C31 H31 120.687 no . . . O2 C34 H34A 110.467 no . . . O2 C34 H34B 110.472 no . . . C35 C34 H34A 110.486 no . . . C35 C34 H34B 110.480 no . . . H34A C34 H34B 108.667 no . . . C34 C35 H35A 109.474 no . . . C34 C35 H35B 109.467 no . . . C34 C35 H35C 109.480 no . . . H35A C35 H35B 109.463 no . . . H35A C35 H35C 109.475 no . . . H35B C35 H35C 109.468 no . . . O4 C37 H37A 110.459 no . . . O4 C37 H37B 110.471 no . . . C38 C37 H37A 110.462 no . . . C38 C37 H37B 110.464 no . . . H37A C37 H37B 108.660 no . . . C37 C38 H38A 109.471 no . . . C37 C38 H38B 109.465 no . . . C37 C38 H38C 109.466 no . . . H38A C38 H38B 109.477 no . . . H38A C38 H38C 109.477 no . . . H38B C38 H38C 109.471 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C33 O2 C34 C35 -170.2(3) no . . . . C34 O2 C33 O1 -2.5(6) no . . . . C34 O2 C33 C2 175.1(3) no . . . . C36 O4 C37 C38 168.6(4) no . . . . C37 O4 C36 O3 3.2(6) no . . . . C37 O4 C36 C18 -173.8(4) no . . . . C1 N1 C2 C3 0.7(5) no . . . . C1 N1 C2 C33 -175.9(4) no . . . . C2 N1 C1 C16 0.9(5) no . . . . C2 N1 C1 C17 -179.7(4) no . . . . C17 N2 C18 C19 -2.1(5) no . . . . C17 N2 C18 C36 175.1(4) no . . . . C18 N2 C17 C1 -179.4(4) no . . . . C18 N2 C17 C32 -0.5(5) no . . . . N1 C1 C16 C3 -2.1(5) no . . . . N1 C1 C16 C15 176.4(4) no . . . . N1 C1 C17 N2 178.9(4) no . . . . N1 C1 C17 C32 0.3(7) no . . . . C16 C1 C17 N2 -1.8(7) no . . . . C16 C1 C17 C32 179.6(4) no . . . . C17 C1 C16 C3 178.5(5) no . . . . C17 C1 C16 C15 -3.0(9) no . . . . N1 C2 C3 C4 179.6(4) no . . . . N1 C2 C3 C16 -2.1(5) no . . . . N1 C2 C33 O1 -177.5(4) no . . . . N1 C2 C33 O2 4.8(6) no . . . . C3 C2 C33 O1 6.2(7) no . . . . C3 C2 C33 O2 -171.5(4) no . . . . C33 C2 C3 C4 -3.8(8) no . . . . C33 C2 C3 C16 174.5(4) no . . . . C2 C3 C4 C5 178.2(4) no . . . . C2 C3 C16 C1 2.4(5) no . . . . C2 C3 C16 C15 -176.3(4) no . . . . C4 C3 C16 C1 -179.0(4) no . . . . C4 C3 C16 C15 2.2(7) no . . . . C16 C3 C4 C5 0.1(6) no . . . . C3 C4 C5 C6 178.5(4) no . . . . C3 C4 C5 C14 -3.4(6) no . . . . C4 C5 C6 C7 177.7(4) no . . . . C4 C5 C14 C13 -177.5(4) no . . . . C4 C5 C14 C15 4.6(6) no . . . . C6 C5 C14 C13 0.6(6) no . . . . C6 C5 C14 C15 -177.4(4) no . . . . C14 C5 C6 C7 -0.3(7) no . . . . C5 C6 C7 C8 -179.7(4) no . . . . C5 C6 C7 C12 -0.9(6) no . . . . C6 C7 C8 C9 179.7(4) no . . . . C6 C7 C12 C11 -179.1(4) no . . . . C6 C7 C12 C13 1.9(6) no . . . . C8 C7 C12 C11 -0.2(6) no . . . . C8 C7 C12 C13 -179.3(4) no . . . . C12 C7 C8 C9 1.0(7) no . . . . C7 C8 C9 C10 -0.6(7) no . . . . C8 C9 C10 C11 -0.5(8) no . . . . C9 C10 C11 C12 1.2(7) no . . . . C10 C11 C12 C7 -0.8(7) no . . . . C10 C11 C12 C13 178.2(4) no . . . . C7 C12 C13 C14 -1.7(7) no . . . . C11 C12 C13 C14 179.3(4) no . . . . C12 C13 C14 C5 0.5(7) no . . . . C12 C13 C14 C15 178.4(4) no . . . . C5 C14 C15 C16 -2.2(6) no . . . . C13 C14 C15 C16 179.9(4) no . . . . C14 C15 C16 C1 -179.4(4) no . . . . C14 C15 C16 C3 -1.1(6) no . . . . N2 C17 C32 C19 2.9(5) no . . . . N2 C17 C32 C31 -176.5(4) no . . . . C1 C17 C32 C19 -178.4(5) no . . . . C1 C17 C32 C31 2.2(8) no . . . . N2 C18 C19 C20 -176.4(4) no . . . . N2 C18 C19 C32 3.9(5) no . . . . N2 C18 C36 O3 -179.0(4) no . . . . N2 C18 C36 O4 -1.9(6) no . . . . C19 C18 C36 O3 -2.1(7) no . . . . C19 C18 C36 O4 175.0(4) no . . . . C36 C18 C19 C20 6.4(8) no . . . . C36 C18 C19 C32 -173.2(4) no . . . . C18 C19 C20 C21 -178.0(5) no . . . . C18 C19 C32 C17 -3.9(5) no . . . . C18 C19 C32 C31 175.6(4) no . . . . C20 C19 C32 C17 176.4(4) no . . . . C20 C19 C32 C31 -4.1(7) no . . . . C32 C19 C20 C21 1.6(6) no . . . . C19 C20 C21 C22 -179.0(4) no . . . . C19 C20 C21 C30 1.7(6) no . . . . C20 C21 C22 C23 -176.9(4) no . . . . C20 C21 C30 C29 175.9(4) no . . . . C20 C21 C30 C31 -2.8(6) no . . . . C22 C21 C30 C29 -3.5(6) no . . . . C22 C21 C30 C31 177.9(4) no . . . . C30 C21 C22 C23 2.4(7) no . . . . C21 C22 C23 C24 -179.8(4) no . . . . C21 C22 C23 C28 0.0(7) no . . . . C22 C23 C24 C25 -179.5(4) no . . . . C22 C23 C28 C27 179.2(4) no . . . . C22 C23 C28 C29 -1.4(6) no . . . . C24 C23 C28 C27 -1.0(6) no . . . . C24 C23 C28 C29 178.4(4) no . . . . C28 C23 C24 C25 0.7(7) no . . . . C23 C24 C25 C26 0.9(7) no . . . . C24 C25 C26 C27 -2.2(7) no . . . . C25 C26 C27 C28 1.9(7) no . . . . C26 C27 C28 C23 -0.3(7) no . . . . C26 C27 C28 C29 -179.7(4) no . . . . C23 C28 C29 C30 0.3(7) no . . . . C27 C28 C29 C30 179.7(4) no . . . . C28 C29 C30 C21 2.1(6) no . . . . C28 C29 C30 C31 -179.3(4) no . . . . C21 C30 C31 C32 0.4(6) no . . . . C29 C30 C31 C32 -178.2(4) no . . . . C30 C31 C32 C17 -177.8(4) no . . . . C30 C31 C32 C19 2.9(6) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 N1 3.535(5) no . . O1 C3 2.980(6) no . . O1 C4 3.120(6) no . . O1 C34 2.659(6) no . . O2 N1 2.684(5) no . . O3 N2 3.535(5) no . . O3 C19 2.996(6) no . . O3 C20 3.152(6) no . . O3 C37 2.666(6) no . . O4 N2 2.663(5) no . . N1 C31 3.140(6) no . . N1 C32 3.027(6) no . . N2 C15 3.127(6) no . . N2 C16 3.009(6) no . . C1 C18 3.476(7) no . . C1 C31 3.285(6) no . . C2 C15 3.593(6) no . . C2 C17 3.461(6) no . . C3 C14 2.797(7) no . . C4 C15 2.868(7) no . . C4 C33 3.259(6) no . . C5 C12 2.843(7) no . . C5 C16 2.811(6) no . . C6 C13 2.790(7) no . . C7 C10 2.799(7) no . . C7 C14 2.858(6) no . . C8 C11 2.800(7) no . . C9 C12 2.814(7) no . . C15 C17 3.274(6) no . . C18 C31 3.592(7) no . . C19 C30 2.808(6) no . . C20 C31 2.862(7) no . . C20 C36 3.260(7) no . . C21 C28 2.832(6) no . . C21 C32 2.794(6) no . . C22 C29 2.811(7) no . . C23 C26 2.840(7) no . . C23 C30 2.825(6) no . . C24 C27 2.798(8) no . . C25 C28 2.822(7) no . . O1 C2 3.422(6) no . 1_455 O1 C20 3.418(6) no . 2_646 O1 C22 3.356(6) no . 2_646 O1 C33 3.420(6) no . 1_455 O2 C34 3.532(6) no . 1_655 O3 O4 3.551(5) no . 1_655 O3 N2 3.522(5) no . 1_655 O3 C18 3.321(6) no . 1_655 O3 C34 3.078(6) no . 2_656 O3 C34 3.446(6) no . 2_756 O3 C35 3.378(7) no . 2_656 O3 C35 3.533(7) no . 2_756 O3 C36 3.345(6) no . 1_655 O4 O3 3.551(5) no . 1_455 O4 C37 3.495(6) no . 1_455 N1 C2 3.354(6) no . 1_655 N1 C3 3.598(6) no . 1_655 N1 C31 3.434(6) no . 1_455 N1 C32 3.420(6) no . 1_455 N1 C33 3.371(6) no . 1_655 N2 O3 3.522(5) no . 1_455 N2 C1 3.585(6) no . 1_655 N2 C15 3.380(6) no . 1_655 N2 C16 3.385(6) no . 1_655 N2 C18 3.339(6) no . 1_455 N2 C36 3.318(6) no . 1_455 C1 N2 3.585(6) no . 1_455 C1 C2 3.496(6) no . 1_655 C1 C3 3.295(7) no . 1_655 C1 C16 3.515(7) no . 1_655 C1 C17 3.346(6) no . 1_455 C1 C32 3.351(7) no . 1_455 C2 O1 3.422(6) no . 1_655 C2 N1 3.354(6) no . 1_455 C2 C1 3.496(6) no . 1_455 C2 C33 3.600(6) no . 1_655 C3 N1 3.598(6) no . 1_455 C3 C1 3.295(7) no . 1_455 C3 C4 3.425(6) no . 1_655 C3 C16 3.512(6) no . 1_455 C4 C3 3.425(6) no . 1_455 C4 C16 3.349(7) no . 1_455 C5 C6 3.464(7) no . 1_655 C5 C14 3.578(6) no . 1_455 C5 C15 3.397(6) no . 1_455 C5 C16 3.533(7) no . 1_455 C6 C5 3.464(7) no . 1_455 C6 C14 3.445(6) no . 1_455 C7 C8 3.462(7) no . 1_655 C7 C13 3.448(6) no . 1_455 C8 C7 3.462(7) no . 1_455 C8 C12 3.463(7) no . 1_455 C9 C10 3.596(7) no . 1_455 C9 C11 3.479(7) no . 1_455 C10 C9 3.596(7) no . 1_655 C10 C11 3.475(7) no . 1_455 C11 C9 3.479(7) no . 1_655 C11 C10 3.475(7) no . 1_655 C12 C8 3.463(7) no . 1_655 C12 C13 3.447(7) no . 1_455 C13 C7 3.448(6) no . 1_655 C13 C12 3.447(7) no . 1_655 C14 C5 3.578(6) no . 1_655 C14 C6 3.445(6) no . 1_655 C14 C15 3.401(6) no . 1_455 C15 N2 3.380(6) no . 1_455 C15 C5 3.397(6) no . 1_655 C15 C14 3.401(6) no . 1_655 C16 N2 3.385(6) no . 1_455 C16 C1 3.515(7) no . 1_455 C16 C3 3.512(6) no . 1_655 C16 C4 3.349(7) no . 1_655 C16 C5 3.533(7) no . 1_655 C16 C17 3.343(7) no . 1_455 C17 C1 3.346(6) no . 1_655 C17 C16 3.343(7) no . 1_655 C17 C18 3.464(6) no . 1_455 C17 C19 3.301(6) no . 1_455 C17 C32 3.513(6) no . 1_455 C18 O3 3.321(6) no . 1_455 C18 N2 3.339(6) no . 1_655 C18 C17 3.464(6) no . 1_655 C18 C36 3.569(7) no . 1_455 C19 C17 3.301(6) no . 1_655 C19 C20 3.483(6) no . 1_455 C19 C32 3.515(6) no . 1_655 C20 O1 3.418(6) no . 2_656 C20 C19 3.483(6) no . 1_655 C20 C32 3.404(6) no . 1_655 C21 C22 3.510(7) no . 1_455 C21 C30 3.579(6) no . 1_655 C21 C31 3.454(6) no . 1_655 C22 O1 3.356(6) no . 2_656 C22 C21 3.510(7) no . 1_655 C22 C30 3.492(6) no . 1_655 C23 C24 3.520(7) no . 1_455 C23 C29 3.516(6) no . 1_655 C24 C23 3.520(7) no . 1_655 C24 C28 3.547(7) no . 1_655 C25 C27 3.552(7) no . 1_655 C26 C27 3.487(7) no . 1_655 C27 C25 3.552(7) no . 1_455 C27 C26 3.487(7) no . 1_455 C28 C24 3.547(7) no . 1_455 C28 C29 3.482(7) no . 1_655 C29 C23 3.516(6) no . 1_455 C29 C28 3.482(7) no . 1_455 C30 C21 3.579(6) no . 1_455 C30 C22 3.492(6) no . 1_455 C30 C31 3.463(6) no . 1_655 C31 N1 3.434(6) no . 1_655 C31 C21 3.454(6) no . 1_455 C31 C30 3.463(6) no . 1_455 C32 N1 3.420(6) no . 1_655 C32 C1 3.351(7) no . 1_655 C32 C17 3.513(6) no . 1_655 C32 C19 3.515(6) no . 1_455 C32 C20 3.404(6) no . 1_455 C33 O1 3.420(6) no . 1_655 C33 N1 3.371(6) no . 1_455 C33 C2 3.600(6) no . 1_455 C34 O2 3.532(6) no . 1_455 C34 O3 3.078(6) no . 2_646 C34 O3 3.446(6) no . 2_746 C35 O3 3.378(7) no . 2_646 C35 O3 3.533(7) no . 2_746 C36 O3 3.345(6) no . 1_455 C36 N2 3.318(6) no . 1_655 C36 C18 3.569(7) no . 1_655 C37 O4 3.495(6) no . 1_655 O1 H4 2.6021 no . . O1 H34A 2.7452 no . . O1 H34B 2.5393 no . . O2 H35A 2.5809 no . . O2 H35B 3.2199 no . . O2 H35C 2.5269 no . . O3 H20 2.6438 no . . O3 H37A 2.5358 no . . O3 H37B 2.7707 no . . O4 H38A 2.5773 no . . O4 H38B 3.2150 no . . O4 H38C 2.5151 no . . N1 H31 2.6047 no . . N2 H15 2.5954 no . . C1 H15 2.8697 no . . C1 H31 3.1430 no . . C2 H4 2.8786 no . . C3 H15 3.3113 no . . C4 H6 2.6284 no . . C5 H13 3.2918 no . . C5 H15 3.3507 no . . C6 H4 2.6622 no . . C6 H8 2.6695 no . . C7 H9 3.2657 no . . C7 H11 3.3312 no . . C7 H13 3.3028 no . . C8 H6 2.6674 no . . C8 H10 3.2411 no . . C9 H11 3.2866 no . . C10 H8 3.2499 no . . C11 H9 3.2798 no . . C11 H13 2.6347 no . . C12 H6 3.3137 no . . C12 H8 3.3165 no . . C12 H10 3.2738 no . . C13 H11 2.6686 no . . C13 H15 2.6711 no . . C14 H4 3.3372 no . . C14 H6 3.3076 no . . C15 H13 2.6243 no . . C16 H4 3.3201 no . . C17 H15 3.1400 no . . C17 H31 2.8609 no . . C18 H20 2.8676 no . . C19 H31 3.3139 no . . C20 H22 2.6223 no . . C21 H29 3.3087 no . . C21 H31 3.3415 no . . C22 H20 2.6547 no . . C22 H24 2.6752 no . . C23 H25 3.3033 no . . C23 H27 3.3307 no . . C23 H29 3.3072 no . . C24 H22 2.6676 no . . C24 H26 3.2681 no . . C25 H27 3.2815 no . . C26 H24 3.2706 no . . C27 H25 3.2773 no . . C27 H29 2.6389 no . . C28 H22 3.3131 no . . C28 H24 3.3183 no . . C28 H26 3.2921 no . . C29 H27 2.6493 no . . C29 H31 2.6558 no . . C30 H20 3.3477 no . . C30 H22 3.3058 no . . C31 H29 2.6266 no . . C32 H20 3.3036 no . . C33 H4 3.0783 no . . C33 H34A 2.6785 no . . C33 H34B 2.5518 no . . C36 H20 3.0856 no . . C36 H37A 2.5605 no . . C36 H37B 2.7069 no . . H4 H6 2.4749 no . . H6 H8 2.5047 no . . H8 H9 2.2816 no . . H9 H10 2.3588 no . . H10 H11 2.3130 no . . H11 H13 2.4850 no . . H13 H15 2.4754 no . . H20 H22 2.4681 no . . H22 H24 2.5084 no . . H24 H25 2.2980 no . . H25 H26 2.3709 no . . H26 H27 2.3180 no . . H27 H29 2.4722 no . . H29 H31 2.4725 no . . H34A H35A 2.3494 no . . H34A H35B 2.3898 no . . H34A H35C 2.8603 no . . H34B H35A 2.8603 no . . H34B H35B 2.3508 no . . H34B H35C 2.3883 no . . H37A H38A 2.3351 no . . H37A H38B 2.3813 no . . H37A H38C 2.8505 no . . H37B H38A 2.8506 no . . H37B H38B 2.3364 no . . H37B H38C 2.3798 no . . O1 H20 2.9630 no . 2_646 O1 H22 2.8275 no . 2_646 O1 H22 2.8335 no . 2_746 O2 H31 3.4280 no . 1_455 O2 H34B 2.6540 no . 1_655 O3 H34A 2.8523 no . 2_656 O3 H34A 2.6425 no . 2_756 O3 H34B 2.6970 no . 2_656 O3 H35A 3.1530 no . 2_756 O3 H35B 2.7568 no . 2_656 O3 H35B 3.4670 no . 2_756 O4 H15 3.3575 no . 1_655 O4 H37A 2.5928 no . 1_455 N1 H31 3.3979 no . 1_455 N2 H15 3.3721 no . 1_655 C3 H4 3.3030 no . 1_655 C4 H4 3.5726 no . 1_655 C4 H24 2.9084 no . 2_746 C5 H6 3.3882 no . 1_655 C5 H24 3.3868 no . 2_746 C6 H24 3.3868 no . 2_746 C6 H25 3.4012 no . 2_746 C7 H8 3.3794 no . 1_655 C8 H37B 3.3393 no . 2_645 C8 H38B 3.0693 no . 2_645 C9 H9 3.5387 no . 1_655 C9 H35A 3.4100 no . 1_454 C9 H35B 3.3911 no . 1_454 C9 H37A 3.3624 no . 2_645 C9 H37B 3.3728 no . 2_545 C9 H37B 3.0276 no . 2_645 C10 H9 3.4472 no . 1_655 C10 H11 3.4310 no . 1_455 C10 H27 3.2072 no . 1_354 C10 H35A 3.3437 no . 1_454 C11 H13 3.5997 no . 1_455 C11 H26 3.4940 no . 1_354 C11 H27 3.2370 no . 1_354 C11 H27 3.3398 no . 1_454 C12 H13 3.3533 no . 1_455 C13 H15 3.5506 no . 1_455 C13 H38A 3.6000 no . 1_455 C14 H15 3.2978 no . 1_455 C15 H15 3.5819 no . 1_455 C18 H34A 3.5139 no . 2_656 C19 H20 3.3852 no . 1_455 C19 H34A 3.5642 no . 2_656 C20 H20 3.5955 no . 1_455 C20 H34A 3.3748 no . 2_656 C20 H34B 3.5361 no . 2_656 C21 H22 3.4657 no . 1_455 C23 H24 3.4823 no . 1_455 C24 H4 3.3810 no . 2_756 C24 H6 3.0590 no . 2_656 C24 H6 3.5733 no . 2_756 C25 H6 3.1824 no . 2_656 C25 H6 3.5561 no . 2_756 C25 H8 3.4674 no . 2_656 C25 H25 3.5817 no . 1_455 C25 H38B 3.5908 no . 1_556 C25 H38B 3.3150 no . 1_656 C25 H38C 3.4557 no . 1_656 C26 H11 3.2031 no . 1_756 C26 H25 3.5595 no . 1_455 C26 H27 3.4398 no . 1_655 C26 H38A 3.5463 no . 1_556 C26 H38B 3.4166 no . 1_556 C26 H38C 3.2793 no . 1_656 C27 H10 3.5187 no . 1_756 C27 H11 3.3398 no . 1_656 C27 H11 3.2362 no . 1_756 C28 H29 3.4320 no . 1_655 C30 H31 3.3830 no . 1_655 C33 H22 3.3679 no . 2_746 C33 H34B 3.3572 no . 1_655 C34 H20 3.2704 no . 2_646 C34 H34A 3.5130 no . 1_455 C34 H34B 2.9120 no . 1_655 C34 H35A 3.2292 no . 1_455 C35 H9 3.0953 no . 1_656 C35 H10 3.2425 no . 1_656 C35 H34B 3.2355 no . 1_655 C35 H35A 2.9151 no . 1_455 C35 H35B 3.5392 no . 1_655 C35 H35C 3.5652 no . 1_655 C36 H34A 3.2018 no . 2_656 C36 H34B 3.5709 no . 2_656 C36 H35B 3.3148 no . 2_656 C36 H37A 3.3720 no . 1_455 C37 H8 3.5016 no . 2_655 C37 H9 3.4938 no . 2_555 C37 H9 3.1762 no . 2_655 C37 H35B 3.4466 no . 2_656 C37 H37A 2.9012 no . 1_455 C37 H37B 3.5625 no . 1_655 C37 H38C 3.1614 no . 1_655 C38 H8 3.3371 no . 2_655 C38 H13 3.5828 no . 1_655 C38 H25 3.1557 no . 1_454 C38 H26 3.1437 no . 1_454 C38 H26 3.4336 no . 1_554 C38 H37A 3.1626 no . 1_455 C38 H38A 3.5003 no . 1_455 C38 H38C 2.9099 no . 1_655 H4 C3 3.3030 no . 1_455 H4 C4 3.5726 no . 1_455 H4 C24 3.3810 no . 2_746 H4 H22 3.2874 no . 2_646 H4 H22 3.4742 no . 2_746 H4 H24 3.2027 no . 2_646 H4 H24 2.4583 no . 2_746 H6 C5 3.3882 no . 1_455 H6 C24 3.0590 no . 2_646 H6 C24 3.5733 no . 2_746 H6 C25 3.1824 no . 2_646 H6 C25 3.5561 no . 2_746 H6 H24 2.7962 no . 2_646 H6 H24 2.9566 no . 2_746 H6 H25 3.0162 no . 2_646 H6 H25 2.9372 no . 2_746 H8 C7 3.3794 no . 1_455 H8 C25 3.4674 no . 2_646 H8 C37 3.5016 no . 2_645 H8 C38 3.3371 no . 2_645 H8 H25 2.7818 no . 2_646 H8 H37A 3.3050 no . 2_645 H8 H37B 3.3610 no . 2_545 H8 H37B 3.3146 no . 2_645 H8 H38B 3.2763 no . 2_545 H8 H38B 2.4957 no . 2_645 H8 H38C 3.1971 no . 2_545 H9 C9 3.5387 no . 1_455 H9 C10 3.4472 no . 1_455 H9 C35 3.0953 no . 1_454 H9 C37 3.4938 no . 2_545 H9 C37 3.1762 no . 2_645 H9 H35A 2.8284 no . 1_454 H9 H35B 2.5678 no . 1_454 H9 H35B 3.5292 no . 1_554 H9 H35C 3.4719 no . 1_454 H9 H37A 2.7332 no . 2_645 H9 H37B 2.5556 no . 2_545 H9 H37B 2.7597 no . 2_645 H9 H38B 3.5942 no . 2_645 H10 C27 3.5187 no . 1_354 H10 C35 3.2425 no . 1_454 H10 H11 3.5262 no . 1_455 H10 H27 2.8135 no . 1_354 H10 H35A 2.6840 no . 1_454 H10 H35B 3.3894 no . 1_454 H10 H35B 3.2652 no . 1_554 H10 H35C 3.1555 no . 1_454 H10 H35C 3.0522 no . 1_554 H11 C10 3.4310 no . 1_655 H11 C26 3.2031 no . 1_354 H11 C27 3.2362 no . 1_354 H11 C27 3.3398 no . 1_454 H11 H10 3.5262 no . 1_655 H11 H26 2.7864 no . 1_354 H11 H27 2.8642 no . 1_354 H11 H27 2.5234 no . 1_454 H13 C11 3.5997 no . 1_655 H13 C12 3.3533 no . 1_655 H13 C38 3.5828 no . 1_455 H13 H38A 2.7189 no . 1_455 H15 O4 3.3575 no . 1_455 H15 N2 3.3721 no . 1_455 H15 C13 3.5506 no . 1_655 H15 C14 3.2978 no . 1_655 H15 C15 3.5819 no . 1_655 H15 H38A 3.2866 no . 1_455 H20 O1 2.9630 no . 2_656 H20 C19 3.3852 no . 1_655 H20 C20 3.5955 no . 1_655 H20 C34 3.2704 no . 2_656 H20 H34A 2.9193 no . 2_656 H20 H34A 2.7766 no . 2_756 H20 H34B 2.7277 no . 2_656 H22 O1 2.8275 no . 2_656 H22 O1 2.8335 no . 2_756 H22 C21 3.4657 no . 1_655 H22 C33 3.3679 no . 2_756 H22 H4 3.2874 no . 2_656 H22 H4 3.4742 no . 2_756 H24 C4 2.9084 no . 2_756 H24 C5 3.3868 no . 2_756 H24 C6 3.3868 no . 2_756 H24 C23 3.4823 no . 1_655 H24 H4 3.2027 no . 2_656 H24 H4 2.4583 no . 2_756 H24 H6 2.7962 no . 2_656 H24 H6 2.9566 no . 2_756 H25 C6 3.4012 no . 2_756 H25 C25 3.5817 no . 1_655 H25 C26 3.5595 no . 1_655 H25 C38 3.1557 no . 1_656 H25 H6 3.0162 no . 2_656 H25 H6 2.9372 no . 2_756 H25 H8 2.7818 no . 2_656 H25 H38B 3.3764 no . 1_556 H25 H38B 2.5508 no . 1_656 H25 H38C 2.9230 no . 1_656 H26 C11 3.4940 no . 1_756 H26 C38 3.4336 no . 1_556 H26 C38 3.1437 no . 1_656 H26 H11 2.7864 no . 1_756 H26 H27 3.5032 no . 1_655 H26 H38A 2.8809 no . 1_556 H26 H38A 3.1648 no . 1_656 H26 H38B 3.0886 no . 1_556 H26 H38B 3.2113 no . 1_656 H26 H38C 2.5666 no . 1_656 H27 C10 3.2072 no . 1_756 H27 C11 3.3398 no . 1_656 H27 C11 3.2370 no . 1_756 H27 C26 3.4398 no . 1_455 H27 H10 2.8135 no . 1_756 H27 H11 2.5234 no . 1_656 H27 H11 2.8642 no . 1_756 H27 H26 3.5032 no . 1_455 H29 C28 3.4320 no . 1_455 H29 H35C 2.8608 no . 1_655 H31 O2 3.4280 no . 1_655 H31 N1 3.3979 no . 1_655 H31 C30 3.3830 no . 1_455 H31 H35C 3.3703 no . 1_655 H34A O3 2.8523 no . 2_646 H34A O3 2.6425 no . 2_746 H34A C18 3.5139 no . 2_646 H34A C19 3.5642 no . 2_646 H34A C20 3.3748 no . 2_646 H34A C34 3.5130 no . 1_655 H34A C36 3.2018 no . 2_646 H34A H20 2.9193 no . 2_646 H34A H20 2.7766 no . 2_746 H34A H34B 2.5562 no . 1_655 H34B O2 2.6540 no . 1_455 H34B O3 2.6970 no . 2_646 H34B C20 3.5361 no . 2_646 H34B C33 3.3572 no . 1_455 H34B C34 2.9120 no . 1_455 H34B C35 3.2355 no . 1_455 H34B C36 3.5709 no . 2_646 H34B H20 2.7277 no . 2_646 H34B H34A 2.5562 no . 1_455 H34B H35A 2.6409 no . 1_455 H35A O3 3.1530 no . 2_746 H35A C9 3.4100 no . 1_656 H35A C10 3.3437 no . 1_656 H35A C34 3.2292 no . 1_655 H35A C35 2.9151 no . 1_655 H35A H9 2.8284 no . 1_656 H35A H10 2.6840 no . 1_656 H35A H34B 2.6409 no . 1_655 H35A H35B 2.5979 no . 1_655 H35A H35C 2.6334 no . 1_655 H35B O3 2.7568 no . 2_646 H35B O3 3.4670 no . 2_746 H35B C9 3.3911 no . 1_656 H35B C35 3.5392 no . 1_455 H35B C36 3.3148 no . 2_646 H35B C37 3.4466 no . 2_646 H35B H9 3.5292 no . 1_556 H35B H9 2.5678 no . 1_656 H35B H10 3.2652 no . 1_556 H35B H10 3.3894 no . 1_656 H35B H35A 2.5979 no . 1_455 H35B H37B 2.6825 no . 2_646 H35C C35 3.5652 no . 1_455 H35C H9 3.4719 no . 1_656 H35C H10 3.0522 no . 1_556 H35C H10 3.1555 no . 1_656 H35C H29 2.8608 no . 1_455 H35C H31 3.3703 no . 1_455 H35C H35A 2.6334 no . 1_455 H37A O4 2.5928 no . 1_655 H37A C9 3.3624 no . 2_655 H37A C36 3.3720 no . 1_655 H37A C37 2.9012 no . 1_655 H37A C38 3.1626 no . 1_655 H37A H8 3.3050 no . 2_655 H37A H9 2.7332 no . 2_655 H37A H37B 2.6117 no . 1_655 H37A H38C 2.5431 no . 1_655 H37B C8 3.3393 no . 2_655 H37B C9 3.3728 no . 2_555 H37B C9 3.0276 no . 2_655 H37B C37 3.5625 no . 1_455 H37B H8 3.3610 no . 2_555 H37B H8 3.3146 no . 2_655 H37B H9 2.5556 no . 2_555 H37B H9 2.7597 no . 2_655 H37B H35B 2.6825 no . 2_656 H37B H37A 2.6117 no . 1_455 H38A C13 3.6000 no . 1_655 H38A C26 3.5463 no . 1_554 H38A C38 3.5003 no . 1_655 H38A H13 2.7189 no . 1_655 H38A H15 3.2866 no . 1_655 H38A H26 3.1648 no . 1_454 H38A H26 2.8809 no . 1_554 H38A H38C 2.5388 no . 1_655 H38B C8 3.0693 no . 2_655 H38B C25 3.3150 no . 1_454 H38B C25 3.5908 no . 1_554 H38B C26 3.4166 no . 1_554 H38B H8 3.2763 no . 2_555 H38B H8 2.4957 no . 2_655 H38B H9 3.5942 no . 2_655 H38B H25 2.5508 no . 1_454 H38B H25 3.3764 no . 1_554 H38B H26 3.2113 no . 1_454 H38B H26 3.0886 no . 1_554 H38B H38C 2.7182 no . 1_655 H38C C25 3.4557 no . 1_454 H38C C26 3.2793 no . 1_454 H38C C37 3.1614 no . 1_455 H38C C38 2.9099 no . 1_455 H38C H8 3.1971 no . 2_555 H38C H25 2.9230 no . 1_454 H38C H26 2.5666 no . 1_454 H38C H37A 2.5431 no . 1_455 H38C H38A 2.5388 no . 1_455 H38C H38B 2.7182 no . 1_455 #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================