# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' #TrackingRef '- cifs 1-8_(R2).cif' _journal_coden_Cambridge 0440 #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2010-05-27 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? #------------------ AUTHOR DETAILS -------------------------------------------# _publ_contact_author ; Rosa Santillan Departamento de Qu\'imica Centro de Investigaci\'on y de Estudios Avanzados del Instituto Polit\'ecnico Nacional Apartado Postal 14-740 07000 M\'exico, D.F. M\'exico ; _publ_contact_author_phone '555 747 3725' _publ_contact_author_fax '555 747 3389' _publ_contact_author_email rsantill@cinvestav.mx _publ_section_title ; X-Ray crystallographic and spectroscopic properties of eight Schiff Bases as evidence of the protor transfer reaction. Role of the intermolecular hydrogen bond ; loop_ _publ_author_name _publ_author_address O.Dominguez ; Departamento de Qu\'imica Centro de Investigaci\'on y de Estudios Avanzados del Instituto Polit\'ecnico Nacional Apartado Postal 14-740 07000 M\'exico, D.F. M\'exico ; B.Rodriguez-Molina ; Departamento de Qu\'imica Centro de Investigaci\'on y de Estudios Avanzados del Instituto Polit\'ecnico Nacional Apartado Postal 14-740 07000 M\'exico, D.F. M\'exico ; M.Rodriguez ; Centro de Investigaciones en \'Optica Apartado Postal 1-948 3700 Le\'on Guanajuato M\'exico ; 'Armando Ariza' ; Departamento de Qu\'imica Centro de Investigaci\'on y de Estudios Avanzados del Instituto Polit\'ecnico Nacional Apartado Postal 14-740 07000 M\'exico, D.F. M\'exico ; N.Farfan ; Departamento de Qu\'imica Org\'anica Facultad de Qu\'imica Universidad Nacional Aut\'onoma de M\'exico 04510 M\'exico, D.F. M\'exico ; ; R.Santillan ; ; Departamento de Qu\'imica Centro de Investigaci\'on y de Estudios Avanzados del Instituto Polit\'ecnico Nacional Apartado Postal 14-740 07000 M\'exico, D.F. M\'exico ; _publ_requested_category FO _publ_contact_author_name 'Rosa Santillan' #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_Compound1 _database_code_depnum_ccdc_archive 'CCDC 712147' #TrackingRef '- cifs 1-8_(R2).cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2,4-di-tert-butyl-6-[(1-hydroxy-cyclohexylmethylimino)-methyl]-phenol ; _chemical_formula_moiety 'C22 H35 N1 O2' _chemical_formula_sum 'C22 H35 N1 O2' _chemical_formula_weight 345.51 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _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 14.5103(2) _cell_length_b 28.8821(4) _cell_length_c 10.26160(10) _cell_angle_alpha 90 _cell_angle_beta 92.184(4) _cell_angle_gamma 90 _cell_volume 4297.39(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 31186 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour Orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.068 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.74377E-1 _diffrn_orient_matrix_ub_12 0.218607E-1 _diffrn_orient_matrix_ub_13 0.116735E-1 _diffrn_orient_matrix_ub_21 0.212689E-1 _diffrn_orient_matrix_ub_22 -0.16214E-2 _diffrn_orient_matrix_ub_23 -0.666069E-1 _diffrn_orient_matrix_ub_31 -0.593813E-1 _diffrn_orient_matrix_ub_32 0.268005E-1 _diffrn_orient_matrix_ub_33 -0.135515E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_unetI/netI 0.078 _diffrn_reflns_number 32630 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.4 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 9747 _reflns_number_gt 5426 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0848P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.048(4) _refine_ls_number_reflns 9747 _refine_ls_number_parameters 488 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1297 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.191 _refine_ls_wR_factor_gt 0.1604 _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_restrained_S_all 1.02 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.253 _refine_diff_density_min -0.26 _refine_diff_density_rms 0.081 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H1A H 0.7564(16) 0.2475(8) 0.099(2) 0.081(7) Uiso 1 1 d . . . H1B H 0.2558(16) 0.1777(9) 0.361(2) 0.080(7) Uiso 1 1 d . . . H2A H 1.054(2) 0.2633(11) 0.015(3) 0.123(12) Uiso 1 1 d . . . H2B H 0.0893(17) 0.2818(9) 0.282(3) 0.091(9) Uiso 1 1 d . . . H13A H 0.9204(18) 0.3772(9) -0.166(2) 0.093(8) Uiso 1 1 d . . . H13B H 1.0120(18) 0.4095(10) -0.139(3) 0.107(9) Uiso 1 1 d . . . C2A C 0.73769(12) 0.18458(6) 0.12785(16) 0.0422(4) Uani 1 1 d . . . C3A C 0.68695(12) 0.14944(6) 0.18757(16) 0.0439(4) Uani 1 1 d . . . C4A C 0.71220(13) 0.10415(7) 0.16105(16) 0.0481(5) Uani 1 1 d . . . H4A H 0.6799 0.0806 0.201 0.058 Uiso 1 1 calc R . . C5A C 0.78260(13) 0.09117(6) 0.07876(17) 0.0475(5) Uani 1 1 d . . . C6A C 0.83000(13) 0.12666(7) 0.02249(17) 0.0490(5) Uani 1 1 d . . . H6A H 0.8772 0.1195 -0.033 0.059 Uiso 1 1 calc R . . C7A C 0.80955(12) 0.17305(6) 0.04602(16) 0.0429(4) Uani 1 1 d . . . C8A C 0.86177(13) 0.20885(7) -0.01868(17) 0.0458(5) Uani 1 1 d . . . H8A H 0.9091 0.1999 -0.0719 0.055 Uiso 1 1 calc R . . C10A C 0.90271(13) 0.28490(7) -0.07190(16) 0.0477(5) Uani 1 1 d . . . H10A H 0.8634 0.3072 -0.1175 0.057 Uiso 1 1 calc R . . H10B H 0.9381 0.2688 -0.1363 0.057 Uiso 1 1 calc R . . C11A C 0.96862(12) 0.31040(6) 0.02248(16) 0.0452(5) Uani 1 1 d . . . C12A C 1.02379(15) 0.34577(8) -0.0513(2) 0.0670(6) Uani 1 1 d . . . H12A H 1.0747 0.3564 0.0049 0.08 Uiso 1 1 calc R . . H12B H 1.0498 0.3307 -0.126 0.08 Uiso 1 1 calc R . . C13A C 0.9695(2) 0.38689(10) -0.0981(4) 0.0967(10) Uani 1 1 d U . . C14A C 0.9257(2) 0.41034(10) 0.0139(4) 0.1223(13) Uani 1 1 d U . . H14A H 0.8882 0.436 -0.0183 0.147 Uiso 1 1 calc R . . H14B H 0.9734 0.4227 0.0729 0.147 Uiso 1 1 calc R . . C15A C 0.86510(19) 0.37631(11) 0.0886(3) 0.0997(10) Uani 1 1 d . . . H15A H 0.8414 0.3918 0.1643 0.12 Uiso 1 1 calc R . . H15B H 0.8129 0.367 0.0328 0.12 Uiso 1 1 calc R . . C16A C 0.91943(15) 0.33337(8) 0.1327(2) 0.0664(6) Uani 1 1 d . . . H16A H 0.9645 0.3422 0.2005 0.08 Uiso 1 1 calc R . . H16B H 0.8775 0.3113 0.1699 0.08 Uiso 1 1 calc R . . C17A C 0.80672(15) 0.04000(7) 0.0571(2) 0.0587(5) Uani 1 1 d . . . C18A C 0.8671(2) 0.02354(9) 0.1730(3) 0.1092(11) Uani 1 1 d . . . H18A H 0.9228 0.0414 0.1782 0.164 Uiso 1 1 calc R . . H18B H 0.882 -0.0086 0.1618 0.164 Uiso 1 1 calc R . . H18C H 0.8343 0.0274 0.2518 0.164 Uiso 1 1 calc R . . C19A C 0.8586(2) 0.03314(9) -0.0681(3) 0.0934(9) Uani 1 1 d . . . H19A H 0.824 0.0467 -0.14 0.14 Uiso 1 1 calc R . . H19B H 0.8666 0.0006 -0.0836 0.14 Uiso 1 1 calc R . . H19C H 0.9179 0.0478 -0.0594 0.14 Uiso 1 1 calc R . . C20A C 0.71965(19) 0.01015(8) 0.0443(3) 0.0883(8) Uani 1 1 d . . . H20A H 0.689 0.0102 0.1255 0.133 Uiso 1 1 calc R . . H20B H 0.7363 -0.021 0.0224 0.133 Uiso 1 1 calc R . . H20C H 0.6791 0.0225 -0.0231 0.133 Uiso 1 1 calc R . . C21A C 0.60652(13) 0.16094(7) 0.27562(17) 0.0498(5) Uani 1 1 d . . . C22A C 0.64021(15) 0.19046(8) 0.39234(18) 0.0636(6) Uani 1 1 d . . . H22A H 0.6859 0.1736 0.443 0.095 Uiso 1 1 calc R . . H22B H 0.5891 0.1976 0.4455 0.095 Uiso 1 1 calc R . . H22C H 0.6667 0.2187 0.3614 0.095 Uiso 1 1 calc R . . C23A C 0.53146(14) 0.18776(9) 0.1978(2) 0.0662(6) Uani 1 1 d . . . H23A H 0.558 0.2148 0.1599 0.099 Uiso 1 1 calc R . . H23B H 0.4839 0.1969 0.255 0.099 Uiso 1 1 calc R . . H23C H 0.5055 0.1683 0.1299 0.099 Uiso 1 1 calc R . . C24A C 0.56274(17) 0.11740(8) 0.3292(2) 0.0778(7) Uani 1 1 d . . . H24A H 0.5402 0.0984 0.2581 0.117 Uiso 1 1 calc R . . H24B H 0.5125 0.1258 0.3825 0.117 Uiso 1 1 calc R . . H24C H 0.608 0.1005 0.3807 0.117 Uiso 1 1 calc R . . N9A N 0.84553(10) 0.25170(5) -0.00567(13) 0.0462(4) Uani 1 1 d . . . O1A O 0.71678(10) 0.22939(5) 0.14882(13) 0.0555(4) Uani 1 1 d . . . O2A O 1.03127(10) 0.27740(5) 0.08278(15) 0.0605(4) Uani 1 1 d . . . C2B C 0.32330(12) 0.13900(7) 0.47365(17) 0.0464(5) Uani 1 1 d . . . C3B C 0.34695(12) 0.09470(7) 0.52179(17) 0.0477(5) Uani 1 1 d . . . C4B C 0.41508(13) 0.09309(7) 0.62072(17) 0.0510(5) Uani 1 1 d . . . H4B H 0.431 0.0642 0.6546 0.061 Uiso 1 1 calc R . . C5B C 0.46125(13) 0.13156(7) 0.67283(16) 0.0493(5) Uani 1 1 d . . . C6B C 0.43799(13) 0.17397(7) 0.62033(16) 0.0492(5) Uani 1 1 d . . . H6B H 0.4686 0.2003 0.6511 0.059 Uiso 1 1 calc R . . C7B C 0.36952(12) 0.17838(7) 0.52180(16) 0.0439(4) Uani 1 1 d . . . C8B C 0.34963(13) 0.22415(7) 0.46853(17) 0.0470(5) Uani 1 1 d . . . H8B H 0.3858 0.2489 0.4976 0.056 Uiso 1 1 calc R . . C10B C 0.27174(14) 0.27889(7) 0.33438(19) 0.0528(5) Uani 1 1 d . . . H10C H 0.264 0.2777 0.2401 0.063 Uiso 1 1 calc R . . H10D H 0.3272 0.2965 0.3553 0.063 Uiso 1 1 calc R . . C11B C 0.18938(12) 0.30431(6) 0.38908(16) 0.0435(4) Uani 1 1 d . . . C12B C 0.18186(16) 0.35197(7) 0.3255(2) 0.0630(6) Uani 1 1 d . . . H12C H 0.2411 0.3674 0.3347 0.076 Uiso 1 1 calc R . . H12D H 0.1673 0.3482 0.2331 0.076 Uiso 1 1 calc R . . C13B C 0.10871(19) 0.38228(8) 0.3845(2) 0.0811(7) Uani 1 1 d . . . H13E H 0.1096 0.4126 0.3442 0.097 Uiso 1 1 calc R . . H13F H 0.0484 0.3688 0.3663 0.097 Uiso 1 1 calc R . . C14B C 0.1243(2) 0.38739(9) 0.5300(3) 0.0871(8) Uani 1 1 d . . . H14E H 0.0752 0.4059 0.5652 0.104 Uiso 1 1 calc R . . H14F H 0.1823 0.4031 0.5488 0.104 Uiso 1 1 calc R . . C15B C 0.12601(16) 0.34002(9) 0.5935(2) 0.0717(7) Uani 1 1 d . . . H15E H 0.0661 0.3255 0.5805 0.086 Uiso 1 1 calc R . . H15F H 0.1382 0.3435 0.6866 0.086 Uiso 1 1 calc R . . C16B C 0.19937(14) 0.30900(7) 0.53716(17) 0.0536(5) Uani 1 1 d . . . H16C H 0.1955 0.2785 0.5762 0.064 Uiso 1 1 calc R . . H16D H 0.2598 0.3216 0.5601 0.064 Uiso 1 1 calc R . . C17B C 0.53591(15) 0.12521(8) 0.78129(18) 0.0620(6) Uani 1 1 d . . . C18B C 0.4933(2) 0.10162(10) 0.8976(2) 0.0917(9) Uani 1 1 d . . . H18D H 0.4707 0.0716 0.872 0.138 Uiso 1 1 calc R . . H18E H 0.4433 0.1201 0.9272 0.138 Uiso 1 1 calc R . . H18F H 0.5392 0.0983 0.9669 0.138 Uiso 1 1 calc R . . C19B C 0.61361(18) 0.09499(11) 0.7298(3) 0.0988(10) Uani 1 1 d . . . H19D H 0.6367 0.1087 0.6523 0.148 Uiso 1 1 calc R . . H19E H 0.5901 0.0646 0.7098 0.148 Uiso 1 1 calc R . . H19F H 0.6626 0.0927 0.795 0.148 Uiso 1 1 calc R . . C20B C 0.57706(19) 0.17145(10) 0.8266(2) 0.0883(8) Uani 1 1 d . . . H20D H 0.5288 0.1913 0.8553 0.132 Uiso 1 1 calc R . . H20E H 0.6072 0.1859 0.7555 0.132 Uiso 1 1 calc R . . H20F H 0.621 0.1662 0.8973 0.132 Uiso 1 1 calc R . . C21B C 0.30147(14) 0.05050(7) 0.4662(2) 0.0607(6) Uani 1 1 d . . . C22B C 0.19713(17) 0.05215(10) 0.4863(4) 0.1020(10) Uani 1 1 d . . . H22D H 0.1863 0.0567 0.5771 0.153 Uiso 1 1 calc R . . H22E H 0.1696 0.0235 0.4576 0.153 Uiso 1 1 calc R . . H22F H 0.1703 0.0773 0.4366 0.153 Uiso 1 1 calc R . . C23B C 0.3203(2) 0.04669(9) 0.3198(2) 0.0928(9) Uani 1 1 d . . . H23D H 0.3855 0.0447 0.3086 0.139 Uiso 1 1 calc R . . H23E H 0.2962 0.0735 0.2752 0.139 Uiso 1 1 calc R . . H23F H 0.2908 0.0194 0.2846 0.139 Uiso 1 1 calc R . . C24B C 0.33885(17) 0.00663(8) 0.5323(3) 0.0809(7) Uani 1 1 d . . . H24D H 0.3064 -0.0198 0.4973 0.121 Uiso 1 1 calc R . . H24E H 0.3303 0.0085 0.6244 0.121 Uiso 1 1 calc R . . H24F H 0.4034 0.0036 0.5166 0.121 Uiso 1 1 calc R . . N9B N 0.28449(11) 0.23188(6) 0.38336(15) 0.0508(4) Uani 1 1 d . . . O1B O 0.25694(10) 0.14355(6) 0.37808(14) 0.0640(4) Uani 1 1 d . . . O2B O 0.10593(9) 0.27838(4) 0.36354(13) 0.0499(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2A 0.0427(11) 0.0399(11) 0.0438(9) -0.0021(8) -0.0002(8) 0.0026(8) C3A 0.0432(11) 0.0460(11) 0.0426(9) -0.0008(8) 0.0021(8) 0.0024(9) C4A 0.0510(12) 0.0453(12) 0.0483(10) 0.0012(9) 0.0061(9) -0.0035(9) C5A 0.0511(12) 0.0424(11) 0.0490(10) -0.0036(8) 0.0025(9) 0.0012(9) C6A 0.0453(11) 0.0502(12) 0.0520(10) -0.0058(9) 0.0090(8) 0.0027(9) C7A 0.0440(11) 0.0420(11) 0.0428(9) -0.0032(8) 0.0026(8) 0.0002(8) C8A 0.0439(11) 0.0494(12) 0.0442(10) -0.0029(9) 0.0038(8) 0.0005(9) C10A 0.0505(12) 0.0508(12) 0.0420(9) 0.0041(8) 0.0053(8) -0.0009(9) C11A 0.0425(11) 0.0464(11) 0.0467(10) 0.0062(8) -0.0004(8) 0.0017(9) C12A 0.0543(13) 0.0695(15) 0.0766(14) 0.0188(12) -0.0032(11) -0.0149(11) C13A 0.097(2) 0.0590(17) 0.131(3) 0.0352(18) -0.033(2) -0.0228(17) C14A 0.110(3) 0.0551(18) 0.197(4) -0.003(2) -0.059(2) 0.0041(18) C15A 0.0696(18) 0.100(2) 0.128(2) -0.0553(19) -0.0147(16) 0.0284(17) C16A 0.0586(14) 0.0786(16) 0.0619(12) -0.0217(11) 0.0036(10) -0.0043(12) C17A 0.0668(14) 0.0413(12) 0.0683(12) -0.0070(10) 0.0058(10) 0.0058(10) C18A 0.145(3) 0.0550(16) 0.123(2) -0.0069(15) -0.046(2) 0.0283(17) C19A 0.114(2) 0.0541(15) 0.115(2) -0.0194(14) 0.0472(17) 0.0071(15) C20A 0.098(2) 0.0495(14) 0.118(2) -0.0217(14) 0.0203(16) -0.0117(14) C21A 0.0440(11) 0.0553(12) 0.0505(10) -0.0054(9) 0.0090(8) -0.0009(9) C22A 0.0601(14) 0.0823(16) 0.0489(11) -0.0090(11) 0.0074(9) 0.0031(12) C23A 0.0474(13) 0.0851(17) 0.0662(13) -0.0087(12) 0.0044(10) 0.0102(11) C24A 0.0789(17) 0.0685(16) 0.0889(16) -0.0032(13) 0.0399(13) -0.0094(13) N9A 0.0461(9) 0.0449(10) 0.0479(8) 0.0029(7) 0.0046(7) -0.0022(7) O1A 0.0603(9) 0.0408(8) 0.0667(8) -0.0014(7) 0.0191(7) 0.0036(7) O2A 0.0625(10) 0.0603(9) 0.0577(8) 0.0074(7) -0.0076(7) 0.0105(7) C2B 0.0376(10) 0.0549(12) 0.0465(10) -0.0039(9) -0.0005(8) 0.0049(9) C3B 0.0430(11) 0.0502(12) 0.0498(10) -0.0044(9) 0.0023(8) 0.0052(9) C4B 0.0528(12) 0.0525(12) 0.0479(10) -0.0009(9) 0.0030(9) 0.0119(10) C5B 0.0470(11) 0.0591(13) 0.0416(9) -0.0075(9) 0.0006(8) 0.0078(10) C6B 0.0457(11) 0.0561(12) 0.0459(10) -0.0114(9) 0.0024(8) 0.0011(9) C7B 0.0380(10) 0.0497(12) 0.0441(9) -0.0050(8) 0.0047(8) 0.0069(8) C8B 0.0410(11) 0.0506(12) 0.0501(10) -0.0047(9) 0.0089(8) -0.0002(9) C10B 0.0545(12) 0.0510(12) 0.0532(11) 0.0089(9) 0.0052(9) -0.0045(10) C11B 0.0447(11) 0.0417(11) 0.0439(10) 0.0062(8) -0.0025(8) -0.0068(8) C12B 0.0729(15) 0.0483(13) 0.0669(13) 0.0142(10) -0.0115(11) -0.0086(11) C13B 0.097(2) 0.0444(13) 0.1001(18) -0.0008(12) -0.0209(15) 0.0089(13) C14B 0.0937(19) 0.0640(17) 0.1017(19) -0.0291(15) -0.0190(15) 0.0115(14) C15B 0.0694(16) 0.0901(19) 0.0551(12) -0.0200(12) -0.0058(11) 0.0074(13) C16B 0.0546(12) 0.0600(13) 0.0457(10) 0.0007(9) -0.0050(9) -0.0003(10) C17B 0.0594(13) 0.0769(16) 0.0488(11) -0.0023(11) -0.0111(10) 0.0098(12) C18B 0.112(2) 0.107(2) 0.0547(13) 0.0094(14) -0.0188(13) -0.0059(17) C19B 0.0721(18) 0.134(3) 0.0882(17) -0.0106(17) -0.0224(14) 0.0408(18) C20B 0.0850(18) 0.100(2) 0.0771(15) 0.0010(15) -0.0352(13) -0.0107(16) C21B 0.0550(14) 0.0498(13) 0.0766(14) -0.0049(10) -0.0069(11) 0.0017(10) C22B 0.0552(16) 0.0643(17) 0.186(3) 0.0002(18) -0.0033(17) -0.0085(13) C23B 0.129(2) 0.0715(17) 0.0762(16) -0.0237(13) -0.0160(15) -0.0045(17) C24B 0.0849(18) 0.0548(15) 0.1023(18) -0.0034(13) -0.0051(14) 0.0033(13) N9B 0.0482(10) 0.0496(10) 0.0548(9) 0.0021(7) 0.0035(8) 0.0050(8) O1B 0.0586(9) 0.0560(10) 0.0753(9) 0.0011(7) -0.0240(7) 0.0000(7) O2B 0.0522(8) 0.0502(8) 0.0470(8) 0.0040(6) -0.0042(6) -0.0090(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2A O1A 1.349(2) . ? C2A C7A 1.403(2) . ? C2A C3A 1.408(3) . ? C3A C4A 1.388(3) . ? C3A C21A 1.539(2) . ? C4A C5A 1.401(3) . ? C4A H4A 0.93 . ? C5A C6A 1.374(3) . ? C5A C17A 1.537(3) . ? C6A C7A 1.395(3) . ? C6A H6A 0.93 . ? C7A C8A 1.457(3) . ? C8A N9A 1.268(2) . ? C8A H8A 0.93 . ? C10A N9A 1.454(2) . ? C10A C11A 1.525(3) . ? C10A H10A 0.97 . ? C10A H10B 0.97 . ? C11A O2A 1.441(2) . ? C11A C16A 1.513(3) . ? C11A C12A 1.518(3) . ? C12A C13A 1.494(4) . ? C12A H12A 0.97 . ? C12A H12B 0.97 . ? C13A C14A 1.496(5) . ? C13A H13A 1.02(3) . ? C13A H13B 1.00(3) . ? C14A C15A 1.543(5) . ? C14A H14A 0.97 . ? C14A H14B 0.97 . ? C15A C16A 1.529(4) . ? C15A H15A 0.97 . ? C15A H15B 0.97 . ? C16A H16A 0.97 . ? C16A H16B 0.97 . ? C17A C18A 1.526(3) . ? C17A C19A 1.527(3) . ? C17A C20A 1.531(3) . ? C18A H18A 0.96 . ? C18A H18B 0.96 . ? C18A H18C 0.96 . ? C19A H19A 0.96 . ? C19A H19B 0.96 . ? C19A H19C 0.96 . ? C20A H20A 0.96 . ? C20A H20B 0.96 . ? C20A H20C 0.96 . ? C21A C24A 1.521(3) . ? C21A C22A 1.535(3) . ? C21A C23A 1.535(3) . ? C22A H22A 0.96 . ? C22A H22B 0.96 . ? C22A H22C 0.96 . ? C23A H23A 0.96 . ? C23A H23B 0.96 . ? C23A H23C 0.96 . ? C24A H24A 0.96 . ? C24A H24B 0.96 . ? C24A H24C 0.96 . ? O1A H1A 0.94(3) . ? O2A H2A 0.88(3) . ? C2B O1B 1.354(2) . ? C2B C7B 1.401(3) . ? C2B C3B 1.409(3) . ? C3B C4B 1.390(2) . ? C3B C21B 1.537(3) . ? C4B C5B 1.393(3) . ? C4B H4B 0.93 . ? C5B C6B 1.375(3) . ? C5B C17B 1.534(3) . ? C6B C7B 1.396(2) . ? C6B H6B 0.93 . ? C7B C8B 1.455(3) . ? C8B N9B 1.282(2) . ? C8B H8B 0.93 . ? C10B N9B 1.457(2) . ? C10B C11B 1.528(3) . ? C10B H10C 0.97 . ? C10B H10D 0.97 . ? C11B O2B 1.439(2) . ? C11B C12B 1.525(3) . ? C11B C16B 1.527(2) . ? C12B C13B 1.519(3) . ? C12B H12C 0.97 . ? C12B H12D 0.97 . ? C13B C14B 1.509(4) . ? C13B H13E 0.97 . ? C13B H13F 0.97 . ? C14B C15B 1.515(4) . ? C14B H14E 0.97 . ? C14B H14F 0.97 . ? C15B C16B 1.522(3) . ? C15B H15E 0.97 . ? C15B H15F 0.97 . ? C16B H16C 0.97 . ? C16B H16D 0.97 . ? C17B C18B 1.525(3) . ? C17B C20B 1.528(3) . ? C17B C19B 1.536(3) . ? C18B H18D 0.96 . ? C18B H18E 0.96 . ? C18B H18F 0.96 . ? C19B H19D 0.96 . ? C19B H19E 0.96 . ? C19B H19F 0.96 . ? C20B H20D 0.96 . ? C20B H20E 0.96 . ? C20B H20F 0.96 . ? C21B C24B 1.527(3) . ? C21B C22B 1.537(3) . ? C21B C23B 1.540(3) . ? C22B H22D 0.96 . ? C22B H22E 0.96 . ? C22B H22F 0.96 . ? C23B H23D 0.96 . ? C23B H23E 0.96 . ? C23B H23F 0.96 . ? C24B H24D 0.96 . ? C24B H24E 0.96 . ? C24B H24F 0.96 . ? O1B H1B 1.00(3) . ? O2B H2B 0.87(3) . ? 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 O1A C2A C7A 119.99(16) . . ? O1A C2A C3A 119.85(16) . . ? C7A C2A C3A 120.15(17) . . ? C4A C3A C2A 116.59(17) . . ? C4A C3A C21A 122.01(17) . . ? C2A C3A C21A 121.39(17) . . ? C3A C4A C5A 125.04(17) . . ? C3A C4A H4A 117.5 . . ? C5A C4A H4A 117.5 . . ? C6A C5A C4A 116.22(17) . . ? C6A C5A C17A 122.43(17) . . ? C4A C5A C17A 121.31(17) . . ? C5A C6A C7A 122.04(17) . . ? C5A C6A H6A 119 . . ? C7A C6A H6A 119 . . ? C6A C7A C2A 119.94(17) . . ? C6A C7A C8A 119.01(16) . . ? C2A C7A C8A 121.03(17) . . ? N9A C8A C7A 122.87(17) . . ? N9A C8A H8A 118.6 . . ? C7A C8A H8A 118.6 . . ? N9A C10A C11A 112.15(14) . . ? N9A C10A H10A 109.2 . . ? C11A C10A H10A 109.2 . . ? N9A C10A H10B 109.2 . . ? C11A C10A H10B 109.2 . . ? H10A C10A H10B 107.9 . . ? O2A C11A C16A 106.07(15) . . ? O2A C11A C12A 108.87(15) . . ? C16A C11A C12A 110.53(18) . . ? O2A C11A C10A 108.87(15) . . ? C16A C11A C10A 112.60(16) . . ? C12A C11A C10A 109.76(15) . . ? C13A C12A C11A 114.4(2) . . ? C13A C12A H12A 108.7 . . ? C11A C12A H12A 108.7 . . ? C13A C12A H12B 108.7 . . ? C11A C12A H12B 108.7 . . ? H12A C12A H12B 107.6 . . ? C12A C13A C14A 110.3(3) . . ? C12A C13A H13A 110.4(15) . . ? C14A C13A H13A 110.1(15) . . ? C12A C13A H13B 109.1(16) . . ? C14A C13A H13B 108.2(16) . . ? H13A C13A H13B 109(2) . . ? C13A C14A C15A 111.1(2) . . ? C13A C14A H14A 109.4 . . ? C15A C14A H14A 109.4 . . ? C13A C14A H14B 109.4 . . ? C15A C14A H14B 109.4 . . ? H14A C14A H14B 108 . . ? C16A C15A C14A 111.5(2) . . ? C16A C15A H15A 109.3 . . ? C14A C15A H15A 109.3 . . ? C16A C15A H15B 109.3 . . ? C14A C15A H15B 109.3 . . ? H15A C15A H15B 108 . . ? C11A C16A C15A 112.77(19) . . ? C11A C16A H16A 109 . . ? C15A C16A H16A 109 . . ? C11A C16A H16B 109 . . ? C15A C16A H16B 109 . . ? H16A C16A H16B 107.8 . . ? C18A C17A C19A 109.2(2) . . ? C18A C17A C20A 109.8(2) . . ? C19A C17A C20A 106.67(19) . . ? C18A C17A C5A 108.30(17) . . ? C19A C17A C5A 111.64(17) . . ? C20A C17A C5A 111.23(18) . . ? C17A C18A H18A 109.5 . . ? C17A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C17A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C17A C19A H19A 109.5 . . ? C17A C19A H19B 109.5 . . ? H19A C19A H19B 109.5 . . ? C17A C19A H19C 109.5 . . ? H19A C19A H19C 109.5 . . ? H19B C19A H19C 109.5 . . ? C17A C20A H20A 109.5 . . ? C17A C20A H20B 109.5 . . ? H20A C20A H20B 109.5 . . ? C17A C20A H20C 109.5 . . ? H20A C20A H20C 109.5 . . ? H20B C20A H20C 109.5 . . ? C24A C21A C22A 107.60(17) . . ? C24A C21A C23A 107.89(18) . . ? C22A C21A C23A 108.91(17) . . ? C24A C21A C3A 111.72(17) . . ? C22A C21A C3A 110.60(15) . . ? C23A C21A C3A 110.03(15) . . ? C21A C22A H22A 109.5 . . ? C21A C22A H22B 109.5 . . ? H22A C22A H22B 109.5 . . ? C21A C22A H22C 109.5 . . ? H22A C22A H22C 109.5 . . ? H22B C22A H22C 109.5 . . ? C21A C23A H23A 109.5 . . ? C21A C23A H23B 109.5 . . ? H23A C23A H23B 109.5 . . ? C21A C23A H23C 109.5 . . ? H23A C23A H23C 109.5 . . ? H23B C23A H23C 109.5 . . ? C21A C24A H24A 109.5 . . ? C21A C24A H24B 109.5 . . ? H24A C24A H24B 109.5 . . ? C21A C24A H24C 109.5 . . ? H24A C24A H24C 109.5 . . ? H24B C24A H24C 109.5 . . ? C8A N9A C10A 118.88(16) . . ? C2A O1A H1A 107.5(14) . . ? C11A O2A H2A 102(2) . . ? O1B C2B C7B 119.62(17) . . ? O1B C2B C3B 119.93(17) . . ? C7B C2B C3B 120.44(16) . . ? C4B C3B C2B 116.30(18) . . ? C4B C3B C21B 121.78(18) . . ? C2B C3B C21B 121.91(16) . . ? C3B C4B C5B 124.86(18) . . ? C3B C4B H4B 117.6 . . ? C5B C4B H4B 117.6 . . ? C6B C5B C4B 116.92(17) . . ? C6B C5B C17B 123.13(18) . . ? C4B C5B C17B 119.93(18) . . ? C5B C6B C7B 121.48(18) . . ? C5B C6B H6B 119.3 . . ? C7B C6B H6B 119.3 . . ? C6B C7B C2B 119.96(18) . . ? C6B C7B C8B 118.71(18) . . ? C2B C7B C8B 121.31(16) . . ? N9B C8B C7B 123.00(18) . . ? N9B C8B H8B 118.5 . . ? C7B C8B H8B 118.5 . . ? N9B C10B C11B 114.33(15) . . ? N9B C10B H10C 108.7 . . ? C11B C10B H10C 108.7 . . ? N9B C10B H10D 108.7 . . ? C11B C10B H10D 108.7 . . ? H10C C10B H10D 107.6 . . ? O2B C11B C12B 110.23(15) . . ? O2B C11B C16B 105.94(15) . . ? C12B C11B C16B 110.37(16) . . ? O2B C11B C10B 110.33(15) . . ? C12B C11B C10B 108.72(15) . . ? C16B C11B C10B 111.25(15) . . ? C13B C12B C11B 112.90(18) . . ? C13B C12B H12C 109 . . ? C11B C12B H12C 109 . . ? C13B C12B H12D 109 . . ? C11B C12B H12D 109 . . ? H12C C12B H12D 107.8 . . ? C14B C13B C12B 111.7(2) . . ? C14B C13B H13E 109.3 . . ? C12B C13B H13E 109.3 . . ? C14B C13B H13F 109.3 . . ? C12B C13B H13F 109.3 . . ? H13E C13B H13F 107.9 . . ? C13B C14B C15B 109.65(19) . . ? C13B C14B H14E 109.7 . . ? C15B C14B H14E 109.7 . . ? C13B C14B H14F 109.7 . . ? C15B C14B H14F 109.7 . . ? H14E C14B H14F 108.2 . . ? C14B C15B C16B 111.6(2) . . ? C14B C15B H15E 109.3 . . ? C16B C15B H15E 109.3 . . ? C14B C15B H15F 109.3 . . ? C16B C15B H15F 109.3 . . ? H15E C15B H15F 108 . . ? C15B C16B C11B 112.89(16) . . ? C15B C16B H16C 109 . . ? C11B C16B H16C 109 . . ? C15B C16B H16D 109 . . ? C11B C16B H16D 109 . . ? H16C C16B H16D 107.8 . . ? C18B C17B C20B 108.51(19) . . ? C18B C17B C5B 108.98(19) . . ? C20B C17B C5B 111.91(18) . . ? C18B C17B C19B 109.9(2) . . ? C20B C17B C19B 108.5(2) . . ? C5B C17B C19B 109.00(16) . . ? C17B C18B H18D 109.5 . . ? C17B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C17B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C17B C19B H19D 109.5 . . ? C17B C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? C17B C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 109.5 . . ? C17B C20B H20D 109.5 . . ? C17B C20B H20E 109.5 . . ? H20D C20B H20E 109.5 . . ? C17B C20B H20F 109.5 . . ? H20D C20B H20F 109.5 . . ? H20E C20B H20F 109.5 . . ? C24B C21B C22B 107.5(2) . . ? C24B C21B C3B 112.58(17) . . ? C22B C21B C3B 109.62(18) . . ? C24B C21B C23B 107.51(19) . . ? C22B C21B C23B 110.2(2) . . ? C3B C21B C23B 109.39(18) . . ? C21B C22B H22D 109.5 . . ? C21B C22B H22E 109.5 . . ? H22D C22B H22E 109.5 . . ? C21B C22B H22F 109.5 . . ? H22D C22B H22F 109.5 . . ? H22E C22B H22F 109.5 . . ? C21B C23B H23D 109.5 . . ? C21B C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? C21B C23B H23F 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? C21B C24B H24D 109.5 . . ? C21B C24B H24E 109.5 . . ? H24D C24B H24E 109.5 . . ? C21B C24B H24F 109.5 . . ? H24D C24B H24F 109.5 . . ? H24E C24B H24F 109.5 . . ? C8B N9B C10B 118.54(17) . . ? C2B O1B H1B 103.3(13) . . ? C11B O2B H2B 108.5(17) . . ? 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 O1A C2A C3A C4A 179.76(15) . . . . ? C7A C2A C3A C4A 0.1(2) . . . . ? O1A C2A C3A C21A 0.8(3) . . . . ? C7A C2A C3A C21A -178.77(15) . . . . ? C2A C3A C4A C5A -1.0(3) . . . . ? C21A C3A C4A C5A 177.89(16) . . . . ? C3A C4A C5A C6A 0.9(3) . . . . ? C3A C4A C5A C17A 178.96(17) . . . . ? C4A C5A C6A C7A 0.2(3) . . . . ? C17A C5A C6A C7A -177.91(17) . . . . ? C5A C6A C7A C2A -1.0(3) . . . . ? C5A C6A C7A C8A -179.04(16) . . . . ? O1A C2A C7A C6A -178.82(16) . . . . ? C3A C2A C7A C6A 0.8(3) . . . . ? O1A C2A C7A C8A -0.8(3) . . . . ? C3A C2A C7A C8A 178.83(16) . . . . ? C6A C7A C8A N9A 177.75(17) . . . . ? C2A C7A C8A N9A -0.3(3) . . . . ? N9A C10A C11A O2A 63.04(19) . . . . ? N9A C10A C11A C16A -54.3(2) . . . . ? N9A C10A C11A C12A -177.88(16) . . . . ? O2A C11A C12A C13A -169.3(2) . . . . ? C16A C11A C12A C13A -53.2(3) . . . . ? C10A C11A C12A C13A 71.6(3) . . . . ? C11A C12A C13A C14A 56.7(3) . . . . ? C12A C13A C14A C15A -56.2(3) . . . . ? C13A C14A C15A C16A 54.8(3) . . . . ? O2A C11A C16A C15A 168.00(19) . . . . ? C12A C11A C16A C15A 50.1(2) . . . . ? C10A C11A C16A C15A -73.0(2) . . . . ? C14A C15A C16A C11A -52.0(3) . . . . ? C6A C5A C17A C18A 97.9(2) . . . . ? C4A C5A C17A C18A -80.1(3) . . . . ? C6A C5A C17A C19A -22.3(3) . . . . ? C4A C5A C17A C19A 159.69(19) . . . . ? C6A C5A C17A C20A -141.4(2) . . . . ? C4A C5A C17A C20A 40.7(3) . . . . ? C4A C3A C21A C24A 1.4(3) . . . . ? C2A C3A C21A C24A -179.76(17) . . . . ? C4A C3A C21A C22A 121.21(19) . . . . ? C2A C3A C21A C22A -59.9(2) . . . . ? C4A C3A C21A C23A -118.4(2) . . . . ? C2A C3A C21A C23A 60.4(2) . . . . ? C7A C8A N9A C10A 178.66(15) . . . . ? C11A C10A N9A C8A -107.34(19) . . . . ? O1B C2B C3B C4B -179.39(16) . . . . ? C7B C2B C3B C4B 2.1(3) . . . . ? O1B C2B C3B C21B 1.8(3) . . . . ? C7B C2B C3B C21B -176.62(16) . . . . ? C2B C3B C4B C5B -0.9(3) . . . . ? C21B C3B C4B C5B 177.87(18) . . . . ? C3B C4B C5B C6B -1.0(3) . . . . ? C3B C4B C5B C17B -179.47(17) . . . . ? C4B C5B C6B C7B 1.7(3) . . . . ? C17B C5B C6B C7B -179.90(17) . . . . ? C5B C6B C7B C2B -0.5(3) . . . . ? C5B C6B C7B C8B -178.69(16) . . . . ? O1B C2B C7B C6B 179.99(16) . . . . ? C3B C2B C7B C6B -1.5(3) . . . . ? O1B C2B C7B C8B -1.8(3) . . . . ? C3B C2B C7B C8B 176.64(16) . . . . ? C6B C7B C8B N9B -175.88(16) . . . . ? C2B C7B C8B N9B 5.9(3) . . . . ? N9B C10B C11B O2B -56.6(2) . . . . ? N9B C10B C11B C12B -177.59(16) . . . . ? N9B C10B C11B C16B 60.7(2) . . . . ? O2B C11B C12B C13B 65.5(2) . . . . ? C16B C11B C12B C13B -51.1(2) . . . . ? C10B C11B C12B C13B -173.40(17) . . . . ? C11B C12B C13B C14B 55.5(3) . . . . ? C12B C13B C14B C15B -57.2(3) . . . . ? C13B C14B C15B C16B 57.0(3) . . . . ? C14B C15B C16B C11B -55.1(2) . . . . ? O2B C11B C16B C15B -68.3(2) . . . . ? C12B C11B C16B C15B 51.0(2) . . . . ? C10B C11B C16B C15B 171.75(18) . . . . ? C6B C5B C17B C18B 122.6(2) . . . . ? C4B C5B C17B C18B -59.1(2) . . . . ? C6B C5B C17B C20B 2.5(3) . . . . ? C4B C5B C17B C20B -179.09(19) . . . . ? C6B C5B C17B C19B -117.5(2) . . . . ? C4B C5B C17B C19B 60.8(3) . . . . ? C4B C3B C21B C24B 0.6(3) . . . . ? C2B C3B C21B C24B 179.28(18) . . . . ? C4B C3B C21B C22B 120.2(2) . . . . ? C2B C3B C21B C22B -61.1(3) . . . . ? C4B C3B C21B C23B -118.9(2) . . . . ? C2B C3B C21B C23B 59.8(2) . . . . ? C7B C8B N9B C10B -178.70(15) . . . . ? C11B C10B N9B C8B -104.70(19) . . . . ? _chemical_name_common ;2,4-di-tert-butyl-6-((1-hydroxy-cyclohexylmethylimino)- methyl)-phenol ; #===END #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_Compound4 _database_code_depnum_ccdc_archive 'CCDC 712149' #TrackingRef '- cifs 1-8_(R2).cif' _audit_creation_date 2010-07-21T00:03:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-{[(1-hydroxycyclohexyl)methylimino]methyl} phenol ; _chemical_formula_moiety 'C14 H19 N1 O2' _chemical_formula_sum 'C14 H19 N1 O2' _chemical_formula_weight 233.3 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_Int_Tables_number 29 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 9.0270(18) _cell_length_b 6.2300(12) _cell_length_c 22.198(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1248.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5811 _cell_measurement_theta_min 0.783 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.589981E-1 _diffrn_orient_matrix_ub_12 0.984312E-1 _diffrn_orient_matrix_ub_13 0.123739E-1 _diffrn_orient_matrix_ub_21 -0.897906E-1 _diffrn_orient_matrix_ub_22 -0.27384E-2 _diffrn_orient_matrix_ub_23 0.373237E-1 _diffrn_orient_matrix_ub_31 0.11925 _diffrn_orient_matrix_ub_32 -0.507598E-1 _diffrn_orient_matrix_ub_33 0.219813E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_unetI/netI 0.0535 _diffrn_reflns_number 4269 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.26 _diffrn_reflns_theta_full 27.26 _diffrn_measured_fraction_theta_full 0.976 _diffrn_measured_fraction_theta_max 0.976 _reflns_number_total 1399 _reflns_number_gt 1051 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.35(3) _refine_ls_number_reflns 1399 _refine_ls_number_parameters 163 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.165 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_abs_structure_details ; The light-atom structure prevented a useful absolute structure parameter. The Friedel-pairs reflections were merged in the refinement by using MERG4. Flack H D (1983), Acta Cryst. A39, 876-881. ; _refine_ls_abs_structure_Flack -10(10) _refine_diff_density_max 0.276 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.110 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.1589(4) 0.8707(6) 0.49098(17) 0.0442(8) Uani 1 1 d . . . C3 C 0.0623(4) 1.0094(6) 0.5227(2) 0.0558(10) Uani 1 1 d . . . H3 H 0.0388 1.1423 0.5062 0.067 Uiso 1 1 calc R . . C4 C 0.0027(5) 0.9527(7) 0.5770(2) 0.0668(11) Uani 1 1 d . . . H4 H -0.0602 1.0478 0.5967 0.08 Uiso 1 1 calc R . . C5 C 0.0347(5) 0.7545(8) 0.6035(2) 0.0706(12) Uani 1 1 d . . . H5 H -0.0059 0.7178 0.6406 0.085 Uiso 1 1 calc R . . C6 C 0.1260(5) 0.6159(7) 0.57401(19) 0.0611(10) Uani 1 1 d . . . H6 H 0.1477 0.484 0.5916 0.073 Uiso 1 1 calc R . . C7 C 0.1884(4) 0.6668(6) 0.51781(17) 0.0452(8) Uani 1 1 d . . . C8 C 0.2743(4) 0.5124(5) 0.48665(17) 0.0454(8) Uani 1 1 d . . . H8 H 0.2891 0.3797 0.5049 0.054 Uiso 1 1 calc R . . C10 C 0.4093(4) 0.3827(6) 0.39995(18) 0.0487(9) Uani 1 1 d . . . H10A H 0.4247 0.2571 0.425 0.058 Uiso 1 1 calc R . . H10B H 0.5058 0.4372 0.3884 0.058 Uiso 1 1 calc R . . C11 C 0.3252(3) 0.3163(5) 0.34343(17) 0.0397(8) Uani 1 1 d . . . C12 C 0.4104(4) 0.1301(5) 0.31436(18) 0.0483(9) Uani 1 1 d . . . H12A H 0.5128 0.1726 0.3087 0.058 Uiso 1 1 calc R . . H12B H 0.4091 0.008 0.3415 0.058 Uiso 1 1 calc R . . C13 C 0.3453(5) 0.0627(6) 0.25364(18) 0.0542(10) Uani 1 1 d . . . H13A H 0.4072 -0.0479 0.2359 0.065 Uiso 1 1 calc R . . H13B H 0.2473 0.0027 0.2598 0.065 Uiso 1 1 calc R . . C14 C 0.3350(4) 0.2516(6) 0.2108(2) 0.0570(10) Uani 1 1 d . . . H14A H 0.4339 0.3025 0.2013 0.068 Uiso 1 1 calc R . . H14B H 0.2884 0.2059 0.1735 0.068 Uiso 1 1 calc R . . C15 C 0.2458(5) 0.4324(5) 0.2385(2) 0.0536(10) Uani 1 1 d . . . H15A H 0.1443 0.3856 0.2441 0.064 Uiso 1 1 calc R . . H15B H 0.2451 0.554 0.2112 0.064 Uiso 1 1 calc R . . C16 C 0.3100(3) 0.5020(5) 0.29917(17) 0.0436(9) Uani 1 1 d . . . H16A H 0.4067 0.5659 0.2927 0.052 Uiso 1 1 calc R . . H16B H 0.2463 0.6109 0.3166 0.052 Uiso 1 1 calc R . . N9 N 0.3330(3) 0.5447(5) 0.43478(15) 0.0450(7) Uani 1 1 d . . . O1 O 0.2154(3) 0.9215(4) 0.43935(12) 0.0549(7) Uani 1 1 d . . . O2 O 0.1779(2) 0.2529(4) 0.35878(13) 0.0448(7) Uani 1 1 d . . . H2 H 0.182(4) 0.147(7) 0.3763(18) 0.043(12) Uiso 1 1 d . . . H9 H 0.313(4) 0.665(8) 0.419(2) 0.064(13) 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 C2 0.0457(16) 0.0414(18) 0.045(2) 0.0017(16) -0.0113(16) -0.0070(13) C3 0.060(2) 0.0464(19) 0.061(3) -0.0036(19) -0.010(2) 0.0029(16) C4 0.065(2) 0.070(3) 0.065(3) -0.017(2) -0.002(2) 0.007(2) C5 0.084(3) 0.084(3) 0.044(2) -0.002(2) 0.010(2) -0.003(2) C6 0.079(2) 0.058(2) 0.046(2) 0.009(2) -0.003(2) -0.0012(19) C7 0.0516(18) 0.0443(17) 0.040(2) 0.0003(16) -0.0081(15) -0.0049(14) C8 0.0499(17) 0.0430(17) 0.043(2) 0.0072(17) -0.0085(17) -0.0029(14) C10 0.0416(18) 0.048(2) 0.056(2) 0.0032(18) -0.0022(16) 0.0023(14) C11 0.0339(15) 0.0379(16) 0.047(2) 0.0046(15) 0.0032(14) 0.0013(12) C12 0.0449(18) 0.0381(17) 0.062(2) 0.0044(17) 0.0055(16) 0.0081(13) C13 0.062(2) 0.0435(19) 0.057(2) -0.0061(18) 0.0045(19) 0.0016(15) C14 0.065(2) 0.056(2) 0.050(2) 0.003(2) 0.0071(18) -0.0028(18) C15 0.059(2) 0.0504(19) 0.051(2) 0.0110(18) 0.0008(17) 0.0068(17) C16 0.0435(17) 0.0331(16) 0.054(2) 0.0069(16) 0.0068(15) 0.0024(12) N9 0.0464(15) 0.0418(16) 0.0467(19) 0.0020(15) -0.0047(14) -0.0022(11) O1 0.0640(14) 0.0441(14) 0.0566(17) 0.0128(12) 0.0010(14) -0.0026(10) O2 0.0363(11) 0.0415(13) 0.0567(16) 0.0109(13) 0.0020(11) -0.0026(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 O1 1.294(5) . ? C2 C3 1.416(5) . ? C2 C7 1.428(5) . ? C3 C4 1.366(6) . ? C3 H3 0.93 . ? C4 C5 1.397(6) . ? C4 H4 0.93 . ? C5 C6 1.361(6) . ? C5 H5 0.93 . ? C6 C7 1.405(6) . ? C6 H6 0.93 . ? C7 C8 1.416(5) . ? C8 N9 1.284(5) . ? C8 H8 0.93 . ? C10 N9 1.446(5) . ? C10 C11 1.523(5) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 O2 1.428(4) . ? C11 C16 1.524(5) . ? C11 C12 1.534(5) . ? C12 C13 1.529(6) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 C14 1.516(6) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 C15 1.515(5) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C15 C16 1.529(6) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? N9 H9 0.85(5) . ? O2 H2 0.76(5) . ? 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 O1 C2 C3 122.3(3) . . ? O1 C2 C7 120.9(3) . . ? C3 C2 C7 116.7(4) . . ? C4 C3 C2 121.6(4) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 121.2(4) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 119.0(4) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 121.7(4) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C6 C7 C8 120.0(3) . . ? C6 C7 C2 119.8(3) . . ? C8 C7 C2 120.1(3) . . ? N9 C8 C7 123.9(3) . . ? N9 C8 H8 118 . . ? C7 C8 H8 118 . . ? N9 C10 C11 113.1(3) . . ? N9 C10 H10A 109 . . ? C11 C10 H10A 109 . . ? N9 C10 H10B 109 . . ? C11 C10 H10B 109 . . ? H10A C10 H10B 107.8 . . ? O2 C11 C10 110.0(3) . . ? O2 C11 C16 106.3(2) . . ? C10 C11 C16 111.7(3) . . ? O2 C11 C12 111.0(3) . . ? C10 C11 C12 107.6(2) . . ? C16 C11 C12 110.4(3) . . ? C13 C12 C11 112.7(3) . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 111.3(3) . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108 . . ? C15 C14 C13 110.8(3) . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C14 C15 C16 111.6(3) . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 108 . . ? C11 C16 C15 112.7(3) . . ? C11 C16 H16A 109 . . ? C15 C16 H16A 109 . . ? C11 C16 H16B 109 . . ? C15 C16 H16B 109 . . ? H16A C16 H16B 107.8 . . ? C8 N9 C10 124.5(3) . . ? C8 N9 H9 115(3) . . ? C10 N9 H9 120(3) . . ? C11 O2 H2 108(3) . . ? 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 O1 C2 C3 C4 179.5(3) . . . . ? C7 C2 C3 C4 1.4(5) . . . . ? C2 C3 C4 C5 -0.2(6) . . . . ? C3 C4 C5 C6 -0.5(7) . . . . ? C4 C5 C6 C7 -0.2(7) . . . . ? C5 C6 C7 C8 -175.5(4) . . . . ? C5 C6 C7 C2 1.5(6) . . . . ? O1 C2 C7 C6 179.8(3) . . . . ? C3 C2 C7 C6 -2.1(5) . . . . ? O1 C2 C7 C8 -3.2(5) . . . . ? C3 C2 C7 C8 175.0(3) . . . . ? C6 C7 C8 N9 178.8(3) . . . . ? C2 C7 C8 N9 1.8(5) . . . . ? N9 C10 C11 O2 -53.7(4) . . . . ? N9 C10 C11 C16 64.1(4) . . . . ? N9 C10 C11 C12 -174.7(3) . . . . ? O2 C11 C12 C13 65.2(4) . . . . ? C10 C11 C12 C13 -174.4(3) . . . . ? C16 C11 C12 C13 -52.3(4) . . . . ? C11 C12 C13 C14 54.9(4) . . . . ? C12 C13 C14 C15 -56.0(4) . . . . ? C13 C14 C15 C16 56.0(4) . . . . ? O2 C11 C16 C15 -68.2(3) . . . . ? C10 C11 C16 C15 171.8(3) . . . . ? C12 C11 C16 C15 52.2(3) . . . . ? C14 C15 C16 C11 -55.0(4) . . . . ? C7 C8 N9 C10 -174.0(3) . . . . ? C11 C10 N9 C8 110.7(4) . . . . ? _chemical_name_common '2-(((1-hydroxycyclohexyl)methylimino)methyl) phenol' #===END #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_Compound5 _database_code_depnum_ccdc_archive 'CCDC 712150' #TrackingRef '- cifs 1-8_(R2).cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-[1-(2-hydroxyethylimino)ethyl]phenol ; _chemical_formula_moiety 'C10 H13 N O2' _chemical_formula_sum 'C10 H13 N O2' _chemical_formula_weight 179.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.0724(2) _cell_length_b 8.2670(17) _cell_length_c 11.7803(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.75(3) _cell_angle_gamma 90.00 _cell_volume 911.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 600 _cell_measurement_theta_min 1 _cell_measurement_theta_max 10 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 3 _diffrn_standards_number 100 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 3178 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1596 _reflns_number_gt 1186 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97(Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+0.1059P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1596 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.1049 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 H9 H -0.022(2) 0.951(2) 0.1979(18) 0.070(6) Uiso 1 1 d . . . H2 H -0.268(2) 0.624(3) 0.100(2) 0.086(7) Uiso 1 1 d . . . C7 C 0.12961(14) 0.79040(16) 0.13614(13) 0.0365(3) Uani 1 1 d . . . C6 C 0.20807(16) 0.68604(18) 0.08947(15) 0.0448(4) Uani 1 1 d . . . H6 H 0.1617 0.6356 0.0146 0.054 Uiso 1 1 calc R . . C5 C 0.35042(17) 0.6571(2) 0.15133(16) 0.0536(5) Uani 1 1 d . . . H5 H 0.4000 0.5872 0.1193 0.064 Uiso 1 1 calc R . . C4 C 0.42008(17) 0.7336(2) 0.26272(16) 0.0527(4) Uani 1 1 d . . . H4 H 0.5170 0.7147 0.3048 0.063 Uiso 1 1 calc R . . C3 C 0.34897(15) 0.83617(19) 0.31171(14) 0.0460(4) Uani 1 1 d . . . H3 H 0.3985 0.8857 0.3864 0.055 Uiso 1 1 calc R . . C2 C 0.20152(15) 0.86838(17) 0.25093(13) 0.0370(3) Uani 1 1 d . . . C8 C -0.02103(15) 0.82002(17) 0.06735(13) 0.0375(4) Uani 1 1 d . . . C12 C -0.09469(18) 0.7513(2) -0.05762(14) 0.0502(4) Uani 1 1 d . . . H12A H -0.1932 0.7836 -0.0885 0.075 Uiso 0.50 1 calc PR . . H12B H -0.0888 0.6354 -0.0537 0.075 Uiso 0.50 1 calc PR . . H12C H -0.0494 0.7907 -0.1110 0.075 Uiso 0.50 1 calc PR . . H12D H -0.0277 0.6895 -0.0803 0.075 Uiso 0.50 1 calc PR . . H12E H -0.1322 0.8377 -0.1150 0.075 Uiso 0.50 1 calc PR . . H12F H -0.1715 0.6825 -0.0578 0.075 Uiso 0.50 1 calc PR . . C11 C -0.33033(16) 0.8374(2) 0.10568(17) 0.0537(5) Uani 1 1 d . . . H11A H -0.2925 0.8286 0.1941 0.064 Uiso 1 1 calc R . . H11B H -0.4272 0.8785 0.0804 0.064 Uiso 1 1 calc R . . C10 C -0.24026(15) 0.95598(19) 0.06747(15) 0.0465(4) Uani 1 1 d . . . H10A H -0.2732 0.9586 -0.0210 0.056 Uiso 1 1 calc R . . H10B H -0.2520 1.0635 0.0954 0.056 Uiso 1 1 calc R . . N9 N -0.08915(13) 0.91212(15) 0.11766(12) 0.0405(3) Uani 1 1 d . . . O1 O 0.13525(10) 0.96772(13) 0.29924(9) 0.0447(3) Uani 1 1 d . . . O2 O -0.33317(13) 0.68326(15) 0.05487(13) 0.0626(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C7 0.0360(7) 0.0330(7) 0.0404(8) 0.0028(6) 0.0141(6) -0.0038(6) C6 0.0462(9) 0.0426(9) 0.0468(9) -0.0028(7) 0.0184(7) -0.0024(7) C5 0.0478(9) 0.0542(10) 0.0639(11) 0.0000(8) 0.0266(8) 0.0078(8) C4 0.0338(8) 0.0589(10) 0.0631(11) 0.0095(9) 0.0152(8) 0.0030(7) C3 0.0363(8) 0.0501(9) 0.0465(9) 0.0017(7) 0.0093(7) -0.0055(7) C2 0.0358(7) 0.0350(7) 0.0403(8) 0.0028(6) 0.0141(6) -0.0051(6) C8 0.0387(8) 0.0329(7) 0.0387(8) 0.0014(6) 0.0117(6) -0.0063(6) C12 0.0472(9) 0.0530(10) 0.0432(9) -0.0044(7) 0.0081(7) -0.0051(7) C11 0.0324(8) 0.0634(11) 0.0604(10) 0.0134(8) 0.0113(7) 0.0031(7) C10 0.0355(8) 0.0407(8) 0.0574(10) 0.0038(7) 0.0104(7) 0.0047(6) N9 0.0323(6) 0.0392(7) 0.0457(7) -0.0029(6) 0.0092(6) -0.0037(5) O1 0.0389(6) 0.0498(6) 0.0432(6) -0.0091(5) 0.0128(5) -0.0025(5) O2 0.0438(7) 0.0485(7) 0.0758(9) 0.0170(6) -0.0010(6) -0.0048(6) _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 C7 C6 1.412(2) . ? C7 C2 1.429(2) . ? C7 C8 1.452(2) . ? C6 C5 1.367(2) . ? C6 H6 0.9300 . ? C5 C4 1.390(2) . ? C5 H5 0.9300 . ? C4 C3 1.368(2) . ? C4 H4 0.9300 . ? C3 C2 1.415(2) . ? C3 H3 0.9300 . ? C2 O1 1.3135(17) . ? C8 N9 1.3050(18) . ? C8 C12 1.494(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C12 H12D 0.9600 . ? C12 H12E 0.9600 . ? C12 H12F 0.9600 . ? C11 O2 1.404(2) . ? C11 C10 1.513(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C10 N9 1.4597(19) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N9 H9 0.99(2) . ? O2 H2 0.83(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C7 C2 118.92(13) . . ? C6 C7 C8 120.38(13) . . ? C2 C7 C8 120.70(13) . . ? C5 C6 C7 121.80(15) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C6 C5 C4 119.10(16) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C3 C4 C5 121.35(15) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C4 C3 C2 121.25(15) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? O1 C2 C3 120.34(13) . . ? O1 C2 C7 122.09(13) . . ? C3 C2 C7 117.57(14) . . ? N9 C8 C7 117.48(13) . . ? N9 C8 C12 121.12(14) . . ? C7 C8 C12 121.38(14) . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C12 H12D 109.5 . . ? H12A C12 H12D 141.1 . . ? H12B C12 H12D 56.3 . . ? H12C C12 H12D 56.3 . . ? C8 C12 H12E 109.5 . . ? H12A C12 H12E 56.3 . . ? H12B C12 H12E 141.1 . . ? H12C C12 H12E 56.3 . . ? H12D C12 H12E 109.5 . . ? C8 C12 H12F 109.5 . . ? H12A C12 H12F 56.3 . . ? H12B C12 H12F 56.3 . . ? H12C C12 H12F 141.1 . . ? H12D C12 H12F 109.5 . . ? H12E C12 H12F 109.5 . . ? O2 C11 C10 112.40(14) . . ? O2 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? O2 C11 H11B 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? N9 C10 C11 111.64(13) . . ? N9 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? N9 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C8 N9 C10 127.28(13) . . ? C8 N9 H9 109.5(10) . . ? C10 N9 H9 123.3(11) . . ? C11 O2 H2 111.8(16) . . ? 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 C7 C6 C5 0.3(2) . . . . ? C8 C7 C6 C5 179.23(14) . . . . ? C7 C6 C5 C4 -0.6(2) . . . . ? C6 C5 C4 C3 0.4(3) . . . . ? C5 C4 C3 C2 0.1(3) . . . . ? C4 C3 C2 O1 -179.74(13) . . . . ? C4 C3 C2 C7 -0.3(2) . . . . ? C6 C7 C2 O1 179.54(12) . . . . ? C8 C7 C2 O1 0.7(2) . . . . ? C6 C7 C2 C3 0.08(19) . . . . ? C8 C7 C2 C3 -178.81(13) . . . . ? C6 C7 C8 N9 177.13(13) . . . . ? C2 C7 C8 N9 -4.00(19) . . . . ? C6 C7 C8 C12 -4.4(2) . . . . ? C2 C7 C8 C12 174.48(13) . . . . ? O2 C11 C10 N9 -66.71(18) . . . . ? C7 C8 N9 C10 -178.67(13) . . . . ? C12 C8 N9 C10 2.8(2) . . . . ? C11 C10 N9 C8 90.61(19) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.113 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.035 _chemical_name_common 2-(1-(2-hydroxyethylimino)ethyl)phenol #===END #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_Compound2 _database_code_depnum_ccdc_archive 'CCDC 712151' #TrackingRef '- cifs 1-8_(R2).cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2,4-ditertbutyl-6-[(2-hydroxymethylphenylimino)methyl] phenol ; _chemical_formula_moiety 'C22 H29 N1 O2' _chemical_formula_sum 'C22 H29 N O2' _chemical_formula_weight 339.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2518(2) _cell_length_b 10.4845(2) _cell_length_c 19.6987(4) _cell_angle_alpha 95.9376(7) _cell_angle_beta 104.1553(8) _cell_angle_gamma 92.2975(8) _cell_volume 2037.31(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14677 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.107 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.070 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23875 _diffrn_reflns_av_R_equivalents 0.0575 _diffrn_reflns_av_sigmaI/netI 0.0772 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.07 _diffrn_reflns_theta_max 27.56 _reflns_number_total 9270 _reflns_number_gt 5174 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0846P)^2^+0.2356P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9270 _refine_ls_number_parameters 495 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1378 _refine_ls_R_factor_gt 0.0719 _refine_ls_wR_factor_ref 0.2251 _refine_ls_wR_factor_gt 0.1864 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # ATOMIC TYPES, 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 H1B H 0.094(3) 0.375(3) 0.7784(15) 0.091(9) Uiso 1 1 d . . . H1A H 0.379(3) 0.791(3) 0.8443(16) 0.093(10) Uiso 1 1 d . . . H16B H 0.263(3) 0.921(3) 0.9202(14) 0.082(8) Uiso 1 1 d . . . H16A H 0.210(3) 0.781(3) 0.9329(14) 0.087(9) Uiso 1 1 d . . . C2A C 0.48393(19) 0.78422(19) 0.78453(11) 0.0476(5) Uani 1 1 d . . . C3A C 0.4931(2) 0.7893(2) 0.71452(11) 0.0495(5) Uani 1 1 d . . . O2C O 0.1533(7) 0.9579(7) 0.9813(5) 0.076(2) Uani 0.374(2) 1 d PD A 1 H2C H 0.0976 0.9844 0.9493 0.114 Uiso 0.374(2) 1 calc PR A 1 O2A O 0.1073(4) 0.8981(4) 0.9613(3) 0.0715(13) Uani 0.627(4) 1 d PD A 2 H2A H 0.1047 0.9763 0.9684 0.107 Uiso 0.627(4) 1 calc PR A 2 C4A C 0.6215(2) 0.7941(2) 0.70376(11) 0.0539(5) Uani 1 1 d . . . H4A H 0.6289 0.7953 0.6577 0.065 Uiso 1 1 calc R . . C5A C 0.7414(2) 0.7973(2) 0.75687(11) 0.0511(5) Uani 1 1 d . B . C6A C 0.72747(19) 0.7963(2) 0.82453(10) 0.0490(5) Uani 1 1 d . . . H6A H 0.8046 0.8006 0.8614 0.059 Uiso 1 1 calc R . . C7A C 0.60111(19) 0.78922(19) 0.83961(10) 0.0457(5) Uani 1 1 d . . . C8A C 0.5956(2) 0.80291(19) 0.91289(11) 0.0485(5) Uani 1 1 d . . . H8A H 0.6761 0.8117 0.9478 0.058 Uiso 1 1 calc R . . C10A C 0.4801(2) 0.83204(19) 1.00295(11) 0.0509(5) Uani 1 1 d U . . C15A C 0.3547(2) 0.86549(19) 1.01377(12) 0.0567(6) Uani 1 1 d U A . C14A C 0.3450(3) 0.8947(2) 1.08257(15) 0.0716(7) Uani 1 1 d U . . H14A H 0.2628 0.9171 1.0907 0.086 Uiso 1 1 calc R . . C13A C 0.4536(3) 0.8912(2) 1.13906(14) 0.0764(8) Uani 1 1 d U . . H13A H 0.4442 0.9104 1.1847 0.092 Uiso 1 1 calc R . . C12A C 0.5758(3) 0.8595(2) 1.12805(13) 0.0747(7) Uani 1 1 d U . . H12A H 0.6500 0.8588 1.1662 0.090 Uiso 1 1 calc R . . C11A C 0.5887(3) 0.8288(2) 1.06028(12) 0.0647(6) Uani 1 1 d U . . H11A H 0.6713 0.8056 1.0531 0.078 Uiso 1 1 calc R . . C16A C 0.2372(3) 0.8678(3) 0.95088(16) 0.0721(7) Uani 1 1 d D . . C21A C 0.3662(2) 0.7922(2) 0.65418(12) 0.0621(6) Uani 1 1 d U . . C17A C 0.8810(2) 0.8073(3) 0.74120(13) 0.0718(6) Uani 1 1 d DU . . C23A C 0.2922(3) 0.9125(3) 0.66827(15) 0.0836(8) Uani 1 1 d U . . H23A H 0.2666 0.9106 0.7119 0.125 Uiso 1 1 calc R . . H23B H 0.2129 0.9144 0.6305 0.125 Uiso 1 1 calc R . . H23C H 0.3506 0.9878 0.6712 0.125 Uiso 1 1 calc R . . C24A C 0.2727(2) 0.6707(3) 0.64719(14) 0.0784(7) Uani 1 1 d U . . H24A H 0.3193 0.5961 0.6372 0.118 Uiso 1 1 calc R . . H24B H 0.1937 0.6742 0.6095 0.118 Uiso 1 1 calc R . . H24C H 0.2466 0.6657 0.6905 0.118 Uiso 1 1 calc R . . C22A C 0.4017(3) 0.7981(3) 0.58325(13) 0.0882(9) Uani 1 1 d U . . H22A H 0.4602 0.8733 0.5860 0.132 Uiso 1 1 calc R . . H22B H 0.3207 0.8019 0.5469 0.132 Uiso 1 1 calc R . . H22C H 0.4465 0.7228 0.5724 0.132 Uiso 1 1 calc R . . C18A C 0.9694(3) 0.7058(4) 0.7777(2) 0.0718(6) Uani 0.707(3) 1 d PDU B 1 H18A H 0.9291 0.6213 0.7587 0.108 Uiso 0.707(3) 1 calc PR B 1 H18B H 0.9762 0.7183 0.8274 0.108 Uiso 0.707(3) 1 calc PR B 1 H18C H 1.0577 0.7146 0.7696 0.108 Uiso 0.707(3) 1 calc PR B 1 C20A C 0.8764(5) 0.7902(6) 0.6633(2) 0.0991(10) Uani 0.707(3) 1 d PDU B 1 H20A H 0.9665 0.7882 0.6574 0.149 Uiso 0.707(3) 1 calc PR B 1 H20B H 0.8335 0.8607 0.6415 0.149 Uiso 0.707(3) 1 calc PR B 1 H20C H 0.8262 0.7111 0.6416 0.149 Uiso 0.707(3) 1 calc PR B 1 C19A C 0.9496(4) 0.9434(5) 0.7721(3) 0.0991(10) Uani 0.707(3) 1 d PDU B 1 H19A H 1.0353 0.9524 0.7609 0.149 Uiso 0.707(3) 1 calc PR B 1 H19B H 0.9628 0.9538 0.8224 0.149 Uiso 0.707(3) 1 calc PR B 1 H19C H 0.8930 1.0077 0.7521 0.149 Uiso 0.707(3) 1 calc PR B 1 C18C C 0.9950(9) 0.7902(14) 0.8040(5) 0.0991(10) Uani 0.293(3) 1 d PD B 2 H18D H 0.9756 0.7135 0.8235 0.149 Uiso 0.293(3) 1 calc PR B 2 H18E H 1.0045 0.8630 0.8390 0.149 Uiso 0.293(3) 1 calc PR B 2 H18F H 1.0774 0.7831 0.7893 0.149 Uiso 0.293(3) 1 calc PR B 2 C20C C 0.8769(11) 0.7083(13) 0.6759(6) 0.0991(10) Uani 0.293(3) 1 d PD B 2 H20D H 0.8122 0.7315 0.6357 0.149 Uiso 0.293(3) 1 calc PR B 2 H20E H 0.8515 0.6241 0.6853 0.149 Uiso 0.293(3) 1 calc PR B 2 H20F H 0.9644 0.7084 0.6664 0.149 Uiso 0.293(3) 1 calc PR B 2 C19C C 0.9018(11) 0.9414(10) 0.7221(6) 0.0991(10) Uani 0.293(3) 1 d PD B 2 H19D H 0.9959 0.9607 0.7262 0.149 Uiso 0.293(3) 1 calc PR B 2 H19E H 0.8708 1.0023 0.7535 0.149 Uiso 0.293(3) 1 calc PR B 2 H19F H 0.8517 0.9463 0.6745 0.149 Uiso 0.293(3) 1 calc PR B 2 N9A N 0.48419(17) 0.80341(16) 0.93143(9) 0.0512(4) Uani 1 1 d . . . O1A O 0.36120(14) 0.77888(17) 0.79871(9) 0.0647(5) Uani 1 1 d . . . C2B C 0.1903(2) 0.3492(2) 0.71105(11) 0.0504(5) Uani 1 1 d . . . C3B C 0.1963(2) 0.3077(2) 0.64187(11) 0.0533(5) Uani 1 1 d . . . C4B C 0.3236(2) 0.3059(2) 0.62982(11) 0.0584(6) Uani 1 1 d . . . H4B H 0.3294 0.2781 0.5843 0.070 Uiso 1 1 calc R . . C5B C 0.4447(2) 0.3427(2) 0.68066(12) 0.0573(6) Uani 1 1 d . . . C6B C 0.4331(2) 0.3851(2) 0.74692(11) 0.0564(5) Uani 1 1 d . . . H6B H 0.5108 0.4128 0.7819 0.068 Uiso 1 1 calc R . . C7B C 0.3083(2) 0.3879(2) 0.76362(10) 0.0504(5) Uani 1 1 d . . . C8B C 0.3051(2) 0.4210(2) 0.83632(11) 0.0535(5) Uani 1 1 d . . . H8B H 0.3854 0.4490 0.8693 0.064 Uiso 1 1 calc R . . C10B C 0.2000(2) 0.43614(19) 0.93006(10) 0.0489(5) Uani 1 1 d . . . C15B C 0.1117(2) 0.3602(2) 0.95535(11) 0.0522(5) Uani 1 1 d . . . C14B C 0.1128(3) 0.3827(2) 1.02617(12) 0.0657(6) Uani 1 1 d . . . H14B H 0.0535 0.3338 1.0436 0.079 Uiso 1 1 calc R . . C13B C 0.1996(3) 0.4756(3) 1.07133(13) 0.0715(7) Uani 1 1 d . . . H13B H 0.1990 0.4885 1.1187 0.086 Uiso 1 1 calc R . . C12B C 0.2867(3) 0.5488(2) 1.04627(13) 0.0709(7) Uani 1 1 d . . . H12B H 0.3456 0.6115 1.0767 0.085 Uiso 1 1 calc R . . C11B C 0.2875(2) 0.5301(2) 0.97597(12) 0.0638(6) Uani 1 1 d . . . H11B H 0.3467 0.5805 0.9592 0.077 Uiso 1 1 calc R . . C16B C 0.0213(3) 0.2527(2) 0.90841(13) 0.0698(7) Uani 1 1 d . . . H16C H -0.0695 0.2809 0.8947 0.084 Uiso 1 1 calc R . . H16D H 0.0522 0.2342 0.8659 0.084 Uiso 1 1 calc R . . C21B C 0.0673(2) 0.2694(3) 0.58286(12) 0.0643(6) Uani 1 1 d U . . C17B C 0.5798(2) 0.3353(3) 0.66071(13) 0.0712(7) Uani 1 1 d D . . C22B C -0.0220(2) 0.3831(3) 0.57478(14) 0.0800(8) Uani 1 1 d . . . H22D H -0.0443 0.4083 0.6186 0.120 Uiso 1 1 calc R . . H22F H -0.1032 0.3585 0.5386 0.120 Uiso 1 1 calc R . . H22E H 0.0256 0.4539 0.5620 0.120 Uiso 1 1 calc R . . C23B C -0.0104(3) 0.1538(3) 0.60037(16) 0.0863(8) Uani 1 1 d . . . H23D H 0.0447 0.0818 0.6038 0.130 Uiso 1 1 calc R . . H23E H -0.0916 0.1320 0.5638 0.130 Uiso 1 1 calc R . . H23F H -0.0329 0.1756 0.6445 0.130 Uiso 1 1 calc R . . C24B C 0.0993(3) 0.2313(4) 0.51158(14) 0.1088(12) Uani 1 1 d . . . H24F H 0.1457 0.3029 0.4988 0.163 Uiso 1 1 calc R . . H24D H 0.0169 0.2074 0.4762 0.163 Uiso 1 1 calc R . . H24E H 0.1555 0.1600 0.5152 0.163 Uiso 1 1 calc R . . C19B C 0.6989(3) 0.3772(4) 0.72339(17) 0.1180(14) Uani 1 1 d DU . . H19G H 0.6902 0.4638 0.7421 0.177 Uiso 1 1 calc R . . H19H H 0.7812 0.3730 0.7085 0.177 Uiso 1 1 calc R . . H19I H 0.7003 0.3212 0.7591 0.177 Uiso 1 1 calc R . . C20B C 0.5947(3) 0.1968(4) 0.6316(2) 0.1188(13) Uani 1 1 d DU . . H20G H 0.5955 0.1413 0.6675 0.178 Uiso 1 1 calc R . . H20H H 0.6776 0.1926 0.6172 0.178 Uiso 1 1 calc R . . H20I H 0.5203 0.1697 0.5917 0.178 Uiso 1 1 calc R . . C18B C 0.5830(3) 0.4234(4) 0.60410(18) 0.1075(11) Uani 1 1 d DU . . H18G H 0.5078 0.3994 0.5643 0.161 Uiso 1 1 calc R . . H18H H 0.6655 0.4155 0.5896 0.147(13) Uiso 1 1 calc R . . H18I H 0.5778 0.5108 0.6228 0.21(2) Uiso 1 1 calc R . . N9B N 0.19669(17) 0.41362(17) 0.85728(9) 0.0519(4) Uani 1 1 d . . . O2B O 0.0176(2) 0.13949(17) 0.94041(12) 0.0949(6) Uani 1 1 d D . . H2B H -0.0180 0.1519 0.9733 0.142 Uiso 1 1 calc RD . . O1B O 0.06850(14) 0.34947(17) 0.72697(9) 0.0644(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2A 0.0387(11) 0.0554(12) 0.0503(12) 0.0046(9) 0.0143(9) 0.0060(9) C3A 0.0425(11) 0.0584(12) 0.0466(12) 0.0026(9) 0.0106(9) 0.0030(9) O2C 0.060(4) 0.087(5) 0.099(6) 0.032(4) 0.043(4) 0.034(3) O2A 0.065(3) 0.081(3) 0.086(3) 0.025(2) 0.044(2) 0.0220(19) C4A 0.0493(12) 0.0733(14) 0.0390(11) 0.0038(10) 0.0127(9) -0.0002(10) C5A 0.0426(11) 0.0664(13) 0.0458(12) 0.0018(9) 0.0165(9) 0.0009(9) C6A 0.0392(10) 0.0628(13) 0.0439(11) 0.0038(9) 0.0093(9) 0.0049(9) C7A 0.0450(11) 0.0512(11) 0.0434(11) 0.0054(8) 0.0151(9) 0.0069(9) C8A 0.0472(11) 0.0535(12) 0.0477(12) 0.0072(9) 0.0160(9) 0.0087(9) C10A 0.0650(13) 0.0449(11) 0.0511(12) 0.0107(9) 0.0275(10) 0.0080(10) C15A 0.0747(15) 0.0447(11) 0.0654(14) 0.0146(10) 0.0410(12) 0.0121(10) C14A 0.103(2) 0.0544(13) 0.0785(18) 0.0128(12) 0.0598(16) 0.0117(13) C13A 0.131(2) 0.0533(14) 0.0586(16) 0.0053(11) 0.0516(17) 0.0059(14) C12A 0.111(2) 0.0652(15) 0.0505(14) 0.0089(11) 0.0242(14) 0.0106(14) C11A 0.0784(16) 0.0682(15) 0.0541(14) 0.0131(11) 0.0248(12) 0.0162(12) C16A 0.0647(16) 0.086(2) 0.086(2) 0.0326(16) 0.0449(15) 0.0276(14) C21A 0.0478(12) 0.0812(16) 0.0545(13) 0.0122(11) 0.0050(10) 0.0074(11) C17A 0.0426(10) 0.1121(17) 0.0631(13) 0.0020(11) 0.0218(9) -0.0003(10) C23A 0.0675(16) 0.0917(19) 0.087(2) 0.0220(15) 0.0033(14) 0.0216(14) C24A 0.0542(14) 0.0890(18) 0.0786(18) 0.0045(14) -0.0051(12) -0.0068(13) C22A 0.0675(16) 0.141(3) 0.0508(15) 0.0219(15) -0.0003(12) 0.0071(16) C18A 0.0426(10) 0.1121(17) 0.0631(13) 0.0020(11) 0.0218(9) -0.0003(10) C20A 0.0696(16) 0.151(3) 0.0798(19) -0.008(2) 0.0384(15) -0.0270(19) C19A 0.0696(16) 0.151(3) 0.0798(19) -0.008(2) 0.0384(15) -0.0270(19) C18C 0.0696(16) 0.151(3) 0.0798(19) -0.008(2) 0.0384(15) -0.0270(19) C20C 0.0696(16) 0.151(3) 0.0798(19) -0.008(2) 0.0384(15) -0.0270(19) C19C 0.0696(16) 0.151(3) 0.0798(19) -0.008(2) 0.0384(15) -0.0270(19) N9A 0.0550(10) 0.0569(10) 0.0490(10) 0.0104(8) 0.0239(8) 0.0104(8) O1A 0.0395(8) 0.1002(13) 0.0573(11) 0.0073(9) 0.0183(7) 0.0066(8) C2B 0.0421(11) 0.0642(13) 0.0487(12) 0.0135(10) 0.0160(9) 0.0020(9) C3B 0.0465(11) 0.0681(14) 0.0464(12) 0.0069(10) 0.0140(9) 0.0022(10) C4B 0.0553(13) 0.0776(15) 0.0453(12) 0.0026(10) 0.0207(10) 0.0025(11) C5B 0.0445(12) 0.0765(15) 0.0541(13) 0.0083(11) 0.0183(10) 0.0028(10) C6B 0.0413(11) 0.0804(15) 0.0466(12) 0.0086(10) 0.0094(9) -0.0003(10) C7B 0.0460(11) 0.0641(13) 0.0435(11) 0.0105(9) 0.0141(9) 0.0021(9) C8B 0.0478(12) 0.0670(14) 0.0450(12) 0.0079(10) 0.0102(9) 0.0019(10) C10B 0.0540(12) 0.0521(12) 0.0444(11) 0.0092(9) 0.0169(9) 0.0106(10) C15B 0.0539(12) 0.0591(13) 0.0492(12) 0.0134(10) 0.0189(10) 0.0139(10) C14B 0.0732(15) 0.0789(16) 0.0540(14) 0.0198(12) 0.0263(12) 0.0175(13) C13B 0.0982(19) 0.0745(16) 0.0452(13) 0.0102(12) 0.0195(13) 0.0264(15) C12B 0.0941(19) 0.0610(14) 0.0523(14) 0.0003(11) 0.0100(13) 0.0101(13) C11B 0.0750(16) 0.0550(13) 0.0623(15) 0.0044(11) 0.0203(12) 0.0018(12) C16B 0.0642(15) 0.0743(16) 0.0751(17) 0.0173(13) 0.0231(13) -0.0045(12) C21B 0.0475(12) 0.0904(17) 0.0504(13) -0.0007(11) 0.0083(10) 0.0000(12) C17B 0.0488(13) 0.1005(19) 0.0678(16) -0.0003(14) 0.0257(12) 0.0023(12) C22B 0.0635(15) 0.105(2) 0.0638(16) 0.0211(14) -0.0040(12) 0.0067(14) C23B 0.0637(16) 0.0877(19) 0.097(2) -0.0017(16) 0.0078(15) -0.0086(14) C24B 0.0749(18) 0.187(4) 0.0514(16) -0.0226(19) 0.0084(14) -0.003(2) C19B 0.0454(15) 0.209(4) 0.096(2) -0.012(2) 0.0251(15) -0.0085(19) C20B 0.075(2) 0.128(3) 0.161(3) -0.014(2) 0.054(2) 0.0188(19) C18B 0.076(2) 0.153(3) 0.113(3) 0.030(2) 0.0582(19) 0.0012(19) N9B 0.0533(10) 0.0628(11) 0.0431(10) 0.0108(8) 0.0167(8) 0.0056(8) O2B 0.1345(18) 0.0637(11) 0.1087(16) 0.0140(10) 0.0712(14) 0.0057(11) O1B 0.0418(8) 0.1014(13) 0.0515(10) 0.0066(8) 0.0159(7) 0.0026(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2A O1A 1.354(2) . ? C2A C7A 1.403(3) . ? C2A C3A 1.411(3) . ? C3A C4A 1.384(3) . ? C3A C21A 1.536(3) . ? O2C C16A 1.480(7) . ? O2C H2C 0.8200 . ? O2A C16A 1.439(4) . ? O2A H2A 0.8200 . ? C4A C5A 1.402(3) . ? C4A H4A 0.9300 . ? C5A C6A 1.376(3) . ? C5A C17A 1.538(3) . ? C6A C7A 1.399(3) . ? C6A H6A 0.9300 . ? C7A C8A 1.451(3) . ? C8A N9A 1.281(2) . ? C8A H8A 0.9300 . ? C10A C11A 1.383(3) . ? C10A C15A 1.406(3) . ? C10A N9A 1.421(2) . ? C15A C14A 1.387(3) . ? C15A C16A 1.505(4) . ? C14A C13A 1.373(4) . ? C14A H14A 0.9300 . ? C13A C12A 1.371(4) . ? C13A H13A 0.9300 . ? C12A C11A 1.380(3) . ? C12A H12A 0.9300 . ? C11A H11A 0.9300 . ? C16A H16B 0.94(3) . ? C16A H16A 0.94(3) . ? C21A C23A 1.534(3) . ? C21A C22A 1.534(3) . ? C21A C24A 1.537(3) . ? C17A C18C 1.511(10) . ? C17A C19C 1.512(10) . ? C17A C20A 1.515(5) . ? C17A C18A 1.545(5) . ? C17A C20C 1.558(10) . ? C17A C19A 1.559(5) . ? C23A H23A 0.9600 . ? C23A H23B 0.9600 . ? C23A H23C 0.9600 . ? C24A H24A 0.9600 . ? C24A H24B 0.9600 . ? C24A H24C 0.9600 . ? C22A H22A 0.9600 . ? C22A H22B 0.9600 . ? C22A H22C 0.9600 . ? C18A H18A 0.9600 . ? C18A H18B 0.9600 . ? C18A H18C 0.9600 . ? C20A H20A 0.9600 . ? C20A H20B 0.9600 . ? C20A H20C 0.9600 . ? C19A H19A 0.9600 . ? C19A H19B 0.9600 . ? C19A H19C 0.9600 . ? C18C H18D 0.9600 . ? C18C H18E 0.9600 . ? C18C H18F 0.9600 . ? C20C H20D 0.9600 . ? C20C H20E 0.9600 . ? C20C H20F 0.9600 . ? C19C H19D 0.9600 . ? C19C H19E 0.9600 . ? C19C H19F 0.9600 . ? O1A H1A 0.87(3) . ? C2B O1B 1.360(2) . ? C2B C7B 1.400(3) . ? C2B C3B 1.404(3) . ? C3B C4B 1.383(3) . ? C3B C21B 1.540(3) . ? C4B C5B 1.402(3) . ? C4B H4B 0.9300 . ? C5B C6B 1.369(3) . ? C5B C17B 1.532(3) . ? C6B C7B 1.398(3) . ? C6B H6B 0.9300 . ? C7B C8B 1.447(3) . ? C8B N9B 1.279(2) . ? C8B H8B 0.9300 . ? C10B C11B 1.393(3) . ? C10B C15B 1.396(3) . ? C10B N9B 1.420(2) . ? C15B C14B 1.387(3) . ? C15B C16B 1.505(3) . ? C14B C13B 1.377(4) . ? C14B H14B 0.9300 . ? C13B C12B 1.367(4) . ? C13B H13B 0.9300 . ? C12B C11B 1.380(3) . ? C12B H12B 0.9300 . ? C11B H11B 0.9300 . ? C16B O2B 1.404(3) . ? C16B H16C 0.9700 . ? C16B H16D 0.9700 . ? C21B C22B 1.530(4) . ? C21B C24B 1.536(3) . ? C21B C23B 1.538(4) . ? C17B C19B 1.522(4) . ? C17B C18B 1.525(4) . ? C17B C20B 1.533(4) . ? C22B H22D 0.9600 . ? C22B H22F 0.9600 . ? C22B H22E 0.9600 . ? C23B H23D 0.9600 . ? C23B H23E 0.9600 . ? C23B H23F 0.9600 . ? C24B H24F 0.9600 . ? C24B H24D 0.9600 . ? C24B H24E 0.9600 . ? C19B H19G 0.9600 . ? C19B H19H 0.9600 . ? C19B H19I 0.9600 . ? C20B H20G 0.9600 . ? C20B H20H 0.9600 . ? C20B H20I 0.9600 . ? C18B H18G 0.9600 . ? C18B H18H 0.9600 . ? C18B H18I 0.9600 . ? O2B H2B 0.8200 . ? O1B H1B 0.99(3) . ? 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 O1A C2A C7A 119.98(18) . . ? O1A C2A C3A 119.58(18) . . ? C7A C2A C3A 120.40(17) . . ? C4A C3A C2A 116.54(18) . . ? C4A C3A C21A 122.30(19) . . ? C2A C3A C21A 121.16(18) . . ? C16A O2C H2C 109.5 . . ? C16A O2A H2A 109.5 . . ? C3A C4A C5A 125.12(19) . . ? C3A C4A H4A 117.4 . . ? C5A C4A H4A 117.4 . . ? C6A C5A C4A 116.18(18) . . ? C6A C5A C17A 121.58(19) . . ? C4A C5A C17A 122.19(19) . . ? C5A C6A C7A 122.15(18) . . ? C5A C6A H6A 118.9 . . ? C7A C6A H6A 118.9 . . ? C6A C7A C2A 119.55(18) . . ? C6A C7A C8A 118.45(18) . . ? C2A C7A C8A 121.57(17) . . ? N9A C8A C7A 122.58(19) . . ? N9A C8A H8A 118.7 . . ? C7A C8A H8A 118.7 . . ? C11A C10A C15A 119.71(19) . . ? C11A C10A N9A 124.69(19) . . ? C15A C10A N9A 115.61(19) . . ? C14A C15A C10A 118.0(2) . . ? C14A C15A C16A 122.9(2) . . ? C10A C15A C16A 119.09(19) . . ? C13A C14A C15A 121.7(2) . . ? C13A C14A H14A 119.1 . . ? C15A C14A H14A 119.1 . . ? C12A C13A C14A 119.9(2) . . ? C12A C13A H13A 120.1 . . ? C14A C13A H13A 120.1 . . ? C13A C12A C11A 119.9(3) . . ? C13A C12A H12A 120.1 . . ? C11A C12A H12A 120.1 . . ? C12A C11A C10A 120.7(2) . . ? C12A C11A H11A 119.6 . . ? C10A C11A H11A 119.6 . . ? O2A C16A C15A 119.7(3) . . ? O2C C16A C15A 100.3(4) . . ? O2A C16A H16B 110.3(16) . . ? O2C C16A H16B 97.8(16) . . ? C15A C16A H16B 108.4(16) . . ? O2A C16A H16A 94.5(17) . . ? O2C C16A H16A 124.7(17) . . ? C15A C16A H16A 106.5(17) . . ? H16B C16A H16A 117(2) . . ? C23A C21A C22A 107.5(2) . . ? C23A C21A C3A 109.44(19) . . ? C22A C21A C3A 111.56(19) . . ? C23A C21A C24A 110.2(2) . . ? C22A C21A C24A 107.6(2) . . ? C3A C21A C24A 110.5(2) . . ? C18C C17A C19C 107.2(7) . . ? C18C C17A C20A 129.8(4) . . ? C19C C17A C20A 74.5(5) . . ? C18C C17A C5A 113.1(4) . . ? C19C C17A C5A 107.1(4) . . ? C20A C17A C5A 113.8(2) . . ? C19C C17A C18A 137.3(5) . . ? C20A C17A C18A 108.9(3) . . ? C5A C17A C18A 109.5(2) . . ? C18C C17A C20C 112.9(7) . . ? C19C C17A C20C 108.9(7) . . ? C5A C17A C20C 107.4(4) . . ? C18A C17A C20C 80.3(6) . . ? C18C C17A C19A 72.8(5) . . ? C20A C17A C19A 107.4(3) . . ? C5A C17A C19A 108.5(2) . . ? C18A C17A C19A 108.5(3) . . ? C20C C17A C19A 137.1(5) . . ? C21A C23A H23A 109.5 . . ? C21A C23A H23B 109.5 . . ? H23A C23A H23B 109.5 . . ? C21A C23A H23C 109.5 . . ? H23A C23A H23C 109.5 . . ? H23B C23A H23C 109.5 . . ? C21A C24A H24A 109.5 . . ? C21A C24A H24B 109.5 . . ? H24A C24A H24B 109.5 . . ? C21A C24A H24C 109.5 . . ? H24A C24A H24C 109.5 . . ? H24B C24A H24C 109.5 . . ? C21A C22A H22A 109.5 . . ? C21A C22A H22B 109.5 . . ? H22A C22A H22B 109.5 . . ? C21A C22A H22C 109.5 . . ? H22A C22A H22C 109.5 . . ? H22B C22A H22C 109.5 . . ? C17A C18A H18A 109.5 . . ? C17A C18A H18B 109.5 . . ? C17A C18A H18C 109.5 . . ? C17A C20A H20A 109.5 . . ? C17A C20A H20B 109.5 . . ? C17A C20A H20C 109.5 . . ? C17A C19A H19A 109.5 . . ? C17A C19A H19B 109.5 . . ? C17A C19A H19C 109.5 . . ? C17A C18C H18D 109.5 . . ? C17A C18C H18E 109.5 . . ? H18D C18C H18E 109.5 . . ? C17A C18C H18F 109.5 . . ? H18D C18C H18F 109.5 . . ? H18E C18C H18F 109.5 . . ? C17A C20C H20D 109.5 . . ? C17A C20C H20E 109.5 . . ? H20D C20C H20E 109.5 . . ? C17A C20C H20F 109.5 . . ? H20D C20C H20F 109.5 . . ? H20E C20C H20F 109.5 . . ? C17A C19C H19D 109.5 . . ? C17A C19C H19E 109.5 . . ? H19D C19C H19E 109.5 . . ? C17A C19C H19F 109.5 . . ? H19D C19C H19F 109.5 . . ? H19E C19C H19F 109.5 . . ? C8A N9A C10A 121.93(18) . . ? C2A O1A H1A 104.0(19) . . ? O1B C2B C7B 120.08(18) . . ? O1B C2B C3B 119.30(18) . . ? C7B C2B C3B 120.61(18) . . ? C4B C3B C2B 116.31(19) . . ? C4B C3B C21B 122.41(19) . . ? C2B C3B C21B 121.27(18) . . ? C3B C4B C5B 125.27(19) . . ? C3B C4B H4B 117.4 . . ? C5B C4B H4B 117.4 . . ? C6B C5B C4B 116.11(19) . . ? C6B C5B C17B 123.64(19) . . ? C4B C5B C17B 120.25(19) . . ? C5B C6B C7B 122.08(19) . . ? C5B C6B H6B 119.0 . . ? C7B C6B H6B 119.0 . . ? C6B C7B C2B 119.58(18) . . ? C6B C7B C8B 118.85(19) . . ? C2B C7B C8B 121.38(18) . . ? N9B C8B C7B 122.90(19) . . ? N9B C8B H8B 118.5 . . ? C7B C8B H8B 118.5 . . ? C11B C10B C15B 119.82(19) . . ? C11B C10B N9B 122.4(2) . . ? C15B C10B N9B 117.79(18) . . ? C14B C15B C10B 118.2(2) . . ? C14B C15B C16B 120.3(2) . . ? C10B C15B C16B 121.43(19) . . ? C13B C14B C15B 121.7(2) . . ? C13B C14B H14B 119.2 . . ? C15B C14B H14B 119.2 . . ? C12B C13B C14B 119.7(2) . . ? C12B C13B H13B 120.1 . . ? C14B C13B H13B 120.1 . . ? C13B C12B C11B 120.2(2) . . ? C13B C12B H12B 119.9 . . ? C11B C12B H12B 119.9 . . ? C12B C11B C10B 120.3(2) . . ? C12B C11B H11B 119.9 . . ? C10B C11B H11B 119.9 . . ? O2B C16B C15B 113.4(2) . . ? O2B C16B H16C 108.9 . . ? C15B C16B H16C 108.9 . . ? O2B C16B H16D 108.9 . . ? C15B C16B H16D 108.9 . . ? H16C C16B H16D 107.7 . . ? C22B C21B C24B 107.8(2) . . ? C22B C21B C23B 109.7(2) . . ? C24B C21B C23B 107.8(2) . . ? C22B C21B C3B 109.60(19) . . ? C24B C21B C3B 111.68(19) . . ? C23B C21B C3B 110.2(2) . . ? C19B C17B C18B 108.1(3) . . ? C19B C17B C5B 112.1(2) . . ? C18B C17B C5B 109.2(2) . . ? C19B C17B C20B 108.9(3) . . ? C18B C17B C20B 109.1(3) . . ? C5B C17B C20B 109.3(2) . . ? C21B C22B H22D 109.5 . . ? C21B C22B H22F 109.5 . . ? H22D C22B H22F 109.5 . . ? C21B C22B H22E 109.5 . . ? H22D C22B H22E 109.5 . . ? H22F C22B H22E 109.5 . . ? C21B C23B H23D 109.5 . . ? C21B C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? C21B C23B H23F 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? C21B C24B H24F 109.5 . . ? C21B C24B H24D 109.5 . . ? H24F C24B H24D 109.5 . . ? C21B C24B H24E 109.5 . . ? H24F C24B H24E 109.5 . . ? H24D C24B H24E 109.5 . . ? C17B C19B H19G 109.5 . . ? C17B C19B H19H 109.5 . . ? H19G C19B H19H 109.5 . . ? C17B C19B H19I 109.5 . . ? H19G C19B H19I 109.5 . . ? H19H C19B H19I 109.5 . . ? C17B C20B H20G 109.5 . . ? C17B C20B H20H 109.5 . . ? H20G C20B H20H 109.5 . . ? C17B C20B H20I 109.5 . . ? H20G C20B H20I 109.5 . . ? H20H C20B H20I 109.5 . . ? C17B C18B H18G 109.5 . . ? C17B C18B H18H 109.5 . . ? H18G C18B H18H 109.5 . . ? C17B C18B H18I 109.5 . . ? H18G C18B H18I 109.5 . . ? H18H C18B H18I 109.5 . . ? C8B N9B C10B 120.92(18) . . ? C16B O2B H2B 109.5 . . ? C2B O1B H1B 102.4(16) . . ? 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 O1A C2A C3A C4A -179.75(19) . . . . ? C7A C2A C3A C4A 2.5(3) . . . . ? O1A C2A C3A C21A 1.5(3) . . . . ? C7A C2A C3A C21A -176.26(19) . . . . ? C2A C3A C4A C5A -1.6(3) . . . . ? C21A C3A C4A C5A 177.2(2) . . . . ? C3A C4A C5A C6A -0.5(3) . . . . ? C3A C4A C5A C17A -177.8(2) . . . . ? C4A C5A C6A C7A 1.6(3) . . . . ? C17A C5A C6A C7A 179.0(2) . . . . ? C5A C6A C7A C2A -0.7(3) . . . . ? C5A C6A C7A C8A -173.36(19) . . . . ? O1A C2A C7A C6A -179.20(18) . . . . ? C3A C2A C7A C6A -1.5(3) . . . . ? O1A C2A C7A C8A -6.8(3) . . . . ? C3A C2A C7A C8A 170.95(18) . . . . ? C6A C7A C8A N9A 176.79(19) . . . . ? C2A C7A C8A N9A 4.3(3) . . . . ? C11A C10A C15A C14A 0.2(3) . . . . ? N9A C10A C15A C14A -179.87(18) . . . . ? C11A C10A C15A C16A -179.6(2) . . . . ? N9A C10A C15A C16A 0.3(3) . . . . ? C10A C15A C14A C13A -0.1(3) . . . . ? C16A C15A C14A C13A 179.7(2) . . . . ? C15A C14A C13A C12A 0.6(4) . . . . ? C14A C13A C12A C11A -1.2(4) . . . . ? C13A C12A C11A C10A 1.3(4) . . . . ? C15A C10A C11A C12A -0.8(3) . . . . ? N9A C10A C11A C12A 179.3(2) . . . . ? C14A C15A C16A O2A -1.6(4) . . . . ? C10A C15A C16A O2A 178.1(3) . . . . ? C14A C15A C16A O2C 24.1(4) . . . . ? C10A C15A C16A O2C -156.1(4) . . . . ? C4A C3A C21A C23A -117.7(2) . . . . ? C2A C3A C21A C23A 61.0(3) . . . . ? C4A C3A C21A C22A 1.1(3) . . . . ? C2A C3A C21A C22A 179.8(2) . . . . ? C4A C3A C21A C24A 120.8(2) . . . . ? C2A C3A C21A C24A -60.5(3) . . . . ? C6A C5A C17A C18C 11.0(7) . . . . ? C4A C5A C17A C18C -171.8(6) . . . . ? C6A C5A C17A C19C -106.9(5) . . . . ? C4A C5A C17A C19C 70.3(5) . . . . ? C6A C5A C17A C20A 172.8(3) . . . . ? C4A C5A C17A C20A -10.0(4) . . . . ? C6A C5A C17A C18A 50.6(3) . . . . ? C4A C5A C17A C18A -132.1(3) . . . . ? C6A C5A C17A C20C 136.3(6) . . . . ? C4A C5A C17A C20C -46.5(7) . . . . ? C6A C5A C17A C19A -67.7(3) . . . . ? C4A C5A C17A C19A 109.6(3) . . . . ? C7A C8A N9A C10A -172.38(17) . . . . ? C11A C10A N9A C8A -17.7(3) . . . . ? C15A C10A N9A C8A 162.35(19) . . . . ? O1B C2B C3B C4B -178.0(2) . . . . ? C7B C2B C3B C4B 0.9(3) . . . . ? O1B C2B C3B C21B 3.3(3) . . . . ? C7B C2B C3B C21B -177.8(2) . . . . ? C2B C3B C4B C5B -0.4(4) . . . . ? C21B C3B C4B C5B 178.3(2) . . . . ? C3B C4B C5B C6B -0.9(4) . . . . ? C3B C4B C5B C17B 179.5(2) . . . . ? C4B C5B C6B C7B 1.9(3) . . . . ? C17B C5B C6B C7B -178.6(2) . . . . ? C5B C6B C7B C2B -1.5(3) . . . . ? C5B C6B C7B C8B 173.6(2) . . . . ? O1B C2B C7B C6B 178.9(2) . . . . ? C3B C2B C7B C6B 0.0(3) . . . . ? O1B C2B C7B C8B 3.9(3) . . . . ? C3B C2B C7B C8B -174.9(2) . . . . ? C6B C7B C8B N9B -172.9(2) . . . . ? C2B C7B C8B N9B 2.1(3) . . . . ? C11B C10B C15B C14B 0.9(3) . . . . ? N9B C10B C15B C14B -179.10(18) . . . . ? C11B C10B C15B C16B -176.5(2) . . . . ? N9B C10B C15B C16B 3.5(3) . . . . ? C10B C15B C14B C13B -1.0(3) . . . . ? C16B C15B C14B C13B 176.4(2) . . . . ? C15B C14B C13B C12B 0.5(4) . . . . ? C14B C13B C12B C11B 0.2(4) . . . . ? C13B C12B C11B C10B -0.3(4) . . . . ? C15B C10B C11B C12B -0.3(3) . . . . ? N9B C10B C11B C12B 179.7(2) . . . . ? C14B C15B C16B O2B -41.5(3) . . . . ? C10B C15B C16B O2B 135.8(2) . . . . ? C4B C3B C21B C22B -119.7(2) . . . . ? C2B C3B C21B C22B 58.9(3) . . . . ? C4B C3B C21B C24B -0.4(4) . . . . ? C2B C3B C21B C24B 178.3(2) . . . . ? C4B C3B C21B C23B 119.4(3) . . . . ? C2B C3B C21B C23B -61.9(3) . . . . ? C6B C5B C17B C19B 1.5(4) . . . . ? C4B C5B C17B C19B -179.0(3) . . . . ? C6B C5B C17B C18B -118.4(3) . . . . ? C4B C5B C17B C18B 61.1(3) . . . . ? C6B C5B C17B C20B 122.3(3) . . . . ? C4B C5B C17B C20B -58.2(3) . . . . ? C7B C8B N9B C10B 174.35(19) . . . . ? C11B C10B N9B C8B 37.6(3) . . . . ? C15B C10B N9B C8B -142.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.284 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.075 _chemical_name_common '2,4-ditertbutyl-6-((2-hydroxymethylphenylimino)methyl) phenol' #===END data_Compound8 _database_code_depnum_ccdc_archive 'CCDC 712152' #TrackingRef '- cifs 1-8_(R2).cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-[(4-Chloro-2-hydroxymethyl-phenylimino)-methyl]-5-diethylamino-phenol ; _chemical_formula_moiety 'C18 H21 Cl1 N2 O2' _chemical_formula_sum 'C18 H21 Cl1 N2 O2' _chemical_formula_weight 332.82 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M ' P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5103(2) _cell_length_b 12.8864(4) _cell_length_c 15.2106(4) _cell_angle_alpha 97.8703(11) _cell_angle_beta 107.113(1) _cell_angle_gamma 100.4799(14) _cell_volume 1715.51(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9193 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_special_details ; # Refinement with 15 Restrains (explanation): Due to the presence of two molecules crystallographically independent in the crystal, the C-N and C-C bond distances of diethylamino groups (one of them disordered over two positions) of both molecules were treated with the DFIX instruction according to the C-C bond(1.54 %A) and C-N bonds (1.46 %A), which are typical bond distances occurring in this fragment. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.145589E-1 _diffrn_orient_matrix_ub_12 0.442597E-1 _diffrn_orient_matrix_ub_13 -0.471285E-1 _diffrn_orient_matrix_ub_21 0.317436E-1 _diffrn_orient_matrix_ub_22 0.670909E-1 _diffrn_orient_matrix_ub_23 0.495896E-1 _diffrn_orient_matrix_ub_31 0.107658 _diffrn_orient_matrix_ub_32 -0.58839E-2 _diffrn_orient_matrix_ub_33 0.159495E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_unetI/netI 0.0709 _diffrn_reflns_number 14135 _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 -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.937 _reflns_number_total 7334 _reflns_number_gt 4472 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1622P)^2^+0.2099P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 7334 _refine_ls_number_parameters 454 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.1352 _refine_ls_R_factor_gt 0.0858 _refine_ls_wR_factor_ref 0.2786 _refine_ls_wR_factor_gt 0.238 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.479 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.123 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 H2A H 0.825(4) 0.994(3) 0.123(3) 0.067(12) Uiso 1 1 d . . . H2B H 1.088(5) 1.179(3) -0.052(3) 0.085(12) Uiso 1 1 d . . . H9B H 0.669(4) 0.957(3) -0.077(2) 0.069(10) Uiso 1 1 d . . . C2B C 0.6020(3) 0.8200(2) 0.0057(2) 0.0507(7) Uani 1 1 d . . . C3B C 0.5848(3) 0.7399(3) 0.0564(2) 0.0597(8) Uani 1 1 d . . . H3B H 0.671 0.7245 0.0949 0.072 Uiso 1 1 calc R . . C4B C 0.4418(3) 0.6808(2) 0.0520(2) 0.0576(7) Uani 1 1 d . . . C5B C 0.3113(3) 0.7040(2) -0.0083(2) 0.0572(7) Uani 1 1 d . . . H5B H 0.2157 0.6669 -0.0117 0.069 Uiso 1 1 calc R . . C6B C 0.3245(3) 0.7793(2) -0.0605(2) 0.0531(7) Uani 1 1 d . . . H6B H 0.237 0.792 -0.1003 0.064 Uiso 1 1 calc R . . C7B C 0.4672(3) 0.8398(2) -0.0571(2) 0.0452(6) Uani 1 1 d . . . C8B C 0.4727(3) 0.9151(2) -0.1128(2) 0.0490(7) Uani 1 1 d . . . H8B H 0.3813 0.9241 -0.151 0.059 Uiso 1 1 calc R . . C10B C 0.6113(3) 1.0519(2) -0.17341(19) 0.0455(6) Uani 1 1 d . . . C11B C 0.4850(3) 1.0643(2) -0.2422(2) 0.0575(7) Uani 1 1 d . . . H11B H 0.3897 1.0236 -0.249 0.069 Uiso 1 1 calc R . . C12B C 0.4991(4) 1.1358(2) -0.3002(2) 0.0632(8) Uani 1 1 d . . . H12B H 0.4145 1.1444 -0.3457 0.076 Uiso 1 1 calc R . . C13B C 0.6428(4) 1.1948(2) -0.2892(2) 0.0577(7) Uani 1 1 d . . . C14B C 0.7679(3) 1.1861(2) -0.2201(2) 0.0536(7) Uani 1 1 d . . . H14B H 0.8626 1.2278 -0.2134 0.064 Uiso 1 1 calc R . . C15B C 0.7546(3) 1.1154(2) -0.1602(2) 0.0458(6) Uani 1 1 d . . . C16B C 0.8906(3) 1.1097(2) -0.0811(2) 0.0547(7) Uani 1 1 d . . . H16C H 0.8662 1.1126 -0.0233 0.066 Uiso 1 1 calc R . . H16D H 0.9188 1.0422 -0.0948 0.066 Uiso 1 1 calc R . . C17B C 0.5534(5) 0.5525(4) 0.1427(3) 0.0970(13) Uani 1 1 d DU . . H17D H 0.6267 0.561 0.1098 0.116 Uiso 1 1 calc R . . H17C H 0.5168 0.4763 0.1395 0.116 Uiso 1 1 calc R . . C18B C 0.6252(7) 0.6130(5) 0.2455(3) 0.133(2) Uani 1 1 d D . . H18E H 0.642 0.6892 0.2479 0.2 Uiso 1 1 calc R . . H18F H 0.7201 0.595 0.2728 0.2 Uiso 1 1 calc R . . H18D H 0.5585 0.5925 0.28 0.2 Uiso 1 1 calc R . . C19B C 0.2818(4) 0.5529(3) 0.1115(2) 0.0743(10) Uani 1 1 d D . . H19E H 0.2202 0.6055 0.1075 0.089 Uiso 1 1 calc R . . H19F H 0.3007 0.535 0.1732 0.089 Uiso 1 1 calc R . . C20B C 0.1945(5) 0.4509(3) 0.0363(3) 0.0992(14) Uani 1 1 d D . . H20G H 0.1731 0.4686 -0.0249 0.149 Uiso 1 1 calc R . . H20I H 0.1012 0.4221 0.0462 0.149 Uiso 1 1 calc R . . H20H H 0.2546 0.3983 0.0405 0.149 Uiso 1 1 calc R . . N1B N 0.4268(3) 0.6008(3) 0.1007(3) 0.0800(9) Uani 1 1 d U . . N9B N 0.5991(2) 0.97592(18) -0.11590(17) 0.0469(6) Uani 1 1 d . . . O1B O 0.7342(2) 0.87682(17) 0.01204(16) 0.0614(6) Uani 1 1 d . . . O2B O 1.0118(3) 1.19632(19) -0.0700(2) 0.0914(10) Uani 1 1 d . . . Cl1B Cl 0.66244(12) 1.28254(8) -0.36441(7) 0.0852(4) Uani 1 1 d . . . C2A C 0.9620(3) 0.8061(3) 0.4722(2) 0.0615(8) Uani 1 1 d . . . C3A C 0.8916(4) 0.7248(3) 0.5066(3) 0.0726(9) Uani 1 1 d . . . H3A H 0.7892 0.6934 0.4763 0.087 Uiso 1 1 calc R . . C4A C 0.9684(4) 0.6888(3) 0.5844(3) 0.0701(9) Uani 1 1 d . A . C5A C 1.1235(4) 0.7405(3) 0.6306(3) 0.0795(10) Uani 1 1 d . . . H5A H 1.1781 0.721 0.6848 0.095 Uiso 1 1 calc R . . C6A C 1.1917(4) 0.8193(3) 0.5947(3) 0.0712(9) Uani 1 1 d . . . H6A H 1.294 0.8509 0.6252 0.085 Uiso 1 1 calc R . . C7A C 1.1181(3) 0.8550(2) 0.5159(2) 0.0536(7) Uani 1 1 d . . . C8A C 1.1938(3) 0.9368(2) 0.4807(2) 0.0574(8) Uani 1 1 d . . . H8A H 1.2963 0.9669 0.5116 0.069 Uiso 1 1 calc R . . C10A C 1.1980(3) 1.0514(2) 0.3706(2) 0.0528(7) Uani 1 1 d . . . C11A C 1.3472(4) 1.1109(3) 0.4135(3) 0.0687(9) Uani 1 1 d . . . H11A H 1.4063 1.0974 0.4695 0.082 Uiso 1 1 calc R . . C12A C 1.4069(4) 1.1895(3) 0.3730(3) 0.0721(9) Uani 1 1 d . . . H12A H 1.5057 1.2299 0.4023 0.087 Uiso 1 1 calc R . . C13A C 1.3214(4) 1.2084(2) 0.2898(2) 0.0620(8) Uani 1 1 d . . . C14A C 1.1716(4) 1.1507(2) 0.2469(2) 0.0588(8) Uani 1 1 d . . . H14A H 1.1134 1.1648 0.1909 0.071 Uiso 1 1 calc R . . C15A C 1.1098(3) 1.0728(2) 0.2872(2) 0.0508(7) Uani 1 1 d . . . C16A C 0.9481(3) 1.0098(3) 0.2422(2) 0.0616(8) Uani 1 1 d . . . H16A H 0.9464 0.9342 0.2247 0.074 Uiso 1 1 calc R . . H16B H 0.8951 1.0163 0.2876 0.074 Uiso 1 1 calc R . . C17A C 0.7398(4) 0.5544(3) 0.5704(3) 0.0897(12) Uani 1 1 d D A . H17B H 0.682 0.6067 0.5507 0.108 Uiso 1 1 calc R . . H17A H 0.6998 0.52 0.6137 0.108 Uiso 1 1 calc R . . C18A C 0.7220(7) 0.4694(3) 0.4845(3) 0.131(2) Uani 1 1 d D . . H18C H 0.7695 0.5022 0.4443 0.197 Uiso 1 1 calc R . . H18B H 0.6164 0.4398 0.4507 0.197 Uiso 1 1 calc R . . H18A H 0.7689 0.4129 0.5047 0.197 Uiso 1 1 calc R . . C19A C 0.9883(10) 0.5433(7) 0.6704(6) 0.084(4) Uani 0.428(12) 1 d PD A 1 H19A H 1.0905 0.5601 0.6678 0.1 Uiso 0.428(12) 1 calc PR A 1 H19B H 0.9439 0.4674 0.6434 0.1 Uiso 0.428(12) 1 calc PR A 1 C20A C 0.9908(16) 0.5687(15) 0.7730(7) 0.127(6) Uani 0.428(12) 1 d PD A 1 H20A H 1.0369 0.6436 0.7993 0.19 Uiso 0.428(12) 1 calc PR A 1 H20C H 1.048 0.5255 0.8088 0.19 Uiso 0.428(12) 1 calc PR A 1 H20B H 0.8891 0.5528 0.7746 0.19 Uiso 0.428(12) 1 calc PR A 1 C19C C 0.9540(11) 0.6017(7) 0.7241(8) 0.103(3) Uani 0.572(12) 1 d PD A 2 H19C H 1.0171 0.6699 0.7632 0.124 Uiso 0.572(12) 1 calc PR A 2 H19D H 0.8698 0.5794 0.7463 0.124 Uiso 0.572(12) 1 calc PR A 2 C20C C 1.0458(13) 0.5150(9) 0.7222(11) 0.142(5) Uani 0.572(12) 1 d PD A 2 H20F H 0.985 0.4524 0.6755 0.213 Uiso 0.572(12) 1 calc PR A 2 H20D H 1.0748 0.4957 0.7827 0.213 Uiso 0.572(12) 1 calc PR A 2 H20E H 1.1348 0.5427 0.7073 0.213 Uiso 0.572(12) 1 calc PR A 2 N9A N 1.1260(3) 0.9707(2) 0.40780(19) 0.0592(7) Uani 1 1 d . . . N1A N 0.8980(4) 0.6091(3) 0.6179(3) 0.1005(12) Uani 1 1 d D . . O1A O 0.8797(3) 0.8378(2) 0.3978(2) 0.0945(9) Uani 1 1 d D . . O2A O 0.8716(3) 1.0455(2) 0.1618(2) 0.0764(7) Uani 1 1 d . . . Cl1A Cl 1.39949(12) 1.30590(8) 0.23854(8) 0.0895(4) Uani 1 1 d . . . H1A H 0.942(4) 0.892(2) 0.392(3) 0.107 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2B 0.0372(12) 0.0562(16) 0.0551(17) 0.0105(13) 0.0126(12) 0.0067(11) C3B 0.0445(14) 0.0710(19) 0.066(2) 0.0291(15) 0.0140(14) 0.0151(13) C4B 0.0544(15) 0.0589(17) 0.065(2) 0.0220(14) 0.0233(15) 0.0121(13) C5B 0.0422(13) 0.0604(17) 0.069(2) 0.0191(15) 0.0196(14) 0.0043(12) C6B 0.0376(12) 0.0607(17) 0.0603(18) 0.0191(14) 0.0135(12) 0.0085(11) C7B 0.0365(12) 0.0479(14) 0.0494(16) 0.0089(12) 0.0130(11) 0.0081(10) C8B 0.0382(12) 0.0532(15) 0.0522(17) 0.0095(13) 0.0124(12) 0.0072(11) C10B 0.0415(12) 0.0453(14) 0.0468(16) 0.0094(11) 0.0119(11) 0.0069(10) C11B 0.0420(13) 0.0638(17) 0.0562(18) 0.0172(14) 0.0050(13) 0.0015(12) C12B 0.0578(16) 0.0650(19) 0.0536(19) 0.0174(15) 0.0020(14) 0.0052(14) C13B 0.0644(17) 0.0504(16) 0.0594(19) 0.0159(13) 0.0220(15) 0.0097(13) C14B 0.0491(14) 0.0450(14) 0.067(2) 0.0092(13) 0.0237(14) 0.0051(11) C15B 0.0401(12) 0.0420(13) 0.0539(17) 0.0056(11) 0.0165(12) 0.0070(10) C16B 0.0366(12) 0.0504(15) 0.070(2) 0.0093(14) 0.0122(13) 0.0040(11) C17B 0.099(3) 0.094(3) 0.104(4) 0.042(3) 0.036(3) 0.016(2) C18B 0.131(5) 0.152(5) 0.113(5) 0.024(4) 0.038(4) 0.027(4) C19B 0.082(2) 0.069(2) 0.078(2) 0.0284(18) 0.037(2) 0.0060(17) C20B 0.114(3) 0.077(3) 0.104(3) 0.014(2) 0.040(3) 0.009(2) N1B 0.0645(16) 0.086(2) 0.101(2) 0.0527(18) 0.0299(17) 0.0163(15) N9B 0.0358(10) 0.0525(13) 0.0485(14) 0.0152(10) 0.0087(10) 0.0057(9) O1B 0.0354(9) 0.0747(13) 0.0684(14) 0.0270(11) 0.0089(9) 0.0032(9) O2B 0.0379(11) 0.0630(14) 0.150(3) 0.0353(15) 0.0000(14) -0.0034(10) Cl1B 0.1007(7) 0.0765(6) 0.0804(7) 0.0401(5) 0.0289(6) 0.0086(5) C2A 0.0512(15) 0.0645(18) 0.058(2) 0.0175(15) 0.0052(14) 0.0060(14) C3A 0.0550(17) 0.069(2) 0.080(3) 0.0197(18) 0.0096(17) -0.0038(15) C4A 0.070(2) 0.0591(19) 0.076(2) 0.0236(16) 0.0165(18) 0.0071(15) C5A 0.073(2) 0.073(2) 0.080(3) 0.0307(19) 0.0047(19) 0.0112(17) C6A 0.0544(16) 0.066(2) 0.078(2) 0.0185(17) 0.0009(16) 0.0073(15) C7A 0.0506(15) 0.0488(15) 0.0542(18) 0.0079(13) 0.0097(13) 0.0079(12) C8A 0.0455(14) 0.0519(16) 0.063(2) 0.0052(14) 0.0075(14) 0.0041(12) C10A 0.0481(14) 0.0518(15) 0.0534(18) 0.0077(13) 0.0132(13) 0.0075(12) C11A 0.0529(16) 0.072(2) 0.066(2) 0.0167(16) 0.0061(15) -0.0014(15) C12A 0.0532(16) 0.0647(19) 0.082(3) 0.0114(17) 0.0122(17) -0.0072(14) C13A 0.0670(18) 0.0474(16) 0.071(2) 0.0076(14) 0.0287(17) 0.0046(13) C14A 0.0650(17) 0.0517(16) 0.0566(19) 0.0091(14) 0.0173(15) 0.0115(14) C15A 0.0457(13) 0.0475(14) 0.0541(18) 0.0025(12) 0.0125(13) 0.0106(11) C16A 0.0462(14) 0.0669(19) 0.066(2) 0.0139(15) 0.0103(14) 0.0113(13) C17A 0.093(3) 0.084(3) 0.098(3) 0.027(2) 0.047(2) 0.001(2) C18A 0.189(6) 0.081(3) 0.129(5) 0.015(3) 0.082(5) -0.002(3) C19A 0.081(6) 0.078(7) 0.094(8) 0.051(6) 0.021(6) 0.012(5) C20A 0.096(9) 0.177(16) 0.087(9) 0.069(10) -0.003(7) 0.003(9) C19C 0.117(7) 0.098(6) 0.104(9) 0.034(6) 0.046(7) 0.022(5) C20C 0.134(9) 0.152(10) 0.167(14) 0.072(9) 0.051(9) 0.064(8) N9A 0.0504(13) 0.0555(14) 0.0606(17) 0.0095(12) 0.0104(12) 0.0001(11) N1A 0.094(2) 0.090(2) 0.099(3) 0.051(2) 0.006(2) -0.0060(18) O1A 0.0581(13) 0.105(2) 0.095(2) 0.0519(16) -0.0078(14) -0.0124(13) O2A 0.0631(14) 0.0735(16) 0.0751(18) 0.0183(14) -0.0040(13) 0.0153(12) Cl1A 0.1024(7) 0.0714(6) 0.0936(8) 0.0224(5) 0.0429(6) -0.0046(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2B O1B 1.303(3) . ? C2B C3B 1.385(4) . ? C2B C7B 1.444(4) . ? C3B C4B 1.410(4) . ? C3B H3B 0.93 . ? C4B N1B 1.360(4) . ? C4B C5B 1.418(4) . ? C5B C6B 1.347(4) . ? C5B H5B 0.93 . ? C6B C7B 1.420(4) . ? C6B H6B 0.93 . ? C7B C8B 1.377(4) . ? C8B N9B 1.328(3) . ? C8B H8B 0.93 . ? C10B C11B 1.392(4) . ? C10B C15B 1.398(4) . ? C10B N9B 1.411(4) . ? C11B C12B 1.376(4) . ? C11B H11B 0.93 . ? C12B C13B 1.387(4) . ? C12B H12B 0.93 . ? C13B C14B 1.370(4) . ? C13B Cl1B 1.740(3) . ? C14B C15B 1.389(4) . ? C14B H14B 0.93 . ? C15B C16B 1.506(4) . ? C16B O2B 1.403(3) . ? C16B H16C 0.97 . ? C16B H16D 0.97 . ? C17B N1B 1.475(5) . ? C17B C18B 1.538(3) . ? C17B H17D 0.97 . ? C17B H17C 0.97 . ? C18B H18E 0.96 . ? C18B H18F 0.96 . ? C18B H18D 0.96 . ? C19B N1B 1.469(4) . ? C19B C20B 1.536(3) . ? C19B H19E 0.97 . ? C19B H19F 0.97 . ? C20B H20G 0.96 . ? C20B H20I 0.96 . ? C20B H20H 0.96 . ? N9B H9B 0.85(3) . ? O2B H2B 0.78(4) . ? C2A O1A 1.335(4) . ? C2A C3A 1.386(5) . ? C2A C7A 1.416(4) . ? C3A C4A 1.384(5) . ? C3A H3A 0.93 . ? C4A N1A 1.363(5) . ? C4A C5A 1.420(5) . ? C5A C6A 1.368(5) . ? C5A H5A 0.93 . ? C6A C7A 1.384(5) . ? C6A H6A 0.93 . ? C7A C8A 1.422(4) . ? C8A N9A 1.285(4) . ? C8A H8A 0.93 . ? C10A C15A 1.394(4) . ? C10A C11A 1.396(4) . ? C10A N9A 1.415(4) . ? C11A C12A 1.377(5) . ? C11A H11A 0.93 . ? C12A C13A 1.368(5) . ? C12A H12A 0.93 . ? C13A C14A 1.394(5) . ? C13A Cl1A 1.735(3) . ? C14A C15A 1.377(4) . ? C14A H14A 0.93 . ? C15A C16A 1.506(4) . ? C16A O2A 1.410(4) . ? C16A H16A 0.97 . ? C16A H16B 0.97 . ? C17A N1A 1.455(3) . ? C17A C18A 1.531(3) . ? C17A H17B 0.97 . ? C17A H17A 0.97 . ? C18A H18C 0.96 . ? C18A H18B 0.96 . ? C18A H18A 0.96 . ? C19A N1A 1.464(3) . ? C19A C20A 1.542(3) . ? C19A H19A 0.97 . ? C19A H19B 0.97 . ? C20A H20A 0.96 . ? C20A H20C 0.96 . ? C20A H20B 0.96 . ? C19C C20C 1.541(3) . ? C19C N1A 1.567(12) . ? C19C H19C 0.97 . ? C19C H19D 0.97 . ? C20C H20F 0.96 . ? C20C H20D 0.96 . ? C20C H20E 0.96 . ? O1A H1A 0.863(19) . ? O2A H2A 0.78(4) . ? 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 O1B C2B C3B 122.6(3) . . ? O1B C2B C7B 119.4(3) . . ? C3B C2B C7B 118.0(2) . . ? C2B C3B C4B 122.8(3) . . ? C2B C3B H3B 118.6 . . ? C4B C3B H3B 118.6 . . ? N1B C4B C3B 122.0(3) . . ? N1B C4B C5B 119.9(3) . . ? C3B C4B C5B 118.0(3) . . ? C6B C5B C4B 120.6(3) . . ? C6B C5B H5B 119.7 . . ? C4B C5B H5B 119.7 . . ? C5B C6B C7B 122.3(3) . . ? C5B C6B H6B 118.9 . . ? C7B C6B H6B 118.9 . . ? C8B C7B C6B 119.3(2) . . ? C8B C7B C2B 122.4(2) . . ? C6B C7B C2B 118.3(3) . . ? N9B C8B C7B 124.7(3) . . ? N9B C8B H8B 117.6 . . ? C7B C8B H8B 117.6 . . ? C11B C10B C15B 120.0(3) . . ? C11B C10B N9B 121.6(2) . . ? C15B C10B N9B 118.4(2) . . ? C12B C11B C10B 121.0(3) . . ? C12B C11B H11B 119.5 . . ? C10B C11B H11B 119.5 . . ? C11B C12B C13B 118.4(3) . . ? C11B C12B H12B 120.8 . . ? C13B C12B H12B 120.8 . . ? C14B C13B C12B 121.5(3) . . ? C14B C13B Cl1B 119.8(2) . . ? C12B C13B Cl1B 118.7(3) . . ? C13B C14B C15B 120.6(3) . . ? C13B C14B H14B 119.7 . . ? C15B C14B H14B 119.7 . . ? C14B C15B C10B 118.4(3) . . ? C14B C15B C16B 120.8(2) . . ? C10B C15B C16B 120.8(3) . . ? O2B C16B C15B 109.6(3) . . ? O2B C16B H16C 109.7 . . ? C15B C16B H16C 109.7 . . ? O2B C16B H16D 109.7 . . ? C15B C16B H16D 109.7 . . ? H16C C16B H16D 108.2 . . ? N1B C17B C18B 106.0(4) . . ? N1B C17B H17D 110.5 . . ? C18B C17B H17D 110.5 . . ? N1B C17B H17C 110.5 . . ? C18B C17B H17C 110.5 . . ? H17D C17B H17C 108.7 . . ? C17B C18B H18E 109.5 . . ? C17B C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C17B C18B H18D 109.5 . . ? H18E C18B H18D 109.5 . . ? H18F C18B H18D 109.5 . . ? N1B C19B C20B 112.3(3) . . ? N1B C19B H19E 109.2 . . ? C20B C19B H19E 109.2 . . ? N1B C19B H19F 109.2 . . ? C20B C19B H19F 109.2 . . ? H19E C19B H19F 107.9 . . ? C19B C20B H20G 109.5 . . ? C19B C20B H20I 109.5 . . ? H20G C20B H20I 109.5 . . ? C19B C20B H20H 109.5 . . ? H20G C20B H20H 109.5 . . ? H20I C20B H20H 109.5 . . ? C4B N1B C19B 122.5(3) . . ? C4B N1B C17B 122.2(3) . . ? C19B N1B C17B 115.2(3) . . ? C8B N9B C10B 127.0(2) . . ? C8B N9B H9B 104(2) . . ? C10B N9B H9B 129(2) . . ? C16B O2B H2B 110(3) . . ? O1A C2A C3A 118.7(3) . . ? O1A C2A C7A 120.8(3) . . ? C3A C2A C7A 120.4(3) . . ? C4A C3A C2A 122.2(3) . . ? C4A C3A H3A 118.9 . . ? C2A C3A H3A 118.9 . . ? N1A C4A C3A 121.8(3) . . ? N1A C4A C5A 120.7(3) . . ? C3A C4A C5A 117.5(3) . . ? C6A C5A C4A 119.4(3) . . ? C6A C5A H5A 120.3 . . ? C4A C5A H5A 120.3 . . ? C5A C6A C7A 124.1(3) . . ? C5A C6A H6A 118 . . ? C7A C6A H6A 118 . . ? C6A C7A C2A 116.3(3) . . ? C6A C7A C8A 122.1(3) . . ? C2A C7A C8A 121.5(3) . . ? N9A C8A C7A 122.5(3) . . ? N9A C8A H8A 118.8 . . ? C7A C8A H8A 118.8 . . ? C15A C10A C11A 119.6(3) . . ? C15A C10A N9A 116.3(2) . . ? C11A C10A N9A 124.1(3) . . ? C12A C11A C10A 120.0(3) . . ? C12A C11A H11A 120 . . ? C10A C11A H11A 120 . . ? C13A C12A C11A 120.3(3) . . ? C13A C12A H12A 119.9 . . ? C11A C12A H12A 119.9 . . ? C12A C13A C14A 120.3(3) . . ? C12A C13A Cl1A 119.7(3) . . ? C14A C13A Cl1A 120.0(3) . . ? C15A C14A C13A 120.0(3) . . ? C15A C14A H14A 120 . . ? C13A C14A H14A 120 . . ? C14A C15A C10A 119.7(3) . . ? C14A C15A C16A 120.9(3) . . ? C10A C15A C16A 119.4(3) . . ? O2A C16A C15A 112.4(3) . . ? O2A C16A H16A 109.1 . . ? C15A C16A H16A 109.1 . . ? O2A C16A H16B 109.1 . . ? C15A C16A H16B 109.1 . . ? H16A C16A H16B 107.9 . . ? N1A C17A C18A 111.1(4) . . ? N1A C17A H17B 109.4 . . ? C18A C17A H17B 109.4 . . ? N1A C17A H17A 109.4 . . ? C18A C17A H17A 109.4 . . ? H17B C17A H17A 108 . . ? C17A C18A H18C 109.5 . . ? C17A C18A H18B 109.5 . . ? H18C C18A H18B 109.5 . . ? C17A C18A H18A 109.5 . . ? H18C C18A H18A 109.5 . . ? H18B C18A H18A 109.5 . . ? N1A C19A C20A 107.7(9) . . ? N1A C19A H19A 110.2 . . ? C20A C19A H19A 110.2 . . ? N1A C19A H19B 110.2 . . ? C20A C19A H19B 110.2 . . ? H19A C19A H19B 108.5 . . ? C20C C19C N1A 101.6(9) . . ? C20C C19C H19C 111.4 . . ? N1A C19C H19C 111.4 . . ? C20C C19C H19D 111.4 . . ? N1A C19C H19D 111.4 . . ? H19C C19C H19D 109.3 . . ? C19C C20C H20F 109.5 . . ? C19C C20C H20D 109.5 . . ? H20F C20C H20D 109.5 . . ? C19C C20C H20E 109.5 . . ? H20F C20C H20E 109.5 . . ? H20D C20C H20E 109.5 . . ? C8A N9A C10A 124.0(3) . . ? C4A N1A C17A 121.2(3) . . ? C4A N1A C19A 118.7(5) . . ? C17A N1A C19A 113.9(5) . . ? C4A N1A C19C 121.8(5) . . ? C17A N1A C19C 112.8(5) . . ? C19A N1A C19C 46.1(5) . . ? C2A O1A H1A 103(3) . . ? C16A O2A H2A 108(3) . . ? 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 O1B C2B C3B C4B 177.8(3) . . . . ? C7B C2B C3B C4B -2.8(5) . . . . ? C2B C3B C4B N1B 178.6(3) . . . . ? C2B C3B C4B C5B 1.1(5) . . . . ? N1B C4B C5B C6B -176.6(3) . . . . ? C3B C4B C5B C6B 0.9(5) . . . . ? C4B C5B C6B C7B -1.1(5) . . . . ? C5B C6B C7B C8B 179.6(3) . . . . ? C5B C6B C7B C2B -0.7(4) . . . . ? O1B C2B C7B C8B 1.7(4) . . . . ? C3B C2B C7B C8B -177.8(3) . . . . ? O1B C2B C7B C6B -178.0(3) . . . . ? C3B C2B C7B C6B 2.5(4) . . . . ? C6B C7B C8B N9B -179.6(3) . . . . ? C2B C7B C8B N9B 0.7(4) . . . . ? C15B C10B C11B C12B 2.3(4) . . . . ? N9B C10B C11B C12B -177.5(3) . . . . ? C10B C11B C12B C13B 0.6(5) . . . . ? C11B C12B C13B C14B -2.5(5) . . . . ? C11B C12B C13B Cl1B 178.1(2) . . . . ? C12B C13B C14B C15B 1.5(4) . . . . ? Cl1B C13B C14B C15B -179.1(2) . . . . ? C13B C14B C15B C10B 1.4(4) . . . . ? C13B C14B C15B C16B -176.8(3) . . . . ? C11B C10B C15B C14B -3.3(4) . . . . ? N9B C10B C15B C14B 176.5(2) . . . . ? C11B C10B C15B C16B 174.9(3) . . . . ? N9B C10B C15B C16B -5.3(4) . . . . ? C14B C15B C16B O2B 11.1(4) . . . . ? C10B C15B C16B O2B -167.0(3) . . . . ? C3B C4B N1B C19B 168.0(3) . . . . ? C5B C4B N1B C19B -14.6(5) . . . . ? C3B C4B N1B C17B -15.0(6) . . . . ? C5B C4B N1B C17B 162.5(3) . . . . ? C20B C19B N1B C4B 94.1(4) . . . . ? C20B C19B N1B C17B -83.1(4) . . . . ? C18B C17B N1B C4B 95.3(5) . . . . ? C18B C17B N1B C19B -87.5(4) . . . . ? C7B C8B N9B C10B 178.1(2) . . . . ? C11B C10B N9B C8B -6.1(4) . . . . ? C15B C10B N9B C8B 174.1(2) . . . . ? O1A C2A C3A C4A -178.8(3) . . . . ? C7A C2A C3A C4A 0.7(6) . . . . ? C2A C3A C4A N1A 179.7(4) . . . . ? C2A C3A C4A C5A 1.8(6) . . . . ? N1A C4A C5A C6A 179.2(4) . . . . ? C3A C4A C5A C6A -2.9(6) . . . . ? C4A C5A C6A C7A 1.6(6) . . . . ? C5A C6A C7A C2A 0.9(5) . . . . ? C5A C6A C7A C8A -179.6(3) . . . . ? O1A C2A C7A C6A 177.5(3) . . . . ? C3A C2A C7A C6A -2.0(5) . . . . ? O1A C2A C7A C8A -2.0(5) . . . . ? C3A C2A C7A C8A 178.5(3) . . . . ? C6A C7A C8A N9A -179.6(3) . . . . ? C2A C7A C8A N9A -0.1(5) . . . . ? C15A C10A C11A C12A -0.6(5) . . . . ? N9A C10A C11A C12A -178.6(3) . . . . ? C10A C11A C12A C13A -1.1(5) . . . . ? C11A C12A C13A C14A 2.0(5) . . . . ? C11A C12A C13A Cl1A -178.7(3) . . . . ? C12A C13A C14A C15A -1.2(5) . . . . ? Cl1A C13A C14A C15A 179.6(2) . . . . ? C13A C14A C15A C10A -0.6(4) . . . . ? C13A C14A C15A C16A 179.8(3) . . . . ? C11A C10A C15A C14A 1.4(4) . . . . ? N9A C10A C15A C14A 179.6(2) . . . . ? C11A C10A C15A C16A -178.9(3) . . . . ? N9A C10A C15A C16A -0.7(4) . . . . ? C14A C15A C16A O2A -4.0(4) . . . . ? C10A C15A C16A O2A 176.3(3) . . . . ? C7A C8A N9A C10A -179.6(3) . . . . ? C15A C10A N9A C8A 175.5(3) . . . . ? C11A C10A N9A C8A -6.4(5) . . . . ? C3A C4A N1A C17A 3.2(6) . . . . ? C5A C4A N1A C17A -179.1(4) . . . . ? C3A C4A N1A C19A 153.9(6) . . . . ? C5A C4A N1A C19A -28.3(7) . . . . ? C3A C4A N1A C19C -152.2(5) . . . . ? C5A C4A N1A C19C 25.5(6) . . . . ? C18A C17A N1A C4A 78.8(5) . . . . ? C18A C17A N1A C19A -73.2(6) . . . . ? C18A C17A N1A C19C -123.8(5) . . . . ? C20A C19A N1A C4A 112.9(8) . . . . ? C20A C19A N1A C17A -94.3(9) . . . . ? C20A C19A N1A C19C 5.0(9) . . . . ? C20C C19C N1A C4A -99.5(7) . . . . ? C20C C19C N1A C17A 103.2(7) . . . . ? C20C C19C N1A C19A 1.3(8) . . . . ? # END of CIF _chemical_name_common ;2-((4-Chloro-2-hydroxymethyl-phenylimino)-methyl)-5- diethylamino-phenol ; #===END #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_Compound3 _database_code_depnum_ccdc_archive 'CCDC 712153' #TrackingRef '- cifs 1-8_(R2).cif' _audit_creation_date 2010-07-20T23:29:25-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (1R,2S)-2-[(2-hydroxy-1,2-diphenyl-ethylimino)-methyl]-phenol ; _chemical_formula_moiety 'C21 H19 N1 O2' _chemical_formula_sum 'C21 H19 N1 O2' _chemical_formula_weight 317.37 _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.1478(2) _cell_length_b 7.5477(2) _cell_length_c 36.07980(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1674.17(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4678 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_special_details ; # Use of one restrain (Explanation): The hydrogens attached to oxygen atoms were found on the Fourier map, but the O1-H1 bond distance refined for an abnormal bond distance 1.16(4)\%A, a DFIX 0.84 instrucction was applied to set the bond distance close to O-H typical values as the fourier map clearly indicates. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.874791E-1 _diffrn_orient_matrix_ub_12 -0.110313 _diffrn_orient_matrix_ub_13 -0.00367 _diffrn_orient_matrix_ub_21 0.133882 _diffrn_orient_matrix_ub_22 -0.732058E-1 _diffrn_orient_matrix_ub_23 0.36398E-2 _diffrn_orient_matrix_ub_31 -0.296861E-1 _diffrn_orient_matrix_ub_32 -0.50825E-2 _diffrn_orient_matrix_ub_33 0.272301E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_unetI/netI 0.0705 _diffrn_reflns_number 4795 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 46 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.882 _diffrn_measured_fraction_theta_max 0.869 _reflns_number_total 1958 _reflns_number_gt 1312 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0841P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 1958 _refine_ls_number_parameters 223 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0940 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1488 _refine_ls_wR_factor_gt 0.1158 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_abs_structure_details ; The light-atom structure prevented a useful absolute structure parameter. However, the chirality of the molecule is completely reliable by considering the enantiomeric purity of the starting material, (1S,2R)-2-amino-1,2-diphenyletanol. The Friedel-pairs reflections were merged in the refinement by using MERG4, Flack H D (1983), Acta Cryst. A39, 876-881. ; _refine_ls_abs_structure_Flack -10(10) _refine_diff_density_max 0.200 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.063 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.4549(5) 0.3070(4) 0.44591(10) 0.0416(8) Uani 1 1 d . . . C3 C 0.3167(6) 0.3591(5) 0.47426(10) 0.0505(9) Uani 1 1 d . . . H3 H 0.1815 0.3053 0.4769 0.061 Uiso 1 1 calc R . . C4 C 0.3787(7) 0.4903(5) 0.49859(12) 0.0558(10) Uani 1 1 d . . . H4 H 0.2845 0.5251 0.5174 0.067 Uiso 1 1 calc R . . C5 C 0.5817(7) 0.5716(5) 0.49526(10) 0.0561(10) Uani 1 1 d . . . H5 H 0.6233 0.6599 0.5118 0.067 Uiso 1 1 calc R . . C6 C 0.7182(6) 0.5200(4) 0.46754(11) 0.0490(9) Uani 1 1 d . . . H6 H 0.8528 0.5751 0.4652 0.059 Uiso 1 1 calc R . . C7 C 0.6610(5) 0.3866(4) 0.44258(9) 0.0382(8) Uani 1 1 d . . . C8 C 0.8106(6) 0.3271(4) 0.41431(9) 0.0413(8) Uani 1 1 d . . . H8 H 0.947 0.3798 0.4129 0.05 Uiso 1 1 calc R . . C10 C 0.9307(5) 0.1397(4) 0.36601(10) 0.0423(8) Uani 1 1 d . . . H10 H 1.0617 0.2108 0.3702 0.051 Uiso 1 1 calc R . . C11 C 0.9878(5) -0.0550(5) 0.37569(9) 0.0436(8) Uani 1 1 d . . . H11 H 1.1155 -0.0895 0.3611 0.052 Uiso 1 1 calc R . . C12 C 0.8654(6) 0.1649(4) 0.32547(9) 0.0402(8) Uani 1 1 d . . . C13 C 1.0150(6) 0.2339(5) 0.30074(11) 0.0523(9) Uani 1 1 d . . . H13 H 1.154 0.2619 0.3091 0.063 Uiso 1 1 calc R . . C14 C 0.9630(7) 0.2620(6) 0.26408(11) 0.0607(11) Uani 1 1 d . . . H14 H 1.0656 0.3098 0.248 0.073 Uiso 1 1 calc R . . C15 C 0.7564(8) 0.2189(6) 0.25117(11) 0.0597(11) Uani 1 1 d . . . H15 H 0.7197 0.2377 0.2265 0.072 Uiso 1 1 calc R . . C16 C 0.6068(7) 0.1479(5) 0.27546(12) 0.0572(10) Uani 1 1 d . . . H16 H 0.4693 0.1167 0.2669 0.069 Uiso 1 1 calc R . . C17 C 0.6593(6) 0.1223(5) 0.31254(11) 0.0496(9) Uani 1 1 d . . . H18 H 0.5559 0.0764 0.3287 0.06 Uiso 1 1 calc R . . C18 C 0.8081(6) -0.1849(4) 0.36770(9) 0.0439(8) Uani 1 1 d . . . C19 C 0.8145(7) -0.2866(5) 0.33568(11) 0.0592(11) Uani 1 1 d . . . H19 H 0.9339 -0.2793 0.3199 0.071 Uiso 1 1 calc R . . C20 C 0.6434(10) -0.3993(5) 0.32712(13) 0.0754(14) Uani 1 1 d . . . H20 H 0.648 -0.4657 0.3054 0.091 Uiso 1 1 calc R . . C21 C 0.4671(8) -0.4137(5) 0.35038(15) 0.0721(13) Uani 1 1 d . . . H21 H 0.3514 -0.4874 0.3442 0.086 Uiso 1 1 calc R . . C22 C 0.4635(7) -0.3176(5) 0.38298(13) 0.0601(11) Uani 1 1 d . . . H22 H 0.3465 -0.329 0.3991 0.072 Uiso 1 1 calc R . . C23 C 0.6328(6) -0.2046(4) 0.39166(10) 0.0475(9) Uani 1 1 d . . . H23 H 0.6294 -0.1412 0.4137 0.057 Uiso 1 1 calc R . . N9 N 0.7635(4) 0.2051(3) 0.39114(8) 0.0404(7) Uani 1 1 d . . . O1 O 0.3911(4) 0.1794(3) 0.42197(7) 0.0571(7) Uani 1 1 d D . . O2 O 1.0422(4) -0.0695(3) 0.41394(8) 0.0558(7) Uani 1 1 d . . . H1 H 0.502(5) 0.149(5) 0.4081(10) 0.067 Uiso 1 1 d D . . H2 H 1.147(7) -0.002(5) 0.4160(13) 0.067 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 C2 0.0416(19) 0.0431(16) 0.0403(19) 0.0003(15) -0.0019(17) 0.0033(16) C3 0.046(2) 0.058(2) 0.048(2) 0.0011(17) 0.0058(18) 0.0034(18) C4 0.065(3) 0.055(2) 0.048(2) -0.0031(17) 0.013(2) 0.013(2) C5 0.075(3) 0.0490(19) 0.044(2) -0.0080(16) 0.003(2) 0.004(2) C6 0.055(2) 0.0442(18) 0.048(2) -0.0082(16) -0.0013(19) -0.0047(18) C7 0.0425(19) 0.0385(15) 0.0336(18) 0.0007(13) -0.0034(16) 0.0031(15) C8 0.0398(19) 0.0453(17) 0.0389(19) -0.0002(15) -0.0001(16) -0.0045(15) C10 0.0352(19) 0.0538(18) 0.038(2) -0.0030(15) 0.0045(15) -0.0059(15) C11 0.039(2) 0.0611(19) 0.0306(18) -0.0040(15) 0.0004(16) 0.0053(18) C12 0.0419(19) 0.0413(16) 0.0374(19) -0.0044(14) 0.0037(16) 0.0007(15) C13 0.048(2) 0.062(2) 0.047(2) -0.0062(18) 0.0043(19) -0.0083(18) C14 0.067(3) 0.080(3) 0.0349(19) 0.0029(19) 0.013(2) -0.012(2) C15 0.073(3) 0.073(2) 0.0337(19) -0.0007(18) 0.000(2) 0.004(2) C16 0.053(2) 0.067(2) 0.052(3) -0.0056(19) -0.006(2) 0.001(2) C17 0.041(2) 0.0580(19) 0.050(2) -0.0016(16) 0.0000(19) -0.0057(17) C18 0.051(2) 0.0424(16) 0.0380(19) -0.0012(14) -0.0030(17) 0.0076(16) C19 0.076(3) 0.053(2) 0.049(2) -0.0069(17) -0.005(2) 0.014(2) C20 0.111(4) 0.051(2) 0.065(3) -0.013(2) -0.032(3) 0.014(3) C21 0.077(3) 0.047(2) 0.092(4) 0.000(2) -0.029(3) -0.002(2) C22 0.055(2) 0.046(2) 0.080(3) 0.008(2) -0.005(2) 0.0021(19) C23 0.051(2) 0.0442(17) 0.047(2) 0.0007(15) -0.0023(18) 0.0026(18) N9 0.0388(16) 0.0487(15) 0.0338(14) -0.0052(12) -0.0001(12) -0.0007(13) O1 0.0448(15) 0.0694(16) 0.0572(18) -0.0201(14) 0.0035(13) -0.0129(13) O2 0.0501(16) 0.0744(17) 0.0429(15) 0.0019(14) -0.0092(13) -0.0041(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 O1 1.352(4) . ? C2 C3 1.386(5) . ? C2 C7 1.408(5) . ? C3 C4 1.377(5) . ? C3 H3 0.93 . ? C4 C5 1.396(5) . ? C4 H4 0.93 . ? C5 C6 1.362(5) . ? C5 H5 0.93 . ? C6 C7 1.396(5) . ? C6 H6 0.93 . ? C7 C8 1.445(4) . ? C8 N9 1.276(4) . ? C8 H8 0.93 . ? C10 N9 1.457(4) . ? C10 C12 1.529(5) . ? C10 C11 1.551(5) . ? C10 H10 0.98 . ? C11 O2 1.424(4) . ? C11 C18 1.505(5) . ? C11 H11 0.98 . ? C12 C13 1.384(5) . ? C12 C17 1.388(5) . ? C13 C14 1.377(5) . ? C13 H13 0.93 . ? C14 C15 1.391(6) . ? C14 H14 0.93 . ? C15 C16 1.379(6) . ? C15 H15 0.93 . ? C16 C17 1.390(5) . ? C16 H16 0.93 . ? C17 H18 0.93 . ? C18 C19 1.388(5) . ? C18 C23 1.390(5) . ? C19 C20 1.387(6) . ? C19 H19 0.93 . ? C20 C21 1.375(7) . ? C20 H20 0.93 . ? C21 C22 1.382(6) . ? C21 H21 0.93 . ? C22 C23 1.381(5) . ? C22 H22 0.93 . ? C23 H23 0.93 . ? O1 H1 0.88(2) . ? O2 H2 0.83(4) . ? 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 O1 C2 C3 119.7(3) . . ? O1 C2 C7 120.7(3) . . ? C3 C2 C7 119.6(3) . . ? C4 C3 C2 120.3(4) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.6(4) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 119.2(4) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C7 121.7(4) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C6 C7 C2 118.6(3) . . ? C6 C7 C8 121.3(3) . . ? C2 C7 C8 120.0(3) . . ? N9 C8 C7 122.8(3) . . ? N9 C8 H8 118.6 . . ? C7 C8 H8 118.6 . . ? N9 C10 C12 111.6(3) . . ? N9 C10 C11 109.9(3) . . ? C12 C10 C11 113.1(3) . . ? N9 C10 H10 107.3 . . ? C12 C10 H10 107.3 . . ? C11 C10 H10 107.3 . . ? O2 C11 C18 107.9(3) . . ? O2 C11 C10 110.1(3) . . ? C18 C11 C10 114.1(3) . . ? O2 C11 H11 108.2 . . ? C18 C11 H11 108.2 . . ? C10 C11 H11 108.2 . . ? C13 C12 C17 118.5(4) . . ? C13 C12 C10 119.3(3) . . ? C17 C12 C10 122.2(3) . . ? C14 C13 C12 121.5(4) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 119.8(4) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 119.1(4) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C15 C16 C17 120.8(4) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C12 C17 C16 120.2(4) . . ? C12 C17 H18 119.9 . . ? C16 C17 H18 119.9 . . ? C19 C18 C23 118.7(4) . . ? C19 C18 C11 119.9(3) . . ? C23 C18 C11 121.3(3) . . ? C20 C19 C18 120.2(4) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 120.7(4) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 119.4(4) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C23 C22 C21 120.3(4) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C18 120.6(3) . . ? C22 C23 H23 119.7 . . ? C18 C23 H23 119.7 . . ? C8 N9 C10 119.5(3) . . ? C2 O1 H1 109(3) . . ? C11 O2 H2 103(3) . . ? 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 O1 C2 C3 C4 -179.3(3) . . . . ? C7 C2 C3 C4 1.3(5) . . . . ? C2 C3 C4 C5 -0.5(6) . . . . ? C3 C4 C5 C6 0.2(6) . . . . ? C4 C5 C6 C7 -0.7(6) . . . . ? C5 C6 C7 C2 1.4(5) . . . . ? C5 C6 C7 C8 -177.1(3) . . . . ? O1 C2 C7 C6 178.9(3) . . . . ? C3 C2 C7 C6 -1.7(5) . . . . ? O1 C2 C7 C8 -2.6(5) . . . . ? C3 C2 C7 C8 176.9(3) . . . . ? C6 C7 C8 N9 179.8(3) . . . . ? C2 C7 C8 N9 1.3(5) . . . . ? N9 C10 C11 O2 -53.2(4) . . . . ? C12 C10 C11 O2 -178.7(3) . . . . ? N9 C10 C11 C18 68.3(4) . . . . ? C12 C10 C11 C18 -57.2(4) . . . . ? N9 C10 C12 C13 134.0(3) . . . . ? C11 C10 C12 C13 -101.4(4) . . . . ? N9 C10 C12 C17 -45.4(4) . . . . ? C11 C10 C12 C17 79.2(4) . . . . ? C17 C12 C13 C14 0.6(5) . . . . ? C10 C12 C13 C14 -178.8(3) . . . . ? C12 C13 C14 C15 -0.7(6) . . . . ? C13 C14 C15 C16 -0.2(6) . . . . ? C14 C15 C16 C17 1.1(6) . . . . ? C13 C12 C17 C16 0.4(5) . . . . ? C10 C12 C17 C16 179.8(3) . . . . ? C15 C16 C17 C12 -1.3(6) . . . . ? O2 C11 C18 C19 -137.1(3) . . . . ? C10 C11 C18 C19 100.2(4) . . . . ? O2 C11 C18 C23 43.6(4) . . . . ? C10 C11 C18 C23 -79.2(4) . . . . ? C23 C18 C19 C20 3.0(5) . . . . ? C11 C18 C19 C20 -176.3(3) . . . . ? C18 C19 C20 C21 -0.9(6) . . . . ? C19 C20 C21 C22 -1.4(6) . . . . ? C20 C21 C22 C23 1.7(6) . . . . ? C21 C22 C23 C18 0.5(5) . . . . ? C19 C18 C23 C22 -2.8(5) . . . . ? C11 C18 C23 C22 176.6(3) . . . . ? C7 C8 N9 C10 -173.6(3) . . . . ? C12 C10 N9 C8 -120.9(3) . . . . ? C11 C10 N9 C8 112.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N9 0.88(2) 1.77(3) 2.553(4) 147(4) . O2 H2 O1 0.83(4) 2.04(4) 2.866(3) 176(4) 1_655 _chemical_name_common (1R,2S)-2-((2-hydroxy-1,2-diphenyl-ethylimino)-methyl)-phenol #===END #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_Compound6 _database_code_depnum_ccdc_archive 'CCDC 712154' #TrackingRef '- cifs 1-8_(R2).cif' _audit_creation_date 2010-07-21T21:55:50-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-[{(1S,2R)-1-hydroxy-1-phenylpropan-2-ylimino}methyl]-4-nitrophenol ; _chemical_formula_moiety 'C16 H16 N2 O4' _chemical_formula_sum 'C16 H16 N2 O4' _chemical_formula_weight 300.31 _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.1083(2) _cell_length_b 10.3445(4) _cell_length_c 12.3439(5) _cell_angle_alpha 93.254(2) _cell_angle_beta 100.417(2) _cell_angle_gamma 92.940(2) _cell_volume 764.38(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5803 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_special_details ; # Refinement with three restrains (explanation): These restrains are not geometrical, but least-squares restraints automatically applied by SHELXL-97 program for origin fixing of the unit cell. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.617435E-1 _diffrn_orient_matrix_ub_12 0.166736E-1 _diffrn_orient_matrix_ub_13 -0.783024E-1 _diffrn_orient_matrix_ub_21 -0.545443E-1 _diffrn_orient_matrix_ub_22 0.839541E-1 _diffrn_orient_matrix_ub_23 0.253895E-1 _diffrn_orient_matrix_ub_31 0.145015 _diffrn_orient_matrix_ub_32 0.456721E-1 _diffrn_orient_matrix_ub_33 -0.62939E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_unetI/netI 0.0773 _diffrn_reflns_number 7278 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _reflns_number_total 3435 _reflns_number_gt 2447 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1068P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.25(5) _refine_ls_number_reflns 3435 _refine_ls_number_parameters 391 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1787 _refine_ls_wR_factor_gt 0.1613 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 _refine_ls_abs_structure_details ; The light-atom structure prevented a useful absolute structure parameter. However, the chirality of the molecule is completely reliable by considering the enantiomeric purity of the starting material, (1S,2R)-norephedrine . The Friedel-pairs reflections were merged in the refinement by using MERG4. Flack H D (1983), Acta Cryst. A39, 876-881. ; _refine_ls_abs_structure_Flack -10(10) _refine_diff_density_max 0.254 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.055 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H9A H 0.703(4) 0.725(4) 0.454(3) 0.064(9) Uiso 1 1 d D . . H9B H 1.472(9) 1.489(5) 0.740(4) 0.066(14) Uiso 1 1 d . . . H2A H 0.884(11) 0.674(7) 0.707(6) 0.1 Uiso 1 1 d . . . H2B H 1.436(11) 1.491(6) 0.510(6) 0.09(2) Uiso 1 1 d . . . C2B C 1.6254(7) 1.6552(4) 0.8845(3) 0.0473(9) Uani 1 1 d . . . C3B C 1.7464(7) 1.7573(4) 0.9587(4) 0.0534(10) Uani 1 1 d . . . H3B H 1.8832 1.7905 0.946 0.064 Uiso 1 1 calc R . . C4B C 1.6656(7) 1.8064(4) 1.0469(3) 0.0489(9) Uani 1 1 d . . . H4B H 1.7477 1.8722 1.0937 0.059 Uiso 1 1 calc R . . C5B C 1.4587(6) 1.7586(4) 1.0679(3) 0.0439(9) Uani 1 1 d . . . C6B C 1.3351(6) 1.6618(4) 1.0004(3) 0.0427(9) Uani 1 1 d . . . H6B H 1.1989 1.6308 1.0154 0.051 Uiso 1 1 calc R . . C7B C 1.4136(6) 1.6093(4) 0.9086(3) 0.0425(9) Uani 1 1 d . . . C8B C 1.2800(7) 1.5089(4) 0.8384(3) 0.0461(9) Uani 1 1 d . . . H8B H 1.1448 1.4799 0.8558 0.055 Uiso 1 1 calc R . . C10B C 1.2225(8) 1.3529(4) 0.6751(3) 0.0530(10) Uani 1 1 d . . . H10B H 1.0713 1.3368 0.6896 0.064 Uiso 1 1 calc R . . C11B C 1.2116(7) 1.4017(4) 0.5592(3) 0.0471(9) Uani 1 1 d . . . H11B H 1.1215 1.4775 0.5521 0.057 Uiso 1 1 calc R . . C12B C 1.1118(4) 1.2980(3) 0.4698(2) 0.0484(9) Uani 1 1 d G . . C13B C 1.2504(4) 1.2177(3) 0.4232(3) 0.0724(14) Uani 1 1 d G . . H13B H 1.4041 1.2277 0.4468 0.087 Uiso 1 1 calc R . . C14B C 1.1592(5) 1.1223(3) 0.3412(3) 0.0833(17) Uani 1 1 d G . . H14B H 1.2519 1.0686 0.31 0.1 Uiso 1 1 calc R . . C15B C 0.9295(6) 1.1073(4) 0.3060(3) 0.0873(17) Uani 1 1 d G . . H15B H 0.8685 1.0435 0.2511 0.105 Uiso 1 1 calc R . . C16B C 0.7909(4) 1.1876(5) 0.3526(4) 0.098(2) Uani 1 1 d G . . H16B H 0.6372 1.1776 0.329 0.117 Uiso 1 1 calc R . . C17B C 0.8821(4) 1.2829(4) 0.4345(3) 0.0749(14) Uani 1 1 d G . . H17B H 0.7894 1.3367 0.4658 0.09 Uiso 1 1 calc R . . C18B C 1.3491(12) 1.2323(5) 0.6915(5) 0.0847(17) Uani 1 1 d . . . H18D H 1.3762 1.2157 0.7684 0.127 Uiso 1 1 calc R . . H18E H 1.4888 1.2443 0.667 0.127 Uiso 1 1 calc R . . H18F H 1.263 1.16 0.6496 0.127 Uiso 1 1 calc R . . N1B N 1.3772(6) 1.8134(3) 1.1619(3) 0.0544(9) Uani 1 1 d . . . N9B N 1.3406(6) 1.4576(3) 0.7520(3) 0.0485(8) Uani 1 1 d . . . O1B O 1.7017(5) 1.6082(3) 0.8028(3) 0.0637(9) Uani 1 1 d . . . O2B O 1.4354(5) 1.4400(3) 0.5536(3) 0.0609(8) Uani 1 1 d . . . O3B O 1.1932(6) 1.7747(3) 1.1777(3) 0.0693(9) Uani 1 1 d . . . O4B O 1.4968(6) 1.8934(4) 1.2262(4) 0.0957(14) Uani 1 1 d . . . C2A C 0.5348(6) 0.5592(4) 0.3168(3) 0.0445(9) Uani 1 1 d . . . C3A C 0.4055(7) 0.4582(4) 0.2459(4) 0.0537(10) Uani 1 1 d . . . H3A H 0.2676 0.4294 0.2603 0.064 Uiso 1 1 calc R . . C4A C 0.4794(7) 0.4040(4) 0.1586(4) 0.0539(10) Uani 1 1 d . . . H4A H 0.3919 0.3386 0.1135 0.065 Uiso 1 1 calc R . . C5A C 0.6860(7) 0.4449(4) 0.1352(3) 0.0460(9) Uani 1 1 d . . . C6A C 0.8225(6) 0.5396(4) 0.2017(3) 0.0449(9) Uani 1 1 d . . . H6A H 0.9612 0.5644 0.186 0.054 Uiso 1 1 calc R . . C7A C 0.7502(6) 0.5978(4) 0.2929(3) 0.0423(9) Uani 1 1 d . . . C8A C 0.8967(6) 0.6921(4) 0.3643(3) 0.0456(9) Uani 1 1 d . . . H8A H 1.039 0.7109 0.3501 0.055 Uiso 1 1 calc R . . C10A C 0.9648(7) 0.8448(4) 0.5323(3) 0.0458(9) Uani 1 1 d . . . H10A H 0.9169 0.9317 0.5163 0.055 Uiso 1 1 calc R . . C11A C 0.8985(6) 0.8104(3) 0.6417(3) 0.0417(8) Uani 1 1 d . . . H11A H 0.7352 0.8017 0.6299 0.05 Uiso 1 1 calc R . . C12A C 0.9772(4) 0.9144(2) 0.73415(19) 0.0450(9) Uani 1 1 d G . . C13A C 1.1817(4) 0.9106(3) 0.8045(2) 0.0555(10) Uani 1 1 d G . . H13A H 1.277 0.846 0.7929 0.067 Uiso 1 1 calc R . . C14A C 1.2437(5) 1.0033(3) 0.8922(2) 0.0707(14) Uani 1 1 d G . . H14A H 1.3805 1.0007 0.9393 0.085 Uiso 1 1 calc R . . C15A C 1.1013(6) 1.0998(3) 0.9096(2) 0.0859(17) Uani 1 1 d G . . H15A H 1.1428 1.1618 0.9683 0.103 Uiso 1 1 calc R . . C16A C 0.8969(6) 1.1037(3) 0.8393(3) 0.0895(18) Uani 1 1 d G . . H16A H 0.8016 1.1683 0.8509 0.107 Uiso 1 1 calc R . . C17A C 0.8348(4) 1.0110(3) 0.7515(3) 0.0691(14) Uani 1 1 d G . . H17A H 0.698 1.0136 0.7044 0.083 Uiso 1 1 calc R . . C18A C 1.2133(7) 0.8442(5) 0.5325(4) 0.0640(12) Uani 1 1 d . . . H18A H 1.2626 0.759 0.5459 0.096 Uiso 1 1 calc R . . H18B H 1.292 0.9053 0.5895 0.096 Uiso 1 1 calc R . . H18C H 1.2424 0.868 0.4622 0.096 Uiso 1 1 calc R . . N1A N 0.7605(6) 0.3873(4) 0.0390(3) 0.0586(10) Uani 1 1 d . . . N9A N 0.8366(6) 0.7510(3) 0.4468(3) 0.0482(8) Uani 1 1 d D . . O1A O 0.4618(5) 0.6144(3) 0.3983(2) 0.0566(8) Uani 1 1 d . . . O2A O 0.9780(5) 0.6878(3) 0.6657(3) 0.0544(7) Uani 1 1 d . . . O3A O 0.6301(6) 0.3114(4) -0.0234(3) 0.0909(13) Uani 1 1 d . . . O4A O 0.9473(6) 0.4176(4) 0.0223(3) 0.0755(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2B 0.050(2) 0.049(2) 0.044(2) 0.0046(17) 0.0104(17) -0.0028(17) C3B 0.043(2) 0.056(3) 0.059(3) -0.003(2) 0.0108(18) -0.0070(18) C4B 0.047(2) 0.046(2) 0.049(2) -0.0100(18) 0.0032(17) -0.0016(16) C5B 0.0412(19) 0.045(2) 0.045(2) -0.0008(17) 0.0081(16) 0.0033(15) C6B 0.0432(19) 0.045(2) 0.041(2) 0.0047(16) 0.0115(16) 0.0022(16) C7B 0.0422(19) 0.046(2) 0.040(2) 0.0026(16) 0.0084(16) 0.0020(16) C8B 0.051(2) 0.046(2) 0.043(2) 0.0037(17) 0.0128(16) -0.0030(16) C10B 0.068(3) 0.049(2) 0.041(2) -0.0086(17) 0.0155(18) -0.0141(19) C11B 0.051(2) 0.046(2) 0.046(2) -0.0032(17) 0.0160(17) 0.0031(17) C12B 0.055(2) 0.048(2) 0.042(2) -0.0057(17) 0.0101(17) 0.0019(17) C13B 0.052(2) 0.086(3) 0.078(3) -0.029(3) 0.025(2) -0.007(2) C14B 0.079(3) 0.076(3) 0.093(4) -0.043(3) 0.031(3) -0.008(3) C15B 0.087(4) 0.098(4) 0.067(3) -0.040(3) 0.008(3) -0.020(3) C16B 0.056(3) 0.128(5) 0.097(4) -0.043(4) 0.002(3) -0.005(3) C17B 0.057(3) 0.087(4) 0.076(3) -0.024(3) 0.007(2) 0.008(2) C18B 0.132(5) 0.047(2) 0.067(3) 0.004(2) -0.001(3) -0.004(3) N1B 0.052(2) 0.055(2) 0.056(2) -0.0094(17) 0.0131(17) 0.0004(16) N9B 0.0544(19) 0.0489(18) 0.0436(19) -0.0020(15) 0.0175(15) -0.0090(15) O1B 0.0671(18) 0.0684(19) 0.059(2) -0.0134(15) 0.0320(15) -0.0158(15) O2B 0.0636(18) 0.0651(19) 0.0534(18) -0.0034(15) 0.0169(14) -0.0151(14) O3B 0.0604(19) 0.085(2) 0.066(2) -0.0163(17) 0.0285(16) -0.0049(17) O4B 0.084(2) 0.100(3) 0.098(3) -0.064(2) 0.034(2) -0.029(2) C2A 0.0446(19) 0.050(2) 0.042(2) 0.0018(17) 0.0144(16) 0.0087(16) C3A 0.0438(19) 0.063(3) 0.057(3) 0.005(2) 0.0159(18) 0.0007(18) C4A 0.049(2) 0.056(2) 0.054(3) -0.0079(19) 0.0050(18) -0.0020(18) C5A 0.051(2) 0.051(2) 0.036(2) -0.0065(17) 0.0088(16) 0.0072(17) C6A 0.0416(19) 0.053(2) 0.041(2) -0.0035(17) 0.0116(16) 0.0045(17) C7A 0.049(2) 0.044(2) 0.0340(19) -0.0047(15) 0.0106(15) 0.0034(16) C8A 0.0451(19) 0.055(2) 0.038(2) -0.0036(17) 0.0135(16) 0.0027(17) C10A 0.057(2) 0.0388(19) 0.042(2) -0.0070(15) 0.0151(17) 0.0017(16) C11A 0.0427(19) 0.0402(19) 0.044(2) -0.0067(15) 0.0154(16) 0.0025(15) C12A 0.050(2) 0.0440(19) 0.043(2) -0.0019(15) 0.0140(16) 0.0041(15) C13A 0.056(2) 0.049(2) 0.058(3) 0.0060(19) 0.0036(19) 0.0032(18) C14A 0.079(3) 0.066(3) 0.056(3) 0.008(2) -0.011(2) -0.014(2) C15A 0.107(4) 0.077(3) 0.065(3) -0.031(3) 0.010(3) -0.011(3) C16A 0.081(3) 0.094(4) 0.089(4) -0.050(3) 0.021(3) 0.013(3) C17A 0.058(3) 0.074(3) 0.070(3) -0.034(2) 0.007(2) 0.019(2) C18A 0.062(3) 0.070(3) 0.061(3) -0.022(2) 0.029(2) -0.017(2) N1A 0.059(2) 0.064(2) 0.050(2) -0.0211(18) 0.0083(17) 0.0091(18) N9A 0.0501(18) 0.0536(19) 0.0421(18) -0.0070(15) 0.0160(14) -0.0030(15) O1A 0.0582(16) 0.0660(18) 0.0513(17) -0.0029(14) 0.0265(14) 0.0056(14) O2A 0.0641(17) 0.0424(14) 0.0628(18) 0.0000(12) 0.0288(14) 0.0048(12) O3A 0.078(2) 0.104(3) 0.081(3) -0.053(2) 0.011(2) -0.005(2) O4A 0.067(2) 0.094(3) 0.065(2) -0.0275(18) 0.0253(17) -0.0019(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2B O1B 1.268(5) . ? C2B C3B 1.437(6) . ? C2B C7B 1.443(5) . ? C3B C4B 1.358(6) . ? C3B H3B 0.93 . ? C4B C5B 1.407(5) . ? C4B H4B 0.93 . ? C5B C6B 1.366(5) . ? C5B N1B 1.442(5) . ? C6B C7B 1.401(5) . ? C6B H6B 0.93 . ? C7B C8B 1.432(5) . ? C8B N9B 1.286(5) . ? C8B H8B 0.93 . ? C10B N9B 1.466(5) . ? C10B C18B 1.505(7) . ? C10B C11B 1.536(6) . ? C10B H10B 0.98 . ? C11B O2B 1.418(5) . ? C11B C12B 1.515(4) . ? C11B H11B 0.98 . ? C12B C13B 1.39 . ? C12B C17B 1.39 . ? C13B C14B 1.39 . ? C13B H13B 0.93 . ? C14B C15B 1.39 . ? C14B H14B 0.93 . ? C15B C16B 1.39 . ? C15B H15B 0.93 . ? C16B C17B 1.39 . ? C16B H16B 0.93 . ? C17B H17B 0.93 . ? C18B H18D 0.96 . ? C18B H18E 0.96 . ? C18B H18F 0.96 . ? N1B O4B 1.226(5) . ? N1B O3B 1.226(5) . ? N9B H9B 0.89(6) . ? O2B H2B 0.78(7) . ? C2A O1A 1.289(5) . ? C2A C3A 1.430(6) . ? C2A C7A 1.441(5) . ? C3A C4A 1.346(6) . ? C3A H3A 0.93 . ? C4A C5A 1.395(6) . ? C4A H4A 0.93 . ? C5A C6A 1.380(5) . ? C5A N1A 1.454(5) . ? C6A C7A 1.398(5) . ? C6A H6A 0.93 . ? C7A C8A 1.434(5) . ? C8A N9A 1.277(5) . ? C8A H8A 0.93 . ? C10A N9A 1.475(5) . ? C10A C18A 1.517(6) . ? C10A C11A 1.533(5) . ? C10A H10A 0.98 . ? C11A O2A 1.409(5) . ? C11A C12A 1.517(4) . ? C11A H11A 0.98 . ? C12A C13A 1.39 . ? C12A C17A 1.39 . ? C13A C14A 1.39 . ? C13A H13A 0.93 . ? C14A C15A 1.39 . ? C14A H14A 0.93 . ? C15A C16A 1.39 . ? C15A H15A 0.93 . ? C16A C17A 1.39 . ? C16A H16A 0.93 . ? C17A H17A 0.93 . ? C18A H18A 0.96 . ? C18A H18B 0.96 . ? C18A H18C 0.96 . ? N1A O3A 1.220(5) . ? N1A O4A 1.224(5) . ? N9A H9A 0.866(19) . ? O2A H2A 0.85(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1B C2B C3B 121.7(4) . . ? O1B C2B C7B 122.1(4) . . ? C3B C2B C7B 116.2(4) . . ? C4B C3B C2B 121.6(4) . . ? C4B C3B H3B 119.2 . . ? C2B C3B H3B 119.2 . . ? C3B C4B C5B 120.5(4) . . ? C3B C4B H4B 119.7 . . ? C5B C4B H4B 119.7 . . ? C6B C5B C4B 120.8(3) . . ? C6B C5B N1B 120.0(3) . . ? C4B C5B N1B 119.1(3) . . ? C5B C6B C7B 120.0(3) . . ? C5B C6B H6B 120 . . ? C7B C6B H6B 120 . . ? C6B C7B C8B 119.0(3) . . ? C6B C7B C2B 120.8(3) . . ? C8B C7B C2B 120.1(3) . . ? N9B C8B C7B 122.3(4) . . ? N9B C8B H8B 118.9 . . ? C7B C8B H8B 118.9 . . ? N9B C10B C18B 108.6(4) . . ? N9B C10B C11B 105.9(3) . . ? C18B C10B C11B 112.9(4) . . ? N9B C10B H10B 109.8 . . ? C18B C10B H10B 109.8 . . ? C11B C10B H10B 109.8 . . ? O2B C11B C12B 112.1(3) . . ? O2B C11B C10B 104.9(3) . . ? C12B C11B C10B 111.7(3) . . ? O2B C11B H11B 109.3 . . ? C12B C11B H11B 109.3 . . ? C10B C11B H11B 109.3 . . ? C13B C12B C17B 120 . . ? C13B C12B C11B 119.9(2) . . ? C17B C12B C11B 120.1(2) . . ? C12B C13B C14B 120 . . ? C12B C13B H13B 120 . . ? C14B C13B H13B 120 . . ? C15B C14B C13B 120 . . ? C15B C14B H14B 120 . . ? C13B C14B H14B 120 . . ? C16B C15B C14B 120 . . ? C16B C15B H15B 120 . . ? C14B C15B H15B 120 . . ? C17B C16B C15B 120 . . ? C17B C16B H16B 120 . . ? C15B C16B H16B 120 . . ? C16B C17B C12B 120 . . ? C16B C17B H17B 120 . . ? C12B C17B H17B 120 . . ? C10B C18B H18D 109.5 . . ? C10B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C10B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? O4B N1B O3B 121.8(4) . . ? O4B N1B C5B 119.3(3) . . ? O3B N1B C5B 118.9(3) . . ? C8B N9B C10B 127.6(3) . . ? C8B N9B H9B 115(3) . . ? C10B N9B H9B 118(3) . . ? C11B O2B H2B 109(5) . . ? O1A C2A C3A 121.6(4) . . ? O1A C2A C7A 121.2(4) . . ? C3A C2A C7A 117.2(3) . . ? C4A C3A C2A 121.3(4) . . ? C4A C3A H3A 119.3 . . ? C2A C3A H3A 119.3 . . ? C3A C4A C5A 120.6(4) . . ? C3A C4A H4A 119.7 . . ? C5A C4A H4A 119.7 . . ? C6A C5A C4A 121.3(4) . . ? C6A C5A N1A 118.9(3) . . ? C4A C5A N1A 119.8(4) . . ? C5A C6A C7A 119.4(3) . . ? C5A C6A H6A 120.3 . . ? C7A C6A H6A 120.3 . . ? C6A C7A C8A 119.1(3) . . ? C6A C7A C2A 120.1(3) . . ? C8A C7A C2A 120.8(3) . . ? N9A C8A C7A 121.6(3) . . ? N9A C8A H8A 119.2 . . ? C7A C8A H8A 119.2 . . ? N9A C10A C18A 111.5(3) . . ? N9A C10A C11A 106.2(3) . . ? C18A C10A C11A 114.2(4) . . ? N9A C10A H10A 108.3 . . ? C18A C10A H10A 108.3 . . ? C11A C10A H10A 108.3 . . ? O2A C11A C12A 113.4(3) . . ? O2A C11A C10A 107.3(3) . . ? C12A C11A C10A 112.8(3) . . ? O2A C11A H11A 107.7 . . ? C12A C11A H11A 107.7 . . ? C10A C11A H11A 107.7 . . ? C13A C12A C17A 120 . . ? C13A C12A C11A 121.4(2) . . ? C17A C12A C11A 118.5(2) . . ? C12A C13A C14A 120 . . ? C12A C13A H13A 120 . . ? C14A C13A H13A 120 . . ? C15A C14A C13A 120 . . ? C15A C14A H14A 120 . . ? C13A C14A H14A 120 . . ? C14A C15A C16A 120 . . ? C14A C15A H15A 120 . . ? C16A C15A H15A 120 . . ? C17A C16A C15A 120 . . ? C17A C16A H16A 120 . . ? C15A C16A H16A 120 . . ? C16A C17A C12A 120 . . ? C16A C17A H17A 120 . . ? C12A C17A H17A 120 . . ? C10A C18A H18A 109.5 . . ? C10A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C10A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? O3A N1A O4A 122.5(4) . . ? O3A N1A C5A 117.8(4) . . ? O4A N1A C5A 119.7(3) . . ? C8A N9A C10A 129.8(3) . . ? C8A N9A H9A 112(3) . . ? C10A N9A H9A 118(3) . . ? C11A O2A H2A 92(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 O1B C2B C3B C4B -179.2(4) . . . . ? C7B C2B C3B C4B 0.5(6) . . . . ? C2B C3B C4B C5B -0.3(7) . . . . ? C3B C4B C5B C6B 0.1(7) . . . . ? C3B C4B C5B N1B -179.6(4) . . . . ? C4B C5B C6B C7B -0.3(6) . . . . ? N1B C5B C6B C7B 179.5(3) . . . . ? C5B C6B C7B C8B -179.3(3) . . . . ? C5B C6B C7B C2B 0.6(6) . . . . ? O1B C2B C7B C6B 179.0(4) . . . . ? C3B C2B C7B C6B -0.7(5) . . . . ? O1B C2B C7B C8B -1.1(6) . . . . ? C3B C2B C7B C8B 179.2(4) . . . . ? C6B C7B C8B N9B 179.1(4) . . . . ? C2B C7B C8B N9B -0.7(6) . . . . ? N9B C10B C11B O2B 53.0(4) . . . . ? C18B C10B C11B O2B -65.6(4) . . . . ? N9B C10B C11B C12B 174.7(3) . . . . ? C18B C10B C11B C12B 56.1(5) . . . . ? O2B C11B C12B C13B 24.4(4) . . . . ? C10B C11B C12B C13B -93.0(4) . . . . ? O2B C11B C12B C17B -155.6(3) . . . . ? C10B C11B C12B C17B 87.0(4) . . . . ? C17B C12B C13B C14B 0 . . . . ? C11B C12B C13B C14B 180.0(3) . . . . ? C12B C13B C14B C15B 0 . . . . ? C13B C14B C15B C16B 0 . . . . ? C14B C15B C16B C17B 0 . . . . ? C15B C16B C17B C12B 0 . . . . ? C13B C12B C17B C16B 0 . . . . ? C11B C12B C17B C16B -180.0(3) . . . . ? C6B C5B N1B O4B 174.8(4) . . . . ? C4B C5B N1B O4B -5.5(6) . . . . ? C6B C5B N1B O3B -2.4(6) . . . . ? C4B C5B N1B O3B 177.4(4) . . . . ? C7B C8B N9B C10B 178.5(4) . . . . ? C18B C10B N9B C8B -108.8(5) . . . . ? C11B C10B N9B C8B 129.7(4) . . . . ? O1A C2A C3A C4A 177.7(4) . . . . ? C7A C2A C3A C4A -1.8(6) . . . . ? C2A C3A C4A C5A 0.2(7) . . . . ? C3A C4A C5A C6A 1.5(7) . . . . ? C3A C4A C5A N1A -178.5(4) . . . . ? C4A C5A C6A C7A -1.5(6) . . . . ? N1A C5A C6A C7A 178.5(3) . . . . ? C5A C6A C7A C8A 177.4(4) . . . . ? C5A C6A C7A C2A -0.2(6) . . . . ? O1A C2A C7A C6A -177.8(3) . . . . ? C3A C2A C7A C6A 1.8(6) . . . . ? O1A C2A C7A C8A 4.7(6) . . . . ? C3A C2A C7A C8A -175.8(4) . . . . ? C6A C7A C8A N9A 177.9(4) . . . . ? C2A C7A C8A N9A -4.5(6) . . . . ? N9A C10A C11A O2A 66.6(4) . . . . ? C18A C10A C11A O2A -56.7(4) . . . . ? N9A C10A C11A C12A -167.8(3) . . . . ? C18A C10A C11A C12A 69.0(4) . . . . ? O2A C11A C12A C13A 30.5(4) . . . . ? C10A C11A C12A C13A -91.8(4) . . . . ? O2A C11A C12A C17A -145.9(2) . . . . ? C10A C11A C12A C17A 91.8(3) . . . . ? C17A C12A C13A C14A 0 . . . . ? C11A C12A C13A C14A -176.4(3) . . . . ? C12A C13A C14A C15A 0 . . . . ? C13A C14A C15A C16A 0 . . . . ? C14A C15A C16A C17A 0 . . . . ? C15A C16A C17A C12A 0 . . . . ? C13A C12A C17A C16A 0 . . . . ? C11A C12A C17A C16A 176.5(3) . . . . ? C6A C5A N1A O3A -174.3(4) . . . . ? C4A C5A N1A O3A 5.8(6) . . . . ? C6A C5A N1A O4A 4.4(6) . . . . ? C4A C5A N1A O4A -175.6(4) . . . . ? C7A C8A N9A C10A 176.3(4) . . . . ? C18A C10A N9A C8A -14.8(6) . . . . ? C11A C10A N9A C8A -139.7(4) . . . . ? _chemical_name_common ;2-(((1S,2R)-1-hydroxy-1-phenylpropan-2-ylimino)methyl)-4- nitrophenol ; #===END #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_Compound7 _database_code_depnum_ccdc_archive 'CCDC 712155' #TrackingRef '- cifs 1-8_(R2).cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 2-[{(1S,2R)-1-hydroxy-1-phenylpropan-2-ylimino}methyl]-4-bromophenol ; _chemical_formula_moiety 'C16 H16 Br1 N1 O2' _chemical_formula_sum 'C16 H16 Br1 N1 O2' _chemical_formula_weight 334.21 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 7.2044(2) _cell_length_b 9.3402(2) _cell_length_c 12.3377(3) _cell_angle_alpha 69.1986(10) _cell_angle_beta 80.3396(9) _cell_angle_gamma 75.9081(9) _cell_volume 749.70(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.48 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_special_details ; # Refinement with three restrains (explanation): These restrains are not geometrical, but least-squares restraints automatically applied by SHELXL-97 program for origin fixing of the unit cell. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.742 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7644 _exptl_absorpt_correction_T_max 0.8664 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.122644 _diffrn_orient_matrix_ub_12 -0.394316E-1 _diffrn_orient_matrix_ub_13 0.385623E-1 _diffrn_orient_matrix_ub_21 0.74785E-1 _diffrn_orient_matrix_ub_22 0.239428E-1 _diffrn_orient_matrix_ub_23 -0.780373E-1 _diffrn_orient_matrix_ub_31 -0.29015E-2 _diffrn_orient_matrix_ub_32 0.1074 _diffrn_orient_matrix_ub_33 0.3972E-3 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_unetI/netI 0.0609 _diffrn_reflns_number 12177 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _reflns_number_total 5691 _reflns_number_gt 4738 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0645P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5691 _refine_ls_number_parameters 379 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.108 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.028(9) _refine_diff_density_max 0.803 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.079 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2A C 0.7902(8) 0.0657(7) 0.7521(4) 0.0454(10) Uani 1 1 d . . . C3A C 0.8376(7) 0.1919(6) 0.6496(4) 0.0595(11) Uani 1 1 d . . . H3A H 0.8707 0.1736 0.5788 0.071 Uiso 1 1 calc R . . C4A C 0.8355(7) 0.3355(6) 0.6532(4) 0.0570(11) Uani 1 1 d . . . H4A H 0.8638 0.4143 0.5851 0.068 Uiso 1 1 calc R . . C5A C 0.7903(5) 0.3663(5) 0.7600(3) 0.0427(8) Uani 1 1 d . . . C6A C 0.7564(6) 0.2487(5) 0.8603(4) 0.0463(9) Uani 1 1 d . . . H6A H 0.7341 0.268 0.9308 0.056 Uiso 1 1 calc R . . C7A C 0.7546(5) 0.1010(5) 0.8592(3) 0.0452(8) Uani 1 1 d . . . C8A C 0.7117(7) -0.0169(5) 0.9647(4) 0.0452(10) Uani 1 1 d . . . H8A H 0.691 0.0062 1.0337 0.054 Uiso 1 1 calc R . . C10A C 0.6599(6) -0.2859(5) 1.0735(3) 0.0502(9) Uani 1 1 d . . . H10A H 0.5476 -0.3192 1.0623 0.06 Uiso 1 1 calc R . . C11A C 0.8381(6) -0.4206(4) 1.0773(3) 0.0429(8) Uani 1 1 d . . . H11A H 0.875 -0.4242 0.9981 0.051 Uiso 1 1 calc R . . C12A C 0.7948(7) -0.5788(5) 1.1545(3) 0.0478(9) Uani 1 1 d . . . C13A C 0.6454(8) -0.6322(6) 1.1316(4) 0.0639(12) Uani 1 1 d . . . H13A H 0.5668 -0.567 1.0734 0.077 Uiso 1 1 calc R . . C14A C 0.6124(10) -0.7811(7) 1.1945(6) 0.0822(17) Uani 1 1 d . . . H14A H 0.5121 -0.815 1.1784 0.099 Uiso 1 1 calc R . . C15A C 0.7274(12) -0.8778(7) 1.2798(5) 0.089(2) Uani 1 1 d . . . H15A H 0.7082 -0.9788 1.3204 0.107 Uiso 1 1 calc R . . C16A C 0.8724(12) -0.8254(7) 1.3057(5) 0.089(2) Uani 1 1 d . . . H16A H 0.9474 -0.8906 1.3658 0.107 Uiso 1 1 calc R . . C17A C 0.9083(9) -0.6758(6) 1.2432(4) 0.0635(14) Uani 1 1 d . . . H17A H 1.007 -0.6419 1.2609 0.076 Uiso 1 1 calc R . . C18A C 0.6191(8) -0.2457(6) 1.1851(4) 0.0667(13) Uani 1 1 d . . . H18A H 0.515 -0.1571 1.1768 0.1 Uiso 1 1 calc R . . H18B H 0.7317 -0.2214 1.2008 0.1 Uiso 1 1 calc R . . H18C H 0.5847 -0.3334 1.2484 0.1 Uiso 1 1 calc R . . N9A N 0.7002(5) -0.1535(4) 0.9690(3) 0.0502(8) Uani 1 1 d D . . O1A O 0.7880(5) -0.0700(4) 0.7498(2) 0.0551(7) Uani 1 1 d . . . O2A O 0.9939(4) -0.3903(4) 1.1155(3) 0.0539(7) Uani 1 1 d . . . H2A H 1.051(9) -0.333(7) 1.053(5) 0.065(15) Uiso 1 1 d . . . H2B H -0.060(9) 0.890(7) 0.615(5) 0.064(17) Uiso 1 1 d . . . C2B C 0.2211(7) 0.9070(7) 0.9314(4) 0.0463(11) Uani 1 1 d . . . C3B C 0.1722(7) 0.9534(6) 1.0341(4) 0.0575(11) Uani 1 1 d . . . H3B H 0.1327 0.8828 1.1039 0.069 Uiso 1 1 calc R . . C4B C 0.1829(7) 1.1001(6) 1.0305(4) 0.0578(11) Uani 1 1 d . . . H4B H 0.1506 1.1275 1.0978 0.069 Uiso 1 1 calc R . . C5B C 0.2424(5) 1.2092(5) 0.9256(3) 0.0437(8) Uani 1 1 d . . . C6B C 0.2814(6) 1.1721(6) 0.8252(4) 0.0512(10) Uani 1 1 d . . . H6B H 0.3156 1.246 0.7556 0.061 Uiso 1 1 calc R . . C7B C 0.2705(6) 1.0249(6) 0.8266(4) 0.0478(9) Uani 1 1 d . . . C8B C 0.3132(8) 0.9902(7) 0.7205(4) 0.0542(13) Uani 1 1 d . . . H8B H 0.3475 1.0668 0.6527 0.065 Uiso 1 1 calc R . . C10B C 0.3465(8) 0.8041(7) 0.6126(4) 0.0671(13) Uani 1 1 d . . . H10B H 0.4551 0.715 0.6263 0.081 Uiso 1 1 calc R . . C11B C 0.1702(6) 0.7488(5) 0.6022(3) 0.0489(9) Uani 1 1 d . . . H11B H 0.129 0.6829 0.6798 0.059 Uiso 1 1 calc R . . C12B C 0.2158(6) 0.6500(5) 0.5219(3) 0.0457(9) Uani 1 1 d . . . C13B C 0.1083(9) 0.6849(7) 0.4313(4) 0.0641(14) Uani 1 1 d . . . H13B H 0.0092 0.7725 0.416 0.077 Uiso 1 1 calc R . . C14B C 0.1464(10) 0.5895(8) 0.3611(5) 0.0767(15) Uani 1 1 d . . . H14B H 0.072 0.6137 0.2998 0.092 Uiso 1 1 calc R . . C15B C 0.2914(9) 0.4620(7) 0.3824(5) 0.0758(15) Uani 1 1 d . . . H15B H 0.3152 0.3983 0.3363 0.091 Uiso 1 1 calc R . . C16B C 0.4036(10) 0.4271(7) 0.4722(5) 0.0788(15) Uani 1 1 d . . . H16B H 0.5046 0.3409 0.4867 0.095 Uiso 1 1 calc R . . C17B C 0.3629(8) 0.5229(7) 0.5403(4) 0.0634(12) Uani 1 1 d . . . H17B H 0.4386 0.4997 0.6008 0.076 Uiso 1 1 calc R . . C18B C 0.3994(15) 0.9328(12) 0.5024(6) 0.130(4) Uani 1 1 d . . . H18D H 0.292 1.019 0.4856 0.194 Uiso 1 1 calc R . . H18E H 0.4321 0.8929 0.4384 0.194 Uiso 1 1 calc R . . H18F H 0.5073 0.9676 0.5138 0.194 Uiso 1 1 calc R . . N9B N 0.3061(6) 0.8571(5) 0.7153(3) 0.0597(10) Uani 1 1 d D . . O1B O 0.2168(5) 0.7690(4) 0.9340(3) 0.0623(8) Uani 1 1 d . . . O2B O 0.0161(6) 0.8761(4) 0.5636(3) 0.0613(8) Uani 1 1 d . . . Br1A Br 0.77849(6) 0.56987(4) 0.76271(4) 0.06716(17) Uani 1 1 d . . . Br1B Br 0.25992(5) 1.40900(4) 0.92558(4) 0.06669(17) Uani 1 1 d . . . H9A H 0.757(18) -0.186(15) 0.907(9) 0.18(5) Uiso 1 1 d D . . H9B H 0.283(18) 0.781(12) 0.784(8) 0.19(5) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2A 0.044(2) 0.048(2) 0.037(2) -0.0137(16) -0.0032(16) 0.0026(18) C3A 0.071(3) 0.055(3) 0.044(2) -0.0132(19) -0.0031(19) -0.005(2) C4A 0.064(3) 0.046(2) 0.048(2) -0.0040(18) 0.0030(18) -0.009(2) C5A 0.0299(16) 0.048(2) 0.0414(19) -0.0077(16) -0.0061(13) -0.0012(15) C6A 0.049(2) 0.043(2) 0.045(2) -0.0120(17) -0.0049(16) -0.0069(17) C7A 0.0386(18) 0.045(2) 0.046(2) -0.0118(17) -0.0033(15) -0.0023(16) C8A 0.043(2) 0.041(2) 0.047(2) -0.0140(18) -0.0027(17) -0.0020(18) C10A 0.059(2) 0.043(2) 0.042(2) -0.0060(16) -0.0006(16) -0.0114(18) C11A 0.0480(19) 0.0426(19) 0.0397(18) -0.0137(15) -0.0048(14) -0.0113(16) C12A 0.063(3) 0.045(2) 0.0360(18) -0.0149(16) -0.0001(17) -0.013(2) C13A 0.073(3) 0.061(3) 0.066(3) -0.028(2) 0.008(2) -0.026(2) C14A 0.097(4) 0.067(3) 0.092(4) -0.036(3) 0.026(3) -0.040(3) C15A 0.135(5) 0.053(3) 0.072(3) -0.016(3) 0.034(3) -0.039(3) C16A 0.142(6) 0.049(3) 0.057(3) -0.007(2) -0.001(3) -0.005(3) C17A 0.088(4) 0.049(3) 0.046(2) -0.008(2) -0.009(2) -0.009(3) C18A 0.080(3) 0.052(3) 0.054(3) -0.015(2) 0.011(2) -0.004(2) N9A 0.056(2) 0.0438(19) 0.0435(18) -0.0096(15) -0.0022(14) -0.0062(15) O1A 0.0639(18) 0.0540(18) 0.0421(15) -0.0159(12) -0.0023(12) -0.0035(14) O2A 0.0613(17) 0.0586(18) 0.0456(16) -0.0154(14) -0.0085(13) -0.0191(14) C2B 0.048(3) 0.059(3) 0.0373(19) -0.0156(18) -0.0068(17) -0.020(2) C3B 0.063(3) 0.069(3) 0.047(2) -0.020(2) 0.0010(18) -0.025(2) C4B 0.054(2) 0.074(3) 0.057(3) -0.039(2) -0.0036(19) -0.008(2) C5B 0.0271(16) 0.062(2) 0.043(2) -0.0212(18) -0.0069(13) -0.0028(16) C6B 0.048(2) 0.059(3) 0.051(2) -0.019(2) -0.0086(17) -0.0129(19) C7B 0.045(2) 0.058(2) 0.047(2) -0.0217(19) -0.0030(15) -0.0158(18) C8B 0.058(3) 0.072(4) 0.043(2) -0.025(2) 0.0021(19) -0.027(2) C10B 0.072(3) 0.093(4) 0.056(3) -0.045(3) 0.011(2) -0.034(3) C11B 0.058(2) 0.051(2) 0.0407(19) -0.0177(16) 0.0002(16) -0.0167(19) C12B 0.058(2) 0.049(2) 0.0338(17) -0.0147(15) -0.0018(15) -0.0183(19) C13B 0.082(4) 0.064(3) 0.051(2) -0.022(2) -0.020(2) -0.008(3) C14B 0.102(4) 0.082(4) 0.061(3) -0.037(3) -0.021(3) -0.017(3) C15B 0.099(4) 0.080(4) 0.072(3) -0.052(3) 0.012(3) -0.032(3) C16B 0.082(4) 0.070(3) 0.093(4) -0.047(3) -0.003(3) -0.004(3) C17B 0.069(3) 0.067(3) 0.060(3) -0.026(2) -0.013(2) -0.012(3) C18B 0.189(8) 0.192(9) 0.070(4) -0.077(5) 0.058(4) -0.146(8) N9B 0.067(2) 0.080(3) 0.051(2) -0.036(2) 0.0064(16) -0.035(2) O1B 0.083(2) 0.070(2) 0.0431(15) -0.0192(14) -0.0019(14) -0.0340(18) O2B 0.079(2) 0.0521(18) 0.0480(17) -0.0190(14) -0.0067(15) 0.0003(16) Br1A 0.0745(4) 0.0485(3) 0.0812(3) -0.0167(2) -0.0128(3) -0.0202(2) Br1B 0.0592(3) 0.0605(3) 0.0918(4) -0.0416(3) -0.0121(2) -0.0041(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2A O1A 1.282(7) . ? C2A C7A 1.441(6) . ? C2A C3A 1.449(8) . ? C3A C4A 1.355(7) . ? C3A H3A 0.93 . ? C4A C5A 1.417(6) . ? C4A H4A 0.93 . ? C5A C6A 1.364(6) . ? C5A Br1A 1.894(4) . ? C6A C7A 1.388(6) . ? C6A H6A 0.93 . ? C7A C8A 1.420(6) . ? C8A N9A 1.281(6) . ? C8A H8A 0.93 . ? C10A N9A 1.481(5) . ? C10A C18A 1.518(7) . ? C10A C11A 1.557(6) . ? C10A H10A 0.98 . ? C11A O2A 1.410(5) . ? C11A C12A 1.520(6) . ? C11A H11A 0.98 . ? C12A C17A 1.385(7) . ? C12A C13A 1.397(7) . ? C13A C14A 1.388(7) . ? C13A H13A 0.93 . ? C14A C15A 1.365(10) . ? C14A H14A 0.93 . ? C15A C16A 1.380(11) . ? C15A H15A 0.93 . ? C16A C17A 1.400(8) . ? C16A H16A 0.93 . ? C17A H17A 0.93 . ? C18A H18A 0.96 . ? C18A H18B 0.96 . ? C18A H18C 0.96 . ? N9A H9A 0.92(8) . ? O2A H2A 0.87(6) . ? C2B O1B 1.286(7) . ? C2B C7B 1.427(7) . ? C2B C3B 1.443(7) . ? C3B C4B 1.376(7) . ? C3B H3B 0.93 . ? C4B C5B 1.410(7) . ? C4B H4B 0.93 . ? C5B C6B 1.369(6) . ? C5B Br1B 1.900(5) . ? C6B C7B 1.390(7) . ? C6B H6B 0.93 . ? C7B C8B 1.425(6) . ? C8B N9B 1.281(7) . ? C8B H8B 0.93 . ? C10B N9B 1.479(6) . ? C10B C11B 1.522(6) . ? C10B C18B 1.526(9) . ? C10B H10B 0.98 . ? C11B O2B 1.416(6) . ? C11B C12B 1.528(6) . ? C11B H11B 0.98 . ? C12B C17B 1.364(7) . ? C12B C13B 1.364(6) . ? C13B C14B 1.404(8) . ? C13B H13B 0.93 . ? C14B C15B 1.357(9) . ? C14B H14B 0.93 . ? C15B C16B 1.379(9) . ? C15B H15B 0.93 . ? C16B C17B 1.385(7) . ? C16B H16B 0.93 . ? C17B H17B 0.93 . ? C18B H18D 0.96 . ? C18B H18E 0.96 . ? C18B H18F 0.96 . ? N9B H9B 0.92(8) . ? O2B H2B 0.79(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1A C2A C7A 121.8(5) . . ? O1A C2A C3A 123.1(4) . . ? C7A C2A C3A 115.0(5) . . ? C4A C3A C2A 122.3(4) . . ? C4A C3A H3A 118.9 . . ? C2A C3A H3A 118.9 . . ? C3A C4A C5A 120.3(4) . . ? C3A C4A H4A 119.8 . . ? C5A C4A H4A 119.8 . . ? C6A C5A C4A 119.6(4) . . ? C6A C5A Br1A 120.5(3) . . ? C4A C5A Br1A 119.8(3) . . ? C5A C6A C7A 121.3(4) . . ? C5A C6A H6A 119.3 . . ? C7A C6A H6A 119.3 . . ? C6A C7A C8A 119.8(4) . . ? C6A C7A C2A 121.2(4) . . ? C8A C7A C2A 119.0(4) . . ? N9A C8A C7A 122.8(4) . . ? N9A C8A H8A 118.6 . . ? C7A C8A H8A 118.6 . . ? N9A C10A C18A 113.5(4) . . ? N9A C10A C11A 105.7(3) . . ? C18A C10A C11A 112.2(4) . . ? N9A C10A H10A 108.4 . . ? C18A C10A H10A 108.4 . . ? C11A C10A H10A 108.4 . . ? O2A C11A C12A 110.3(3) . . ? O2A C11A C10A 110.1(3) . . ? C12A C11A C10A 112.1(3) . . ? O2A C11A H11A 108.1 . . ? C12A C11A H11A 108.1 . . ? C10A C11A H11A 108.1 . . ? C17A C12A C13A 118.9(5) . . ? C17A C12A C11A 121.3(4) . . ? C13A C12A C11A 119.7(4) . . ? C14A C13A C12A 121.0(5) . . ? C14A C13A H13A 119.5 . . ? C12A C13A H13A 119.5 . . ? C15A C14A C13A 119.9(6) . . ? C15A C14A H14A 120.1 . . ? C13A C14A H14A 120.1 . . ? C14A C15A C16A 119.9(5) . . ? C14A C15A H15A 120.1 . . ? C16A C15A H15A 120.1 . . ? C15A C16A C17A 121.1(6) . . ? C15A C16A H16A 119.5 . . ? C17A C16A H16A 119.5 . . ? C12A C17A C16A 119.2(6) . . ? C12A C17A H17A 120.4 . . ? C16A C17A H17A 120.4 . . ? C10A C18A H18A 109.5 . . ? C10A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C10A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C8A N9A C10A 127.6(4) . . ? C8A N9A H9A 118(9) . . ? C10A N9A H9A 112(9) . . ? C11A O2A H2A 105(4) . . ? O1B C2B C7B 122.2(4) . . ? O1B C2B C3B 122.0(4) . . ? C7B C2B C3B 115.8(5) . . ? C4B C3B C2B 121.2(4) . . ? C4B C3B H3B 119.4 . . ? C2B C3B H3B 119.4 . . ? C3B C4B C5B 120.4(4) . . ? C3B C4B H4B 119.8 . . ? C5B C4B H4B 119.8 . . ? C6B C5B C4B 120.0(4) . . ? C6B C5B Br1B 121.0(3) . . ? C4B C5B Br1B 119.0(3) . . ? C5B C6B C7B 120.5(4) . . ? C5B C6B H6B 119.8 . . ? C7B C6B H6B 119.8 . . ? C6B C7B C8B 118.9(4) . . ? C6B C7B C2B 121.9(4) . . ? C8B C7B C2B 119.2(5) . . ? N9B C8B C7B 122.3(5) . . ? N9B C8B H8B 118.9 . . ? C7B C8B H8B 118.9 . . ? N9B C10B C11B 107.6(3) . . ? N9B C10B C18B 111.6(5) . . ? C11B C10B C18B 112.1(5) . . ? N9B C10B H10B 108.5 . . ? C11B C10B H10B 108.5 . . ? C18B C10B H10B 108.5 . . ? O2B C11B C10B 111.4(4) . . ? O2B C11B C12B 110.3(3) . . ? C10B C11B C12B 111.6(3) . . ? O2B C11B H11B 107.8 . . ? C10B C11B H11B 107.8 . . ? C12B C11B H11B 107.8 . . ? C17B C12B C13B 118.4(4) . . ? C17B C12B C11B 120.8(4) . . ? C13B C12B C11B 120.8(4) . . ? C12B C13B C14B 120.4(5) . . ? C12B C13B H13B 119.8 . . ? C14B C13B H13B 119.8 . . ? C15B C14B C13B 120.2(5) . . ? C15B C14B H14B 119.9 . . ? C13B C14B H14B 119.9 . . ? C14B C15B C16B 120.0(5) . . ? C14B C15B H15B 120 . . ? C16B C15B H15B 120 . . ? C15B C16B C17B 118.7(5) . . ? C15B C16B H16B 120.7 . . ? C17B C16B H16B 120.7 . . ? C12B C17B C16B 122.3(5) . . ? C12B C17B H17B 118.8 . . ? C16B C17B H17B 118.8 . . ? C10B C18B H18D 109.5 . . ? C10B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C10B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C8B N9B C10B 128.4(4) . . ? C8B N9B H9B 117(8) . . ? C10B N9B H9B 114(8) . . ? C11B O2B H2B 113(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1A C2A C3A C4A 178.6(5) . . . . ? C7A C2A C3A C4A -4.4(7) . . . . ? C2A C3A C4A C5A 1.5(8) . . . . ? C3A C4A C5A C6A 2.6(7) . . . . ? C3A C4A C5A Br1A -177.6(4) . . . . ? C4A C5A C6A C7A -3.7(6) . . . . ? Br1A C5A C6A C7A 176.6(3) . . . . ? C5A C6A C7A C8A -177.6(4) . . . . ? C5A C6A C7A C2A 0.6(6) . . . . ? O1A C2A C7A C6A -179.6(4) . . . . ? C3A C2A C7A C6A 3.3(7) . . . . ? O1A C2A C7A C8A -1.4(7) . . . . ? C3A C2A C7A C8A -178.5(4) . . . . ? C6A C7A C8A N9A 177.2(4) . . . . ? C2A C7A C8A N9A -1.1(7) . . . . ? N9A C10A C11A O2A 75.3(4) . . . . ? C18A C10A C11A O2A -48.9(5) . . . . ? N9A C10A C11A C12A -161.6(3) . . . . ? C18A C10A C11A C12A 74.2(5) . . . . ? O2A C11A C12A C17A -3.8(6) . . . . ? C10A C11A C12A C17A -126.8(5) . . . . ? O2A C11A C12A C13A -179.8(4) . . . . ? C10A C11A C12A C13A 57.2(5) . . . . ? C17A C12A C13A C14A -1.4(7) . . . . ? C11A C12A C13A C14A 174.7(4) . . . . ? C12A C13A C14A C15A -0.2(8) . . . . ? C13A C14A C15A C16A 2.0(9) . . . . ? C14A C15A C16A C17A -2.2(9) . . . . ? C13A C12A C17A C16A 1.2(7) . . . . ? C11A C12A C17A C16A -174.8(4) . . . . ? C15A C16A C17A C12A 0.6(9) . . . . ? C7A C8A N9A C10A 178.9(4) . . . . ? C18A C10A N9A C8A 3.1(7) . . . . ? C11A C10A N9A C8A -120.2(5) . . . . ? O1B C2B C3B C4B 178.1(5) . . . . ? C7B C2B C3B C4B -3.2(7) . . . . ? C2B C3B C4B C5B 0.0(7) . . . . ? C3B C4B C5B C6B 3.0(6) . . . . ? C3B C4B C5B Br1B -178.8(3) . . . . ? C4B C5B C6B C7B -2.6(6) . . . . ? Br1B C5B C6B C7B 179.2(3) . . . . ? C5B C6B C7B C8B -179.6(4) . . . . ? C5B C6B C7B C2B -0.8(6) . . . . ? O1B C2B C7B C6B -177.7(4) . . . . ? C3B C2B C7B C6B 3.6(6) . . . . ? O1B C2B C7B C8B 1.1(7) . . . . ? C3B C2B C7B C8B -177.6(4) . . . . ? C6B C7B C8B N9B 180.0(5) . . . . ? C2B C7B C8B N9B 1.1(8) . . . . ? N9B C10B C11B O2B 72.4(5) . . . . ? C18B C10B C11B O2B -50.7(6) . . . . ? N9B C10B C11B C12B -163.8(4) . . . . ? C18B C10B C11B C12B 73.2(6) . . . . ? O2B C11B C12B C17B 178.3(4) . . . . ? C10B C11B C12B C17B 53.9(6) . . . . ? O2B C11B C12B C13B -2.9(6) . . . . ? C10B C11B C12B C13B -127.4(5) . . . . ? C17B C12B C13B C14B 1.5(8) . . . . ? C11B C12B C13B C14B -177.3(5) . . . . ? C12B C13B C14B C15B -0.4(9) . . . . ? C13B C14B C15B C16B -0.9(9) . . . . ? C14B C15B C16B C17B 1.0(9) . . . . ? C13B C12B C17B C16B -1.4(8) . . . . ? C11B C12B C17B C16B 177.4(5) . . . . ? C15B C16B C17B C12B 0.2(9) . . . . ? C7B C8B N9B C10B -179.9(5) . . . . ? C11B C10B N9B C8B -124.4(6) . . . . ? C18B C10B N9B C8B -1.0(9) . . . . ? _chemical_name_common ;2-(((1S,2R)-1-hydroxy-1-phenylpropan-2-ylimino)methyl)-4- bromophenol ;