#------------------------------------------------------------------------------ #$Date: 2014-07-11 21:33:45 +0300 (Fri, 11 Jul 2014) $ #$Revision: 120075 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/07/51/4075173.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4075173 loop_ _publ_author_name 'Pineda, Leslie W.' 'Jancik, Vojtech' 'Oswald, Rainer B.' 'Roesky, Herbert W.' _publ_section_title ; Preparation of LGe(Se)OH:  A Germanium Analogue of a Selenocarboxylic Acid (L = HC[(CMe)(NAr)]2, Ar = 2,6-iPr2C6H3) ; _journal_issue 9 _journal_name_full Organometallics _journal_page_first 2384 _journal_volume 25 _journal_year 2006 _chemical_formula_moiety 'C29 H42 Ge N2 O Se, C7 H8' _chemical_formula_sum 'C36 H50 Ge N2 O Se' _chemical_formula_weight 678.33 _chemical_name_systematic ; ? ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 115.82(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 25.974(4) _cell_length_b 16.195(3) _cell_length_c 18.151(3) _cell_measurement_reflns_used 5949 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 58.75 _cell_measurement_theta_min 3.73 _cell_volume 6873(3) _computing_cell_refinement 'Bruker AXS SAINT (v 7.01A, Bruker 2003)' _computing_data_collection 'Proteum (v 1.40, Bruker 2002)' _computing_data_reduction 'Bruker AXS SAINT (v 7.01A, Bruker 2003)' _computing_molecular_graphics 'Bruker AXS SHELXTL (v 6.12)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 5.602 _diffrn_measured_fraction_theta_full 0.969 _diffrn_measured_fraction_theta_max 0.969 _diffrn_measurement_device_type 'Bruker three circle diffractometer' _diffrn_measurement_method 'phi and omega scan' _diffrn_radiation_monochromator 'mirror system' _diffrn_radiation_source 'rotating anode' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 14278 _diffrn_reflns_theta_full 58.70 _diffrn_reflns_theta_max 58.70 _diffrn_reflns_theta_min 3.32 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.632 _exptl_absorpt_correction_T_max 0.8171 _exptl_absorpt_correction_T_min 0.6936 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour 'pale green' _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2832 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.391 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 388 _refine_ls_number_reflns 4734 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.0238 _refine_ls_R_factor_gt 0.0225 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+6.2439P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.0620 _reflns_number_gt 4501 _reflns_number_total 4734 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file om060088asi20060127_062631.cif _[local]_cod_data_source_block LGe(Se)OH.C7H8 _[local]_cod_cif_authors_sg_H-M C2/c _[local]_cod_cif_authors_sg_Hall '-C 2yc ' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 4075173 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 Ge1 Ge 0.233386(8) 0.887718(11) 0.063003(11) 0.01321(8) Uani 1 1 d . Se1 Se 0.275523(8) 0.891976(10) -0.019415(11) 0.01763(8) Uani 1 1 d . O1 O 0.21346(5) 0.79357(8) 0.09112(7) 0.0186(3) Uani 1 1 d . N1 N 0.16414(6) 0.95038(8) 0.02709(8) 0.0154(3) Uani 1 1 d . C1 C 0.08842(8) 1.02201(12) 0.04862(11) 0.0243(4) Uani 1 1 d . H1A H 0.0724 1.0285 -0.0109 0.037 Uiso 1 1 calc R H1B H 0.0909 1.0761 0.0741 0.037 Uiso 1 1 calc R H1C H 0.0637 0.9857 0.0623 0.037 Uiso 1 1 calc R N2 N 0.27010(6) 0.93828(8) 0.16852(8) 0.0149(3) Uani 1 1 d . C2 C 0.14693(7) 0.98496(10) 0.07969(10) 0.0175(4) Uani 1 1 d . C3 C 0.18189(7) 0.98960(10) 0.16377(10) 0.0177(4) Uani 1 1 d . H3A H 0.1650(8) 1.0145(12) 0.1945(12) 0.021 Uiso 1 1 d . C4 C 0.24026(7) 0.97372(10) 0.20450(10) 0.0161(4) Uani 1 1 d . C5 C 0.27107(8) 1.00019(11) 0.29265(10) 0.0207(4) Uani 1 1 d . H5A H 0.3019 1.0386 0.2989 0.031 Uiso 1 1 calc R H5B H 0.2873 0.9516 0.3272 0.031 Uiso 1 1 calc R H5C H 0.2441 1.0276 0.3091 0.031 Uiso 1 1 calc R C6 C 0.33178(7) 0.93055(10) 0.21267(10) 0.0163(4) Uani 1 1 d . C7 C 0.35562(8) 0.86414(11) 0.26695(10) 0.0190(4) Uani 1 1 d . C8 C 0.41511(8) 0.86036(12) 0.30852(11) 0.0236(4) Uani 1 1 d . H8A H 0.4325 0.8162 0.3455 0.028 Uiso 1 1 calc R C9 C 0.44917(8) 0.91924(12) 0.29705(11) 0.0259(4) Uani 1 1 d . H9A H 0.4896 0.9160 0.3268 0.031 Uiso 1 1 calc R C10 C 0.42458(8) 0.98330(12) 0.24212(11) 0.0234(4) Uani 1 1 d . H10A H 0.4485 1.0234 0.2345 0.028 Uiso 1 1 calc R C11 C 0.36565(7) 0.98983(11) 0.19806(10) 0.0187(4) Uani 1 1 d . C12 C 0.33935(8) 1.05977(11) 0.13674(10) 0.0198(4) Uani 1 1 d . H12A H 0.3016 1.0398 0.0945 0.024 Uiso 1 1 calc R C13 C 0.32799(10) 1.13646(12) 0.17599(12) 0.0315(5) Uani 1 1 d . H13A H 0.3016 1.1226 0.1996 0.047 Uiso 1 1 calc R H13B H 0.3110 1.1795 0.1344 0.047 Uiso 1 1 calc R H13C H 0.3641 1.1566 0.2192 0.047 Uiso 1 1 calc R C14 C 0.37576(9) 1.08166(13) 0.09233(12) 0.0288(4) Uani 1 1 d . H14A H 0.3843 1.0314 0.0697 0.043 Uiso 1 1 calc R H14B H 0.4116 1.1072 0.1310 0.043 Uiso 1 1 calc R H14C H 0.3548 1.1204 0.0478 0.043 Uiso 1 1 calc R C15 C 0.32002(8) 0.79678(11) 0.28066(11) 0.0221(4) Uani 1 1 d . H15A H 0.2788 0.8128 0.2512 0.026 Uiso 1 1 calc R C16 C 0.32807(9) 0.71427(12) 0.24566(12) 0.0284(4) Uani 1 1 d . H16A H 0.3188 0.7211 0.1876 0.043 Uiso 1 1 calc R H16B H 0.3027 0.6727 0.2515 0.043 Uiso 1 1 calc R H16C H 0.3679 0.6962 0.2755 0.043 Uiso 1 1 calc R C17 C 0.33470(9) 0.78555(13) 0.37185(11) 0.0317(5) Uani 1 1 d . H17A H 0.3312 0.8387 0.3951 0.048 Uiso 1 1 calc R H17B H 0.3740 0.7652 0.4011 0.048 Uiso 1 1 calc R H17C H 0.3083 0.7456 0.3775 0.048 Uiso 1 1 calc R C18 C 0.13197(7) 0.95946(10) -0.06105(10) 0.0161(4) Uani 1 1 d . C19 C 0.09693(8) 0.89468(10) -0.10673(11) 0.0184(4) Uani 1 1 d . C20 C 0.07181(8) 0.90215(11) -0.19199(11) 0.0222(4) Uani 1 1 d . H20A H 0.0486 0.8585 -0.2246 0.027 Uiso 1 1 calc R C21 C 0.07999(8) 0.97150(12) -0.22963(11) 0.0244(4) Uani 1 1 d . H21A H 0.0625 0.9753 -0.2877 0.029 Uiso 1 1 calc R C22 C 0.11351(8) 1.03531(11) -0.18332(11) 0.0227(4) Uani 1 1 d . H22A H 0.1183 1.0832 -0.2099 0.027 Uiso 1 1 calc R C23 C 0.14058(7) 1.03083(11) -0.09808(10) 0.0186(4) Uani 1 1 d . C24 C 0.17554(8) 1.10432(10) -0.04987(11) 0.0223(4) Uani 1 1 d . H24A H 0.1929 1.0897 0.0096 0.027 Uiso 1 1 calc R C25 C 0.13674(9) 1.17946(12) -0.06274(12) 0.0300(4) Uani 1 1 d . H25A H 0.1064 1.1655 -0.0466 0.045 Uiso 1 1 calc R H25B H 0.1196 1.1954 -0.1206 0.045 Uiso 1 1 calc R H25C H 0.1594 1.2255 -0.0293 0.045 Uiso 1 1 calc R C26 C 0.22411(8) 1.12571(12) -0.07278(12) 0.0264(4) Uani 1 1 d . H26A H 0.2487 1.0773 -0.0642 0.040 Uiso 1 1 calc R H26B H 0.2467 1.1713 -0.0384 0.040 Uiso 1 1 calc R H26C H 0.2080 1.1422 -0.1304 0.040 Uiso 1 1 calc R C27 C 0.08293(7) 0.82002(11) -0.06780(10) 0.0209(4) Uani 1 1 d . H27A H 0.1108 0.8188 -0.0087 0.025 Uiso 1 1 calc R C28 C 0.08815(9) 0.73874(12) -0.10614(12) 0.0317(4) Uani 1 1 d . H28A H 0.1266 0.7341 -0.1031 0.048 Uiso 1 1 calc R H28B H 0.0598 0.7371 -0.1635 0.048 Uiso 1 1 calc R H28C H 0.0814 0.6927 -0.0764 0.048 Uiso 1 1 calc R C29 C 0.02282(8) 0.82843(12) -0.07260(12) 0.0276(4) Uani 1 1 d . H29A H 0.0200 0.8806 -0.0474 0.041 Uiso 1 1 calc R H29B H 0.0155 0.7823 -0.0434 0.041 Uiso 1 1 calc R H29C H -0.0055 0.8277 -0.1300 0.041 Uiso 1 1 calc R C30 C 0.07711(9) 0.56207(13) 0.05024(13) 0.0327(5) Uani 1 1 d . H30A H 0.1116 0.5680 0.0414 0.049 Uiso 1 1 calc R H30B H 0.0440 0.5520 -0.0023 0.049 Uiso 1 1 calc R H30C H 0.0819 0.5155 0.0871 0.049 Uiso 1 1 calc R C31 C 0.06755(8) 0.64007(12) 0.08785(11) 0.0267(4) Uani 1 1 d . C32 C 0.10688(8) 0.70395(13) 0.11105(11) 0.0300(5) Uani 1 1 d . H32A H 0.1406 0.6984 0.1034 0.036 Uiso 1 1 calc R C33 C 0.09792(9) 0.77559(13) 0.14508(12) 0.0349(5) Uani 1 1 d . H33A H 0.1253 0.8188 0.1603 0.042 Uiso 1 1 calc R C34 C 0.04927(10) 0.78466(13) 0.15709(13) 0.0392(5) Uani 1 1 d . H34A H 0.0430 0.8339 0.1806 0.047 Uiso 1 1 calc R C35 C 0.00976(10) 0.72124(14) 0.13453(14) 0.0409(5) Uani 1 1 d . H35A H -0.0238 0.7268 0.1426 0.049 Uiso 1 1 calc R C36 C 0.01880(9) 0.64989(13) 0.10035(13) 0.0350(5) Uani 1 1 d . H36A H -0.0087 0.6068 0.0851 0.042 Uiso 1 1 calc R H1 H 0.2197(10) 0.7570(15) 0.0704(13) 0.028(6) 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 Ge1 0.01433(13) 0.01266(13) 0.01301(12) -0.00060(7) 0.00628(9) -0.00003(7) Se1 0.02281(13) 0.01540(12) 0.01937(12) -0.00135(7) 0.01355(9) -0.00069(7) O1 0.0237(7) 0.0136(6) 0.0223(6) -0.0013(5) 0.0135(6) -0.0008(5) N1 0.0164(7) 0.0153(7) 0.0141(7) -0.0001(6) 0.0064(6) 0.0003(6) C1 0.0198(9) 0.0315(10) 0.0219(9) -0.0021(8) 0.0093(8) 0.0046(8) N2 0.0152(7) 0.0150(7) 0.0143(7) 0.0000(6) 0.0062(6) 0.0000(6) C2 0.0186(9) 0.0144(8) 0.0217(9) 0.0004(7) 0.0108(8) -0.0017(7) C3 0.0215(10) 0.0181(9) 0.0174(9) -0.0018(7) 0.0121(8) 0.0013(7) C4 0.0208(9) 0.0125(8) 0.0164(8) 0.0005(7) 0.0095(7) -0.0014(7) C5 0.0223(9) 0.0223(9) 0.0174(9) -0.0016(7) 0.0086(8) 0.0023(7) C6 0.0150(9) 0.0191(9) 0.0139(8) -0.0039(7) 0.0056(7) 0.0020(7) C7 0.0230(10) 0.0194(9) 0.0152(8) -0.0022(7) 0.0089(7) 0.0025(8) C8 0.0231(10) 0.0256(10) 0.0189(9) 0.0018(8) 0.0062(8) 0.0076(8) C9 0.0164(9) 0.0329(11) 0.0243(9) -0.0023(8) 0.0052(8) 0.0019(8) C10 0.0189(10) 0.0258(10) 0.0257(9) -0.0039(8) 0.0100(8) -0.0036(8) C11 0.0217(10) 0.0178(9) 0.0174(8) -0.0037(7) 0.0093(8) -0.0002(7) C12 0.0200(9) 0.0180(9) 0.0205(9) -0.0006(7) 0.0080(7) -0.0031(7) C13 0.0468(13) 0.0218(10) 0.0311(10) 0.0027(8) 0.0218(10) 0.0049(9) C14 0.0317(11) 0.0281(10) 0.0314(10) 0.0029(9) 0.0182(9) -0.0013(9) C15 0.0227(10) 0.0219(9) 0.0205(9) 0.0053(7) 0.0084(8) 0.0029(8) C16 0.0327(11) 0.0207(10) 0.0302(10) 0.0034(8) 0.0120(9) 0.0020(8) C17 0.0371(12) 0.0354(11) 0.0245(10) 0.0099(8) 0.0151(9) 0.0060(9) C18 0.0137(8) 0.0196(9) 0.0144(8) 0.0010(7) 0.0058(7) 0.0042(7) C19 0.0143(9) 0.0221(10) 0.0182(9) -0.0004(7) 0.0064(8) 0.0025(7) C20 0.0185(9) 0.0267(10) 0.0189(9) -0.0023(7) 0.0059(8) -0.0017(8) C21 0.0228(10) 0.0332(11) 0.0144(9) 0.0026(8) 0.0054(8) 0.0008(8) C22 0.0241(10) 0.0233(10) 0.0215(9) 0.0054(8) 0.0105(8) 0.0021(8) C23 0.0183(9) 0.0188(9) 0.0198(9) 0.0005(7) 0.0095(7) 0.0033(7) C24 0.0287(11) 0.0180(9) 0.0193(9) 0.0024(7) 0.0097(8) -0.0009(7) C25 0.0403(12) 0.0222(10) 0.0325(10) -0.0002(8) 0.0206(10) 0.0019(9) C26 0.0288(11) 0.0206(9) 0.0296(10) -0.0002(8) 0.0125(9) -0.0023(8) C27 0.0188(9) 0.0230(10) 0.0165(8) 0.0018(7) 0.0036(7) -0.0034(7) C28 0.0387(12) 0.0238(10) 0.0327(10) 0.0011(9) 0.0155(9) -0.0004(9) C29 0.0237(10) 0.0316(11) 0.0268(10) 0.0048(8) 0.0104(8) -0.0032(8) C30 0.0291(11) 0.0359(11) 0.0359(11) 0.0031(9) 0.0168(9) -0.0001(9) C31 0.0238(10) 0.0310(10) 0.0237(9) 0.0072(8) 0.0089(8) -0.0010(9) C32 0.0248(11) 0.0381(12) 0.0242(10) 0.0100(9) 0.0081(8) -0.0058(9) C33 0.0367(12) 0.0330(11) 0.0252(10) 0.0064(8) 0.0043(9) -0.0127(9) C34 0.0451(14) 0.0289(11) 0.0380(12) -0.0012(9) 0.0129(10) -0.0015(10) C35 0.0309(12) 0.0371(12) 0.0578(14) -0.0053(10) 0.0222(11) -0.0012(10) C36 0.0257(11) 0.0308(11) 0.0493(12) -0.0023(10) 0.0171(10) -0.0072(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ge Ge -1.0885 0.8855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 Ge1 N2 99.33(6) O1 Ge1 N1 101.95(6) N2 Ge1 N1 95.66(6) O1 Ge1 Se1 121.36(5) N2 Ge1 Se1 119.18(4) N1 Ge1 Se1 114.98(4) H1 O1 Ge1 112.5(17) C2 N1 C18 122.09(14) C2 N1 Ge1 122.28(11) C18 N1 Ge1 115.63(10) C4 N2 C6 120.08(13) C4 N2 Ge1 121.96(12) C6 N2 Ge1 117.71(10) N1 C2 C3 122.73(16) N1 C2 C1 119.86(15) C3 C2 C1 117.41(15) C4 C3 C2 127.60(16) N2 C4 C3 123.21(15) N2 C4 C5 119.14(15) C3 C4 C5 117.63(15) C11 C6 C7 122.30(16) C11 C6 N2 117.96(15) C7 C6 N2 119.73(15) C8 C7 C6 117.29(16) C8 C7 C15 119.33(16) C6 C7 C15 123.37(16) C9 C8 C7 121.42(17) C8 C9 C10 120.11(17) C9 C10 C11 121.20(17) C10 C11 C6 117.63(16) C10 C11 C12 120.53(16) C6 C11 C12 121.85(15) C13 C12 C11 112.38(14) C13 C12 C14 110.37(15) C11 C12 C14 111.96(15) C7 C15 C16 110.83(14) C7 C15 C17 112.19(15) C16 C15 C17 109.16(15) C19 C18 C23 122.13(15) C19 C18 N1 119.32(15) C23 C18 N1 118.37(15) C20 C19 C18 117.40(16) C20 C19 C27 119.46(15) C18 C19 C27 123.06(15) C21 C20 C19 121.38(17) C22 C21 C20 120.14(16) C21 C22 C23 121.15(17) C22 C23 C18 117.76(16) C22 C23 C24 118.91(16) C18 C23 C24 123.27(15) C23 C24 C26 112.15(15) C23 C24 C25 110.22(16) C26 C24 C25 110.13(15) C19 C27 C28 112.81(14) C19 C27 C29 110.29(15) C28 C27 C29 110.03(15) C32 C31 C36 117.98(19) C32 C31 C30 121.26(18) C36 C31 C30 120.77(18) C33 C32 C31 121.21(19) C34 C33 C32 120.28(19) C33 C34 C35 119.1(2) C36 C35 C34 120.4(2) C35 C36 C31 121.01(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Ge1 O1 1.7559(12) Ge1 N2 1.9124(14) Ge1 N1 1.9153(14) Ge1 Se1 2.2061(5) O1 H1 0.76(2) N1 C2 1.340(2) N1 C18 1.454(2) C1 C2 1.497(3) N2 C4 1.341(2) N2 C6 1.451(2) C2 C3 1.397(3) C3 C4 1.391(3) C4 C5 1.506(2) C6 C11 1.403(3) C6 C7 1.407(3) C7 C8 1.395(3) C7 C15 1.519(3) C8 C9 1.377(3) C9 C10 1.387(3) C10 C11 1.388(3) C11 C12 1.525(2) C12 C13 1.523(3) C12 C14 1.528(3) C15 C16 1.533(3) C15 C17 1.539(3) C18 C19 1.400(3) C18 C23 1.403(2) C19 C20 1.398(3) C19 C27 1.522(2) C20 C21 1.378(3) C21 C22 1.377(3) C22 C23 1.395(3) C23 C24 1.521(3) C24 C26 1.530(3) C24 C25 1.532(3) C27 C28 1.522(3) C27 C29 1.531(3) C30 C31 1.507(3) C31 C32 1.384(3) C31 C36 1.389(3) C32 C33 1.381(3) C33 C34 1.380(3) C34 C35 1.382(3) C35 C36 1.379(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 Se1 0.76(2) 2.61(2) 3.3362(15) 163(2) 7_565 _journal_paper_doi 10.1021/om060088a