#------------------------------------------------------------------------------ #$Date: 2021-08-06 04:33:14 +0300 (Fri, 06 Aug 2021) $ #$Revision: 267968 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/79/7707962.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_7707962 loop_ _publ_author_name 'P\"uschmann, Sabrina D.' 'Fr\"uhwirt, Philipp' 'M\"uller, Stefanie M.' 'Wagner, Stefan H.' 'Torvisco, Ana' 'Fischer, Roland C.' 'Kelterer, Anne-Marie' 'Griesser, Thomas' 'Gescheidt, Georg' 'Haas, Michael' _publ_section_title ; Synthesis and characterization of diacylgermanes: persistent derivatives with superior photoreactivity ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D1DT02091A _journal_year 2021 _chemical_formula_moiety 'C34 H36 Ge O2' _chemical_formula_sum 'C34 H36 Ge O2' _chemical_formula_weight 549.22 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-04-20 deposited with the CCDC. 2021-08-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 107.229(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.7158(4) _cell_length_b 12.7206(4) _cell_length_c 18.0599(6) _cell_measurement_reflns_used 9887 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.91 _cell_measurement_theta_min 2.32 _cell_volume 2790.16(16) _computing_cell_refinement 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 924)' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'Bruker APEX2 area detector' _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'multilayer monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Incoatec microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.120 _diffrn_reflns_av_unetI/netI 0.0520 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 192347 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 33.228 _diffrn_reflns_theta_min 1.989 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\ms' _exptl_absorpt_coefficient_mu 1.127 _exptl_absorpt_correction_T_max 0.7465 _exptl_absorpt_correction_T_min 0.5126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.307 _exptl_crystal_description block _exptl_crystal_F_000 1152 _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.879 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.084 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 342 _refine_ls_number_reflns 10673 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0731 _refine_ls_R_factor_gt 0.0391 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+2.2587P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0873 _refine_ls_wR_factor_ref 0.1042 _reflns_Friedel_coverage 0.000 _reflns_number_gt 7458 _reflns_number_total 10673 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1dt02091a3.cif _cod_data_source_block AT1091_a _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7707962 _publcif_datablock.id {4b190722-57ca-4c0f-8349-6cd6b84f9285} _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.849 _shelx_estimated_absorpt_t_max 0.877 _shelx_res_file ; TITL AT1091_a.res in P2(1)/c AT1091_a.res created by SHELXL-2018/3 at 17:05:01 on 29-Sep-2020 REM Old TITL AT1091 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.079, Rweak 0.003, Alpha 0.026, Orientation as input REM Formula found by SHELXT: C34 Ge O2 CELL 0.71073 12.7158 12.7206 18.0599 90 107.229 90 ZERR 4 0.0004 0.0004 0.0006 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Ge O UNIT 136 144 4 8 L.S. 10 PLAN 5 SIZE 0.12 0.13 0.15 TEMP -173.13 CONF BOND $H LIST 6 HTAB fmap 2 acta 52 MORE -1 OMIT 4 0 4 OMIT 3 1 4 OMIT 3 0 0 OMIT 0 0 2 OMIT -2 0 8 OMIT -2 6 1 OMIT -4 3 5 WGHT 0.034900 2.258700 FVAR 0.36873 GE1 3 0.300147 0.252760 0.553612 11.00000 0.01341 0.01380 = 0.01316 0.00051 0.00442 0.00146 O1 4 0.325071 0.232789 0.715429 11.00000 0.02705 0.03432 = 0.01798 0.00085 0.00955 0.00910 O2 4 0.455345 0.230425 0.468937 11.00000 0.02341 0.02755 = 0.02160 -0.00226 0.00998 0.00202 C1 1 0.358105 0.196523 0.664162 11.00000 0.01790 0.01710 = 0.01654 0.00064 0.00531 -0.00081 C2 1 0.448543 0.261446 0.531243 11.00000 0.01654 0.01399 = 0.02059 0.00034 0.00577 0.00198 C3 1 0.226001 0.387951 0.557407 11.00000 0.01232 0.01590 = 0.01430 0.00014 0.00300 0.00081 C4 1 0.205089 0.157340 0.475478 11.00000 0.01247 0.01620 = 0.01605 0.00023 0.00384 0.00121 C5 1 0.451320 0.119698 0.679949 11.00000 0.01800 0.01772 = 0.01609 0.00173 0.00509 0.00020 C6 1 0.458667 0.053386 0.619513 11.00000 0.02022 0.01576 = 0.01778 0.00056 0.00541 -0.00057 AFIX 43 H6 2 0.404871 0.058619 0.570285 11.00000 -1.20000 AFIX 0 C7 1 0.542982 -0.019665 0.630275 11.00000 0.02485 0.01775 = 0.02129 -0.00054 0.00797 0.00332 AFIX 43 H7 2 0.545682 -0.065562 0.589381 11.00000 -1.20000 AFIX 0 C8 1 0.623231 -0.024734 0.701545 11.00000 0.02199 0.02358 = 0.02620 0.00468 0.00818 0.00758 AFIX 43 H8 2 0.681295 -0.074465 0.709741 11.00000 -1.20000 AFIX 0 C9 1 0.618744 0.042812 0.760892 11.00000 0.01992 0.02886 = 0.01914 0.00413 0.00234 0.00417 AFIX 43 H9 2 0.675960 0.040099 0.808642 11.00000 -1.20000 AFIX 0 C10 1 0.532788 0.114803 0.752796 11.00000 0.02241 0.02247 = 0.01540 0.00218 0.00396 0.00137 C11 1 0.531840 0.182331 0.820803 11.00000 0.03567 0.03711 = 0.01770 -0.00420 0.00007 0.01241 AFIX 137 H11A 2 0.516999 0.255424 0.803764 11.00000 -1.50000 H11B 2 0.603602 0.178015 0.860392 11.00000 -1.50000 H11C 2 0.474301 0.157621 0.842632 11.00000 -1.50000 AFIX 0 C12 1 0.548522 0.294542 0.594882 11.00000 0.01685 0.01593 = 0.02232 0.00191 0.00752 0.00123 C13 1 0.654514 0.254085 0.600308 11.00000 0.01802 0.01881 = 0.02969 0.00463 0.00940 0.00087 C14 1 0.741803 0.286867 0.663242 11.00000 0.01817 0.02813 = 0.04101 0.00446 0.00670 0.00379 AFIX 43 H14 2 0.813370 0.259864 0.668739 11.00000 -1.20000 AFIX 0 C15 1 0.727586 0.357459 0.717963 11.00000 0.02014 0.03178 = 0.03386 -0.00206 -0.00123 -0.00199 AFIX 43 H15 2 0.789135 0.378789 0.759575 11.00000 -1.20000 AFIX 0 C16 1 0.624055 0.396980 0.712200 11.00000 0.02602 0.02753 = 0.02939 -0.00732 0.00401 -0.00076 AFIX 43 H16 2 0.614046 0.445577 0.749483 11.00000 -1.20000 AFIX 0 C17 1 0.534921 0.364535 0.651064 11.00000 0.01853 0.02156 = 0.02504 -0.00177 0.00666 0.00155 AFIX 43 H17 2 0.463456 0.390382 0.647382 11.00000 -1.20000 AFIX 0 C18 1 0.675421 0.177394 0.542573 11.00000 0.02392 0.02548 = 0.04281 0.00188 0.01707 0.00729 AFIX 137 H18A 2 0.658815 0.211097 0.491609 11.00000 -1.50000 H18B 2 0.628208 0.115576 0.539095 11.00000 -1.50000 H18C 2 0.752828 0.155668 0.559493 11.00000 -1.50000 AFIX 0 C19 1 0.258604 0.483750 0.531500 11.00000 0.01313 0.01728 = 0.01515 0.00057 0.00290 0.00064 C20 1 0.204656 0.576696 0.540102 11.00000 0.01760 0.01425 = 0.01922 0.00074 0.00133 0.00076 AFIX 43 H20 2 0.226092 0.640486 0.521325 11.00000 -1.20000 AFIX 0 C21 1 0.121047 0.579389 0.574988 11.00000 0.01514 0.01941 = 0.01957 -0.00248 0.00016 0.00447 C22 1 0.086038 0.483748 0.596982 11.00000 0.01353 0.02271 = 0.02133 -0.00366 0.00543 0.00222 AFIX 43 H22 2 0.026740 0.483323 0.618919 11.00000 -1.20000 AFIX 0 C23 1 0.135090 0.388934 0.587856 11.00000 0.01285 0.01935 = 0.01675 -0.00085 0.00464 -0.00006 C24 1 0.350862 0.494923 0.495327 11.00000 0.02072 0.02021 = 0.02626 0.00306 0.01157 -0.00189 AFIX 137 H24A 2 0.325237 0.536234 0.447546 11.00000 -1.50000 H24B 2 0.373928 0.425101 0.483247 11.00000 -1.50000 H24C 2 0.413334 0.530689 0.531698 11.00000 -1.50000 AFIX 0 C25 1 0.070927 0.681556 0.589805 11.00000 0.02637 0.02243 = 0.03248 -0.00383 0.00563 0.00819 AFIX 137 H25A 2 0.096676 0.738760 0.563218 11.00000 -1.50000 H25B 2 0.092984 0.695628 0.645653 11.00000 -1.50000 H25C 2 -0.009496 0.676767 0.570188 11.00000 -1.50000 AFIX 0 C26 1 0.088181 0.289187 0.610439 11.00000 0.01919 0.02145 = 0.02432 0.00125 0.01067 -0.00150 AFIX 137 H26A 2 0.015572 0.303733 0.616633 11.00000 -1.50000 H26B 2 0.137472 0.262871 0.659477 11.00000 -1.50000 H26C 2 0.081031 0.236163 0.569876 11.00000 -1.50000 AFIX 0 C27 1 0.176394 0.188096 0.396688 11.00000 0.01408 0.01895 = 0.01696 -0.00007 0.00585 0.00168 C28 1 0.112097 0.121878 0.339319 11.00000 0.01817 0.02580 = 0.01536 -0.00131 0.00576 0.00133 AFIX 43 H28 2 0.094276 0.143224 0.286640 11.00000 -1.20000 AFIX 0 C29 1 0.073347 0.025718 0.356854 11.00000 0.01762 0.02265 = 0.02184 -0.00613 0.00634 -0.00137 C30 1 0.098498 -0.002073 0.434547 11.00000 0.01463 0.01776 = 0.02457 -0.00146 0.00663 -0.00038 AFIX 43 H30 2 0.070357 -0.066323 0.447677 11.00000 -1.20000 AFIX 0 C31 1 0.163599 0.060760 0.494220 11.00000 0.01310 0.01632 = 0.01854 0.00146 0.00581 0.00287 C32 1 0.185776 0.018167 0.575751 11.00000 0.01915 0.01964 = 0.02130 0.00340 0.00563 -0.00200 AFIX 137 H32A 2 0.123789 -0.025807 0.578555 11.00000 -1.50000 H32B 2 0.194620 0.076806 0.612283 11.00000 -1.50000 H32C 2 0.253266 -0.024049 0.589154 11.00000 -1.50000 AFIX 0 C33 1 0.007112 -0.045891 0.293602 11.00000 0.03242 0.02964 = 0.02568 -0.01009 0.00599 -0.00710 AFIX 137 H33A 2 -0.047895 -0.004510 0.255174 11.00000 -1.50000 H33B 2 -0.030097 -0.099099 0.316072 11.00000 -1.50000 H33C 2 0.056286 -0.080598 0.268454 11.00000 -1.50000 AFIX 0 C34 1 0.211516 0.291822 0.370882 11.00000 0.02202 0.02345 = 0.01769 0.00382 0.00572 -0.00082 AFIX 137 H34A 2 0.177395 0.300325 0.314959 11.00000 -1.50000 H34B 2 0.291828 0.293097 0.382459 11.00000 -1.50000 H34C 2 0.188116 0.349351 0.398483 11.00000 -1.50000 AFIX 0 HKLF 4 REM AT1091_a.res in P2(1)/c REM wR2 = 0.104153, GooF = S = 1.03013, Restrained GooF = 1.03013 for all data REM R1 = 0.039068 for 7458 Fo > 4sig(Fo) and 0.073131 for all 10673 data REM 342 parameters refined using 0 restraints END WGHT 0.0349 2.2587 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.879, deepest hole -0.575, 1-sigma level 0.084 Q1 1 0.2694 0.2479 0.5780 11.00000 0.05 0.88 Q2 1 0.4044 0.2490 0.5521 11.00000 0.05 0.84 Q3 1 0.2621 0.1933 0.5287 11.00000 0.05 0.78 Q4 1 0.4984 0.1906 0.6191 11.00000 0.05 0.62 Q5 1 0.2703 0.3119 0.5329 11.00000 0.05 0.60 ; _shelx_res_checksum 26458 _publcif_funding_html ; ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ge1 Ge 0.30015(2) 0.25276(2) 0.55361(2) 0.01335(5) Uani 1 1 d . . . . . O1 O 0.32507(12) 0.23279(11) 0.71543(8) 0.0258(3) Uani 1 1 d . . . . . O2 O 0.45535(11) 0.23042(10) 0.46894(8) 0.0235(3) Uani 1 1 d . . . . . C1 C 0.35810(14) 0.19652(13) 0.66416(10) 0.0171(3) Uani 1 1 d . . . . . C2 C 0.44854(14) 0.26145(12) 0.53124(10) 0.0170(3) Uani 1 1 d . . . . . C3 C 0.22600(13) 0.38795(12) 0.55741(9) 0.0144(3) Uani 1 1 d . . . . . C4 C 0.20509(13) 0.15734(12) 0.47548(10) 0.0150(3) Uani 1 1 d . . . . . C5 C 0.45132(14) 0.11970(13) 0.67995(10) 0.0173(3) Uani 1 1 d . . . . . C6 C 0.45867(14) 0.05339(13) 0.61951(10) 0.0180(3) Uani 1 1 d . . . . . H6 H 0.404871 0.058619 0.570285 0.022 Uiso 1 1 calc R U . . . C7 C 0.54298(15) -0.01967(14) 0.63027(11) 0.0210(3) Uani 1 1 d . . . . . H7 H 0.545682 -0.065562 0.589381 0.025 Uiso 1 1 calc R U . . . C8 C 0.62323(15) -0.02473(15) 0.70154(11) 0.0237(4) Uani 1 1 d . . . . . H8 H 0.681295 -0.074465 0.709741 0.028 Uiso 1 1 calc R U . . . C9 C 0.61874(15) 0.04281(15) 0.76089(11) 0.0234(4) Uani 1 1 d . . . . . H9 H 0.675960 0.040099 0.808642 0.028 Uiso 1 1 calc R U . . . C10 C 0.53279(15) 0.11480(14) 0.75280(10) 0.0204(3) Uani 1 1 d . . . . . C11 C 0.53184(18) 0.18233(18) 0.82080(11) 0.0319(4) Uani 1 1 d . . . . . H11A H 0.516999 0.255424 0.803764 0.048 Uiso 1 1 calc R U . . . H11B H 0.603602 0.178015 0.860392 0.048 Uiso 1 1 calc R U . . . H11C H 0.474301 0.157621 0.842632 0.048 Uiso 1 1 calc R U . . . C12 C 0.54852(14) 0.29454(13) 0.59488(10) 0.0180(3) Uani 1 1 d . . . . . C13 C 0.65451(14) 0.25409(14) 0.60031(11) 0.0217(3) Uani 1 1 d . . . . . C14 C 0.74180(16) 0.28687(17) 0.66324(13) 0.0295(4) Uani 1 1 d . . . . . H14 H 0.813370 0.259864 0.668739 0.035 Uiso 1 1 calc R U . . . C15 C 0.72759(16) 0.35746(17) 0.71796(13) 0.0306(4) Uani 1 1 d . . . . . H15 H 0.789135 0.378789 0.759575 0.037 Uiso 1 1 calc R U . . . C16 C 0.62406(16) 0.39698(16) 0.71220(12) 0.0286(4) Uani 1 1 d . . . . . H16 H 0.614046 0.445577 0.749483 0.034 Uiso 1 1 calc R U . . . C17 C 0.53492(15) 0.36453(14) 0.65106(11) 0.0217(3) Uani 1 1 d . . . . . H17 H 0.463456 0.390382 0.647382 0.026 Uiso 1 1 calc R U . . . C18 C 0.67542(16) 0.17739(16) 0.54257(13) 0.0292(4) Uani 1 1 d . . . . . H18A H 0.658815 0.211097 0.491609 0.044 Uiso 1 1 calc R U . . . H18B H 0.628208 0.115576 0.539095 0.044 Uiso 1 1 calc R U . . . H18C H 0.752828 0.155668 0.559493 0.044 Uiso 1 1 calc R U . . . C19 C 0.25860(13) 0.48375(13) 0.53150(10) 0.0155(3) Uani 1 1 d . . . . . C20 C 0.20466(14) 0.57670(13) 0.54010(10) 0.0179(3) Uani 1 1 d . . . . . H20 H 0.226092 0.640486 0.521325 0.021 Uiso 1 1 calc R U . . . C21 C 0.12105(14) 0.57939(14) 0.57499(10) 0.0191(3) Uani 1 1 d . . . . . C22 C 0.08604(13) 0.48375(14) 0.59698(10) 0.0191(3) Uani 1 1 d . . . . . H22 H 0.026740 0.483323 0.618919 0.023 Uiso 1 1 calc R U . . . C23 C 0.13509(13) 0.38893(13) 0.58786(10) 0.0163(3) Uani 1 1 d . . . . . C24 C 0.35086(15) 0.49492(14) 0.49533(11) 0.0214(3) Uani 1 1 d . . . . . H24A H 0.325237 0.536234 0.447546 0.032 Uiso 1 1 calc R U . . . H24B H 0.373928 0.425101 0.483247 0.032 Uiso 1 1 calc R U . . . H24C H 0.413334 0.530689 0.531698 0.032 Uiso 1 1 calc R U . . . C25 C 0.07093(16) 0.68156(15) 0.58981(12) 0.0278(4) Uani 1 1 d . . . . . H25A H 0.096676 0.738760 0.563218 0.042 Uiso 1 1 calc R U . . . H25B H 0.092984 0.695628 0.645653 0.042 Uiso 1 1 calc R U . . . H25C H -0.009496 0.676767 0.570188 0.042 Uiso 1 1 calc R U . . . C26 C 0.08818(15) 0.28919(14) 0.61044(11) 0.0207(3) Uani 1 1 d . . . . . H26A H 0.015572 0.303733 0.616633 0.031 Uiso 1 1 calc R U . . . H26B H 0.137472 0.262871 0.659477 0.031 Uiso 1 1 calc R U . . . H26C H 0.081031 0.236163 0.569876 0.031 Uiso 1 1 calc R U . . . C27 C 0.17639(13) 0.18810(13) 0.39669(10) 0.0164(3) Uani 1 1 d . . . . . C28 C 0.11210(14) 0.12188(14) 0.33932(10) 0.0196(3) Uani 1 1 d . . . . . H28 H 0.094276 0.143224 0.286640 0.024 Uiso 1 1 calc R U . . . C29 C 0.07335(14) 0.02572(14) 0.35685(11) 0.0206(3) Uani 1 1 d . . . . . C30 C 0.09850(13) -0.00207(13) 0.43455(11) 0.0188(3) Uani 1 1 d . . . . . H30 H 0.070357 -0.066323 0.447677 0.023 Uiso 1 1 calc R U . . . C31 C 0.16360(13) 0.06076(13) 0.49422(10) 0.0157(3) Uani 1 1 d . . . . . C32 C 0.18578(14) 0.01817(14) 0.57575(10) 0.0201(3) Uani 1 1 d . . . . . H32A H 0.123789 -0.025807 0.578555 0.030 Uiso 1 1 calc R U . . . H32B H 0.194620 0.076806 0.612283 0.030 Uiso 1 1 calc R U . . . H32C H 0.253266 -0.024049 0.589154 0.030 Uiso 1 1 calc R U . . . C33 C 0.00711(18) -0.04589(16) 0.29360(12) 0.0298(4) Uani 1 1 d . . . . . H33A H -0.047895 -0.004510 0.255174 0.045 Uiso 1 1 calc R U . . . H33B H -0.030097 -0.099099 0.316072 0.045 Uiso 1 1 calc R U . . . H33C H 0.056286 -0.080598 0.268454 0.045 Uiso 1 1 calc R U . . . C34 C 0.21152(15) 0.29182(15) 0.37088(10) 0.0211(3) Uani 1 1 d . . . . . H34A H 0.177395 0.300325 0.314959 0.032 Uiso 1 1 calc R U . . . H34B H 0.291828 0.293097 0.382459 0.032 Uiso 1 1 calc R U . . . H34C H 0.188116 0.349351 0.398483 0.032 Uiso 1 1 calc R U . . . 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 0.01341(7) 0.01380(7) 0.01316(8) 0.00051(6) 0.00442(5) 0.00146(6) O1 0.0271(7) 0.0343(8) 0.0180(6) 0.0008(5) 0.0096(5) 0.0091(5) O2 0.0234(6) 0.0275(7) 0.0216(6) -0.0023(5) 0.0100(5) 0.0020(5) C1 0.0179(7) 0.0171(7) 0.0165(8) 0.0006(6) 0.0053(6) -0.0008(6) C2 0.0165(7) 0.0140(7) 0.0206(8) 0.0003(6) 0.0058(6) 0.0020(5) C3 0.0123(6) 0.0159(7) 0.0143(7) 0.0001(5) 0.0030(5) 0.0008(5) C4 0.0125(6) 0.0162(7) 0.0161(7) 0.0002(6) 0.0038(5) 0.0012(5) C5 0.0180(7) 0.0177(7) 0.0161(8) 0.0017(6) 0.0051(6) 0.0002(6) C6 0.0202(8) 0.0158(7) 0.0178(8) 0.0006(6) 0.0054(6) -0.0006(6) C7 0.0248(8) 0.0177(7) 0.0213(9) -0.0005(6) 0.0080(7) 0.0033(6) C8 0.0220(8) 0.0236(8) 0.0262(9) 0.0047(7) 0.0082(7) 0.0076(7) C9 0.0199(8) 0.0289(9) 0.0191(8) 0.0041(7) 0.0023(6) 0.0042(7) C10 0.0224(8) 0.0225(8) 0.0154(8) 0.0022(6) 0.0040(6) 0.0014(6) C11 0.0357(11) 0.0371(11) 0.0177(9) -0.0042(8) 0.0001(8) 0.0124(9) C12 0.0168(7) 0.0159(7) 0.0223(8) 0.0019(6) 0.0075(6) 0.0012(6) C13 0.0180(7) 0.0188(7) 0.0297(9) 0.0046(7) 0.0094(7) 0.0009(6) C14 0.0182(8) 0.0281(9) 0.0410(12) 0.0045(9) 0.0067(8) 0.0038(7) C15 0.0201(8) 0.0318(10) 0.0339(11) -0.0021(8) -0.0012(8) -0.0020(8) C16 0.0260(9) 0.0275(9) 0.0294(10) -0.0073(8) 0.0040(8) -0.0008(7) C17 0.0185(8) 0.0216(8) 0.0250(9) -0.0018(7) 0.0067(7) 0.0016(6) C18 0.0239(9) 0.0255(9) 0.0428(12) 0.0019(8) 0.0171(9) 0.0073(7) C19 0.0131(7) 0.0173(7) 0.0152(7) 0.0006(6) 0.0029(6) 0.0006(5) C20 0.0176(7) 0.0142(7) 0.0192(8) 0.0007(6) 0.0013(6) 0.0008(6) C21 0.0151(7) 0.0194(7) 0.0196(8) -0.0025(6) 0.0002(6) 0.0045(6) C22 0.0135(7) 0.0227(8) 0.0213(8) -0.0037(6) 0.0054(6) 0.0022(6) C23 0.0129(7) 0.0194(7) 0.0167(7) -0.0009(6) 0.0046(6) -0.0001(6) C24 0.0207(8) 0.0202(8) 0.0263(9) 0.0031(7) 0.0116(7) -0.0019(6) C25 0.0264(9) 0.0224(9) 0.0325(11) -0.0038(8) 0.0056(8) 0.0082(7) C26 0.0192(8) 0.0215(8) 0.0243(9) 0.0013(7) 0.0107(7) -0.0015(6) C27 0.0141(7) 0.0189(7) 0.0170(8) -0.0001(6) 0.0059(6) 0.0017(6) C28 0.0182(7) 0.0258(8) 0.0154(8) -0.0013(6) 0.0058(6) 0.0013(6) C29 0.0176(7) 0.0227(8) 0.0218(8) -0.0061(7) 0.0063(6) -0.0014(6) C30 0.0146(7) 0.0178(7) 0.0246(9) -0.0015(6) 0.0066(6) -0.0004(6) C31 0.0131(7) 0.0163(7) 0.0185(8) 0.0015(6) 0.0058(6) 0.0029(5) C32 0.0192(8) 0.0196(8) 0.0213(8) 0.0034(6) 0.0056(6) -0.0020(6) C33 0.0324(10) 0.0296(10) 0.0257(10) -0.0101(8) 0.0060(8) -0.0071(8) C34 0.0220(8) 0.0234(8) 0.0177(8) 0.0038(7) 0.0057(6) -0.0008(7) 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' Ge Ge 0.1547 1.8001 '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' 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 C3 Ge1 C4 111.25(6) . . ? C3 Ge1 C1 108.02(7) . . ? C4 Ge1 C1 116.73(7) . . ? C3 Ge1 C2 115.98(6) . . ? C4 Ge1 C2 107.25(7) . . ? C1 Ge1 C2 97.19(7) . . ? O1 C1 C5 122.38(16) . . ? O1 C1 Ge1 120.39(13) . . ? C5 C1 Ge1 116.81(11) . . ? O2 C2 C12 121.49(15) . . ? O2 C2 Ge1 119.10(13) . . ? C12 C2 Ge1 119.07(12) . . ? C19 C3 C23 118.28(14) . . ? C19 C3 Ge1 123.45(11) . . ? C23 C3 Ge1 118.27(12) . . ? C27 C4 C31 118.45(15) . . ? C27 C4 Ge1 117.94(12) . . ? C31 C4 Ge1 123.61(12) . . ? C6 C5 C10 119.83(15) . . ? C6 C5 C1 118.38(15) . . ? C10 C5 C1 121.76(15) . . ? C7 C6 C5 121.31(16) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C8 C7 C6 119.10(17) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 120.04(16) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C10 122.25(17) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C9 C10 C5 117.39(16) . . ? C9 C10 C11 118.94(16) . . ? C5 C10 C11 123.67(16) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 119.99(17) . . ? C17 C12 C2 118.41(15) . . ? C13 C12 C2 121.57(16) . . ? C14 C13 C12 117.24(17) . . ? C14 C13 C18 119.71(17) . . ? C12 C13 C18 123.05(17) . . ? C15 C14 C13 122.25(18) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? C16 C15 C14 120.24(19) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 119.04(19) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C16 C17 C12 121.21(17) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C3 119.43(14) . . ? C20 C19 C24 115.99(15) . . ? C3 C19 C24 124.57(14) . . ? C21 C20 C19 122.57(16) . . ? C21 C20 H20 118.7 . . ? C19 C20 H20 118.7 . . ? C20 C21 C22 117.42(15) . . ? C20 C21 C25 121.57(17) . . ? C22 C21 C25 121.01(16) . . ? C23 C22 C21 122.11(15) . . ? C23 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? C22 C23 C3 119.94(15) . . ? C22 C23 C26 118.07(14) . . ? C3 C23 C26 121.99(14) . . ? C19 C24 H24A 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C19 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C25 H25A 109.5 . . ? C21 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C21 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C4 119.94(15) . . ? C28 C27 C34 117.37(15) . . ? C4 C27 C34 122.68(15) . . ? C29 C28 C27 122.08(16) . . ? C29 C28 H28 119.0 . . ? C27 C28 H28 119.0 . . ? C30 C29 C28 117.58(16) . . ? C30 C29 C33 121.41(17) . . ? C28 C29 C33 121.01(17) . . ? C29 C30 C31 122.64(16) . . ? C29 C30 H30 118.7 . . ? C31 C30 H30 118.7 . . ? C30 C31 C4 119.25(15) . . ? C30 C31 C32 116.21(15) . . ? C4 C31 C32 124.54(15) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C29 C33 H33A 109.5 . . ? C29 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C29 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C27 C34 H34A 109.5 . . ? C27 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C27 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? 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 Ge1 C3 1.9721(16) . ? Ge1 C4 1.9787(16) . ? Ge1 C1 2.0419(17) . ? Ge1 C2 2.0464(16) . ? O1 C1 1.215(2) . ? O2 C2 1.219(2) . ? C1 C5 1.497(2) . ? C2 C12 1.500(2) . ? C3 C19 1.411(2) . ? C3 C23 1.420(2) . ? C4 C27 1.415(2) . ? C4 C31 1.417(2) . ? C5 C6 1.404(2) . ? C5 C10 1.414(2) . ? C6 C7 1.388(2) . ? C6 H6 0.9500 . ? C7 C8 1.387(3) . ? C7 H7 0.9500 . ? C8 C9 1.388(3) . ? C8 H8 0.9500 . ? C9 C10 1.400(2) . ? C9 H9 0.9500 . ? C10 C11 1.502(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C17 1.399(2) . ? C12 C13 1.419(2) . ? C13 C14 1.397(3) . ? C13 C18 1.508(3) . ? C14 C15 1.386(3) . ? C14 H14 0.9500 . ? C15 C16 1.384(3) . ? C15 H15 0.9500 . ? C16 C17 1.390(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.398(2) . ? C19 C24 1.509(2) . ? C20 C21 1.388(2) . ? C20 H20 0.9500 . ? C21 C22 1.393(3) . ? C21 C25 1.506(2) . ? C22 C23 1.390(2) . ? C22 H22 0.9500 . ? C23 C26 1.509(2) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.396(2) . ? C27 C34 1.510(2) . ? C28 C29 1.390(3) . ? C28 H28 0.9500 . ? C29 C30 1.389(3) . ? C29 C33 1.508(3) . ? C30 C31 1.399(2) . ? C30 H30 0.9500 . ? C31 C32 1.515(2) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? 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 C1 C5 C6 156.86(17) . . . . ? Ge1 C1 C5 C6 -30.6(2) . . . . ? O1 C1 C5 C10 -25.0(3) . . . . ? Ge1 C1 C5 C10 147.54(14) . . . . ? C10 C5 C6 C7 1.9(3) . . . . ? C1 C5 C6 C7 -179.95(16) . . . . ? C5 C6 C7 C8 -2.0(3) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? C7 C8 C9 C10 2.4(3) . . . . ? C8 C9 C10 C5 -2.5(3) . . . . ? C8 C9 C10 C11 177.74(19) . . . . ? C6 C5 C10 C9 0.3(2) . . . . ? C1 C5 C10 C9 -177.77(16) . . . . ? C6 C5 C10 C11 -179.91(18) . . . . ? C1 C5 C10 C11 2.0(3) . . . . ? O2 C2 C12 C17 155.91(17) . . . . ? Ge1 C2 C12 C17 -30.9(2) . . . . ? O2 C2 C12 C13 -26.1(2) . . . . ? Ge1 C2 C12 C13 147.08(14) . . . . ? C17 C12 C13 C14 0.2(3) . . . . ? C2 C12 C13 C14 -177.76(17) . . . . ? C17 C12 C13 C18 179.24(17) . . . . ? C2 C12 C13 C18 1.3(3) . . . . ? C12 C13 C14 C15 -1.2(3) . . . . ? C18 C13 C14 C15 179.77(19) . . . . ? C13 C14 C15 C16 1.0(3) . . . . ? C14 C15 C16 C17 0.2(3) . . . . ? C15 C16 C17 C12 -1.2(3) . . . . ? C13 C12 C17 C16 1.0(3) . . . . ? C2 C12 C17 C16 179.00(17) . . . . ? C23 C3 C19 C20 3.2(2) . . . . ? Ge1 C3 C19 C20 -176.75(12) . . . . ? C23 C3 C19 C24 -177.85(16) . . . . ? Ge1 C3 C19 C24 2.2(2) . . . . ? C3 C19 C20 C21 1.5(3) . . . . ? C24 C19 C20 C21 -177.54(16) . . . . ? C19 C20 C21 C22 -4.4(3) . . . . ? C19 C20 C21 C25 174.62(17) . . . . ? C20 C21 C22 C23 2.7(3) . . . . ? C25 C21 C22 C23 -176.37(17) . . . . ? C21 C22 C23 C3 1.9(3) . . . . ? C21 C22 C23 C26 -177.54(16) . . . . ? C19 C3 C23 C22 -4.9(2) . . . . ? Ge1 C3 C23 C22 175.09(13) . . . . ? C19 C3 C23 C26 174.57(16) . . . . ? Ge1 C3 C23 C26 -5.5(2) . . . . ? C31 C4 C27 C28 -2.4(2) . . . . ? Ge1 C4 C27 C28 178.16(12) . . . . ? C31 C4 C27 C34 176.90(15) . . . . ? Ge1 C4 C27 C34 -2.5(2) . . . . ? C4 C27 C28 C29 0.8(2) . . . . ? C34 C27 C28 C29 -178.58(16) . . . . ? C27 C28 C29 C30 1.6(3) . . . . ? C27 C28 C29 C33 -178.01(16) . . . . ? C28 C29 C30 C31 -2.3(2) . . . . ? C33 C29 C30 C31 177.27(16) . . . . ? C29 C30 C31 C4 0.7(2) . . . . ? C29 C30 C31 C32 -178.55(15) . . . . ? C27 C4 C31 C30 1.7(2) . . . . ? Ge1 C4 C31 C30 -178.90(12) . . . . ? C27 C4 C31 C32 -179.14(15) . . . . ? Ge1 C4 C31 C32 0.3(2) . . . . ?