#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/90/2009081.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2009081 loop_ _publ_author_name 'White, Jonathan M.' _publ_section_title ; Trimethylgermylethyl p-nitrobenzoate ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1660 _journal_page_last 1662 _journal_paper_doi 10.1107/S0108270199007258 _journal_volume 55 _journal_year 1999 _chemical_formula_iupac '[Ge (C1 H3)3 (C9 H8 N1 O4)]' _chemical_formula_sum 'C12 H17 Ge N O4' _chemical_formula_weight 311.88 _chemical_melting_point .59E-58 _chemical_name_systematic ; 2-trimethylgermylethyl p-nitrobenzoate ; _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' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 96.920(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 12.670(2) _cell_length_b 7.3680(10) _cell_length_c 29.704(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 130.00(10) _cell_measurement_theta_max 30 _cell_measurement_theta_min 25 _cell_volume 2752.7(7) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'Process_data (Gable et al., 1994)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 130.0(10) _diffrn_measurement_device 'Enraf-Nonius CAD-4S' _diffrn_measurement_method \q2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.014 _diffrn_reflns_av_sigmaI/netI 0.0116 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3575 _diffrn_reflns_theta_max 63.98 _diffrn_reflns_theta_min 3.00 _diffrn_standards_decay_% insignificant _diffrn_standards_interval_time 160 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 3.101 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_correction_T_min 0.52 _exptl_absorpt_correction_type 'Gaussian (Sheldrick, 1976)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.505 _exptl_crystal_description Plate _exptl_crystal_F_000 1280 _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.018 _refine_diff_density_max 0.663 _refine_diff_density_min -0.444 _refine_ls_extinction_coef 0.00006(3) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_all 0.977 _refine_ls_goodness_of_fit_obs 0.992 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 232 _refine_ls_number_reflns 2248 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.008 _refine_ls_restrained_S_obs 0.992 _refine_ls_R_factor_all 0.032 _refine_ls_R_factor_obs .030 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0605P)^2^+5.0898P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.085 _refine_ls_wR_factor_obs .081 _reflns_number_observed 2113 _reflns_number_total 2251 _reflns_observed_criterion I>2\s(I) _cod_data_source_file ta1258.cif _cod_data_source_block jmwget _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_enum 1527 2010-12-29 10:47:43Z saulius 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 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0605P)^2^+5.0898P] where P = (Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0605P)^2^+5.0898P] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2009081 _cod_database_fobs_code 2009081 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_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Ge1 .0184(2) .0183(2) .0225(2) -.00231(10) .00327(12) .00009(10) O1 .0181(8) .0248(9) .0265(9) -.0061(7) .0020(7) -.0015(7) O2 .0191(9) .0220(9) .0386(10) -.0049(7) -.0026(7) -.0026(8) O3 .0399(11) .0311(10) .0237(10) -.0022(9) -.0015(8) -.0035(7) O4 .0267(10) .0365(11) .0325(10) -.0069(8) .0014(8) .0004(8) N1 .0260(11) .0165(10) .0261(11) .0025(9) -.0015(9) .0013(8) C1 .0226(13) .0217(14) .0297(13) -.0007(10) .0071(10) -.0008(10) C2 .0176(13) .0240(15) .0312(14) -.0052(10) .0045(10) .0020(10) C3 .032(2) .037(2) .0282(14) .0024(13) .0026(12) -.0002(12) C4 .0283(15) .033(2) .039(2) -.0083(13) .0032(12) .0077(13) C5 .0286(15) .032(2) .043(2) .0028(13) .0064(13) -.0076(13) C6 .0153(11) .0131(11) .0302(13) .0025(9) -.0037(9) -.0002(9) C7 .0172(12) .0098(11) .0296(13) .0035(9) -.0040(10) -.0014(9) C8 .0174(12) .0143(12) .0235(13) .0015(9) -.0049(10) -.0021(9) C9 .0160(12) .0144(11) .0276(12) -.0002(9) -.0043(9) -.0021(9) C10 .0218(12) .0115(11) .0243(12) .0045(9) -.0002(10) -.0005(8) C11 .0229(13) .0132(12) .0280(13) .0016(9) -.0079(11) -.0031(9) C12 .0172(12) .0130(11) .0309(13) .0000(9) -.0056(10) -.0004(10) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol Ge1 .81265(2) .03548(4) .193899(9) .01970(14) Uani d . 1 . Ge O1 .67197(14) .0048(2) .09913(6) .0232(4) Uani d . 1 . O O2 .55545(13) -.1626(2) .05348(6) .0270(4) Uani d . 1 . O O3 .8539(2) .0172(3) -.12158(6) .0320(5) Uani d . 1 . O O4 .97205(14) .1528(3) -.07471(6) .0321(4) Uani d . 1 . O N1 .8871(2) .0718(3) -.08360(7) .0232(5) Uani d . 1 . N C1 .6583(2) .0622(4) .17784(9) .0243(5) Uani d . 1 . C H1A .642(2) .184(4) .1735(8) .019(6) Uiso d . 1 . H H1B .622(2) .027(4) .2041(10) .025(7) Uiso d . 1 . H C2 .6104(2) -.0394(4) .13627(9) .0241(6) Uani d . 1 . C H2A .543(2) -.004(4) .1267(9) .016(6) Uiso d . 1 . H H2B .613(2) -.156(5) .1412(9) .026(7) Uiso d . 1 . H C3 .8413(3) .0482(4) .25968(10) .0324(6) Uani d . 1 . C H3A .909(3) .020(5) .2688(13) .048(10) Uiso d . 1 . H H3B .798(4) -.049(6) .2739(16) .083(15) Uiso d . 1 . H H3C .829(3) .160(6) .2696(13) .064(12) Uiso d . 1 . H C4 .8857(2) .2337(4) .16774(11) .0335(6) Uani d . 1 . C H4A .881(3) .230(6) .1382(16) .073(13) Uiso d . 1 . H H4B .943(4) .260(7) .1850(16) .092(16) Uiso d . 1 . H H4C .860(4) .347(8) .1726(15) .083(15) Uiso d . 1 . H C5 .8640(2) -.1941(4) .17262(11) .0345(6) Uani d . 1 . C H5A .814(3) -.285(6) .1741(14) .072(13) Uiso d . 1 . H H5B .929(4) -.219(6) .1876(14) .071(13) Uiso d . 1 . H H5C .884(3) -.189(6) .1423(14) .069(12) Uiso d . 1 . H C6 .6349(2) -.0694(3) .05909(8) .0201(5) Uani d . 1 . C C7 .7019(2) -.0266(3) .02267(9) .0194(5) Uani d . 1 . C C8 .8030(2) .0508(3) .03192(8) .0190(5) Uani d . 1 . C H8 .826(2) .078(4) .0596(10) .021(7) Uiso d . 1 . H C9 .8638(2) .0846(3) -.00253(8) .0199(5) Uani d . 1 . C H9 .929(2) .127(4) .0022(8) .014(6) Uiso d . 1 . H C10 .8222(2) .0407(3) -.04652(8) .0194(5) Uani d . 1 . C C11 .7216(2) -.0347(3) -.05688(9) .0223(5) Uani d . 1 . C H11 .697(2) -.064(4) -.0863(10) .024(7) Uiso d . 1 . H C12 .6621(2) -.0676(3) -.02202(9) .0210(5) Uani d . 1 . C H12 .596(2) -.116(4) -.0258(8) .018(6) Uiso d . 1 . H 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C4 Ge1 C5 109.27(14) y C4 Ge1 C3 108.99(14) y C5 Ge1 C3 109.79(14) y C4 Ge1 C1 109.61(12) y C5 Ge1 C1 111.74(12) y C3 Ge1 C1 107.38(12) y C6 O1 C2 114.6(2) ? O3 N1 O4 123.5(2) ? O3 N1 C10 118.6(2) ? O4 N1 C10 117.9(2) ? C2 C1 Ge1 116.1(2) y C2 C1 H1A 107.9(16) ? Ge1 C1 H1A 109.1(16) ? C2 C1 H1B 109.6(17) ? Ge1 C1 H1B 109.1(17) ? H1A C1 H1B 104.(2) ? O1 C2 C1 107.9(2) y O1 C2 H2A 105.7(17) ? C1 C2 H2A 112.7(17) ? O1 C2 H2B 109.6(19) ? C1 C2 H2B 110.5(19) ? H2A C2 H2B 110.(3) ? Ge1 C3 H3A 111.(2) ? Ge1 C3 H3B 110.(3) ? H3A C3 H3B 105.(3) ? Ge1 C3 H3C 111.(3) ? H3A C3 H3C 108.(3) ? H3B C3 H3C 113.(4) ? Ge1 C4 H4A 114.(3) ? Ge1 C4 H4B 110.(3) ? H4A C4 H4B 124.(4) ? Ge1 C4 H4C 115.(3) ? H4A C4 H4C 102.(4) ? H4B C4 H4C 89.(4) ? Ge1 C5 H5A 111.(3) ? Ge1 C5 H5B 110.(3) ? H5A C5 H5B 115.(4) ? Ge1 C5 H5C 114.(3) ? H5A C5 H5C 109.(4) ? H5B C5 H5C 98.(3) ? O2 C6 O1 123.2(2) ? O2 C6 C7 123.8(2) ? O1 C6 C7 112.9(2) ? C12 C7 C8 119.5(2) ? C12 C7 C6 118.3(2) ? C8 C7 C6 122.2(2) ? C9 C8 C7 120.6(2) ? C9 C8 H8 120.5(19) ? C7 C8 H8 118.9(19) ? C8 C9 C10 118.4(2) ? C8 C9 H9 123.2(16) ? C10 C9 H9 118.4(16) ? C9 C10 C11 122.4(2) ? C9 C10 N1 119.1(2) ? C11 C10 N1 118.5(2) ? C12 C11 C10 118.4(2) ? C12 C11 H11 121.1(18) ? C10 C11 H11 120.5(18) ? C11 C12 C7 120.7(2) ? C11 C12 H12 124.0(16) ? C7 C12 H12 115.3(16) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ge1 C4 . 1.941(3) y Ge1 C5 . 1.945(3) y Ge1 C3 . 1.946(3) y Ge1 C1 . 1.966(3) y O1 C6 . 1.341(3) ? O1 C2 . 1.463(3) y O2 C6 . 1.214(3) ? O3 N1 . 1.224(3) ? O4 N1 . 1.231(3) ? N1 C10 . 1.470(3) ? C1 C2 . 1.508(4) y C1 H1A . .93(3) ? C1 H1B . .99(3) ? C2 H2A . .91(3) ? C2 H2B . .87(3) ? C3 H3A . .89(4) ? C3 H3B . 1.02(5) ? C3 H3C . .89(4) ? C4 H4A . .87(4) ? C4 H4B . .86(5) ? C4 H4C . .91(5) ? C5 H5A . .92(5) ? C5 H5B . .90(4) ? C5 H5C . .96(4) ? C6 C7 . 1.487(4) ? C7 C12 . 1.395(4) ? C7 C8 . 1.399(3) ? C8 C9 . 1.376(4) ? C8 H8 . .86(3) ? C9 C10 . 1.387(3) ? C9 H9 . .88(3) ? C10 C11 . 1.390(4) ? C11 C12 . 1.374(4) ? C11 H11 . .92(3) ? C12 H12 . .91(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_publ_flag C4 Ge1 C1 C2 94.3(2) y C5 Ge1 C1 C2 -27.0(2) y C3 Ge1 C1 C2 -147.5(2) y C6 O1 C2 C1 -176.8(2) y Ge1 C1 C2 O1 -51.2(3) y C2 O1 C6 O2 1.6(3) ? C2 O1 C6 C7 -177.9(2) ? O2 C6 C7 C12 11.9(3) ? O1 C6 C7 C12 -168.6(2) ? O2 C6 C7 C8 -167.4(2) ? O1 C6 C7 C8 12.1(3) ? C12 C7 C8 C9 -0.9(3) ? C6 C7 C8 C9 178.4(2) ? C7 C8 C9 C10 0.3(3) ? C8 C9 C10 C11 0.4(3) ? C8 C9 C10 N1 -178.5(2) ? O3 N1 C10 C9 173.3(2) ? O4 N1 C10 C9 -7.2(3) ? O3 N1 C10 C11 -5.7(3) ? O4 N1 C10 C11 173.8(2) ? C9 C10 C11 C12 -0.5(3) ? N1 C10 C11 C12 178.5(2) ? C10 C11 C12 C7 -0.1(3) ? C8 C7 C12 C11 0.8(3) ? C6 C7 C12 C11 -178.6(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 24729976 2 PubChem 100992034