#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:08:28 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201955 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/73/2007314.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_2007314 loop_ _publ_author_name 'Crous, Renier' 'Holzapfel, Cedric W.' 'Kruger, Gert J.' _publ_section_title ; [3-(tert-Butoxycarbonylamino)-4-pyridyl]trimethyltin(IV), a Tetraorganotin Compound Containing an Unexpected Intramolecular Sn···O Interaction ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 760 _journal_page_last 762 _journal_paper_doi 10.1107/S0108270197017459 _journal_volume 54 _journal_year 1998 _chemical_formula_iupac '[Sn(CH3)3 (C10 H13 N2 O2)]' _chemical_formula_moiety 'C13 H22 N2 O2 Sn' _chemical_formula_sum 'C13 H22 N2 O2 Sn' _chemical_formula_weight 357.01 _chemical_name_systematic ; N-(tert-Butoxycarbonyl)-3-Amino-4-(Trimethylstannyl)pyridine ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90.00 _cell_angle_beta 92.948(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 8.7829(7) _cell_length_b 9.622(2) _cell_length_c 9.8535(11) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 19.8 _cell_measurement_theta_min 18.0 _cell_volume 831.6(2) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'CAD-4 Software' _computing_molecular_graphics 'Xtal (Hall et al., 1995)' _computing_publication_material Xtal _computing_structure_refinement SHELXL97 _computing_structure_solution 'SHELXL97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4F' _diffrn_measurement_method \w--2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5396 _diffrn_reflns_theta_full 29.90 _diffrn_reflns_theta_max 29.90 _diffrn_reflns_theta_min 3.02 _diffrn_standards_decay_% 0.0 _diffrn_standards_interval_count 345 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.534 _exptl_absorpt_correction_T_max 0.585 _exptl_absorpt_correction_T_min 0.553 _exptl_absorpt_correction_type psi-scan_(North_et_al.,_1968) _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 360 _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.839 _refine_diff_density_min -0.497 _refine_ls_abs_structure_details 'Flack (1983) parameter = -0.03(2)' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 169 _refine_ls_number_reflns 4842 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.114 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0269 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+0.0994P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.0691 _reflns_number_gt 4720 _reflns_number_total 4842 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cf1218.cif _cod_data_source_block rau35 _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+0.0994P] 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^)+(0.0374P)^2^+0.0994P] 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 'P 21' _cod_original_formula_sum 'C13 H22 N2 O2 Sn1' _cod_database_code 2007314 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Sn .031347(16) .24991(2) .224847(15) .05316(6) Uani d . 1 . . Sn N1 .3867(3) .6018(2) .4337(3) .0540(5) Uani d . 1 . . N N2 .4108(2) .2327(3) .35187(19) .0456(5) Uani d . 1 . . N H2 .4487 .1968 .4261 .055 Uiso calc R 1 . . H O1 .3518(3) .1904(2) .1285(2) .0593(5) Uani d . 1 . . O O2 .4982(3) .0426(2) .2584(2) .0537(4) Uani d . 1 . . O C2 .0187(4) .2352(7) .0084(3) .0802(11) Uani d . 1 . . C H2A .0982 .2902 -.0278 .120 Uiso calc R 1 . . H H2B -.0786 .2688 -.0263 .120 Uiso calc R 1 . . H H2C .0307 .1400 -.0180 .120 Uiso calc R 1 . . H C3 .0605(6) .0519(5) .3227(5) .0881(12) Uani d . 1 . . C H3A -.0105 .0434 .3931 .132 Uiso calc R 1 . . H H3B .1626 .0445 .3616 .132 Uiso calc R 1 . . H H3C .0425 -.0208 .2571 .132 Uiso calc R 1 . . H C1 -.1774(4) .3388(5) .2875(5) .0800(10) Uani d . 1 . . C H1A -.1693 .3564 .3834 .120 Uiso calc R 1 . . H H1B -.2598 .2753 .2673 .120 Uiso calc R 1 . . H H1C -.1966 .4245 .2397 .120 Uiso calc R 1 . . H C4 .1985(3) .3977(2) .3048(2) .0413(4) Uani d . 1 . . C C5 .3460(3) .3668(2) .3565(2) .0395(4) Uani d . 1 . . C C6 .4330(3) .4710(3) .4194(3) .0490(5) Uani d . 1 . . C H6 .5302 .4479 .4541 .059 Uiso calc R 1 . . H C7 .2488(4) .6326(3) .3805(3) .0552(6) Uani d . 1 . . C H7 .2148 .7238 .3864 .066 Uiso calc R 1 . . H C8 .1538(3) .5360(3) .3170(3) .0509(5) Uani d . 1 . . C H8 .0583 .5635 .2818 .061 Uiso calc R 1 . . H C9 .4158(3) .1577(2) .2353(3) .0439(5) Uani d . 1 . . C C10 .5280(4) -.0559(3) .1478(3) .0534(6) Uani d . 1 . . C C11 .3791(5) -.1142(4) .0883(5) .0813(11) Uani d . 1 . . C H11A .3994 -.1791 .0175 .122 Uiso calc R 1 . . H H11B .3169 -.0398 .0515 .122 Uiso calc R 1 . . H H11C .3264 -.1607 .1582 .122 Uiso calc R 1 . . H C12 .6199(6) .0127(4) .0431(4) .0832(12) Uani d . 1 . . C H12A .5594 .0828 -.0034 .125 Uiso calc R 1 . . H H12B .6507 -.0555 -.0212 .125 Uiso calc R 1 . . H H12C .7087 .0548 .0866 .125 Uiso calc R 1 . . H C13 .6205(5) -.1680(4) .2223(4) .0723(9) Uani d . 1 . . C H13A .6483 -.2383 .1590 .108 Uiso calc R 1 . . H H13B .5608 -.2091 .2907 .108 Uiso calc R 1 . . H H13C .7111 -.1277 .2645 .108 Uiso calc R 1 . . H 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 Sn .04329(8) .06300(10) .05280(9) -.01008(9) -.00113(6) -.00743(10) N1 .0634(14) .0406(10) .0571(12) -.0065(9) -.0059(10) -.0049(9) N2 .0484(9) .0433(13) .0441(8) .0059(9) -.0066(7) -.0017(9) O1 .0778(13) .0542(10) .0447(9) .0143(9) -.0077(9) -.0061(8) O2 .0646(11) .0436(9) .0525(9) .0128(8) -.0014(8) -.0050(7) C2 .0591(15) .123(3) .0576(14) -.013(3) -.0052(11) -.015(3) C3 .096(3) .073(2) .096(3) -.027(2) .011(2) .010(2) C1 .0503(16) .105(3) .084(2) -.0017(18) .0002(15) -.008(2) C4 .0406(10) .0444(11) .0388(10) .0005(9) -.0005(8) -.0014(8) C5 .0415(10) .0373(10) .0393(10) -.0001(8) -.0009(8) -.0012(8) C6 .0456(12) .0465(12) .0539(13) -.0036(10) -.0078(10) -.0048(10) C7 .0699(17) .0376(11) .0574(15) .0048(11) -.0019(12) .0002(10) C8 .0486(13) .0515(13) .0518(13) .0065(11) -.0055(10) .0006(11) C9 .0462(11) .0372(10) .0483(12) -.0003(9) .0015(9) -.0019(9) C10 .0616(16) .0373(11) .0618(15) .0017(10) .0084(12) -.0056(10) C11 .081(2) .0585(18) .103(3) -.0045(17) -.010(2) -.0257(19) C12 .113(3) .0515(17) .089(3) .0025(18) .044(2) .0005(16) C13 .081(2) .0508(16) .085(2) .0183(15) .0104(17) -.0022(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables 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' O O 0.0106 0.0060 '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' Sn Sn -0.6537 1.4246 '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 C2 Sn C1 108.22(17) yes C2 Sn C3 112.9(2) yes C1 Sn C3 108.03(19) yes C2 Sn C4 114.02(15) yes C1 Sn C4 101.97(14) yes C3 Sn C4 110.93(15) yes C7 N1 C6 116.5(2) ? C9 N2 C5 122.9(2) ? C9 N2 H2 118.6 ? C5 N2 H2 118.6 ? C9 O2 C10 121.4(2) ? Sn C2 H2A 109.5 ? Sn C2 H2B 109.5 ? H2A C2 H2B 109.5 ? Sn C2 H2C 109.5 ? H2A C2 H2C 109.5 ? H2B C2 H2C 109.5 ? Sn C3 H3A 109.5 ? Sn C3 H3B 109.5 ? H3A C3 H3B 109.5 ? Sn C3 H3C 109.5 ? H3A C3 H3C 109.5 ? H3B C3 H3C 109.5 ? Sn C1 H1A 109.5 ? Sn C1 H1B 109.5 ? H1A C1 H1B 109.5 ? Sn C1 H1C 109.5 ? H1A C1 H1C 109.5 ? H1B C1 H1C 109.5 ? C8 C4 C5 115.5(2) ? C8 C4 Sn 118.05(18) ? C5 C4 Sn 126.25(17) ? C6 C5 C4 119.2(2) ? C6 C5 N2 117.5(2) ? C4 C5 N2 123.3(2) ? N1 C6 C5 124.5(2) ? N1 C6 H6 117.8 ? C5 C6 H6 117.8 ? N1 C7 C8 123.2(2) ? N1 C7 H7 118.4 ? C8 C7 H7 118.4 ? C7 C8 C4 121.1(3) ? C7 C8 H8 119.4 ? C4 C8 H8 119.4 ? O1 C9 O2 125.9(2) ? O1 C9 N2 124.3(2) ? O2 C9 N2 109.7(2) ? O2 C10 C12 110.3(2) ? O2 C10 C11 110.0(3) ? C12 C10 C11 112.5(4) ? O2 C10 C13 102.1(3) ? C12 C10 C13 110.7(3) ? C11 C10 C13 110.8(3) ? 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 ? C10 C12 H12A 109.5 ? C10 C12 H12B 109.5 ? H12A C12 H12B 109.5 ? C10 C12 H12C 109.5 ? H12A C12 H12C 109.5 ? H12B C12 H12C 109.5 ? C10 C13 H13A 109.5 ? C10 C13 H13B 109.5 ? H13A C13 H13B 109.5 ? C10 C13 H13C 109.5 ? H13A C13 H13C 109.5 ? H13B C13 H13C 109.5 ? 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 Sn C2 . 2.134(3) yes Sn C1 . 2.142(4) yes Sn C3 . 2.145(5) yes Sn C4 . 2.163(2) yes Sn O1 . 3.070(3) yes N1 C7 . 1.328(4) ? N1 C6 . 1.332(4) ? N2 C9 . 1.359(3) ? N2 C5 . 1.412(3) ? N2 H2 . .8600 ? O1 C9 . 1.208(3) ? O2 C9 . 1.337(3) ? O2 C10 . 1.477(3) ? C2 H2A . .9600 ? C2 H2B . .9600 ? C2 H2C . .9600 ? C3 H3A . .9600 ? C3 H3B . .9600 ? C3 H3C . .9600 ? C1 H1A . .9600 ? C1 H1B . .9600 ? C1 H1C . .9600 ? C4 C8 . 1.395(4) ? C4 C5 . 1.399(3) ? C5 C6 . 1.387(3) ? C6 H6 . .9300 ? C7 C8 . 1.377(4) ? C7 H7 . .9300 ? C8 H8 . .9300 ? C10 C12 . 1.496(5) ? C10 C11 . 1.513(5) ? C10 C13 . 1.517(5) ? C11 H11A . .9600 ? C11 H11B . .9600 ? C11 H11C . .9600 ? C12 H12A . .9600 ? C12 H12B . .9600 ? C12 H12C . .9600 ? C13 H13A . .9600 ? C13 H13B . .9600 ? C13 H13C . .9600 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2 N1 2_646 0.860 2.152 2.971(3) 159.14 yes 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 C2 Sn C4 C8 87.0(3) ? C1 Sn C4 C8 -29.4(2) ? C3 Sn C4 C8 -144.2(2) ? C2 Sn C4 C5 -98.5(3) ? C1 Sn C4 C5 145.1(2) ? C3 Sn C4 C5 30.3(3) ? C8 C4 C5 C6 2.6(3) ? Sn C4 C5 C6 -172.09(19) ? C8 C4 C5 N2 -179.5(2) ? Sn C4 C5 N2 5.9(3) yes C9 N2 C5 C6 -129.1(3) ? C9 N2 C5 C4 52.9(3) ? C7 N1 C6 C5 -1.5(4) ? C4 C5 C6 N1 -0.8(4) ? N2 C5 C6 N1 -178.9(3) ? C6 N1 C7 C8 2.0(4) ? N1 C7 C8 C4 -0.1(5) ? C5 C4 C8 C7 -2.2(4) ? Sn C4 C8 C7 172.9(2) ? C10 O2 C9 O1 4.0(4) ? C10 O2 C9 N2 -177.5(2) ? C5 N2 C9 O1 -8.5(4) ? C5 N2 C9 O2 173.0(2) ? C9 O2 C10 C12 63.5(4) ? C9 O2 C10 C11 -61.2(4) ? C9 O2 C10 C13 -178.8(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 9614582