data_2010734 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 324 _journal_page_last 326 _publ_section_title ; Complexes of dimethyltin dihalides with N-methylpyrrolidinone, C~12~H~24~N~2~O~2~X~2~Sn (X = Cl, Br or I) ; loop_ _publ_author_name 'K\"onig, Uwe-Christoph' 'Berkei, Michael' 'Neikes, Frank' 'Preut, Hans' 'Mitchell, Terence Nigel' _chemical_formula_sum 'C12 H24 Cl2 N2 O2 Sn' _chemical_formula_iupac '[SnCl~2~(CH~3~)~2~(C~5~H~9~NO)~2~]' _chemical_formula_weight 417.92 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 7.8320(16) _cell_length_b 25.703(5) _cell_length_c 8.9840(18) _cell_angle_alpha 90.00 _cell_angle_beta 111.38(3) _cell_angle_gamma 90.00 _cell_volume 1684.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _exptl_crystal_density_diffrn 1.648 _diffrn_ambient_temperature 173(2) 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 Sn1 .55506(2) .875738(6) .147222(16) .02559(7) Uani d . 1 . . Sn Cl1 .44742(8) .81796(2) -.08912(7) .03417(15) Uani d . 1 . . Cl Cl2 .28036(8) .93176(2) .03559(6) .03249(14) Uani d . 1 . . Cl C1 .4510(3) .83341(8) .2969(3) .0340(6) Uani d . 1 . . C H1A .4597 .7968 .2794 .051 Uiso calc R 1 . . H H1B .3249 .8426 .2728 .051 Uiso calc R 1 . . H H1C .5210 .8415 .4066 .051 Uiso calc R 1 . . H C2 .7403(3) .91839(8) .0742(3) .0322(6) Uani d . 1 . . C H2A .7093 .9547 .0682 .048 Uiso calc R 1 . . H H2B .7336 .9065 -.0291 .048 Uiso calc R 1 . . H H2C .8626 .9135 .1500 .048 Uiso calc R 1 . . H O1 .8247(2) .82031(6) .26626(19) .0378(4) Uani d . 1 . . O C11 .8474(3) .77224(9) .2870(3) .0295(5) Uani d . 1 . . C C12 .7258(3) .73021(8) .1893(3) .0374(6) Uani d . 1 . . C H12A .7031 .7352 .0767 .056 Uiso calc R 1 . . H H12B .6093 .7300 .2043 .056 Uiso calc R 1 . . H C13 .8288(4) .67986(9) .2489(3) .0412(6) Uani d . 1 . . C H13A .8837 .6672 .1749 .062 Uiso calc R 1 . . H H13B .7476 .6533 .2624 .062 Uiso calc R 1 . . H C14 .9765(3) .69428(9) .4096(3) .0412(6) Uani d . 1 . . C H14A .9409 .6836 .4978 .062 Uiso calc R 1 . . H H14B 1.0929 .6782 .4218 .062 Uiso calc R 1 . . H N1 .9878(3) .75095(7) .4021(2) .0324(5) Uani d . 1 . . N C15 1.1324(3) .77999(10) .5218(3) .0427(7) Uani d . 1 . . C H15A 1.1127 .8166 .5012 .064 Uiso calc R 1 . . H H15B 1.2489 .7704 .5175 .064 Uiso calc R 1 . . H H15C 1.1312 .7722 .6260 .064 Uiso calc R 1 . . H O2 .6735(2) .93132(6) .38595(17) .0361(4) Uani d . 1 . . O C21 .6857(3) .97906(8) .4134(2) .0259(5) Uani d . 1 . . C C22 .5857(3) 1.02161(8) .3011(2) .0305(5) Uani d . 1 . . C H22A .4543 1.0159 .2631 .046 Uiso calc R 1 . . H H22B .6237 1.0232 .2098 .046 Uiso calc R 1 . . H C23 .6370(4) 1.07148(9) .3986(3) .0427(7) Uani d . 1 . . C H23A .5321 1.0853 .4186 .064 Uiso calc R 1 . . H H23B .6799 1.0976 .3424 .064 Uiso calc R 1 . . H C24 .7897(3) 1.05659(8) .5557(3) .0339(6) Uani d . 1 . . C H24A .9066 1.0707 .5609 .051 Uiso calc R 1 . . H H24B .7629 1.0692 .6467 .051 Uiso calc R 1 . . H N2 .7915(3) .99975(7) .5524(2) .0277(4) Uani d . 1 . . N C25 .9070(3) .96993(9) .6887(3) .0361(6) Uani d . 1 . . C H25A .8876 .9335 .6656 .054 Uiso calc R 1 . . H H25B .8768 .9783 .7803 .054 Uiso calc R 1 . . H H25C 1.0333 .9783 .7104 .054 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 Sn1 .02834(10) .02253(10) .02124(9) -.00205(7) .00352(7) .00138(6) Cl1 .0404(4) .0332(3) .0242(3) -.0062(3) .0063(3) -.0047(3) Cl2 .0303(3) .0328(3) .0296(3) .0037(3) .0053(3) .0060(2) C1 .0496(16) .0247(12) .0277(12) -.0025(11) .0139(11) .0000(10) C2 .0342(13) .0252(12) .0362(13) -.0035(10) .0117(11) -.0012(10) O1 .0342(10) .0230(8) .0452(10) .0004(7) .0012(8) .0030(7) C11 .0305(14) .0300(13) .0295(12) .0012(11) .0128(11) .0018(11) C12 .0426(16) .0268(12) .0366(13) -.0032(11) .0070(12) -.0023(11) C13 .0468(16) .0278(13) .0532(16) -.0026(12) .0233(13) -.0054(12) C14 .0386(15) .0298(13) .0546(16) .0089(11) .0163(13) .0116(12) N1 .0286(11) .0281(10) .0379(11) .0045(9) .0092(9) .0035(9) C15 .0349(15) .0439(15) .0401(15) .0004(12) .0026(12) -.0050(12) O2 .0479(11) .0270(9) .0249(8) -.0030(8) .0032(8) -.0011(7) C21 .0264(13) .0279(12) .0246(11) -.0024(10) .0108(10) -.0004(10) C22 .0316(14) .0333(13) .0246(12) .0006(11) .0078(10) .0034(10) C23 .0598(18) .0272(12) .0347(14) .0066(12) .0097(13) .0014(11) C24 .0423(15) .0280(12) .0304(13) -.0031(11) .0118(11) -.0043(10) N2 .0314(11) .0258(9) .0217(10) -.0016(8) .0046(8) -.0004(8) C25 .0375(15) .0373(14) .0260(12) -.0005(11) .0027(11) .0027(11) 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 Sn1 C2 . 2.105(2) ? Sn1 C1 . 2.111(2) ? Sn1 O1 . 2.4464(16) ? Sn1 O2 . 2.4598(15) ? Sn1 Cl1 . 2.4737(7) ? Sn1 Cl2 . 2.4768(8) ? C1 H1A . .9600 ? C1 H1B . .9600 ? C1 H1C . .9600 ? C2 H2A . .9600 ? C2 H2B . .9600 ? C2 H2C . .9600 ? O1 C11 . 1.253(3) ? C11 N1 . 1.322(3) ? C11 C12 . 1.495(3) ? C12 C13 . 1.516(3) ? C12 H12A . .9700 ? C12 H12B . .9700 ? C13 C14 . 1.531(3) ? C13 H13A . .9700 ? C13 H13B . .9700 ? C14 N1 . 1.463(3) ? C14 H14A . .9700 ? C14 H14B . .9700 ? N1 C15 . 1.452(3) ? C15 H15A . .9600 ? C15 H15B . .9600 ? C15 H15C . .9600 ? O2 C21 . 1.248(2) ? C21 N2 . 1.332(3) ? C21 C22 . 1.500(3) ? C22 C23 . 1.522(3) ? C22 H22A . .9700 ? C22 H22B . .9700 ? C23 C24 . 1.529(3) ? C23 H23A . .9700 ? C23 H23B . .9700 ? C24 N2 . 1.462(3) ? C24 H24A . .9700 ? C24 H24B . .9700 ? N2 C25 . 1.448(3) ? C25 H25A . .9600 ? C25 H25B . .9600 ? C25 H25C . .9600 ?