#------------------------------------------------------------------------------ #$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012053.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_2012053 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 687 _journal_page_last 689 _publ_section_title ; Ferrocenecarboxylic acid--1,4-diazabicyclo[2.2.2]octane (2/1): sheets built from O-H...N and C-H...O hydrogen bonds ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Zakaria, Choudhury M.' 'Ferguson, George' 'Lough, Alan J.' 'Glidewell, Christopher' _chemical_formula_moiety '2C11 H10 FeO2 , C6 H12 N2 ' _chemical_formula_sum 'C28 H32 Fe2 N2 O4' _chemical_formula_iupac '[Fe(C5 H5 )(C6 H5 O2 )]2, C6 H12 N2 ' _chemical_formula_weight 572.26 _symmetry_cell_setting monoclinic 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 11.3900(2) _cell_length_b 21.2256(6) _cell_length_c 11.7248(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.2144(12) _cell_angle_gamma 90.00 _cell_volume 2497.79(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _exptl_crystal_density_diffrn 1.522 _diffrn_ambient_temperature 150(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 Fe1 -.30212(5) .32894(2) .73618(6) .02281(17) Uani d . 1 . . Fe C11 -.1448(3) .30944(18) .7054(4) .0216(9) Uani d . 1 . . C C12 -.2636(3) .28326(18) .6059(4) .0242(9) Uani d . 1 . . C C13 -.3145(4) .23996(18) .6632(4) .0269(10) Uani d . 1 . . C C14 -.2277(4) .23994(18) .7988(4) .0277(10) Uani d . 1 . . C C15 -.1232(4) .28267(18) .8256(4) .0240(9) Uani d . 1 . . C C16 -.3229(4) .4241(2) .7275(5) .0396(11) Uani d . 1 . . C C17 -.4399(4) .3956(2) .6308(4) .0377(11) Uani d . 1 . . C C18 -.4901(4) .3558(2) .6939(4) .0367(11) Uani d . 1 . . C C19 -.4051(4) .3596(2) .8286(4) .0394(12) Uani d . 1 . . C C110 -.3007(4) .4020(2) .8501(5) .0422(12) Uani d . 1 . . C C111 -.0636(4) .35888(18) .6869(4) .0239(9) Uani d . 1 . . C O11 .0382(2) .37875(13) .7952(3) .0273(7) Uani d . 1 . . O O12 -.0882(2) .37755(13) .5786(3) .0335(7) Uani d . 1 . . O Fe2 .80577(5) .68571(2) .77234(6) .02123(17) Uani d . 1 . . Fe C21 .6405(4) .70488(18) .7895(4) .0214(9) Uani d . 1 . . C C22 .6289(4) .73248(17) .6728(4) .0228(9) Uani d . 1 . . C C23 .7354(4) .77554(18) .7087(4) .0268(10) Uani d . 1 . . C C24 .8144(4) .77451(18) .8457(4) .0267(10) Uani d . 1 . . C C25 .7561(3) .73115(18) .8960(4) .0240(9) Uani d . 1 . . C C26 .8185(4) .59010(19) .7716(4) .0343(11) Uani d . 1 . . C C27 .8109(4) .6153(2) .6564(4) .0378(11) Uani d . 1 . . C C28 .9213(4) .65610(19) .6923(4) .0298(10) Uani d . 1 . . C C29 .9959(4) .65638(19) .8285(4) .0290(10) Uani d . 1 . . C C210 .9332(4) .61524(19) .8782(4) .0326(10) Uani d . 1 . . C C211 .5560(3) .65521(18) .8020(4) .0226(9) Uani d . 1 . . C O21 .4630(3) .63272(13) .6895(3) .0285(7) Uani d . 1 . . O O22 .5702(2) .63807(12) .9071(2) .0289(7) Uani d . 1 . . O N1 .1798(3) .45997(14) .7505(3) .0220(7) Uani d . 1 . . N N2 .3182(3) .54638(15) .7207(3) .0247(8) Uani d . 1 . . N C31 .3133(4) .4624(2) .8640(4) .0429(12) Uani d . 1 . . C C32 .4001(4) .5109(2) .8408(4) .0365(11) Uani d . 1 . . C C41 .1140(4) .52135(18) .7351(4) .0339(11) Uani d . 1 . . C C42 .2021(4) .57453(17) .7257(4) .0279(9) Uani d . 1 . . C C51 .1942(4) .4470(2) .6341(4) .0351(11) Uani d . 1 . . C C52 .2686(4) .50188(18) .6096(4) .0286(10) Uani d . 1 . . C H12 -.3024 .2931 .5163 .029 Uiso calc R 1 . . H H13 -.3928 .2153 .6188 .032 Uiso calc R 1 . . H H14 -.2383 .2153 .8609 .033 Uiso calc R 1 . . H H15 -.0514 .2920 .9086 .029 Uiso calc R 1 . . H H16 -.2682 .4532 .7127 .047 Uiso calc R 1 . . H H17 -.4777 .4020 .5401 .045 Uiso calc R 1 . . H H18 -.5682 .3307 .6526 .044 Uiso calc R 1 . . H H19 -.4160 .3375 .8935 .047 Uiso calc R 1 . . H H110 -.2291 .4136 .9316 .051 Uiso calc R 1 . . H H1 .091(5) .411(2) .767(5) .095(18) Uiso d . 1 . . H H22 .5620 .7235 .5871 .027 Uiso calc R 1 . . H H23 .7516 .8009 .6508 .032 Uiso calc R 1 . . H H24 .8925 .7987 .8949 .032 Uiso calc R 1 . . H H25 .7880 .7212 .9848 .029 Uiso calc R 1 . . H H26 .7572 .5613 .7766 .041 Uiso calc R 1 . . H H27 .7440 .6064 .5707 .045 Uiso calc R 1 . . H H28 .9416 .6793 .6345 .036 Uiso calc R 1 . . H H29 1.0746 .6801 .8783 .035 Uiso calc R 1 . . H H210 .9627 .6061 .9669 .039 Uiso calc R 1 . . H H2 .406(6) .602(3) .704(6) .13(2) Uiso d . 1 . . H H31A .3555 .4203 .8793 .051 Uiso calc R 1 . . H H31B .3055 .4744 .9418 .051 Uiso calc R 1 . . H H32A .4404 .5403 .9149 .044 Uiso calc R 1 . . H H32B .4731 .4890 .8337 .044 Uiso calc R 1 . . H H41A .0983 .5292 .8100 .041 Uiso calc R 1 . . H H41B .0267 .5210 .6558 .041 Uiso calc R 1 . . H H42A .1497 .6000 .6469 .033 Uiso calc R 1 . . H H42B .2328 .6026 .8019 .033 Uiso calc R 1 . . H H51A .1051 .4418 .5582 .042 Uiso calc R 1 . . H H51B .2445 .4073 .6461 .042 Uiso calc R 1 . . H H52A .3445 .4853 .5996 .034 Uiso calc R 1 . . H H52B .2077 .5241 .5288 .034 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 Fe1 .0205(3) .0217(3) .0289(4) .0001(3) .0139(3) .0002(3) C11 .021(2) .022(2) .023(2) .0014(17) .0119(18) .0012(18) C12 .023(2) .026(2) .024(2) .0016(17) .0120(19) -.0021(19) C13 .027(2) .023(2) .037(3) -.0050(18) .020(2) -.005(2) C14 .035(2) .022(2) .035(3) .0001(18) .024(2) .001(2) C15 .020(2) .028(3) .025(2) .0019(17) .0111(19) .0038(19) C16 .039(3) .019(2) .067(4) .003(2) .030(3) -.001(2) C17 .032(3) .037(3) .046(3) .010(2) .020(2) .004(2) C18 .026(2) .030(3) .055(3) .0034(19) .020(2) .001(2) C19 .045(3) .039(3) .052(3) .015(2) .037(3) .009(2) C110 .031(3) .044(3) .047(3) .009(2) .014(2) -.019(3) C111 .020(2) .022(2) .032(3) .0046(17) .013(2) .003(2) O11 .0256(15) .0288(18) .0278(17) -.0067(12) .0128(14) .0010(13) O12 .0287(16) .042(2) .0294(18) -.0053(13) .0136(14) .0095(14) Fe2 .0201(3) .0205(3) .0253(4) -.0013(2) .0126(3) -.0018(3) C21 .023(2) .018(2) .031(2) -.0001(16) .0189(19) -.0009(18) C22 .025(2) .021(2) .026(2) .0021(17) .0149(19) -.0006(18) C23 .032(2) .026(2) .033(3) -.0015(18) .024(2) .0004(19) C24 .029(2) .024(2) .031(3) -.0077(18) .017(2) -.0095(19) C25 .024(2) .024(2) .023(2) -.0001(17) .0104(19) -.0006(18) C26 .033(2) .019(2) .056(3) -.0040(19) .026(2) -.004(2) C27 .034(3) .039(3) .040(3) .014(2) .017(2) -.011(2) C28 .032(2) .031(3) .036(3) .004(2) .023(2) .001(2) C29 .021(2) .028(3) .037(3) -.0020(18) .013(2) -.002(2) C210 .034(2) .032(3) .030(3) .006(2) .014(2) .003(2) C211 .018(2) .021(2) .030(3) .0053(17) .0114(19) .0042(19) O21 .0252(16) .0312(18) .0270(17) -.0073(13) .0107(14) -.0003(14) O22 .0298(16) .0315(18) .0276(17) -.0074(12) .0152(14) .0019(14) N1 .0216(17) .0140(18) .026(2) -.0003(13) .0081(16) -.0002(15) N2 .0162(17) .022(2) .030(2) -.0030(14) .0055(15) .0006(16) C31 .030(2) .042(3) .043(3) -.008(2) .006(2) .019(2) C32 .025(2) .035(3) .034(3) -.0050(19) .001(2) .014(2) C41 .035(2) .021(2) .052(3) -.0031(19) .026(2) -.001(2) C42 .035(2) .016(2) .035(3) .0036(19) .019(2) -.002(2) C51 .040(2) .034(3) .039(3) -.012(2) .024(2) -.006(2) C52 .034(2) .023(2) .035(3) -.0018(19) .022(2) -.003(2) 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 Fe1 C11 . 2.031(3) no Fe1 C12 . 2.025(4) no Fe1 C13 . 2.051(4) no Fe1 C14 . 2.059(4) no Fe1 C15 . 2.049(4) no Fe1 C16 . 2.030(4) no Fe1 C17 . 2.038(4) no Fe1 C18 . 2.038(4) no Fe1 C19 . 2.044(4) no Fe1 C110 . 2.042(4) no C11 C12 . 1.417(5) no C11 C15 . 1.430(5) no C11 C111 . 1.481(5) no C12 C13 . 1.414(5) no C12 H12 . .95 no C13 C14 . 1.421(5) no C13 H13 . .95 no C14 C15 . 1.409(5) no C14 H14 . .95 no C15 H15 . .95 no C16 C17 . 1.414(6) no C16 C110 . 1.415(6) no C16 H16 . .95 no C17 C18 . 1.409(5) no C17 H17 . .95 no C18 C19 . 1.412(6) no C18 H18 . .95 no C19 C110 . 1.417(6) no C19 H19 . .95 no C110 H110 . .95 no C111 O12 . 1.229(4) y C111 O11 . 1.320(4) y O11 H1 . 1.06(6) no Fe2 C21 . 2.027(3) no Fe2 C22 . 2.045(4) no Fe2 C23 . 2.066(4) no Fe2 C24 . 2.055(4) no Fe2 C25 . 2.032(4) no Fe2 C26 . 2.035(4) no Fe2 C27 . 2.040(4) no Fe2 C28 . 2.044(3) no Fe2 C29 . 2.040(4) no Fe2 C210 . 2.045(4) no C21 C22 . 1.436(5) no C21 C25 . 1.432(5) no C21 C211 . 1.481(5) no C22 C23 . 1.415(5) no C22 H22 . .95 no C23 C24 . 1.423(5) no C23 H23 . .95 no C24 C25 . 1.416(5) no C24 H24 . .95 no C25 H25 . .95 no C26 C27 . 1.417(6) no C26 C210 . 1.417(5) no C26 H26 . .95 no C27 C28 . 1.418(5) no C27 H27 . .95 no C28 C29 . 1.410(5) no C28 H28 . .95 no C29 C210 . 1.417(5) no C29 H29 . .95 no C210 H210 . .95 no N1 C31 . 1.474(5) y N1 C41 . 1.471(5) y N1 C51 . 1.476(5) y N1 H1 . 1.52(5) no C211 O22 . 1.220(4) y C211 O21 . 1.330(4) y O21 H2 . .99(7) no N2 C32 . 1.477(5) y N2 C42 . 1.477(4) y N2 C52 . 1.487(5) y C31 C32 . 1.538(5) no C31 H31A . .99 no C31 H31B . .99 no C32 H32A . .99 no C32 H32B . .99 no C41 C42 . 1.548(5) no C41 H41A . .99 no C41 H41B . .99 no C42 H42A . .99 no C42 H42B . .99 no C51 C52 . 1.546(5) no C51 H51A . .99 no C51 H51B . .99 no C52 H52A . .99 no C52 H52B . .99 no _cod_database_code 2012053