data_2014640 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2005 _journal_volume 61 _journal_page_first m55 _journal_page_last m57 _publ_section_title ; Charge-assisted N---H...I and C---H...I hydrogen bonding in (1R,2S)-2-methoxymethyl-1-(ferrocenylmethyl)pyrrolidinium iodide ; loop_ _publ_author_name ' Palusiak, Marcin' ' Janowska, Izabela' ' Zakrzewski, Janusz' ' Grabowski, S\/lawomir J.' _chemical_formula_moiety 'C17 H24 Fe N O +, I -' _chemical_formula_sum 'C17 H24 Fe I N O' _chemical_formula_iupac '[Fe (C5 H5) (C12 H19 N O)] I' _chemical_formula_weight 441.12 _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.777(2) _cell_length_b 11.575(3) _cell_length_c 20.160(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1814.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.615 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 I 0.71391(3) 0.26809(2) 0.195759(14) 0.07114(10) Uani d . 1 . . I Fe 0.26848(8) -0.01584(4) 0.04636(2) 0.05045(15) Uani d . 1 . . Fe O82 0.1757(4) 0.1504(2) 0.30972(15) 0.0694(8) Uani d . 1 . . O N7 0.1553(3) 0.2806(2) 0.17816(12) 0.0429(7) Uani d . 1 . . N H7 0.0408 0.2672 0.1833 0.051 Uiso calc R 1 . . H C1A 0.1725(5) 0.1268(3) 0.09113(17) 0.0424(10) Uani d . 1 . . C C2A 0.0403(5) 0.0438(4) 0.0822(2) 0.0569(11) Uani d . 1 . . C H2A -0.0254 0.0103 0.1156 0.068 Uiso calc R 1 . . H C3A 0.0265(6) 0.0212(4) 0.0136(2) 0.0724(15) Uani d . 1 . . C H3A -0.05 -0.0302 -0.006 0.087 Uiso calc R 1 . . H C4A 0.1459(7) 0.0883(4) -0.0193(2) 0.0779(15) Uani d . 1 . . C H4A 0.1638 0.0892 -0.0649 0.093 Uiso calc R 1 . . H C5A 0.2355(6) 0.1546(3) 0.02713(19) 0.0649(12) Uani d . 1 . . C H5A 0.3217 0.2078 0.0177 0.078 Uiso calc R 1 . . H C1B 0.4553(11) -0.0803(7) 0.1058(4) 0.129(3) Uani d . 1 . . C H1B 0.4881 -0.0507 0.1468 0.154 Uiso calc R 1 . . H C2B 0.3291(9) -0.1640(6) 0.0935(4) 0.109(2) Uani d . 1 . . C H2B 0.2601 -0.2002 0.1249 0.131 Uiso calc R 1 . . H C3B 0.3265(7) -0.1826(4) 0.0260(3) 0.0884(16) Uani d . 1 . . C H3B 0.2563 -0.2356 0.0044 0.106 Uiso calc R 1 . . H C4B 0.4410(8) -0.1122(6) -0.0042(3) 0.0943(17) Uani d . 1 . . C H4B 0.4607 -0.1071 -0.0496 0.113 Uiso calc R 1 . . H C5B 0.5218(6) -0.0505(6) 0.0435(5) 0.115(2) Uani d . 1 . . C H5B 0.6083 0.0034 0.0361 0.138 Uiso calc R 1 . . H C6 0.2369(5) 0.1691(3) 0.15622(16) 0.0538(10) Uani d . 1 . . C H62 0.3604 0.18 0.1533 0.065 Uiso calc R 1 . . H H61 0.2154 0.1105 0.1896 0.065 Uiso calc R 1 . . H C8 0.2227(6) 0.3275(3) 0.24370(17) 0.0501(9) Uani d . 1 . . C H8 0.3478 0.3176 0.2453 0.06 Uiso calc R 1 . . H C81 0.1429(4) 0.2695(4) 0.3038(2) 0.0641(10) Uani d . 1 . . C H811 0.1849 0.3078 0.3434 0.077 Uiso calc R 1 . . H H812 0.0194 0.2809 0.3021 0.077 Uiso calc R 1 . . H C83 0.3441(6) 0.1247(4) 0.3327(2) 0.0827(16) Uani d . 1 . . C H831 0.427 0.1534 0.3015 0.124 Uiso calc R 1 . . H H832 0.3569 0.0426 0.3371 0.124 Uiso calc R 1 . . H H833 0.3621 0.1608 0.375 0.124 Uiso calc R 1 . . H C9 0.1810(7) 0.4546(3) 0.2396(2) 0.0843(15) Uani d . 1 . . C H92 0.0677 0.4698 0.2577 0.101 Uiso calc R 1 . . H H91 0.2649 0.4996 0.2642 0.101 Uiso calc R 1 . . H C10 0.1868(7) 0.4844(3) 0.1679(2) 0.0897(15) Uani d . 1 . . C H102 0.092 0.5353 0.1568 0.108 Uiso calc R 1 . . H H101 0.2936 0.5238 0.1576 0.108 Uiso calc R 1 . . H C11 0.1743(7) 0.3768(3) 0.12967(19) 0.0741(15) Uani d . 1 . . C H111 0.277 0.3659 0.1031 0.089 Uiso calc R 1 . . H H112 0.0756 0.3795 0.1003 0.089 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 C83 0.091(4) 0.070(3) 0.087(4) 0.001(3) -0.002(3) 0.022(3) I 0.03903(11) 0.07530(18) 0.0991(2) 0.00156(14) 0.00217(17) 0.02420(17) Fe 0.0531(4) 0.0514(3) 0.0468(3) 0.0055(3) 0.0028(3) -0.0049(2) O82 0.074(2) 0.071(2) 0.0636(19) -0.0209(15) 0.0011(19) -0.0020(18) N7 0.0370(14) 0.0415(17) 0.050(2) -0.0004(13) 0.0027(12) -0.0027(16) C1A 0.043(3) 0.046(2) 0.038(2) 0.0025(18) 0.0050(19) -0.0045(18) C2A 0.050(3) 0.065(3) 0.055(3) 0.001(2) 0.002(2) -0.007(2) C3A 0.069(3) 0.076(4) 0.073(4) 0.015(3) -0.023(3) -0.028(3) C4A 0.118(4) 0.073(3) 0.044(3) 0.029(3) 0.001(3) -0.004(3) C5A 0.084(4) 0.050(2) 0.061(3) 0.004(2) 0.016(3) 0.002(2) C1B 0.142(7) 0.135(7) 0.109(6) 0.097(6) -0.075(5) -0.049(5) C2B 0.141(6) 0.101(5) 0.086(5) 0.062(4) 0.034(4) 0.036(3) C3B 0.096(4) 0.049(3) 0.120(5) 0.009(3) 0.005(4) -0.014(3) C4B 0.095(5) 0.098(5) 0.090(4) 0.032(4) 0.026(4) -0.007(4) C5B 0.048(3) 0.096(5) 0.200(8) 0.007(3) -0.014(5) -0.010(6) C6 0.045(3) 0.056(2) 0.060(2) 0.0053(19) -0.001(2) -0.0201(19) C8 0.046(2) 0.048(2) 0.056(2) -0.005(2) -0.004(2) -0.0147(18) C81 0.056(2) 0.079(3) 0.058(3) 0.008(2) 0.001(2) -0.014(3) C9 0.110(4) 0.051(3) 0.092(4) 0.012(3) -0.016(3) -0.024(3) C10 0.116(4) 0.047(3) 0.105(4) 0.012(3) -0.010(3) -0.002(3) C11 0.107(5) 0.055(3) 0.060(3) -0.008(3) 0.017(3) 0.009(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 Fe C1A . 2.025(3) no Fe C2A . 2.037(4) no Fe C3A . 2.040(4) no Fe C4A . 2.029(4) no Fe C5A . 2.027(4) no Fe C1B . 2.026(5) no Fe C2B . 2.017(5) no Fe C3B . 2.024(4) no Fe C4B . 2.021(5) no Fe C5B . 2.011(5) no O82 C81 . 1.407(4) yes N7 C6 . 1.505(4) yes N7 C8 . 1.522(4) yes N7 C11 . 1.489(4) yes N7 H7 . 0.91 no C1A C5A . 1.417(5) no C2A C1A . 1.418(5) no C2A C3A . 1.412(5) no C2A H2A . 0.93 no C3A C4A . 1.381(6) no C3A H3A . 0.93 no C4A C5A . 1.397(6) no C4A H4A . 0.93 no C5A H5A . 0.93 no C1B H1B . 0.93 no C2B C1B . 1.402(8) no C2B C3B . 1.377(6) no C2B H2B . 0.93 no C3B C4B . 1.352(6) no C3B H3B . 0.93 no C4B H4B . 0.93 no C5B C1B . 1.402(9) no C5B C4B . 1.353(8) no C5B H5B . 0.93 no C6 C1A . 1.488(4) yes C6 H62 . 0.97 no C6 H61 . 0.97 no C8 C9 . 1.509(4) no C8 H8 . 0.98 no C81 C8 . 1.517(5) no C81 H811 . 0.97 no C81 H812 . 0.97 no C83 O82 . 1.420(5) yes C83 H831 . 0.96 no C83 H832 . 0.96 no C83 H833 . 0.96 no C9 C10 . 1.487(5) no C9 H92 . 0.97 no C9 H91 . 0.97 no C10 C11 . 1.468(5) no C10 H102 . 0.97 no C10 H101 . 0.97 no C11 H111 . 0.97 no C11 H112 . 0.97 no