#------------------------------------------------------------------------------ #$Date: 2016-02-14 14:26:36 +0000 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/14/2101424.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_2101424 loop_ _publ_author_name 'Glidewell, C.' 'Klar, R. B.' 'Lightfoot, P.' 'Zakaria, C. M.' 'Ferguson, G.' _publ_section_title ; Hydrogen bonding in \a-ferrocenyl alcohols: structures of 1-ferrocenylethanol, 1-ferrocenyl-2-phenylethanol, 1-ferrocenyl-1-phenylpropan-1-ol, 1-ferrocenyl-1-phenyl-2-methylpropan-1-ol, 1-ferrocenyl-1-phenyl-2,2-dimethylpropan-1-ol, 1-ferrocenyl-1,2-diphenylethanol and diferrocenyl(phenyl)methanol ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 110 _journal_page_last 121 _journal_paper_doi 10.1107/S0108768195007531 _journal_volume 52 _journal_year 1996 _chemical_formula_moiety 'C19 H20 Fe O ' _chemical_formula_sum 'C19 H20 Fe O' _chemical_formula_weight 320.22 _chemical_name_common 1-Ferrocenyl-1-phenylpropan-1-ol _chemical_name_systematic ; 1-Ferrocenyl-1-phenylpropan-1-ol ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90.0 _cell_angle_beta 100.190(9) _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 10.2443(13) _cell_length_b 10.5811(17) _cell_length_c 14.2487(12) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 16.00 _cell_measurement_theta_min 10.00 _cell_volume 1520.1(3) _computing_cell_refinement 'Enraf-Nonius SET4 and CELDIM' _computing_data_collection 'Enraf-Nonius CAD4 (Enraf-Nonius 1992)' _computing_data_reduction 'DATRD2 in NRCVAX94 (Gabe, Le Page, Charland, Lee & White, 1989)' _computing_molecular_graphics 'NRCVAX94, PLATON (Spek, 1994a) and PLUTON (Spek 1994b)' _computing_publication_material 'NRCVAX94 and WordPerfect' _computing_structure_refinement NRCVAX94 _computing_structure_solution 'NRCVAX94 and Patterson Heavy-atom Method' _diffrn_ambient_temperature 294.0(10) _diffrn_measurement_device 'Nonius CAD-4 ' _diffrn_measurement_method '\q/2\q ' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Molybdenum K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3485 _diffrn_reflns_theta_max 26.92 _diffrn_reflns_theta_min 2.0 _diffrn_standards_decay_% 1.0 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.99 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_correction_T_min 0.7291 _exptl_absorpt_correction_type 'empirical \y-scans' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.399 _exptl_crystal_description plate _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.23 _refine_diff_density_min -0.22 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.14 _refine_ls_hydrogen_treatment 'C-H riding 0.95\%A, O-H refall' _refine_ls_matrix_type atomblock _refine_ls_number_parameters 194 _refine_ls_number_reflns 2289 _refine_ls_R_factor_all 0.056 _refine_ls_R_factor_obs 0.029 _refine_ls_shift/esd_max 0.000 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0008F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.047 _refine_ls_wR_factor_obs 0.042 _reflns_number_observed 2289 _reflns_number_total 3309 _reflns_observed_criterion 'Inet > 3.0\s(Inet)' _cod_data_source_file ab0340.cif _cod_data_source_block 2b _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 '1/[\s^2^(F) + 0.0008F^2^]' 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^(F) + 0.0008F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_original_formula_sum 'C19 H20 Fe O ' _cod_database_code 2101424 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,1/2+y,1/2-z x,1/2-y,1/2+z 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 _atom_site_aniso_type_symbol Fe1 0.03274(18) 0.03937(19) 0.0465(2) 0.00595(14) 0.00473(13) 0.00257(15) Fe O1 0.0495(11) 0.0358(10) 0.0915(14) 0.0028(9) 0.0171(10) 0.0091(9) O C1 0.0361(11) 0.0339(12) 0.0472(12) 0.0028(10) 0.0087(9) 0.0036(10) C C2 0.0478(14) 0.0634(17) 0.0436(13) 0.0144(12) 0.0054(11) 0.0083(12) C C3 0.0756(19) 0.084(2) 0.0529(16) 0.0244(17) 0.0250(14) 0.0171(15) C C11 0.0329(10) 0.0360(11) 0.0432(11) 0.0066(9) 0.0046(9) 0.0040(9) C C12 0.0378(12) 0.0380(13) 0.0726(17) 0.0040(11) 0.0059(11) 0.0035(12) C C13 0.0410(13) 0.0527(16) 0.091(2) 0.0064(12) 0.0195(14) 0.0228(15) C C14 0.0505(15) 0.079(2) 0.0525(15) 0.0204(15) 0.0187(12) 0.0232(15) C C15 0.0402(13) 0.0615(17) 0.0435(12) 0.0123(11) 0.0029(10) 0.0012(11) C C21 0.0554(15) 0.0677(18) 0.0574(15) 0.0158(14) 0.0111(13) 0.0197(14) C C22 0.071(2) 0.079(2) 0.0531(16) 0.0278(17) -0.0168(14) -0.0053(14) C C23 0.0377(14) 0.067(2) 0.100(2) 0.0094(13) -0.0103(15) 0.0083(17) C C24 0.0554(16) 0.0611(18) 0.082(2) 0.0263(15) 0.0234(15) 0.0134(16) C C25 0.0670(17) 0.0422(15) 0.0693(18) 0.0103(13) 0.0116(14) 0.0059(13) C C31 0.0330(10) 0.0408(12) 0.0358(11) 0.0032(9) 0.0075(8) -0.0018(9) C C32 0.0391(12) 0.0498(15) 0.0606(15) -0.0051(11) 0.0089(11) -0.0060(12) C C33 0.0326(12) 0.083(2) 0.0623(17) -0.0024(13) -0.0019(11) -0.0186(15) C C34 0.0460(14) 0.076(2) 0.0442(13) 0.0185(14) 0.0008(11) 0.0007(13) C C35 0.0509(14) 0.0548(16) 0.0462(13) 0.0126(12) 0.0086(11) 0.0089(11) C C36 0.0365(11) 0.0450(14) 0.0448(12) 0.0031(10) 0.0054(9) 0.0030(10) C 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_type_symbol Fe1 0.34401(3) 0.12719(3) 0.15774(2) 0.03980(18) Uani Fe O1 0.0091(2) 0.05882(18) 0.17093(15) 0.0584(12) Uani O C1 0.0398(2) 0.1911(2) 0.17478(16) 0.0389(11) Uani C C2 0.0594(2) 0.2378(3) 0.27850(17) 0.0519(13) Uani C C3 -0.0603(3) 0.2192(3) 0.3255(2) 0.0690(18) Uani C C11 0.1620(2) 0.2134(2) 0.13032(16) 0.0376(10) Uani C C12 0.2645(2) 0.3042(2) 0.15779(19) 0.0499(14) Uani C C13 0.3537(3) 0.2977(3) 0.0929(2) 0.0606(17) Uani C C14 0.3074(3) 0.2049(3) 0.02481(19) 0.0595(16) Uani C C15 0.1892(2) 0.1527(3) 0.04694(17) 0.0490(13) Uani C C21 0.3476(3) -0.0076(3) 0.26097(19) 0.0600(15) Uani C C22 0.4380(3) 0.0898(3) 0.2927(2) 0.0710(17) Uani C C23 0.5306(3) 0.0962(3) 0.2302(3) 0.0710(19) Uani C C24 0.4968(3) 0.0035(3) 0.1604(2) 0.0648(17) Uani C C25 0.3838(3) -0.0611(3) 0.1797(2) 0.0596(15) Uani C C31 -0.0783(2) 0.2582(2) 0.11453(15) 0.0364(11) Uani C C32 -0.1985(2) 0.1978(2) 0.08412(19) 0.0498(13) Uani C C33 -0.3035(2) 0.2637(3) 0.03083(19) 0.0604(16) Uani C C34 -0.2912(3) 0.3886(3) 0.00825(18) 0.0563(15) Uani C C35 -0.1738(3) 0.4489(3) 0.03848(17) 0.0506(13) Uani C C36 -0.0672(2) 0.3848(2) 0.09140(16) 0.0423(11) Uani C H0 0.076(3) 0.020(3) 0.179(2) 0.079(11) Uiso H H12 0.272 0.360 0.211 0.0595 Uiso H H13 0.431 0.347 0.095 0.0716 Uiso H H14 0.348 0.181 -0.027 0.0707 Uiso H H15 0.137 0.088 0.012 0.0584 Uiso H H21 0.275 -0.033 0.290 0.0702 Uiso H H22 0.437 0.142 0.347 0.0776 Uiso H H23 0.603 0.153 0.235 0.0783 Uiso H H24 0.542 -0.013 0.109 0.0762 Uiso H H25 0.340 -0.129 0.144 0.0695 Uiso H H32 -0.209 0.112 0.100 0.0598 Uiso H H33 -0.385 0.221 0.010 0.0691 Uiso H H34 -0.364 0.433 -0.028 0.0654 Uiso H H35 -0.165 0.536 0.023 0.0606 Uiso H H36 0.014 0.428 0.112 0.0521 Uiso H H2a 0.080 0.325 0.279 0.0616 Uiso H H2b 0.132 0.193 0.314 0.0616 Uiso H H3a -0.041 0.250 0.389 0.0807 Uiso H H3b -0.134 0.264 0.291 0.0807 Uiso H H3c -0.081 0.132 0.326 0.0807 Uiso H loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.002 0.002 'International Tables Vol. IV Table 2.2B' H 0.000 0.000 'International Tables Vol. IV Table 2.2B' Fe 0.301 0.845 'International Tables Vol. IV Table 2.2B' O 0.008 0.006 'International Tables Vol. IV Table 2.2B' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 5 0 -2 1 0 -8 4 4 4 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C11 Fe1 C12 40.76(9) C11 Fe1 C13 68.59(9) C11 Fe1 C14 68.40(9) C11 Fe1 C15 40.58(9) C11 Fe1 C21 110.34(10) C11 Fe1 C22 122.00(12) C11 Fe1 C23 155.58(12) C11 Fe1 C24 163.75(12) C11 Fe1 C25 127.75(11) C12 Fe1 C13 40.48(11) C12 Fe1 C14 67.82(12) C12 Fe1 C15 67.98(10) C12 Fe1 C21 126.58(11) C12 Fe1 C22 107.50(12) C12 Fe1 C23 119.16(12) C12 Fe1 C24 153.52(12) C12 Fe1 C25 164.00(11) C13 Fe1 C14 40.27(14) C13 Fe1 C15 68.11(12) C13 Fe1 C21 161.41(13) C13 Fe1 C22 123.28(14) C13 Fe1 C23 104.87(12) C13 Fe1 C24 118.61(11) C13 Fe1 C25 155.12(12) C14 Fe1 C15 40.58(11) C14 Fe1 C21 157.99(13) C14 Fe1 C22 159.53(15) C14 Fe1 C23 122.64(13) C14 Fe1 C24 106.91(11) C14 Fe1 C25 122.27(13) C15 Fe1 C21 124.00(12) C15 Fe1 C22 158.14(13) C15 Fe1 C23 160.66(13) C15 Fe1 C24 125.93(12) C15 Fe1 C25 110.61(12) C21 Fe1 C22 40.35(14) C21 Fe1 C23 68.04(13) C21 Fe1 C24 67.81(11) C21 Fe1 C25 39.92(12) C22 Fe1 C23 40.67(16) C22 Fe1 C24 67.86(13) C22 Fe1 C25 67.50(13) C23 Fe1 C24 40.17(14) C23 Fe1 C25 67.74(13) C24 Fe1 C25 40.50(13) C1 O1 H0 108(3) O1 C1 C2 109.94(19) O1 C1 C11 109.12(18) O1 C1 C31 106.58(18) C2 C1 C11 111.95(19) C2 C1 C31 110.29(18) C11 C1 C31 108.81(17) C1 C2 C3 113.9(2) Fe1 C11 C1 129.83(15) Fe1 C11 C12 69.32(13) Fe1 C11 C15 69.62(12) C1 C11 C12 127.7(2) C1 C11 C15 125.2(2) C12 C11 C15 106.9(2) Fe1 C12 C11 69.92(13) Fe1 C12 C13 69.55(15) C11 C12 C13 108.6(2) Fe1 C13 C12 69.97(14) Fe1 C13 C14 69.90(16) C12 C13 C14 108.0(2) Fe1 C14 C13 69.83(16) Fe1 C14 C15 70.10(14) C13 C14 C15 108.5(2) Fe1 C15 C11 69.80(13) Fe1 C15 C14 69.32(14) C11 C15 C14 108.1(2) Fe1 C21 C22 69.34(17) Fe1 C21 C25 70.12(16) C22 C21 C25 107.9(3) Fe1 C22 C21 70.31(15) Fe1 C22 C23 69.65(17) C21 C22 C23 108.1(3) Fe1 C23 C22 69.68(16) Fe1 C23 C24 70.05(16) C22 C23 C24 107.8(3) Fe1 C24 C23 69.78(16) Fe1 C24 C25 70.18(16) C23 C24 C25 108.0(3) Fe1 C25 C21 69.97(16) Fe1 C25 C24 69.32(16) C21 C25 C24 108.2(3) C1 C31 C32 122.1(2) C1 C31 C36 119.42(19) C32 C31 C36 118.4(2) C31 C32 C33 119.9(2) C32 C33 C34 121.2(2) C33 C34 C35 119.3(2) C34 C35 C36 120.5(2) C31 C36 C35 120.7(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Fe1 C11 2.051(2) Fe1 C12 2.043(2) Fe1 C13 2.037(3) Fe1 C14 2.038(3) Fe1 C15 2.048(2) Fe1 C21 2.045(3) Fe1 C22 2.032(3) Fe1 C23 2.032(3) Fe1 C24 2.035(3) Fe1 C25 2.047(3) O1 C1 1.433(3) O1 H0 0.79(3) C1 C2 1.537(3) C1 C11 1.518(3) C1 C31 1.529(3) C2 C3 1.510(4) C11 C12 1.425(3) C11 C15 1.421(3) C12 C13 1.411(4) C13 C14 1.403(5) C14 C15 1.417(4) C21 C22 1.406(5) C21 C25 1.397(4) C22 C23 1.412(5) C23 C24 1.397(5) C24 C25 1.413(4) C31 C32 1.387(3) C31 C36 1.390(3) C32 C33 1.390(4) C33 C34 1.371(5) C34 C35 1.363(4) C35 C36 1.389(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 H0 O1 C1 C11 36(4) no H0 O1 C1 C31 154(4) no O1 C1 C2 C3 -59.3(3) no C11 C1 C2 C3 179.2(5) no C31 C1 C2 C3 57.9(3) no O1 C1 C11 C12 -145.2(4) no O1 C1 C11 C15 40.3(3) no C2 C1 C11 C12 -23.3(2) no C2 C1 C11 C15 162.3(5) no C31 C1 C11 C12 98.9(4) no C31 C1 C11 C15 -75.6(3) no O1 C1 C31 C32 13.1(2) no O1 C1 C31 C36 -168.8(5) no C2 C1 C31 C32 -106.2(4) no C2 C1 C31 C36 71.9(3) no C11 C1 C31 C32 130.6(4) no C11 C1 C31 C36 -51.3(3) no C1 C11 C12 C13 -176.0(5) no C15 C11 C12 C13 -0.8(3) no C1 C11 C15 C14 176.1(5) no C12 C11 C15 C14 0.6(3) no C11 C12 C13 C14 0.6(2) no C12 C13 C14 C15 -0.2(2) no C13 C14 C15 C11 -0.3(2) no C25 C21 C22 C23 0.1(3) no C22 C21 C25 C24 -0.3(3) no C21 C22 C23 C24 0.2(3) no C22 C23 C24 C25 -0.4(3) no C23 C24 C25 C21 0.4(3) no C1 C31 C32 C33 178.9(5) no C36 C31 C32 C33 0.8(3) no C1 C31 C36 C35 -178.6(5) no C32 C31 C36 C35 -0.5(2) no C31 C32 C33 C34 -0.7(2) no C32 C33 C34 C35 0.2(2) no C33 C34 C35 C36 0.2(3) no C34 C35 C36 C31 0.0(2) no