#------------------------------------------------------------------------------ #$Date: 2012-02-03 18:16:24 +0100 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/64/2006495.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_2006495 loop_ _publ_author_name 'Fitzgerald, Lawrence J.' 'Gerkin, Roger E.' _publ_section_title ; Phenanthrene-9-carboxylic Acid ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1265 _journal_page_last 1267 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C15 H10 O2 ' _chemical_formula_sum 'C15 H10 O2' _chemical_formula_weight 222.24 _chemical_name_common 'phenanthrene-9-carboxylic acid' _chemical_name_systematic ' phenanthrene-9-carboxylic acid' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _cell_angle_alpha 90 _cell_angle_beta 113.308(6) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 19.824(2) _cell_length_b 5.373(2) _cell_length_c 21.6380(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 14.8 _cell_measurement_theta_min 14.4 _cell_volume 2116.7(8) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1989)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 296 _diffrn_measurement_device_type AFC5S _diffrn_measurement_method '\w scans ' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.015 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 2766 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.0 _diffrn_standards_decay_% '+-3.0 (average maximum relative intensity)' _diffrn_standards_interval_count 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'cut plate' _exptl_crystal_F_000 928 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.18 _refine_diff_density_min -0.18 _refine_ls_extinction_coef 5.8e-7(8) _refine_ls_extinction_method 'Zachariasen (1963, 1968)' _refine_ls_goodness_of_fit_ref 1.64 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 1680 _refine_ls_R_factor_gt 0.044 _refine_ls_shift/su_max '< 0.01' _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme w=\s~F~^-2^ _refine_ls_wR_factor_ref 0.048 _reflns_number_gt 1680 _reflns_number_total 2684 _reflns_threshold_expression I>1\s(I) _[local]_cod_data_source_file fr1046.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M 'C 2/c' _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: '_atom_site_adp_type' tag value 'Uij' was replaced with 'Uani' value 17 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana ; _cod_original_cell_volume 2116.7(7) _cod_database_code 2006495 loop_ _symmetry_equiv_pos_as_xyz x,y,z '-x, y, 1/2 -z' -x,-y,-z 'x, -y, 1/2 +z' '1/2+x, 1/2+y,1/2 +z' '1/2 -x, 1/2 +y, 1/2 -z' '1/2 -x, 1/2 -y, -z' '1/2 +x, 1/2 -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_calc_attached_atom O1 .41170(7) .1160(3) .49525(7) .0526(4) Uani ? ? O2 .48902(6) .2440(2) .45120(6) .0488(4) Uani ? ? C1 .19226(10) .6311(4) .42153(10) .0520(6) Uani ? ? C2 .13755(10) .8037(4) .39523(11) .0577(6) Uani ? ? C3 .14394(11) .9861(4) .35246(11) .0564(6) Uani ? ? C4 .20358(10) .9953(4) .33567(10) .0477(6) Uani ? ? C5 .33434(10) .9989(3) .30200(9) .0423(5) Uani ? ? C6 .39539(11) 1.0054(4) .28736(9) .0506(6) Uani ? ? C7 .45107(11) .8317(4) .31690(10) .0523(6) Uani ? ? C8 .44488(10) .6548(3) .35964(9) .0453(5) Uani ? ? C9 .37388(8) .4598(3) .42177(8) .0345(4) Uani ? ? C10 .31234(9) .4615(3) .43473(9) .0401(5) Uani ? ? C11 .25449(9) .6375(3) .40568(8) .0389(5) Uani ? ? C12 .26105(9) .8198(3) .36188(8) .0359(4) Uani ? ? C13 .32592(9) .8212(3) .34609(8) .0343(4) Uani ? ? C14 .38270(8) .6422(3) .37597(8) .0338(4) Uani ? ? C15 .43040(9) .2674(3) .45652(8) .0359(4) Uani ? ? H4 .2063(11) 1.124(4) .3042(10) .058(6) Uiso ? ? H5 .2954(9) 1.128(3) .2808(9) .046(5) Uiso ? ? H .4526(12) -.011(5) .5166(11) .093(8) Uiso ? ? H1 .1880 .5017 .4517 .0626 Uiso calc C1 H2 .0944 .7987 .4065 .0693 Uiso calc C2 H3 .1050 1.1107 .3339 .0679 Uiso calc C3 H6 .3999 1.1310 .2564 .0606 Uiso calc C6 H7 .4951 .8366 .3069 .0628 Uiso calc C7 H8 .4846 .5334 .3795 .0544 Uiso calc C8 H10 .3074 .3360 .4655 .0483 Uiso calc C10 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 O1 .0453(7) .0542(8) .0640(9) .0192(7) .0276(7) .0265(7) O2 .0398(7) .0506(8) .0610(8) .0182(6) .0251(6) .0185(7) C1 .0450(10) .0580(10) .0610(10) .0119(10) .0279(10) .0110(10) C2 .0420(10) .0690(10) .0690(10) .0150(10) .0290(10) .0030(10) C3 .0430(10) .0570(10) .0670(10) .0220(10) .0189(10) .0060(10) C4 .0420(10) .0440(10) .0520(10) .0123(9) .0136(9) .0057(10) C5 .0450(10) .0400(10) .0397(10) .0088(9) .0139(8) .0067(8) C6 .0610(10) .0470(10) .0470(10) .0056(10) .0244(10) .0131(9) C7 .0500(10) .0590(10) .0590(10) .0100(10) .0330(10) .0140(10) C8 .0430(10) .0480(10) .0490(10) .0124(9) .0227(8) .0095(9) C9 .0328(8) .0340(9) .0349(9) .0066(7) .0115(7) .0007(7) C10 .0400(9) .0396(10) .0426(10) .0077(8) .0182(8) .0082(8) C11 .0361(9) .0399(10) .0403(9) .0072(8) .0147(8) .0004(8) C12 .0336(9) .0338(9) .0355(9) .0050(7) .0085(7) -.0040(7) C13 .0355(9) .0325(9) .0314(8) .0032(7) .0095(7) -.0018(7) C14 .0351(9) .0332(9) .0324(8) .0040(7) .0125(7) -.0010(7) C15 .0370(9) .0344(9) .0345(9) .0057(7) .0122(7) .0014(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C15 ? ? 1.322(2) yes O1 H ? ? 1.02(2) no O2 C15 ? ? 1.219(2) yes C1 C2 ? ? 1.368(3) no C1 C11 ? ? 1.406(2) no C1 H1 ? ? .9799 no C2 C3 ? ? 1.388(3) no C2 H2 ? ? .9796 no C3 C4 ? ? 1.368(3) no C3 H3 ? ? .9803 no C4 C12 ? ? 1.413(2) no C4 H4 ? ? .99(2) no C5 C6 ? ? 1.367(2) no C5 C13 ? ? 1.406(2) no C5 H5 ? ? 1.00(2) no C6 C7 ? ? 1.393(3) no C6 H6 ? ? .9803 no C7 C8 ? ? 1.365(2) no C7 H7 ? ? .9795 no C8 C14 ? ? 1.412(2) no C8 H8 ? ? .9801 no C9 C10 ? ? 1.355(2) no C9 C14 ? ? 1.453(2) no C9 C15 ? ? 1.491(2) yes C10 C11 ? ? 1.426(2) no C10 H10 ? ? .9799 no C11 C12 ? ? 1.405(2) no C12 C13 ? ? 1.456(2) no C13 C14 ? ? 1.426(2) no H4 H5 ? ? 2.02(2) no loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 'Stewart, Davidson and Simpson (1965)' C .002 .002 'Cromer and Waber (1974)' O .008 .006 'Cromer and Waber (1974)' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 0 -4 1 1 4 2 0 -2 0 0 -14 6 0 10 6 2 -13 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 C1 C11 120.6(2) no C1 C2 C3 119.4(2) no C2 C3 C4 121.2(2) no C3 C4 C12 120.9(2) no C3 C4 H4 119.0(10) no C12 C4 H4 119.0(10) no C6 C5 C13 121.9(2) no C6 C5 H5 117.0(10) no C13 C5 H5 120.0(10) no C5 C6 C7 119.3(2) no C6 C7 C8 120.7(2) no C7 C8 C14 121.6(2) no C10 C9 C14 119.80(10) no C10 C9 C15 117.3(2) yes C14 C9 C15 122.80(10) yes C9 C10 C11 123.1(2) no C1 C11 C10 120.5(2) no C1 C11 C12 120.5(2) no C10 C11 C12 119.1(2) no C4 C12 C11 117.4(2) no C4 C12 C13 123.3(2) no C11 C12 C13 119.30(10) no C5 C13 C12 121.1(2) no C5 C13 C14 118.8(2) no C12 C13 C14 120.1(2) no C8 C14 C9 123.70(10) no C8 C14 C13 117.7(2) no C9 C14 C13 118.50(10) no C9 C15 O1 113.80(10) yes C9 C15 O2 125.3(2) yes C15 O1 H 109.0(10) yes O1 C15 O2 120.90(10) yes 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 O1 H O2 3_656 1.02(2) 1.66(3) 2.675(2) 173(2) yes