#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/25/2012582.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_2012582 loop_ _publ_author_name 'Aller, Cristina' 'Castro, Jes\'us' 'P\'erez-Lourido, Paulo' 'Labisbal, Elena' 'Garc\'ia-V\'azquez, Jos\'e Arturo' _publ_section_title Aquachloro(1,10-phenanthroline-\k^2^N,N')(p-toluenesulfonato-\kO)copper(II) _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first m155 _journal_page_last m157 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac '[Cu Cl (C7 H7 O3 S) (C12 H8 N2) (H2 O)]' _chemical_formula_moiety 'C19 H17 Cl Cu N2 O4 S' _chemical_formula_sum 'C19 H17 Cl Cu N2 O4 S' _chemical_formula_weight 468.40 _chemical_name_systematic ; aquochloro(1,10-phenanthroline-N,N')(4-methylphenylsulfonate-O)copper(II) ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 83.773(2) _cell_angle_beta 78.629(2) _cell_angle_gamma 77.153(2) _cell_formula_units_Z 2 _cell_length_a 7.0887(7) _cell_length_b 9.9723(9) _cell_length_c 14.4170(13) _cell_measurement_reflns_used 3380 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.76 _cell_measurement_theta_min 2.47 _cell_volume 971.90(16) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1998)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .948 _diffrn_measured_fraction_theta_max .948 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0359 _diffrn_reflns_av_sigmaI/netI .0357 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 5013 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.10 _exptl_absorpt_coefficient_mu 1.397 _exptl_absorpt_correction_T_max .778 _exptl_absorpt_correction_T_min .506 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Siemens, 1996)' _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 478 _exptl_crystal_size_max .55 _exptl_crystal_size_mid .36 _exptl_crystal_size_min .18 _refine_diff_density_max 1.094 _refine_diff_density_min -.802 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 3249 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all .0509 _refine_ls_R_factor_gt .0468 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0943P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .1227 _refine_ls_wR_factor_ref .1259 _reflns_number_gt 2858 _reflns_number_total 3249 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file jz1489.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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 ; _cod_database_code 2012582 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cu .20979(6) .77450(4) .84191(3) .03153(17) Uani d . 1 . . Cu Cl .10985(17) .57819(9) .84060(8) .0571(3) Uani d . 1 . . Cl O1W .1351(4) .8465(3) .71753(18) .0388(6) Uani d D 1 . . O H1 .238(5) .829(5) .682(3) .082(18) Uiso d D 1 . . H H2 .044(5) .819(5) .709(3) .075(16) Uiso d D 1 . . H O2 .5005(4) .8066(3) .61529(17) .0446(6) Uani d . 1 . . O O3 .5350(3) .7226(2) .77580(16) .0390(6) Uani d . 1 . . O O1 .8077(4) .7975(3) .6680(2) .0516(7) Uani d . 1 . . O S1 .63699(12) .73579(8) .67733(6) .0343(2) Uani d . 1 . . S C11 .7225(5) .5667(4) .6395(2) .0402(8) Uani d . 1 . . C C12 .9144(6) .5009(4) .6355(3) .0554(10) Uani d . 1 . . C H12 1.0045 .5454 .6515 .066 Uiso calc R 1 . . H C13 .9736(8) .3667(5) .6071(3) .0698(14) Uani d . 1 . . C H13 1.1042 .3218 .6046 .084 Uiso calc R 1 . . H C14 .8424(9) .2990(5) .5827(3) .0677(14) Uani d . 1 . . C C15 .6507(8) .3672(5) .5867(3) .0702(13) Uani d . 1 . . C H15 .5612 .3232 .5696 .084 Uiso calc R 1 . . H C16 .5878(7) .4992(4) .6155(3) .0566(11) Uani d . 1 . . C H16 .4566 .5433 .6190 .068 Uiso calc R 1 . . H C17 .9096(11) .1523(5) .5542(4) .102(2) Uani d . 1 . . C H17A .8252 .1341 .5146 .153 Uiso calc R 1 . . H H17B .9042 .0901 .6099 .153 Uiso calc R 1 . . H H17C 1.0422 .1393 .5198 .153 Uiso calc R 1 . . H N21 .2159(4) .9688(3) .86886(19) .0310(6) Uani d . 1 . . N N22 .2595(4) .7371(3) .97547(19) .0310(6) Uani d . 1 . . N C21 .1970(5) 1.0840(3) .8123(3) .0403(8) Uani d . 1 . . C H21 .1836 1.0791 .7499 .048 Uiso calc R 1 . . H C22 .1964(5) 1.2117(3) .8433(3) .0447(9) Uani d . 1 . . C H22 .1840 1.2900 .8018 .054 Uiso calc R 1 . . H C23 .2143(5) 1.2217(3) .9352(3) .0445(9) Uani d . 1 . . C H23 .2097 1.3072 .9567 .053 Uiso calc R 1 . . H C24 .2393(5) 1.1029(3) .9965(3) .0373(8) Uani d . 1 . . C C25 .2396(5) .9785(3) .9583(2) .0308(7) Uani d . 1 . . C C26 .2646(4) .8516(3) 1.0169(2) .0309(7) Uani d . 1 . . C C27 .2920(5) .8527(4) 1.1103(2) .0378(8) Uani d . 1 . . C C28 .3201(5) .7218(4) 1.1615(2) .0491(10) Uani d . 1 . . C H28 .3407 .7149 1.2237 .059 Uiso calc R 1 . . H C29 .3169(6) .6069(4) 1.1197(3) .0496(9) Uani d . 1 . . C H29 .3373 .5211 1.1529 .060 Uiso calc R 1 . . H C210 .2833(5) .6179(4) 1.0276(3) .0407(8) Uani d . 1 . . C H210 .2769 .5386 1.0009 .049 Uiso calc R 1 . . H C211 .2912(5) .9792(4) 1.1465(3) .0453(9) Uani d . 1 . . C H211 .3076 .9800 1.2088 .054 Uiso calc R 1 . . H C212 .2672(5) 1.0995(4) 1.0921(3) .0465(9) Uani d . 1 . . C H212 .2689 1.1809 1.1175 .056 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 Cu .0400(3) .0215(2) .0344(3) -.00610(17) -.00978(18) -.00269(16) Cl .0880(8) .0293(5) .0664(7) -.0232(5) -.0324(6) .0002(4) O1W .0387(15) .0390(14) .0415(14) -.0102(12) -.0122(12) -.0012(11) O2 .0453(15) .0458(15) .0419(14) -.0059(11) -.0149(11) .0067(11) O3 .0424(14) .0379(13) .0341(12) -.0002(10) -.0092(10) -.0031(10) O1 .0428(15) .0539(17) .0638(17) -.0178(13) -.0141(13) -.0036(13) S1 .0343(5) .0346(5) .0348(5) -.0058(3) -.0096(3) -.0019(3) C11 .050(2) .0381(19) .0295(17) -.0002(16) -.0082(15) -.0051(14) C12 .056(2) .055(2) .049(2) .0030(19) -.0069(19) -.0103(19) C13 .076(3) .062(3) .052(3) .019(2) .001(2) -.009(2) C14 .112(4) .047(2) .034(2) .000(3) -.005(2) -.0076(18) C15 .103(4) .054(3) .061(3) -.016(3) -.026(3) -.013(2) C16 .071(3) .045(2) .061(3) -.009(2) -.029(2) -.0078(19) C17 .181(7) .050(3) .056(3) .005(3) .000(4) -.013(2) N21 .0337(14) .0222(13) .0364(15) -.0041(11) -.0064(11) -.0021(11) N22 .0316(14) .0244(13) .0349(14) -.0039(11) -.0035(11) -.0017(11) C21 .042(2) .0310(18) .048(2) -.0090(15) -.0082(16) .0021(15) C22 .046(2) .0242(17) .062(2) -.0061(15) -.0098(18) .0035(15) C23 .0340(19) .0253(17) .075(3) -.0082(14) -.0054(17) -.0127(17) C24 .0267(17) .0345(18) .052(2) -.0091(14) -.0011(15) -.0144(15) C25 .0288(17) .0231(15) .0398(18) -.0045(12) -.0021(13) -.0074(13) C26 .0258(16) .0320(16) .0327(17) -.0030(13) -.0034(13) -.0025(13) C27 .0282(17) .047(2) .0374(18) -.0059(14) -.0041(14) -.0083(15) C28 .047(2) .067(3) .0316(19) -.0100(19) -.0084(16) .0049(18) C29 .054(2) .045(2) .043(2) -.0037(18) -.0094(17) .0127(17) C210 .045(2) .0305(17) .043(2) -.0060(15) -.0051(16) .0024(14) C211 .040(2) .066(3) .0343(18) -.0146(18) -.0050(15) -.0169(17) C212 .037(2) .052(2) .055(2) -.0136(17) -.0003(17) -.0282(19) 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 Cu O1W . 1.984(3) y Cu N22 . 2.006(3) y Cu N21 . 2.028(3) y Cu Cl . 2.2282(9) y Cu O3 . 2.281(2) y O1W H1 . .80(2) ? O1W H2 . .792(19) ? O2 S1 . 1.461(3) y O3 S1 . 1.467(2) y O1 S1 . 1.453(3) y S1 C11 . 1.767(4) ? C11 C12 . 1.365(5) ? C11 C16 . 1.396(5) ? C12 C13 . 1.391(6) ? C12 H12 . .9300 ? C13 C14 . 1.381(8) ? C13 H13 . .9300 ? C14 C15 . 1.371(7) ? C14 C17 . 1.510(6) ? C15 C16 . 1.374(6) ? C15 H15 . .9300 ? C16 H16 . .9300 ? C17 H17A . .9600 ? C17 H17B . .9600 ? C17 H17C . .9600 ? N21 C21 . 1.332(4) ? N21 C25 . 1.349(4) ? N22 C210 . 1.331(4) ? N22 C26 . 1.355(4) ? C21 C22 . 1.393(5) ? C21 H21 . .9300 ? C22 C23 . 1.371(5) ? C22 H22 . .9300 ? C23 C24 . 1.399(5) ? C23 H23 . .9300 ? C24 C25 . 1.410(4) ? C24 C212 . 1.426(5) ? C25 C26 . 1.440(4) ? C26 C27 . 1.399(5) ? C27 C211 . 1.415(5) ? C27 C28 . 1.421(5) ? C28 C29 . 1.358(5) ? C28 H28 . .9300 ? C29 C210 . 1.384(5) ? C29 H29 . .9300 ? C210 H210 . .9300 ? C211 C212 . 1.356(6) ? C211 H211 . .9300 ? C212 H212 . .9300 ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu .3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O1W Cu N22 169.20(11) y O1W Cu N21 89.30(11) y N22 Cu N21 81.22(10) y O1W Cu Cl 93.22(8) y N22 Cu Cl 94.22(8) y N21 Cu Cl 161.91(8) y O1W Cu O3 91.81(10) y N22 Cu O3 94.03(9) y N21 Cu O3 94.19(10) y Cl Cu O3 103.62(7) y Cu O1W H1 102(4) ? Cu O1W H2 111(4) ? H1 O1W H2 120(5) ? S1 O3 Cu 131.59(14) ? O1 S1 O2 112.62(15) y O1 S1 O3 112.78(16) y O2 S1 O3 111.06(15) y O1 S1 C11 107.22(17) y O2 S1 C11 106.01(16) y O3 S1 C11 106.66(15) y C12 C11 C16 120.0(4) ? C12 C11 S1 121.5(3) ? C16 C11 S1 118.5(3) ? C11 C12 C13 119.3(4) ? C11 C12 H12 120.3 ? C13 C12 H12 120.3 ? C14 C13 C12 121.3(5) ? C14 C13 H13 119.4 ? C12 C13 H13 119.4 ? C15 C14 C13 118.4(4) ? C15 C14 C17 121.3(5) ? C13 C14 C17 120.2(5) ? C14 C15 C16 121.4(5) ? C14 C15 H15 119.3 ? C16 C15 H15 119.3 ? C15 C16 C11 119.5(4) ? C15 C16 H16 120.3 ? C11 C16 H16 120.3 ? C14 C17 H17A 109.5 ? C14 C17 H17B 109.5 ? H17A C17 H17B 109.5 ? C14 C17 H17C 109.5 ? H17A C17 H17C 109.5 ? H17B C17 H17C 109.5 ? C21 N21 C25 117.5(3) ? C21 N21 Cu 129.5(2) ? C25 N21 Cu 113.0(2) ? C210 N22 C26 117.3(3) ? C210 N22 Cu 129.0(2) ? C26 N22 Cu 113.7(2) ? N21 C21 C22 122.3(3) ? N21 C21 H21 118.9 ? C22 C21 H21 118.9 ? C23 C22 C21 119.9(3) ? C23 C22 H22 120.0 ? C21 C22 H22 120.0 ? C22 C23 C24 119.8(3) ? C22 C23 H23 120.1 ? C24 C23 H23 120.1 ? C23 C24 C25 116.1(3) ? C23 C24 C212 124.9(3) ? C25 C24 C212 119.0(3) ? N21 C25 C24 124.4(3) ? N21 C25 C26 116.2(3) ? C24 C25 C26 119.5(3) ? N22 C26 C27 124.5(3) ? N22 C26 C25 115.8(3) ? C27 C26 C25 119.7(3) ? C26 C27 C211 119.4(3) ? C26 C27 C28 115.4(3) ? C211 C27 C28 125.2(3) ? C29 C28 C27 120.1(3) ? C29 C28 H28 119.9 ? C27 C28 H28 119.9 ? C28 C29 C210 119.8(3) ? C28 C29 H29 120.1 ? C210 C29 H29 120.1 ? N22 C210 C29 122.9(3) ? N22 C210 H210 118.6 ? C29 C210 H210 118.6 ? C212 C211 C27 121.4(3) ? C212 C211 H211 119.3 ? C27 C211 H211 119.3 ? C211 C212 C24 121.0(3) ? C211 C212 H212 119.5 ? C24 C212 H212 119.5 ? 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 O1W H1 O2 . .80(2) 1.90(2) 2.684(4) 168(5) O1W H2 O1 1_455 .79(2) 1.94(2) 2.714(4) 164(5) C21 H21 O1W . .93 2.52 3.011(4) 113.0 C210 H210 Cl . .93 2.75 3.269(4) 116.1 C29 H29 O3 2_667 .93 2.58 3.491(4) 168.2 C28 H28 Cg1 2_667 .93 2.76 3.481(4) 135.5 C29 H29 Cg1 2_667 .93 3.40 3.798(4) 108.7 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 O1W Cu O3 S1 -2.1(2) N22 Cu O3 S1 -173.00(19) N21 Cu O3 S1 -91.5(2) Cl Cu O3 S1 91.66(18) Cu O3 S1 O1 133.74(19) Cu O3 S1 O2 6.2(2) Cu O3 S1 C11 -108.8(2) O1 S1 C11 C12 19.6(4) O2 S1 C11 C12 140.1(3) O3 S1 C11 C12 -101.5(3) O1 S1 C11 C16 -161.9(3) O2 S1 C11 C16 -41.4(3) O3 S1 C11 C16 77.0(3) C16 C11 C12 C13 .2(6) S1 C11 C12 C13 178.6(3) C11 C12 C13 C14 .2(7) C12 C13 C14 C15 .1(7) C12 C13 C14 C17 -178.7(4) C13 C14 C15 C16 -.9(7) C17 C14 C15 C16 177.9(4) C14 C15 C16 C11 1.3(7) C12 C11 C16 C15 -.9(6) S1 C11 C16 C15 -179.4(3) O1W Cu N21 C21 -6.7(3) N22 Cu N21 C21 178.5(3) Cl Cu N21 C21 -104.9(3) O3 Cu N21 C21 85.1(3) O1W Cu N21 C25 172.1(2) N22 Cu N21 C25 -2.7(2) Cl Cu N21 C25 73.8(4) O3 Cu N21 C25 -96.1(2) O1W Cu N22 C210 151.9(5) N21 Cu N22 C210 -179.2(3) Cl Cu N22 C210 18.5(3) O3 Cu N22 C210 -85.5(3) O1W Cu N22 C26 -26.6(7) N21 Cu N22 C26 2.4(2) Cl Cu N22 C26 -160.0(2) O3 Cu N22 C26 96.0(2) C25 N21 C21 C22 -1.5(5) Cu N21 C21 C22 177.2(2) N21 C21 C22 C23 -.5(5) C21 C22 C23 C24 2.1(5) C22 C23 C24 C25 -1.5(5) C22 C23 C24 C212 177.4(3) C21 N21 C25 C24 2.1(5) Cu N21 C25 C24 -176.8(2) C21 N21 C25 C26 -178.5(3) Cu N21 C25 C26 2.6(4) C23 C24 C25 N21 -.6(5) C212 C24 C25 N21 -179.6(3) C23 C24 C25 C26 180.0(3) C212 C24 C25 C26 1.0(5) C210 N22 C26 C27 -.3(5) Cu N22 C26 C27 178.3(2) C210 N22 C26 C25 179.7(3) Cu N22 C26 C25 -1.7(3) N21 C25 C26 N22 -.6(4) C24 C25 C26 N22 178.8(3) N21 C25 C26 C27 179.4(3) C24 C25 C26 C27 -1.2(5) N22 C26 C27 C211 -178.9(3) C25 C26 C27 C211 1.1(5) N22 C26 C27 C28 1.5(5) C25 C26 C27 C28 -178.5(3) C26 C27 C28 C29 -.8(5) C211 C27 C28 C29 179.6(3) C27 C28 C29 C210 -1.0(6) C26 N22 C210 C29 -1.6(5) Cu N22 C210 C29 -180.0(3) C28 C29 C210 N22 2.3(6) C26 C27 C211 C212 -.9(5) C28 C27 C211 C212 178.7(3) C27 C211 C212 C24 .8(5) C23 C24 C212 C211 -179.7(3) C25 C24 C212 C211 -.8(5) _cod_database_fobs_code 2012582 _journal_paper_doi 10.1107/S0108270102000458