#------------------------------------------------------------------------------ #$Date: 2011-01-02 20:00:31 +0000 (Sun, 02 Jan 2011) $ #$Revision: 5310 $ #$URL: svn://www.crystallography.net/cod/cif/2/2203276.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_2203276 loop_ _publ_author_name 'Ucar, Ibrahim' 'Yesilel, Okan Zafer' 'Bulut, Ahmet' 'Icbudak, Hasan' 'Olmez, Halis' 'Kazak, Canan' _publ_section_title ; Bis(triethanolamine-\k^3^N,O,O')copper(II) squarate ; _journal_issue 3 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first m322 _journal_page_last m324 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac '[Cu (C6 H15 N1 O3)2] (C4 O4)' _chemical_formula_moiety 'C12 H30 Cu N2 O6 2+, C4 O4 2-' _chemical_formula_sum 'C16 H30 Cu N2 O10' _chemical_formula_weight 473.97 _chemical_name_systematic ; Bis(triethanolamine-\k^3^N,O,O')copper(II) squarate ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 101.206(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 8.145(5) _cell_length_b 13.634(5) _cell_length_c 9.082(5) _cell_measurement_reflns_used 9392 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.81 _cell_measurement_theta_min 2.28 _cell_volume 989.3(9) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2001)' _computing_data_reduction 'X-RED (Stoe & Cie, 2001)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Stoe IPDS-2' _diffrn_measurement_method \f _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0660 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 3720 _diffrn_reflns_theta_full 25.90 _diffrn_reflns_theta_max 25.90 _diffrn_reflns_theta_min 2.55 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.162 _exptl_absorpt_correction_T_max 0.9280 _exptl_absorpt_correction_T_min 0.7828 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(X-RED; Stoe & Cie, 2002)' _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 498 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.241 _refine_diff_density_min -0.320 _refine_ls_extinction_coef 0.108(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.774 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 141 _refine_ls_number_reflns 1912 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 0.774 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0265 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0189P)^2^] where P = (Fo^2^ + 2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.0503 _reflns_number_gt 1256 _reflns_number_total 1912 _reflns_threshold_expression I>2\s(I) _[local]_cod_cif_authors_sg_H-M 'P 21/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 ; _cod_database_code 2203276 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' 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_type_symbol Cu1 0.0000 0.5000 0.5000 0.03181(11) Uani d S 1 Cu O1 -0.1684(2) 0.39398(11) 0.42375(19) 0.0390(4) Uani d D 1 O O2 -0.0055(2) 0.56581(12) 0.26736(19) 0.0442(4) Uani d D 1 O O3 0.5575(2) 0.30807(13) 0.6652(2) 0.0624(5) Uani d . 1 O H3 0.5799 0.2494 0.6708 0.094 Uiso calc R 1 H N1 0.1678(2) 0.40960(12) 0.4296(2) 0.0323(4) Uani d . 1 N C1 -0.0764(3) 0.30399(16) 0.4278(3) 0.0467(7) Uani d . 1 C H1A -0.1463 0.2537 0.3717 0.056 Uiso calc R 1 H H1B -0.0425 0.2818 0.5307 0.056 Uiso calc R 1 H C2 0.0752(3) 0.32117(17) 0.3601(3) 0.0445(6) Uani d . 1 C H2A 0.1478 0.2642 0.3767 0.053 Uiso calc R 1 H H2B 0.0412 0.3308 0.2526 0.053 Uiso calc R 1 H C3 0.2410(3) 0.46620(17) 0.3184(3) 0.0432(6) Uani d . 1 C H3A 0.3088 0.4226 0.2705 0.052 Uiso calc R 1 H H3B 0.3140 0.5166 0.3705 0.052 Uiso calc R 1 H C4 0.1103(3) 0.5138(2) 0.1991(3) 0.0473(7) Uani d . 1 C H4A 0.1638 0.5585 0.1399 0.057 Uiso calc R 1 H H4B 0.0521 0.4640 0.1325 0.057 Uiso calc R 1 H C5 0.3000(3) 0.38161(17) 0.5596(3) 0.0372(6) Uani d . 1 C H5A 0.2490 0.3408 0.6258 0.045 Uiso calc R 1 H H5B 0.3391 0.4409 0.6144 0.045 Uiso calc R 1 H C6 0.4503(3) 0.32793(18) 0.5259(3) 0.0458(7) Uani d . 1 C H6A 0.4160 0.2672 0.4731 0.055 Uiso calc R 1 H H6B 0.5076 0.3680 0.4635 0.055 Uiso calc R 1 H O4 0.72816(19) -0.09995(11) 0.55833(18) 0.0444(4) Uani d . 1 O O5 0.6251(2) 0.11137(12) 0.6725(2) 0.0618(6) Uani d . 1 O C7 0.6036(3) -0.04526(18) 0.5272(3) 0.0349(6) Uani d . 1 C C8 0.5570(3) 0.04978(19) 0.5773(3) 0.0384(6) Uani d . 1 C H1 -0.228(3) 0.401(2) 0.3388(16) 0.061(9) Uiso d D 1 H H2 -0.096(2) 0.572(2) 0.205(3) 0.076(10) Uiso d D 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 Cu1 0.0317(2) 0.02944(19) 0.0293(2) 0.0006(2) -0.00655(14) -0.0018(2) O1 0.0350(9) 0.0376(9) 0.0374(11) 0.0018(7) -0.0101(8) -0.0018(8) O2 0.0397(10) 0.0520(10) 0.0345(10) 0.0127(8) -0.0083(8) 0.0028(8) O3 0.0586(11) 0.0494(11) 0.0631(13) 0.0170(9) -0.0281(10) -0.0015(9) N1 0.0324(11) 0.0303(10) 0.0284(11) 0.0023(8) -0.0082(8) 0.0003(8) C1 0.0484(15) 0.0277(13) 0.0536(17) -0.0028(11) -0.0155(13) 0.0006(11) C2 0.0444(15) 0.0334(13) 0.0469(15) 0.0048(11) -0.0134(12) -0.0117(12) C3 0.0410(14) 0.0477(16) 0.0387(15) 0.0079(10) 0.0027(12) 0.0026(11) C4 0.0514(14) 0.0530(18) 0.0344(12) 0.0119(14) 0.0007(11) 0.0085(13) C5 0.0354(13) 0.0356(13) 0.0347(14) 0.0032(10) -0.0075(10) 0.0009(11) C6 0.0399(16) 0.0433(14) 0.0468(17) 0.0075(11) -0.0096(12) -0.0019(12) O4 0.0387(10) 0.0418(10) 0.0442(11) 0.0055(8) -0.0129(8) -0.0008(8) O5 0.0699(12) 0.0376(10) 0.0568(12) 0.0082(9) -0.0396(10) -0.0106(9) C7 0.0372(14) 0.0358(13) 0.0265(13) -0.0022(11) -0.0067(11) 0.0037(11) C8 0.0403(15) 0.0375(14) 0.0299(14) -0.0007(12) -0.0115(12) 0.0015(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 O1 Cu1 N1 84.93(8) yes O1 Cu1 O2 94.24(7) yes N1 Cu1 O2 80.85(7) yes C1 O1 Cu1 106.68(13) ? C1 O1 H1 109.1(19) ? Cu1 O1 H1 118.3(19) ? C4 O2 Cu1 108.24(13) ? C4 O2 H2 109(2) ? Cu1 O2 H2 121(2) ? C6 O3 H3 109.5 ? C5 N1 C3 110.47(17) ? C5 N1 C2 110.91(17) ? C3 N1 C2 111.61(19) ? C5 N1 Cu1 109.47(14) ? C3 N1 Cu1 106.39(13) ? C2 N1 Cu1 107.83(14) ? O1 C1 C2 108.85(19) ? O1 C1 H1A 109.9 ? C2 C1 H1A 109.9 ? O1 C1 H1B 109.9 ? C2 C1 H1B 109.9 ? H1A C1 H1B 108.3 ? N1 C2 C1 109.92(19) ? N1 C2 H2A 109.7 ? C1 C2 H2A 109.7 ? N1 C2 H2B 109.7 ? C1 C2 H2B 109.7 ? H2A C2 H2B 108.2 ? N1 C3 C4 113.02(19) ? N1 C3 H3A 109.0 ? C4 C3 H3A 109.0 ? N1 C3 H3B 109.0 ? C4 C3 H3B 109.0 ? H3A C3 H3B 107.8 ? O2 C4 C3 109.75(19) ? O2 C4 H4A 109.7 ? C3 C4 H4A 109.7 ? O2 C4 H4B 109.7 ? C3 C4 H4B 109.7 ? H4A C4 H4B 108.2 ? N1 C5 C6 117.09(19) ? N1 C5 H5A 108.0 ? C6 C5 H5A 108.0 ? N1 C5 H5B 108.0 ? C6 C5 H5B 108.0 ? H5A C5 H5B 107.3 ? O3 C6 C5 107.20(19) ? O3 C6 H6A 110.3 ? C5 C6 H6A 110.3 ? O3 C6 H6B 110.3 ? C5 C6 H6B 110.3 ? H6A C6 H6B 108.5 ? O4 C7 C8 135.7(2) yes O5 C8 C7 135.0(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cu1 O1 2.0199(17) yes Cu1 N1 2.0340(18) yes Cu1 O2 2.288(2) yes O1 C1 1.434(3) yes O1 H1 0.835(10) ? O2 C4 1.416(3) yes O2 H2 0.841(10) ? O3 C6 1.416(3) yes O3 H3 0.82 ? N1 C5 1.484(3) yes N1 C3 1.485(3) yes N1 C2 1.496(3) yes C1 C2 1.501(3) ? C1 H1A 0.97 ? C1 H1B 0.97 ? C2 H2A 0.97 ? C2 H2B 0.97 ? C3 C4 1.510(3) ? C3 H3A 0.97 ? C3 H3B 0.97 ? C4 H4A 0.97 ? C4 H4B 0.97 ? C5 C6 1.508(3) ? C5 H5A 0.97 ? C5 H5B 0.97 ? C6 H6A 0.97 ? C6 H6B 0.97 ? O4 C7 1.246(3) yes O5 C8 1.255(3) yes C7 C8 1.448(3) 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 O1 H1 O5 4_465 0.840(10) 1.740(10) 2.559(2) 166(3) O2 H2 O4 4_465 0.840(10) 1.800(10) 2.632(2) 171(3) O3 H3 O5 . 0.82 1.92 2.736(3) 177 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 N1 Cu1 O1 C1 25.03(15) O2 Cu1 O1 C1 105.44(15) O1 Cu1 O2 C4 -86.01(16) N1 Cu1 O2 C4 -1.85(15) O1 Cu1 N1 C5 -119.12(14) O2 Cu1 N1 C5 145.75(14) O1 Cu1 N1 C3 121.49(14) O2 Cu1 N1 C3 26.36(13) O1 Cu1 N1 C2 1.63(14) O2 Cu1 N1 C2 -93.50(15) Cu1 O1 C1 C2 -46.7(2) C5 N1 C2 C1 92.6(2) C3 N1 C2 C1 -143.79(19) Cu1 N1 C2 C1 -27.3(2) O1 C1 C2 N1 50.1(2) C5 N1 C3 C4 -168.6(2) C2 N1 C3 C4 67.5(2) Cu1 N1 C3 C4 -49.9(2) Cu1 O2 C4 C3 -23.2(2) N1 C3 C4 O2 49.8(3) C3 N1 C5 C6 -53.7(2) C2 N1 C5 C6 70.6(3) Cu1 N1 C5 C6 -170.52(16) N1 C5 C6 O3 -179.39(18) O4 C7 C8 O5 -1.0(5)