#------------------------------------------------------------------------------ #$Date: 2014-07-12 07:06:18 +0300 (Sat, 12 Jul 2014) $ #$Revision: 120112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/11/7201172.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7201172 loop_ _publ_author_name 'Balasubramanian, Vimalkumar' 'Ezhevskaya, Maria' 'Moons, Hans' 'Neuburger, Markus' 'Cristescu, Carol' 'Van Doorslaer, Sabine' 'Palivan, Cornelia' _publ_section_title ; Structural characterization of a highly active superoxide-dismutase mimic ; _journal_issue 31 _journal_name_full 'Physical Chemistry Chemical Physics' _journal_page_first 6778 _journal_page_last 6787 _journal_volume 11 _journal_year 2009 _chemical_formula_moiety 'C20 H16 Cl2 Cu2 N10 O6, 4(C2 H6 O S)' _chemical_formula_sum 'C28 H40 Cl2 Cu2 N10 O10 S4' _chemical_formula_weight 1002.95 _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 _audit_creation_date 09-02-10 _audit_creation_method CRYSTALS_ver_12.86 _cell_angle_alpha 111.339(2) _cell_angle_beta 97.147(2) _cell_angle_gamma 99.073(2) _cell_formula_units_Z 1 _cell_length_a 8.2044(5) _cell_length_b 10.5939(6) _cell_length_c 12.6014(7) _cell_measurement_reflns_used 1516 _cell_measurement_temperature 123 _cell_measurement_theta_max 26 _cell_measurement_theta_min 4 _cell_volume 987.54(10) _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 123 _diffrn_measured_fraction_theta_full 0.961 _diffrn_measured_fraction_theta_max 0.959 _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_measurement_method '\f & \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 6570 _diffrn_reflns_theta_full 25.001 _diffrn_reflns_theta_max 26.597 _diffrn_reflns_theta_min 2.163 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.490 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.686 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 514 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.77 _refine_diff_density_min -0.47 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.1069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 2607 _refine_ls_number_restraints 59 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0421 _refine_ls_shift/su_max 0.000269 _refine_ls_structure_factor_coef F _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.262 0.108 0.139 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0623 _refine_ls_wR_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0365 _reflns_limit_h_max 10 _reflns_limit_h_min -10 _reflns_limit_k_max 12 _reflns_limit_k_min -13 _reflns_limit_l_max 15 _reflns_limit_l_min 0 _reflns_number_gt 2725 _reflns_number_total 3974 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 1.31 _oxford_diffrn_Wilson_scale 55.47 _oxford_refine_ls_r_factor_ref 0.0387 _oxford_refine_ls_scale 0.1365(2) _oxford_reflns_number_all 3950 _oxford_reflns_threshold_expression_ref I>2.5\s(I) _[local]_cod_data_source_file b905593b.txt _[local]_cod_data_source_block cul1_123k _[local]_cod_cif_authors_sg_H-M 'P -1 ' _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 ; _cod_database_code 7201172 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cu1 Cu 0.69298(6) 0.45585(5) 0.48457(4) 0.0156 1.0000 Uani . . . . . . . Cl1 Cl 0.60580(11) 0.65523(9) 0.49221(8) 0.0175 1.0000 Uani . . . . . . . S1 S 0.43496(14) 0.16161(12) -0.22550(9) 0.0291 1.0000 Uani D . . . . . . S2 S 1.10638(13) -0.02127(11) 0.24537(9) 0.0241 1.0000 Uani D . . . . . . O1 O 0.7730(3) 0.5233(3) 0.6476(2) 0.0188 1.0000 Uani . . . . . . . O2 O 0.7733(3) 0.1048(3) 0.0978(2) 0.0228 1.0000 Uani . . . . . . . O3 O 0.3692(3) 0.3414(3) 0.0568(2) 0.0260 1.0000 Uani . . . . . . . O4 O 0.5215(4) 0.0901(3) -0.1581(3) 0.0334 1.0000 Uani . . . . . . . O5 O 0.9792(4) 0.0352(3) 0.3169(2) 0.0259 1.0000 Uani . . . . . . . N1 N 0.8464(4) 0.3277(3) 0.4535(3) 0.0160 1.0000 Uani D . . . . . . N2 N 0.8299(4) 0.2459(3) 0.3366(3) 0.0180 1.0000 Uani D . . . . . . N3 N 0.5659(4) 0.2173(3) 0.0764(3) 0.0199 1.0000 Uani D . . . . . . N4 N 0.5036(4) 0.3817(3) 0.2381(3) 0.0181 1.0000 Uani D . . . . . . N5 N 0.6220(4) 0.3571(3) 0.3120(3) 0.0163 1.0000 Uani D . . . . . . C1 C 0.9001(4) 0.4948(4) 0.7028(3) 0.0161 1.0000 Uani D . . . . . . C2 C 0.9488(4) 0.5683(4) 0.8249(3) 0.0162 1.0000 Uani D . . . . . . C3 C 1.0773(4) 0.5423(3) 0.8894(3) 0.0172 1.0000 Uani D . . . . . . C4 C 1.1658(4) 0.4416(4) 0.8368(3) 0.0190 1.0000 Uani D . . . . . . C5 C 1.1217(4) 0.3679(4) 0.7184(3) 0.0212 1.0000 Uani D . . . . . . C6 C 0.9904(4) 0.3925(4) 0.6496(3) 0.0160 1.0000 Uani D . . . . . . C7 C 0.9588(4) 0.3130(4) 0.5269(3) 0.0163 1.0000 Uani D . . . . . . C8 C 0.7095(5) 0.2665(4) 0.2666(3) 0.0170 1.0000 Uani D . . . . . . C9 C 0.6879(4) 0.1857(4) 0.1390(3) 0.0166 1.0000 Uani D . . . . . . C10 C 0.4719(5) 0.3169(4) 0.1207(3) 0.0196 1.0000 Uani D . . . . . . C11 C 0.5938(7) 0.3001(6) -0.2175(5) 0.0474 1.0000 Uani D . . . . . . C12 C 0.4176(7) 0.0567(6) -0.3713(4) 0.0403 1.0000 Uani D . . . . . . C13 C 0.9889(6) -0.1351(4) 0.1049(4) 0.0299 1.0000 Uani D . . . . . . C14 C 1.1997(5) 0.1130(5) 0.2051(4) 0.0269 1.0000 Uani D . . . . . . H2 H 0.8782 0.1759 0.3137 0.0244 1.0000 Uiso DR . . . . . . H3 H 0.5476 0.1737 0.0008 0.0214 1.0000 Uiso DR . . . . . . H4 H 0.4328 0.4284 0.2693 0.0212 1.0000 Uiso DR . . . . . . H21 H 0.8918 0.6362 0.8621 0.0194 1.0000 Uiso DR . . . . . . H31 H 1.1060 0.5931 0.9703 0.0194 1.0000 Uiso DR . . . . . . H41 H 1.2538 0.4254 0.8810 0.0243 1.0000 Uiso DR . . . . . . H51 H 1.1792 0.2975 0.6817 0.0259 1.0000 Uiso DR . . . . . . H71 H 1.0228 0.2459 0.4976 0.0205 1.0000 Uiso DR . . . . . . H111 H 0.6913 0.2638 -0.2376 0.0691 1.0000 Uiso DR . . . . . . H112 H 0.5507 0.3371 -0.2724 0.0691 1.0000 Uiso DR . . . . . . H113 H 0.6182 0.3701 -0.1396 0.0691 1.0000 Uiso DR . . . . . . H121 H 0.3319 -0.0250 -0.3900 0.0632 1.0000 Uiso DR . . . . . . H122 H 0.3889 0.1064 -0.4189 0.0630 1.0000 Uiso DR . . . . . . H123 H 0.5234 0.0317 -0.3826 0.0625 1.0000 Uiso DR . . . . . . H131 H 0.9109 -0.0891 0.0796 0.0411 1.0000 Uiso DR . . . . . . H132 H 0.9305 -0.2172 0.1096 0.0410 1.0000 Uiso DR . . . . . . H133 H 1.0667 -0.1565 0.0533 0.0407 1.0000 Uiso DR . . . . . . H141 H 1.2754 0.0787 0.1543 0.0434 1.0000 Uiso DR . . . . . . H142 H 1.2593 0.1916 0.2744 0.0430 1.0000 Uiso DR . . . . . . H143 H 1.1132 0.1400 0.1659 0.0427 1.0000 Uiso DR . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0155(2) 0.0174(3) 0.0122(2) 0.00269(19) 0.00027(17) 0.00882(19) Cl1 0.0166(4) 0.0171(5) 0.0186(4) 0.0064(4) 0.0023(3) 0.0057(4) S1 0.0321(6) 0.0336(6) 0.0205(5) 0.0083(5) 0.0030(4) 0.0114(5) S2 0.0310(5) 0.0232(6) 0.0220(5) 0.0082(4) 0.0089(4) 0.0156(5) O1 0.0184(13) 0.0214(15) 0.0150(13) 0.0033(11) 0.0001(10) 0.0119(11) O2 0.0221(14) 0.0291(17) 0.0165(13) 0.0044(12) 0.0069(11) 0.0124(12) O3 0.0257(15) 0.0373(18) 0.0152(13) 0.0080(13) 0.0005(11) 0.0159(13) O4 0.0489(19) 0.0346(19) 0.0205(15) 0.0115(14) 0.0073(13) 0.0182(15) O5 0.0357(16) 0.0276(17) 0.0200(14) 0.0080(13) 0.0127(12) 0.0198(13) N1 0.0165(15) 0.0146(17) 0.0125(14) 0.0006(13) 0.0013(12) 0.0035(13) N2 0.0198(16) 0.0215(18) 0.0101(14) 0.0013(13) 0.0016(12) 0.0104(14) N3 0.0187(15) 0.0266(19) 0.0093(14) 0.0010(14) 0.0026(12) 0.0062(14) N4 0.0164(15) 0.0254(19) 0.0138(15) 0.0069(14) 0.0015(12) 0.0113(14) N5 0.0146(15) 0.0198(17) 0.0135(15) 0.0042(13) 0.0035(12) 0.0066(13) C1 0.0139(16) 0.015(2) 0.0188(18) 0.0058(16) 0.0046(14) 0.0036(15) C2 0.0192(18) 0.014(2) 0.0144(17) 0.0042(15) 0.0019(14) 0.0073(15) C3 0.0224(19) 0.014(2) 0.0107(17) 0.0023(15) 0.0007(14) 0.0015(15) C4 0.0160(17) 0.025(2) 0.0173(18) 0.0113(17) -0.0018(14) 0.0056(16) C5 0.0220(19) 0.022(2) 0.0208(19) 0.0067(17) 0.0059(16) 0.0108(17) C6 0.0125(17) 0.017(2) 0.0177(18) 0.0054(16) 0.0017(14) 0.0064(15) C7 0.0157(17) 0.017(2) 0.0141(17) 0.0033(15) 0.0024(14) 0.0055(15) C8 0.0177(18) 0.016(2) 0.0167(18) 0.0057(16) 0.0038(14) 0.0028(15) C9 0.0149(17) 0.018(2) 0.0118(16) 0.0024(15) 0.0009(14) 0.0010(15) C10 0.0176(18) 0.026(2) 0.0148(18) 0.0078(17) 0.0052(15) 0.0040(16) C11 0.049(3) 0.035(3) 0.053(3) 0.022(3) -0.011(3) 0.003(2) C12 0.055(3) 0.038(3) 0.028(2) 0.016(2) 0.004(2) 0.009(2) C13 0.040(2) 0.018(2) 0.024(2) -0.0006(18) 0.0133(19) 0.0017(19) C14 0.025(2) 0.025(2) 0.030(2) 0.0085(19) 0.0061(17) 0.0055(18) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl1 2_666 Cu1 . Cl1 . 91.40(3) yes Cl1 2_666 Cu1 . O1 . 90.49(8) yes Cl1 . Cu1 . O1 . 94.31(8) yes Cl1 2_666 Cu1 . N1 . 113.64(9) yes Cl1 . Cu1 . N1 . 154.16(9) yes O1 . Cu1 . N1 . 91.90(11) yes Cl1 2_666 Cu1 . N5 . 89.48(9) yes Cl1 . Cu1 . N5 . 95.03(9) yes O1 . Cu1 . N5 . 170.66(12) yes N1 . Cu1 . N5 . 79.57(12) yes Cu1 2_666 Cl1 . Cu1 . 88.60(3) yes O4 . S1 . C11 . 104.8(2) yes O4 . S1 . C12 . 105.4(2) yes C11 . S1 . C12 . 97.8(3) yes O5 . S2 . C13 . 106.33(19) yes O5 . S2 . C14 . 106.21(18) yes C13 . S2 . C14 . 97.1(2) yes Cu1 . O1 . C1 . 127.7(2) yes Cu1 . N1 . N2 . 113.8(2) yes Cu1 . N1 . C7 . 128.4(2) yes N2 . N1 . C7 . 117.8(3) yes N1 . N2 . C8 . 114.1(3) yes N1 . N2 . H2 . 121.7 no C8 . N2 . H2 . 123.0 no C9 . N3 . C10 . 126.3(3) yes C9 . N3 . H3 . 116.6 no C10 . N3 . H3 . 117.1 no N5 . N4 . C10 . 124.3(3) yes N5 . N4 . H4 . 116.8 no C10 . N4 . H4 . 117.7 no N4 . N5 . Cu1 . 128.0(2) yes N4 . N5 . C8 . 118.2(3) yes Cu1 . N5 . C8 . 113.5(2) yes O1 . C1 . C2 . 118.1(3) yes O1 . C1 . C6 . 124.9(3) yes C2 . C1 . C6 . 117.0(3) yes C1 . C2 . C3 . 121.7(3) yes C1 . C2 . H21 . 118.8 no C3 . C2 . H21 . 119.4 no C2 . C3 . C4 . 121.1(3) yes C2 . C3 . H31 . 119.4 no C4 . C3 . H31 . 119.5 no C3 . C4 . C5 . 118.7(3) yes C3 . C4 . H41 . 120.6 no C5 . C4 . H41 . 120.6 no C4 . C5 . C6 . 121.5(3) yes C4 . C5 . H51 . 119.6 no C6 . C5 . H51 . 118.9 no C1 . C6 . C5 . 119.9(3) yes C1 . C6 . C7 . 123.3(3) yes C5 . C6 . C7 . 116.7(3) yes C6 . C7 . N1 . 123.4(3) yes C6 . C7 . H71 . 118.7 no N1 . C7 . H71 . 117.9 no N2 . C8 . N5 . 119.0(3) yes N2 . C8 . C9 . 117.3(3) yes N5 . C8 . C9 . 123.7(3) yes C8 . C9 . N3 . 112.2(3) yes C8 . C9 . O2 . 123.0(3) yes N3 . C9 . O2 . 124.7(3) yes N3 . C10 . N4 . 115.2(3) yes N3 . C10 . O3 . 121.3(3) yes N4 . C10 . O3 . 123.5(3) yes S1 . C11 . H111 . 108.1 no S1 . C11 . H112 . 107.6 no H111 . C11 . H112 . 110.8 no S1 . C11 . H113 . 108.4 no H111 . C11 . H113 . 111.5 no H112 . C11 . H113 . 110.2 no S1 . C12 . H121 . 107.9 no S1 . C12 . H122 . 109.8 no H121 . C12 . H122 . 110.7 no S1 . C12 . H123 . 108.9 no H121 . C12 . H123 . 109.9 no H122 . C12 . H123 . 109.7 no S2 . C13 . H131 . 108.6 no S2 . C13 . H132 . 109.0 no H131 . C13 . H132 . 110.2 no S2 . C13 . H133 . 107.9 no H131 . C13 . H133 . 110.5 no H132 . C13 . H133 . 110.6 no S2 . C14 . H141 . 108.8 no S2 . C14 . H142 . 108.9 no H141 . C14 . H142 . 110.9 no S2 . C14 . H143 . 108.9 no H141 . C14 . H143 . 110.1 no H142 . C14 . H143 . 109.2 no loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . Cl1 2_666 2.6454(10) yes Cu1 . Cl1 . 2.3083(10) yes Cu1 . O1 . 1.901(3) yes Cu1 . N1 . 1.963(3) yes Cu1 . N5 . 2.000(3) yes S1 . O4 . 1.512(3) yes S1 . C11 . 1.765(5) yes S1 . C12 . 1.741(5) yes S2 . O5 . 1.516(3) yes S2 . C13 . 1.781(4) yes S2 . C14 . 1.774(4) yes O1 . C1 . 1.317(4) yes O2 . C9 . 1.205(4) yes O3 . C10 . 1.216(4) yes N1 . N2 . 1.386(4) yes N1 . C7 . 1.292(5) yes N2 . C8 . 1.339(5) yes N2 . H2 . 0.869 no N3 . C9 . 1.356(5) yes N3 . C10 . 1.398(5) yes N3 . H3 . 0.876 no N4 . N5 . 1.382(4) yes N4 . C10 . 1.355(5) yes N4 . H4 . 0.862 no N5 . C8 . 1.298(5) yes C1 . C2 . 1.418(5) yes C1 . C6 . 1.421(5) yes C2 . C3 . 1.375(5) yes C2 . H21 . 0.933 no C3 . C4 . 1.397(5) yes C3 . H31 . 0.942 no C4 . C5 . 1.377(5) yes C4 . H41 . 0.932 no C5 . C6 . 1.415(5) yes C5 . H51 . 0.951 no C6 . C7 . 1.433(5) yes C7 . H71 . 0.944 no C8 . C9 . 1.492(5) yes C11 . H111 . 0.963 no C11 . H112 . 0.969 no C11 . H113 . 0.964 no C12 . H121 . 0.958 no C12 . H122 . 0.963 no C12 . H123 . 0.959 no C13 . H131 . 0.954 no C13 . H132 . 0.950 no C13 . H133 . 0.961 no C14 . H141 . 0.963 no C14 . H142 . 0.965 no C14 . H143 . 0.953 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N2 . H2 . O5 . 160 0.87 1.83 2.660(6) yes N3 . H3 . O4 . 176 0.88 1.84 2.714(6) yes N4 . H4 . O1 2_666 160 0.86 2.13 2.952(6) yes C2 . H21 . O3 2_666 140 0.93 2.49 3.265(6) yes C7 . H71 . O5 . 134 0.94 2.48 3.207(6) yes C13 . H131 . O2 . 155 0.95 2.45 3.338(6) yes _journal_paper_doi 10.1039/b905593b