#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2014000.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_2014000 loop_ _publ_author_name 'Curtis, Neil F.' 'Gladkikh, Olga P.' 'Morgan, Keith R.' 'Heath, Sarah L.' _publ_section_title ; (4,4,12,12-Tetramethyl-5,8,11-triazapenta-2,14-dione 2-oxime 14-oximato-\k^5^N)copper(II) perchlorate: a copper(II) compound with a pentadentate triamine--oxime--oximate ligand ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first m256 _journal_page_last m257 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac '[Cu (C16 H34 N5 O2)] Cl O4' _chemical_formula_moiety 'C16 H34 Cu N5 O2 + , Cl O4 -' _chemical_formula_sum 'C16 H34 Cl Cu N5 O6' _chemical_formula_weight 491.47 _chemical_name_systematic ; (4,4,12,12-Tetramethyl-5,8,11-triazapenta-2,14-dione 2-oxime 14-oximato-\k^5^N)copper(II) perchlorate ; _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 _cell_angle_alpha 90.00 _cell_angle_beta 90.058(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.8307(7) _cell_length_b 23.9974(15) _cell_length_c 8.6318(6) _cell_measurement_reflns_used 9707 _cell_measurement_temperature 160(2) _cell_measurement_theta_max 28.40 _cell_measurement_theta_min 2.08 _cell_volume 2243.5(3) _computing_cell_refinement 'local programs' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 160(2) _diffrn_measured_fraction_theta_full 0.863 _diffrn_measured_fraction_theta_max 0.863 _diffrn_measurement_device 'Siemens SMART CCD area-detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 12927 _diffrn_reflns_theta_full 28.36 _diffrn_reflns_theta_max 28.36 _diffrn_reflns_theta_min 1.70 _exptl_absorpt_coefficient_mu 1.133 _exptl_absorpt_correction_T_max 0.895 _exptl_absorpt_correction_T_min 0.540 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1036 _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.639 _refine_diff_density_min -0.697 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 4845 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.122 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0403 _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^)+(0.0379P)^2^+3.1169P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0958 _refine_ls_wR_factor_ref 0.1004 _reflns_number_gt 4392 _reflns_number_total 4845 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd1308.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2014000 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 0.26542(2) 0.346322(12) 0.81688(3) 0.01749(9) Uani d . 1 Cu N2 0.4077(2) 0.28900(9) 0.8262(2) 0.0238(4) Uani d . 1 N O2 0.37197(19) 0.23610(8) 0.8847(2) 0.0346(4) Uani d . 1 O H2 0.275(3) 0.2292(15) 0.838(4) 0.052 Uiso d . 1 H C1 0.6098(3) 0.24921(13) 0.8809(4) 0.0403(7) Uani d . 1 C H1A 0.6958 0.2620 0.8798 0.060 Uiso calc R 1 H H1B 0.6011 0.2168 0.8128 0.060 Uiso calc R 1 H H1C 0.5866 0.2388 0.9868 0.060 Uiso calc R 1 H C2 0.5252(2) 0.29625(11) 0.8237(3) 0.0260(5) Uani d . 1 C C3 0.5853(2) 0.35189(11) 0.7758(3) 0.0264(5) Uani d . 1 C H3A 0.6483 0.3430 0.6965 0.032 Uiso calc R 1 H H3B 0.6304 0.3660 0.8676 0.032 Uiso calc R 1 H C4 0.5073(2) 0.40154(10) 0.7113(3) 0.0199(5) Uani d . 1 C C41 0.4550(2) 0.38715(11) 0.5513(3) 0.0255(5) Uani d . 1 C H4A 0.5231 0.3821 0.4779 0.038 Uiso calc R 1 H H4B 0.4016 0.4175 0.5156 0.038 Uiso calc R 1 H H4C 0.4069 0.3526 0.5579 0.038 Uiso calc R 1 H C42 0.5873(2) 0.45630(11) 0.6981(3) 0.0281(5) Uani d . 1 C H4D 0.6510 0.4512 0.6188 0.042 Uiso calc R 1 H H4E 0.6266 0.4641 0.7980 0.042 Uiso calc R 1 H H4F 0.5339 0.4876 0.6692 0.042 Uiso calc R 1 H N5 0.39863(17) 0.41209(8) 0.8164(2) 0.0183(4) Uani d . 1 N H5 0.3582 0.4428 0.7749 0.022 Uiso calc R 1 H C6 0.4288(2) 0.42768(11) 0.9806(3) 0.0237(5) Uani d . 1 C H6A 0.3852 0.4626 1.0074 0.028 Uiso calc R 1 H H6B 0.5186 0.4347 0.9895 0.028 Uiso calc R 1 H C7 0.3911(2) 0.38126(11) 1.0982(3) 0.0250(5) Uani d . 1 C H7A 0.4504 0.3500 1.0914 0.030 Uiso calc R 1 H H7B 0.3947 0.3964 1.2048 0.030 Uiso calc R 1 H N8 0.26537(19) 0.36052(9) 1.0665(2) 0.0226(4) Uani d . 1 N H8 0.2503 0.3276 1.1199 0.027 Uiso calc R 1 H C9 0.1673(2) 0.40327(12) 1.1010(3) 0.0285(6) Uani d . 1 C H9A 0.2049 0.4408 1.1050 0.034 Uiso calc R 1 H H9B 0.1298 0.3954 1.2032 0.034 Uiso calc R 1 H C10 0.0682(2) 0.40182(12) 0.9764(3) 0.0269(5) Uani d . 1 C H10A 0.0221 0.3663 0.9823 0.032 Uiso calc R 1 H H10B 0.0091 0.4327 0.9926 0.032 Uiso calc R 1 H N11 0.12680(17) 0.40724(9) 0.8219(2) 0.0196(4) Uani d . 1 N H11 0.1661 0.4417 0.8198 0.024 Uiso calc R 1 H C12 0.0397(2) 0.40594(11) 0.6866(3) 0.0241(5) Uani d . 1 C C121 0.1177(2) 0.40810(13) 0.5394(3) 0.0325(6) Uani d . 1 C H12A 0.0634 0.4110 0.4489 0.049 Uiso calc R 1 H H12B 0.1674 0.3741 0.5316 0.049 Uiso calc R 1 H H12C 0.1724 0.4406 0.5433 0.049 Uiso calc R 1 H C122 -0.0472(2) 0.45843(12) 0.6906(3) 0.0320(6) Uani d . 1 C H12D -0.0980 0.4593 0.5966 0.048 Uiso calc R 1 H H1DE 0.0031 0.4923 0.6959 0.048 Uiso calc R 1 H H1DF -0.1008 0.4564 0.7818 0.048 Uiso calc R 1 H C13 -0.0378(2) 0.35071(12) 0.6889(3) 0.0297(6) Uani d . 1 C H13A -0.0991 0.3546 0.7732 0.036 Uiso calc R 1 H H14B -0.0850 0.3496 0.5907 0.036 Uiso calc R 1 H C14 0.0225(2) 0.29281(12) 0.7086(3) 0.0301(6) Uani d . 1 C C15 -0.0560(3) 0.24084(15) 0.6724(5) 0.0522(9) Uani d . 1 C H15A -0.0257 0.2233 0.5772 0.078 Uiso calc R 1 H H15B -0.1424 0.2519 0.6585 0.078 Uiso calc R 1 H H15C -0.0497 0.2144 0.7585 0.078 Uiso calc R 1 H N14 0.13391(19) 0.28621(9) 0.7588(2) 0.0244(4) Uani d . 1 N O14 0.16859(18) 0.22928(8) 0.7772(2) 0.0332(4) Uani d . 1 O Cl1 0.24086(5) 0.57184(3) 0.78760(7) 0.02500(14) Uani d . 1 Cl O3 0.1308(2) 0.59374(10) 0.7192(3) 0.0506(6) Uani d . 1 O O4 0.2130(2) 0.53993(12) 0.9258(3) 0.0582(7) Uani d . 1 O O5 0.2965(4) 0.53074(15) 0.6855(4) 0.0956(13) Uani d . 1 O O6 0.3219(3) 0.61731(13) 0.8189(5) 0.0952(13) Uani d . 1 O 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 0.01918(15) 0.01854(16) 0.01474(14) 0.00032(11) 0.00124(10) -0.00069(10) N2 0.0294(10) 0.0197(10) 0.0224(10) 0.0034(8) 0.0008(8) 0.0003(8) O2 0.0387(11) 0.0239(10) 0.0413(11) 0.0000(8) -0.0028(9) 0.0111(8) C1 0.0339(15) 0.0363(16) 0.0507(18) 0.0111(13) -0.0039(13) 0.0069(14) C2 0.0280(12) 0.0275(13) 0.0227(11) 0.0079(10) -0.0008(9) -0.0017(10) C3 0.0198(11) 0.0309(14) 0.0285(12) 0.0048(10) 0.0010(9) -0.0023(10) C4 0.0177(10) 0.0247(12) 0.0172(10) -0.0002(9) 0.0030(8) -0.0013(9) C41 0.0255(12) 0.0344(14) 0.0168(11) -0.0013(10) 0.0047(9) -0.0005(10) C42 0.0254(12) 0.0334(14) 0.0254(12) -0.0056(11) 0.0053(10) -0.0007(11) N5 0.0182(9) 0.0228(10) 0.0139(8) 0.0003(7) 0.0013(7) 0.0003(7) C6 0.0267(12) 0.0264(13) 0.0181(11) -0.0037(10) 0.0013(9) -0.0049(9) C7 0.0291(12) 0.0311(14) 0.0147(10) 0.0003(10) -0.0017(9) -0.0013(9) N8 0.0270(10) 0.0259(11) 0.0150(9) -0.0018(8) 0.0024(8) 0.0021(8) C9 0.0293(13) 0.0379(15) 0.0182(11) 0.0019(11) 0.0072(10) -0.0051(10) C10 0.0249(12) 0.0347(15) 0.0213(11) 0.0008(10) 0.0084(9) -0.0021(10) N11 0.0184(9) 0.0232(10) 0.0172(9) 0.0001(8) 0.0015(7) -0.0003(8) C12 0.0194(11) 0.0321(14) 0.0210(11) 0.0020(10) 0.0001(9) 0.0021(10) C121 0.0255(12) 0.0510(18) 0.0209(12) 0.0069(12) 0.0005(10) 0.0068(11) C122 0.0236(12) 0.0378(16) 0.0346(14) 0.0065(11) -0.0008(10) 0.0037(12) C13 0.0201(11) 0.0388(16) 0.0304(13) -0.0011(11) -0.0024(10) -0.0060(11) C14 0.0264(12) 0.0340(15) 0.0299(13) -0.0049(11) 0.0025(10) -0.0097(11) C15 0.0358(16) 0.0418(19) 0.079(3) -0.0086(14) -0.0065(16) -0.0214(18) N14 0.0263(10) 0.0222(11) 0.0249(10) -0.0010(8) 0.0031(8) -0.0046(8) O14 0.0359(10) 0.0207(10) 0.0430(11) -0.0020(8) 0.0031(9) -0.0059(8) Cl1 0.0210(3) 0.0289(3) 0.0250(3) 0.0016(2) -0.0004(2) 0.0049(2) O3 0.0359(12) 0.0545(15) 0.0613(15) 0.0046(10) -0.0212(11) 0.0138(12) O4 0.0479(13) 0.0808(19) 0.0460(13) 0.0167(13) 0.0181(11) 0.0349(13) O5 0.137(3) 0.098(3) 0.0518(17) 0.078(2) 0.0264(18) 0.0059(16) O6 0.079(2) 0.068(2) 0.138(3) -0.0430(17) -0.067(2) 0.045(2) 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' 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' Cl Cl 0.1484 0.1585 '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' 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 N2 Cu1 N14 93.32(9) yes N2 Cu1 N11 175.79(8) yes N14 Cu1 N11 89.90(8) yes N2 Cu1 N5 89.33(8) yes N14 Cu1 N5 165.85(8) yes N11 Cu1 N5 88.20(8) yes N2 Cu1 N8 93.82(8) yes N14 Cu1 N8 110.13(8) yes N11 Cu1 N8 82.52(8) yes N5 Cu1 N8 83.53(7) yes C2 N2 O2 113.4(2) yes C2 N2 Cu1 130.37(18) yes O2 N2 Cu1 113.90(15) yes N2 O2 H2 104.9(19) ? C2 C1 H1A 109.5 ? C2 C1 H1B 109.5 ? H1A C1 H1B 109.5 ? C2 C1 H1C 109.5 ? H1A C1 H1C 109.5 ? H1B C1 H1C 109.5 ? N2 C2 C1 119.1(2) ? N2 C2 C3 122.7(2) yes C1 C2 C3 118.1(2) yes C2 C3 C4 121.8(2) yes C2 C3 H3A 106.9 ? C4 C3 H3A 106.9 ? C2 C3 H3B 106.9 ? C4 C3 H3B 106.9 ? H3A C3 H3B 106.7 ? N5 C4 C41 107.01(18) ? N5 C4 C3 109.59(19) ? C41 C4 C3 110.4(2) ? N5 C4 C42 109.42(19) ? C41 C4 C42 108.95(19) ? C3 C4 C42 111.35(19) ? C4 C41 H4A 109.5 ? C4 C41 H4B 109.5 ? H4A C41 H4B 109.5 ? C4 C41 H4C 109.5 ? H4A C41 H4C 109.5 ? H4B C41 H4C 109.5 ? C4 C42 H4D 109.5 ? C4 C42 H4E 109.5 ? H4D C42 H4E 109.5 ? C4 C42 H4F 109.5 ? H4D C42 H4F 109.5 ? H4E C42 H4F 109.5 ? C6 N5 C4 116.16(18) ? C6 N5 Cu1 109.17(14) ? C4 N5 Cu1 113.83(14) ? C6 N5 H5 105.6 ? C4 N5 H5 105.6 ? Cu1 N5 H5 105.6 ? N5 C6 C7 112.28(19) ? N5 C6 H6A 109.1 ? C7 C6 H6A 109.1 ? N5 C6 H6B 109.1 ? C7 C6 H6B 109.1 ? H6A C6 H6B 107.9 ? N8 C7 C6 111.22(19) ? N8 C7 H7A 109.4 ? C6 C7 H7A 109.4 ? N8 C7 H7B 109.4 ? C6 C7 H7B 109.4 ? H7A C7 H7B 108.0 ? C7 N8 C9 112.6(2) ? C7 N8 Cu1 103.58(13) ? C9 N8 Cu1 107.60(14) ? C7 N8 H8 110.9 ? C9 N8 H8 110.9 ? Cu1 N8 H8 110.9 ? N8 C9 C10 110.0(2) ? N8 C9 H9A 109.7 ? C10 C9 H9A 109.7 ? N8 C9 H9B 109.7 ? C10 C9 H9B 109.7 ? H9A C9 H9B 108.2 ? N11 C10 C9 109.4(2) ? N11 C10 H10A 109.8 ? C9 C10 H10A 109.8 ? N11 C10 H10B 109.8 ? C9 C10 H10B 109.8 ? H10A C10 H10B 108.2 ? C10 N11 C12 115.38(18) ? C10 N11 Cu1 105.33(15) ? C12 N11 Cu1 114.78(15) ? C10 N11 H11 106.9 ? C12 N11 H11 106.9 ? Cu1 N11 H11 106.9 ? N11 C12 C121 107.40(19) ? N11 C12 C13 110.1(2) ? C121 C12 C13 109.6(2) ? N11 C12 C122 110.0(2) ? C121 C12 C122 108.8(2) ? C13 C12 C122 110.8(2) ? C12 C121 H12A 109.5 ? C12 C121 H12B 109.5 ? H12A C121 H12B 109.5 ? C12 C121 H12C 109.5 ? H12A C121 H12C 109.5 ? H12B C121 H12C 109.5 ? C12 C122 H12D 109.5 ? C12 C122 H1DE 109.5 ? H12D C122 H1DE 109.5 ? C12 C122 H1DF 109.5 ? H12D C122 H1DF 109.5 ? H1DE C122 H1DF 109.5 ? C14 C13 C12 122.3(2) yes C14 C13 H13A 106.7 ? C12 C13 H13A 106.7 ? C14 C13 H14B 106.7 ? C12 C13 H14B 106.7 ? H13A C13 H14B 106.6 ? N14 C14 C15 118.9(3) yes N14 C14 C13 122.8(2) yes C15 C14 C13 118.2(2) yes C14 C15 H15A 109.5 ? C14 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? C14 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? C14 N14 O14 113.6(2) yes C14 N14 Cu1 129.26(19) yes O14 N14 Cu1 117.11(15) yes N14 O14 H2 106.7(17) ? O6 Cl1 O3 108.03(17) ? O6 Cl1 O4 112.1(2) ? O3 Cl1 O4 111.10(15) ? O6 Cl1 O5 112.3(3) ? O3 Cl1 O5 110.19(19) ? O4 Cl1 O5 103.13(18) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cu1 N2 2.067(2) yes Cu1 N14 2.088(2) yes Cu1 N11 2.096(2) yes Cu1 N5 2.138(2) yes Cu1 N8 2.1816(19) yes N2 C2 1.285(3) yes N2 O2 1.420(3) yes O2 H2 1.14(4) ? C1 C2 1.535(4) ? C1 H1A 0.9800 ? C1 H1B 0.9800 ? C1 H1C 0.9800 ? C2 C3 1.542(4) ? C3 C4 1.563(3) ? C3 H3A 0.9900 ? C3 H3B 0.9900 ? C4 N5 1.508(3) ? C4 C41 1.532(3) ? C4 C42 1.578(3) ? C41 H4A 0.9800 ? C41 H4B 0.9800 ? C41 H4C 0.9800 ? C42 H4D 0.9800 ? C42 H4E 0.9800 ? C42 H4F 0.9800 ? N5 C6 1.501(3) ? N5 H5 0.9300 ? C6 C7 1.561(3) ? C6 H6A 0.9900 ? C6 H6B 0.9900 ? C7 N8 1.475(3) ? C7 H7A 0.9900 ? C7 H7B 0.9900 ? N8 C9 1.507(3) ? N8 H8 0.9300 ? C9 C10 1.519(4) ? C9 H9A 0.9900 ? C9 H9B 0.9900 ? C10 N11 1.483(3) ? C10 H10A 0.9900 ? C10 H10B 0.9900 ? N11 C12 1.500(3) ? N11 H11 0.9300 ? C12 C121 1.527(3) ? C12 C13 1.569(4) ? C12 C122 1.573(4) ? C121 H12A 0.9800 ? C121 H12B 0.9800 ? C121 H12C 0.9800 ? C122 H12D 0.9800 ? C122 H1DE 0.9800 ? C122 H1DF 0.9800 ? C13 C14 1.545(4) ? C13 H13A 0.9900 ? C13 H14B 0.9900 ? C14 N14 1.292(3) yes C14 C15 1.541(4) ? C15 H15A 0.9800 ? C15 H15B 0.9800 ? C15 H15C 0.9800 ? N14 O14 1.426(3) yes O14 H2 1.27(4) ? Cl1 O6 1.426(3) ? Cl1 O3 1.429(2) ? Cl1 O4 1.449(2) ? Cl1 O5 1.454(3) ? 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 O2 H2 O14 . 1.14(4) 1.27(4) 2.395(3) 171(4) O2 H2 N14 . 1.14(4) 2.16(4) 3.044(3) 132(3) N5 H5 O5 . 0.93 2.34 3.257(4) 167 N8 H8 O14 4_566 0.93 2.12 3.009(3) 160 N11 H11 O4 . 0.93 2.58 3.437(4) 154