#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/36/2203645.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_2203645 loop_ _publ_author_name 'Akitsu, Takashiro' 'Einaga, Yasuaki' _publ_section_title ; trans-Bis(5,5-diphenylhydantoinato)bis(2-phenylethylamine)copper(II) ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m524 _journal_page_last m526 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac '[Cu (C15 H11 N2 O2)2 (C8 H11 N)2]' _chemical_formula_moiety 'C46 H44 Cu N6 O4' _chemical_formula_sum 'C46 H44 Cu N6 O4' _chemical_formula_weight 808.42 _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' _cell_angle_alpha 90 _cell_angle_beta 95.08(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.050(9) _cell_length_b 18.502(10) _cell_length_c 9.916(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 297.0(10) _cell_measurement_theta_max 13.0 _cell_measurement_theta_min 10.4 _cell_volume 2019(2) _computing_cell_refinement 'WinAFC Diffractometer Control Software' _computing_data_collection 'WinAFC Diffractometer Control Software (Rigaku, 1999)' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 2001)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device_type 'Rigaku AFC-7R' _diffrn_measurement_method \w-2\q _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5357 _diffrn_reflns_theta_full 27.51 _diffrn_reflns_theta_max 27.51 _diffrn_standards_decay_% 3.26 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.593 _exptl_absorpt_correction_T_max 0.837 _exptl_absorpt_correction_T_min 0.708 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour 'red violet' _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 846.0 _exptl_crystal_size_max 0.700 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.300 _refine_diff_density_max 0.55 _refine_diff_density_min -0.94 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment noref _refine_ls_number_parameters 259 _refine_ls_number_reflns 4635 _refine_ls_R_factor_gt 0.0472 _refine_ls_shift/su_max 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.0561P)^2^+2.676P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1515 _reflns_number_gt 4635 _reflns_number_total 4643 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ng6018.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2203645 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cu Cu 0.320 1.265 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.148 0.159 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 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 0.5000 0.5000 0.5000 0.0351(2) Uani d S 1.00 Cu O1 0.5641(2) 0.48760(10) 0.8337(2) 0.0410(6) Uani d . 1.00 O O2 0.2446(2) 0.5762(2) 0.5626(2) 0.0493(6) Uani d . 1.00 O N1 0.4205(2) 0.52720(10) 0.6639(2) 0.0324(5) Uani d . 1.00 N N2 0.3783(2) 0.5292(2) 0.8807(2) 0.0359(6) Uani d . 1.00 N N3 0.4551(3) 0.5961(2) 0.4112(3) 0.0571(9) Uani d . 1.00 N C1 0.4629(3) 0.5120(2) 0.7974(3) 0.0306(6) Uani d . 1.00 C C2 0.3073(3) 0.5544(2) 0.6623(3) 0.0328(6) Uani d . 1.00 C C3 0.2658(3) 0.5544(2) 0.8083(3) 0.0315(6) Uani d . 1.00 C C4 0.1621(3) 0.5005(2) 0.8200(3) 0.0357(6) Uani d . 1.00 C C5 0.1554(4) 0.4625(2) 0.9407(4) 0.0501(9) Uani d . 1.00 C C6 0.0613(4) 0.4156(3) 0.9560(5) 0.0670(10) Uani d . 1.00 C C7 -0.0274(5) 0.4042(3) 0.8544(6) 0.0770(10) Uani d . 1.00 C C8 -0.0235(5) 0.4416(3) 0.7349(6) 0.0800(10) Uani d . 1.00 C C9 0.0709(4) 0.4893(2) 0.7166(4) 0.0600(10) Uani d . 1.00 C C10 0.2296(3) 0.6297(2) 0.8513(3) 0.0332(6) Uani d . 1.00 C C11 0.1283(3) 0.6632(2) 0.7886(4) 0.0463(8) Uani d . 1.00 C C12 0.0938(4) 0.7313(2) 0.8297(4) 0.0580(10) Uani d . 1.00 C C13 0.1582(4) 0.7663(2) 0.9324(5) 0.0580(10) Uani d . 1.00 C C14 0.2577(4) 0.7335(2) 0.9962(5) 0.0650(10) Uani d . 1.00 C C15 0.2947(3) 0.6656(2) 0.9568(4) 0.0500(9) Uani d . 1.00 C C16 0.5543(5) 0.6455(2) 0.3803(4) 0.0630(10) Uani d . 1.00 C C17 0.5145(5) 0.7021(3) 0.2760(5) 0.0780(10) Uani d . 1.00 C C18 0.6172(4) 0.7484(2) 0.2325(4) 0.0580(10) Uani d . 1.00 C C19 0.6264(5) 0.8207(3) 0.2679(4) 0.0710(10) Uani d . 1.00 C C20 0.7157(6) 0.8641(3) 0.2243(6) 0.084(2) Uani d . 1.00 C C21 0.7990(5) 0.8357(4) 0.1445(7) 0.094(2) Uani d . 1.00 C C22 0.7926(5) 0.7635(4) 0.1077(7) 0.089(2) Uani d . 1.00 C C23 0.7029(5) 0.7209(2) 0.1523(5) 0.0680(10) Uani d . 1.00 C H1 0.3904 0.5254 0.9765 0.0431 Uiso calc . 1.00 H H2 0.2167 0.4692 1.0130 0.0601 Uiso calc . 1.00 H H3 0.0582 0.3905 1.0393 0.0806 Uiso calc . 1.00 H H4 -0.0911 0.3709 0.8657 0.0921 Uiso calc . 1.00 H H5 -0.0860 0.4347 0.6641 0.0957 Uiso calc . 1.00 H H6 0.0730 0.5143 0.6331 0.0725 Uiso calc . 1.00 H H7 0.0816 0.6395 0.7167 0.0556 Uiso calc . 1.00 H H8 0.0239 0.7537 0.7851 0.0697 Uiso calc . 1.00 H H9 0.1344 0.8131 0.9595 0.0699 Uiso calc . 1.00 H H10 0.3026 0.7575 1.0691 0.0775 Uiso calc . 1.00 H H11 0.3647 0.6438 1.0022 0.0600 Uiso calc . 1.00 H H12 0.4087 0.5860 0.3280 0.0685 Uiso calc . 1.00 H H13 0.4061 0.6213 0.4696 0.0685 Uiso calc . 1.00 H H14 0.5840 0.6692 0.4615 0.0760 Uiso calc . 1.00 H H15 0.6176 0.6177 0.3472 0.0760 Uiso calc . 1.00 H H16 0.4770 0.6784 0.1982 0.0934 Uiso calc . 1.00 H H17 0.4570 0.7329 0.3131 0.0934 Uiso calc . 1.00 H H18 0.5695 0.8408 0.3239 0.0853 Uiso calc . 1.00 H H19 0.7198 0.9137 0.2492 0.1011 Uiso calc . 1.00 H H20 0.8612 0.8655 0.1144 0.1125 Uiso calc . 1.00 H H21 0.8500 0.7437 0.0520 0.1066 Uiso calc . 1.00 H H22 0.6993 0.6713 0.1277 0.0816 Uiso calc . 1.00 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 0.0545(3) 0.0380(3) 0.0132(2) 0.0096(3) 0.0061(2) 0.0032(2) O1 0.0400(10) 0.064(2) 0.0186(9) 0.0170(10) 0.0019(8) 0.0029(9) O2 0.0520(10) 0.069(2) 0.0250(10) 0.0150(10) -0.0043(10) 0.0140(10) N1 0.0440(10) 0.0410(10) 0.0122(10) 0.0090(10) 0.0007(9) 0.0021(9) N2 0.0380(10) 0.055(2) 0.0140(10) 0.0140(10) 0.0020(9) 0.0050(10) N3 0.098(3) 0.050(2) 0.0260(10) 0.028(2) 0.0220(10) 0.0110(10) C1 0.038(2) 0.040(2) 0.0140(10) 0.0060(10) 0.0000(10) 0.0020(10) C2 0.042(2) 0.038(2) 0.0180(10) 0.0050(10) 0.0000(10) 0.0040(10) C3 0.034(2) 0.043(2) 0.0170(10) 0.0080(10) 0.0020(10) 0.0040(10) C4 0.041(2) 0.0310(10) 0.0360(10) 0.0060(10) 0.0080(10) -0.0030(10) C5 0.055(2) 0.053(2) 0.044(2) 0.008(2) 0.019(2) 0.012(2) C6 0.070(3) 0.058(3) 0.079(3) -0.002(2) 0.037(2) 0.008(2) C7 0.076(3) 0.057(3) 0.103(4) -0.025(2) 0.041(3) -0.018(3) C8 0.075(3) 0.080(3) 0.083(3) -0.031(3) 0.003(3) -0.026(3) C9 0.063(2) 0.069(3) 0.049(2) -0.021(2) -0.001(2) -0.004(2) C10 0.036(2) 0.037(2) 0.0280(10) 0.0000(10) 0.0070(10) 0.0030(10) C11 0.052(2) 0.043(2) 0.042(2) 0.011(2) -0.006(2) -0.0010(10) C12 0.062(2) 0.052(2) 0.059(2) 0.017(2) -0.002(2) 0.003(2) C13 0.074(3) 0.030(2) 0.071(3) 0.007(2) 0.010(2) -0.006(2) C14 0.069(3) 0.057(3) 0.066(3) -0.007(2) -0.008(2) -0.019(2) C15 0.049(2) 0.050(2) 0.050(2) 0.004(2) -0.007(2) -0.011(2) C16 0.103(3) 0.046(2) 0.036(2) -0.002(2) -0.018(2) 0.006(2) C17 0.105(4) 0.071(3) 0.059(3) 0.022(3) 0.016(3) 0.029(2) C18 0.084(3) 0.054(2) 0.037(2) 0.017(2) -0.001(2) 0.014(2) C19 0.107(4) 0.063(3) 0.042(2) 0.022(3) 0.000(2) -0.001(2) C20 0.093(4) 0.066(3) 0.086(4) 0.006(3) -0.033(3) -0.019(3) C21 0.056(3) 0.085(4) 0.135(5) -0.010(3) -0.021(3) 0.011(4) C22 0.058(3) 0.095(4) 0.114(4) 0.013(3) 0.014(3) 0.001(4) C23 0.086(3) 0.054(3) 0.063(3) 0.023(2) 0.005(2) -0.001(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cu1 N1 1.979(2) yes Cu1 N3 2.026(3) yes O1 C1 1.230(4) no O2 C2 1.225(4) no N1 C1 1.393(3) no N1 C2 1.347(4) no N2 C1 1.340(4) no N2 C3 1.457(4) no N2 H1 0.950 no N3 C16 1.480(6) no N3 H12 0.950 no N3 H13 0.950 no C2 C3 1.556(4) no C3 C4 1.531(4) no C3 C10 1.521(4) no C4 C5 1.395(5) no C4 C9 1.388(5) no C5 C6 1.374(6) no C5 H2 0.950 no C6 C7 1.358(7) no C6 H3 0.950 no C7 C8 1.376(8) no C7 H4 0.950 no C8 C9 1.390(7) no C8 H5 0.950 no C9 H6 0.950 no C10 C11 1.379(5) no C10 C15 1.386(5) no C11 C12 1.388(6) no C11 H7 0.950 no C12 C13 1.355(6) no C12 H8 0.950 no C13 C14 1.362(6) no C13 H9 0.950 no C14 C15 1.387(6) no C14 H10 0.950 no C15 H11 0.950 no C16 C17 1.510(6) no C16 H14 0.950 no C16 H15 0.950 no C17 C18 1.515(7) no C17 H16 0.950 no C17 H17 0.950 no C18 C19 1.385(7) no C18 C23 1.387(7) no C19 C20 1.372(8) no C19 H18 0.950 no C20 C21 1.371(9) no C20 H19 0.950 no C21 C22 1.384(9) no C21 H20 0.950 no C22 C23 1.370(8) no C22 H21 0.950 no C23 H22 0.950 no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 Cu1 N3 . 91.40(10) yes N1 Cu1 N3 3_666 88.60(10) yes Cu1 N1 C1 . 126.3(2) no Cu1 N1 C2 . 124.4(2) no C1 N1 C2 . 108.7(2) no C1 N2 C3 . 112.6(2) no C1 N2 H1 . 123.7 no C3 N2 H1 . 123.7 no Cu1 N3 C16 . 118.3(3) yes Cu1 N3 H12 . 107.2 no Cu1 N3 H13 . 107.2 no C16 N3 H12 . 107.2 no C16 N3 H13 . 107.2 no H12 N3 H13 . 109.5 no O1 C1 N1 . 124.9(3) no O1 C1 N2 . 125.0(2) no N1 C1 N2 . 110.1(2) no O2 C2 N1 . 126.2(3) no O2 C2 C3 . 124.0(3) no N1 C2 C3 . 109.8(2) no N2 C3 C2 . 98.6(2) no N2 C3 C4 . 111.5(3) no N2 C3 C10 . 112.9(2) no C2 C3 C4 . 110.8(2) no C2 C3 C10 . 111.6(2) no C4 C3 C10 . 111.0(3) no C3 C4 C5 . 119.3(3) no C3 C4 C9 . 122.7(3) no C5 C4 C9 . 117.9(3) no C4 C5 C6 . 120.7(3) no C4 C5 H2 . 119.6 no C6 C5 H2 . 119.6 no C5 C6 C7 . 121.3(5) no C5 C6 H3 . 119.3 no C7 C6 H3 . 119.3 no C6 C7 C8 . 119.0(5) no C6 C7 H4 . 120.5 no C8 C7 H4 . 120.5 no C7 C8 C9 . 120.9(5) no C7 C8 H5 . 119.6 no C9 C8 H5 . 119.6 no C4 C9 C8 . 120.1(4) no C4 C9 H6 . 119.9 no C8 C9 H6 . 119.9 no C3 C10 C11 . 120.6(3) no C3 C10 C15 . 121.3(3) no C11 C10 C15 . 118.1(3) no C10 C11 C12 . 120.6(3) no C10 C11 H7 . 119.7 no C12 C11 H7 . 119.7 no C11 C12 C13 . 121.0(4) no C11 C12 H8 . 119.5 no C13 C12 H8 . 119.5 no C12 C13 C14 . 118.9(4) no C12 C13 H9 . 120.5 no C14 C13 H9 . 120.5 no C13 C14 C15 . 121.3(4) no C13 C14 H10 . 119.4 no C15 C14 H10 . 119.4 no C10 C15 C14 . 120.1(3) no C10 C15 H11 . 120.0 no C14 C15 H11 . 120.0 no N3 C16 C17 . 113.2(4) no N3 C16 H14 . 108.5 no N3 C16 H15 . 108.5 no C17 C16 H14 . 108.5 no C17 C16 H15 . 108.5 no H14 C16 H15 . 109.5 no C16 C17 C18 . 114.0(4) no C16 C17 H16 . 108.3 no C16 C17 H17 . 108.3 no C18 C17 H16 . 108.3 no C18 C17 H17 . 108.3 no H16 C17 H17 . 109.5 no C17 C18 C19 . 121.0(4) no C17 C18 C23 . 121.5(4) no C19 C18 C23 . 117.5(4) no C18 C19 C20 . 121.6(5) no C18 C19 H18 . 119.2 no C20 C19 H18 . 119.2 no C19 C20 C21 . 119.7(5) no C19 C20 H19 . 120.2 no C21 C20 H19 . 120.2 no C20 C21 C22 . 120.1(6) no C20 C21 H20 . 119.9 no C22 C21 H20 . 119.9 no C21 C22 C23 . 119.4(5) no C21 C22 H21 . 120.3 no C23 C22 H21 . 120.3 no C18 C23 C22 . 121.6(5) no C18 C23 H22 . 119.2 no C22 C23 H22 . 119.2 no 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_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Cu1 N1 C1 O1 . . . 9.9(4) no Cu1 N1 C1 N2 . . . -171.2(2) no Cu1 N1 C2 O2 . . . -11.6(5) no Cu1 N1 C2 C3 . . . 168.5(2) no Cu1 N1 C1 O1 3_666 3_666 3_666 -9.9(4) no Cu1 N1 C1 N2 3_666 3_666 3_666 171.2(2) no Cu1 N1 C2 O2 3_666 3_666 3_666 11.6(5) no Cu1 N1 C2 C3 3_666 3_666 3_666 -168.5(2) no Cu1 N3 C16 C17 . . . 161.0(3) no Cu1 N3 C16 C17 3_666 3_666 3_666 -161.0(3) no O1 C1 N1 C2 . . . -178.9(3) no O1 C1 N2 C3 . . . -177.9(3) no O2 C2 N1 C1 . . . 176.9(3) no O2 C2 C3 N2 . . . -175.4(3) no O2 C2 C3 C4 . . . 67.6(4) no O2 C2 C3 C10 . . . -56.5(4) no N1 Cu1 N3 C16 . . . 116.4(3) no N1 Cu1 N3 C16 . 3_666 3_666 63.6(3) no N1 C1 N2 C3 . . . 3.3(4) no N1 C2 C3 N2 . . . 4.5(3) no N1 C2 C3 C4 . . . -112.5(3) no N1 C2 C3 C10 . . . 123.4(3) no N2 C1 N1 C2 . . . 0.0(3) no N2 C3 C4 C5 . . . 36.0(4) no N2 C3 C4 C9 . . . -146.2(3) no N2 C3 C10 C11 . . . 177.1(3) no N2 C3 C10 C15 . . . -4.9(4) no N3 Cu1 N1 C1 . . . -140.8(3) no N3 Cu1 N1 C2 . . . 49.3(3) no N3 Cu1 N1 C1 . 3_666 3_666 -39.2(3) no N3 Cu1 N1 C2 . 3_666 3_666 130.7(3) no N3 C16 C17 C18 . . . -174.1(3) no C1 N1 C2 C3 . . . -3.0(3) no C1 N2 C3 C2 . . . -4.6(3) no C1 N2 C3 C4 . . . 111.9(3) no C1 N2 C3 C10 . . . -122.5(3) no C2 C3 C4 C5 . . . 144.7(3) no C2 C3 C4 C9 . . . -37.5(4) no C2 C3 C10 C11 . . . 67.1(4) no C2 C3 C10 C15 . . . -115.0(3) no C3 C4 C5 C6 . . . 177.9(4) no C3 C4 C9 C8 . . . -177.6(4) no C3 C10 C11 C12 . . . 178.7(3) no C3 C10 C15 C14 . . . -178.3(3) no C4 C3 C10 C11 . . . -57.0(4) no C4 C3 C10 C15 . . . 121.0(3) no C4 C5 C6 C7 . . . 0.5(7) no C4 C9 C8 C7 . . . -0.9(7) no C5 C4 C3 C10 . . . -90.7(4) no C5 C4 C9 C8 . . . 0.2(6) no C5 C6 C7 C8 . . . -1.2(8) no C6 C5 C4 C9 . . . 0.0(6) no C6 C7 C8 C9 . . . 1.3(8) no C9 C4 C3 C10 . . . 87.0(4) no C10 C11 C12 C13 . . . -0.3(6) no C10 C15 C14 C13 . . . -0.5(7) no C11 C10 C15 C14 . . . -0.3(5) no C11 C12 C13 C14 . . . -0.5(7) no C12 C11 C10 C15 . . . 0.6(5) no C12 C13 C14 C15 . . . 0.9(7) no C16 C17 C18 C19 . . . -110.7(5) no C16 C17 C18 C23 . . . 71.5(5) no C17 C18 C19 C20 . . . -177.0(4) no C17 C18 C23 C22 . . . 177.0(5) no C18 C19 C20 C21 . . . -0.6(8) no C18 C23 C22 C21 . . . 0.7(8) no C19 C18 C23 C22 . . . -0.9(7) no C19 C20 C21 C22 . . . 0.3(9) no C20 C19 C18 C23 . . . 0.9(7) no C20 C21 C22 C23 . . . -0.4(9) no C20 C21 C22 C23 . . . -0.4(9) no 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 N3 H13 O2 . 0.95 2.24 2.901(4) 126 yes N3 H12 O1 3_666 0.95 2.15 2.872(3) 132 yes N2 H1 O1 3_667 0.95 1.92 2.864(3) 172 yes _journal_paper_doi 10.1107/S1600536804007378