Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #==================================================================== # 1. SUBMISSION DETAILS _publ_contact_author 'Dr. Malcolm A. Halcrow' _publ_contact_author_address ; School of Chemistry, University of Leeds, Woodhouse Lane, Leeds LS2 9JT, UK ; _publ_contact_author_phone '+44 (0)113 3436506' _publ_contact_author_fax '+44 (0)113 3436565' _publ_contact_author_email m.a.halcrow@leeds.ac.uk _publ_contact_letter ; The following data refers to two structures included in a manuscript we have just submitted to the Chem. Comm. office. ; _publ_section_title ; Two complexes of copper(II) salts with 5-amino-3-(pyrid-2-yl)-1H-pyrazole, the prototype for a new class of ditopic ligand ; loop_ _publ_author_name _publ_author_address 'Christopher M. Pask' ; School of Chemistry, University of Leeds, Woodhouse Lane, Leeds LS2 9JT, UK ; 'Kenneth D. Camm' ; School of Chemistry, University of Leeds, Woodhouse Lane, Leeds LS2 9JT, UK ; 'Neil J. Bullen' ; School of Chemistry, University of Leeds, Woodhouse Lane, Leeds LS2 9JT, UK ; 'Michael J. Carr' ; School of Chemistry, University of Leeds, Woodhouse Lane, Leeds LS2 9JT, UK ; 'William Clegg' ; School of Natural Sciences, Bedson Building, University of Newcastle upon Tyne, Newcastle upon Tyne, NE1 7RU, UK ; 'Colin A. Kilner' ; School of Chemistry, University of Leeds, Woodhouse Lane, Leeds LS2 9JT, UK ; ; M.A.Halcrow ; ; School of Chemistry, University of Leeds, Woodhouse Lane, Leeds LS2 9JT, UK ; _publ_contact_author_name 'Dr. Malcolm A. Halcrow' #================================================================= data_c:\datasets\leeds\cp138\cp138 _database_code_depnum_ccdc_archive 'CCDC 283226' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis[3-(pyrid-2-yl)-5-aminopyrazole]bromocopper(II) bromide methanol solvate ; _chemical_name_common 'Bis(3-(pyrid-2-yl)-5-aminopyrazole)bromocopper(ii) bromide methanol solvate' _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 Br Cu N8, Br, C H4 O' _chemical_formula_sum 'C17 H20 Br2 Cu N8 O' _chemical_formula_weight 575.77 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8159(18) _cell_length_b 21.777(5) _cell_length_c 22.260(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4273.5(16) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11667 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 22.16 _exptl_crystal_description Plate _exptl_crystal_colour Brown _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2280 _exptl_absorpt_coefficient_mu 4.788 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.549 _exptl_absorpt_correction_T_max 1.292 _exptl_absorpt_process_details ; Sheldrick, G. M. (2002). SADABS v. 2.03. University of G/ottingen, Germany. ; _exptl_special_details ; Rotating anode power 4 kW. The thinness of the crystal, and its consequent weak diffracting power, required a 2.5-day data collection to collect to 2/q = 44\%. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex diffractometer' _diffrn_measurement_method 'Rotation images' _diffrn_detector_area_resol_mean '120 microns' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11667 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.0661 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 22.16 _reflns_number_total 2602 _reflns_number_gt 1834 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 software, Bruker Nonius 2004' _computing_cell_refinement 'APEX 2 software, Bruker Nonius 2004' _computing_data_reduction 'SAINT, Bruker Nonius 2004' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. No disorder was detected during refinement, and all non-H atoms were refined anisotropically. All H atoms were placed in calculated positions and refined using a riding model. The deepest Fourier hole of -1.4 e.\%A^-3^ is 1.0\%A from Br26. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1071P)^2^+4.8832P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2602 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0945 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1696 _refine_ls_wR_factor_gt 0.1379 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.76475(13) 0.58183(5) 0.38073(5) 0.0305(4) Uani 1 1 d . . . N2 N 0.9161(9) 0.6380(4) 0.4186(3) 0.0262(19) Uani 1 1 d . . . C3 C 0.8992(11) 0.6984(4) 0.4243(4) 0.032(3) Uani 1 1 d . . . H3 H 0.8099 0.7168 0.4086 0.038 Uiso 1 1 calc R . . C4 C 1.0044(13) 0.7353(5) 0.4517(4) 0.040(3) Uani 1 1 d . . . H4 H 0.9890 0.7783 0.4551 0.048 Uiso 1 1 calc R . . C5 C 1.1335(13) 0.7077(5) 0.4740(4) 0.044(3) Uani 1 1 d . . . H5 H 1.2084 0.7319 0.4935 0.053 Uiso 1 1 calc R . . C6 C 1.1545(12) 0.6461(5) 0.4684(4) 0.035(3) Uani 1 1 d . . . H6 H 1.2436 0.6274 0.4839 0.042 Uiso 1 1 calc R . . C7 C 1.0453(11) 0.6110(4) 0.4400(4) 0.026(2) Uani 1 1 d . . . C8 C 1.0501(11) 0.5440(4) 0.4320(4) 0.025(2) Uani 1 1 d . . . N9 N 0.9264(9) 0.5177(4) 0.4085(3) 0.028(2) Uani 1 1 d . . . N10 N 0.9587(9) 0.4567(4) 0.4056(3) 0.030(2) Uani 1 1 d . . . H10 H 0.8962 0.4284 0.3919 0.037 Uiso 1 1 calc R . . C11 C 1.1015(11) 0.4452(5) 0.4268(4) 0.030(2) Uani 1 1 d . . . C12 C 1.1627(11) 0.5004(4) 0.4446(4) 0.026(2) Uani 1 1 d . . . H12 H 1.2599 0.5074 0.4617 0.031 Uiso 1 1 calc R . . N13 N 1.1599(10) 0.3860(4) 0.4260(4) 0.042(2) Uani 1 1 d . . . H13A H 1.1049 0.3556 0.4118 0.050 Uiso 1 1 calc R . . H13B H 1.2519 0.3790 0.4397 0.050 Uiso 1 1 calc R . . N14 N 0.6365(9) 0.5220(3) 0.3354(3) 0.0294(19) Uani 1 1 d . . . C15 C 0.5490(11) 0.4803(5) 0.3586(5) 0.036(3) Uani 1 1 d . . . H15 H 0.5390 0.4789 0.4011 0.044 Uiso 1 1 calc R . . C16 C 0.4683(12) 0.4372(5) 0.3241(5) 0.044(3) Uani 1 1 d . . . H16 H 0.4037 0.4077 0.3424 0.053 Uiso 1 1 calc R . . C17 C 0.4868(12) 0.4393(5) 0.2628(5) 0.044(3) Uani 1 1 d . . . H17 H 0.4368 0.4103 0.2378 0.052 Uiso 1 1 calc R . . C18 C 0.5773(11) 0.4834(5) 0.2380(5) 0.040(3) Uani 1 1 d . . . H18 H 0.5897 0.4853 0.1956 0.048 Uiso 1 1 calc R . . C19 C 0.6507(11) 0.5251(4) 0.2742(4) 0.031(2) Uani 1 1 d . . . C20 C 0.7447(11) 0.5761(4) 0.2534(4) 0.031(3) Uani 1 1 d . . . N21 N 0.7958(9) 0.6146(4) 0.2960(4) 0.036(2) Uani 1 1 d . . . N22 N 0.8804(10) 0.6577(4) 0.2662(4) 0.037(2) Uani 1 1 d . . . H22 H 0.9285 0.6881 0.2839 0.044 Uiso 1 1 calc R . . C23 C 0.8808(11) 0.6475(5) 0.2058(4) 0.036(3) Uani 1 1 d . . . C24 C 0.7952(11) 0.5956(5) 0.1957(5) 0.035(3) Uani 1 1 d . . . H24 H 0.7742 0.5768 0.1581 0.042 Uiso 1 1 calc R . . N25 N 0.9514(10) 0.6862(4) 0.1672(4) 0.048(2) Uani 1 1 d . . . H25A H 0.9986 0.7189 0.1810 0.058 Uiso 1 1 calc R . . H25B H 0.9501 0.6787 0.1284 0.058 Uiso 1 1 calc R . . Br26 Br 0.56922(11) 0.60382(5) 0.46007(4) 0.0366(4) Uani 1 1 d . . . Br27 Br 0.80991(14) 0.32729(5) 0.36080(5) 0.0502(4) Uani 1 1 d . . . O28 O 0.9899(9) 0.7706(4) 0.2928(3) 0.054(2) Uani 1 1 d . . . H28 H 0.9331 0.7945 0.3121 0.064 Uiso 1 1 calc R . . C29 C 1.1419(14) 0.7817(6) 0.3086(5) 0.061(3) Uani 1 1 d . . . H29A H 1.1863 0.8113 0.2805 0.091 Uiso 1 1 calc R . . H29B H 1.1992 0.7432 0.3070 0.091 Uiso 1 1 calc R . . H29C H 1.1462 0.7985 0.3495 0.091 Uiso 1 1 calc R . . 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 0.0347(8) 0.0375(8) 0.0193(7) -0.0058(5) -0.0042(6) 0.0005(6) N2 0.037(5) 0.034(5) 0.008(4) -0.005(3) 0.001(4) 0.001(4) C3 0.046(7) 0.028(6) 0.020(6) -0.004(4) 0.000(5) 0.002(5) C4 0.060(8) 0.035(6) 0.025(6) -0.003(5) 0.006(6) 0.002(6) C5 0.055(8) 0.048(8) 0.028(6) -0.010(5) 0.006(6) -0.010(6) C6 0.036(7) 0.047(7) 0.022(6) -0.006(5) -0.002(5) -0.002(5) C7 0.031(6) 0.036(6) 0.012(5) 0.004(4) 0.009(5) -0.001(5) C8 0.026(6) 0.037(7) 0.013(5) 0.000(4) 0.000(4) 0.000(5) N9 0.040(5) 0.038(5) 0.007(4) 0.002(3) 0.002(4) 0.001(4) N10 0.044(6) 0.031(5) 0.017(5) -0.005(3) -0.003(4) -0.001(4) C11 0.035(7) 0.042(7) 0.015(5) 0.003(4) 0.005(5) 0.008(5) C12 0.026(6) 0.037(6) 0.015(5) -0.004(4) 0.006(4) -0.007(5) N13 0.037(6) 0.046(6) 0.041(6) 0.000(4) 0.002(5) 0.005(5) N14 0.030(5) 0.030(5) 0.028(5) -0.001(4) -0.005(4) 0.003(4) C15 0.047(7) 0.036(6) 0.026(6) -0.001(5) -0.008(5) 0.005(6) C16 0.045(7) 0.047(7) 0.039(7) -0.003(5) -0.006(6) -0.011(6) C17 0.042(7) 0.050(7) 0.040(7) -0.014(6) -0.016(6) -0.004(6) C18 0.038(7) 0.048(7) 0.033(7) -0.016(5) -0.004(5) -0.002(6) C19 0.027(6) 0.039(6) 0.028(6) -0.009(5) -0.004(5) 0.010(5) C20 0.037(6) 0.053(7) 0.005(5) -0.011(5) -0.002(5) 0.008(5) N21 0.038(5) 0.045(6) 0.026(5) -0.009(4) -0.011(4) -0.001(4) N22 0.044(6) 0.038(5) 0.029(5) -0.003(4) -0.001(4) -0.011(4) C23 0.028(6) 0.055(7) 0.025(7) 0.004(5) 0.003(5) 0.012(6) C24 0.037(7) 0.046(7) 0.022(6) -0.004(5) -0.005(5) 0.006(5) N25 0.061(6) 0.055(6) 0.029(5) 0.002(5) 0.012(5) -0.007(5) Br26 0.0343(7) 0.0504(7) 0.0250(6) -0.0059(5) 0.0002(5) 0.0043(5) Br27 0.0620(9) 0.0470(8) 0.0416(8) 0.0003(5) -0.0037(6) -0.0114(6) O28 0.054(5) 0.057(5) 0.050(5) -0.012(4) 0.001(4) -0.004(4) C29 0.072(9) 0.066(9) 0.045(8) -0.003(6) 0.001(7) 0.011(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.996(8) . ? Cu1 N14 1.998(8) . ? Cu1 N21 2.035(9) . ? Cu1 N9 2.089(8) . ? Cu1 Br26 2.5140(16) . ? N2 C3 1.330(12) . ? N2 C7 1.367(12) . ? C3 C4 1.371(14) . ? C3 H3 0.9500 . ? C4 C5 1.381(15) . ? C4 H4 0.9500 . ? C5 C6 1.358(14) . ? C5 H5 0.9500 . ? C6 C7 1.383(13) . ? C6 H6 0.9500 . ? C7 C8 1.470(13) . ? C8 N9 1.339(11) . ? C8 C12 1.403(13) . ? N9 N10 1.361(10) . ? N10 C11 1.367(12) . ? N10 H10 0.8800 . ? C11 C12 1.376(13) . ? C11 N13 1.388(12) . ? C12 H12 0.9500 . ? N13 H13A 0.8800 . ? N13 H13B 0.8800 . ? N14 C15 1.298(12) . ? N14 C19 1.370(11) . ? C15 C16 1.406(14) . ? C15 H15 0.9500 . ? C16 C17 1.376(14) . ? C16 H16 0.9500 . ? C17 C18 1.365(15) . ? C17 H17 0.9500 . ? C18 C19 1.377(13) . ? C18 H18 0.9500 . ? C19 C20 1.460(14) . ? C20 N21 1.344(12) . ? C20 C24 1.425(14) . ? N21 N22 1.369(11) . ? N22 C23 1.363(12) . ? N22 H22 0.8800 . ? C23 N25 1.355(13) . ? C23 C24 1.376(14) . ? C24 H24 0.9500 . ? N25 H25A 0.8800 . ? N25 H25B 0.8800 . ? O28 C29 1.406(13) . ? O28 H28 0.8400 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N14 172.1(3) . . ? N2 Cu1 N21 95.0(3) . . ? N14 Cu1 N21 80.6(3) . . ? N2 Cu1 N9 80.1(3) . . ? N14 Cu1 N9 95.7(3) . . ? N21 Cu1 N9 114.6(3) . . ? N2 Cu1 Br26 92.6(2) . . ? N14 Cu1 Br26 95.2(2) . . ? N21 Cu1 Br26 132.6(2) . . ? N9 Cu1 Br26 112.8(2) . . ? C3 N2 C7 119.0(8) . . ? C3 N2 Cu1 124.8(6) . . ? C7 N2 Cu1 116.2(6) . . ? N2 C3 C4 123.2(9) . . ? N2 C3 H3 118.4 . . ? C4 C3 H3 118.4 . . ? C3 C4 C5 117.5(10) . . ? C3 C4 H4 121.2 . . ? C5 C4 H4 121.2 . . ? C6 C5 C4 120.6(10) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.6(10) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? N2 C7 C6 120.1(9) . . ? N2 C7 C8 114.1(8) . . ? C6 C7 C8 125.8(9) . . ? N9 C8 C12 111.4(8) . . ? N9 C8 C7 116.7(8) . . ? C12 C8 C7 131.9(9) . . ? C8 N9 N10 105.5(7) . . ? C8 N9 Cu1 112.6(6) . . ? N10 N9 Cu1 141.4(6) . . ? N9 N10 C11 110.7(8) . . ? N9 N10 H10 124.6 . . ? C11 N10 H10 124.6 . . ? N10 C11 C12 107.6(8) . . ? N10 C11 N13 120.4(9) . . ? C12 C11 N13 132.0(10) . . ? C11 C12 C8 104.8(8) . . ? C11 C12 H12 127.6 . . ? C8 C12 H12 127.6 . . ? C11 N13 H13A 120.0 . . ? C11 N13 H13B 120.0 . . ? H13A N13 H13B 120.0 . . ? C15 N14 C19 119.0(8) . . ? C15 N14 Cu1 126.3(7) . . ? C19 N14 Cu1 114.7(6) . . ? N14 C15 C16 123.4(10) . . ? N14 C15 H15 118.3 . . ? C16 C15 H15 118.3 . . ? C17 C16 C15 117.3(10) . . ? C17 C16 H16 121.3 . . ? C15 C16 H16 121.3 . . ? C18 C17 C16 119.7(10) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 120.1(10) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? N14 C19 C18 120.5(9) . . ? N14 C19 C20 113.9(8) . . ? C18 C19 C20 125.6(9) . . ? N21 C20 C24 110.2(9) . . ? N21 C20 C19 116.2(8) . . ? C24 C20 C19 133.7(9) . . ? C20 N21 N22 105.6(8) . . ? C20 N21 Cu1 112.9(7) . . ? N22 N21 Cu1 139.6(6) . . ? C23 N22 N21 111.5(8) . . ? C23 N22 H22 124.2 . . ? N21 N22 H22 124.2 . . ? N25 C23 N22 121.7(10) . . ? N25 C23 C24 131.2(10) . . ? N22 C23 C24 107.1(9) . . ? C23 C24 C20 105.6(9) . . ? C23 C24 H24 127.2 . . ? C20 C24 H24 127.2 . . ? C23 N25 H25A 120.0 . . ? C23 N25 H25B 120.0 . . ? H25A N25 H25B 120.0 . . ? C29 O28 H28 109.5 . . ? O28 C29 H29A 109.5 . . ? O28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N10 H10 Br27 0.88 2.43 3.263(8) 158.1 . N13 H13A Br27 0.88 2.90 3.642(9) 142.5 . N13 H13B Br26 0.88 2.76 3.491(9) 141.6 5_766 N22 H22 O28 0.88 1.89 2.708(11) 154.6 . N25 H25A Br27 0.88 3.05 3.776(9) 141.5 4_755 N25 H25B Br26 0.88 2.76 3.510(9) 143.6 6_656 O28 H28 Br27 0.84 2.51 3.287(8) 155.2 7_765 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 22.16 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.943 _refine_diff_density_min -1.356 _refine_diff_density_rms 0.180 #=END data_c:\shared\chris\crysta~1\cp180a\leeds105 _database_code_depnum_ccdc_archive 'CCDC 283227' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis[5-amino-3-(pyrid-2-yl)pyrazole]aquacopper(II) sulfate monohydrate mono-methanol solvate ; _chemical_name_common ; Bis(5-amino-3-(pyrid-2-yl)pyrazole)aquacopper(ii) sulfate monohydrate mono-methanol solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 Cu N8 O, S O4, C H4 O, H2 O' _chemical_formula_sum 'C17 H24 Cu N8 O7 S' _chemical_formula_weight 548.04 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1984(11) _cell_length_b 12.8621(14) _cell_length_c 17.3027(19) _cell_angle_alpha 90.00 _cell_angle_beta 102.705(1) _cell_angle_gamma 90.00 _cell_volume 2214.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4267 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 21.29 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1132 _exptl_absorpt_coefficient_mu 1.139 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.796 _exptl_absorpt_correction_T_max 1.162 _exptl_absorpt_process_details ; Sheldrick, G. M. (2002). SADABS v. 2.03. University of G/ottingen, Germany. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6814 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13828 _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 22.24 _reflns_number_total 3183 _reflns_number_gt 2280 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. No disorder was detected during refinement. All non-H atoms were refined anisotropically, while all H atoms except those on the two water molecules were placed in calculated positions and refined using a riding model. The water H atoms were all located in the Fourier map, and allowed to refine with a common isotropic thermal parameter, subject to the restraints O---H = 0.86(2)\%A and H...H = 1.40(2)\%A. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+5.1877P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3183 _refine_ls_number_parameters 323 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.33430(6) 0.38234(4) 0.63310(3) 0.03278(19) Uani 1 1 d . . . N2 N 0.2473(4) 0.4122(3) 0.7344(2) 0.0317(9) Uani 1 1 d . . . C3 C 0.2850(5) 0.4781(4) 0.7945(3) 0.0370(12) Uani 1 1 d . . . H3 H 0.3655 0.5166 0.7978 0.044 Uiso 1 1 calc R . . C4 C 0.2121(5) 0.4931(4) 0.8522(3) 0.0435(13) Uani 1 1 d . . . H4 H 0.2414 0.5414 0.8940 0.052 Uiso 1 1 calc R . . C5 C 0.0963(5) 0.4364(4) 0.8477(3) 0.0425(13) Uani 1 1 d . . . H5 H 0.0447 0.4452 0.8867 0.051 Uiso 1 1 calc R . . C6 C 0.0555(5) 0.3674(4) 0.7869(3) 0.0366(12) Uani 1 1 d . . . H6 H -0.0246 0.3281 0.7830 0.044 Uiso 1 1 calc R . . C7 C 0.1334(5) 0.3559(3) 0.7314(3) 0.0292(11) Uani 1 1 d . . . C8 C 0.1004(5) 0.2864(3) 0.6631(3) 0.0307(11) Uani 1 1 d . . . N9 N 0.1808(4) 0.2890(3) 0.6125(2) 0.0311(9) Uani 1 1 d . . . N10 N 0.1248(4) 0.2221(3) 0.5524(2) 0.0341(10) Uani 1 1 d . . . H10 H 0.1582 0.2090 0.5106 0.041 Uiso 1 1 calc R . . C11 C 0.0109(5) 0.1790(3) 0.5665(3) 0.0321(11) Uani 1 1 d . . . C12 C -0.0064(5) 0.2172(3) 0.6383(3) 0.0344(12) Uani 1 1 d . . . H12 H -0.0756 0.2002 0.6650 0.041 Uiso 1 1 calc R . . N13 N -0.0653(4) 0.1124(3) 0.5149(2) 0.0433(11) Uani 1 1 d . . . H13A H -0.0415 0.0959 0.4706 0.052 Uiso 1 1 calc R . . H13B H -0.1387 0.0857 0.5256 0.052 Uiso 1 1 calc R . . N14 N 0.2780(4) 0.4676(3) 0.5302(2) 0.0309(9) Uani 1 1 d . . . C15 C 0.1802(5) 0.4485(4) 0.4672(3) 0.0381(12) Uani 1 1 d . . . H15 H 0.1243 0.3898 0.4688 0.046 Uiso 1 1 calc R . . C16 C 0.1552(5) 0.5086(4) 0.3998(3) 0.0431(13) Uani 1 1 d . . . H16 H 0.0850 0.4913 0.3558 0.052 Uiso 1 1 calc R . . C17 C 0.2352(5) 0.5947(4) 0.3983(3) 0.0437(13) Uani 1 1 d . . . H17 H 0.2215 0.6375 0.3524 0.052 Uiso 1 1 calc R . . C18 C 0.3350(5) 0.6182(4) 0.4635(3) 0.0373(12) Uani 1 1 d . . . H18 H 0.3890 0.6784 0.4634 0.045 Uiso 1 1 calc R . . C19 C 0.3562(5) 0.5541(3) 0.5288(3) 0.0301(11) Uani 1 1 d . . . C20 C 0.4624(5) 0.5656(3) 0.5994(3) 0.0305(11) Uani 1 1 d . . . N21 N 0.4735(4) 0.4878(3) 0.6516(2) 0.0353(10) Uani 1 1 d . . . N22 N 0.5789(4) 0.5119(3) 0.7114(2) 0.0408(11) Uani 1 1 d . . . H22 H 0.6073 0.4738 0.7540 0.049 Uiso 1 1 calc R . . C23 C 0.6349(5) 0.6038(4) 0.6959(3) 0.0375(12) Uani 1 1 d . . . C24 C 0.5622(5) 0.6394(4) 0.6250(3) 0.0364(12) Uani 1 1 d . . . H24 H 0.5767 0.7017 0.5986 0.044 Uiso 1 1 calc R . . N25 N 0.7423(4) 0.6437(3) 0.7475(3) 0.0486(12) Uani 1 1 d . . . H25A H 0.7775 0.6099 0.7914 0.058 Uiso 1 1 calc R . . H25B H 0.7769 0.7035 0.7372 0.058 Uiso 1 1 calc R . . O26 O 0.4723(3) 0.2684(2) 0.6794(2) 0.0369(8) Uani 1 1 d D . . H26A H 0.472(6) 0.247(4) 0.726(2) 0.068(10) Uiso 1 1 d D . . H26B H 0.507(5) 0.225(3) 0.653(3) 0.068(10) Uiso 1 1 d D . . S27 S 0.72157(12) 0.40198(9) 0.89105(7) 0.0338(3) Uani 1 1 d . . . O28 O 0.7457(4) 0.3701(3) 0.8146(2) 0.0494(9) Uani 1 1 d . . . O29 O 0.5771(3) 0.3924(3) 0.8899(2) 0.0451(9) Uani 1 1 d . . . O30 O 0.7965(3) 0.3335(3) 0.95486(19) 0.0425(9) Uani 1 1 d . . . O31 O 0.7627(3) 0.5095(2) 0.9090(2) 0.0516(10) Uani 1 1 d . . . O32 O 1.0279(4) 0.3528(3) 1.0661(2) 0.0447(9) Uani 1 1 d D . . H32A H 0.966(4) 0.366(4) 1.025(3) 0.068(10) Uiso 1 1 d D . . H32B H 1.091(4) 0.396(4) 1.071(3) 0.068(10) Uiso 1 1 d D . . O33 O 0.4630(4) 0.2082(3) 0.8281(2) 0.0441(9) Uani 1 1 d . . . H33 H 0.5040 0.2597 0.8518 0.053 Uiso 1 1 calc R . . C34 C 0.3547(5) 0.1816(4) 0.8630(3) 0.0498(14) Uani 1 1 d . . . H34A H 0.3853 0.1314 0.9058 0.075 Uiso 1 1 calc R . . H34B H 0.2823 0.1507 0.8229 0.075 Uiso 1 1 calc R . . H34C H 0.3213 0.2443 0.8846 0.075 Uiso 1 1 calc R . . 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 0.0386(4) 0.0234(3) 0.0362(4) 0.0027(3) 0.0079(3) -0.0068(3) N2 0.035(2) 0.021(2) 0.038(2) 0.0021(18) 0.0071(19) 0.0008(18) C3 0.038(3) 0.029(3) 0.045(3) 0.001(2) 0.010(2) 0.000(2) C4 0.057(4) 0.029(3) 0.045(3) -0.009(2) 0.012(3) 0.002(3) C5 0.045(3) 0.038(3) 0.048(3) -0.003(3) 0.018(3) 0.006(3) C6 0.036(3) 0.028(3) 0.049(3) 0.003(2) 0.014(2) 0.002(2) C7 0.035(3) 0.019(2) 0.033(3) 0.003(2) 0.007(2) 0.000(2) C8 0.034(3) 0.018(2) 0.041(3) 0.006(2) 0.010(2) 0.003(2) N9 0.037(2) 0.022(2) 0.035(2) -0.0024(18) 0.009(2) -0.0043(18) N10 0.042(3) 0.025(2) 0.036(2) -0.0005(18) 0.010(2) -0.0014(19) C11 0.032(3) 0.021(2) 0.043(3) 0.005(2) 0.008(2) -0.004(2) C12 0.036(3) 0.022(3) 0.049(3) 0.005(2) 0.016(2) -0.001(2) N13 0.048(3) 0.031(2) 0.054(3) -0.009(2) 0.018(2) -0.013(2) N14 0.035(2) 0.021(2) 0.037(2) 0.0028(17) 0.010(2) 0.0021(18) C15 0.041(3) 0.028(3) 0.044(3) 0.001(2) 0.008(3) 0.004(2) C16 0.044(3) 0.034(3) 0.047(3) 0.007(2) 0.000(3) 0.005(3) C17 0.054(3) 0.033(3) 0.043(3) 0.014(2) 0.008(3) 0.015(3) C18 0.038(3) 0.025(3) 0.051(3) 0.004(3) 0.016(3) 0.003(2) C19 0.034(3) 0.021(2) 0.038(3) 0.003(2) 0.016(2) 0.007(2) C20 0.037(3) 0.018(2) 0.040(3) 0.000(2) 0.016(2) 0.000(2) N21 0.040(3) 0.029(2) 0.035(2) 0.0002(19) 0.005(2) -0.0081(19) N22 0.050(3) 0.038(3) 0.031(2) 0.0036(19) 0.001(2) -0.013(2) C23 0.037(3) 0.033(3) 0.045(3) -0.001(2) 0.014(3) -0.007(2) C24 0.045(3) 0.023(3) 0.046(3) 0.001(2) 0.018(3) -0.007(2) N25 0.050(3) 0.047(3) 0.047(3) 0.002(2) 0.005(2) -0.022(2) O26 0.043(2) 0.0270(19) 0.042(2) 0.0020(16) 0.0119(19) 0.0042(16) S27 0.0340(7) 0.0288(7) 0.0391(7) -0.0005(5) 0.0090(6) 0.0017(5) O28 0.055(2) 0.057(2) 0.039(2) 0.0040(18) 0.0152(18) 0.0113(19) O29 0.036(2) 0.046(2) 0.055(2) -0.0114(18) 0.0133(17) -0.0034(17) O30 0.044(2) 0.037(2) 0.045(2) 0.0063(16) 0.0069(17) 0.0077(16) O31 0.045(2) 0.0251(19) 0.085(3) -0.0065(18) 0.017(2) -0.0060(16) O32 0.050(2) 0.028(2) 0.054(2) 0.0037(17) 0.0067(19) -0.0071(17) O33 0.056(2) 0.029(2) 0.048(2) -0.0013(16) 0.0128(19) -0.0057(17) C34 0.051(4) 0.040(3) 0.060(4) 0.002(3) 0.016(3) -0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N21 1.939(4) . ? Cu1 N9 1.942(4) . ? Cu1 N14 2.063(4) . ? Cu1 O26 2.068(3) . ? Cu1 N2 2.166(4) . ? N2 C3 1.330(6) . ? N2 C7 1.360(6) . ? C3 C4 1.384(7) . ? C3 H3 0.9500 . ? C4 C5 1.375(7) . ? C4 H4 0.9500 . ? C5 C6 1.370(7) . ? C5 H5 0.9500 . ? C6 C7 1.383(6) . ? C6 H6 0.9500 . ? C7 C8 1.461(6) . ? C8 N9 1.325(6) . ? C8 C12 1.399(6) . ? N9 N10 1.373(5) . ? N10 C11 1.357(6) . ? N10 H10 0.8800 . ? C11 N13 1.352(6) . ? C11 C12 1.382(6) . ? C12 H12 0.9500 . ? N13 H13A 0.8800 . ? N13 H13B 0.8800 . ? N14 C15 1.328(6) . ? N14 C19 1.372(6) . ? C15 C16 1.375(7) . ? C15 H15 0.9500 . ? C16 C17 1.380(7) . ? C16 H16 0.9500 . ? C17 C18 1.377(7) . ? C17 H17 0.9500 . ? C18 C19 1.377(6) . ? C18 H18 0.9500 . ? C19 C20 1.451(6) . ? C20 N21 1.336(6) . ? C20 C24 1.391(6) . ? N21 N22 1.353(5) . ? N22 C23 1.365(6) . ? N22 H22 0.8800 . ? C23 N25 1.353(6) . ? C23 C24 1.365(7) . ? C24 H24 0.9500 . ? N25 H25B 0.8800 . ? N25 H25A 0.8800 . ? O26 H26A 0.85(3) . ? O26 H26B 0.85(3) . ? S27 O28 1.456(3) . ? S27 O31 1.459(3) . ? S27 O29 1.474(3) . ? S27 O30 1.486(3) . ? O32 H32A 0.86(3) . ? O32 H32B 0.84(3) . ? O33 C34 1.413(6) . ? O33 H33 0.8400 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N21 Cu1 N9 173.76(16) . . ? N21 Cu1 N14 79.94(16) . . ? N9 Cu1 N14 96.30(15) . . ? N21 Cu1 O26 91.18(15) . . ? N9 Cu1 O26 94.91(14) . . ? N14 Cu1 O26 138.46(14) . . ? N21 Cu1 N2 99.08(15) . . ? N9 Cu1 N2 78.54(15) . . ? N14 Cu1 N2 121.22(14) . . ? O26 Cu1 N2 100.19(13) . . ? C3 N2 C7 117.8(4) . . ? C3 N2 Cu1 130.2(3) . . ? C7 N2 Cu1 111.9(3) . . ? N2 C3 C4 123.0(5) . . ? N2 C3 H3 118.5 . . ? C4 C3 H3 118.5 . . ? C5 C4 C3 118.4(5) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? C6 C5 C4 120.0(5) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 118.6(5) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? N2 C7 C6 122.2(4) . . ? N2 C7 C8 113.6(4) . . ? C6 C7 C8 124.2(4) . . ? N9 C8 C12 111.5(4) . . ? N9 C8 C7 116.9(4) . . ? C12 C8 C7 131.5(4) . . ? C8 N9 N10 105.6(4) . . ? C8 N9 Cu1 119.0(3) . . ? N10 N9 Cu1 135.3(3) . . ? C11 N10 N9 110.5(4) . . ? C11 N10 H10 124.8 . . ? N9 N10 H10 124.8 . . ? N13 C11 N10 122.0(4) . . ? N13 C11 C12 130.5(4) . . ? N10 C11 C12 107.4(4) . . ? C11 C12 C8 104.9(4) . . ? C11 C12 H12 127.6 . . ? C8 C12 H12 127.6 . . ? C11 N13 H13A 120.0 . . ? C11 N13 H13B 120.0 . . ? H13A N13 H13B 120.0 . . ? C15 N14 C19 118.1(4) . . ? C15 N14 Cu1 128.8(3) . . ? C19 N14 Cu1 113.2(3) . . ? N14 C15 C16 123.9(5) . . ? N14 C15 H15 118.1 . . ? C16 C15 H15 118.1 . . ? C15 C16 C17 117.9(5) . . ? C15 C16 H16 121.1 . . ? C17 C16 H16 121.1 . . ? C18 C17 C16 119.6(5) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C19 C18 C17 119.7(5) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? N14 C19 C18 120.9(4) . . ? N14 C19 C20 113.4(4) . . ? C18 C19 C20 125.7(4) . . ? N21 C20 C24 110.4(4) . . ? N21 C20 C19 115.4(4) . . ? C24 C20 C19 134.1(4) . . ? C20 N21 N22 106.3(4) . . ? C20 N21 Cu1 117.5(3) . . ? N22 N21 Cu1 135.7(3) . . ? N21 N22 C23 110.1(4) . . ? N21 N22 H22 124.9 . . ? C23 N22 H22 124.9 . . ? N25 C23 C24 131.8(5) . . ? N25 C23 N22 120.8(5) . . ? C24 C23 N22 107.4(4) . . ? C23 C24 C20 105.8(4) . . ? C23 C24 H24 127.1 . . ? C20 C24 H24 127.1 . . ? C23 N25 H25B 120.0 . . ? C23 N25 H25A 120.0 . . ? H25B N25 H25A 120.0 . . ? Cu1 O26 H26A 117(3) . . ? Cu1 O26 H26B 126(3) . . ? H26A O26 H26B 112(3) . . ? O28 S27 O31 111.2(2) . . ? O28 S27 O29 109.4(2) . . ? O31 S27 O29 108.8(2) . . ? O28 S27 O30 110.2(2) . . ? O31 S27 O30 109.1(2) . . ? O29 S27 O30 108.0(2) . . ? H32A O32 H32B 112(3) . . ? C34 O33 H33 109.5 . . ? O33 C34 H34A 109.5 . . ? O33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N10 H10 O30 0.88 1.95 2.779(5) 155.5 4_565 N13 H13A O29 0.88 2.04 2.858(5) 153.6 4_565 N13 H13B O31 0.88 2.11 2.950(5) 158.6 2_546 N22 H22 O28 0.88 2.05 2.841(5) 148.4 . N25 H25A O31 0.88 2.44 3.251(6) 153.0 . N25 H25B O28 0.88 2.32 3.116(6) 151.2 2_656 O26 H26A O33 0.85(3) 1.86(3) 2.707(5) 175(5) . O26 H26B O32 0.85(3) 1.85(3) 2.662(5) 158(5) 4_565 O32 H32A O30 0.86(3) 1.93(3) 2.708(5) 151(5) . O32 H32B O31 0.84(3) 1.89(3) 2.735(5) 176(5) 3_767 O33 H33 O29 0.84 1.92 2.750(5) 169.0 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 22.24 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.395 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.069