Electronic Supplementary Information for Dalton Transactions This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Jonathan Dilworth' _publ_contact_author_address ; Department of Inorganic Chemistry University of Oxford Chemistry Research Laboratory 12 Mansfield Road Oxford OX13TA UNITED KINGDOM ; _publ_contact_author_email JON.DILWORTH@CHEM.OX.AC.UK _publ_section_title ; Bifunctional chelators for copper radiopharmaceuticals: The synthesis of [Cu(ATSM)-amino acid] and [Cu(ATSM)-octreotide] conjugates. ; loop_ _publ_author_name 'J. R. Dilworth' 'Andrew R. Cowley' 'Paul Donnelly' 'Julia M. Heslop' 'Steven J. Ratcliffe' data_ARC698 _database_code_depnum_ccdc_archive 'CCDC 263392' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; Geometric restraints were applied to the disordered solvent molecule O5-C20. O-C bond lengths were restrained to 1.44(2) \%A and C-C bond lengths to 1.48(2) \%A. C-O-C and O-C-C angles were restrained to 112(2) \%. OH and NH hydrogen atoms were located in a difference Fourier map and their coordinates and isotropic thermal parameters subsequently refined. Other hydrogen atoms were positioned geometrically, the orientations of the methyl groups having been determined previously by examination of the difference Fourier map ; #============================================================= _cell_length_a 7.7954(2) _cell_angle_alpha 68.0679(11) _cell_length_b 12.1336(3) _cell_angle_beta 88.8912(9) _cell_length_c 12.5220(3) _cell_angle_gamma 86.7614(11) _cell_volume 1096.93(5) _symmetry_cell_setting 'Triclinic ' _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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 ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'S ' 0.1100 0.1240 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C36 H58 N10 O9 S2 ' _chemical_formula_moiety ' C20 H20 N6 O4 S2, 4(C3 H7 N O), C4 H10 O ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 839.04 _cell_measurement_reflns_used 14644 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 1 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' pale orange ' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_max 0.38 _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_meas ? _exptl_crystal_F_000 448.313 _exptl_absorpt_coefficient_mu 0.183 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 14644 _reflns_number_total 4989 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_gt 4903 _diffrn_reflns_theta_min 5.16 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_theta_full 27.46 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -10 _reflns_limit_h_max 9 _reflns_limit_k_min -15 _reflns_limit_k_max 15 _reflns_limit_l_min -16 _reflns_limit_l_max 15 _refine_diff_density_min -0.70 _refine_diff_density_max 0.76 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 4903 _refine_ls_number_parameters 267 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.0777 _refine_ls_goodness_of_fit_ref 1.0308 _refine_ls_shift/su_max 0.030205 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 1.77 1.23 1.16 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _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 S1 0.02978(7) 0.70925(6) 0.20441(5) 0.0699 1.0000 Uani C1 -0.0767(2) 0.65951(19) 0.32874(18) 0.0530 1.0000 Uani N1 -0.2264(2) 0.60379(17) 0.33458(16) 0.0558 1.0000 Uani N2 -0.31229(19) 0.56469(16) 0.43709(14) 0.0530 1.0000 Uani C2 -0.4601(2) 0.51913(19) 0.44234(18) 0.0528 1.0000 Uani N3 -0.0361(2) 0.66943(17) 0.42918(16) 0.0556 1.0000 Uani C3 0.1039(2) 0.71615(19) 0.46486(19) 0.0529 1.0000 Uani C4 0.2416(3) 0.7682(2) 0.3953(2) 0.0608 1.0000 Uani C5 0.3752(3) 0.8048(2) 0.4440(2) 0.0656 1.0000 Uani C6 0.3735(3) 0.7934(2) 0.5574(2) 0.0636 1.0000 Uani C7 0.2324(3) 0.7444(2) 0.6253(2) 0.0708 1.0000 Uani C8 0.0990(3) 0.7069(2) 0.5786(2) 0.0646 1.0000 Uani C9 0.5254(3) 0.8274(2) 0.6067(3) 0.0772 1.0000 Uani O1 0.6572(3) 0.8569(2) 0.5532(2) 0.1118 1.0000 Uani O2 0.5053(3) 0.8195(2) 0.71330(19) 0.0883 1.0000 Uani C10 -0.5510(2) 0.5040(2) 0.3457(2) 0.0658 1.0000 Uani O3 -0.2791(2) 0.52602(18) 0.14836(15) 0.0820 1.0000 Uani C11 -0.2267(3) 0.5714(2) 0.0489(2) 0.0655 1.0000 Uani N4 -0.2307(2) 0.52169(18) -0.02881(16) 0.0615 1.0000 Uani C12 -0.1704(3) 0.5811(3) -0.1458(2) 0.0800 1.0000 Uani C13 -0.3015(3) 0.4064(3) -0.0017(2) 0.0794 1.0000 Uani O4 0.7773(3) 0.8734(2) 0.7963(2) 0.1096 1.0000 Uani C14 0.8893(4) 0.9268(3) 0.7277(3) 0.0860 1.0000 Uani N5 1.0312(3) 0.95938(19) 0.7624(2) 0.0860 1.0000 Uani C15 1.1577(4) 1.0226(3) 0.6811(3) 0.1011 1.0000 Uani C16 1.0644(6) 0.9367(4) 0.8816(4) 0.1327 1.0000 Uani O5 0.4756(9) -0.0039(8) -0.0151(8) 0.152(2) 0.5000 Uiso C17 0.4389(9) 0.1185(8) -0.0311(8) 0.142(3) 0.5000 Uiso C18 0.4739(9) 0.1767(9) -0.1522(8) 0.129(3) 0.5000 Uiso C19 0.4514(9) -0.0763(8) 0.1046(8) 0.142(3) 0.5000 Uiso C20 0.499(1) -0.1944(9) 0.104(1) 0.145(3) 0.5000 Uiso H1 -0.260(3) 0.5928(18) 0.274(2) 0.056(6) 1.0000 Uiso H2 -0.107(3) 0.6424(19) 0.484(2) 0.053(6) 1.0000 Uiso H3 0.591(5) 0.835(3) 0.734(3) 0.131(14) 1.0000 Uiso H41 0.2443 0.7790 0.3121 0.0763 1.0000 Uiso H51 0.4757 0.8406 0.3949 0.0810 1.0000 Uiso H71 0.2278 0.7364 0.7077 0.0902 1.0000 Uiso H81 -0.0024 0.6726 0.6274 0.0820 1.0000 Uiso H101 -0.6625 0.4665 0.3739 0.0868 1.0000 Uiso H102 -0.5736 0.5835 0.2828 0.0868 1.0000 Uiso H103 -0.4779 0.4518 0.3154 0.0868 1.0000 Uiso H111 -0.1776 0.6514 0.0252 0.0861 1.0000 Uiso H121 -0.1247 0.6592 -0.1540 0.0992 1.0000 Uiso H122 -0.2678 0.5947 -0.2008 0.0992 1.0000 Uiso H123 -0.0771 0.5302 -0.1630 0.0992 1.0000 Uiso H131 -0.3384 0.3746 0.0807 0.1054 1.0000 Uiso H132 -0.4029 0.4148 -0.0524 0.1054 1.0000 Uiso H133 -0.2121 0.3503 -0.0147 0.1054 1.0000 Uiso H141 0.8722 0.9459 0.6436 0.1027 1.0000 Uiso H151 1.1212 1.0331 0.6016 0.1221 1.0000 Uiso H152 1.1693 1.1023 0.6857 0.1221 1.0000 Uiso H153 1.2708 0.9763 0.6994 0.1221 1.0000 Uiso H161 0.9683 0.8925 0.9298 0.1541 1.0000 Uiso H162 1.0733 1.0140 0.8920 0.1541 1.0000 Uiso H163 1.1747 0.8879 0.9057 0.1541 1.0000 Uiso H171 0.5162 0.1446 0.0168 0.1703 0.5000 Uiso H172 0.3164 0.1333 -0.0128 0.1703 0.5000 Uiso H181 0.4529 0.2647 -0.1752 0.1546 0.5000 Uiso H182 0.5964 0.1586 -0.1678 0.1546 0.5000 Uiso H183 0.3965 0.1473 -0.1974 0.1546 0.5000 Uiso H191 0.5286 -0.0543 0.1555 0.1699 0.5000 Uiso H192 0.3294 -0.0706 0.1289 0.1699 0.5000 Uiso H201 0.4884 -0.2551 0.1841 0.1735 0.5000 Uiso H202 0.6210 -0.1964 0.0779 0.1735 0.5000 Uiso H203 0.4217 -0.2126 0.0512 0.1735 0.5000 Uiso 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 S1 0.0542(3) 0.1113(5) 0.0612(4) -0.0494(3) 0.0103(2) -0.0247(3) C1 0.0440(9) 0.0684(13) 0.0569(12) -0.035(1) -0.0007(8) -0.0054(9) N1 0.0447(8) 0.0839(13) 0.054(1) -0.043(1) 0.0042(7) -0.0138(8) N2 0.0388(7) 0.0787(12) 0.055(1) -0.0400(9) 0.0015(7) -0.0078(7) C2 0.0388(9) 0.0763(13) 0.0584(12) -0.0419(11) 0.0002(8) -0.0062(9) N3 0.0454(8) 0.0788(12) 0.054(1) -0.0360(9) 0.0033(7) -0.0179(8) C3 0.0449(9) 0.0640(13) 0.0586(12) -0.032(1) -0.0049(8) -0.0068(8) C4 0.054(1) 0.0776(14) 0.0594(13) -0.0330(11) -0.0003(9) -0.018(1) C5 0.0514(11) 0.0799(15) 0.0713(15) -0.0327(12) -0.002(1) -0.019(1) C6 0.0539(11) 0.0706(14) 0.0721(15) -0.0318(12) -0.014(1) -0.010(1) C7 0.0615(12) 0.0990(18) 0.0650(14) -0.0437(13) -0.0077(11) -0.0155(12) C8 0.0522(11) 0.0912(16) 0.0616(13) -0.0396(12) -0.0005(9) -0.018(1) C9 0.0635(14) 0.0908(18) 0.0854(19) -0.0399(15) -0.0187(13) -0.0141(12) O1 0.0742(12) 0.175(2) 0.1074(17) -0.0694(16) -0.0014(11) -0.0557(13) O2 0.0741(11) 0.1203(16) 0.0821(14) -0.0473(11) -0.021(1) -0.0253(11) C10 0.047(1) 0.1099(19) 0.0604(13) -0.0528(13) 0.0038(9) -0.0165(11) O3 0.074(1) 0.1324(15) 0.0678(11) -0.0662(11) 0.0176(8) -0.036(1) C11 0.0507(11) 0.1025(18) 0.0621(14) -0.0508(13) 0.002(1) -0.0140(11) N4 0.0488(9) 0.0957(14) 0.055(1) -0.044(1) -0.0006(7) -0.0092(9) C12 0.0801(15) 0.112(2) 0.0553(14) -0.0408(14) -0.0022(12) -0.0020(14) C13 0.0697(14) 0.115(2) 0.0789(17) -0.0630(16) 0.0106(12) -0.0240(14) O4 0.1167(16) 0.1165(17) 0.0975(16) -0.0352(13) -0.0359(13) -0.0447(14) C14 0.0902(18) 0.0739(17) 0.093(2) -0.0265(15) -0.0276(16) -0.0185(14) N5 0.0983(16) 0.0662(13) 0.0904(17) -0.0220(11) -0.0345(13) -0.0178(11) C15 0.096(2) 0.0788(19) 0.131(3) -0.0401(19) -0.0141(19) -0.0088(16) C16 0.161(3) 0.119(3) 0.105(3) -0.017(2) -0.060(2) -0.060(2) _refine_ls_extinction_method None 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 S1 . C1 . 1.668(2) yes C1 . N1 . 1.369(2) yes C1 . N3 . 1.352(3) yes N1 . N2 . 1.367(2) yes N1 . H1 . 0.87(2) yes N2 . C2 . 1.296(2) yes C2 . C2 2_466 1.478(4) yes C2 . C10 . 1.488(3) yes N3 . C3 . 1.410(2) yes N3 . H2 . 0.84(2) yes C3 . C4 . 1.392(3) yes C3 . C8 . 1.386(3) yes C4 . C5 . 1.390(3) yes C4 . H41 . 1.000 no C5 . C6 . 1.375(3) yes C5 . H51 . 1.000 no C6 . C7 . 1.395(3) yes C6 . C9 . 1.491(3) yes C7 . C8 . 1.380(3) yes C7 . H71 . 1.000 no C8 . H81 . 1.000 no C9 . O1 . 1.212(3) yes C9 . O2 . 1.310(3) yes O2 . H3 . 0.78(4) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C10 . H103 . 1.000 no O3 . C11 . 1.230(3) yes C11 . N4 . 1.324(3) yes C11 . H111 . 1.000 no N4 . C12 . 1.452(3) yes N4 . C13 . 1.450(3) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no O4 . C14 . 1.240(4) yes C14 . N5 . 1.329(3) yes C14 . H141 . 1.000 no N5 . C15 . 1.435(4) yes N5 . C16 . 1.438(4) yes C15 . H151 . 1.000 no C15 . H152 . 1.000 no C15 . H153 . 1.000 no C16 . H161 . 1.000 no C16 . H162 . 1.000 no C16 . H163 . 1.000 no O5 . C17 . 1.435(12) yes O5 . C19 . 1.441(12) yes C17 . C18 . 1.441(11) yes C17 . H171 . 1.000 no C17 . H172 . 1.000 no C18 . H181 . 1.00 no C18 . H182 . 1.000 no C18 . H183 . 1.000 no C19 . C20 . 1.461(11) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.00 no 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 S1 . C1 . N1 . 119.27(15) yes S1 . C1 . N3 . 127.80(15) yes N1 . C1 . N3 . 112.92(17) yes C1 . N1 . N2 . 118.26(17) yes C1 . N1 . H1 . 118.5(14) yes N2 . N1 . H1 . 123.2(14) yes N1 . N2 . C2 . 119.18(16) yes N2 . C2 . C2 2_466 113.9(2) yes N2 . C2 . C10 . 126.38(18) yes C2 2_466 C2 . C10 . 119.74(19) yes C1 . N3 . C3 . 133.32(18) yes C1 . N3 . H2 . 116.0(15) yes C3 . N3 . H2 . 110.7(15) yes N3 . C3 . C4 . 124.96(19) yes N3 . C3 . C8 . 115.30(18) yes C4 . C3 . C8 . 119.74(18) yes C3 . C4 . C5 . 118.6(2) yes C3 . C4 . H41 . 120.69 no C5 . C4 . H41 . 120.7 no C4 . C5 . C6 . 122.1(2) yes C4 . C5 . H51 . 119.0 no C6 . C5 . H51 . 119.0 no C5 . C6 . C7 . 118.7(2) yes C5 . C6 . C9 . 119.6(2) yes C7 . C6 . C9 . 121.6(2) yes C6 . C7 . C8 . 120.0(2) yes C6 . C7 . H71 . 120.0 no C8 . C7 . H71 . 120.0 no C3 . C8 . C7 . 120.8(2) yes C3 . C8 . H81 . 119.6 no C7 . C8 . H81 . 119.6 no C6 . C9 . O1 . 122.6(3) yes C6 . C9 . O2 . 114.2(2) yes O1 . C9 . O2 . 123.1(2) yes C9 . O2 . H3 . 108.(3) yes C2 . C10 . H101 . 109.47 no C2 . C10 . H102 . 109.47 no H101 . C10 . H102 . 109.5 no C2 . C10 . H103 . 109.47 no H101 . C10 . H103 . 109.5 no H102 . C10 . H103 . 109.5 no O3 . C11 . N4 . 124.6(2) yes O3 . C11 . H111 . 117.7 no N4 . C11 . H111 . 117.7 no C11 . N4 . C12 . 122.0(2) yes C11 . N4 . C13 . 121.15(19) yes C12 . N4 . C13 . 116.81(19) yes N4 . C12 . H121 . 109.5 no N4 . C12 . H122 . 109.5 no H121 . C12 . H122 . 109.5 no N4 . C12 . H123 . 109.5 no H121 . C12 . H123 . 109.5 no H122 . C12 . H123 . 109.5 no N4 . C13 . H131 . 109.5 no N4 . C13 . H132 . 109.5 no H131 . C13 . H132 . 109.5 no N4 . C13 . H133 . 109.5 no H131 . C13 . H133 . 109.5 no H132 . C13 . H133 . 109.5 no O4 . C14 . N5 . 122.1(3) yes O4 . C14 . H141 . 118.9 no N5 . C14 . H141 . 118.9 no C14 . N5 . C15 . 121.0(3) yes C14 . N5 . C16 . 122.4(3) yes C15 . N5 . C16 . 116.6(3) yes N5 . C15 . H151 . 109.5 no N5 . C15 . H152 . 109.5 no H151 . C15 . H152 . 109.5 no N5 . C15 . H153 . 109.5 no H151 . C15 . H153 . 109.5 no H152 . C15 . H153 . 109.5 no N5 . C16 . H161 . 109.5 no N5 . C16 . H162 . 109.5 no H161 . C16 . H162 . 109.5 no N5 . C16 . H163 . 109.5 no H161 . C16 . H163 . 109.5 no H162 . C16 . H163 . 109.5 no C17 . O5 . C19 . 108.7(7) yes O5 . C17 . C18 . 101.2(7) yes O5 . C17 . H171 . 111.5 no C18 . C17 . H171 . 111.5 no O5 . C17 . H172 . 111.5 no C18 . C17 . H172 . 111.5 no H171 . C17 . H172 . 109.5 no C17 . C18 . H181 . 109.5 no C17 . C18 . H182 . 109.5 no H181 . C18 . H182 . 109.5 no C17 . C18 . H183 . 109.5 no H181 . C18 . H183 . 109.5 no H182 . C18 . H183 . 109.5 no O5 . C19 . C20 . 100.7(8) yes O5 . C19 . H191 . 111.6 no C20 . C19 . H191 . 111.6 no O5 . C19 . H192 . 111.6 no C20 . C19 . H192 . 111.6 no H191 . C19 . H192 . 109.5 no C19 . C20 . H201 . 109.5 no C19 . C20 . H202 . 109.5 no C19 . C20 . H203 . 109.5 no H201 . C20 . H202 . 109.5 no H201 . C20 . H203 . 109.5 no H202 . C20 . H203 . 109.5 no 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_publ_flag N1 H1 O3 0.87(2) 2.03(2) 2.867(2) 161.7(19) yes O2 H3 O4 0.78(4) 1.82(4) 2.598(3) 173.(4) yes # Attachment 'arc994.cif' data_arc994 _database_code_depnum_ccdc_archive 'CCDC 263393' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; Geometric restraints were applied to the disordered solvent molecule O4-C20. The O-C distance was restrained to 1.25(2) \%A, The C(carbonyl)-N distance to 1.35(2) \%A and the N-C(methyl) distances to 1.45(2) \%A. Vibrational similarity restraints were applied to directly-bonded pairs of atoms The NH and OH hydrogen atoms were located in a difference Fourier map and their coordinates and isotropic displacement parameters subsequently refined. All other hydrogens were positioned geometrically, the preferred orientations of the methyl groups having been previously identified by examination of the Fourier map. ; #============================================================= _cell_length_a 27.3837(4) _cell_angle_alpha 90 _cell_length_b 7.2624(2) _cell_angle_beta 119.6043(8) _cell_length_c 27.4189(4) _cell_angle_gamma 90 _cell_volume 4741.01(17) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 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_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B 'Ni ' 0.3393 1.1124 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421 1.0341 International_Tables_Vol_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B _cell_formula_units_Z 8 _chemical_formula_sum ' C18.50 H26.50 N7.50 Ni O3.50 S2 ' _chemical_formula_moiety ' C14 H16 N6 Ni O2 S2, 1.5(C3 H7 N O)' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 532.80 _cell_measurement_reflns_used 37798 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' brown ' _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_max 0.24 _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 2224 _exptl_absorpt_coefficient_mu 1.033 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.96 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 37798 _reflns_number_total 5406 #5823 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.068 _diffrn_reflns_theta_min 5.120 _diffrn_reflns_theta_max 27.476 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.476 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _reflns_limit_h_min -35 _reflns_limit_h_max 30 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 35 _refine_diff_density_min -0.34 _refine_diff_density_max 0.35 _refine_ls_number_reflns 3455 _refine_ls_number_restraints 32 _refine_ls_number_parameters 328 #_refine_ls_R_factor_ref 0.0320 _refine_ls_wR_factor_ref 0.0358 _refine_ls_goodness_of_fit_ref 1.0999 #_reflns_number_all 5406 _refine_ls_R_factor_all 0.0662 _refine_ls_wR_factor_all 0.0557 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 3455 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_gt 0.0358 _refine_ls_shift/su_max 0.029754 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _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: 0.545 0.316 0.330 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_refinement_disorder_assembly _atom_site_refinement_disorder_group Ni1 Ni 0.316656(13) 0.57283(4) 0.545239(13) 0.0217 1.0000 Uani . . . . . S1 S 0.34227(3) 0.63462(9) 0.48428(2) 0.0249 1.0000 Uani . . . . . C1 C 0.27708(10) 0.5737(4) 0.4261(1) 0.0220 1.0000 Uani . . . . . N1 N 0.23408(9) 0.5131(3) 0.42986(8) 0.0245 1.0000 Uani . . . . . N2 N 0.24772(9) 0.5041(3) 0.48554(8) 0.0225 1.0000 Uani . . . . . C2 C 0.21043(10) 0.4480(3) 0.49867(10) 0.0239 1.0000 Uani . . . . . C3 C 0.23216(10) 0.4486(3) 0.55972(10) 0.0234 1.0000 Uani . . . . . N3 N 0.28389(9) 0.5084(3) 0.58809(8) 0.0235 1.0000 Uani . . . . . N4 N 0.31001(9) 0.5228(3) 0.64553(9) 0.0263 1.0000 Uani . . . . . C4 C 0.36177(11) 0.5827(4) 0.66521(10) 0.0268 1.0000 Uani . . . . . S2 S 0.39177(3) 0.63497(10) 0.62264(3) 0.0288 1.0000 Uani . . . . . N5 N 0.27466(9) 0.5888(3) 0.37550(9) 0.0259 1.0000 Uani . . . . . C5 C 0.23271(11) 0.5302(3) 0.32259(10) 0.0234 1.0000 Uani . . . . . C6 C 0.24864(11) 0.5102(4) 0.28138(11) 0.0274 1.0000 Uani . . . . . C7 C 0.21047(11) 0.4518(4) 0.22795(10) 0.0269 1.0000 Uani . . . . . C8 C 0.15532(10) 0.4139(4) 0.21393(10) 0.0247 1.0000 Uani . . . . . C9 C 0.13896(11) 0.4363(4) 0.25455(11) 0.0278 1.0000 Uani . . . . . C10 C 0.17747(11) 0.4923(4) 0.30884(10) 0.0273 1.0000 Uani . . . . . C11 C 0.11494(11) 0.3474(4) 0.15677(11) 0.0274 1.0000 Uani . . . . . O1 O 0.13023(8) 0.2853(3) 0.12478(7) 0.0336 1.0000 Uani . . . . . O2 O 0.06178(8) 0.3611(3) 0.14292(9) 0.0404 1.0000 Uani . . . . . C12 C 0.15202(11) 0.3939(4) 0.45670(11) 0.0289 1.0000 Uani . . . . . C13 C 0.19827(12) 0.3857(4) 0.58578(11) 0.0310 1.0000 Uani . . . . . N6 N 0.39490(11) 0.6058(4) 0.72030(9) 0.0323 1.0000 Uani . . . . . C14 C 0.37491(13) 0.5757(4) 0.76009(11) 0.0361 1.0000 Uani . . . . . O3 O -0.00506(8) 0.2698(3) 0.04057(8) 0.0431 1.0000 Uani . . . . . C15 C 0.01373(11) 0.2654(5) 0.00783(12) 0.0373 1.0000 Uani . . . . . N7 N -0.01553(9) 0.2203(4) -0.04559(9) 0.0332 1.0000 Uani . . . . . C16 C 0.00979(13) 0.2186(6) -0.08172(13) 0.0480 1.0000 Uani . . . . . C17 C -0.07407(12) 0.1665(5) -0.07120(12) 0.0415 1.0000 Uani . . . . . O4 O 0.4963(19) 0.8017(5) 0.7506(15) 0.0413 0.5000 Uani D U . 1 -1 C18 C 0.5135(2) 0.9467(9) 0.7780(2) 0.0373 0.5000 Uani D U . 1 -1 N8 N 0.4975(7) 1.1128(6) 0.7554(4) 0.0365 0.5000 Uani D U . 1 -1 C19 C 0.5156(3) 1.2776(10) 0.7900(3) 0.0549 0.5000 Uani D U . 1 -1 C20 C 0.4621(3) 1.1324(11) 0.6947(3) 0.0466 0.5000 Uani D U . 1 -1 H1 H 0.3015(12) 0.631(4) 0.3760(11) 0.022(7) 1.0000 Uiso . . . . . H2 H 0.0408(17) 0.328(6) 0.1097(18) 0.068(13) 1.0000 Uiso . . . . . H3 H 0.4254(15) 0.657(5) 0.7331(14) 0.037(9) 1.0000 Uiso . . . . . H61 H 0.2881 0.5386 0.2909 0.0345 1.0000 Uiso . . . . . H71 H 0.2226 0.4368 0.1992 0.0337 1.0000 Uiso . . . . . H91 H 0.0991 0.4119 0.2445 0.0353 1.0000 Uiso . . . . . H101 H 0.1655 0.5051 0.3378 0.0334 1.0000 Uiso . . . . . H121 H 0.1313 0.3560 0.4766 0.0358 1.0000 Uiso . . . . . H122 H 0.1324 0.5009 0.4316 0.0358 1.0000 Uiso . . . . . H123 H 0.1531 0.2886 0.4338 0.0358 1.0000 Uiso . . . . . H131 H 0.2212 0.3979 0.6275 0.0399 1.0000 Uiso . . . . . H132 H 0.1637 0.4633 0.5716 0.0399 1.0000 Uiso . . . . . H133 H 0.1873 0.2540 0.5757 0.0399 1.0000 Uiso . . . . . H141 H 0.4061 0.6004 0.7990 0.0444 1.0000 Uiso . . . . . H142 H 0.3429 0.6608 0.7512 0.0444 1.0000 Uiso . . . . . H143 H 0.3621 0.4453 0.7573 0.0444 1.0000 Uiso . . . . . H151 H 0.0541 0.2984 0.0230 0.0435 1.0000 Uiso . . . . . H161 H 0.0499 0.2580 -0.0596 0.0584 1.0000 Uiso . . . . . H162 H -0.0111 0.3054 -0.1138 0.0584 1.0000 Uiso . . . . . H163 H 0.0078 0.0913 -0.0965 0.0584 1.0000 Uiso . . . . . H171 H -0.0866 0.1730 -0.0426 0.0481 1.0000 Uiso . . . . . H172 H -0.0974 0.2517 -0.1030 0.0481 1.0000 Uiso . . . . . H173 H -0.0785 0.0376 -0.0857 0.0481 1.0000 Uiso . . . . . H181 H 0.5407 0.9377 0.8191 0.0412 0.5000 Uiso . . . 1 -1 H191 H 0.5393 1.2419 0.8303 0.0625 0.5000 Uiso . . . 1 -1 H192 H 0.5379 1.3573 0.7785 0.0625 0.5000 Uiso . . . 1 -1 H193 H 0.4819 1.3470 0.7851 0.0625 0.5000 Uiso . . . 1 -1 H201 H 0.4533 1.0077 0.6769 0.0572 0.5000 Uiso . . . 1 -1 H202 H 0.4824 1.2065 0.6796 0.0572 0.5000 Uiso . . . 1 -1 H203 H 0.4264 1.1962 0.6862 0.0572 0.5000 Uiso . . . 1 -1 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 Ni1 0.02248(15) 0.02406(16) 0.02034(15) -0.00039(13) 0.01191(12) -0.00087(14) S1 0.0229(3) 0.0315(3) 0.0216(3) -0.0013(2) 0.0119(2) -0.0031(3) C1 0.0248(11) 0.0221(12) 0.0205(11) -0.0005(10) 0.0124(9) 0.0011(10) N1 0.0278(11) 0.0259(11) 0.0211(10) -0.0018(8) 0.0130(8) -0.0012(9) N2 0.0240(10) 0.0222(10) 0.0225(10) -0.0014(8) 0.0124(8) -0.0006(9) C2 0.0251(12) 0.0203(12) 0.0290(12) -0.0025(10) 0.0154(10) -0.0025(10) C3 0.0288(12) 0.0199(12) 0.0278(12) -0.0010(9) 0.0188(10) 0.0005(10) N3 0.0272(11) 0.0222(10) 0.0236(10) -0.0008(8) 0.0143(9) -0.0003(9) N4 0.0275(11) 0.0301(12) 0.0227(10) 0.0004(8) 0.0135(9) -0.0010(9) C4 0.0319(13) 0.0261(13) 0.0251(12) -0.0007(10) 0.0162(11) 0.0025(11) S2 0.0253(3) 0.0395(4) 0.0228(3) -0.0014(3) 0.0129(2) -0.0038(3) N5 0.0248(11) 0.0316(12) 0.0235(10) 0.0008(9) 0.0136(9) -0.0045(10) C5 0.0283(12) 0.0213(13) 0.0215(11) 0.0013(9) 0.0130(10) 0.0022(10) C6 0.0265(13) 0.0316(14) 0.0281(13) -0.0016(11) 0.0165(11) -0.0017(11) C7 0.0330(13) 0.0290(14) 0.0223(12) -0.0019(10) 0.0164(11) -0.0010(11) C8 0.0263(12) 0.0248(12) 0.0233(11) -0.0010(10) 0.0126(10) 0.0023(11) C9 0.0272(12) 0.0329(14) 0.0281(12) -0.0034(11) 0.0174(10) -0.0007(11) C10 0.0266(12) 0.0331(14) 0.0237(12) -0.0023(11) 0.0136(10) -0.0013(11) C11 0.0273(13) 0.0300(14) 0.0270(12) -0.0004(11) 0.0150(11) 0.0011(11) O1 0.0280(9) 0.0475(12) 0.0264(9) -0.0092(8) 0.0142(8) 0.0011(9) O2 0.0251(10) 0.0677(15) 0.0268(10) -0.0108(10) 0.0116(8) 0.0018(10) C12 0.0258(13) 0.0304(15) 0.0332(14) -0.0014(11) 0.0166(11) -0.0014(11) C13 0.0339(14) 0.0316(15) 0.0343(14) 0.0007(11) 0.0220(12) -0.0028(11) N6 0.0307(12) 0.0424(15) 0.0244(11) -0.0011(10) 0.0141(10) -0.0011(11) C14 0.0457(16) 0.0420(16) 0.0233(12) 0.0016(12) 0.0190(12) -0.0035(14) O3 0.0322(11) 0.0662(15) 0.0304(10) -0.0085(10) 0.0151(9) -0.0027(10) C15 0.0266(14) 0.0504(18) 0.0317(14) -0.0040(13) 0.0119(12) -0.0019(13) N7 0.0246(11) 0.0471(15) 0.0277(11) -0.0020(10) 0.0127(9) 0.0027(10) C16 0.0346(16) 0.080(3) 0.0314(15) 0.0019(16) 0.0180(13) 0.0067(17) C17 0.0280(14) 0.060(2) 0.0325(15) -0.0037(14) 0.0116(12) -0.0034(14) O4 0.026(9) 0.0384(17) 0.048(2) 0.002(4) 0.010(4) -0.003(4) C18 0.026(3) 0.040(2) 0.037(3) 0.002(2) 0.009(2) 0.001(2) N8 0.030(3) 0.0350(18) 0.043(3) 0.000(2) 0.017(3) -0.004(3) C19 0.047(4) 0.044(4) 0.065(4) -0.013(3) 0.021(3) -0.010(3) C20 0.045(3) 0.055(4) 0.043(3) 0.014(3) 0.024(2) 0.006(3) _refine_ls_extinction_method None 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 Ni1 . S1 . 2.1552(7) yes Ni1 . N2 . 1.854(2) yes Ni1 . N3 . 1.856(2) yes Ni1 . S2 . 2.1508(7) yes S1 . C1 . 1.764(2) yes C1 . N1 . 1.308(3) yes C1 . N5 . 1.361(3) yes N1 . N2 . 1.383(3) yes N2 . C2 . 1.304(3) yes C2 . C3 . 1.474(3) yes C2 . C12 . 1.489(4) yes C3 . N3 . 1.308(3) yes C3 . C13 . 1.495(3) yes N3 . N4 . 1.375(3) yes N4 . C4 . 1.317(3) yes C4 . S2 . 1.769(3) yes C4 . N6 . 1.334(3) yes N5 . C5 . 1.399(3) yes N5 . H1 . 0.79(3) no C5 . C6 . 1.405(3) yes C5 . C10 . 1.394(4) yes C6 . C7 . 1.380(3) yes C6 . H61 . 1.000 no C7 . C8 . 1.390(4) yes C7 . H71 . 1.000 no C8 . C9 . 1.400(3) yes C8 . C11 . 1.483(3) yes C9 . C10 . 1.394(4) yes C9 . H91 . 1.000 no C10 . H101 . 1.000 no C11 . O1 . 1.229(3) yes C11 . O2 . 1.314(3) yes O2 . H2 . 0.84(4) no C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no N6 . C14 . 1.459(3) yes N6 . H3 . 0.82(3) no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 1.000 no O3 . C15 . 1.236(3) yes C15 . N7 . 1.317(4) yes C15 . H151 . 1.000 no N7 . C16 . 1.463(4) yes N7 . C17 . 1.450(4) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 no C16 . H163 . 1.000 no C17 . H171 . 1.000 no C17 . H172 . 1.000 no C17 . H173 . 1.000 no O4 . C18 . 1.242(18) yes C18 . N8 . 1.327(8) yes C18 . H181 . 1.000 no N8 . C19 . 1.454(9) yes N8 . C20 . 1.461(11) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no 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 S1 . Ni1 . N2 . 87.18(6) yes S1 . Ni1 . N3 . 170.94(7) yes N2 . Ni1 . N3 . 83.76(9) yes S1 . Ni1 . S2 . 101.69(3) yes N2 . Ni1 . S2 . 171.03(6) yes N3 . Ni1 . S2 . 87.37(7) yes Ni1 . S1 . C1 . 94.43(8) yes S1 . C1 . N1 . 124.17(18) yes S1 . C1 . N5 . 114.80(18) yes N1 . C1 . N5 . 121.0(2) yes C1 . N1 . N2 . 109.87(19) yes Ni1 . N2 . N1 . 124.33(16) yes Ni1 . N2 . C2 . 115.77(17) yes N1 . N2 . C2 . 119.9(2) yes N2 . C2 . C3 . 112.4(2) yes N2 . C2 . C12 . 123.9(2) yes C3 . C2 . C12 . 123.7(2) yes C2 . C3 . N3 . 112.8(2) yes C2 . C3 . C13 . 123.0(2) yes N3 . C3 . C13 . 124.2(2) yes Ni1 . N3 . C3 . 115.29(16) yes Ni1 . N3 . N4 . 124.41(16) yes C3 . N3 . N4 . 120.3(2) yes N3 . N4 . C4 . 109.9(2) yes N4 . C4 . S2 . 123.87(19) yes N4 . C4 . N6 . 119.9(2) yes S2 . C4 . N6 . 116.3(2) yes Ni1 . S2 . C4 . 94.39(9) yes C1 . N5 . C5 . 129.4(2) yes C1 . N5 . H1 . 116(2) no C5 . N5 . H1 . 115(2) no N5 . C5 . C6 . 116.3(2) yes N5 . C5 . C10 . 124.5(2) yes C6 . C5 . C10 . 119.2(2) yes C5 . C6 . C7 . 120.8(2) yes C5 . C6 . H61 . 119.603 no C7 . C6 . H61 . 119.603 no C6 . C7 . C8 . 120.3(2) yes C6 . C7 . H71 . 119.862 no C8 . C7 . H71 . 119.862 no C7 . C8 . C9 . 119.2(2) yes C7 . C8 . C11 . 119.9(2) yes C9 . C8 . C11 . 120.9(2) yes C8 . C9 . C10 . 120.9(2) yes C8 . C9 . H91 . 119.569 no C10 . C9 . H91 . 119.569 no C5 . C10 . C9 . 119.6(2) yes C5 . C10 . H101 . 120.202 no C9 . C10 . H101 . 120.202 no C8 . C11 . O1 . 122.3(2) yes C8 . C11 . O2 . 114.9(2) yes O1 . C11 . O2 . 122.7(2) yes C11 . O2 . H2 . 111(3) no C2 . C12 . H121 . 109.467 no C2 . C12 . H122 . 109.467 no H121 . C12 . H122 . 109.476 no C2 . C12 . H123 . 109.467 no H121 . C12 . H123 . 109.476 no H122 . C12 . H123 . 109.476 no C3 . C13 . H131 . 109.467 no C3 . C13 . H132 . 109.467 no H131 . C13 . H132 . 109.476 no C3 . C13 . H133 . 109.467 no H131 . C13 . H133 . 109.476 no H132 . C13 . H133 . 109.476 no C4 . N6 . C14 . 122.1(2) yes C4 . N6 . H3 . 121(2) no C14 . N6 . H3 . 115(2) no N6 . C14 . H141 . 109.467 no N6 . C14 . H142 . 109.467 no H141 . C14 . H142 . 109.476 no N6 . C14 . H143 . 109.467 no H141 . C14 . H143 . 109.475 no H142 . C14 . H143 . 109.476 no O3 . C15 . N7 . 124.8(3) yes O3 . C15 . H151 . 117.576 no N7 . C15 . H151 . 117.576 no C15 . N7 . C16 . 121.6(2) yes C15 . N7 . C17 . 121.7(2) yes C16 . N7 . C17 . 116.7(2) yes N7 . C16 . H161 . 109.467 no N7 . C16 . H162 . 109.467 no H161 . C16 . H162 . 109.476 no N7 . C16 . H163 . 109.467 no H161 . C16 . H163 . 109.476 no H162 . C16 . H163 . 109.476 no N7 . C17 . H171 . 109.467 no N7 . C17 . H172 . 109.467 no H171 . C17 . H172 . 109.476 no N7 . C17 . H173 . 109.467 no H171 . C17 . H173 . 109.476 no H172 . C17 . H173 . 109.476 no O4 . C18 . N8 . 123.4(14) yes O4 . C18 . H181 . 118.286 no N8 . C18 . H181 . 118.327 no C18 . N8 . C19 . 121.1(9) yes C18 . N8 . C20 . 119.9(6) yes C19 . N8 . C20 . 118.9(6) yes N8 . C19 . H191 . 109.467 no N8 . C19 . H192 . 109.466 no H191 . C19 . H192 . 109.475 no N8 . C19 . H193 . 109.468 no H191 . C19 . H193 . 109.475 no H192 . C19 . H193 . 109.476 no N8 . C20 . H201 . 109.466 no N8 . C20 . H202 . 109.466 no N8 . C20 . H203 . 109.467 no H201 . C20 . H202 . 109.475 no H201 . C20 . H203 . 109.476 no H202 . C20 . H203 . 109.477 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 N5 H1 O1 7_555 0.79(3) 2.19(3) 2.973(3) 172(3) yes O2 H2 O3 . 0.84(4) 1.73(4) 2.567(3) 177(4) yes N6 H3 O4 . 0.82(3) 2.05(6) 2.85(4) 170(3) yes N6 H3 O4 5_656 0.82(3) 2.23(6) 3.03(5) 168(3) yes