# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Hirokazu Arimoto' _publ_contact_author_email ARIMOTO@BIOCHEM.TOHOKU.AC.JP _publ_section_title ; 8-Nitroguanosines as chemical probes of the protein S-guanylation ; loop_ _publ_author_name 'Hirokazu Arimoto' 'Takaaki Akaike' 'Shigemoto Fujii' 'Shigemoto Fujii' 'Chizuko Kabuto' 'Eriko Kida' 'Yohei Saito' ; T.Sawa ; 'Hirobumi Taguchi' # Attachment 'final.cif' #============================================================================== data__arimoto _database_code_depnum_ccdc_archive 'CCDC 692937' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C10 H13 F N6 O7 ' _chemical_formula_moiety 'C10 H13 F N6 O7 ' _chemical_formula_weight 348.25 _chemical_melting_point ? _chemical_absolute_configuration rm #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 9.577(7) _cell_length_b 8.241(5) _cell_length_c 9.836(7) _cell_angle_alpha 90.0000 _cell_angle_beta 116.656(4) _cell_angle_gamma 90.0000 _cell_volume 693.8(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1819 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 173.1 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360.00 _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.746 _exptl_absorpt_correction_T_max 0.978 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 12042 _diffrn_reflns_av_R_equivalents 0.066 _diffrn_reflns_theta_max 27.46 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.984 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3110 _reflns_number_gt 1645 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.0561 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3110 _refine_ls_number_parameters 230 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[1.0000\s(Fo^2^)]/(4Fo^2^)' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.80 _refine_diff_density_min -0.81 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? 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) ; F F 0.017 0.010 ; 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) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 F(1) F 0.3016(2) 0.0894(2) 0.9293(2) 0.0293(4) Uani 1.00 1 d . . . O(1) O 0.0335(2) 0.4232(2) 0.0642(2) 0.0316(6) Uani 1.00 1 d . . . O(2) O 0.2236(2) 0.6316(2) 0.7855(2) 0.0282(5) Uani 1.00 1 d . . . O(3) O 0.1785(3) 0.7943(2) 0.5906(2) 0.0336(6) Uani 1.00 1 d . . . O(4) O 0.4188(2) 0.3648(2) 0.8412(2) 0.0216(5) Uani 1.00 1 d . . . O(5) O 0.5061(2) -0.0593(2) 0.8432(2) 0.0288(5) Uani 1.00 1 d . . . O(6) O 0.5458(3) 0.3525(3) 0.6305(2) 0.0349(6) Uani 1.00 1 d . . . O(7) O 0.4735(3) 0.1817(3) 0.3552(2) 0.0466(7) Uani 1.00 1 d . . . N(1) N 0.1344(3) 0.5477(3) 0.3990(3) 0.0239(6) Uani 1.00 1 d . . . N(2) N 0.1990(3) 0.3635(3) 0.5958(2) 0.0182(6) Uani 1.00 1 d . . . N(3) N 0.1978(3) 0.6587(3) 0.6500(3) 0.0226(6) Uani 1.00 1 d . . . N(4) N 0.0693(3) 0.1703(3) 0.1731(2) 0.0226(6) Uani 1.00 1 d . . . N(5) N 0.0825(3) -0.0912(3) 0.2637(3) 0.0241(6) Uani 1.00 1 d . . . N(6) N 0.1522(3) 0.1144(3) 0.4445(3) 0.0215(6) Uani 1.00 1 d . . . C(1) C 0.1795(3) 0.5236(4) 0.5465(3) 0.0221(7) Uani 1.00 1 d . . . C(2) C 0.1216(4) 0.3919(4) 0.3406(3) 0.0231(7) Uani 1.00 1 d . . . C(3) C 0.0707(4) 0.3392(4) 0.1825(3) 0.0243(7) Uani 1.00 1 d . . . C(4) C 0.1037(3) 0.0662(3) 0.2971(3) 0.0197(6) Uani 1.00 1 d . . . C(5) C 0.1571(3) 0.2785(3) 0.4575(3) 0.0183(6) Uani 1.00 1 d . . . C(6) C 0.2677(3) 0.3040(3) 0.7611(3) 0.0183(6) Uani 1.00 1 d . . . C(7) C 0.2813(3) 0.1202(3) 0.7771(3) 0.0205(7) Uani 1.00 1 d . . . C(8) C 0.4324(3) 0.0883(4) 0.7737(3) 0.0230(6) Uani 1.00 1 d . . . C(9) C 0.5291(3) 0.2384(3) 0.8558(3) 0.0242(7) Uani 1.00 1 d . . . C(10) C 0.6296(4) 0.2990(4) 0.7866(4) 0.0322(8) Uani 1.00 1 d . . . H(1) H 0.0441 0.1098 0.0743 0.023 Uiso 1.00 1 c R . . H(2) H 0.0998 -0.1627 0.3359 0.029 Uiso 1.00 1 c R . . H(3) H 0.0514 -0.1238 0.1693 0.029 Uiso 1.00 1 c R . . H(4) H 0.2015 0.3448 0.8087 0.022 Uiso 1.00 1 c R . . H(5) H 0.1909 0.0608 0.6966 0.025 Uiso 1.00 1 c R . . H(6) H 0.4153 0.0890 0.6657 0.028 Uiso 1.00 1 c R . . H(7) H 0.6932 0.3905 0.8487 0.039 Uiso 1.00 1 c R . . H(8) H 0.7023 0.2113 0.7915 0.039 Uiso 1.00 1 c R . . H(9) H 0.5952 0.2130 0.9658 0.029 Uiso 1.00 1 c R . . H(10) H 0.5099 0.2163 0.4613 0.023 Uiso 1.00 1 c R . . H(11) H 0.4381 0.2341 0.2572 0.023 Uiso 1.00 1 c R . . H(12) H 0.5399 0.4742 0.6393 0.023 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F(1) 0.0396(10) 0.0230(10) 0.0250(10) 0.0045(9) 0.0141(8) 0.0095(9) O(1) 0.0485(15) 0.0198(13) 0.0209(13) 0.0007(11) 0.0105(12) 0.0046(10) O(2) 0.0395(13) 0.0228(13) 0.0196(12) -0.0015(10) 0.0107(10) -0.0017(9) O(3) 0.0555(16) 0.0078(12) 0.0307(14) -0.0017(11) 0.0134(13) 0.0017(10) O(4) 0.0248(11) 0.0131(11) 0.0215(12) 0.0008(9) 0.0056(9) -0.0015(9) O(5) 0.0379(13) 0.0162(12) 0.0316(14) 0.0108(10) 0.0151(11) 0.0069(10) O(6) 0.0538(16) 0.0226(13) 0.0330(14) -0.0063(11) 0.0236(12) -0.0004(11) O(7) 0.0811(19) 0.0262(14) 0.0323(15) -0.0089(14) 0.0252(14) -0.0021(12) N(1) 0.0326(14) 0.0106(14) 0.0236(16) -0.0010(11) 0.0083(12) -0.0012(11) N(2) 0.0262(14) 0.0100(13) 0.0139(13) 0.0014(10) 0.0049(11) 0.0013(11) N(3) 0.0309(14) 0.0107(14) 0.0227(14) -0.0013(11) 0.0089(11) -0.0026(11) N(4) 0.0378(16) 0.0096(13) 0.0180(14) -0.0007(11) 0.0104(12) -0.0001(11) N(5) 0.0359(16) 0.0122(14) 0.0223(15) 0.0005(11) 0.0114(13) -0.0020(11) N(6) 0.0299(13) 0.0106(14) 0.0216(14) -0.0002(11) 0.0094(12) -0.0006(11) C(1) 0.0306(17) 0.0112(15) 0.0206(18) -0.0009(13) 0.0081(14) -0.0019(13) C(2) 0.0315(19) 0.0154(17) 0.0209(17) 0.0012(13) 0.0105(15) -0.0007(13) C(3) 0.0352(19) 0.0138(17) 0.0206(18) 0.0052(14) 0.0097(15) 0.0037(13) C(4) 0.0213(15) 0.0131(16) 0.0226(17) 0.0009(11) 0.0078(13) 0.0003(13) C(5) 0.0234(15) 0.0098(15) 0.0170(16) 0.0005(12) 0.0048(13) -0.0016(12) C(6) 0.0233(15) 0.0157(16) 0.0121(15) -0.0034(12) 0.0046(13) 0.0004(12) C(7) 0.0297(16) 0.0149(17) 0.0140(15) 0.0012(13) 0.0073(13) 0.0019(12) C(8) 0.0327(17) 0.0127(15) 0.0195(16) 0.0073(13) 0.0081(14) 0.0068(14) C(9) 0.0306(17) 0.0165(17) 0.0222(18) 0.0032(14) 0.0089(14) -0.0012(13) C(10) 0.0360(19) 0.030(2) 0.031(2) -0.0042(16) 0.0152(17) -0.0024(16) #============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR97 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F(1) C(7) 1.443(4) yes . . O(1) C(3) 1.260(4) yes . . O(2) N(3) 1.262(4) yes . . O(3) N(3) 1.236(3) yes . . O(4) C(6) 1.394(3) yes . . O(4) C(9) 1.444(4) yes . . O(5) C(8) 1.419(3) yes . . O(6) C(10) 1.446(4) yes . . N(1) C(1) 1.330(4) yes . . N(1) C(2) 1.389(4) yes . . N(2) C(1) 1.389(4) yes . . N(2) C(5) 1.418(4) yes . . N(2) C(6) 1.536(3) yes . . N(3) C(1) 1.465(4) yes . . N(4) C(3) 1.395(4) yes . . N(4) C(4) 1.404(4) yes . . N(5) C(4) 1.332(4) yes . . N(6) C(4) 1.368(4) yes . . N(6) C(5) 1.358(3) yes . . C(2) C(3) 1.471(4) yes . . C(2) C(5) 1.400(4) yes . . C(6) C(7) 1.523(4) yes . . C(7) C(8) 1.486(5) yes . . C(8) C(9) 1.539(4) yes . . C(9) C(10) 1.492(6) yes . . O(6) H(12) 1.011 no . . O(7) H(10) 0.983 no . . O(7) H(11) 0.968 no . . N(4) H(1) 1.020 no . . N(5) H(2) 0.880 no . . N(5) H(3) 0.880 no . . C(6) H(4) 1.000 no . . C(7) H(5) 1.000 no . . C(8) H(6) 1.000 no . . C(9) H(9) 1.000 no . . C(10) H(7) 0.990 no . . C(10) H(8) 0.990 no . . 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(6) O(4) C(9) 109.0(2) yes . . . C(1) N(1) C(2) 103.8(2) yes . . . C(1) N(2) C(5) 101.5(2) yes . . . C(1) N(2) C(6) 126.8(2) yes . . . C(5) N(2) C(6) 131.3(2) yes . . . O(2) N(3) O(3) 125.2(2) yes . . . O(2) N(3) C(1) 120.3(2) yes . . . O(3) N(3) C(1) 114.4(2) yes . . . C(3) N(4) C(4) 124.1(2) yes . . . C(4) N(6) C(5) 111.7(2) yes . . . N(1) C(1) N(2) 116.7(2) yes . . . N(1) C(1) N(3) 121.6(2) yes . . . N(2) C(1) N(3) 121.6(2) yes . . . N(1) C(2) C(3) 129.5(3) yes . . . N(1) C(2) C(5) 109.5(3) yes . . . C(3) C(2) C(5) 120.9(2) yes . . . O(1) C(3) N(4) 119.7(3) yes . . . O(1) C(3) C(2) 129.5(3) yes . . . N(4) C(3) C(2) 110.7(2) yes . . . N(4) C(4) N(5) 115.5(2) yes . . . N(4) C(4) N(6) 125.4(2) yes . . . N(5) C(4) N(6) 119.1(3) yes . . . N(2) C(5) N(6) 124.4(2) yes . . . N(2) C(5) C(2) 108.5(2) yes . . . N(6) C(5) C(2) 127.1(3) yes . . . O(4) C(6) N(2) 109.1(2) yes . . . O(4) C(6) C(7) 106.3(2) yes . . . N(2) C(6) C(7) 113.8(2) yes . . . F(1) C(7) C(6) 104.3(2) yes . . . F(1) C(7) C(8) 108.2(2) yes . . . C(6) C(7) C(8) 102.3(2) yes . . . O(5) C(8) C(7) 114.8(3) yes . . . O(5) C(8) C(9) 112.6(2) yes . . . C(7) C(8) C(9) 102.1(2) yes . . . O(4) C(9) C(8) 106.6(2) yes . . . O(4) C(9) C(10) 107.8(2) yes . . . C(8) C(9) C(10) 112.9(3) yes . . . O(6) C(10) C(9) 115.0(2) yes . . . C(10) O(6) H(12) 103.7 no . . . H(10) O(7) H(11) 136.6 no . . . C(3) N(4) H(1) 122.8 no . . . C(4) N(4) H(1) 113.1 no . . . C(4) N(5) H(2) 120.0 no . . . C(4) N(5) H(3) 120.0 no . . . H(2) N(5) H(3) 120.0 no . . . O(4) C(6) H(4) 109.2 no . . . N(2) C(6) H(4) 109.2 no . . . C(7) C(6) H(4) 109.2 no . . . F(1) C(7) H(5) 113.7 no . . . C(6) C(7) H(5) 113.7 no . . . C(8) C(7) H(5) 113.7 no . . . O(5) C(8) H(6) 109.0 no . . . C(7) C(8) H(6) 109.0 no . . . C(9) C(8) H(6) 109.0 no . . . O(4) C(9) H(9) 109.8 no . . . C(8) C(9) H(9) 109.8 no . . . C(10) C(9) H(9) 109.8 no . . . O(6) C(10) H(7) 108.5 no . . . O(6) C(10) H(8) 108.5 no . . . C(9) C(10) H(7) 108.5 no . . . C(9) C(10) H(8) 108.5 no . . . H(7) C(10) H(8) 107.5 no . . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================