# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 1475 loop_ _publ_author_name 'Gale, Philip' 'Coles, Simon' _publ_contact_author_name 'Gale, Philip' _publ_contact_author_email philip.gale@soton.ac.uk _publ_section_title ; Changing and challenging times for service crystallography ; # Attachment '- DLS 1s att.cif' data_DLS1satt _database_code_depnum_ccdc_archive 'CCDC 855293' #TrackingRef '- DLS 1s att.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H23 N7 O11' _chemical_formula_weight 525.44 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.537(7) _cell_length_b 11.248(9) _cell_length_c 12.439(10) _cell_angle_alpha 107.701(9) _cell_angle_beta 97.463(6) _cell_angle_gamma 104.937(10) _cell_volume 1196.4(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2318 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 26.6 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 0.530 _exptl_absorpt_process_details REQAB _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.68890 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'DLS beamline I19' _diffrn_radiation_monochromator 'Si 111 Double Crystal' _diffrn_measurement_device ; CrystalLogic Kappa (3 circle) ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11746 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 26.60 _reflns_number_total 5223 _reflns_number_gt 3330 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. The urea H atoms were located from the difference map and refined with the bond distance restrained to 0.88A. ; _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^)+(0.1605P)^2^+0.0443P] 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 5223 _refine_ls_number_parameters 343 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1108 _refine_ls_R_factor_gt 0.0810 _refine_ls_wR_factor_ref 0.2662 _refine_ls_wR_factor_gt 0.2357 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 C1 C 0.2434(3) 0.4904(2) 0.4764(2) 0.0555(6) Uani 1 1 d . . . C2 C 0.0067(3) 0.3137(2) 0.4356(2) 0.0550(6) Uani 1 1 d . . . C3 C -0.0985(3) 0.2084(2) 0.3457(2) 0.0595(6) Uani 1 1 d . . . H3 H -0.0869 0.1892 0.2698 0.071 Uiso 1 1 calc R . . C4 C -0.2198(3) 0.1332(3) 0.3709(2) 0.0622(6) Uani 1 1 d . . . C5 C -0.2432(3) 0.1557(3) 0.4812(2) 0.0640(7) Uani 1 1 d . . . H5 H -0.3258 0.1039 0.4965 0.077 Uiso 1 1 calc R . . C6 C -0.1369(3) 0.2595(3) 0.5672(2) 0.0597(6) Uani 1 1 d . . . C7 C -0.0129(3) 0.3395(2) 0.5484(2) 0.0577(6) Uani 1 1 d . . . H7 H 0.0557 0.4089 0.6098 0.069 Uiso 1 1 calc R . . C8 C 0.4734(3) 0.6410(2) 0.4617(2) 0.0572(6) Uani 1 1 d . . . C9 C 0.5227(3) 0.7223(3) 0.5777(2) 0.0615(6) Uani 1 1 d . . . H9 H 0.4674 0.7084 0.6315 0.074 Uiso 1 1 calc R . . C10 C 0.6544(3) 0.8234(3) 0.6111(2) 0.0653(7) Uani 1 1 d . . . C11 C 0.7427(3) 0.8517(3) 0.5365(3) 0.0683(7) Uani 1 1 d . . . H11 H 0.8311 0.9214 0.5615 0.082 Uiso 1 1 calc R . . C12 C 0.6902(3) 0.7696(3) 0.4231(3) 0.0636(7) Uani 1 1 d . . . C13 C 0.5601(3) 0.6660(3) 0.3830(2) 0.0603(6) Uani 1 1 d . . . H13 H 0.5297 0.6133 0.3051 0.072 Uiso 1 1 calc R . . N1 N 0.1255(2) 0.3869(2) 0.40397(19) 0.0611(5) Uani 1 1 d D . . N2 N 0.3422(2) 0.5359(2) 0.41506(19) 0.0607(5) Uani 1 1 d D . . N3 N -0.3289(3) 0.0236(2) 0.2753(2) 0.0776(7) Uani 1 1 d . . . N4 N -0.1568(3) 0.2864(3) 0.6861(2) 0.0765(7) Uani 1 1 d . . . N5 N 0.7048(3) 0.9075(3) 0.7350(3) 0.0836(7) Uani 1 1 d . . . N6 N 0.7792(3) 0.7915(3) 0.3380(3) 0.0776(7) Uani 1 1 d . . . O1 O 0.25949(19) 0.53744(18) 0.58114(15) 0.0659(5) Uani 1 1 d . . . O2 O -0.3155(3) 0.0109(3) 0.1761(2) 0.1081(9) Uani 1 1 d . . . O3 O -0.4290(3) -0.0496(2) 0.2995(2) 0.0981(8) Uani 1 1 d . . . O4 O -0.2726(3) 0.2252(3) 0.7014(2) 0.1184(10) Uani 1 1 d . . . O5 O -0.0586(3) 0.3701(3) 0.7635(2) 0.1158(10) Uani 1 1 d . . . O6 O 0.6214(3) 0.8937(3) 0.7984(2) 0.1030(8) Uani 1 1 d . . . O7 O 0.8301(4) 0.9877(3) 0.7682(3) 0.1440(13) Uani 1 1 d . . . O8 O 0.8895(3) 0.8876(3) 0.3714(3) 0.0997(8) Uani 1 1 d . . . O9 O 0.7372(3) 0.7122(3) 0.2391(3) 0.1066(9) Uani 1 1 d . . . H1N H 0.125(3) 0.360(3) 0.3301(16) 0.072(8) Uiso 1 1 d D . . H2N H 0.310(3) 0.486(3) 0.3398(17) 0.075(9) Uiso 1 1 d D . . C14 C 0.1914(4) 0.3158(4) 0.1291(3) 0.0846(9) Uani 1 1 d . . . C15 C 0.1682(5) 0.2285(5) 0.0068(3) 0.1298(17) Uani 1 1 d . . . H15A H 0.1265 0.1385 0.0000 0.195 Uiso 1 1 calc R . . H15B H 0.2620 0.2403 -0.0156 0.195 Uiso 1 1 calc R . . H15C H 0.1011 0.2504 -0.0429 0.195 Uiso 1 1 calc R . . O10 O 0.3125(3) 0.4010(3) 0.1804(2) 0.1097(9) Uani 1 1 d . . . O11 O 0.0821(4) 0.2959(3) 0.1731(2) 0.1308(12) Uani 1 1 d . . . C16 C 0.4333(7) 0.6647(8) 1.0375(6) 0.200(3) Uani 1 1 d . . . H16A H 0.4377 0.5769 1.0057 0.300 Uiso 1 1 calc R . . H16B H 0.4180 0.6810 1.1148 0.300 Uiso 1 1 calc R . . H16C H 0.5252 0.7264 1.0394 0.300 Uiso 1 1 calc R . . C17 C 0.3039(10) 0.8112(5) 1.0156(5) 0.206(4) Uani 1 1 d . . . H17A H 0.3095 0.8323 1.0971 0.309 Uiso 1 1 calc R . . H17B H 0.2117 0.8164 0.9791 0.309 Uiso 1 1 calc R . . H17C H 0.3857 0.8724 1.0035 0.309 Uiso 1 1 calc R . . C18 C 0.3044(8) 0.6384(6) 0.8412(4) 0.174(3) Uani 1 1 d . . . H18A H 0.3083 0.5501 0.8135 0.261 Uiso 1 1 calc R . . H18B H 0.3875 0.6961 0.8269 0.261 Uiso 1 1 calc R . . H18C H 0.2132 0.6420 0.8014 0.261 Uiso 1 1 calc R . . C19 C 0.1764(8) 0.5891(9) 0.9801(6) 0.218(4) Uani 1 1 d . . . H19A H 0.1771 0.5001 0.9481 0.327 Uiso 1 1 calc R . . H19B H 0.0886 0.5981 0.9404 0.327 Uiso 1 1 calc R . . H19C H 0.1765 0.6105 1.0610 0.327 Uiso 1 1 calc R . . N7 N 0.3109(3) 0.6797(2) 0.96599(19) 0.0706(6) Uani 1 1 d . . . 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 C1 0.0528(12) 0.0566(13) 0.0587(14) 0.0225(11) 0.0193(10) 0.0136(11) C2 0.0519(12) 0.0560(13) 0.0585(14) 0.0232(11) 0.0178(10) 0.0129(10) C3 0.0597(14) 0.0588(14) 0.0572(14) 0.0193(12) 0.0183(11) 0.0127(12) C4 0.0575(14) 0.0564(14) 0.0671(16) 0.0218(12) 0.0134(12) 0.0092(12) C5 0.0551(13) 0.0666(16) 0.0714(17) 0.0326(14) 0.0172(12) 0.0096(12) C6 0.0551(13) 0.0678(16) 0.0619(15) 0.0305(13) 0.0207(11) 0.0159(12) C7 0.0541(13) 0.0617(14) 0.0569(14) 0.0238(11) 0.0162(10) 0.0125(11) C8 0.0545(12) 0.0589(14) 0.0623(15) 0.0251(12) 0.0224(11) 0.0155(11) C9 0.0575(13) 0.0636(15) 0.0623(15) 0.0241(12) 0.0204(11) 0.0115(12) C10 0.0609(14) 0.0612(15) 0.0683(17) 0.0202(13) 0.0126(12) 0.0144(12) C11 0.0554(14) 0.0657(16) 0.087(2) 0.0355(15) 0.0191(13) 0.0125(12) C12 0.0546(13) 0.0694(16) 0.0797(18) 0.0397(14) 0.0271(12) 0.0190(12) C13 0.0546(13) 0.0687(16) 0.0651(15) 0.0310(12) 0.0241(11) 0.0180(12) N1 0.0617(12) 0.0621(12) 0.0533(12) 0.0192(10) 0.0223(10) 0.0061(10) N2 0.0600(12) 0.0626(13) 0.0552(13) 0.0200(10) 0.0220(10) 0.0085(10) N3 0.0663(14) 0.0665(15) 0.0814(18) 0.0220(13) 0.0085(12) -0.0009(12) N4 0.0681(14) 0.0940(18) 0.0641(15) 0.0345(14) 0.0236(12) 0.0077(13) N5 0.0781(17) 0.0770(17) 0.0766(17) 0.0175(14) 0.0126(14) 0.0069(14) N6 0.0657(14) 0.0902(17) 0.097(2) 0.0532(16) 0.0390(13) 0.0226(13) O1 0.0616(10) 0.0737(12) 0.0541(10) 0.0210(9) 0.0186(8) 0.0065(9) O2 0.1076(19) 0.1001(18) 0.0721(15) 0.0086(13) 0.0147(13) -0.0120(14) O3 0.0783(14) 0.0848(15) 0.1026(19) 0.0346(13) 0.0060(12) -0.0166(12) O4 0.0928(17) 0.159(2) 0.0867(17) 0.0543(17) 0.0387(14) -0.0108(17) O5 0.0967(18) 0.144(2) 0.0665(14) 0.0229(15) 0.0273(13) -0.0162(17) O6 0.1103(19) 0.1008(18) 0.0750(15) 0.0145(13) 0.0272(14) 0.0118(15) O7 0.102(2) 0.147(3) 0.104(2) -0.0002(19) 0.0083(17) -0.032(2) O8 0.0732(13) 0.1042(17) 0.132(2) 0.0618(16) 0.0469(13) 0.0094(13) O9 0.1027(18) 0.126(2) 0.0900(18) 0.0432(17) 0.0519(14) 0.0128(16) C14 0.091(2) 0.093(2) 0.0657(18) 0.0233(17) 0.0301(16) 0.0212(19) C15 0.125(3) 0.179(5) 0.071(2) 0.021(3) 0.042(2) 0.043(3) O10 0.0903(17) 0.139(2) 0.0736(15) 0.0175(15) 0.0308(13) 0.0111(17) O11 0.120(2) 0.153(3) 0.0653(15) 0.0083(15) 0.0408(14) -0.0189(19) C16 0.148(5) 0.237(8) 0.198(7) 0.043(6) -0.022(5) 0.104(5) C17 0.356(12) 0.119(4) 0.119(4) 0.013(3) -0.001(6) 0.096(6) C18 0.230(7) 0.194(6) 0.081(3) 0.022(3) 0.069(4) 0.053(5) C19 0.178(6) 0.263(8) 0.126(5) 0.055(5) 0.046(4) -0.063(6) N7 0.0709(14) 0.0731(15) 0.0523(12) 0.0124(11) 0.0131(10) 0.0091(12) _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 C1 O1 1.220(3) . ? C1 N1 1.362(3) . ? C1 N2 1.381(3) . ? C2 C7 1.392(4) . ? C2 N1 1.396(3) . ? C2 C3 1.397(4) . ? C3 C4 1.380(3) . ? C3 H3 0.9300 . ? C4 C5 1.376(4) . ? C4 N3 1.464(4) . ? C5 C6 1.373(4) . ? C5 H5 0.9300 . ? C6 C7 1.383(3) . ? C6 N4 1.464(4) . ? C7 H7 0.9300 . ? C8 N2 1.390(3) . ? C8 C9 1.392(4) . ? C8 C13 1.406(3) . ? C9 C10 1.372(4) . ? C9 H9 0.9300 . ? C10 C11 1.384(4) . ? C10 N5 1.479(4) . ? C11 C12 1.372(5) . ? C11 H11 0.9300 . ? C12 C13 1.373(4) . ? C12 N6 1.478(3) . ? C13 H13 0.9300 . ? N1 H1N 0.875(17) . ? N2 H2N 0.896(18) . ? N3 O2 1.226(4) . ? N3 O3 1.224(3) . ? N4 O5 1.205(4) . ? N4 O4 1.214(3) . ? N5 O6 1.205(4) . ? N5 O7 1.226(4) . ? N6 O8 1.214(4) . ? N6 O9 1.221(4) . ? C14 O10 1.235(4) . ? C14 O11 1.240(4) . ? C14 C15 1.490(5) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N7 1.451(5) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 N7 1.442(6) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 N7 1.467(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N7 1.487(7) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 O1 C1 N1 124.8(2) . . ? O1 C1 N2 124.4(2) . . ? N1 C1 N2 110.8(2) . . ? C7 C2 N1 124.6(2) . . ? C7 C2 C3 119.2(2) . . ? N1 C2 C3 116.2(2) . . ? C4 C3 C2 119.1(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C5 C4 C3 123.4(2) . . ? C5 C4 N3 118.4(2) . . ? C3 C4 N3 118.2(3) . . ? C6 C5 C4 115.7(2) . . ? C6 C5 H5 122.2 . . ? C4 C5 H5 122.2 . . ? C5 C6 C7 124.1(2) . . ? C5 C6 N4 117.5(2) . . ? C7 C6 N4 118.3(2) . . ? C6 C7 C2 118.5(2) . . ? C6 C7 H7 120.8 . . ? C2 C7 H7 120.8 . . ? N2 C8 C9 125.3(2) . . ? N2 C8 C13 116.0(2) . . ? C9 C8 C13 118.7(2) . . ? C10 C9 C8 118.8(2) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C9 C10 C11 124.3(3) . . ? C9 C10 N5 117.7(3) . . ? C11 C10 N5 118.0(3) . . ? C12 C11 C10 115.1(3) . . ? C12 C11 H11 122.5 . . ? C10 C11 H11 122.5 . . ? C13 C12 C11 124.1(2) . . ? C13 C12 N6 117.4(3) . . ? C11 C12 N6 118.6(3) . . ? C12 C13 C8 119.0(3) . . ? C12 C13 H13 120.5 . . ? C8 C13 H13 120.5 . . ? C1 N1 C2 126.8(2) . . ? C1 N1 H1N 118(2) . . ? C2 N1 H1N 115(2) . . ? C1 N2 C8 125.9(2) . . ? C1 N2 H2N 109(2) . . ? C8 N2 H2N 125(2) . . ? O2 N3 O3 124.0(3) . . ? O2 N3 C4 118.3(2) . . ? O3 N3 C4 117.8(3) . . ? O5 N4 O4 123.3(3) . . ? O5 N4 C6 118.3(2) . . ? O4 N4 C6 118.4(3) . . ? O6 N5 O7 123.2(3) . . ? O6 N5 C10 118.7(3) . . ? O7 N5 C10 118.1(3) . . ? O8 N6 O9 124.3(3) . . ? O8 N6 C12 117.6(3) . . ? O9 N6 C12 118.0(3) . . ? O10 C14 O11 124.0(3) . . ? O10 C14 C15 120.7(3) . . ? O11 C14 C15 115.3(3) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N7 C16 H16A 109.5 . . ? N7 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N7 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N7 C17 H17A 109.5 . . ? N7 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N7 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N7 C18 H18A 109.5 . . ? N7 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N7 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N7 C19 H19A 109.5 . . ? N7 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N7 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 N7 C16 109.0(4) . . ? C17 N7 C18 113.6(4) . . ? C16 N7 C18 116.5(5) . . ? C17 N7 C19 106.9(5) . . ? C16 N7 C19 103.8(5) . . ? C18 N7 C19 106.1(4) . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 26.60 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.389 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.049 # Attachment '- FRE+ 10s.cif' data_Ros10s _database_code_depnum_ccdc_archive 'CCDC 855294' #TrackingRef '- FRE+ 10s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H23 N7 O11' _chemical_formula_weight 525.44 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.510(17) _cell_length_b 11.31(2) _cell_length_c 12.46(2) _cell_angle_alpha 107.583(19) _cell_angle_beta 97.533(14) _cell_angle_gamma 104.719(19) _cell_volume 1203(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2974 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 0.775 _exptl_absorpt_process_details REQAB _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Confocal mirrors' _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11790 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0666 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5276 _reflns_number_gt 3619 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. The urea H atoms were located from the difference map and refined with the bond distance restrained to 0.88A. ; _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^)+(0.0921P)^2^+0.8256P] 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 5276 _refine_ls_number_parameters 347 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1709 _refine_ls_R_factor_gt 0.1249 _refine_ls_wR_factor_ref 0.2959 _refine_ls_wR_factor_gt 0.2658 _refine_ls_goodness_of_fit_ref 1.237 _refine_ls_restrained_S_all 1.237 _refine_ls_shift/su_max 0.003 _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 C1 C 0.2462(5) 0.4913(4) 0.4768(4) 0.0500(10) Uani 1 1 d . . . C2 C 0.0099(5) 0.3162(4) 0.4373(4) 0.0502(10) Uani 1 1 d . . . C3 C -0.0946(5) 0.2100(4) 0.3470(4) 0.0564(11) Uani 1 1 d . . . H3 H -0.0819 0.1902 0.2715 0.068 Uiso 1 1 calc R . . C4 C -0.2167(5) 0.1355(4) 0.3723(4) 0.0561(11) Uani 1 1 d . . . C5 C -0.2419(5) 0.1581(5) 0.4818(4) 0.0621(12) Uani 1 1 d . . . H5 H -0.3250 0.1069 0.4967 0.075 Uiso 1 1 calc R . . C6 C -0.1359(5) 0.2615(5) 0.5680(4) 0.0586(11) Uani 1 1 d . . . C7 C -0.0113(5) 0.3407(4) 0.5497(4) 0.0539(10) Uani 1 1 d . . . H7 H 0.0572 0.4090 0.6112 0.065 Uiso 1 1 calc R . . C8 C 0.4761(4) 0.6444(4) 0.4641(4) 0.0514(10) Uani 1 1 d . . . C9 C 0.5255(5) 0.7249(4) 0.5796(4) 0.0589(11) Uani 1 1 d . . . H9 H 0.4705 0.7101 0.6334 0.071 Uiso 1 1 calc R . . C10 C 0.6580(5) 0.8278(4) 0.6142(4) 0.0623(12) Uani 1 1 d . . . C11 C 0.7446(5) 0.8554(5) 0.5385(5) 0.0653(13) Uani 1 1 d . . . H11 H 0.8321 0.9254 0.5630 0.078 Uiso 1 1 calc R . . C12 C 0.6940(5) 0.7734(5) 0.4253(4) 0.0576(11) Uani 1 1 d . . . C13 C 0.5638(5) 0.6697(4) 0.3854(4) 0.0563(11) Uani 1 1 d . . . H13 H 0.5340 0.6171 0.3077 0.068 Uiso 1 1 calc R . . N1 N 0.1291(4) 0.3882(4) 0.4060(3) 0.0547(9) Uani 1 1 d D . . N2 N 0.3466(4) 0.5380(3) 0.4181(3) 0.0531(9) Uani 1 1 d D . . N3 N -0.3263(5) 0.0258(4) 0.2760(4) 0.0762(12) Uani 1 1 d . . . N4 N -0.1565(5) 0.2890(5) 0.6874(4) 0.0757(12) Uani 1 1 d . . . N5 N 0.7063(6) 0.9114(5) 0.7379(4) 0.0851(13) Uani 1 1 d . . . N6 N 0.7842(5) 0.7967(5) 0.3408(5) 0.0750(12) Uani 1 1 d . . . O1 O 0.2613(3) 0.5387(3) 0.5819(3) 0.0595(8) Uani 1 1 d . . . O2 O -0.3116(5) 0.0129(4) 0.1771(4) 0.1131(16) Uani 1 1 d . . . O3 O -0.4272(4) -0.0462(4) 0.3000(4) 0.1002(13) Uani 1 1 d . . . O4 O -0.2710(5) 0.2265(5) 0.7013(4) 0.1175(17) Uani 1 1 d . . . O5 O -0.0614(5) 0.3745(5) 0.7641(4) 0.1208(18) Uani 1 1 d . . . O6 O 0.6223(5) 0.8955(4) 0.8011(4) 0.1027(14) Uani 1 1 d . . . O7 O 0.8295(6) 0.9918(5) 0.7710(4) 0.144(2) Uani 1 1 d . . . O8 O 0.8948(4) 0.8922(4) 0.3743(4) 0.1000(14) Uani 1 1 d . . . O9 O 0.7423(5) 0.7173(5) 0.2418(4) 0.1090(15) Uani 1 1 d . . . H1N H 0.126(4) 0.361(4) 0.3316(18) 0.050(11) Uiso 1 1 d D . . H2N H 0.327(4) 0.499(3) 0.3434(17) 0.043(11) Uiso 1 1 d D . . C14 C 0.1974(8) 0.3204(6) 0.1316(5) 0.0858(16) Uani 1 1 d . . . C15 C 0.1796(10) 0.2410(10) 0.0097(5) 0.150(3) Uani 1 1 d . . . H15A H 0.1665 0.1518 0.0028 0.224 Uiso 1 1 calc R . . H15B H 0.2670 0.2733 -0.0167 0.224 Uiso 1 1 calc R . . H15C H 0.0938 0.2461 -0.0366 0.224 Uiso 1 1 calc R . . O10 O 0.3173(5) 0.4058(5) 0.1816(4) 0.1122(15) Uani 1 1 d . . . O11 O 0.0909(6) 0.2950(5) 0.1743(4) 0.139(2) Uani 1 1 d . . . C16 C 0.4352(12) 0.6666(12) 1.0416(10) 0.209(5) Uani 1 1 d . . . H16A H 0.5225 0.7399 1.0580 0.313 Uiso 1 1 calc R . . H16B H 0.4561 0.5875 1.0038 0.313 Uiso 1 1 calc R . . H16C H 0.4075 0.6643 1.1125 0.313 Uiso 1 1 calc R . . C17 C 0.313(2) 0.8092(10) 1.0101(10) 0.277(10) Uani 1 1 d . . . H17A H 0.3947 0.8647 0.9933 0.416 Uiso 1 1 calc R . . H17B H 0.3226 0.8352 1.0923 0.416 Uiso 1 1 calc R . . H17C H 0.2206 0.8166 0.9751 0.416 Uiso 1 1 calc R . . C18 C 0.3099(12) 0.6357(11) 0.8452(7) 0.187(5) Uani 1 1 d . . . H18A H 0.2194 0.6380 0.8027 0.280 Uiso 1 1 calc R . . H18B H 0.3146 0.5480 0.8206 0.280 Uiso 1 1 calc R . . H18C H 0.3941 0.6919 0.8312 0.280 Uiso 1 1 calc R . . C19 C 0.1772(14) 0.6018(16) 0.9816(10) 0.260(8) Uani 1 1 d . . . H19A H 0.1766 0.6282 1.0623 0.391 Uiso 1 1 calc R . . H19B H 0.1713 0.5114 0.9532 0.391 Uiso 1 1 calc R . . H19C H 0.0931 0.6142 0.9398 0.391 Uiso 1 1 calc R . . N7 N 0.3122(5) 0.6790(4) 0.9658(3) 0.0680(11) Uani 1 1 d . . . 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 C1 0.055(2) 0.053(2) 0.047(2) 0.020(2) 0.019(2) 0.020(2) C2 0.054(2) 0.045(2) 0.057(2) 0.022(2) 0.021(2) 0.015(2) C3 0.059(3) 0.051(2) 0.061(3) 0.022(2) 0.015(2) 0.017(2) C4 0.048(2) 0.050(2) 0.068(3) 0.022(2) 0.007(2) 0.012(2) C5 0.047(2) 0.063(3) 0.082(3) 0.037(3) 0.017(2) 0.012(2) C6 0.053(2) 0.066(3) 0.068(3) 0.035(2) 0.023(2) 0.018(2) C7 0.046(2) 0.058(3) 0.059(3) 0.024(2) 0.0107(19) 0.014(2) C8 0.050(2) 0.052(2) 0.060(3) 0.026(2) 0.021(2) 0.017(2) C9 0.058(3) 0.059(3) 0.066(3) 0.026(2) 0.024(2) 0.017(2) C10 0.061(3) 0.056(3) 0.070(3) 0.022(2) 0.016(2) 0.017(2) C11 0.049(2) 0.063(3) 0.091(4) 0.035(3) 0.020(2) 0.016(2) C12 0.047(2) 0.067(3) 0.076(3) 0.040(3) 0.027(2) 0.023(2) C13 0.059(3) 0.061(3) 0.063(3) 0.031(2) 0.025(2) 0.026(2) N1 0.059(2) 0.055(2) 0.045(2) 0.0141(18) 0.0224(18) 0.0077(18) N2 0.054(2) 0.053(2) 0.047(2) 0.0135(17) 0.0206(17) 0.0063(17) N3 0.065(3) 0.064(3) 0.085(3) 0.023(3) 0.008(2) 0.004(2) N4 0.061(3) 0.098(3) 0.069(3) 0.040(3) 0.025(2) 0.007(2) N5 0.079(3) 0.072(3) 0.081(3) 0.012(3) 0.012(3) 0.007(3) N6 0.064(3) 0.083(3) 0.099(4) 0.053(3) 0.034(3) 0.024(2) O1 0.0554(17) 0.0644(19) 0.0564(18) 0.0235(15) 0.0167(14) 0.0099(15) O2 0.112(3) 0.097(3) 0.083(3) 0.009(3) 0.014(3) -0.016(3) O3 0.080(3) 0.083(3) 0.114(3) 0.039(3) 0.009(2) -0.012(2) O4 0.092(3) 0.159(4) 0.090(3) 0.056(3) 0.039(2) -0.004(3) O5 0.102(3) 0.149(4) 0.070(3) 0.022(3) 0.032(2) -0.019(3) O6 0.111(3) 0.094(3) 0.078(3) 0.013(2) 0.030(2) 0.008(3) O7 0.109(4) 0.135(4) 0.111(4) 0.000(3) 0.013(3) -0.034(3) O8 0.070(2) 0.101(3) 0.140(4) 0.065(3) 0.045(2) 0.007(2) O9 0.108(3) 0.131(4) 0.093(3) 0.049(3) 0.053(3) 0.018(3) C14 0.100(5) 0.090(4) 0.066(3) 0.023(3) 0.030(3) 0.027(4) C15 0.164(7) 0.241(10) 0.069(4) 0.047(5) 0.066(5) 0.094(7) O10 0.099(3) 0.139(4) 0.079(3) 0.023(3) 0.033(2) 0.015(3) O11 0.135(4) 0.152(5) 0.071(3) 0.007(3) 0.041(3) -0.027(3) C16 0.164(9) 0.256(13) 0.195(11) 0.055(10) -0.027(8) 0.109(9) C17 0.50(3) 0.110(7) 0.172(11) 0.005(7) -0.050(13) 0.123(12) C18 0.215(11) 0.248(12) 0.086(5) 0.016(7) 0.067(6) 0.087(9) C19 0.166(10) 0.361(19) 0.156(10) 0.076(11) 0.045(8) -0.070(11) N7 0.073(3) 0.067(3) 0.049(2) 0.0116(19) 0.0151(19) 0.008(2) _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 C1 O1 1.229(5) . ? C1 N1 1.356(6) . ? C1 N2 1.373(5) . ? C2 N1 1.393(5) . ? C2 C7 1.394(6) . ? C2 C3 1.407(6) . ? C3 C4 1.384(6) . ? C3 H3 0.9300 . ? C4 C5 1.375(7) . ? C4 N3 1.477(6) . ? C5 C6 1.376(7) . ? C5 H5 0.9300 . ? C6 C7 1.384(6) . ? C6 N4 1.474(6) . ? C7 H7 0.9300 . ? C8 C9 1.391(6) . ? C8 N2 1.392(5) . ? C8 C13 1.414(6) . ? C9 C10 1.391(6) . ? C9 H9 0.9300 . ? C10 C11 1.383(7) . ? C10 N5 1.481(7) . ? C11 C12 1.373(7) . ? C11 H11 0.9300 . ? C12 C13 1.380(6) . ? C12 N6 1.483(6) . ? C13 H13 0.9300 . ? N1 H1N 0.878(19) . ? N2 H2N 0.871(18) . ? N3 O3 1.224(5) . ? N3 O2 1.226(6) . ? N4 O5 1.198(6) . ? N4 O4 1.204(5) . ? N5 O6 1.211(6) . ? N5 O7 1.214(6) . ? N6 O8 1.218(6) . ? N6 O9 1.227(6) . ? C14 O11 1.216(7) . ? C14 O10 1.229(7) . ? C14 C15 1.474(9) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N7 1.467(9) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 N7 1.407(10) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 N7 1.428(8) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N7 1.431(11) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 O1 C1 N1 124.1(4) . . ? O1 C1 N2 123.4(4) . . ? N1 C1 N2 112.6(4) . . ? N1 C2 C7 125.1(4) . . ? N1 C2 C3 116.1(4) . . ? C7 C2 C3 118.7(4) . . ? C4 C3 C2 118.9(4) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 123.8(4) . . ? C5 C4 N3 118.2(4) . . ? C3 C4 N3 118.0(4) . . ? C4 C5 C6 115.5(4) . . ? C4 C5 H5 122.2 . . ? C6 C5 H5 122.2 . . ? C5 C6 C7 124.2(4) . . ? C5 C6 N4 117.8(4) . . ? C7 C6 N4 118.0(4) . . ? C6 C7 C2 118.8(4) . . ? C6 C7 H7 120.6 . . ? C2 C7 H7 120.6 . . ? C9 C8 N2 125.4(4) . . ? C9 C8 C13 118.5(4) . . ? N2 C8 C13 116.1(4) . . ? C8 C9 C10 119.4(4) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C11 C10 C9 123.1(5) . . ? C11 C10 N5 119.2(5) . . ? C9 C10 N5 117.7(4) . . ? C12 C11 C10 116.1(4) . . ? C12 C11 H11 121.9 . . ? C10 C11 H11 121.9 . . ? C11 C12 C13 123.6(4) . . ? C11 C12 N6 118.5(4) . . ? C13 C12 N6 117.9(5) . . ? C12 C13 C8 119.2(4) . . ? C12 C13 H13 120.4 . . ? C8 C13 H13 120.4 . . ? C1 N1 C2 127.4(4) . . ? C1 N1 H1N 118(3) . . ? C2 N1 H1N 114(3) . . ? C1 N2 C8 127.2(4) . . ? C1 N2 H2N 117(3) . . ? C8 N2 H2N 116(3) . . ? O3 N3 O2 124.0(5) . . ? O3 N3 C4 117.7(5) . . ? O2 N3 C4 118.3(4) . . ? O5 N4 O4 123.8(5) . . ? O5 N4 C6 118.7(4) . . ? O4 N4 C6 117.5(5) . . ? O6 N5 O7 123.3(5) . . ? O6 N5 C10 118.7(5) . . ? O7 N5 C10 118.0(5) . . ? O8 N6 O9 124.5(5) . . ? O8 N6 C12 118.0(5) . . ? O9 N6 C12 117.4(4) . . ? O11 C14 O10 125.4(6) . . ? O11 C14 C15 116.5(7) . . ? O10 C14 C15 118.1(6) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N7 C16 H16A 109.5 . . ? N7 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N7 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N7 C17 H17A 109.5 . . ? N7 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N7 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N7 C18 H18A 109.5 . . ? N7 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N7 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N7 C19 H19A 109.5 . . ? N7 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N7 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 N7 C18 113.1(8) . . ? C17 N7 C19 105.8(11) . . ? C18 N7 C19 107.8(7) . . ? C17 N7 C16 106.9(8) . . ? C18 N7 C16 116.1(7) . . ? C19 N7 C16 106.5(9) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.407 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.047 # Attachment '- FRE+ 30s.cif' data_Ros30s _database_code_depnum_ccdc_archive 'CCDC 855295' #TrackingRef '- FRE+ 30s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H23 N7 O11' _chemical_formula_weight 525.44 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.525(12) _cell_length_b 11.380(15) _cell_length_c 12.488(16) _cell_angle_alpha 107.619(15) _cell_angle_beta 97.507(10) _cell_angle_gamma 104.894(16) _cell_volume 1214(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2547 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.4 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 0.649 _exptl_absorpt_process_details REQAB _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'confocal mirrors' _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11747 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5265 _reflns_number_gt 3188 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. The urea H atoms were located from the difference map and refined with the bond distance restrained to 0.88A. ; _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^)+(0.1278P)^2^+0.2004P] 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 5265 _refine_ls_number_parameters 347 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1329 _refine_ls_R_factor_gt 0.0855 _refine_ls_wR_factor_ref 0.2674 _refine_ls_wR_factor_gt 0.2300 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 C1 C 0.2469(3) 0.4925(3) 0.4780(3) 0.0538(7) Uani 1 1 d . . . C2 C 0.0098(3) 0.3158(3) 0.4370(3) 0.0525(7) Uani 1 1 d . . . C3 C -0.0949(3) 0.2105(3) 0.3470(3) 0.0594(8) Uani 1 1 d . . . H3 H -0.0824 0.1913 0.2717 0.071 Uiso 1 1 calc R . . C4 C -0.2170(3) 0.1355(3) 0.3715(3) 0.0605(8) Uani 1 1 d . . . C5 C -0.2421(4) 0.1579(3) 0.4812(3) 0.0645(8) Uani 1 1 d . . . H5 H -0.3252 0.1069 0.4961 0.077 Uiso 1 1 calc R . . C6 C -0.1354(3) 0.2613(3) 0.5673(3) 0.0594(8) Uani 1 1 d . . . C7 C -0.0111(3) 0.3415(3) 0.5495(3) 0.0575(7) Uani 1 1 d . . . H7 H 0.0566 0.4106 0.6108 0.069 Uiso 1 1 calc R . . C8 C 0.4770(3) 0.6442(3) 0.4644(3) 0.0550(7) Uani 1 1 d . . . C9 C 0.5263(3) 0.7245(3) 0.5802(3) 0.0606(8) Uani 1 1 d . . . H9 H 0.4717 0.7095 0.6340 0.073 Uiso 1 1 calc R . . C10 C 0.6576(4) 0.8269(3) 0.6137(3) 0.0647(8) Uani 1 1 d . . . C11 C 0.7456(4) 0.8561(3) 0.5398(3) 0.0666(9) Uani 1 1 d . . . H11 H 0.8332 0.9258 0.5649 0.080 Uiso 1 1 calc R . . C12 C 0.6938(3) 0.7738(3) 0.4257(3) 0.0618(8) Uani 1 1 d . . . C13 C 0.5638(3) 0.6699(3) 0.3862(3) 0.0590(8) Uani 1 1 d . . . H13 H 0.5340 0.6174 0.3087 0.071 Uiso 1 1 calc R . . N1 N 0.1296(3) 0.3884(3) 0.4056(2) 0.0596(7) Uani 1 1 d D . . N2 N 0.3469(3) 0.5388(2) 0.4183(2) 0.0574(6) Uani 1 1 d D . . N3 N -0.3261(4) 0.0258(3) 0.2756(3) 0.0781(9) Uani 1 1 d . . . N4 N -0.1575(4) 0.2891(4) 0.6862(3) 0.0786(9) Uani 1 1 d . . . N5 N 0.7062(4) 0.9114(3) 0.7384(3) 0.0852(9) Uani 1 1 d . . . N6 N 0.7841(3) 0.7965(3) 0.3412(3) 0.0787(9) Uani 1 1 d . . . O1 O 0.2612(2) 0.5395(2) 0.58262(18) 0.0634(6) Uani 1 1 d . . . O2 O -0.3112(4) 0.0131(3) 0.1768(3) 0.1162(11) Uani 1 1 d . . . O3 O -0.4262(3) -0.0465(3) 0.2995(3) 0.1021(10) Uani 1 1 d . . . O4 O -0.2726(4) 0.2260(4) 0.7014(3) 0.1221(12) Uani 1 1 d . . . O5 O -0.0621(4) 0.3735(4) 0.7634(3) 0.1206(12) Uani 1 1 d . . . O6 O 0.6226(4) 0.8953(3) 0.8013(3) 0.1067(10) Uani 1 1 d . . . O7 O 0.8301(4) 0.9913(4) 0.7713(3) 0.1479(16) Uani 1 1 d . . . O8 O 0.8943(3) 0.8920(3) 0.3746(3) 0.1024(10) Uani 1 1 d . . . O9 O 0.7421(4) 0.7170(4) 0.2416(3) 0.1083(10) Uani 1 1 d . . . H1N H 0.126(4) 0.360(3) 0.3315(17) 0.074(10) Uiso 1 1 d D . . H2N H 0.324(3) 0.494(3) 0.3445(16) 0.057(9) Uiso 1 1 d D . . C14 C 0.1968(6) 0.3208(5) 0.1309(4) 0.0905(12) Uani 1 1 d . . . C15 C 0.1786(7) 0.2416(7) 0.0097(4) 0.156(3) Uani 1 1 d . . . H15A H 0.1681 0.1535 0.0034 0.234 Uiso 1 1 calc R . . H15B H 0.2647 0.2752 -0.0174 0.234 Uiso 1 1 calc R . . H15C H 0.0913 0.2445 -0.0361 0.234 Uiso 1 1 calc R . . O10 O 0.3175(4) 0.4057(4) 0.1820(3) 0.1161(11) Uani 1 1 d . . . O11 O 0.0907(5) 0.2952(4) 0.1740(3) 0.1412(15) Uani 1 1 d . . . C16 C 0.4321(9) 0.6657(9) 1.0424(7) 0.209(4) Uani 1 1 d . . . H16A H 0.5197 0.7393 1.0617 0.314 Uiso 1 1 calc R . . H16B H 0.4540 0.5878 1.0045 0.314 Uiso 1 1 calc R . . H16C H 0.4011 0.6613 1.1116 0.314 Uiso 1 1 calc R . . C17 C 0.3135(14) 0.8103(7) 1.0115(8) 0.262(6) Uani 1 1 d . . . H17A H 0.3999 0.8667 1.0002 0.392 Uiso 1 1 calc R . . H17B H 0.3159 0.8336 1.0924 0.392 Uiso 1 1 calc R . . H17C H 0.2251 0.8190 0.9725 0.392 Uiso 1 1 calc R . . C18 C 0.3102(9) 0.6352(8) 0.8445(5) 0.188(3) Uani 1 1 d . . . H18A H 0.2193 0.6366 0.8021 0.283 Uiso 1 1 calc R . . H18B H 0.3154 0.5482 0.8203 0.283 Uiso 1 1 calc R . . H18C H 0.3939 0.6914 0.8301 0.283 Uiso 1 1 calc R . . C19 C 0.1776(11) 0.6013(12) 0.9832(8) 0.261(6) Uani 1 1 d . . . H19A H 0.1792 0.6266 1.0641 0.392 Uiso 1 1 calc R . . H19B H 0.1708 0.5113 0.9535 0.392 Uiso 1 1 calc R . . H19C H 0.0929 0.6144 0.9434 0.392 Uiso 1 1 calc R . . N7 N 0.3131(3) 0.6792(3) 0.9660(2) 0.0711(8) Uani 1 1 d . . . 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 C1 0.0542(17) 0.0537(17) 0.0579(19) 0.0225(15) 0.0192(14) 0.0176(15) C2 0.0505(16) 0.0482(16) 0.0598(18) 0.0196(14) 0.0166(13) 0.0140(14) C3 0.0577(18) 0.0546(18) 0.0635(19) 0.0178(15) 0.0166(15) 0.0158(15) C4 0.0521(18) 0.0525(18) 0.072(2) 0.0208(16) 0.0089(15) 0.0120(15) C5 0.0512(18) 0.064(2) 0.081(2) 0.0327(18) 0.0166(16) 0.0130(16) C6 0.0540(18) 0.066(2) 0.0663(19) 0.0306(17) 0.0211(15) 0.0199(16) C7 0.0517(17) 0.0594(18) 0.0613(18) 0.0222(15) 0.0138(14) 0.0157(15) C8 0.0519(17) 0.0543(18) 0.0645(19) 0.0249(15) 0.0204(14) 0.0177(15) C9 0.0585(19) 0.0609(19) 0.066(2) 0.0247(16) 0.0244(15) 0.0171(16) C10 0.060(2) 0.0573(19) 0.071(2) 0.0179(16) 0.0129(16) 0.0159(16) C11 0.0523(18) 0.061(2) 0.090(3) 0.0357(19) 0.0176(17) 0.0123(15) C12 0.0537(18) 0.065(2) 0.082(2) 0.0397(18) 0.0277(16) 0.0225(16) C13 0.0572(18) 0.0637(19) 0.0669(19) 0.0300(15) 0.0254(15) 0.0230(16) N1 0.0595(16) 0.0586(16) 0.0551(16) 0.0168(13) 0.0237(13) 0.0080(13) N2 0.0561(15) 0.0571(15) 0.0531(16) 0.0153(12) 0.0208(12) 0.0089(13) N3 0.0674(19) 0.0641(19) 0.086(2) 0.0214(17) 0.0102(17) 0.0032(16) N4 0.0668(19) 0.097(2) 0.069(2) 0.0366(18) 0.0228(16) 0.0090(18) N5 0.080(2) 0.076(2) 0.082(2) 0.0167(18) 0.0146(18) 0.0106(19) N6 0.0647(19) 0.085(2) 0.106(3) 0.053(2) 0.0376(18) 0.0248(18) O1 0.0607(13) 0.0668(14) 0.0557(13) 0.0191(10) 0.0186(10) 0.0086(11) O2 0.112(2) 0.099(2) 0.085(2) 0.0075(17) 0.0134(18) -0.0184(18) O3 0.0806(19) 0.0836(19) 0.117(2) 0.0383(17) 0.0074(16) -0.0112(15) O4 0.097(2) 0.162(3) 0.096(2) 0.059(2) 0.0425(18) -0.005(2) O5 0.103(2) 0.150(3) 0.0709(19) 0.023(2) 0.0329(17) -0.011(2) O6 0.114(2) 0.100(2) 0.0790(19) 0.0096(16) 0.0286(18) 0.0113(18) O7 0.108(3) 0.144(3) 0.112(3) -0.003(2) 0.012(2) -0.031(2) O8 0.0713(17) 0.107(2) 0.142(3) 0.066(2) 0.0471(17) 0.0117(17) O9 0.105(2) 0.128(3) 0.093(2) 0.044(2) 0.0517(18) 0.0180(19) C14 0.100(3) 0.100(3) 0.066(2) 0.022(2) 0.028(2) 0.027(3) C15 0.161(5) 0.258(8) 0.075(3) 0.047(4) 0.064(3) 0.104(6) O10 0.098(2) 0.148(3) 0.081(2) 0.022(2) 0.0337(18) 0.019(2) O11 0.137(3) 0.152(3) 0.074(2) 0.0055(19) 0.043(2) -0.025(2) C16 0.162(6) 0.270(10) 0.198(8) 0.064(7) -0.012(6) 0.119(7) C17 0.463(18) 0.121(6) 0.155(7) 0.002(5) -0.030(9) 0.121(9) C18 0.224(8) 0.231(8) 0.089(4) 0.012(5) 0.066(5) 0.073(7) C19 0.194(8) 0.343(13) 0.140(6) 0.063(8) 0.051(6) -0.073(8) N7 0.0746(19) 0.0701(19) 0.0545(16) 0.0112(13) 0.0164(13) 0.0113(15) _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 C1 O1 1.226(4) . ? C1 N1 1.370(4) . ? C1 N2 1.382(4) . ? C2 C7 1.398(5) . ? C2 N1 1.402(4) . ? C2 C3 1.404(5) . ? C3 C4 1.384(4) . ? C3 H3 0.9300 . ? C4 C5 1.379(5) . ? C4 N3 1.475(5) . ? C5 C6 1.381(5) . ? C5 H5 0.9300 . ? C6 C7 1.386(4) . ? C6 N4 1.478(5) . ? C7 H7 0.9300 . ? C8 N2 1.392(4) . ? C8 C9 1.397(5) . ? C8 C13 1.408(4) . ? C9 C10 1.384(5) . ? C9 H9 0.9300 . ? C10 C11 1.381(5) . ? C10 N5 1.497(5) . ? C11 C12 1.387(5) . ? C11 H11 0.9300 . ? C12 C13 1.382(5) . ? C12 N6 1.485(5) . ? C13 H13 0.9300 . ? N1 H1N 0.876(18) . ? N2 H2N 0.872(18) . ? N3 O3 1.222(4) . ? N3 O2 1.230(5) . ? N4 O5 1.200(4) . ? N4 O4 1.218(4) . ? N5 O6 1.208(4) . ? N5 O7 1.218(4) . ? N6 O8 1.217(4) . ? N6 O9 1.237(5) . ? C14 O11 1.217(5) . ? C14 O10 1.236(5) . ? C14 C15 1.469(7) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N7 1.454(6) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 N7 1.426(7) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 N7 1.441(7) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N7 1.448(8) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 O1 C1 N1 124.5(3) . . ? O1 C1 N2 124.1(3) . . ? N1 C1 N2 111.4(3) . . ? C7 C2 N1 124.7(3) . . ? C7 C2 C3 119.1(3) . . ? N1 C2 C3 116.2(3) . . ? C4 C3 C2 119.3(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 123.4(3) . . ? C5 C4 N3 118.1(3) . . ? C3 C4 N3 118.4(3) . . ? C4 C5 C6 115.3(3) . . ? C4 C5 H5 122.3 . . ? C6 C5 H5 122.3 . . ? C5 C6 C7 124.7(3) . . ? C5 C6 N4 117.3(3) . . ? C7 C6 N4 118.0(3) . . ? C6 C7 C2 118.1(3) . . ? C6 C7 H7 120.9 . . ? C2 C7 H7 120.9 . . ? N2 C8 C9 125.2(3) . . ? N2 C8 C13 116.2(3) . . ? C9 C8 C13 118.6(3) . . ? C10 C9 C8 118.9(3) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C11 C10 C9 124.4(3) . . ? C11 C10 N5 118.3(3) . . ? C9 C10 N5 117.3(3) . . ? C10 C11 C12 115.1(3) . . ? C10 C11 H11 122.4 . . ? C12 C11 H11 122.4 . . ? C13 C12 C11 123.6(3) . . ? C13 C12 N6 117.9(3) . . ? C11 C12 N6 118.5(3) . . ? C12 C13 C8 119.4(3) . . ? C12 C13 H13 120.3 . . ? C8 C13 H13 120.3 . . ? C1 N1 C2 126.8(3) . . ? C1 N1 H1N 120(2) . . ? C2 N1 H1N 114(2) . . ? C1 N2 C8 126.7(3) . . ? C1 N2 H2N 114(2) . . ? C8 N2 H2N 119(2) . . ? O3 N3 O2 124.1(3) . . ? O3 N3 C4 117.8(4) . . ? O2 N3 C4 118.1(3) . . ? O5 N4 O4 123.0(3) . . ? O5 N4 C6 118.6(3) . . ? O4 N4 C6 118.4(3) . . ? O6 N5 O7 123.6(4) . . ? O6 N5 C10 118.8(3) . . ? O7 N5 C10 117.7(4) . . ? O8 N6 O9 124.4(3) . . ? O8 N6 C12 117.9(4) . . ? O9 N6 C12 117.7(3) . . ? O11 C14 O10 124.8(4) . . ? O11 C14 C15 116.6(5) . . ? O10 C14 C15 118.6(5) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N7 C16 H16A 109.5 . . ? N7 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N7 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N7 C17 H17A 109.5 . . ? N7 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N7 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N7 C18 H18A 109.5 . . ? N7 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N7 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N7 C19 H19A 109.5 . . ? N7 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N7 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 N7 C18 113.7(6) . . ? C17 N7 C19 105.7(8) . . ? C18 N7 C19 108.1(5) . . ? C17 N7 C16 107.0(6) . . ? C18 N7 C16 117.1(6) . . ? C19 N7 C16 104.3(7) . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.434 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.046