# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_wj1098 _database_code_depnum_ccdc_archive 'CCDC 901279' #TrackingRef '13923_web_deposit_cif_file_0_MarkD.Eddleston_1347467322.Cocrystal Form II wj1098.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N2, C5 H6 O4' _chemical_formula_sum 'C17 H14 N2 O4' _chemical_formula_weight 310.30 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 orthorhombic _symmetry_space_group_name_H-M Pna2(1) _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 16.5230(1) _cell_length_b 15.9952(3) _cell_length_c 5.4792(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1448.09(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9988 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.915 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atoms were located and their positions were refined satisfactorily. 1444 Friedel pairs were averaged for the refinement. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 13464 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 30.03 _reflns_number_total 2316 _reflns_number_gt 2069 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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. ; _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^)+(0.0552P)^2^+0.2306P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(11) _refine_ls_number_reflns 2316 _refine_ls_number_parameters 215 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 N1 N 0.20001(8) 0.69243(9) 0.8614(3) 0.0257(3) Uani 1 1 d . . . N2 N 0.10213(8) 0.71698(9) 0.4423(3) 0.0260(3) Uani 1 1 d . . . O1 O 0.33497(10) 0.77620(8) -0.6762(3) 0.0483(4) Uani 1 1 d . . . O2 O 0.29818(8) 0.64423(8) -0.7407(3) 0.0357(3) Uani 1 1 d . . . H2 H 0.2679(15) 0.6676(15) -0.843(5) 0.043 Uiso 1 1 d . . . O3 O 0.48619(10) 0.64611(9) 0.0379(3) 0.0441(4) Uani 1 1 d . . . O4 O 0.50890(8) 0.78389(8) 0.0193(3) 0.0360(3) Uani 1 1 d . . . H4 H 0.5408(15) 0.7749(14) 0.149(6) 0.043 Uiso 1 1 d . . . C1 C 0.33997(9) 0.70314(10) -0.6255(3) 0.0272(3) Uani 1 1 d . . . C2 C 0.39332(9) 0.67022(11) -0.4250(3) 0.0263(3) Uani 1 1 d . . . C3 C 0.42313(10) 0.72833(11) -0.2752(3) 0.0285(3) Uani 1 1 d . . . H3 H 0.4096 0.7848 -0.3098 0.034 Uiso 1 1 calc R . . C4 C 0.47551(10) 0.71299(11) -0.0597(3) 0.0290(3) Uani 1 1 d . . . C5 C 0.40770(13) 0.57801(11) -0.4151(4) 0.0387(4) Uani 1 1 d . . . H5A H 0.4498 0.5658 -0.2941 0.058 Uiso 1 1 calc R . . H5B H 0.4253 0.5582 -0.5758 0.058 Uiso 1 1 calc R . . H5C H 0.3575 0.5495 -0.3688 0.058 Uiso 1 1 calc R . . C6 C 0.18758(9) 0.76944(10) 0.7683(3) 0.0249(3) Uani 1 1 d . . . C7 C 0.22455(10) 0.83993(10) 0.8814(4) 0.0289(3) Uani 1 1 d . . . H7 H 0.2594 0.8325 1.0175 0.035 Uiso 1 1 calc R . . C8 C 0.20961(10) 0.91789(11) 0.7934(4) 0.0314(4) Uani 1 1 d . . . H8 H 0.2339 0.9649 0.8701 0.038 Uiso 1 1 calc R . . C9 C 0.15804(11) 0.93029(11) 0.5874(4) 0.0318(4) Uani 1 1 d . . . H9 H 0.1479 0.9855 0.5313 0.038 Uiso 1 1 calc R . . C10 C 0.12323(10) 0.86483(11) 0.4705(4) 0.0299(4) Uani 1 1 d . . . H10 H 0.0897 0.8741 0.3322 0.036 Uiso 1 1 calc R . . C11 C 0.13721(9) 0.78198(10) 0.5563(3) 0.0240(3) Uani 1 1 d . . . C12 C 0.11407(9) 0.64030(10) 0.5364(3) 0.0256(3) Uani 1 1 d . . . C13 C 0.07694(11) 0.56962(11) 0.4231(4) 0.0327(4) Uani 1 1 d . . . H13 H 0.0449 0.5768 0.2808 0.039 Uiso 1 1 calc R . . C14 C 0.08764(12) 0.49190(11) 0.5198(4) 0.0363(4) Uani 1 1 d . . . H14 H 0.0630 0.4451 0.4431 0.044 Uiso 1 1 calc R . . C15 C 0.13503(11) 0.47965(11) 0.7337(4) 0.0361(4) Uani 1 1 d . . . H15 H 0.1410 0.4250 0.7993 0.043 Uiso 1 1 calc R . . C16 C 0.17191(10) 0.54556(10) 0.8451(4) 0.0315(4) Uani 1 1 d . . . H16 H 0.2037 0.5366 0.9871 0.038 Uiso 1 1 calc R . . C17 C 0.16292(9) 0.62782(10) 0.7496(3) 0.0257(3) 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 N1 0.0248(6) 0.0291(6) 0.0230(7) 0.0024(6) -0.0018(5) 0.0012(5) N2 0.0247(6) 0.0312(6) 0.0222(7) 0.0014(6) -0.0024(5) 0.0000(5) O1 0.0646(10) 0.0315(6) 0.0489(10) 0.0030(7) -0.0307(8) -0.0004(6) O2 0.0374(6) 0.0359(6) 0.0337(7) 0.0048(6) -0.0149(6) -0.0050(5) O3 0.0569(8) 0.0398(7) 0.0356(9) 0.0068(7) -0.0205(7) -0.0043(6) O4 0.0378(7) 0.0399(6) 0.0304(7) 0.0004(6) -0.0114(6) -0.0040(5) C1 0.0259(7) 0.0336(8) 0.0220(8) 0.0023(6) -0.0019(6) -0.0008(6) C2 0.0236(7) 0.0333(8) 0.0221(7) 0.0043(7) -0.0014(6) -0.0020(6) C3 0.0274(7) 0.0339(8) 0.0240(8) 0.0026(7) -0.0043(7) 0.0001(6) C4 0.0253(7) 0.0394(9) 0.0223(8) 0.0009(7) -0.0022(6) -0.0002(6) C5 0.0481(10) 0.0308(8) 0.0374(10) 0.0076(8) -0.0149(9) -0.0046(8) C6 0.0229(7) 0.0298(7) 0.0220(8) 0.0017(7) -0.0018(6) 0.0011(5) C7 0.0290(7) 0.0323(8) 0.0255(8) 0.0004(7) -0.0059(7) -0.0009(6) C8 0.0337(8) 0.0302(7) 0.0304(9) -0.0001(7) -0.0064(7) -0.0037(6) C9 0.0361(8) 0.0300(7) 0.0293(9) 0.0053(7) -0.0034(7) -0.0008(7) C10 0.0295(7) 0.0326(8) 0.0275(9) 0.0063(7) -0.0052(7) 0.0009(6) C11 0.0225(6) 0.0300(7) 0.0195(8) 0.0018(6) -0.0002(6) -0.0005(5) C12 0.0243(7) 0.0293(7) 0.0230(8) -0.0002(7) 0.0021(6) -0.0004(5) C13 0.0338(8) 0.0353(8) 0.0289(9) -0.0034(7) -0.0014(7) -0.0052(7) C14 0.0405(9) 0.0302(8) 0.0382(11) -0.0063(8) 0.0066(8) -0.0056(7) C15 0.0406(9) 0.0274(8) 0.0402(10) 0.0024(8) 0.0084(9) 0.0028(7) C16 0.0328(8) 0.0308(8) 0.0309(9) 0.0041(7) 0.0036(7) 0.0046(6) C17 0.0228(7) 0.0294(7) 0.0248(8) 0.0021(7) 0.0021(6) 0.0020(5) _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 N1 C17 1.349(2) . ? N1 C6 1.349(2) . ? N2 C11 1.344(2) . ? N2 C12 1.345(2) . ? O1 C1 1.204(2) . ? O2 C1 1.328(2) . ? O2 H2 0.84(3) . ? O3 C4 1.209(2) . ? O4 C4 1.333(2) . ? O4 H4 0.90(3) . ? C1 C2 1.504(2) . ? C2 C3 1.334(2) . ? C2 C5 1.495(2) . ? C3 C4 1.485(2) . ? C3 H3 0.9500 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.424(2) . ? C6 C11 1.443(2) . ? C7 C8 1.360(2) . ? C7 H7 0.9500 . ? C8 C9 1.428(3) . ? C8 H8 0.9500 . ? C9 C10 1.356(3) . ? C9 H9 0.9500 . ? C10 C11 1.425(2) . ? C10 H10 0.9500 . ? C12 C13 1.428(2) . ? C12 C17 1.434(2) . ? C13 C14 1.363(3) . ? C13 H13 0.9500 . ? C14 C15 1.423(3) . ? C14 H14 0.9500 . ? C15 C16 1.362(3) . ? C15 H15 0.9500 . ? C16 C17 1.424(2) . ? C16 H16 0.9500 . ? 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 C17 N1 C6 117.30(14) . . ? C11 N2 C12 117.66(14) . . ? C1 O2 H2 108.1(17) . . ? C4 O4 H4 111.4(15) . . ? O1 C1 O2 122.92(16) . . ? O1 C1 C2 123.27(15) . . ? O2 C1 C2 113.81(14) . . ? C3 C2 C5 127.33(16) . . ? C3 C2 C1 114.95(15) . . ? C5 C2 C1 117.72(15) . . ? C2 C3 C4 126.11(16) . . ? C2 C3 H3 116.9 . . ? C4 C3 H3 116.9 . . ? O3 C4 O4 123.27(17) . . ? O3 C4 C3 125.68(16) . . ? O4 C4 C3 111.04(15) . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 119.53(15) . . ? N1 C6 C11 121.28(14) . . ? C7 C6 C11 119.19(15) . . ? C8 C7 C6 119.59(16) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 121.08(16) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C8 121.30(17) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 119.57(16) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? N2 C11 C10 119.75(15) . . ? N2 C11 C6 121.01(14) . . ? C10 C11 C6 119.23(14) . . ? N2 C12 C13 119.50(16) . . ? N2 C12 C17 121.45(15) . . ? C13 C12 C17 119.05(15) . . ? C14 C13 C12 119.84(18) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 121.14(17) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C16 C15 C14 120.58(17) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 120.25(18) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? N1 C17 C16 119.59(16) . . ? N1 C17 C12 121.27(14) . . ? C16 C17 C12 119.13(15) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.215 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.037 data_wj10112 _database_code_depnum_ccdc_archive 'CCDC 901280' #TrackingRef '13924_web_deposit_cif_file_1_MarkD.Eddleston_1347467322.Cocrystal Monohydrate wj10112.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N2, C5 H6 O4, H2 O' _chemical_formula_sum 'C17 H16 N2 O5' _chemical_formula_weight 328.32 _chemical_absolute_configuration ; 335 Friedel pairs were averaged for the refinement. ; 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 orthorhombic _symmetry_space_group_name_H-M Pna2(1) _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 27.495(2) _cell_length_b 14.043(2) _cell_length_c 4.0898(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1579.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 22672 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 22.46 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.797 _exptl_absorpt_correction_T_max 1.629 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The crystals did not diffract well (theta(max)=22.5deg). Nevertheless, the -COOH and water hydrogen atoms were located and their positions were refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 3223 _diffrn_reflns_av_R_equivalents 0.0814 _diffrn_reflns_av_sigmaI/netI 0.0738 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -3 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 22.45 _reflns_number_total 1163 _reflns_number_gt 878 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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. ; _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^)+(0.0419P)^2^+0.1788P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(3) _refine_ls_number_reflns 1163 _refine_ls_number_parameters 225 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.059 _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 N1 N 0.29055(12) 0.1200(3) 0.5448(12) 0.0386(11) Uani 1 1 d . . . N2 N 0.38837(12) 0.0885(3) 0.3677(13) 0.0409(11) Uani 1 1 d . . . C6 C 0.32632(16) 0.1788(3) 0.6539(15) 0.0401(15) Uani 1 1 d . . . C7 C 0.31501(17) 0.2575(3) 0.8569(17) 0.0462(14) Uani 1 1 d . . . H7 H 0.2824 0.2681 0.9233 0.055 Uiso 1 1 calc R . . C8 C 0.35043(18) 0.3174(4) 0.9565(15) 0.0507(17) Uani 1 1 d . . . H8 H 0.3425 0.3706 1.0896 0.061 Uiso 1 1 calc R . . C9 C 0.39961(19) 0.3014(4) 0.8636(17) 0.0500(15) Uani 1 1 d . . . H9 H 0.4241 0.3443 0.9355 0.060 Uiso 1 1 calc R . . C10 C 0.41198(17) 0.2269(4) 0.6765(16) 0.0491(16) Uani 1 1 d . . . H10 H 0.4451 0.2168 0.6212 0.059 Uiso 1 1 calc R . . C11 C 0.37590(15) 0.1629(3) 0.5600(17) 0.0429(14) Uani 1 1 d . . . C12 C 0.35317(16) 0.0315(3) 0.2618(15) 0.0385(14) Uani 1 1 d . . . C13 C 0.36430(17) -0.0474(3) 0.0630(16) 0.0457(15) Uani 1 1 d . . . H13 H 0.3972 -0.0597 0.0048 0.055 Uiso 1 1 calc R . . C14 C 0.32843(18) -0.1064(4) -0.0471(16) 0.0498(16) Uani 1 1 d . . . H14 H 0.3364 -0.1590 -0.1832 0.060 Uiso 1 1 calc R . . C15 C 0.27919(18) -0.0896(4) 0.0409(16) 0.0497(15) Uani 1 1 d . . . H15 H 0.2546 -0.1315 -0.0352 0.060 Uiso 1 1 calc R . . C16 C 0.26695(16) -0.0150(3) 0.2306(16) 0.0425(14) Uani 1 1 d . . . H16 H 0.2338 -0.0041 0.2833 0.051 Uiso 1 1 calc R . . C17 C 0.30292(15) 0.0471(3) 0.3515(15) 0.0379(13) Uani 1 1 d . . . C1 C 0.54162(19) 0.2872(4) 0.1291(17) 0.0489(16) Uani 1 1 d . . . O1 O 0.55079(12) 0.1965(3) 0.0499(13) 0.0633(12) Uani 1 1 d . . . H1 H 0.5325 0.1604 0.1584 0.076 Uiso 1 1 calc R . . C2 C 0.58061(18) 0.3559(4) 0.0174(16) 0.0463(15) Uani 1 1 d . . . O2 O 0.50649(13) 0.3124(3) 0.2733(15) 0.0709(14) Uani 1 1 d . . . C3 C 0.62029(16) 0.3199(4) -0.1142(17) 0.0451(14) Uani 1 1 d . . . H3 H 0.6217 0.2527 -0.1388 0.054 Uiso 1 1 calc R . . O3 O 0.66569(12) 0.4599(3) -0.2744(16) 0.0728(16) Uani 1 1 d . . . C4 C 0.66343(15) 0.3760(4) -0.2285(17) 0.0467(16) Uani 1 1 d . . . O4 O 0.70051(11) 0.3190(2) -0.2661(15) 0.0705(16) Uani 1 1 d . . . H4 H 0.7245 0.3501 -0.3351 0.085 Uiso 1 1 calc R . . C5 C 0.57032(19) 0.4581(4) 0.084(2) 0.0588(18) Uani 1 1 d . . . H5A H 0.5994 0.4961 0.0358 0.088 Uiso 1 1 calc R . . H5B H 0.5614 0.4661 0.3142 0.088 Uiso 1 1 calc R . . H5C H 0.5434 0.4795 -0.0549 0.088 Uiso 1 1 calc R . . O1W O 0.51298(11) -0.0599(2) -0.2795(12) 0.0488(11) Uani 1 1 d D . . H1W H 0.5420(15) -0.067(3) -0.250(15) 0.059 Uiso 1 1 d D . . H2W H 0.5003(17) -0.029(4) -0.140(14) 0.059 Uiso 1 1 d 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 N1 0.0330(19) 0.038(2) 0.045(3) 0.012(3) 0.003(2) 0.0040(19) N2 0.034(2) 0.038(2) 0.051(3) 0.014(3) 0.007(2) 0.0035(19) C6 0.035(2) 0.036(3) 0.049(4) 0.017(3) 0.001(2) 0.004(2) C7 0.044(3) 0.041(3) 0.054(4) 0.009(3) 0.004(3) 0.010(3) C8 0.053(3) 0.048(3) 0.051(5) 0.008(3) 0.001(3) 0.001(3) C9 0.053(3) 0.043(3) 0.053(4) 0.015(3) -0.013(3) -0.008(3) C10 0.039(3) 0.049(3) 0.059(5) 0.015(4) 0.004(3) -0.002(2) C11 0.034(3) 0.042(3) 0.054(4) 0.014(3) 0.000(3) 0.000(2) C12 0.037(3) 0.034(3) 0.045(4) 0.009(3) 0.006(3) 0.004(2) C13 0.043(3) 0.044(3) 0.050(4) 0.013(3) 0.007(3) 0.003(2) C14 0.060(3) 0.044(3) 0.045(4) 0.014(3) 0.009(3) 0.005(3) C15 0.051(3) 0.052(4) 0.046(4) 0.011(4) 0.003(3) -0.005(3) C16 0.036(3) 0.044(3) 0.047(4) 0.013(3) 0.001(3) -0.001(2) C17 0.032(2) 0.036(3) 0.046(4) 0.012(3) 0.009(3) 0.003(2) C1 0.036(3) 0.049(3) 0.062(5) 0.007(3) -0.006(3) -0.003(2) O1 0.0471(19) 0.056(3) 0.086(3) 0.006(2) 0.020(2) -0.0104(17) C2 0.046(3) 0.045(3) 0.048(4) 0.003(3) -0.003(3) 0.000(2) O2 0.046(2) 0.070(3) 0.097(4) -0.002(3) 0.017(3) -0.007(2) C3 0.032(2) 0.047(3) 0.056(4) -0.005(3) 0.003(3) 0.000(2) O3 0.0420(18) 0.052(2) 0.124(5) 0.018(3) 0.019(3) 0.0041(17) C4 0.033(3) 0.047(3) 0.061(5) 0.012(3) 0.001(3) -0.002(2) O4 0.0409(19) 0.046(2) 0.124(5) 0.001(3) 0.023(3) -0.0064(17) C5 0.054(3) 0.046(3) 0.076(5) -0.005(3) 0.009(4) 0.002(3) O1W 0.0300(16) 0.050(2) 0.066(3) -0.005(2) -0.005(2) 0.0010(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 N1 C17 1.337(7) . ? N1 C6 1.360(6) . ? N2 C12 1.328(6) . ? N2 C11 1.352(7) . ? C6 C7 1.417(8) . ? C6 C11 1.434(7) . ? C7 C8 1.350(7) . ? C7 H7 0.9500 . ? C8 C9 1.422(8) . ? C8 H8 0.9500 . ? C9 C10 1.341(8) . ? C9 H9 0.9500 . ? C10 C11 1.421(7) . ? C10 H10 0.9500 . ? C12 C13 1.408(7) . ? C12 C17 1.446(6) . ? C13 C14 1.365(7) . ? C13 H13 0.9500 . ? C14 C15 1.421(7) . ? C14 H14 0.9500 . ? C15 C16 1.346(8) . ? C15 H15 0.9500 . ? C16 C17 1.408(7) . ? C16 H16 0.9500 . ? C1 O2 1.186(7) . ? C1 O1 1.338(7) . ? C1 C2 1.513(7) . ? O1 H1 0.8400 . ? C2 C3 1.317(7) . ? C2 C5 1.488(7) . ? C3 C4 1.499(7) . ? C3 H3 0.9500 . ? O3 C4 1.194(6) . ? C4 O4 1.305(6) . ? O4 H4 0.8400 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? O1W H1W 0.81(4) . ? O1W H2W 0.80(4) . ? 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 C17 N1 C6 118.4(4) . . ? C12 N2 C11 118.1(4) . . ? N1 C6 C7 120.5(4) . . ? N1 C6 C11 120.3(5) . . ? C7 C6 C11 119.2(4) . . ? C8 C7 C6 120.3(5) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 120.5(5) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 121.1(5) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.5(5) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? N2 C11 C10 120.4(4) . . ? N2 C11 C6 121.2(4) . . ? C10 C11 C6 118.4(5) . . ? N2 C12 C13 120.3(4) . . ? N2 C12 C17 121.5(5) . . ? C13 C12 C17 118.2(4) . . ? C14 C13 C12 120.8(5) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 120.2(6) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 120.9(5) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 120.6(5) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? N1 C17 C16 120.2(4) . . ? N1 C17 C12 120.6(4) . . ? C16 C17 C12 119.2(5) . . ? O2 C1 O1 123.9(5) . . ? O2 C1 C2 122.5(5) . . ? O1 C1 C2 113.6(5) . . ? C1 O1 H1 109.5 . . ? C3 C2 C5 127.0(5) . . ? C3 C2 C1 117.8(5) . . ? C5 C2 C1 115.2(5) . . ? C2 C3 C4 125.5(5) . . ? C2 C3 H3 117.2 . . ? C4 C3 H3 117.2 . . ? O3 C4 O4 123.1(4) . . ? O3 C4 C3 127.5(4) . . ? O4 C4 C3 109.4(4) . . ? C4 O4 H4 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? H1W O1W H2W 113(4) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 22.45 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.147 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.037