# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_contact_author_name 'Dr William Jones' _publ_contact_author_address ; Department of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email WJ10@CAM.AC.UK _publ_section_title ; Solvent-drop grinding: green polymorph control of cocrystallisation ; loop_ _publ_author_name 'William Jones' 'W. D. Samuel Motherwell' 'Andrew V. Trask' data_wj0314 _database_code_depnum_ccdc_archive 'CCDC 229592' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 N4 O2,C5 H8 O4' _chemical_formula_sum 'C13 H18 N4 O6' _chemical_formula_weight 326.31 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.0129(5) _cell_length_b 6.6017(2) _cell_length_c 17.1427(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.8360(10) _cell_angle_gamma 90.00 _cell_volume 1458.93(10) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5529 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.864 _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 refined successfully. ; _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 8983 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3343 _reflns_number_gt 2227 _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^)+(0.1443P)^2^+0.0681P] 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 3343 _refine_ls_number_parameters 217 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1061 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.2271 _refine_ls_wR_factor_gt 0.1870 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.001 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 O1 O 0.75722(16) 0.2502(2) 0.61283(12) 0.0351(5) Uani 1 1 d . . . O2 O 0.64785(15) 0.2128(3) 0.34746(11) 0.0388(5) Uani 1 1 d . . . N1 N 0.97818(17) 0.2546(2) 0.56884(12) 0.0232(5) Uani 1 1 d . . . N2 N 0.82182(17) 0.2262(3) 0.38563(12) 0.0256(5) Uani 1 1 d . . . N3 N 1.00426(17) 0.2420(2) 0.44276(13) 0.0250(5) Uani 1 1 d . . . C1 C 0.8813(2) 0.2457(3) 0.52377(14) 0.0225(5) Uani 1 1 d . . . C2 C 0.7200(2) 0.2231(3) 0.40053(15) 0.0278(6) Uani 1 1 d . . . C3 C 0.9007(2) 0.2383(3) 0.44738(14) 0.0216(5) Uani 1 1 d . . . N4 N 0.70356(17) 0.2304(3) 0.47960(13) 0.0265(5) Uani 1 1 d . . . C4 C 0.7795(2) 0.2433(3) 0.54567(15) 0.0250(5) Uani 1 1 d . . . C5 C 0.5944(2) 0.2276(4) 0.49342(19) 0.0368(6) Uani 1 1 d . . . H5A H 0.5911 0.2275 0.5502 0.055 Uiso 1 1 calc R . . H5B H 0.5605 0.1055 0.4697 0.055 Uiso 1 1 calc R . . H5C H 0.5588 0.3479 0.4696 0.055 Uiso 1 1 calc R . . C6 C 0.8438(2) 0.2300(4) 0.30456(15) 0.0343(6) Uani 1 1 d . . . H6A H 0.9190 0.2264 0.3041 0.052 Uiso 1 1 calc R . . H6B H 0.8153 0.3542 0.2788 0.052 Uiso 1 1 calc R . . H6C H 0.8118 0.1120 0.2763 0.052 Uiso 1 1 calc R . . C7 C 0.9998(2) 0.2627(4) 0.65448(15) 0.0323(6) Uani 1 1 d . . . H7A H 1.0750 0.2653 0.6706 0.048 Uiso 1 1 calc R . . H7B H 0.9703 0.1430 0.6769 0.048 Uiso 1 1 calc R . . H7C H 0.9687 0.3852 0.6735 0.048 Uiso 1 1 calc R . . C8 C 1.0479(2) 0.2527(3) 0.51841(15) 0.0251(5) Uani 1 1 d . . . H8 H 1.1207 0.2582 0.5343 0.030 Uiso 1 1 calc R . . O3 O 0.14409(17) 0.2632(3) 0.33744(11) 0.0408(5) Uani 1 1 d D . . H3 H 0.099(3) 0.249(4) 0.3792(18) 0.049 Uiso 1 1 d D . . O4 O 0.26061(17) 0.2531(3) 0.44487(12) 0.0392(5) Uani 1 1 d . . . O5 O 0.25313(15) 0.2060(3) 0.13807(12) 0.0441(5) Uani 1 1 d . . . O6 O 0.39602(15) 0.2246(3) 0.08039(11) 0.0347(5) Uani 1 1 d D . . H6 H 0.366(3) 0.247(4) 0.0273(12) 0.042 Uiso 1 1 d D . . C9 C 0.2406(2) 0.2777(4) 0.37461(17) 0.0352(6) Uani 1 1 d . . . C10 C 0.3199(2) 0.3239(4) 0.31979(17) 0.0428(7) Uani 1 1 d . . . H10A H 0.2862 0.4033 0.2744 0.051 Uiso 1 1 calc R . . H10B H 0.3761 0.4078 0.3481 0.051 Uiso 1 1 calc R . . C11 C 0.3661(2) 0.1341(4) 0.29004(15) 0.0388(7) Uani 1 1 d . . . H11A H 0.3106 0.0324 0.2766 0.047 Uiso 1 1 calc R . . H11B H 0.4173 0.0768 0.3323 0.047 Uiso 1 1 calc R . . C12 C 0.4195(2) 0.1752(5) 0.21735(15) 0.0379(6) Uani 1 1 d . . . H12A H 0.4633 0.2977 0.2272 0.046 Uiso 1 1 calc R . . H12B H 0.4660 0.0600 0.2100 0.046 Uiso 1 1 calc R . . C13 C 0.3470(2) 0.2051(4) 0.14311(15) 0.0300(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 O1 0.0307(11) 0.0492(11) 0.0277(10) -0.0015(7) 0.0122(8) -0.0013(7) O2 0.0266(11) 0.0563(11) 0.0321(11) 0.0025(8) -0.0012(8) -0.0035(8) N1 0.0206(11) 0.0285(10) 0.0207(11) -0.0017(6) 0.0031(8) 0.0000(7) N2 0.0215(11) 0.0340(10) 0.0213(10) -0.0005(7) 0.0029(8) -0.0010(7) N3 0.0222(11) 0.0284(10) 0.0248(11) 0.0004(7) 0.0051(9) 0.0003(7) C1 0.0195(12) 0.0246(11) 0.0234(12) 0.0010(7) 0.0030(10) 0.0010(8) C2 0.0258(14) 0.0299(12) 0.0279(13) 0.0020(9) 0.0042(11) -0.0012(9) C3 0.0207(12) 0.0221(11) 0.0223(12) 0.0004(7) 0.0037(9) 0.0007(8) N4 0.0186(11) 0.0324(11) 0.0290(12) 0.0017(7) 0.0050(9) -0.0010(7) C4 0.0238(13) 0.0243(11) 0.0277(13) 0.0010(8) 0.0068(10) 0.0001(8) C5 0.0178(13) 0.0509(16) 0.0429(16) 0.0024(11) 0.0088(12) -0.0028(10) C6 0.0317(15) 0.0512(15) 0.0209(13) -0.0005(9) 0.0064(11) 0.0001(11) C7 0.0276(15) 0.0455(15) 0.0232(13) -0.0005(9) 0.0014(10) 0.0007(10) C8 0.0208(12) 0.0271(12) 0.0286(13) -0.0021(8) 0.0071(10) 0.0004(8) O3 0.0297(11) 0.0700(14) 0.0230(10) -0.0007(7) 0.0044(8) 0.0033(8) O4 0.0321(12) 0.0606(13) 0.0245(11) 0.0007(7) 0.0027(8) 0.0012(8) O5 0.0197(10) 0.0826(14) 0.0296(11) 0.0027(9) 0.0023(8) -0.0007(9) O6 0.0235(11) 0.0585(11) 0.0234(10) 0.0006(7) 0.0078(8) -0.0011(7) C9 0.0317(15) 0.0456(15) 0.0289(14) -0.0022(10) 0.0069(11) 0.0046(11) C10 0.0471(18) 0.0436(15) 0.0397(16) -0.0032(12) 0.0127(14) -0.0038(13) C11 0.0367(16) 0.0441(15) 0.0354(15) 0.0033(11) 0.0040(12) 0.0037(11) C12 0.0269(14) 0.0582(17) 0.0292(14) -0.0027(11) 0.0056(11) 0.0058(12) C13 0.0244(13) 0.0387(13) 0.0277(13) -0.0021(9) 0.0062(10) 0.0003(10) _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 O1 C4 1.226(3) . ? O2 C2 1.217(3) . ? N1 C8 1.336(3) . ? N1 C1 1.387(3) . ? N1 C7 1.458(3) . ? N2 C3 1.373(3) . ? N2 C2 1.384(3) . ? N2 C6 1.457(3) . ? N3 C8 1.345(3) . ? N3 C3 1.361(3) . ? C1 C3 1.368(3) . ? C1 C4 1.425(4) . ? C2 N4 1.401(3) . ? N4 C4 1.401(3) . ? N4 C5 1.472(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8 0.9500 . ? O3 C9 1.332(4) . ? O3 H3 0.989(19) . ? O4 C9 1.208(3) . ? O5 C13 1.212(3) . ? O6 C13 1.329(3) . ? O6 H6 0.953(18) . ? C9 C10 1.518(4) . ? C10 C11 1.509(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.532(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.491(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? 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 C8 N1 C1 106.6(2) . . ? C8 N1 C7 126.7(2) . . ? C1 N1 C7 126.8(2) . . ? C3 N2 C2 119.5(2) . . ? C3 N2 C6 120.7(2) . . ? C2 N2 C6 119.6(2) . . ? C8 N3 C3 103.7(2) . . ? C3 C1 N1 105.2(2) . . ? C3 C1 C4 123.5(2) . . ? N1 C1 C4 131.3(2) . . ? O2 C2 N2 121.6(2) . . ? O2 C2 N4 121.4(2) . . ? N2 C2 N4 117.0(2) . . ? N3 C3 C1 111.6(2) . . ? N3 C3 N2 126.8(2) . . ? C1 C3 N2 121.6(2) . . ? C4 N4 C2 126.9(2) . . ? C4 N4 C5 117.4(2) . . ? C2 N4 C5 115.7(2) . . ? O1 C4 N4 122.0(2) . . ? O1 C4 C1 126.5(2) . . ? N4 C4 C1 111.5(2) . . ? N4 C5 H5A 109.5 . . ? N4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 N3 113.0(2) . . ? N1 C8 H8 123.5 . . ? N3 C8 H8 123.5 . . ? C9 O3 H3 106(2) . . ? C13 O6 H6 127(2) . . ? O4 C9 O3 121.9(3) . . ? O4 C9 C10 124.9(3) . . ? O3 C9 C10 113.2(2) . . ? C11 C10 C9 112.2(2) . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C10 C11 C12 112.0(2) . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C11 114.4(2) . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? C11 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? O5 C13 O6 122.1(2) . . ? O5 C13 C12 125.2(2) . . ? O6 C13 C12 112.7(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C1 C3 0.2(2) . . . . ? C7 N1 C1 C3 -179.36(18) . . . . ? C8 N1 C1 C4 180.00(19) . . . . ? C7 N1 C1 C4 0.5(3) . . . . ? C3 N2 C2 O2 179.94(19) . . . . ? C6 N2 C2 O2 3.9(3) . . . . ? C3 N2 C2 N4 -0.7(3) . . . . ? C6 N2 C2 N4 -176.71(18) . . . . ? C8 N3 C3 C1 -0.2(2) . . . . ? C8 N3 C3 N2 -179.46(18) . . . . ? N1 C1 C3 N3 0.0(2) . . . . ? C4 C1 C3 N3 -179.81(17) . . . . ? N1 C1 C3 N2 179.31(16) . . . . ? C4 C1 C3 N2 -0.5(3) . . . . ? C2 N2 C3 N3 179.72(18) . . . . ? C6 N2 C3 N3 -4.3(3) . . . . ? C2 N2 C3 C1 0.5(3) . . . . ? C6 N2 C3 C1 176.52(18) . . . . ? O2 C2 N4 C4 -179.72(19) . . . . ? N2 C2 N4 C4 0.9(3) . . . . ? O2 C2 N4 C5 -0.8(3) . . . . ? N2 C2 N4 C5 179.81(18) . . . . ? C2 N4 C4 O1 179.52(19) . . . . ? C5 N4 C4 O1 0.6(3) . . . . ? C2 N4 C4 C1 -0.8(3) . . . . ? C5 N4 C4 C1 -179.71(17) . . . . ? C3 C1 C4 O1 -179.76(19) . . . . ? N1 C1 C4 O1 0.5(3) . . . . ? C3 C1 C4 N4 0.6(3) . . . . ? N1 C1 C4 N4 -179.18(18) . . . . ? C1 N1 C8 N3 -0.3(2) . . . . ? C7 N1 C8 N3 179.20(17) . . . . ? C3 N3 C8 N1 0.3(2) . . . . ? O4 C9 C10 C11 87.5(3) . . . . ? O3 C9 C10 C11 -91.6(3) . . . . ? C9 C10 C11 C12 162.7(2) . . . . ? C10 C11 C12 C13 -75.5(3) . . . . ? C11 C12 C13 O5 2.7(4) . . . . ? C11 C12 C13 O6 -175.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.780 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.148 #======END data_wj0315 _database_code_depnum_ccdc_archive 'CCDC 229593' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 N4 O2,C5 H8 O4' _chemical_formula_sum 'C13 H18 N4 O6' _chemical_formula_weight 326.31 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 8.3212(8) _cell_length_b 8.6667(8) _cell_length_c 11.3636(12) _cell_angle_alpha 68.955(4) _cell_angle_beta 78.559(4) _cell_angle_gamma 74.236(4) _cell_volume 731.43(12) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 16876 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.743 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _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 5689 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3094 _reflns_number_gt 2262 _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^)+(0.1038P)^2^+0.0855P] 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 3094 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1771 _refine_ls_wR_factor_gt 0.1569 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.011 _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 O1 O 0.4406(2) 0.19460(19) 0.35801(15) 0.0366(4) Uani 1 1 d . . . O2 O 0.5148(2) 0.7377(2) 0.24219(15) 0.0408(4) Uani 1 1 d . . . N1 N 0.1909(2) 0.2766(2) 0.57794(16) 0.0296(4) Uani 1 1 d . . . N2 N 0.3295(2) 0.6547(2) 0.41596(17) 0.0309(4) Uani 1 1 d . . . N3 N 0.1356(2) 0.5346(2) 0.59654(16) 0.0304(4) Uani 1 1 d . . . N4 N 0.4793(2) 0.4663(2) 0.30269(16) 0.0315(4) Uani 1 1 d . . . C1 C 0.2896(3) 0.3706(3) 0.48025(19) 0.0278(5) Uani 1 1 d . . . C2 C 0.4449(3) 0.6274(3) 0.3153(2) 0.0312(5) Uani 1 1 d . . . C3 C 0.2528(3) 0.5272(3) 0.49523(19) 0.0280(5) Uani 1 1 d . . . C4 C 0.4051(3) 0.3289(3) 0.37999(19) 0.0301(5) Uani 1 1 d . . . C5 C 0.6012(3) 0.4398(3) 0.1947(2) 0.0401(6) Uani 1 1 d . . . H5A H 0.7110 0.4518 0.2047 0.060 Uiso 1 1 calc R . . H5B H 0.5627 0.5241 0.1156 0.060 Uiso 1 1 calc R . . H5C H 0.6109 0.3258 0.1921 0.060 Uiso 1 1 calc R . . C6 C 0.2866(3) 0.8206(3) 0.4331(2) 0.0347(5) Uani 1 1 d . . . H6A H 0.3840 0.8731 0.4024 0.052 Uiso 1 1 calc R . . H6B H 0.2544 0.8074 0.5234 0.052 Uiso 1 1 calc R . . H6C H 0.1925 0.8928 0.3851 0.052 Uiso 1 1 calc R . . C7 C 0.1858(3) 0.0997(3) 0.6046(2) 0.0375(5) Uani 1 1 d . . . H7A H 0.1057 0.0652 0.6796 0.056 Uiso 1 1 calc R . . H7B H 0.2978 0.0277 0.6205 0.056 Uiso 1 1 calc R . . H7C H 0.1505 0.0878 0.5316 0.056 Uiso 1 1 calc R . . C8 C 0.1021(3) 0.3798(3) 0.6431(2) 0.0310(5) Uani 1 1 d . . . H8 H 0.0232 0.3466 0.7150 0.037 Uiso 1 1 calc R . . O3 O 0.0515(2) 0.2440(2) 0.28304(16) 0.0391(4) Uani 1 1 d . . . H3 H -0.012(4) 0.319(4) 0.323(3) 0.047 Uiso 1 1 d . . . O4 O 0.1661(2) 0.4622(2) 0.16323(16) 0.0414(4) Uani 1 1 d . . . O5 O 0.1267(2) -0.1457(2) 0.16333(16) 0.0423(4) Uani 1 1 d . . . O6 O 0.2850(2) -0.2532(2) 0.01584(15) 0.0404(4) Uani 1 1 d . . . H6 H 0.255(4) -0.340(4) 0.056(3) 0.049 Uiso 1 1 d . . . C9 C 0.1590(3) 0.3145(3) 0.1895(2) 0.0318(5) Uani 1 1 d . . . C10 C 0.2623(3) 0.1974(3) 0.1191(2) 0.0333(5) Uani 1 1 d . . . H10A H 0.2967 0.0828 0.1802 0.040 Uiso 1 1 calc R . . H10B H 0.3652 0.2381 0.0743 0.040 Uiso 1 1 calc R . . C11 C 0.1621(3) 0.1882(3) 0.0225(2) 0.0352(5) Uani 1 1 d . . . H11A H 0.0476 0.1756 0.0633 0.042 Uiso 1 1 calc R . . H11B H 0.1513 0.2957 -0.0494 0.042 Uiso 1 1 calc R . . C12 C 0.2448(3) 0.0416(3) -0.0280(2) 0.0349(5) Uani 1 1 d . . . H12A H 0.2023 0.0648 -0.1095 0.042 Uiso 1 1 calc R . . H12B H 0.3675 0.0345 -0.0452 0.042 Uiso 1 1 calc R . . C13 C 0.2131(3) -0.1254(3) 0.0613(2) 0.0321(5) 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 O1 0.0418(9) 0.0320(8) 0.0381(9) -0.0196(7) 0.0024(7) -0.0054(7) O2 0.0470(10) 0.0376(9) 0.0378(9) -0.0112(7) 0.0052(7) -0.0176(8) N1 0.0325(10) 0.0279(9) 0.0301(9) -0.0130(7) 0.0017(7) -0.0082(7) N2 0.0342(10) 0.0281(9) 0.0316(9) -0.0142(7) 0.0031(7) -0.0078(8) N3 0.0338(10) 0.0297(9) 0.0284(9) -0.0135(7) 0.0031(8) -0.0074(8) N4 0.0339(10) 0.0335(10) 0.0282(9) -0.0143(7) 0.0035(7) -0.0082(8) C1 0.0277(10) 0.0294(10) 0.0279(10) -0.0123(8) -0.0005(8) -0.0066(8) C2 0.0311(11) 0.0348(11) 0.0291(11) -0.0122(9) -0.0002(9) -0.0091(9) C3 0.0312(11) 0.0277(10) 0.0272(10) -0.0125(8) -0.0010(8) -0.0066(8) C4 0.0325(11) 0.0309(11) 0.0291(10) -0.0138(9) -0.0032(9) -0.0052(9) C5 0.0430(13) 0.0480(14) 0.0300(11) -0.0198(10) 0.0095(10) -0.0109(11) C6 0.0439(13) 0.0254(10) 0.0374(12) -0.0145(9) -0.0011(10) -0.0081(9) C7 0.0448(13) 0.0282(11) 0.0401(12) -0.0140(9) 0.0050(10) -0.0120(10) C8 0.0326(11) 0.0315(10) 0.0295(11) -0.0139(9) 0.0021(9) -0.0063(9) O3 0.0427(10) 0.0322(8) 0.0435(9) -0.0195(7) 0.0097(7) -0.0108(7) O4 0.0509(10) 0.0282(8) 0.0449(10) -0.0146(7) 0.0044(8) -0.0117(7) O5 0.0508(10) 0.0390(9) 0.0390(9) -0.0193(7) 0.0135(8) -0.0169(8) O6 0.0498(10) 0.0350(9) 0.0393(9) -0.0195(7) 0.0100(8) -0.0143(8) C9 0.0344(11) 0.0288(10) 0.0334(11) -0.0105(9) -0.0029(9) -0.0086(9) C10 0.0351(12) 0.0302(11) 0.0337(11) -0.0122(9) 0.0026(9) -0.0081(9) C11 0.0428(13) 0.0310(11) 0.0325(11) -0.0121(9) -0.0049(10) -0.0065(10) C12 0.0425(13) 0.0365(12) 0.0288(11) -0.0143(9) 0.0009(9) -0.0119(10) C13 0.0313(11) 0.0367(12) 0.0333(11) -0.0185(9) 0.0006(9) -0.0088(9) _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 O1 C4 1.224(3) . ? O2 C2 1.217(3) . ? N1 C8 1.339(3) . ? N1 C1 1.386(3) . ? N1 C7 1.463(3) . ? N2 C3 1.371(3) . ? N2 C2 1.386(3) . ? N2 C6 1.459(3) . ? N3 C8 1.339(3) . ? N3 C3 1.362(3) . ? N4 C2 1.401(3) . ? N4 C4 1.416(3) . ? N4 C5 1.472(3) . ? C1 C3 1.373(3) . ? C1 C4 1.423(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8 0.9500 . ? O3 C9 1.325(3) . ? O3 H3 0.92(3) . ? O4 C9 1.221(3) . ? O5 C13 1.218(3) . ? O6 C13 1.335(3) . ? O6 H6 0.81(3) . ? C9 C10 1.498(3) . ? C10 C11 1.539(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.519(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.497(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? 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 C8 N1 C1 106.31(17) . . ? C8 N1 C7 126.97(18) . . ? C1 N1 C7 126.72(18) . . ? C3 N2 C2 119.51(17) . . ? C3 N2 C6 120.94(17) . . ? C2 N2 C6 119.52(18) . . ? C8 N3 C3 103.83(16) . . ? C2 N4 C4 126.87(17) . . ? C2 N4 C5 116.27(18) . . ? C4 N4 C5 116.82(17) . . ? C3 C1 N1 105.35(17) . . ? C3 C1 C4 123.20(19) . . ? N1 C1 C4 131.44(18) . . ? O2 C2 N2 121.6(2) . . ? O2 C2 N4 121.5(2) . . ? N2 C2 N4 116.92(18) . . ? N3 C3 N2 126.61(18) . . ? N3 C3 C1 111.32(18) . . ? N2 C3 C1 122.07(19) . . ? O1 C4 N4 121.53(19) . . ? O1 C4 C1 127.1(2) . . ? N4 C4 C1 111.37(17) . . ? N4 C5 H5A 109.5 . . ? N4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 N3 113.19(18) . . ? N1 C8 H8 123.4 . . ? N3 C8 H8 123.4 . . ? C9 O3 H3 111.4(17) . . ? C13 O6 H6 114(2) . . ? O4 C9 O3 121.9(2) . . ? O4 C9 C10 124.9(2) . . ? O3 C9 C10 113.24(18) . . ? C9 C10 C11 110.91(19) . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 112.5(2) . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 113.28(18) . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? O5 C13 O6 122.1(2) . . ? O5 C13 C12 125.0(2) . . ? O6 C13 C12 112.90(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C1 C3 0.6(2) . . . . ? C7 N1 C1 C3 -179.1(2) . . . . ? C8 N1 C1 C4 -178.2(2) . . . . ? C7 N1 C1 C4 2.0(4) . . . . ? C3 N2 C2 O2 179.4(2) . . . . ? C6 N2 C2 O2 1.8(3) . . . . ? C3 N2 C2 N4 -1.5(3) . . . . ? C6 N2 C2 N4 -179.12(18) . . . . ? C4 N4 C2 O2 -179.0(2) . . . . ? C5 N4 C2 O2 -1.4(3) . . . . ? C4 N4 C2 N2 1.9(3) . . . . ? C5 N4 C2 N2 179.5(2) . . . . ? C8 N3 C3 N2 -179.3(2) . . . . ? C8 N3 C3 C1 0.2(2) . . . . ? C2 N2 C3 N3 -179.0(2) . . . . ? C6 N2 C3 N3 -1.4(3) . . . . ? C2 N2 C3 C1 1.6(3) . . . . ? C6 N2 C3 C1 179.3(2) . . . . ? N1 C1 C3 N3 -0.5(2) . . . . ? C4 C1 C3 N3 178.5(2) . . . . ? N1 C1 C3 N2 179.0(2) . . . . ? C4 C1 C3 N2 -2.1(3) . . . . ? C2 N4 C4 O1 177.6(2) . . . . ? C5 N4 C4 O1 0.0(3) . . . . ? C2 N4 C4 C1 -2.1(3) . . . . ? C5 N4 C4 C1 -179.7(2) . . . . ? C3 C1 C4 O1 -177.6(2) . . . . ? N1 C1 C4 O1 1.1(4) . . . . ? C3 C1 C4 N4 2.1(3) . . . . ? N1 C1 C4 N4 -179.2(2) . . . . ? C1 N1 C8 N3 -0.6(2) . . . . ? C7 N1 C8 N3 179.2(2) . . . . ? C3 N3 C8 N1 0.3(2) . . . . ? O4 C9 C10 C11 -97.6(3) . . . . ? O3 C9 C10 C11 80.1(2) . . . . ? C9 C10 C11 C12 -166.37(18) . . . . ? C10 C11 C12 C13 79.3(2) . . . . ? C11 C12 C13 O5 1.9(3) . . . . ? C11 C12 C13 O6 179.52(19) . . . . ? _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.921 _refine_diff_density_max 0.356 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.111