Supplementary Material (ESI) for CrystEngComm This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'P.THOMAS MUTHIAH' _publ_contact_author_address ; Department of Chemistry Bharathidasan University Tiruchirappalli-620024 India ; _publ_contact_author_email tommtrichy@yahoo.co.in _publ_contact_author_fax 0431-660245 _publ_contact_author_phone 0431-660353 #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Pseudo-polymorphism and crystal engineering: Hydrogen-bonded networks in trimethoprim m-chlorobenzoate and trimethoprim m-chlorobenzoate dihydrate ; loop_ _publ_author_name _publ_author_address 'Savarimuthu Baskar Raj' ; Department of Chemistry Bharathidasan University Tiruchirappalli-620024 India ; 'Packianathan Thomas Muthiah' ; Department of Chemistry Bharathidasan University Tiruchirappalli-620024 India ; 'Urszula Rychlewska' ; Faculty of Chemistry Adam Mickiewicz University Grunwaldzka 6 60-780 Poznan Poland ; B.Warzajtis ; Faculty of Chemistry Adam Mickiewicz University Grunwaldzka 6 60-780 Poznan Poland ; #=============================================================================== data_tmpm _database_code_CSD 194298 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H19 N4 O3, C7 H4 O2 Cl' _chemical_formula_sum 'C21 H23 Cl N4 O5' _chemical_formula_weight 446.88 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.545(10) _cell_length_b 28.280(6) _cell_length_c 11.633(2) _cell_angle_alpha 90.000(3) _cell_angle_beta 103.37(3) _cell_angle_gamma 90.000(3) _cell_volume 2095(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6655 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD \k-geometry diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number '5 reference frames' _diffrn_standards_interval_count 'every 50 dc frames' _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10353 _diffrn_reflns_av_R_equivalents 0.0664 _diffrn_reflns_av_sigmaI/netI 0.0620 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 25.06 _reflns_number_total 3682 _reflns_number_gt 3207 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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. ; _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^)+(0.1000P)^2^+0.0000P] 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 3682 _refine_ls_number_parameters 372 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1062 _refine_ls_R_factor_gt 0.0817 _refine_ls_wR_factor_ref 0.1935 _refine_ls_wR_factor_gt 0.1836 _refine_ls_goodness_of_fit_ref 1.334 _refine_ls_restrained_S_all 1.334 _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 Cl1 Cl 0.84498(19) -0.11315(4) 0.64138(9) 0.0455(4) Uani 1 1 d . . . O1 O 0.5201(3) 0.25313(8) 0.3136(2) 0.0242(6) Uani 1 1 d . . . O2 O 0.2037(3) 0.31547(8) 0.27601(19) 0.0200(5) Uani 1 1 d . . . O3 O -0.1571(3) 0.29790(8) 0.1229(2) 0.0242(6) Uani 1 1 d . . . O4 O 0.6711(4) -0.01799(9) 0.2369(2) 0.0275(6) Uani 1 1 d . . . N1 N 0.5188(4) 0.05005(10) 0.0861(2) 0.0182(6) Uani 1 1 d . . . N3 N 0.5502(4) 0.10138(10) -0.0695(2) 0.0187(6) Uani 1 1 d . . . O5 O 0.9675(5) -0.01980(12) 0.1727(2) 0.0454(8) Uani 1 1 d . . . N2 N 0.7841(4) 0.04038(10) -0.0113(3) 0.0208(7) Uani 1 1 d . . . N4 N 0.3147(5) 0.16075(11) -0.1280(3) 0.0251(7) Uani 1 1 d . . . C13 C -0.0403(5) 0.21913(12) 0.0801(3) 0.0183(7) Uani 1 1 d . . . C4 C 0.3789(5) 0.12399(11) -0.0557(3) 0.0183(7) Uani 1 1 d . . . C5 C 0.2653(5) 0.11084(11) 0.0307(3) 0.0173(7) Uani 1 1 d . . . C2 C 0.6170(5) 0.06433(12) 0.0006(3) 0.0184(7) Uani 1 1 d . . . C22 C 0.8715(6) -0.06759(13) 0.4408(3) 0.0274(8) Uani 1 1 d . . . C21 C 0.9815(5) -0.04510(12) 0.3672(3) 0.0240(8) Uani 1 1 d . . . C8 C 0.1175(5) 0.18542(11) 0.1027(3) 0.0159(7) Uani 1 1 d . . . C9 C 0.3075(5) 0.19583(12) 0.1815(3) 0.0186(7) Uani 1 1 d . . . C12 C -0.0113(5) 0.26240(12) 0.1365(3) 0.0174(7) Uani 1 1 d . . . C7 C 0.0755(5) 0.13702(12) 0.0461(3) 0.0178(7) Uani 1 1 d . . . C15 C 0.2460(6) 0.35515(13) 0.2073(3) 0.0252(8) Uani 1 1 d . . . C6 C 0.3437(5) 0.07311(12) 0.0987(3) 0.0187(7) Uani 1 1 d . . . C10 C 0.3375(5) 0.23937(12) 0.2367(3) 0.0162(7) Uani 1 1 d . . . C24 C 1.1960(7) -0.07761(14) 0.5882(3) 0.0344(10) Uani 1 1 d . . . C16 C -0.3541(5) 0.28883(15) 0.0431(3) 0.0257(8) Uani 1 1 d . . . C11 C 0.1793(5) 0.27302(11) 0.2154(3) 0.0169(7) Uani 1 1 d . . . C23 C 0.9813(6) -0.08397(13) 0.5501(3) 0.0312(9) Uani 1 1 d . . . C26 C 1.1971(6) -0.03915(13) 0.4039(3) 0.0292(9) Uani 1 1 d . . . C25 C 1.3034(7) -0.05469(14) 0.5151(4) 0.0348(10) Uani 1 1 d . . . C27 C 0.8638(6) -0.02624(13) 0.2496(3) 0.0263(8) Uani 1 1 d . . . C14 C 0.6706(6) 0.21688(15) 0.3561(4) 0.0356(10) Uani 1 1 d . . . H71 H 0.007(5) 0.1173(12) 0.097(3) 0.010(8) Uiso 1 1 d . . . H6 H 0.279(5) 0.0604(13) 0.159(3) 0.016(8) Uiso 1 1 d . . . H9 H 0.417(6) 0.1725(13) 0.193(3) 0.021(9) Uiso 1 1 d . . . H41 H 0.201(6) 0.1747(16) -0.128(3) 0.032(11) Uiso 1 1 d . . . H161 H -0.414(5) 0.2615(14) 0.068(3) 0.022(9) Uiso 1 1 d . . . H13 H -0.172(6) 0.2123(14) 0.028(3) 0.033(10) Uiso 1 1 d . . . H72 H -0.032(6) 0.1385(15) -0.028(4) 0.038(11) Uiso 1 1 d . . . H22' H 0.719(6) -0.0723(13) 0.416(3) 0.024(10) Uiso 1 1 d . . . H141 H 0.743(6) 0.2056(15) 0.290(3) 0.029(10) Uiso 1 1 d . . . H21 H 0.844(5) 0.0455(12) -0.071(3) 0.009(8) Uiso 1 1 d . . . H162 H -0.445(5) 0.3167(13) 0.041(3) 0.016(8) Uiso 1 1 d . . . H24 H 1.264(6) -0.0906(16) 0.672(4) 0.043(12) Uiso 1 1 d . . . H151 H 0.243(6) 0.3823(16) 0.255(4) 0.033(11) Uiso 1 1 d . . . H42 H 0.400(7) 0.1690(16) -0.178(4) 0.038(11) Uiso 1 1 d . . . H142 H 0.613(5) 0.1919(14) 0.387(3) 0.018(9) Uiso 1 1 d . . . H152 H 0.384(7) 0.3519(15) 0.188(3) 0.035(11) Uiso 1 1 d . . . H22 H 0.841(6) 0.0209(15) 0.040(3) 0.024(10) Uiso 1 1 d . . . H163 H -0.339(6) 0.2826(15) -0.039(4) 0.038(11) Uiso 1 1 d . . . H26 H 1.281(7) -0.0220(17) 0.349(4) 0.052(13) Uiso 1 1 d . . . H153 H 0.144(6) 0.3572(15) 0.131(4) 0.037(11) Uiso 1 1 d . . . H1 H 0.573(7) 0.0207(17) 0.135(4) 0.050(13) Uiso 1 1 d . . . H143 H 0.761(7) 0.2325(18) 0.429(4) 0.059(14) Uiso 1 1 d . . . H25 H 1.449(7) -0.0525(16) 0.544(4) 0.042(12) Uiso 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 Cl1 0.0692(8) 0.0408(6) 0.0311(6) 0.0098(4) 0.0210(5) 0.0115(5) O1 0.0163(11) 0.0220(13) 0.0285(13) -0.0043(11) -0.0068(9) -0.0010(10) O2 0.0249(12) 0.0156(12) 0.0184(11) -0.0022(9) 0.0028(9) -0.0012(10) O3 0.0145(11) 0.0228(13) 0.0316(13) -0.0048(11) -0.0023(10) 0.0067(10) O4 0.0295(14) 0.0218(13) 0.0271(13) 0.0054(10) -0.0021(10) 0.0030(11) N1 0.0167(13) 0.0151(14) 0.0214(14) 0.0024(12) 0.0018(11) 0.0011(12) N3 0.0183(14) 0.0129(14) 0.0253(15) -0.0005(11) 0.0056(11) 0.0001(11) O5 0.0513(17) 0.061(2) 0.0265(14) 0.0129(14) 0.0150(13) 0.0353(16) N2 0.0197(15) 0.0161(15) 0.0265(16) 0.0024(13) 0.0051(13) 0.0039(12) N4 0.0248(17) 0.0222(16) 0.0300(17) 0.0103(13) 0.0101(13) 0.0079(14) C13 0.0154(16) 0.0214(18) 0.0164(16) 0.0018(13) 0.0000(13) -0.0011(13) C4 0.0184(16) 0.0132(16) 0.0210(16) -0.0021(13) -0.0004(13) -0.0044(13) C5 0.0143(15) 0.0152(17) 0.0202(16) -0.0041(13) 0.0000(13) -0.0026(13) C2 0.0137(16) 0.0171(17) 0.0221(17) -0.0029(14) -0.0002(13) -0.0047(13) C22 0.035(2) 0.0241(19) 0.0222(18) -0.0001(15) 0.0050(15) 0.0072(16) C21 0.0313(19) 0.0190(17) 0.0195(17) -0.0043(14) 0.0013(14) 0.0106(15) C8 0.0144(15) 0.0162(16) 0.0166(15) 0.0010(13) 0.0029(12) -0.0051(13) C9 0.0130(16) 0.0174(17) 0.0238(17) 0.0026(14) 0.0007(13) 0.0012(14) C12 0.0162(16) 0.0176(17) 0.0183(16) 0.0021(13) 0.0037(13) 0.0019(13) C7 0.0164(16) 0.0161(17) 0.0190(16) 0.0000(14) 0.0004(14) -0.0026(14) C15 0.035(2) 0.0163(18) 0.0260(19) -0.0023(15) 0.0092(17) -0.0042(16) C6 0.0191(17) 0.0181(17) 0.0181(16) -0.0035(13) 0.0027(13) -0.0042(14) C10 0.0125(15) 0.0183(17) 0.0158(15) -0.0009(13) -0.0009(12) -0.0027(13) C24 0.051(3) 0.024(2) 0.0219(19) -0.0014(16) -0.0040(18) 0.0154(18) C16 0.0140(17) 0.030(2) 0.029(2) 0.0009(17) -0.0040(14) 0.0054(16) C11 0.0209(17) 0.0165(16) 0.0141(15) -0.0023(12) 0.0054(13) -0.0021(13) C23 0.050(2) 0.0217(19) 0.0230(18) -0.0015(16) 0.0105(17) 0.0103(18) C26 0.036(2) 0.0197(19) 0.0295(19) -0.0034(15) 0.0029(17) 0.0065(16) C25 0.034(2) 0.030(2) 0.034(2) -0.0043(18) -0.0064(18) 0.0110(18) C27 0.035(2) 0.0204(18) 0.0221(18) -0.0001(15) 0.0038(16) 0.0091(16) C14 0.025(2) 0.026(2) 0.044(2) -0.0042(19) -0.0158(19) 0.0050(17) _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 Cl1 C23 1.745(4) . ? O1 C10 1.373(4) . ? O1 C14 1.428(4) . ? O2 C11 1.383(4) . ? O2 C15 1.441(4) . ? O3 C12 1.369(4) . ? O3 C16 1.427(4) . ? O4 C27 1.257(5) . ? N1 C6 1.355(5) . ? N1 C2 1.365(4) . ? N3 C4 1.332(5) . ? N3 C2 1.337(4) . ? O5 C27 1.254(5) . ? N2 C2 1.320(5) . ? N4 C4 1.342(4) . ? C13 C12 1.381(5) . ? C13 C8 1.385(5) . ? C4 C5 1.431(5) . ? C5 C6 1.357(5) . ? C5 C7 1.492(5) . ? C22 C23 1.387(5) . ? C22 C21 1.393(5) . ? C21 C26 1.387(6) . ? C21 C27 1.504(5) . ? C8 C9 1.395(5) . ? C8 C7 1.516(4) . ? C9 C10 1.382(5) . ? C12 C11 1.400(5) . ? C10 C11 1.386(5) . ? C24 C25 1.383(6) . ? C24 C23 1.384(6) . ? C26 C25 1.391(5) . ? 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 C10 O1 C14 116.7(3) . . ? C11 O2 C15 114.0(2) . . ? C12 O3 C16 116.4(3) . . ? C6 N1 C2 119.3(3) . . ? C4 N3 C2 117.9(3) . . ? C12 C13 C8 120.3(3) . . ? N3 C4 N4 116.5(3) . . ? N3 C4 C5 123.3(3) . . ? N4 C4 C5 120.2(3) . . ? C6 C5 C4 115.2(3) . . ? C6 C5 C7 122.2(3) . . ? C4 C5 C7 122.6(3) . . ? N2 C2 N3 120.0(3) . . ? N2 C2 N1 117.7(3) . . ? N3 C2 N1 122.2(3) . . ? C23 C22 C21 118.9(4) . . ? C26 C21 C22 120.0(3) . . ? C26 C21 C27 120.5(3) . . ? C22 C21 C27 119.5(3) . . ? C13 C8 C9 119.5(3) . . ? C13 C8 C7 119.1(3) . . ? C9 C8 C7 121.3(3) . . ? C10 C9 C8 120.2(3) . . ? O3 C12 C13 125.4(3) . . ? O3 C12 C11 114.2(3) . . ? C13 C12 C11 120.4(3) . . ? C5 C7 C8 115.3(3) . . ? N1 C6 C5 122.1(3) . . ? O1 C10 C9 124.3(3) . . ? O1 C10 C11 115.1(3) . . ? C9 C10 C11 120.6(3) . . ? C25 C24 C23 119.1(3) . . ? O2 C11 C10 120.8(3) . . ? O2 C11 C12 120.1(3) . . ? C10 C11 C12 119.1(3) . . ? C24 C23 C22 121.5(4) . . ? C24 C23 Cl1 119.4(3) . . ? C22 C23 Cl1 119.1(3) . . ? C21 C26 C25 120.2(4) . . ? C24 C25 C26 120.3(4) . . ? O5 C27 O4 125.6(3) . . ? O5 C27 C21 116.9(3) . . ? O4 C27 C21 117.5(3) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.266 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.058 #------------------------------------------------------------------------------ data_tmpmw _database_code_CSD 194299 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H19 N4 O3, C7 H4 Cl O2, 1.2(H2 O)' _chemical_formula_sum 'C21 H25.4 Cl N4 O6.2' _chemical_formula_weight 468.90 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' Cl Cl 0.1484 0.1585 '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 7.2710(10) _cell_length_b 9.144(2) _cell_length_c 16.674(3) _cell_angle_alpha 86.93(3) _cell_angle_beta 80.92(3) _cell_angle_gamma 85.43(3) _cell_volume 1090.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3448 _cell_measurement_theta_min 3.41 _cell_measurement_theta_max 25.0 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.222 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD \k-geometry diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number '3 reference frames' _diffrn_standards_interval_count 'every 50 dc frames' _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8430 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0741 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3850 _reflns_number_gt 2815 _reflns_threshold_expression >2sigma(I) _computing_data_collection ;Kuma KM4CCD software (Kuma Diffraction, 1999) ; _computing_cell_refinement 'Kuma KM4CCD software' _computing_data_reduction 'Kuma KM4CCD software' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0426P)^2^+0.0000P] 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 3850 _refine_ls_number_parameters 385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0887 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 Cl1 Cl 1.36360(10) 0.17549(8) -0.84724(4) 0.0257(2) Uani 1 1 d . . . C2 C 1.1247(4) 0.8036(3) -0.44138(15) 0.0146(6) Uani 1 1 d . . . N1 N 1.1758(3) 0.6681(2) -0.41195(13) 0.0168(5) Uani 1 1 d . . . N3 N 1.0876(3) 0.9197(2) -0.39380(13) 0.0145(5) Uani 1 1 d . . . N2 N 1.1166(4) 0.8185(3) -0.52037(15) 0.0198(6) Uani 1 1 d . . . C4 C 1.1026(3) 0.8967(3) -0.31436(16) 0.0135(6) Uani 1 1 d . . . N4 N 1.0740(3) 1.0153(3) -0.26897(16) 0.0179(6) Uani 1 1 d . . . C5 C 1.1462(3) 0.7541(3) -0.27870(15) 0.0130(6) Uani 1 1 d . . . C6 C 1.1829(4) 0.6451(3) -0.33103(16) 0.0149(6) Uani 1 1 d . . . C7 C 1.1526(4) 0.7304(3) -0.18844(16) 0.0147(6) Uani 1 1 d . . . C8 C 1.1588(4) 0.5695(3) -0.16074(15) 0.0130(6) Uani 1 1 d . . . C9 C 0.9994(4) 0.5102(3) -0.11926(15) 0.0153(6) Uani 1 1 d . . . C10 C 1.0017(4) 0.3606(3) -0.09717(15) 0.0152(6) Uani 1 1 d . . . C11 C 1.1628(4) 0.2700(3) -0.11839(15) 0.0130(6) Uani 1 1 d . . . C12 C 1.3249(4) 0.3308(3) -0.15781(15) 0.0147(6) Uani 1 1 d . . . C13 C 1.3233(4) 0.4806(3) -0.17859(16) 0.0149(6) Uani 1 1 d . . . C14 C 0.6897(4) 0.3848(4) -0.02510(19) 0.0215(7) Uani 1 1 d . . . C15 C 1.2278(5) 0.0687(4) -0.02999(19) 0.0237(7) Uani 1 1 d . . . C16 C 1.6396(4) 0.2849(4) -0.2247(2) 0.0245(7) Uani 1 1 d . . . C21 C 1.3168(4) 0.2973(3) -0.61741(16) 0.0165(6) Uani 1 1 d . . . C22 C 1.3065(4) 0.2986(3) -0.69989(17) 0.0174(6) Uani 1 1 d . . . C23 C 1.3716(4) 0.1742(3) -0.74286(16) 0.0175(6) Uani 1 1 d . . . C24 C 1.4471(4) 0.0499(3) -0.70618(18) 0.0201(7) Uani 1 1 d . . . C25 C 1.4525(4) 0.0484(3) -0.62327(18) 0.0218(7) Uani 1 1 d . . . C26 C 1.3883(4) 0.1714(3) -0.5791(18) 0.0198(7) Uani 1 1 d . . . C27 C 1.2556(4) 0.4340(3) -0.56997(18) 0.0211(7) Uani 1 1 d . . . O1 O 0.8515(2) 0.29265(19) -0.05544(11) 0.0198(5) Uani 1 1 d . . . O2 O 1.1590(3) 0.11927(18) -0.10385(10) 0.0170(4) Uani 1 1 d . . . O3 O 1.4782(2) 0.23362(19) -0.17275(11) 0.0190(4) Uani 1 1 d . . . O5 O 1.2608(3) 0.4248(2) -0.49477(12) 0.0291(5) Uani 1 1 d . . . O4 O 1.2063(3) 0.5480(2) -0.60872(12) 0.0285(5) Uani 1 1 d . . . H1 H 1.208(5) 0.586(4) -0.446(2) 0.061(12) Uiso 1 1 d . . . H21 H 1.066(4) 0.898(4) -0.5421(19) 0.039(10) Uiso 1 1 d . . . H22 H 1.138(4) 0.744(4) -0.5484(18) 0.033(10) Uiso 1 1 d . . . H6 H 1.216(4) 0.549(3) -0.3147(16) 0.024(8) Uiso 1 1 d . . . H41 H 1.095(4) 1.008(3) -0.2184(17) 0.015(7) Uiso 1 1 d . . . H42 H 1.073(4) 1.093(3) -0.2934(18) 0.024(9) Uiso 1 1 d . . . H71 H 1.261(4) 0.776(3) -0.1747(15) 0.020(8) Uiso 1 1 d . . . H72 H 1.046(4) 0.778(3) -0.1583(14) 0.007(6) Uiso 1 1 d . . . H9 H 0.890(4) 0.568(3) -0.1060(15) 0.016(7) Uiso 1 1 d . . . H13 H 1.429(4) 0.525(3) -0.2056(14) 0.008(6) Uiso 1 1 d . . . H141 H 0.724(4) 0.463(3) 0.0090(16) 0.017(7) Uiso 1 1 d . . . H142 H 0.628(4) 0.431(3) -0.0714(16) 0.014(7) Uiso 1 1 d . . . H143 H 0.600(4) 0.318(3) 0.0045(18) 0.034(9) Uiso 1 1 d . . . H151 H 1.367(5) 0.094(3) -0.0335(18) 0.036(9) Uiso 1 1 d . . . H152 H 1.155(4) 0.115(3) 0.0159(18) 0.026(8) Uiso 1 1 d . . . H153 H 1.213(4) -0.038(3) -0.0264(16) 0.027(8) Uiso 1 1 d . . . H161 H 1.692(4) 0.363(4) -0.1994(19) 0.040(10) Uiso 1 1 d . . . H162 H 1.603(4) 0.323(3) -0.2789(18) 0.031(8) Uiso 1 1 d . . . H163 H 1.736(4) 0.196(3) -0.2308(18) 0.039(9) Uiso 1 1 d . . . H23 H 1.260(4) 0.381(3) -0.7259(17) 0.026(8) Uiso 1 1 d . . . H24 H 1.491(4) -0.033(3) -0.7384(18) 0.031(8) Uiso 1 1 d . . . H25 H 1.501(4) -0.045(3) -0.5974(17) 0.028(8) Uiso 1 1 d . . . H26 H 1.395(4) 0.172(3) -0.5235(18) 0.028(8) Uiso 1 1 d . . . O6 O 1.0994(3) 0.3029(2) -0.33902(13) 0.0401(6) Uani 1 1 d . . . H1W H 0.9996 0.3548 -0.3446 0.048 Uiso 1 1 d R . . H2W H 1.1786 0.3200 -0.3811 0.048 Uiso 1 1 d R . . O7 O 1.4307(16) 0.3129(12) -0.3917(7) 0.044(3) Uiso 0.20 1 d P . . 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 Cl1 0.0245(4) 0.0319(4) 0.0213(4) -0.0066(3) -0.0059(3) 0.0021(3) C2 0.0156(14) 0.0154(14) 0.0130(14) 0.0002(11) -0.0026(11) -0.0024(12) N1 0.0263(14) 0.0098(12) 0.0143(12) -0.0010(10) -0.0043(10) 0.0012(10) N3 0.0179(13) 0.0109(12) 0.0151(12) -0.0014(9) -0.0040(10) -0.0001(10) N2 0.0339(16) 0.0098(13) 0.0156(13) -0.0026(11) -0.0057(11) 0.0041(11) C4 0.0087(13) 0.0138(14) 0.0180(15) -0.0024(12) -0.0010(11) -0.0018(11) N4 0.0275(15) 0.0116(13) 0.0149(14) -0.0005(11) -0.0064(11) 0.0017(11) C5 0.0108(14) 0.0118(14) 0.0159(14) -0.0002(11) -0.0004(11) -0.0010(11) C6 0.0157(15) 0.0125(14) 0.0165(15) 0.0015(12) -0.0033(12) -0.0012(12) C7 0.0170(15) 0.0122(14) 0.0148(15) -0.0013(11) -0.0020(12) -0.0003(12) C8 0.0172(14) 0.0129(14) 0.0098(13) -0.0011(11) -0.0051(11) -0.0004(11) C9 0.0157(15) 0.0150(15) 0.0144(14) -0.0022(11) -0.0021(12) 0.0048(12) C10 0.0161(14) 0.0171(14) 0.0132(14) 0.0017(11) -0.0036(11) -0.0043(12) C11 0.0198(15) 0.0098(13) 0.0101(13) 0.0003(11) -0.0046(11) -0.0017(11) C12 0.0170(15) 0.0156(14) 0.0110(14) -0.0032(11) -0.0017(11) 0.0033(12) C13 0.0162(15) 0.0165(15) 0.0123(14) 0.0004(12) -0.0004(12) -0.0064(12) C14 0.0133(15) 0.0273(18) 0.0225(17) 0.0003(15) 0.0003(13) -0.0006(14) C15 0.0319(19) 0.0203(17) 0.0192(16) 0.0039(14) -0.0080(14) 0.0013(15) C16 0.0166(16) 0.0206(17) 0.0336(19) -0.0052(15) 0.0051(14) 0.0007(14) C21 0.0165(15) 0.0123(14) 0.0198(15) -0.0052(12) 0.0032(12) -0.0038(12) C22 0.0115(14) 0.0152(15) 0.0242(16) 0.0015(13) 0.0004(12) -0.0010(12) C23 0.0133(14) 0.0234(16) 0.0160(15) -0.0038(12) -0.0004(11) -0.0045(12) C24 0.0181(15) 0.0149(15) 0.0275(17) -0.0067(13) -0.0015(13) -0.0025(13) C25 0.0232(16) 0.0156(15) 0.0261(17) -0.0017(13) -0.0028(13) -0.0005(13) C26 0.0230(16) 0.0171(15) 0.0191(16) -0.0024(13) -0.0015(13) -0.0016(13) C27 0.0198(16) 0.0163(15) 0.0248(17) -0.0021(13) 0.0053(13) -0.0028(13) O1 0.0149(10) 0.0171(10) 0.0251(11) 0.0036(9) 0.0021(8) -0.0001(8) O2 0.0231(11) 0.0120(10) 0.0168(10) 0.0011(8) -0.0060(8) -0.0012(8) O3 0.0158(10) 0.0141(10) 0.0247(11) -0.0019(8) 0.0024(8) 0.0029(8) O5 0.0463(14) 0.0180(11) 0.0209(12) -0.0068(9) 0.0028(10) -0.0018(10) O4 0.0374(13) 0.0132(10) 0.0321(12) -0.0024(9) 0.0021(10) 0.0013(9) O6 0.0605(16) 0.0158(11) 0.0487(15) 0.0011(10) -0.0228(12) -0.0040(11) _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 Cl1 C23 1.750(3) . ? C2 N2 1.327(3) . ? C2 N3 1.344(3) . ? C2 N1 1.354(3) . ? N1 C6 1.363(3) . ? N1 H1 0.96(4) . ? N3 C4 1.350(3) . ? N2 H21 0.87(3) . ? N2 H22 0.84(3) . ? C4 N4 1.340(3) . ? C4 C5 1.437(3) . ? N4 H41 0.88(3) . ? N4 H42 0.80(3) . ? C5 C6 1.343(4) . ? C5 C7 1.516(4) . ? C6 H6 0.93(3) . ? C7 C8 1.517(3) . ? C7 H71 0.98(3) . ? C7 H72 0.94(2) . ? C8 C9 1.387(4) . ? C8 C13 1.393(4) . ? C9 C10 1.396(4) . ? C9 H9 0.93(3) . ? C10 O1 1.373(3) . ? C10 C11 1.389(4) . ? C11 O2 1.389(3) . ? C11 C12 1.396(4) . ? C12 O3 1.368(3) . ? C12 C13 1.395(4) . ? C13 H13 0.94(3) . ? C14 O1 1.432(3) . ? C14 H141 1.00(3) . ? C14 H142 1.01(3) . ? C14 H143 0.98(3) . ? C15 O2 1.441(3) . ? C15 H151 1.04(3) . ? C15 H152 0.96(3) . ? C15 H153 0.99(3) . ? C16 O3 1.439(3) . ? C16 H161 0.98(3) . ? C16 H162 1.02(3) . ? C16 H163 1.02(3) . ? C21 C22 1.388(4) . ? C21 C26 1.390(4) . ? C21 C27 1.514(4) . ? C22 C23 1.388(4) . ? C22 H22 0.92(3) . ? C23 C24 1.378(4) . ? C24 C25 1.388(4) . ? C24 H24 0.96(3) . ? C25 C26 1.386(4) . ? C25 H25 1.00(3) . ? C26 H26 0.94(3) . ? C27 O4 1.255(3) . ? C27 O5 1.258(3) . ? O6 H1W 0.8499 . ? O6 H2W 0.8500 . ? 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 N2 C2 N3 120.8(2) . . ? N2 C2 N1 117.1(2) . . ? N3 C2 N1 122.1(2) . . ? C2 N1 C6 119.9(2) . . ? C2 N1 H1 122(2) . . ? C6 N1 H1 118(2) . . ? C2 N3 C4 117.4(2) . . ? C2 N2 H21 122(2) . . ? C2 N2 H22 119(2) . . ? H21 N2 H22 118(3) . . ? N4 C4 N3 116.4(2) . . ? N4 C4 C5 120.6(2) . . ? N3 C4 C5 123.0(2) . . ? C4 N4 H41 120.0(17) . . ? C4 N4 H42 116(2) . . ? H41 N4 H42 120(3) . . ? C6 C5 C4 115.2(2) . . ? C6 C5 C7 122.9(2) . . ? C4 C5 C7 121.9(2) . . ? C5 C6 N1 122.2(2) . . ? C5 C6 H4 122.3(17) . . ? N1 C6 H4 115.5(17) . . ? C5 C7 C8 113.0(2) . . ? C5 C7 H71 109.5(15) . . ? C8 C7 H71 110.1(15) . . ? C5 C7 H72 110.2(15) . . ? C8 C7 H72 107.4(15) . . ? H71 C7 H72 106(2) . . ? C9 C8 C13 120.0(2) . . ? C9 C8 C7 120.0(2) . . ? C13 C8 C7 120.0(2) . . ? C8 C9 C10 120.3(2) . . ? C8 C9 H9 120.9(16) . . ? C10 C9 H9 118.9(16) . . ? O1 C10 C11 115.7(2) . . ? O1 C10 C9 124.3(2) . . ? C11 C10 C9 120.0(2) . . ? O2 C11 C10 119.8(2) . . ? O2 C11 C12 120.5(2) . . ? C10 C11 C12 119.6(2) . . ? O3 C12 C13 124.6(2) . . ? O3 C12 C11 115.2(2) . . ? C13 C12 C11 120.3(2) . . ? C8 C13 C12 119.8(3) . . ? C8 C13 H13 117.8(15) . . ? C12 C13 H13 122.5(15) . . ? O1 C14 H141 110.6(15) . . ? O1 C14 H142 110.7(14) . . ? H141 C14 H142 110(2) . . ? O1 C14 H143 105.6(16) . . ? H141 C14 H143 114(2) . . ? H142 C14 H143 106(2) . . ? O2 C15 H151 109.6(16) . . ? O2 C15 H152 110.6(17) . . ? H151 C15 H152 109(2) . . ? O2 C15 H153 104.3(17) . . ? H151 C15 H153 113(2) . . ? H152 C15 H153 110(2) . . ? O3 C16 H161 110.8(18) . . ? O3 C16 H162 109.3(17) . . ? H161 C16 H162 110(2) . . ? O3 C16 H163 105.7(17) . . ? H161 C16 H163 109(2) . . ? H162 C16 H163 112(2) . . ? C22 C21 C26 119.8(3) . . ? C22 C21 C27 120.0(2) . . ? C26 C21 C27 120.2(2) . . ? C23 C22 C21 118.9(3) . . ? C23 C22 H22 120.4(17) . . ? C21 C22 H22 120.6(17) . . ? C24 C23 C22 121.9(3) . . ? C24 C23 Cl1 118.6(2) . . ? C22 C23 Cl1 119.4(2) . . ? C23 C24 C25 118.6(3) . . ? C23 C24 H24 118.9(17) . . ? C25 C24 H24 122.4(17) . . ? C26 C25 C24 120.4(3) . . ? C26 C25 H25 122.3(16) . . ? C24 C25 H25 117.3(16) . . ? C25 C26 C21 120.2(3) . . ? C25 C26 H26 121.0(17) . . ? C21 C26 H26 118.8(17) . . ? O4 C27 O5 125.0(3) . . ? O4 C27 C21 117.6(3) . . ? O5 C27 C21 117.3(2) . . ? C10 O1 C14 117.1(2) . . ? C11 O2 C15 113.1(2) . . ? C12 O3 C16 117.3(2) . . ? H1W O6 H2W 107.1 . . ? 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 N2 C2 N1 C6 -178.6(3) . . . . ? N3 C2 N1 C6 2.9(4) . . . . ? N2 C2 N3 C4 -178.6(2) . . . . ? N1 C2 N3 C4 -0.2(4) . . . . ? C2 N3 C4 N4 176.8(2) . . . . ? C2 N3 C4 C5 -3.3(4) . . . . ? N4 C4 C5 C6 -176.2(3) . . . . ? N3 C4 C5 C6 3.9(4) . . . . ? N4 C4 C5 C7 3.0(4) . . . . ? N3 C4 C5 C7 -176.9(2) . . . . ? C4 C5 C6 N1 -1.1(4) . . . . ? C7 C5 C6 N1 179.7(2) . . . . ? C2 N1 C6 C5 -2.2(4) . . . . ? C6 C5 C7 C8 -13.5(4) . . . . ? C4 C5 C7 C8 167.4(2) . . . . ? C5 C7 C8 C9 -103.4(3) . . . . ? C5 C7 C8 C13 75.1(3) . . . . ? C13 C8 C9 C10 -1.7(4) . . . . ? C7 C8 C9 C10 176.8(2) . . . . ? C8 C9 C10 O1 179.3(2) . . . . ? C8 C9 C10 C11 -1.5(4) . . . . ? O1 C10 C11 O2 5.9(4) . . . . ? C9 C10 C11 O2 -173.3(2) . . . . ? O1 C10 C11 C12 -177.2(2) . . . . ? C9 C10 C11 C12 3.6(4) . . . . ? O2 C11 C12 O3 -6.0(4) . . . . ? C10 C11 C12 O3 177.1(2) . . . . ? O2 C11 C12 C13 174.4(2) . . . . ? C10 C11 C12 C13 -2.4(4) . . . . ? C9 C8 C13 C12 2.8(4) . . . . ? C7 C8 C13 C12 -175.7(2) . . . . ? O3 C12 C13 C8 179.7(2) . . . . ? C11 C12 C13 C8 -0.7(4) . . . . ? C26 C21 C22 C23 -1.2(4) . . . . ? C27 C21 C22 C23 177.0(2) . . . . ? C21 C22 C23 C24 -0.4(4) . . . . ? C21 C22 C23 Cl1 -178.8(2) . . . . ? C22 C23 C24 C25 2.0(4) . . . . ? Cl1 C23 C24 C25 -179.6(2) . . . . ? C23 C24 C25 C26 -2.0(4) . . . . ? C24 C25 C26 C21 0.4(5) . . . . ? C22 C21 C26 C25 1.2(4) . . . . ? C27 C21 C26 C25 -177.0(3) . . . . ? C22 C21 C27 O4 -3.8(4) . . . . ? C26 C21 C27 O4 174.4(3) . . . . ? C22 C21 C27 O5 177.2(3) . . . . ? C26 C21 C27 O5 -4.6(4) . . . . ? C11 C10 O1 C14 173.5(2) . . . . ? C9 C10 O1 C14 -7.3(4) . . . . ? C10 C11 O2 C15 -97.9(3) . . . . ? C12 C11 O2 C15 85.2(3) . . . . ? C13 C12 O3 C16 -10.5(4) . . . . ? C11 C12 O3 C16 170.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.438 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.055 #=============================================================================