# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Philip Gale' 'Mark E. Light' 'Beth A. McNally' 'Korakot Navakhun' 'Kate E. Sliwinski' 'Bradley Smith' _publ_contact_author_name 'Dr Philip Gale' _publ_contact_author_address ; Department of Chemistry University of Southampton Southampton SO17 1BJ UNITED KINGDOM ; _publ_contact_author_email PHILIP.GALE@SOTON.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Co-transport of H+/Cl- by a synthetic prodigiosin mimic ; data_03sot062 _database_code_depnum_ccdc_archive 'CCDC 266941' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H22 N4 O' _chemical_formula_weight 370.45 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' O O 0.0106 0.0060 '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' _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 7.3267(2) _cell_length_b 10.4025(3) _cell_length_c 13.6141(4) _cell_angle_alpha 82.523(2) _cell_angle_beta 76.069(2) _cell_angle_gamma 82.898(2) _cell_volume 993.93(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9769 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker Nonius Kappa CCD Area detector' _diffrn_measurement_method '\f and \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17926 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3507 _reflns_number_gt 3066 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and MInor, 1997)' _computing_data_reduction 'DENZO, COLLECT, MAXUS (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0567P)^2^+0.2227P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.030(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3507 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _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 0.7717(2) 0.02998(15) 0.20529(11) 0.0415(4) Uani 1 1 d . . . H1A H 0.8795 0.0743 0.2099 0.062 Uiso 1 1 calc R . . H1B H 0.7767 0.0220 0.1337 0.062 Uiso 1 1 calc R . . H1C H 0.7770 -0.0570 0.2428 0.062 Uiso 1 1 calc R . . C2 C 0.59224(19) 0.10709(13) 0.25020(10) 0.0336(3) Uani 1 1 d . . . C3 C 0.46667(19) 0.18821(13) 0.20404(10) 0.0339(3) Uani 1 1 d . . . C4 C 0.31960(19) 0.24018(12) 0.28276(10) 0.0319(3) Uani 1 1 d . . . C5 C 0.36367(18) 0.18746(12) 0.37426(10) 0.0304(3) Uani 1 1 d . . . C6 C 0.26786(17) 0.19634(12) 0.48132(10) 0.0293(3) Uani 1 1 d . . . C7 C 0.05857(18) 0.33147(13) 0.60569(10) 0.0321(3) Uani 1 1 d . . . H7A H 0.0792 0.4166 0.6242 0.039 Uiso 1 1 calc R . . H7B H 0.0969 0.2627 0.6563 0.039 Uiso 1 1 calc R . . C8 C -0.14661(18) 0.32883(12) 0.60960(10) 0.0304(3) Uani 1 1 d . . . C9 C -0.43082(19) 0.38786(14) 0.59473(10) 0.0374(3) Uani 1 1 d . . . H9 H -0.5413 0.4410 0.5847 0.045 Uiso 1 1 calc R . . C10 C -0.41739(19) 0.25670(14) 0.61334(10) 0.0354(3) Uani 1 1 d . . . H10 H -0.5142 0.2016 0.6185 0.043 Uiso 1 1 calc R . . C11 C -0.1641(2) 0.08486(14) 0.64775(15) 0.0508(4) Uani 1 1 d . . . H11A H -0.0301 0.0816 0.6484 0.076 Uiso 1 1 calc R . . H11B H -0.1783 0.0313 0.5964 0.076 Uiso 1 1 calc R . . H11C H -0.2351 0.0514 0.7149 0.076 Uiso 1 1 calc R . . C12 C 0.4758(2) 0.20734(14) 0.09324(11) 0.0409(4) Uani 1 1 d . . . C13 C 0.6393(3) 0.24397(16) 0.02384(12) 0.0551(4) Uani 1 1 d . . . H13 H 0.7459 0.2585 0.0477 0.066 Uiso 1 1 calc R . . C14 C 0.6469(4) 0.2592(2) -0.07930(15) 0.0776(7) Uani 1 1 d . . . H14 H 0.7598 0.2821 -0.1261 0.093 Uiso 1 1 calc R . . C15 C 0.4921(5) 0.2413(2) -0.11475(16) 0.0881(8) Uani 1 1 d . . . H15 H 0.4977 0.2528 -0.1858 0.106 Uiso 1 1 calc R . . C16 C 0.3291(4) 0.2069(2) -0.04700(16) 0.0781(7) Uani 1 1 d . . . H16 H 0.2213 0.1961 -0.0713 0.094 Uiso 1 1 calc R . . C17 C 0.3215(3) 0.18785(17) 0.05635(13) 0.0547(4) Uani 1 1 d . . . H17 H 0.2099 0.1612 0.1024 0.066 Uiso 1 1 calc R . . C18 C 0.14662(19) 0.32141(13) 0.26592(10) 0.0340(3) Uani 1 1 d . . . C19 C 0.1580(2) 0.42529(14) 0.18939(11) 0.0422(4) Uani 1 1 d . . . H19 H 0.2782 0.4507 0.1533 0.051 Uiso 1 1 calc R . . C20 C -0.0040(2) 0.49171(16) 0.16541(12) 0.0495(4) Uani 1 1 d . . . H20 H 0.0063 0.5608 0.1119 0.059 Uiso 1 1 calc R . . C21 C -0.1805(2) 0.45854(15) 0.21849(13) 0.0490(4) Uani 1 1 d . . . H21 H -0.2912 0.5039 0.2013 0.059 Uiso 1 1 calc R . . C22 C -0.1944(2) 0.35899(15) 0.29658(13) 0.0443(4) Uani 1 1 d . . . H22 H -0.3153 0.3372 0.3346 0.053 Uiso 1 1 calc R . . C23 C -0.0328(2) 0.29034(14) 0.31998(11) 0.0382(3) Uani 1 1 d . . . H23 H -0.0444 0.2213 0.3735 0.046 Uiso 1 1 calc R . . O1 O 0.27526(13) 0.09977(9) 0.54549(7) 0.0338(2) Uani 1 1 d . . . N1 N 0.52741(15) 0.10624(10) 0.35250(8) 0.0316(3) Uani 1 1 d . . . H1 H 0.5824 0.0603 0.3982 0.038 Uiso 1 1 calc R . . N2 N 0.17577(15) 0.31116(10) 0.50521(8) 0.0309(3) Uani 1 1 d . . . H2 H 0.1865 0.3778 0.4579 0.037 Uiso 1 1 calc R . . N3 N -0.26083(16) 0.43321(11) 0.59234(9) 0.0360(3) Uani 1 1 d . . . N4 N -0.23636(15) 0.21892(10) 0.62326(8) 0.0329(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 C1 0.0412(8) 0.0393(8) 0.0408(8) -0.0055(6) -0.0048(6) 0.0010(6) C2 0.0361(7) 0.0294(7) 0.0349(7) -0.0042(5) -0.0059(5) -0.0053(5) C3 0.0386(7) 0.0281(7) 0.0349(7) -0.0027(5) -0.0077(6) -0.0055(6) C4 0.0370(7) 0.0247(6) 0.0348(7) -0.0020(5) -0.0090(5) -0.0055(5) C5 0.0316(7) 0.0234(6) 0.0362(7) -0.0026(5) -0.0076(5) -0.0030(5) C6 0.0290(6) 0.0253(6) 0.0354(7) -0.0020(5) -0.0106(5) -0.0044(5) C7 0.0354(7) 0.0273(7) 0.0349(7) -0.0065(5) -0.0081(5) -0.0044(5) C8 0.0351(7) 0.0260(7) 0.0299(7) -0.0047(5) -0.0055(5) -0.0037(5) C9 0.0330(7) 0.0394(8) 0.0378(8) 0.0015(6) -0.0080(6) -0.0015(6) C10 0.0327(7) 0.0384(8) 0.0363(7) -0.0038(6) -0.0081(5) -0.0074(6) C11 0.0423(8) 0.0256(7) 0.0827(12) 0.0000(7) -0.0128(8) -0.0048(6) C12 0.0562(9) 0.0295(7) 0.0350(8) -0.0043(6) -0.0091(6) 0.0018(6) C13 0.0738(12) 0.0425(9) 0.0413(9) -0.0013(7) -0.0001(8) -0.0050(8) C14 0.1190(19) 0.0570(12) 0.0401(10) 0.0020(9) 0.0049(11) 0.0032(12) C15 0.152(2) 0.0683(14) 0.0353(10) -0.0076(9) -0.0240(13) 0.0293(15) C16 0.1140(18) 0.0720(14) 0.0583(12) -0.0265(10) -0.0473(13) 0.0277(13) C17 0.0705(11) 0.0509(10) 0.0475(9) -0.0146(8) -0.0248(8) 0.0080(8) C18 0.0407(8) 0.0285(7) 0.0356(7) -0.0072(6) -0.0132(6) -0.0012(6) C19 0.0499(9) 0.0358(8) 0.0393(8) -0.0021(6) -0.0107(6) 0.0011(6) C20 0.0634(11) 0.0405(9) 0.0441(9) -0.0023(7) -0.0203(8) 0.0108(7) C21 0.0525(9) 0.0427(9) 0.0592(10) -0.0149(8) -0.0299(8) 0.0107(7) C22 0.0397(8) 0.0368(8) 0.0616(10) -0.0149(7) -0.0177(7) -0.0009(6) C23 0.0413(8) 0.0302(7) 0.0456(8) -0.0064(6) -0.0137(6) -0.0036(6) O1 0.0381(5) 0.0273(5) 0.0348(5) 0.0002(4) -0.0084(4) -0.0018(4) N1 0.0334(6) 0.0275(6) 0.0338(6) -0.0022(5) -0.0087(4) -0.0012(4) N2 0.0340(6) 0.0241(6) 0.0337(6) -0.0016(4) -0.0064(4) -0.0036(4) N3 0.0361(6) 0.0301(6) 0.0392(7) -0.0018(5) -0.0054(5) -0.0012(5) N4 0.0335(6) 0.0267(6) 0.0385(6) -0.0042(5) -0.0074(5) -0.0041(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 C1 C2 1.4922(19) . ? C2 N1 1.3581(17) . ? C2 C3 1.3791(19) . ? C3 C4 1.4327(19) . ? C3 C12 1.482(2) . ? C4 C5 1.3888(19) . ? C4 C18 1.4824(19) . ? C5 N1 1.3726(17) . ? C5 C6 1.4670(18) . ? C6 O1 1.2475(15) . ? C6 N2 1.3356(16) . ? C7 N2 1.4554(17) . ? C7 C8 1.4949(18) . ? C8 N3 1.3184(17) . ? C8 N4 1.3586(17) . ? C9 C10 1.351(2) . ? C9 N3 1.3772(18) . ? C10 N4 1.3695(17) . ? C11 N4 1.4553(18) . ? C12 C17 1.389(2) . ? C12 C13 1.395(2) . ? C13 C14 1.381(3) . ? C14 C15 1.375(4) . ? C15 C16 1.377(4) . ? C16 C17 1.384(3) . ? C18 C19 1.396(2) . ? C18 C23 1.397(2) . ? C19 C20 1.385(2) . ? C20 C21 1.381(2) . ? C21 C22 1.379(2) . ? C22 C23 1.388(2) . ? 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 N1 C2 C3 107.95(12) . . ? N1 C2 C1 121.45(12) . . ? C3 C2 C1 130.60(13) . . ? C2 C3 C4 107.65(12) . . ? C2 C3 C12 125.29(12) . . ? C4 C3 C12 126.84(13) . . ? C5 C4 C3 106.24(12) . . ? C5 C4 C18 128.55(12) . . ? C3 C4 C18 124.85(12) . . ? N1 C5 C4 107.95(11) . . ? N1 C5 C6 118.40(11) . . ? C4 C5 C6 133.53(12) . . ? O1 C6 N2 122.90(12) . . ? O1 C6 C5 120.24(11) . . ? N2 C6 C5 116.86(11) . . ? N2 C7 C8 111.91(10) . . ? N3 C8 N4 111.07(12) . . ? N3 C8 C7 123.90(12) . . ? N4 C8 C7 124.83(12) . . ? C10 C9 N3 110.03(12) . . ? C9 C10 N4 106.32(12) . . ? C17 C12 C13 118.60(15) . . ? C17 C12 C3 120.40(14) . . ? C13 C12 C3 121.00(15) . . ? C14 C13 C12 120.4(2) . . ? C15 C14 C13 120.5(2) . . ? C14 C15 C16 119.79(19) . . ? C15 C16 C17 120.3(2) . . ? C16 C17 C12 120.5(2) . . ? C19 C18 C23 117.90(13) . . ? C19 C18 C4 120.58(13) . . ? C23 C18 C4 121.31(12) . . ? C20 C19 C18 120.76(15) . . ? C21 C20 C19 120.64(15) . . ? C22 C21 C20 119.35(14) . . ? C21 C22 C23 120.42(15) . . ? C22 C23 C18 120.88(14) . . ? C2 N1 C5 110.19(11) . . ? C6 N2 C7 123.20(11) . . ? C8 N3 C9 105.55(11) . . ? C8 N4 C10 107.02(11) . . ? C8 N4 C11 128.63(12) . . ? C10 N4 C11 124.31(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.88 2.02 2.8351(14) 154.1 2_656 N2 H2 N3 0.88 2.09 2.8837(15) 149.7 2_566 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.201 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.044 #===END data_03sot0174 _database_code_depnum_ccdc_archive 'CCDC 266942' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H25 Cl N4 O2' _chemical_formula_weight 424.92 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' Cl Cl 0.1484 0.1585 '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 C2/c 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' '-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 35.854(5) _cell_length_b 6.249(5) _cell_length_c 22.020(5) _cell_angle_alpha 90.00 _cell_angle_beta 120.620(9) _cell_angle_gamma 90.00 _cell_volume 4246(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2491 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 23.08 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min 0.9795 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.6933 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 12382 _diffrn_reflns_av_R_equivalents 0.0689 _diffrn_reflns_av_sigmaI/netI 0.0676 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 23.26 _reflns_number_total 3025 _reflns_number_gt 2219 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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 water is disordered over 3 positions and it?s refinement was constrained. All hydrogens were confirmed from the difference map and then refined in geometrical positions. The scattering power of the crystal was low and as a result the bond length precision is low. ; _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^)+(0.0818P)^2^+12.6642P] 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 SHELXL _refine_ls_extinction_coef 0.008(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3025 _refine_ls_number_parameters 287 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0955 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1872 _refine_ls_wR_factor_gt 0.1693 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 6.029 _refine_ls_shift/su_max 0.782 _refine_ls_shift/su_mean 0.017 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 -0.0712(6) 0.360(3) 0.0227(10) 0.043(5) Uani 1 1 d . . . H1 H -0.0460 0.4221 0.0376 0.052 Uiso 1 1 calc R . . N2 N -0.0768(6) 0.732(3) -0.0535(10) 0.044(5) Uani 1 1 d . . . H2 H -0.0525 0.6949 -0.0153 0.053 Uiso 1 1 calc R . . N3 N -0.0690(6) 0.744(3) -0.1793(10) 0.044(5) Uani 1 1 d . . . H3 H -0.0526 0.6401 -0.1513 0.052 Uiso 1 1 calc R . . N4 N -0.1088(6) 1.026(3) -0.2168(10) 0.041(5) Uani 1 1 d . . . O1 O -0.1447(5) 0.646(3) -0.1369(8) 0.049(5) Uani 1 1 d . . . C1 C -0.0415(7) 0.107(4) 0.1237(12) 0.050(6) Uani 1 1 d . . . H1A H -0.0244 0.0054 0.1138 0.074 Uiso 1 1 calc R . . H1B H -0.0533 0.0341 0.1497 0.074 Uiso 1 1 calc R . . H1C H -0.0230 0.2256 0.1520 0.074 Uiso 1 1 calc R . . C2 C -0.0780(7) 0.192(4) 0.0556(12) 0.043(6) Uani 1 1 d . . . C3 C -0.1214(7) 0.137(4) 0.0160(12) 0.042(6) Uani 1 1 d . . . C4 C -0.1415(7) 0.280(4) -0.0427(12) 0.043(6) Uani 1 1 d . . . C5 C -0.1093(7) 0.417(4) -0.0372(12) 0.042(6) Uani 1 1 d . . . C6 C -0.1122(8) 0.603(4) -0.0805(12) 0.043(6) Uani 1 1 d . . . C7 C -0.0798(8) 0.935(4) -0.0890(12) 0.046(6) Uani 1 1 d . . . H7A H -0.0530 1.0185 -0.0600 0.055 Uiso 1 1 calc R . . H7B H -0.1045 1.0186 -0.0933 0.055 Uiso 1 1 calc R . . C8 C -0.0860(7) 0.901(4) -0.1606(11) 0.040(6) Uani 1 1 d . . . C9 C -0.0806(8) 0.767(4) -0.2486(12) 0.048(6) Uani 1 1 d . . . H9 H -0.0726 0.6768 -0.2747 0.058 Uiso 1 1 calc R . . C10 C -0.1058(8) 0.943(4) -0.2726(13) 0.048(6) Uani 1 1 d . . . H10 H -0.1189 0.9999 -0.3191 0.057 Uiso 1 1 calc R . . C11 C -0.1326(8) 1.221(4) -0.2187(13) 0.048(6) Uani 1 1 d . . . H11A H -0.1534 1.1851 -0.2039 0.072 Uiso 1 1 calc R . . H11B H -0.1481 1.2780 -0.2668 0.072 Uiso 1 1 calc R . . H11C H -0.1121 1.3278 -0.1865 0.072 Uiso 1 1 calc R . . C12 C -0.1427(7) -0.027(4) 0.0368(11) 0.043(6) Uani 1 1 d . . . C13 C -0.1234(8) -0.226(4) 0.0633(11) 0.045(6) Uani 1 1 d . . . H13 H -0.0965 -0.2590 0.0666 0.054 Uiso 1 1 calc R . . C14 C -0.1429(8) -0.377(4) 0.0849(12) 0.050(7) Uani 1 1 d . . . H14 H -0.1293 -0.5112 0.1029 0.060 Uiso 1 1 calc R . . C15 C -0.1821(8) -0.331(4) 0.0801(13) 0.052(7) Uani 1 1 d . . . H15 H -0.1955 -0.4328 0.0949 0.062 Uiso 1 1 calc R . . C16 C -0.2017(8) -0.134(5) 0.0536(13) 0.053(7) Uani 1 1 d . . . H16 H -0.2287 -0.1024 0.0500 0.063 Uiso 1 1 calc R . . C17 C -0.1825(7) 0.015(4) 0.0326(12) 0.044(6) Uani 1 1 d . . . H17 H -0.1963 0.1491 0.0149 0.053 Uiso 1 1 calc R . . C18 C -0.1883(7) 0.278(4) -0.0985(12) 0.043(6) Uani 1 1 d . . . C19 C -0.2073(7) 0.094(4) -0.1385(12) 0.047(6) Uani 1 1 d . . . H19 H -0.1899 -0.0295 -0.1307 0.057 Uiso 1 1 calc R . . C20 C -0.2511(8) 0.088(5) -0.1895(13) 0.052(7) Uani 1 1 d . . . H20 H -0.2635 -0.0383 -0.2164 0.062 Uiso 1 1 calc R . . C21 C -0.2766(8) 0.267(5) -0.2008(13) 0.054(7) Uani 1 1 d . . . H21 H -0.3066 0.2641 -0.2353 0.065 Uiso 1 1 calc R . . C22 C -0.2579(8) 0.451(5) -0.1612(12) 0.051(7) Uani 1 1 d . . . H22 H -0.2753 0.5748 -0.1692 0.061 Uiso 1 1 calc R . . C23 C -0.2146(8) 0.456(4) -0.1108(12) 0.047(6) Uani 1 1 d . . . H23 H -0.2024 0.5826 -0.0840 0.056 Uiso 1 1 calc R . . Cl1 Cl -0.01554(19) 0.6514(10) 0.4060(3) 0.051(2) Uani 1 1 d . . . O2 O -0.0108(18) 0.544(7) 0.213(3) 0.129(14) Uani 0.67 1 d PDU . 1 H96 H 0.010(6) 0.59(4) 0.209(17) 0.050 Uiso 0.67 1 d PD A 1 H97 H -0.014(9) 0.411(9) 0.208(19) 0.050 Uiso 0.67 1 d PD B 1 O3 O 0.0000 0.697(11) 0.2500 0.129(14) Uani 0.67 2 d SPDU C 2 H99 H 0.030(7) 0.73(9) 0.26(2) 0.050 Uiso 0.33 1 d PD D 2 H98 H -0.023(12) 0.73(11) 0.209(18) 0.050 Uiso 0.33 1 d PD E 2 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 0.035(10) 0.053(13) 0.040(11) 0.001(10) 0.019(9) 0.002(9) N2 0.040(11) 0.052(13) 0.036(10) 0.004(9) 0.016(9) 0.007(10) N3 0.045(11) 0.046(12) 0.039(11) 0.002(9) 0.021(9) 0.004(10) N4 0.039(11) 0.041(11) 0.039(11) -0.001(9) 0.017(9) -0.004(9) O1 0.042(10) 0.060(11) 0.040(9) 0.002(8) 0.016(8) 0.006(8) C1 0.038(13) 0.060(17) 0.046(14) 0.002(12) 0.018(11) 0.007(12) C2 0.040(14) 0.052(15) 0.035(12) 0.001(11) 0.019(11) 0.008(11) C3 0.039(13) 0.050(15) 0.037(12) -0.003(11) 0.019(11) 0.006(11) C4 0.043(14) 0.048(15) 0.036(13) -0.005(11) 0.020(11) 0.010(12) C5 0.040(13) 0.052(15) 0.034(12) -0.002(11) 0.020(11) 0.005(12) C6 0.040(14) 0.056(16) 0.038(13) 0.002(12) 0.022(12) 0.008(12) C7 0.050(14) 0.050(15) 0.036(13) 0.002(11) 0.021(11) 0.005(12) C8 0.038(13) 0.044(14) 0.037(13) 0.001(11) 0.019(11) -0.001(11) C9 0.061(16) 0.049(16) 0.041(14) -0.005(12) 0.030(13) -0.005(13) C10 0.057(16) 0.051(16) 0.036(13) -0.001(12) 0.024(12) -0.006(13) C11 0.048(14) 0.048(15) 0.044(14) 0.001(12) 0.020(12) 0.002(12) C12 0.042(14) 0.049(15) 0.035(12) -0.009(11) 0.018(11) -0.001(11) C13 0.045(14) 0.057(16) 0.035(13) -0.005(12) 0.022(11) 0.001(12) C14 0.059(16) 0.048(16) 0.036(13) -0.011(12) 0.020(12) -0.005(13) C15 0.057(17) 0.060(18) 0.041(14) -0.015(13) 0.026(13) -0.022(14) C16 0.040(14) 0.07(2) 0.045(14) -0.016(14) 0.020(12) -0.011(14) C17 0.039(13) 0.049(15) 0.044(14) -0.010(12) 0.021(11) -0.003(11) C18 0.040(13) 0.055(16) 0.034(12) -0.001(11) 0.019(11) 0.005(12) C19 0.040(14) 0.063(17) 0.040(13) -0.004(12) 0.022(12) 0.004(12) C20 0.045(15) 0.071(19) 0.043(14) -0.009(13) 0.024(12) -0.006(14) C21 0.036(13) 0.08(2) 0.037(14) 0.002(14) 0.016(11) 0.003(14) C22 0.042(14) 0.069(18) 0.039(13) 0.001(13) 0.019(12) 0.011(13) C23 0.044(14) 0.061(17) 0.035(13) 0.000(11) 0.021(11) 0.006(12) Cl1 0.043(4) 0.050(4) 0.050(4) 0.005(3) 0.017(3) -0.003(3) O2 0.20(4) 0.09(3) 0.13(3) -0.02(2) 0.10(3) -0.05(3) O3 0.20(4) 0.09(3) 0.13(3) -0.02(2) 0.10(3) -0.05(3) _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 C2 1.37(3) . ? N1 C5 1.38(3) . ? N2 C6 1.36(3) . ? N2 C7 1.46(3) . ? N3 C8 1.33(3) . ? N3 C9 1.37(3) . ? N4 C8 1.34(3) . ? N4 C10 1.39(3) . ? N4 C11 1.47(3) . ? O1 C6 1.23(3) . ? C1 C2 1.50(3) . ? C2 C3 1.38(3) . ? C3 C4 1.43(3) . ? C3 C12 1.48(3) . ? C4 C5 1.39(3) . ? C4 C18 1.49(3) . ? C5 C6 1.47(3) . ? C7 C8 1.49(3) . ? C9 C10 1.35(4) . ? C12 C13 1.40(4) . ? C12 C17 1.41(3) . ? C13 C14 1.39(3) . ? C14 C15 1.39(4) . ? C15 C16 1.39(4) . ? C16 C17 1.37(3) . ? C18 C23 1.39(3) . ? C18 C19 1.40(3) . ? C19 C20 1.39(3) . ? C20 C21 1.39(4) . ? C21 C22 1.39(4) . ? C22 C23 1.38(3) . ? O2 O2 1.39(9) 2 ? 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 C2 N1 C5 110.5(19) . . ? C6 N2 C7 118.8(19) . . ? C8 N3 C9 110(2) . . ? C8 N4 C10 108(2) . . ? C8 N4 C11 125.6(19) . . ? C10 N4 C11 126(2) . . ? N1 C2 C3 108(2) . . ? N1 C2 C1 120(2) . . ? C3 C2 C1 132(2) . . ? C2 C3 C4 108(2) . . ? C2 C3 C12 124(2) . . ? C4 C3 C12 128(2) . . ? C5 C4 C3 107(2) . . ? C5 C4 C18 128(2) . . ? C3 C4 C18 125(2) . . ? N1 C5 C4 107(2) . . ? N1 C5 C6 122(2) . . ? C4 C5 C6 130(2) . . ? O1 C6 N2 120(2) . . ? O1 C6 C5 123(2) . . ? N2 C6 C5 116(2) . . ? N2 C7 C8 112(2) . . ? N3 C8 N4 108.0(19) . . ? N3 C8 C7 126(2) . . ? N4 C8 C7 126(2) . . ? C10 C9 N3 107(2) . . ? C9 C10 N4 107(2) . . ? C13 C12 C17 118(2) . . ? C13 C12 C3 121(2) . . ? C17 C12 C3 121(2) . . ? C14 C13 C12 121(2) . . ? C15 C14 C13 120(2) . . ? C14 C15 C16 120(2) . . ? C17 C16 C15 121(2) . . ? C16 C17 C12 121(2) . . ? C23 C18 C19 118(2) . . ? C23 C18 C4 121(2) . . ? C19 C18 C4 120(2) . . ? C20 C19 C18 121(2) . . ? C21 C20 C19 120(3) . . ? C20 C21 C22 120(2) . . ? C23 C22 C21 121(2) . . ? C22 C23 C18 121(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Cl1 0.88 2.38 3.24(2) 164.6 2 N2 H2 Cl1 0.88 2.42 3.29(2) 171.0 2 N3 H3 Cl1 0.88 2.23 3.10(2) 171.9 6_565 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.606 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.065