# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_address ;Institute of Applied chemistry Xinjiang University Urumqi Xinjiang 830 046 China ; _publ_contact_author_address ;Institute of Applied chemistry Xinjiang University Urumqi Xinjiang 830 046 China ; _publ_contact_author_email jdz@gmail.com _publ_contact_author_phone '+86 991 858 3083' #TrackingRef 'g0709.CIF' _publ_contact_author_name 'Dianzeng, Jia' loop_ _publ_author_name 'Jixi Guo' 'Dianzeng Jia' data_g0750 _database_code_depnum_ccdc_archive 'CCDC 797540' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H19 Cl F N5 O S' _chemical_formula_weight 479.95 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 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 12.4255(8) _cell_length_b 14.4075(8) _cell_length_c 13.4165(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.9890(10) _cell_angle_gamma 90.00 _cell_volume 2284.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10900 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 27.46 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-axis Spider' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17794 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4207 _reflns_number_gt 2783 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_cell_refinement 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_data_reduction 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Bruker AXS, 2000)' _computing_publication_material 'SHELXTL 5.1 (Bruker AXS, 2000)' _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^)+(0.1281P)^2^+1.9984P] 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 0.027(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4207 _refine_ls_number_parameters 370 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.1091 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.2482 _refine_ls_wR_factor_gt 0.1843 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.085 _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 Cl Cl 0.67099(13) 0.65398(13) 0.93441(11) 0.0831(7) Uani 0.871(4) 1 d PD A 1 Cl' Cl 0.8282(11) 0.7756(8) 0.6709(9) 0.091(4) Uani 0.129(4) 1 d PD A 2 S S 0.20957(9) 0.64780(9) 0.58802(9) 0.0648(4) Uani 1 1 d . . . F F 1.1196(3) 0.4723(3) 0.8932(3) 0.1332(16) Uani 1 1 d . . . O O 0.4639(3) 0.6776(2) 0.4600(2) 0.0650(8) Uani 1 1 d D . . N1 N 0.5953(3) 0.5776(2) 0.4283(2) 0.0548(9) Uani 1 1 d . . . N2 N 0.6998(3) 0.5427(3) 0.4871(3) 0.0564(9) Uani 1 1 d D . . N3 N 0.5327(3) 0.6897(2) 0.7159(3) 0.0529(8) Uani 1 1 d . A . N4 N 0.4296(3) 0.6607(2) 0.6483(3) 0.0538(9) Uani 1 1 d D . . N5 N 0.3487(3) 0.6967(3) 0.7756(3) 0.0629(10) Uani 1 1 d D . . C1 C 0.4507(4) 0.5900(3) 0.2607(3) 0.0616(11) Uani 1 1 d . . . H1A H 0.3959 0.5956 0.2944 0.074 Uiso 1 1 calc R . . C2 C 0.4215(4) 0.5938(3) 0.1523(3) 0.0683(12) Uani 1 1 d . . . H2A H 0.3465 0.6045 0.1133 0.082 Uiso 1 1 calc R . . C3 C 0.5005(5) 0.5821(4) 0.1013(4) 0.0723(13) Uani 1 1 d . . . H3A H 0.4791 0.5841 0.0285 0.087 Uiso 1 1 calc R . . C4 C 0.6117(5) 0.5673(4) 0.1587(4) 0.0738(13) Uani 1 1 d . . . H4A H 0.6655 0.5583 0.1244 0.089 Uiso 1 1 calc R . . C5 C 0.6443(4) 0.5657(3) 0.2681(3) 0.0623(11) Uani 1 1 d . . . H5A H 0.7197 0.5567 0.3070 0.075 Uiso 1 1 calc R . . C6 C 0.5634(4) 0.5777(3) 0.3173(3) 0.0524(10) Uani 1 1 d . . . C7 C 0.5523(3) 0.6306(3) 0.4933(3) 0.0524(10) Uani 1 1 d . . . C8 C 0.6295(3) 0.6211(3) 0.5974(3) 0.0501(9) Uani 1 1 d . A . C9 C 0.7173(3) 0.5656(3) 0.5892(3) 0.0500(9) Uani 1 1 d . . . C10 C 0.8214(3) 0.5339(3) 0.6673(3) 0.0530(10) Uani 1 1 d . . . C11 C 0.9239(4) 0.5371(4) 0.6448(4) 0.0679(12) Uani 1 1 d . . . H11A H 0.9240 0.5535 0.5778 0.081 Uiso 1 1 calc R . . C12 C 1.0243(4) 0.5164(4) 0.7198(4) 0.0794(14) Uani 1 1 d . . . H12A H 1.0926 0.5189 0.7051 0.095 Uiso 1 1 calc R . . C13 C 1.0200(4) 0.4918(4) 0.8172(4) 0.0826(15) Uani 1 1 d . . . C14 C 0.9226(4) 0.4852(4) 0.8422(4) 0.0763(14) Uani 1 1 d . . . H14A H 0.9232 0.4662 0.9087 0.092 Uiso 1 1 calc R . . C15 C 0.8232(4) 0.5073(3) 0.7665(3) 0.0599(11) Uani 1 1 d . . . H15A H 0.7556 0.5043 0.7825 0.072 Uiso 1 1 calc R . . C16 C 0.6233(3) 0.6707(3) 0.6910(3) 0.0495(9) Uani 1 1 d D . . C17 C 0.7327(3) 0.7074(3) 0.7635(3) 0.0451(11) Uani 0.871(4) 1 d PD A 1 C18 C 0.8091(3) 0.7465(4) 0.7194(3) 0.0624(14) Uani 0.871(4) 1 d PD A 1 H18A H 0.7904 0.7521 0.6470 0.075 Uiso 0.871(4) 1 calc PR A 1 C19 C 0.9135(3) 0.7774(4) 0.7827(3) 0.0755(16) Uani 0.871(4) 1 d PD A 1 H19A H 0.9648 0.8032 0.7527 0.091 Uiso 0.871(4) 1 calc PR A 1 C20 C 0.9414(4) 0.7700(5) 0.8906(3) 0.089(2) Uani 0.871(4) 1 d PD A 1 H20A H 1.0127 0.7881 0.9330 0.107 Uiso 0.871(4) 1 calc PR A 1 C21 C 0.8628(4) 0.7355(5) 0.9352(3) 0.082(2) Uani 0.871(4) 1 d PD A 1 H21A H 0.8797 0.7338 1.0077 0.098 Uiso 0.871(4) 1 calc PR A 1 C22 C 0.7591(3) 0.7034(4) 0.8719(3) 0.0600(14) Uani 0.871(4) 1 d PD A 1 C17' C 0.7150(12) 0.689(2) 0.7923(6) 0.065(14) Uani 0.129(4) 1 d PD A 2 C18' C 0.719(2) 0.6452(18) 0.8859(13) 0.11(2) Uani 0.129(4) 1 d PD A 2 H18B H 0.6645 0.6019 0.8879 0.132 Uiso 0.129(4) 1 calc PR A 2 C19' C 0.806(2) 0.667(3) 0.9766(8) 0.087(12) Uiso 0.129(4) 1 d PD A 2 H19B H 0.7991 0.6528 1.0419 0.105 Uiso 0.129(4) 1 calc PR A 2 C20' C 0.904(2) 0.709(2) 0.9689(12) 0.12(3) Uani 0.129(4) 1 d PD A 2 H20B H 0.9684 0.7124 1.0268 0.140 Uiso 0.129(4) 1 calc PR A 2 C21' C 0.9032(17) 0.746(3) 0.8732(19) 0.087(15) Uiso 0.129(4) 1 d PD A 2 H21B H 0.9612 0.7855 0.8693 0.104 Uiso 0.129(4) 1 calc PR A 2 C22' C 0.8155(15) 0.725(2) 0.7834(12) 0.075(12) Uani 0.129(4) 1 d PD A 2 C23 C 0.3364(3) 0.6715(3) 0.6779(3) 0.0530(10) Uani 1 1 d . . . C24 C 0.2579(4) 0.7099(5) 0.8198(4) 0.0937(19) Uani 1 1 d . . . H24A H 0.2885 0.7282 0.8919 0.141 Uiso 1 1 calc R . . H24B H 0.2167 0.6529 0.8156 0.141 Uiso 1 1 calc R . . H24C H 0.2079 0.7575 0.7815 0.141 Uiso 1 1 calc R . . H1O H 0.427(16) 0.658(16) 0.496(15) 0.17(12) Uiso 0.37(9) 1 d PD B 1 H2N H 0.720(4) 0.491(2) 0.466(4) 0.03(2) Uiso 0.63(9) 1 d PD B 2 H4N H 0.430(5) 0.666(4) 0.5845(18) 0.11(2) Uiso 1 1 d D . . H5N H 0.416(2) 0.710(4) 0.815(3) 0.083(17) 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 Cl 0.0710(10) 0.1222(14) 0.0550(8) 0.0103(7) 0.0176(7) -0.0047(8) Cl' 0.108(9) 0.080(8) 0.091(8) 0.014(6) 0.042(7) -0.026(6) S 0.0463(7) 0.0794(9) 0.0628(7) -0.0121(5) 0.0082(5) 0.0053(5) F 0.063(2) 0.209(5) 0.104(3) 0.010(3) -0.0097(18) 0.039(2) O 0.0565(19) 0.085(2) 0.0505(16) 0.0013(14) 0.0126(14) 0.0189(16) N1 0.052(2) 0.064(2) 0.0468(18) -0.0003(14) 0.0127(15) 0.0075(16) N2 0.052(2) 0.062(2) 0.0538(19) -0.0055(15) 0.0137(15) 0.0083(17) N3 0.0381(18) 0.061(2) 0.0550(19) -0.0058(15) 0.0081(14) -0.0010(15) N4 0.0427(19) 0.064(2) 0.054(2) -0.0058(15) 0.0145(15) 0.0016(15) N5 0.051(2) 0.084(3) 0.055(2) -0.0165(18) 0.0172(17) -0.0069(19) C1 0.054(3) 0.071(3) 0.056(2) -0.0067(19) 0.012(2) -0.007(2) C2 0.069(3) 0.076(3) 0.052(2) -0.005(2) 0.007(2) -0.003(2) C3 0.090(4) 0.077(3) 0.053(2) -0.001(2) 0.026(2) -0.007(3) C4 0.087(4) 0.081(3) 0.062(3) 0.005(2) 0.036(3) 0.004(3) C5 0.065(3) 0.074(3) 0.052(2) 0.0017(19) 0.025(2) 0.006(2) C6 0.064(3) 0.052(2) 0.0428(19) 0.0001(15) 0.0184(18) -0.0023(19) C7 0.048(2) 0.059(2) 0.050(2) 0.0010(17) 0.0142(17) 0.0064(18) C8 0.043(2) 0.057(2) 0.048(2) -0.0020(16) 0.0126(16) 0.0007(17) C9 0.045(2) 0.054(2) 0.050(2) -0.0017(16) 0.0148(17) 0.0007(17) C10 0.043(2) 0.054(2) 0.060(2) -0.0022(17) 0.0123(17) 0.0036(17) C11 0.049(3) 0.082(3) 0.077(3) 0.002(2) 0.026(2) 0.005(2) C12 0.052(3) 0.094(4) 0.091(4) -0.003(3) 0.019(3) 0.011(2) C13 0.049(3) 0.104(4) 0.081(3) 0.000(3) -0.001(2) 0.014(3) C14 0.057(3) 0.105(4) 0.062(3) 0.007(2) 0.010(2) 0.011(3) C15 0.047(2) 0.074(3) 0.058(2) 0.0030(19) 0.0157(19) 0.001(2) C16 0.039(2) 0.057(2) 0.050(2) -0.0038(16) 0.0095(16) 0.0032(17) C17 0.040(3) 0.054(3) 0.048(3) -0.005(2) 0.023(2) -0.007(2) C18 0.054(3) 0.063(4) 0.069(4) -0.004(3) 0.016(3) -0.007(3) C19 0.060(3) 0.082(4) 0.084(4) -0.009(3) 0.021(3) -0.018(3) C20 0.059(4) 0.113(6) 0.083(4) -0.020(4) 0.003(3) -0.025(4) C21 0.070(4) 0.105(6) 0.059(3) -0.015(3) 0.004(3) -0.006(4) C22 0.051(3) 0.075(4) 0.048(3) -0.008(2) 0.006(2) 0.001(2) C17' 0.07(2) 0.09(2) 0.09(3) -0.030(18) 0.11(2) -0.064(18) C18' 0.06(2) 0.18(5) 0.12(4) -0.09(4) 0.06(3) 0.01(3) C20' 0.10(4) 0.05(2) 0.17(6) -0.06(3) -0.01(4) 0.05(3) C22' 0.06(3) 0.06(2) 0.11(4) 0.00(2) 0.05(3) -0.01(2) C23 0.047(2) 0.053(2) 0.058(2) -0.0046(17) 0.0150(18) 0.0004(17) C24 0.065(3) 0.145(6) 0.081(3) -0.043(3) 0.037(3) -0.024(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 Cl C22 1.726(3) . ? Cl' C22' 1.729(3) . ? S C23 1.697(4) . ? F C13 1.368(5) . ? O C7 1.250(5) . ? O H1O 0.820(10) . ? N1 C7 1.384(5) . ? N1 N2 1.389(5) . ? N1 C6 1.419(5) . ? N2 C9 1.360(5) . ? N2 H2N 0.861(10) . ? N3 C16 1.299(5) . ? N3 N4 1.385(4) . ? N4 C23 1.344(5) . ? N4 H4N 0.862(10) . ? N5 C23 1.323(5) . ? N5 C24 1.441(6) . ? N5 H5N 0.861(10) . ? C1 C6 1.383(6) . ? C1 C2 1.387(6) . ? C1 H1A 0.9300 . ? C2 C3 1.369(7) . ? C2 H2A 0.9300 . ? C3 C4 1.375(7) . ? C3 H3A 0.9300 . ? C4 C5 1.398(6) . ? C4 H4A 0.9300 . ? C5 C6 1.373(6) . ? C5 H5A 0.9300 . ? C7 C8 1.436(5) . ? C8 C9 1.383(5) . ? C8 C16 1.468(5) . ? C9 C10 1.464(5) . ? C10 C15 1.379(6) . ? C10 C11 1.397(6) . ? C11 C12 1.372(7) . ? C11 H11A 0.9300 . ? C12 C13 1.370(8) . ? C12 H12A 0.9300 . ? C13 C14 1.355(7) . ? C14 C15 1.373(6) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 C17 1.502(3) . ? C16 C17' 1.502(3) . ? C17 C18 1.385(3) . ? C17 C22 1.389(3) . ? C18 C19 1.386(3) . ? C18 H18A 0.9300 . ? C19 C20 1.385(3) . ? C19 H19A 0.9300 . ? C20 C21 1.386(3) . ? C20 H20A 0.9300 . ? C21 C22 1.386(3) . ? C21 H21A 0.9300 . ? C17' C22' 1.390(3) . ? C17' C18' 1.390(3) . ? C18' C19' 1.389(3) . ? C18' H18B 0.9300 . ? C19' C20' 1.389(3) . ? C19' H19B 0.9300 . ? C20' C21' 1.389(3) . ? C20' H20B 0.9300 . ? C21' C22' 1.389(3) . ? C21' H21B 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O H1O 101(10) . . ? C7 N1 N2 108.5(3) . . ? C7 N1 C6 128.6(3) . . ? N2 N1 C6 120.4(3) . . ? C9 N2 N1 108.3(3) . . ? C9 N2 H2N 124(4) . . ? N1 N2 H2N 116(4) . . ? C16 N3 N4 117.9(3) . . ? C23 N4 N3 118.6(3) . . ? C23 N4 H4N 124(4) . . ? N3 N4 H4N 109(4) . . ? C23 N5 C24 125.4(4) . . ? C23 N5 H5N 118(4) . . ? C24 N5 H5N 116(4) . . ? C6 C1 C2 118.2(4) . . ? C6 C1 H1A 120.9 . . ? C2 C1 H1A 120.9 . . ? C3 C2 C1 121.6(5) . . ? C3 C2 H2A 119.2 . . ? C1 C2 H2A 119.2 . . ? C2 C3 C4 119.4(4) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C6 C5 C4 119.0(4) . . ? C6 C5 H5A 120.5 . . ? C4 C5 H5A 120.5 . . ? C5 C6 C1 121.4(4) . . ? C5 C6 N1 119.7(4) . . ? C1 C6 N1 118.9(4) . . ? O C7 N1 122.8(4) . . ? O C7 C8 130.5(4) . . ? N1 C7 C8 106.7(3) . . ? C9 C8 C7 106.5(3) . . ? C9 C8 C16 126.9(3) . . ? C7 C8 C16 126.1(3) . . ? N2 C9 C8 109.6(3) . . ? N2 C9 C10 118.4(3) . . ? C8 C9 C10 131.9(4) . . ? C15 C10 C11 118.3(4) . . ? C15 C10 C9 121.6(4) . . ? C11 C10 C9 119.8(4) . . ? C12 C11 C10 121.1(5) . . ? C12 C11 H11A 119.4 . . ? C10 C11 H11A 119.4 . . ? C13 C12 C11 117.4(5) . . ? C13 C12 H12A 121.3 . . ? C11 C12 H12A 121.3 . . ? C14 C13 F 118.1(5) . . ? C14 C13 C12 123.7(5) . . ? F C13 C12 118.1(5) . . ? C13 C14 C15 117.9(5) . . ? C13 C14 H14A 121.0 . . ? C15 C14 H14A 121.0 . . ? C14 C15 C10 121.4(4) . . ? C14 C15 H15A 119.3 . . ? C10 C15 H15A 119.3 . . ? N3 C16 C8 127.0(3) . . ? N3 C16 C17 116.2(3) . . ? C8 C16 C17 116.7(3) . . ? N3 C16 C17' 101.9(9) . . ? C8 C16 C17' 129.2(11) . . ? C17 C16 C17' 21.8(6) . . ? C18 C17 C22 119.5(3) . . ? C18 C17 C16 118.0(3) . . ? C22 C17 C16 122.5(3) . . ? C17 C18 C19 120.3(3) . . ? C17 C18 H18A 119.9 . . ? C19 C18 H18A 119.9 . . ? C20 C19 C18 120.1(3) . . ? C20 C19 H19A 120.0 . . ? C18 C19 H19A 120.0 . . ? C19 C20 C21 119.8(3) . . ? C19 C20 H20A 120.1 . . ? C21 C20 H20A 120.1 . . ? C22 C21 C20 120.0(3) . . ? C22 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C21 C22 C17 120.2(2) . . ? C21 C22 Cl 116.7(3) . . ? C17 C22 Cl 123.1(3) . . ? C22' C17' C18' 117.4(13) . . ? C22' C17' C16 115.9(11) . . ? C18' C17' C16 123.2(14) . . ? C19' C18' C17' 119.6(4) . . ? C19' C18' H18B 120.2 . . ? C17' C18' H18B 120.2 . . ? C18' C19' C20' 119.5(4) . . ? C18' C19' H19B 120.2 . . ? C20' C19' H19B 120.2 . . ? C21' C20' C19' 118.8(10) . . ? C21' C20' H20B 120.6 . . ? C19' C20' H20B 120.6 . . ? C22' C21' C20' 119.6(4) . . ? C22' C21' H21B 120.2 . . ? C20' C21' H21B 120.2 . . ? C21' C22' C17' 119.6(4) . . ? C21' C22' Cl' 113.7(14) . . ? C17' C22' Cl' 124.1(13) . . ? N5 C23 N4 118.5(4) . . ? N5 C23 S 123.8(3) . . ? N4 C23 S 117.6(3) . . ? N5 C24 H24A 109.5 . . ? N5 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N5 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 C7 N1 N2 C9 5.9(5) . . . . ? C6 N1 N2 C9 169.4(3) . . . . ? C16 N3 N4 C23 173.4(4) . . . . ? C6 C1 C2 C3 2.6(7) . . . . ? C1 C2 C3 C4 -0.8(8) . . . . ? C2 C3 C4 C5 -1.0(8) . . . . ? C3 C4 C5 C6 1.0(7) . . . . ? C4 C5 C6 C1 0.9(7) . . . . ? C4 C5 C6 N1 -179.1(4) . . . . ? C2 C1 C6 C5 -2.6(7) . . . . ? C2 C1 C6 N1 177.4(4) . . . . ? C7 N1 C6 C5 143.4(4) . . . . ? N2 N1 C6 C5 -16.4(6) . . . . ? C7 N1 C6 C1 -36.6(6) . . . . ? N2 N1 C6 C1 163.6(4) . . . . ? N2 N1 C7 O 173.4(4) . . . . ? C6 N1 C7 O 11.7(7) . . . . ? N2 N1 C7 C8 -4.9(4) . . . . ? C6 N1 C7 C8 -166.6(4) . . . . ? O C7 C8 C9 -175.9(5) . . . . ? N1 C7 C8 C9 2.2(5) . . . . ? O C7 C8 C16 -3.3(7) . . . . ? N1 C7 C8 C16 174.8(4) . . . . ? N1 N2 C9 C8 -4.5(5) . . . . ? N1 N2 C9 C10 178.3(3) . . . . ? C7 C8 C9 N2 1.4(5) . . . . ? C16 C8 C9 N2 -171.2(4) . . . . ? C7 C8 C9 C10 178.1(4) . . . . ? C16 C8 C9 C10 5.5(7) . . . . ? N2 C9 C10 C15 -144.0(4) . . . . ? C8 C9 C10 C15 39.6(7) . . . . ? N2 C9 C10 C11 41.1(6) . . . . ? C8 C9 C10 C11 -135.3(5) . . . . ? C15 C10 C11 C12 -1.4(7) . . . . ? C9 C10 C11 C12 173.6(4) . . . . ? C10 C11 C12 C13 0.5(8) . . . . ? C11 C12 C13 C14 1.4(9) . . . . ? C11 C12 C13 F -179.1(5) . . . . ? F C13 C14 C15 178.3(5) . . . . ? C12 C13 C14 C15 -2.2(9) . . . . ? C13 C14 C15 C10 1.2(8) . . . . ? C11 C10 C15 C14 0.6(7) . . . . ? C9 C10 C15 C14 -174.4(4) . . . . ? N4 N3 C16 C8 0.1(6) . . . . ? N4 N3 C16 C17 177.1(3) . . . . ? N4 N3 C16 C17' -165.4(13) . . . . ? C9 C8 C16 N3 -149.1(4) . . . . ? C7 C8 C16 N3 39.7(7) . . . . ? C9 C8 C16 C17 33.9(6) . . . . ? C7 C8 C16 C17 -137.3(4) . . . . ? C9 C8 C16 C17' 12.4(15) . . . . ? C7 C8 C16 C17' -158.7(14) . . . . ? N3 C16 C17 C18 -137.1(5) . . . . ? C8 C16 C17 C18 40.2(6) . . . . ? C17' C16 C17 C18 171(4) . . . . ? N3 C16 C17 C22 42.9(6) . . . . ? C8 C16 C17 C22 -139.8(5) . . . . ? C17' C16 C17 C22 -9(4) . . . . ? C22 C17 C18 C19 3.0(8) . . . . ? C16 C17 C18 C19 -177.0(5) . . . . ? C17 C18 C19 C20 -0.5(10) . . . . ? C18 C19 C20 C21 -2.9(11) . . . . ? C19 C20 C21 C22 3.8(12) . . . . ? C20 C21 C22 C17 -1.3(10) . . . . ? C20 C21 C22 Cl 175.4(6) . . . . ? C18 C17 C22 C21 -2.1(9) . . . . ? C16 C17 C22 C21 177.9(5) . . . . ? C18 C17 C22 Cl -178.6(4) . . . . ? C16 C17 C22 Cl 1.4(7) . . . . ? N3 C16 C17' C22' -146(3) . . . . ? C8 C16 C17' C22' 49(4) . . . . ? C17 C16 C17' C22' -12(2) . . . . ? N3 C16 C17' C18' 56(3) . . . . ? C8 C16 C17' C18' -109(2) . . . . ? C17 C16 C17' C18' -170(6) . . . . ? C22' C17' C18' C19' 23(4) . . . . ? C16 C17' C18' C19' -179(3) . . . . ? C17' C18' C19' C20' -19(4) . . . . ? C18' C19' C20' C21' 13(6) . . . . ? C19' C20' C21' C22' -13(6) . . . . ? C20' C21' C22' C17' 18(5) . . . . ? C20' C21' C22' Cl' -179(4) . . . . ? C18' C17' C22' C21' -23(5) . . . . ? C16 C17' C22' C21' 178(3) . . . . ? C18' C17' C22' Cl' 177(2) . . . . ? C16 C17' C22' Cl' 17(5) . . . . ? C24 N5 C23 N4 -179.1(5) . . . . ? C24 N5 C23 S -1.5(7) . . . . ? N3 N4 C23 N5 -9.6(6) . . . . ? N3 N4 C23 S 172.6(3) . . . . ? 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 N2 H2N S 0.861(10) 2.385(12) 3.243(4) 175(5) 3_666 N4 H4N O 0.862(10) 1.850(17) 2.700(5) 168(6) . O H1O N4 0.820(10) 2.03(15) 2.700(5) 139(21) . N5 H5N N3 0.861(10) 2.28(5) 2.647(5) 106(4) . N5 H5N O 0.861(10) 2.45(4) 3.043(5) 126(4) 4_576 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.451 _refine_diff_density_min -0.513 _refine_diff_density_rms 0.094 # Attachment 'g0750.CIF' data_g0709 _database_code_depnum_ccdc_archive 'CCDC 797541' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H19 Cl F N5 O S' _chemical_formula_weight 479.95 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 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 12.4127(16) _cell_length_b 14.3970(18) _cell_length_c 13.3934(14) _cell_angle_alpha 90.00 _cell_angle_beta 108.020(2) _cell_angle_gamma 90.00 _cell_volume 2276.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9285 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 27.51 _exptl_crystal_description chunk _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.295 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-axis Spider' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17943 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4200 _reflns_number_gt 2888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_cell_refinement 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_data_reduction 'Rapid Auto Version 3.0 (Rigaku 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Bruker AXS, 2000)' _computing_publication_material 'SHELXTL 5.1 (Bruker AXS, 2000)' _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^)+(0.1285P)^2^+1.1983P] 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 0.005(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4200 _refine_ls_number_parameters 312 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.2285 _refine_ls_wR_factor_gt 0.1948 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.073 _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 Cl Cl 0.67155(11) 0.65408(10) 0.93508(9) 0.0849(5) Uani 1 1 d D . . S S 0.20952(8) 0.64702(8) 0.58883(8) 0.0582(4) Uani 1 1 d . . . F F 1.1194(3) 0.4715(3) 0.8937(2) 0.1187(13) Uani 1 1 d . . . O O 0.4633(2) 0.6775(2) 0.46029(18) 0.0582(7) Uani 1 1 d . . . N1 N 0.5955(2) 0.5774(2) 0.4287(2) 0.0486(7) Uani 1 1 d . . . N2 N 0.6991(3) 0.5425(2) 0.4875(2) 0.0494(7) Uani 1 1 d D . . N3 N 0.5321(2) 0.6902(2) 0.7159(2) 0.0463(7) Uani 1 1 d . . . N4 N 0.4307(2) 0.6608(2) 0.6493(2) 0.0473(7) Uani 1 1 d D . . N5 N 0.3490(3) 0.6967(3) 0.7763(2) 0.0575(8) Uani 1 1 d D . . C1 C 0.4506(3) 0.5904(3) 0.2603(3) 0.0555(10) Uani 1 1 d . . . H1 H 0.3961 0.5963 0.2943 0.067 Uiso 1 1 calc R . . C2 C 0.4202(4) 0.5942(3) 0.1518(3) 0.0649(11) Uani 1 1 d . . . H2 H 0.3451 0.6047 0.1128 0.078 Uiso 1 1 calc R . . C3 C 0.5007(4) 0.5826(3) 0.1012(3) 0.0653(11) Uani 1 1 d . . . H3 H 0.4796 0.5849 0.0283 0.078 Uiso 1 1 calc R . . C4 C 0.6116(4) 0.5676(3) 0.1580(3) 0.0666(12) Uani 1 1 d . . . H4 H 0.6653 0.5586 0.1236 0.080 Uiso 1 1 calc R . . C5 C 0.6443(4) 0.5658(3) 0.2674(3) 0.0560(10) Uani 1 1 d . . . H5 H 0.7198 0.5567 0.3064 0.067 Uiso 1 1 calc R . . C6 C 0.5629(3) 0.5777(2) 0.3171(3) 0.0480(8) Uani 1 1 d . . . C7 C 0.5507(3) 0.6310(3) 0.4930(3) 0.0489(8) Uani 1 1 d . . . C8 C 0.6293(3) 0.6214(2) 0.5972(2) 0.0430(8) Uani 1 1 d . . . C9 C 0.7173(3) 0.5660(2) 0.5895(2) 0.0442(8) Uani 1 1 d . . . C10 C 0.8214(3) 0.5346(2) 0.6672(3) 0.0450(8) Uani 1 1 d . . . C11 C 0.9229(3) 0.5367(3) 0.6450(3) 0.0601(10) Uani 1 1 d . . . H11 H 0.9233 0.5529 0.5779 0.072 Uiso 1 1 calc R . . C12 C 1.0235(4) 0.5151(4) 0.7206(4) 0.0722(12) Uani 1 1 d . . . H12 H 1.0919 0.5175 0.7058 0.087 Uiso 1 1 calc R . . C13 C 1.0200(4) 0.4904(4) 0.8173(4) 0.0739(13) Uani 1 1 d . . . C14 C 0.9223(4) 0.4854(3) 0.8428(3) 0.0673(11) Uani 1 1 d . . . H14 H 0.9228 0.4676 0.9097 0.081 Uiso 1 1 calc R . . C15 C 0.8225(3) 0.5075(3) 0.7666(3) 0.0526(9) Uani 1 1 d . . . H15 H 0.7546 0.5042 0.7822 0.063 Uiso 1 1 calc R . . C16 C 0.6226(3) 0.6715(2) 0.6914(2) 0.0436(8) Uani 1 1 d . . . C17 C 0.7303(3) 0.7069(3) 0.7645(3) 0.0483(8) Uani 1 1 d . . . C18 C 0.8122(3) 0.7487(3) 0.7181(4) 0.0730(13) Uani 1 1 d . . . H18 H 0.7947 0.7551 0.6457 0.088 Uiso 1 1 calc R . . C19 C 0.9128(4) 0.7774(4) 0.7827(4) 0.0786(13) Uani 1 1 d . . . H19 H 0.9654 0.8033 0.7542 0.094 Uiso 1 1 calc R . . C20 C 0.9397(4) 0.7692(4) 0.8904(4) 0.0866(15) Uani 1 1 d . . . H20 H 1.0111 0.7872 0.9328 0.104 Uiso 1 1 calc R . . C21 C 0.8641(4) 0.7354(4) 0.9356(4) 0.0814(14) Uani 1 1 d . . . H21 H 0.8818 0.7339 1.0083 0.098 Uiso 1 1 calc R . . C22 C 0.7604(3) 0.7033(3) 0.8729(3) 0.0626(11) Uani 1 1 d D . . C23 C 0.3360(3) 0.6708(3) 0.6789(3) 0.0478(8) Uani 1 1 d . . . C24 C 0.2577(4) 0.7093(4) 0.8211(4) 0.0831(15) Uani 1 1 d . . . H24A H 0.2046 0.7538 0.7801 0.100 Uiso 1 1 calc R . . H24B H 0.2879 0.7314 0.8919 0.100 Uiso 1 1 calc R . . H24C H 0.2199 0.6511 0.8209 0.100 Uiso 1 1 calc R . . H2N H 0.719(4) 0.4934(18) 0.461(3) 0.069(13) Uiso 1 1 d D . . H4N H 0.421(3) 0.661(2) 0.5828(10) 0.042(9) Uiso 1 1 d D . . H5N H 0.4189(14) 0.711(3) 0.802(3) 0.083(16) 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 Cl 0.0731(9) 0.1270(12) 0.0551(7) 0.0128(6) 0.0207(6) -0.0025(7) S 0.0388(6) 0.0747(7) 0.0565(6) -0.0114(4) 0.0080(4) 0.0053(4) F 0.0580(18) 0.178(4) 0.096(2) 0.010(2) -0.0114(15) 0.034(2) O 0.0482(16) 0.0796(19) 0.0446(14) 0.0042(12) 0.0111(11) 0.0187(14) N1 0.0446(18) 0.0609(19) 0.0399(15) -0.0009(12) 0.0124(13) 0.0050(14) N2 0.0450(18) 0.058(2) 0.0454(16) -0.0034(13) 0.0134(13) 0.0080(14) N3 0.0376(16) 0.0546(18) 0.0470(15) -0.0040(12) 0.0134(12) 0.0005(13) N4 0.0397(17) 0.0609(19) 0.0393(16) -0.0054(12) 0.0095(13) 0.0016(13) N5 0.045(2) 0.079(2) 0.0505(18) -0.0154(15) 0.0180(15) -0.0103(17) C1 0.049(2) 0.069(3) 0.047(2) -0.0046(16) 0.0136(17) -0.0077(18) C2 0.069(3) 0.073(3) 0.047(2) -0.0041(18) 0.0087(19) -0.009(2) C3 0.082(3) 0.069(3) 0.044(2) -0.0023(17) 0.019(2) -0.002(2) C4 0.082(3) 0.074(3) 0.055(2) 0.0013(19) 0.037(2) 0.003(2) C5 0.058(2) 0.063(2) 0.053(2) 0.0030(17) 0.0258(18) 0.0047(19) C6 0.057(2) 0.0446(19) 0.0438(18) -0.0009(14) 0.0172(16) -0.0036(16) C7 0.045(2) 0.056(2) 0.0459(19) -0.0007(15) 0.0143(15) 0.0016(17) C8 0.0381(19) 0.0483(19) 0.0418(17) 0.0015(13) 0.0111(14) 0.0029(15) C9 0.041(2) 0.049(2) 0.0436(18) -0.0002(14) 0.0142(14) -0.0012(15) C10 0.0364(19) 0.049(2) 0.0493(19) -0.0020(14) 0.0130(14) 0.0019(15) C11 0.046(2) 0.073(3) 0.063(2) 0.0005(18) 0.0200(19) 0.0069(19) C12 0.040(2) 0.095(3) 0.080(3) -0.006(2) 0.018(2) 0.007(2) C13 0.045(3) 0.094(3) 0.071(3) -0.003(2) 0.000(2) 0.018(2) C14 0.056(3) 0.083(3) 0.057(2) 0.007(2) 0.0093(19) 0.007(2) C15 0.043(2) 0.060(2) 0.054(2) 0.0015(16) 0.0136(16) 0.0007(17) C16 0.041(2) 0.0475(19) 0.0410(17) -0.0024(13) 0.0099(14) 0.0015(15) C17 0.042(2) 0.055(2) 0.0449(18) -0.0073(14) 0.0097(15) 0.0021(16) C18 0.040(2) 0.066(3) 0.099(3) -0.031(2) 0.001(2) -0.0010(19) C19 0.061(3) 0.090(3) 0.088(3) -0.008(2) 0.026(2) -0.018(2) C20 0.056(3) 0.112(4) 0.080(3) -0.018(3) 0.006(2) -0.014(3) C21 0.065(3) 0.112(4) 0.060(3) -0.024(2) 0.009(2) -0.010(3) C22 0.053(2) 0.074(3) 0.060(2) -0.0056(19) 0.0145(19) 0.007(2) C23 0.039(2) 0.052(2) 0.053(2) -0.0029(15) 0.0161(15) 0.0021(15) C24 0.062(3) 0.124(4) 0.075(3) -0.034(3) 0.038(2) -0.017(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 Cl C22 1.727(3) . ? S C23 1.693(4) . ? F C13 1.364(5) . ? O C7 1.235(4) . ? N1 N2 1.378(4) . ? N1 C7 1.394(4) . ? N1 C6 1.422(4) . ? N2 C9 1.357(4) . ? N2 H2N 0.860(10) . ? N3 C16 1.292(4) . ? N3 N4 1.366(4) . ? N4 C23 1.359(4) . ? N4 H4N 0.861(10) . ? N5 C23 1.318(5) . ? N5 C24 1.448(5) . ? N5 H5N 0.855(10) . ? C1 C6 1.378(5) . ? C1 C2 1.385(5) . ? C1 H1 0.9300 . ? C2 C3 1.380(6) . ? C2 H2 0.9300 . ? C3 C4 1.367(6) . ? C3 H3 0.9300 . ? C4 C5 1.395(5) . ? C4 H4 0.9300 . ? C5 C6 1.381(5) . ? C5 H5 0.9300 . ? C7 C8 1.440(5) . ? C8 C9 1.382(5) . ? C8 C16 1.478(4) . ? C9 C10 1.458(5) . ? C10 C11 1.381(5) . ? C10 C15 1.383(5) . ? C11 C12 1.379(6) . ? C11 H11 0.9300 . ? C12 C13 1.357(6) . ? C12 H12 0.9300 . ? C13 C14 1.360(7) . ? C14 C15 1.377(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.482(5) . ? C17 C22 1.383(5) . ? C17 C18 1.475(6) . ? C18 C19 1.345(6) . ? C18 H18 0.9300 . ? C19 C20 1.383(7) . ? C19 H19 0.9300 . ? C20 C21 1.354(7) . ? C20 H20 0.9300 . ? C21 C22 1.380(6) . ? C21 H21 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C7 109.1(3) . . ? N2 N1 C6 120.9(3) . . ? C7 N1 C6 127.6(3) . . ? C9 N2 N1 108.7(3) . . ? C9 N2 H2N 130(3) . . ? N1 N2 H2N 113(3) . . ? C16 N3 N4 117.9(3) . . ? C23 N4 N3 118.9(3) . . ? C23 N4 H4N 117(2) . . ? N3 N4 H4N 118(2) . . ? C23 N5 C24 125.0(3) . . ? C23 N5 H5N 106(3) . . ? C24 N5 H5N 129(3) . . ? C6 C1 C2 119.0(4) . . ? C6 C1 H1 120.5 . . ? C2 C1 H1 120.5 . . ? C3 C2 C1 120.4(4) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C4 C3 C2 120.2(4) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.2(4) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 119.0(4) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C1 C6 C5 121.1(3) . . ? C1 C6 N1 119.4(3) . . ? C5 C6 N1 119.5(3) . . ? O C7 N1 123.8(3) . . ? O C7 C8 130.8(3) . . ? N1 C7 C8 105.4(3) . . ? C9 C8 C7 107.3(3) . . ? C9 C8 C16 126.8(3) . . ? C7 C8 C16 125.5(3) . . ? N2 C9 C8 109.2(3) . . ? N2 C9 C10 118.4(3) . . ? C8 C9 C10 132.3(3) . . ? C11 C10 C15 118.4(3) . . ? C11 C10 C9 120.4(3) . . ? C15 C10 C9 121.0(3) . . ? C12 C11 C10 121.0(4) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C13 C12 C11 118.1(4) . . ? C13 C12 H12 120.9 . . ? C11 C12 H12 120.9 . . ? C12 C13 C14 123.2(4) . . ? C12 C13 F 118.6(4) . . ? C14 C13 F 118.2(4) . . ? C13 C14 C15 118.1(4) . . ? C13 C14 H14 121.0 . . ? C15 C14 H14 121.0 . . ? C14 C15 C10 121.1(4) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.4 . . ? N3 C16 C8 127.0(3) . . ? N3 C16 C17 116.0(3) . . ? C8 C16 C17 117.1(3) . . ? C22 C17 C18 117.4(3) . . ? C22 C17 C16 125.2(3) . . ? C18 C17 C16 117.4(3) . . ? C19 C18 C17 118.6(5) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C18 C19 C20 121.4(5) . . ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 . . ? C21 C20 C19 121.4(4) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C20 C21 C22 119.5(4) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C21 C22 C17 121.6(3) . . ? C21 C22 Cl 117.3(3) . . ? C17 C22 Cl 121.1(3) . . ? N5 C23 N4 117.8(3) . . ? N5 C23 S 124.4(3) . . ? N4 C23 S 117.8(3) . . ? N5 C24 H24A 109.5 . . ? N5 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N5 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 C7 N1 N2 C9 5.1(4) . . . . ? C6 N1 N2 C9 168.9(3) . . . . ? C16 N3 N4 C23 173.0(3) . . . . ? C6 C1 C2 C3 2.0(6) . . . . ? C1 C2 C3 C4 -0.4(7) . . . . ? C2 C3 C4 C5 -1.2(7) . . . . ? C3 C4 C5 C6 1.1(6) . . . . ? C2 C1 C6 C5 -2.1(6) . . . . ? C2 C1 C6 N1 177.5(4) . . . . ? C4 C5 C6 C1 0.6(6) . . . . ? C4 C5 C6 N1 -179.0(4) . . . . ? N2 N1 C6 C1 163.6(3) . . . . ? C7 N1 C6 C1 -35.7(5) . . . . ? N2 N1 C6 C5 -16.8(5) . . . . ? C7 N1 C6 C5 143.8(4) . . . . ? N2 N1 C7 O 173.5(3) . . . . ? C6 N1 C7 O 11.1(6) . . . . ? N2 N1 C7 C8 -4.1(4) . . . . ? C6 N1 C7 C8 -166.6(3) . . . . ? O C7 C8 C9 -175.7(4) . . . . ? N1 C7 C8 C9 1.7(4) . . . . ? O C7 C8 C16 -2.4(6) . . . . ? N1 C7 C8 C16 175.0(3) . . . . ? N1 N2 C9 C8 -3.9(4) . . . . ? N1 N2 C9 C10 178.8(3) . . . . ? C7 C8 C9 N2 1.3(4) . . . . ? C16 C8 C9 N2 -171.9(3) . . . . ? C7 C8 C9 C10 178.1(4) . . . . ? C16 C8 C9 C10 5.0(6) . . . . ? N2 C9 C10 C11 40.9(5) . . . . ? C8 C9 C10 C11 -135.7(4) . . . . ? N2 C9 C10 C15 -143.1(4) . . . . ? C8 C9 C10 C15 40.3(6) . . . . ? C15 C10 C11 C12 -2.0(6) . . . . ? C9 C10 C11 C12 174.2(4) . . . . ? C10 C11 C12 C13 1.0(7) . . . . ? C11 C12 C13 C14 0.3(8) . . . . ? C11 C12 C13 F -178.2(4) . . . . ? C12 C13 C14 C15 -0.6(7) . . . . ? F C13 C14 C15 177.9(4) . . . . ? C13 C14 C15 C10 -0.4(6) . . . . ? C11 C10 C15 C14 1.6(6) . . . . ? C9 C10 C15 C14 -174.4(4) . . . . ? N4 N3 C16 C8 0.5(5) . . . . ? N4 N3 C16 C17 178.4(3) . . . . ? C9 C8 C16 N3 -148.9(4) . . . . ? C7 C8 C16 N3 39.1(6) . . . . ? C9 C8 C16 C17 33.2(5) . . . . ? C7 C8 C16 C17 -138.8(4) . . . . ? N3 C16 C17 C22 43.1(5) . . . . ? C8 C16 C17 C22 -138.8(4) . . . . ? N3 C16 C17 C18 -137.4(3) . . . . ? C8 C16 C17 C18 40.8(5) . . . . ? C22 C17 C18 C19 2.7(6) . . . . ? C16 C17 C18 C19 -176.9(4) . . . . ? C17 C18 C19 C20 -0.6(7) . . . . ? C18 C19 C20 C21 -2.7(9) . . . . ? C19 C20 C21 C22 3.9(9) . . . . ? C20 C21 C22 C17 -1.7(8) . . . . ? C20 C21 C22 Cl 175.8(4) . . . . ? C18 C17 C22 C21 -1.6(6) . . . . ? C16 C17 C22 C21 178.0(4) . . . . ? C18 C17 C22 Cl -179.0(3) . . . . ? C16 C17 C22 Cl 0.6(6) . . . . ? C24 N5 C23 N4 -179.1(4) . . . . ? C24 N5 C23 S -0.5(6) . . . . ? N3 N4 C23 N5 -9.1(5) . . . . ? N3 N4 C23 S 172.2(3) . . . . ? 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 N2 H2N S 0.860(10) 2.386(12) 3.240(3) 172(4) 3_666 N4 H4N O 0.861(10) 1.884(17) 2.695(4) 156(3) . N5 H5N N3 0.855(10) 2.10(4) 2.640(4) 121(4) . N5 H5N O 0.855(10) 2.58(4) 3.033(4) 115(4) 4_576 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.904 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.068