# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author ; 'Jonathan P. Hill' ; _publ_contact_author_email Jonathan.Hill@nims.go.jp _publ_section_title ; Antioxidant-substituted Tetrapyrazinoporphyrinazine as a Turn-on Fluorescent Sensor for Basic Anions ; loop_ _publ_author_name _publ_author_address 'Jonathan P. Hill' ; International Center for Materials Nanoarchitectonics National Institute for Materials Science 1-1 Namiki Tsukuba Ibaraki 305-0044 Japan ; 'Navaneetha K. Subbaiyan' ; Department of Chemistry University of North Texas 1155 Union Circle Denton TX 76203-5017 USA ; 'Francis DfSouza' ; Department of Chemistry University of North Texas 1155 Union Circle Denton TX 76203-5017 USA ; 'Yonshu Xie' ; Key Laboratory for Advanced Materials and Institute of Fine Chemicals East China University of Science and Technology Meilong Rd. 130 Shanghai 200237 P. R. China ; 'Satyajit Sahu' ; Surface Characterization Group, Advanced Key Technologies Division/Nano Characterization Unit National Institute of Materials Science Namiki 1-1 Tsukuba Ibaraki 305-0044 Japan. ; ; N.M.Sanchez-Ballester ; ; International Center for Materials Nanoarchitectonics National Institute for Materials Science 1-1 Namiki Tsukuba Ibaraki 305-0044 Japan ; 'Gary J. Richards' ; Fuel Cell Materials Center National Institute for Materials Science 1-1 Namiki Tsukuba Ibaraki 305-0044 Japan ; 'Toshiyuki Mori' ; Fuel Cell Materials Center National Institute for Materials Science 1-1 Namiki Tsukuba Ibaraki 305-0044 Japan ; 'Katsuhiko Ariga' ; International Center for Materials Nanoarchitectonics National Institute for Materials Science 1-1 Namiki Tsukuba Ibaraki 305-0044 Japan ; data_phth3 _database_code_depnum_ccdc_archive 'CCDC 864529' #TrackingRef '2.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H42 N4 O2' _chemical_formula_weight 538.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P4(3)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 15.9922(12) _cell_length_b 15.9922(12) _cell_length_c 12.4393(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3181.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(3) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.125 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details 'SADABS v2.10, Sheldrick, G.M., (2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25867 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.13 _reflns_number_total 3351 _reflns_number_gt 3113 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART Apex' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0708P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.2(18) _refine_ls_number_reflns 3351 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1360 _refine_ls_wR_factor_gt 0.1294 _refine_ls_goodness_of_fit_ref 1.527 _refine_ls_restrained_S_all 1.527 _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 N2 N 0.36564(8) 0.44539(8) 0.08502(10) 0.0261(3) Uani 1 1 d . . . C3 C 0.33266(9) 0.37629(9) 0.04173(12) 0.0222(3) Uani 1 1 d . . . C9 C 0.18718(9) 0.32195(9) 0.01682(13) 0.0241(3) Uani 1 1 d . . . O1 O 0.01536(8) 0.29595(11) 0.20122(12) 0.0491(4) Uani 1 1 d . . . C4 C 0.25016(9) 0.35143(9) 0.08437(12) 0.0233(3) Uani 1 1 d . . . C2 C 0.43682(10) 0.47477(9) 0.04429(14) 0.0281(3) Uani 1 1 d . . . C8 C 0.10859(9) 0.30224(10) 0.05565(13) 0.0272(3) Uani 1 1 d . . . C5 C 0.23407(10) 0.36048(10) 0.19373(13) 0.0268(3) Uani 1 1 d . . . C6 C 0.15678(10) 0.34065(10) 0.23800(14) 0.0305(4) Uani 1 1 d . . . C15 C 0.07300(12) 0.25651(14) -0.13493(14) 0.0426(5) Uani 1 1 d . . . H15A H 0.0978 0.3069 -0.1623 0.064 Uiso 1 1 calc R . . H15B H 0.0279 0.2397 -0.1810 0.064 Uiso 1 1 calc R . . H15C H 0.1144 0.2131 -0.1325 0.064 Uiso 1 1 calc R . . C14 C 0.03927(10) 0.27241(12) -0.02116(14) 0.0366(4) Uani 1 1 d . . . C7 C 0.09436(9) 0.31311(11) 0.16631(14) 0.0311(4) Uani 1 1 d . . . C10 C 0.14153(12) 0.34832(13) 0.35991(14) 0.0429(5) Uani 1 1 d . . . C13 C 0.11724(16) 0.26441(16) 0.40819(17) 0.0550(6) Uani 1 1 d . . . H13A H 0.1077 0.2709 0.4839 0.083 Uiso 1 1 calc R . . H13B H 0.1616 0.2249 0.3968 0.083 Uiso 1 1 calc R . . H13C H 0.0671 0.2444 0.3743 0.083 Uiso 1 1 calc R . . N1 N 0.50111(14) 0.60611(12) 0.13182(19) 0.0649(6) Uani 1 1 d . . . C1 C 0.47225(12) 0.54852(11) 0.09401(15) 0.0396(4) Uani 1 1 d . . . C11 C 0.22162(17) 0.3748(2) 0.41784(17) 0.0772(10) Uani 1 1 d . . . H11A H 0.2396 0.4281 0.3910 0.116 Uiso 1 1 calc R . . H11B H 0.2645 0.3340 0.4053 0.116 Uiso 1 1 calc R . . H11C H 0.2110 0.3790 0.4936 0.116 Uiso 1 1 calc R . . C17 C 0.00092(17) 0.18977(17) 0.0178(2) 0.0648(7) Uani 1 1 d . . . H17A H -0.0419 0.1723 -0.0314 0.097 Uiso 1 1 calc R . . H17B H -0.0230 0.1976 0.0879 0.097 Uiso 1 1 calc R . . H17C H 0.0437 0.1477 0.0214 0.097 Uiso 1 1 calc R . . C16 C -0.02833(14) 0.34041(18) -0.0284(2) 0.0660(7) Uani 1 1 d . . . H16A H -0.0037 0.3916 -0.0534 0.099 Uiso 1 1 calc R . . H16B H -0.0525 0.3492 0.0414 0.099 Uiso 1 1 calc R . . H16C H -0.0711 0.3230 -0.0777 0.099 Uiso 1 1 calc R . . C12 C 0.0744(2) 0.41493(18) 0.3844(2) 0.0788(9) Uani 1 1 d . . . H12A H 0.0909 0.4674 0.3534 0.118 Uiso 1 1 calc R . . H12B H 0.0687 0.4211 0.4608 0.118 Uiso 1 1 calc R . . H12C H 0.0219 0.3977 0.3542 0.118 Uiso 1 1 calc R . . H2 H 0.1984(11) 0.3204(10) -0.0570(15) 0.021(4) Uiso 1 1 d . . . H3 H 0.2756(11) 0.3815(10) 0.2345(14) 0.024(4) Uiso 1 1 d . . . H1 H 0.011(2) 0.315(2) 0.267(3) 0.096(11) 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 N2 0.0242(6) 0.0217(6) 0.0324(7) -0.0010(5) -0.0014(5) -0.0013(5) C3 0.0220(7) 0.0199(7) 0.0246(7) 0.0021(6) -0.0031(6) 0.0013(5) C9 0.0250(8) 0.0222(7) 0.0250(8) 0.0012(6) 0.0008(6) 0.0003(6) O1 0.0282(7) 0.0829(11) 0.0362(7) 0.0009(7) 0.0066(6) -0.0147(6) C4 0.0223(7) 0.0189(7) 0.0285(8) -0.0001(6) 0.0007(6) -0.0003(5) C2 0.0265(8) 0.0221(7) 0.0358(8) 0.0020(6) -0.0039(7) -0.0022(6) C8 0.0221(8) 0.0265(8) 0.0329(8) 0.0018(7) -0.0035(6) -0.0009(6) C5 0.0273(8) 0.0252(8) 0.0280(8) -0.0010(6) -0.0011(6) -0.0050(6) C6 0.0342(9) 0.0294(8) 0.0280(8) -0.0021(6) 0.0049(7) -0.0049(6) C15 0.0338(9) 0.0595(12) 0.0346(9) -0.0043(9) -0.0060(8) -0.0122(8) C14 0.0236(8) 0.0528(11) 0.0335(9) 0.0007(8) -0.0036(7) -0.0079(7) C7 0.0233(8) 0.0350(9) 0.0350(9) 0.0027(7) 0.0044(6) -0.0034(6) C10 0.0473(10) 0.0525(11) 0.0289(9) -0.0074(8) 0.0094(8) -0.0175(9) C13 0.0623(14) 0.0670(14) 0.0358(10) 0.0096(10) -0.0038(10) -0.0241(12) N1 0.0715(14) 0.0465(11) 0.0768(14) -0.0149(10) 0.0003(11) -0.0303(9) C1 0.0391(10) 0.0328(9) 0.0470(11) -0.0028(8) 0.0034(8) -0.0102(7) C11 0.0781(18) 0.123(2) 0.0307(10) -0.0230(13) 0.0113(11) -0.0604(17) C17 0.0640(15) 0.0776(17) 0.0530(13) -0.0017(12) -0.0001(11) -0.0460(12) C16 0.0363(11) 0.104(2) 0.0575(14) -0.0109(13) -0.0137(10) 0.0227(12) C12 0.112(2) 0.0723(17) 0.0522(14) -0.0067(13) 0.0432(15) 0.0112(16) _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 N2 C2 1.332(2) . ? N2 C3 1.3377(19) . ? C3 C3 1.432(3) 7 ? C3 C4 1.477(2) . ? C9 C8 1.383(2) . ? C9 C4 1.394(2) . ? O1 C7 1.364(2) . ? C4 C5 1.392(2) . ? C2 C2 1.397(3) 7 ? C2 C1 1.447(2) . ? C8 C7 1.406(2) . ? C8 C14 1.539(2) . ? C5 C6 1.390(2) . ? C6 C7 1.409(2) . ? C6 C10 1.541(2) . ? C15 C14 1.536(2) . ? C14 C16 1.536(3) . ? C14 C17 1.536(3) . ? C10 C13 1.521(3) . ? C10 C11 1.530(3) . ? C10 C12 1.542(3) . ? N1 C1 1.133(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 N2 C3 118.38(13) . . ? N2 C3 C3 120.15(8) . 7 ? N2 C3 C4 115.47(13) . . ? C3 C3 C4 124.37(8) 7 . ? C8 C9 C4 121.55(15) . . ? C5 C4 C9 119.39(14) . . ? C5 C4 C3 119.22(14) . . ? C9 C4 C3 121.35(14) . . ? N2 C2 C2 121.22(9) . 7 ? N2 C2 C1 117.37(15) . . ? C2 C2 C1 121.40(10) 7 . ? C9 C8 C7 117.44(14) . . ? C9 C8 C14 120.56(14) . . ? C7 C8 C14 121.97(14) . . ? C6 C5 C4 121.86(15) . . ? C5 C6 C7 116.78(15) . . ? C5 C6 C10 120.84(15) . . ? C7 C6 C10 122.39(15) . . ? C16 C14 C17 110.29(19) . . ? C16 C14 C15 108.09(17) . . ? C17 C14 C15 106.79(17) . . ? C16 C14 C8 108.90(16) . . ? C17 C14 C8 110.99(16) . . ? C15 C14 C8 111.73(14) . . ? O1 C7 C8 115.89(15) . . ? O1 C7 C6 121.17(16) . . ? C8 C7 C6 122.93(14) . . ? C13 C10 C11 105.8(2) . . ? C13 C10 C12 110.72(19) . . ? C11 C10 C12 107.4(2) . . ? C13 C10 C6 111.03(16) . . ? C11 C10 C6 110.69(15) . . ? C12 C10 C6 111.06(18) . . ? N1 C1 C2 178.9(2) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.13 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.217 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.047 data_jh1 _database_code_depnum_ccdc_archive 'CCDC 864530' #TrackingRef '3.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 Cl N4 O' _chemical_formula_weight 368.86 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 P2(1)/m(11) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 10.639(5) _cell_length_b 6.969(3) _cell_length_c 13.260(6) _cell_angle_alpha 90.00 _cell_angle_beta 109.394(7) _cell_angle_gamma 90.00 _cell_volume 927.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2327 _cell_measurement_theta_min 3.22 _cell_measurement_theta_max 26.16 _exptl_crystal_description neddle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details 'SADABS v2.10, Sheldrick, G.M., (2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7235 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.04 _reflns_number_total 2040 _reflns_number_gt 1574 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0598P)^2^+0.6163P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'except OH' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2040 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.5396(2) 0.2500 0.70498(17) 0.0320(6) Uani 1 2 d S . . C1 C 0.4423(3) 0.2500 0.6126(2) 0.0316(6) Uani 1 2 d S . . Cl1 Cl 0.28633(8) 0.2500 0.62593(6) 0.0744(4) Uani 1 2 d S . . C2 C 0.4625(2) 0.2500 0.5114(2) 0.0245(6) Uani 1 2 d S . . N2 N 0.5898(2) 0.2500 0.51432(17) 0.0292(5) Uani 1 2 d S . . C3 C 0.6890(3) 0.2500 0.6075(2) 0.0278(6) Uani 1 2 d S . . C4 C 0.6647(2) 0.2500 0.7039(2) 0.0262(6) Uani 1 2 d S . . C5 C 0.7727(3) 0.2500 0.8059(2) 0.0302(6) Uani 1 2 d S . . N3 N 0.8582(2) 0.2500 0.88505(18) 0.0377(6) Uani 1 2 d S . . C6 C 0.8220(3) 0.2500 0.6005(2) 0.0343(7) Uani 1 2 d S . . N4 N 0.9269(3) 0.2500 0.5950(2) 0.0456(7) Uani 1 2 d S . . C7 C 0.3637(2) 0.2500 0.4020(2) 0.0244(6) Uani 1 2 d S . . C8 C 0.2251(3) 0.2500 0.3758(2) 0.0269(6) Uani 1 2 d S . . H8 H 0.1891 0.2500 0.4308 0.032 Uiso 1 2 calc SR . . C9 C 0.1390(2) 0.2500 0.2709(2) 0.0262(6) Uani 1 2 d S . . C10 C 0.1960(3) 0.2500 0.1884(2) 0.0274(6) Uani 1 2 d S . . O1 O 0.12235(18) 0.2500 0.08337(15) 0.0358(5) Uani 1 2 d SD . . H1 H 0.043(2) 0.2500 0.078(3) 0.054 Uiso 1 2 d SD . . C11 C 0.3363(2) 0.2500 0.2110(2) 0.0247(6) Uani 1 2 d S . . C12 C 0.4152(2) 0.2500 0.3172(2) 0.0249(6) Uani 1 2 d S . . H12 H 0.5072 0.2500 0.3336 0.030 Uiso 1 2 calc SR . . C13 C -0.0143(2) 0.2500 0.2463(2) 0.0310(7) Uani 1 2 d S . . C14 C -0.0498(3) 0.2500 0.3497(2) 0.0370(7) Uani 1 2 d S . . H14A H -0.1449 0.2500 0.3321 0.055 Uiso 1 2 calc SR . . H14B H -0.0133 0.3625 0.3908 0.055 Uiso 0.50 1 calc PR . . H14C H -0.0133 0.1375 0.3908 0.055 Uiso 0.50 1 calc PR . . C15 C -0.07708(18) 0.0682(4) 0.18427(16) 0.0394(5) Uani 1 1 d . . . H15A H -0.1716 0.0701 0.1702 0.059 Uiso 1 1 calc R . . H15B H -0.0394 -0.0431 0.2260 0.059 Uiso 1 1 calc R . . H15C H -0.0594 0.0640 0.1179 0.059 Uiso 1 1 calc R . . C16 C 0.3993(2) 0.2500 0.1219(2) 0.0287(6) Uani 1 2 d S . . C17 C 0.3583(2) 0.0691(4) 0.05272(16) 0.0421(6) Uani 1 1 d . . . H17A H 0.3911 0.0770 -0.0064 0.063 Uiso 1 1 calc R . . H17B H 0.2629 0.0591 0.0263 0.063 Uiso 1 1 calc R . . H17C H 0.3953 -0.0420 0.0950 0.063 Uiso 1 1 calc R . . C18 C 0.5522(3) 0.2500 0.1673(2) 0.0343(7) Uani 1 2 d S . . H18A H 0.5822 0.3613 0.2114 0.052 Uiso 0.50 1 calc PR . . H18B H 0.5877 0.2523 0.1096 0.052 Uiso 1 2 calc SR . . H18C H 0.5823 0.1364 0.2094 0.052 Uiso 0.50 1 calc PR . . 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 0.0247(12) 0.0451(15) 0.0222(11) 0.000 0.0025(9) 0.000 C1 0.0213(13) 0.0460(18) 0.0242(13) 0.000 0.0032(11) 0.000 Cl1 0.0233(4) 0.1727(13) 0.0259(4) 0.000 0.0064(3) 0.000 C2 0.0212(13) 0.0251(14) 0.0246(13) 0.000 0.0043(10) 0.000 N2 0.0214(11) 0.0389(14) 0.0241(11) 0.000 0.0033(9) 0.000 C3 0.0217(13) 0.0313(15) 0.0255(13) 0.000 0.0009(10) 0.000 C4 0.0222(13) 0.0296(15) 0.0218(13) 0.000 0.0006(10) 0.000 C5 0.0241(14) 0.0395(17) 0.0245(14) 0.000 0.0046(12) 0.000 N3 0.0287(13) 0.0511(17) 0.0275(13) 0.000 0.0015(11) 0.000 C6 0.0249(15) 0.0530(19) 0.0193(13) 0.000 -0.0004(11) 0.000 N4 0.0289(14) 0.073(2) 0.0331(14) 0.000 0.0074(11) 0.000 C7 0.0211(13) 0.0262(14) 0.0219(13) 0.000 0.0020(10) 0.000 C8 0.0217(13) 0.0349(16) 0.0233(13) 0.000 0.0065(10) 0.000 C9 0.0196(13) 0.0336(15) 0.0243(13) 0.000 0.0058(10) 0.000 C10 0.0202(13) 0.0364(16) 0.0220(13) 0.000 0.0023(10) 0.000 O1 0.0154(9) 0.0690(15) 0.0200(9) 0.000 0.0016(8) 0.000 C11 0.0197(13) 0.0297(14) 0.0235(13) 0.000 0.0056(10) 0.000 C12 0.0163(12) 0.0299(15) 0.0258(13) 0.000 0.0031(10) 0.000 C13 0.0171(13) 0.0508(19) 0.0232(13) 0.000 0.0043(10) 0.000 C14 0.0210(14) 0.060(2) 0.0311(15) 0.000 0.0098(12) 0.000 C15 0.0225(10) 0.0613(15) 0.0320(11) -0.0042(10) 0.0059(8) -0.0056(10) C16 0.0168(12) 0.0448(17) 0.0238(13) 0.000 0.0057(10) 0.000 C17 0.0290(10) 0.0662(16) 0.0338(11) -0.0151(11) 0.0139(8) -0.0084(11) C18 0.0212(13) 0.0517(19) 0.0300(14) 0.000 0.0084(11) 0.000 _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 C1 1.315(3) . ? N1 C4 1.336(3) . ? C1 C2 1.427(4) . ? C1 Cl1 1.727(3) . ? C2 N2 1.342(3) . ? C2 C7 1.482(3) . ? N2 C3 1.332(3) . ? C3 C4 1.385(4) . ? C3 C6 1.449(4) . ? C4 C5 1.455(4) . ? C5 N3 1.138(3) . ? C6 N4 1.142(4) . ? C7 C8 1.398(4) . ? C7 C12 1.405(4) . ? C8 C9 1.389(4) . ? C9 C10 1.415(4) . ? C9 C13 1.554(4) . ? C10 O1 1.353(3) . ? C10 C11 1.422(4) . ? C11 C12 1.379(4) . ? C11 C16 1.540(4) . ? C13 C15 1.537(3) 4_565 ? C13 C15 1.537(3) . ? C13 C14 1.538(4) . ? C16 C17 1.535(3) . ? C16 C17 1.535(3) 4_565 ? C16 C18 1.536(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 117.9(2) . . ? N1 C1 C2 124.0(2) . . ? N1 C1 Cl1 113.0(2) . . ? C2 C1 Cl1 123.1(2) . . ? N2 C2 C1 116.0(2) . . ? N2 C2 C7 114.1(2) . . ? C1 C2 C7 129.9(2) . . ? C3 N2 C2 120.5(2) . . ? N2 C3 C4 121.5(2) . . ? N2 C3 C6 115.5(2) . . ? C4 C3 C6 123.0(2) . . ? N1 C4 C3 120.1(2) . . ? N1 C4 C5 118.2(2) . . ? C3 C4 C5 121.7(2) . . ? N3 C5 C4 179.2(3) . . ? N4 C6 C3 180.0(3) . . ? C8 C7 C12 117.4(2) . . ? C8 C7 C2 126.2(2) . . ? C12 C7 C2 116.4(2) . . ? C9 C8 C7 122.6(2) . . ? C8 C9 C10 117.7(2) . . ? C8 C9 C13 120.4(2) . . ? C10 C9 C13 121.8(2) . . ? O1 C10 C9 123.1(2) . . ? O1 C10 C11 115.2(2) . . ? C9 C10 C11 121.7(2) . . ? C12 C11 C10 117.1(2) . . ? C12 C11 C16 120.8(2) . . ? C10 C11 C16 122.1(2) . . ? C11 C12 C7 123.4(2) . . ? C15 C13 C15 111.0(2) 4_565 . ? C15 C13 C14 106.60(15) 4_565 . ? C15 C13 C14 106.60(15) . . ? C15 C13 C9 110.55(14) 4_565 . ? C15 C13 C9 110.55(14) . . ? C14 C13 C9 111.4(2) . . ? C17 C16 C17 110.5(2) . 4_565 ? C17 C16 C18 106.74(15) . . ? C17 C16 C18 106.75(15) 4_565 . ? C17 C16 C11 110.44(14) . . ? C17 C16 C11 110.44(14) 4_565 . ? C18 C16 C11 111.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 0.000(1) . . . . ? C4 N1 C1 Cl1 180.0 . . . . ? N1 C1 C2 N2 0.000(1) . . . . ? Cl1 C1 C2 N2 180.0 . . . . ? N1 C1 C2 C7 180.0 . . . . ? Cl1 C1 C2 C7 0.000(1) . . . . ? C1 C2 N2 C3 0.0 . . . . ? C7 C2 N2 C3 180.0 . . . . ? C2 N2 C3 C4 0.000(1) . . . . ? C2 N2 C3 C6 180.0 . . . . ? C1 N1 C4 C3 0.000(1) . . . . ? C1 N1 C4 C5 180.0 . . . . ? N2 C3 C4 N1 0.000(1) . . . . ? C6 C3 C4 N1 180.0 . . . . ? N2 C3 C4 C5 180.000(1) . . . . ? C6 C3 C4 C5 0.000(1) . . . . ? N1 C4 C5 N3 180.00(8) . . . . ? C3 C4 C5 N3 0.00(8) . . . . ? N2 C3 C6 N4 180(100) . . . . ? C4 C3 C6 N4 0(100) . . . . ? N2 C2 C7 C8 180.0 . . . . ? C1 C2 C7 C8 0.0 . . . . ? N2 C2 C7 C12 0.0 . . . . ? C1 C2 C7 C12 180.0 . . . . ? C12 C7 C8 C9 0.0 . . . . ? C2 C7 C8 C9 180.0 . . . . ? C7 C8 C9 C10 0.0 . . . . ? C7 C8 C9 C13 180.0 . . . . ? C8 C9 C10 O1 180.0 . . . . ? C13 C9 C10 O1 0.0 . . . . ? C8 C9 C10 C11 0.0 . . . . ? C13 C9 C10 C11 180.0 . . . . ? O1 C10 C11 C12 180.0 . . . . ? C9 C10 C11 C12 0.0 . . . . ? O1 C10 C11 C16 0.0 . . . . ? C9 C10 C11 C16 180.0 . . . . ? C10 C11 C12 C7 0.0 . . . . ? C16 C11 C12 C7 180.0 . . . . ? C8 C7 C12 C11 0.0 . . . . ? C2 C7 C12 C11 180.0 . . . . ? C8 C9 C13 C15 118.33(15) . . . 4_565 ? C10 C9 C13 C15 -61.67(15) . . . 4_565 ? C8 C9 C13 C15 -118.33(15) . . . . ? C10 C9 C13 C15 61.67(15) . . . . ? C8 C9 C13 C14 0.0 . . . . ? C10 C9 C13 C14 180.0 . . . . ? C12 C11 C16 C17 118.76(16) . . . . ? C10 C11 C16 C17 -61.24(16) . . . . ? C12 C11 C16 C17 -118.76(16) . . . 4_565 ? C10 C11 C16 C17 61.24(16) . . . 4_565 ? C12 C11 C16 C18 0.0 . . . . ? C10 C11 C16 C18 180.0 . . . . ? 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 O1 H1 N3 0.825(18) 2.66(3) 3.147(3) 119(3) 1_454 _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 27.04 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.545 _refine_diff_density_min -0.613 _refine_diff_density_rms 0.054