data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'G Sanjayan' _publ_contact_author_email GJ.SANJAYAN@NCL.RES.IN _publ_section_title ; Sterically Controlled Naphthalene Homo-Oligoamides with Novel Structural Architectures ; loop_ _publ_author_name 'G Sanjayan' 'Jima N. Chandran' 'Hans-J\"org Hofmann' 'Panchami Prabhakaran' ; V.G.Puranik ; 'P. R. Rajamohanan' # Attachment '3a.cif' ##Title:Sterically Controlled Naphthalene Homo-Oligoamides with Interesting ##Structural Architectures ##Communicated to OBC ##By Panchami Prabhakaran, Vedavati G. Puranik, ##P.R.Rajamohanan, Hans-J\"org Hofmann and Gangadhar J. Sanjayan ##Division of Organic Chemistry,Central NMR Facility, Centre For Materials ##Characterization, National Chemical Laboratory Pune 411 008, India.and ##Universit\"at Leipzig, Fakult\"at f\"ur Biowissenschaften, Pharmazie und Psychologie, ##Institut f\"ur Biochemie, Br\"uderstra\&se 34, D-04103 Leipzig (Germany) data_C25H20N2O7compound3a _database_code_depnum_ccdc_archive 'CCDC 691283' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'aromatic amide' _chemical_melting_point ? _chemical_formula_moiety 'C25 H20 N2 O7' _chemical_formula_sum 'C25 H20 N2 O7' _chemical_formula_weight 460.43 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 Orthorhombic _symmetry_space_group_name_H-M Pna21 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' _cell_length_a 27.786(2) _cell_length_b 4.5194(8) _cell_length_c 17.0553(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2141.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2240 _cell_measurement_theta_min 2.388 _cell_measurement_theta_max 20.05 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9804 _exptl_absorpt_correction_T_max 0.9990 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16929 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3772 _reflns_number_gt 2919 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _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 'SHELXTL and PLATON' _computing_publication_material SHELXTL _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^)+(0.0449P)^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 riding _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 -0.1(9) _refine_ls_number_reflns 3772 _refine_ls_number_parameters 310 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0780 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 O1 O 0.19298(6) -0.3503(4) 0.42956(11) 0.0667(5) Uani 1 1 d . . . O2 O 0.27006(6) -0.4372(4) 0.45033(12) 0.0737(5) Uani 1 1 d . . . O3 O 0.33469(5) -0.1079(3) 0.36186(8) 0.0461(4) Uani 1 1 d . . . O4 O 0.37770(5) -0.0492(4) 0.19399(9) 0.0543(4) Uani 1 1 d . . . O5 O 0.44626(5) 0.3002(3) 0.09077(8) 0.0466(4) Uani 1 1 d . . . O6 O 0.52254(8) 0.7316(6) 0.05457(14) 0.1028(8) Uani 1 1 d . . . O7 O 0.57040(7) 0.4164(6) 0.10177(14) 0.1089(8) Uani 1 1 d . . . N1 N 0.34534(5) 0.3423(4) 0.25717(10) 0.0403(4) Uani 1 1 d . . . H1 H 0.3502 0.5223 0.2715 0.048 Uiso 1 1 calc R . . N2 N 0.53423(7) 0.5610(5) 0.10493(13) 0.0589(5) Uani 1 1 d . . . C1 C 0.18199(10) -0.5503(7) 0.49236(18) 0.0770(9) Uani 1 1 d . . . H1A H 0.1972 -0.7375 0.4827 0.116 Uiso 1 1 calc R . . H1B H 0.1478 -0.5773 0.4955 0.116 Uiso 1 1 calc R . . H1C H 0.1936 -0.4699 0.5409 0.116 Uiso 1 1 calc R . . C2 C 0.23963(8) -0.3116(5) 0.41379(13) 0.0471(6) Uani 1 1 d . . . C3 C 0.24696(7) -0.0989(5) 0.34896(12) 0.0388(5) Uani 1 1 d . . . C4 C 0.20805(7) 0.0043(5) 0.30689(12) 0.0398(5) Uani 1 1 d . . . H4 H 0.1775 -0.0633 0.3199 0.048 Uiso 1 1 calc R . . C5 C 0.21288(7) 0.2071(5) 0.24524(12) 0.0380(5) Uani 1 1 d . . . C6 C 0.17289(8) 0.3017(5) 0.20056(13) 0.0472(6) Uani 1 1 d . . . H6 H 0.1426 0.2242 0.2113 0.057 Uiso 1 1 calc R . . C7 C 0.17804(8) 0.5037(6) 0.14233(13) 0.0520(6) Uani 1 1 d . . . H7 H 0.1513 0.5656 0.1139 0.062 Uiso 1 1 calc R . . C8 C 0.22386(8) 0.6195(5) 0.12496(14) 0.0536(6) Uani 1 1 d . . . H8 H 0.2271 0.7588 0.0852 0.064 Uiso 1 1 calc R . . C9 C 0.26324(7) 0.5313(5) 0.16527(13) 0.0431(5) Uani 1 1 d . . . H9 H 0.2933 0.6090 0.1527 0.052 Uiso 1 1 calc R . . C10 C 0.25904(7) 0.3205(5) 0.22675(12) 0.0379(5) Uani 1 1 d . . . C11 C 0.29872(7) 0.2184(5) 0.27053(12) 0.0372(5) Uani 1 1 d . . . C12 C 0.29358(7) 0.0077(5) 0.32804(13) 0.0391(5) Uani 1 1 d . . . C13 C 0.34965(9) 0.0182(7) 0.43427(16) 0.0705(7) Uani 1 1 d . . . H13A H 0.3511 0.2296 0.4292 0.106 Uiso 1 1 calc R . . H13B H 0.3809 -0.0562 0.4478 0.106 Uiso 1 1 calc R . . H13C H 0.3271 -0.0335 0.4746 0.106 Uiso 1 1 calc R . . C14 C 0.38228(7) 0.1954(5) 0.22356(12) 0.0373(5) Uani 1 1 d . . . C15 C 0.42920(7) 0.3530(5) 0.22943(13) 0.0396(5) Uani 1 1 d . . . C16 C 0.44355(7) 0.4617(5) 0.30122(14) 0.0447(5) Uani 1 1 d . . . H16 H 0.4237 0.4329 0.3444 0.054 Uiso 1 1 calc R . . C17 C 0.48751(7) 0.6158(5) 0.31158(13) 0.0458(6) Uani 1 1 d . . . C18 C 0.50029(9) 0.7446(6) 0.38353(14) 0.0587(7) Uani 1 1 d . . . H18 H 0.4799 0.7248 0.4265 0.070 Uiso 1 1 calc R . . C19 C 0.54203(9) 0.8978(6) 0.39113(17) 0.0690(7) Uani 1 1 d . . . H19 H 0.5499 0.9839 0.4390 0.083 Uiso 1 1 calc R . . C20 C 0.57306(9) 0.9265(7) 0.32783(17) 0.0693(8) Uani 1 1 d . . . H20 H 0.6016 1.0316 0.3338 0.083 Uiso 1 1 calc R . . C21 C 0.56245(8) 0.8040(6) 0.25739(16) 0.0620(7) Uani 1 1 d . . . H21 H 0.5839 0.8240 0.2158 0.074 Uiso 1 1 calc R . . C22 C 0.51889(7) 0.6454(5) 0.24668(13) 0.0449(5) Uani 1 1 d . . . C23 C 0.50307(7) 0.5281(5) 0.17419(13) 0.0436(5) Uani 1 1 d . . . C24 C 0.45980(7) 0.3927(5) 0.16453(13) 0.0390(5) Uani 1 1 d . . . C25 C 0.41110(8) 0.4917(6) 0.05617(14) 0.0585(6) Uani 1 1 d . . . H25A H 0.3809 0.4669 0.0826 0.088 Uiso 1 1 calc R . . H25B H 0.4074 0.4429 0.0017 0.088 Uiso 1 1 calc R . . H25C H 0.4215 0.6934 0.0610 0.088 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0480(10) 0.0719(12) 0.0802(12) 0.0361(11) 0.0156(9) 0.0002(8) O2 0.0583(11) 0.0816(14) 0.0813(13) 0.0375(12) 0.0030(9) 0.0090(10) O3 0.0412(8) 0.0519(10) 0.0452(9) -0.0022(8) -0.0030(7) 0.0099(7) O4 0.0526(9) 0.0406(10) 0.0698(11) -0.0112(8) 0.0156(8) -0.0038(7) O5 0.0446(8) 0.0479(9) 0.0472(9) -0.0056(8) 0.0016(7) 0.0038(7) O6 0.1004(16) 0.128(2) 0.0799(14) 0.0408(15) 0.0312(12) 0.0110(14) O7 0.0605(13) 0.163(2) 0.1031(17) 0.0121(16) 0.0293(12) 0.0364(14) N1 0.0320(9) 0.0301(9) 0.0588(11) -0.0066(9) 0.0055(8) -0.0039(7) N2 0.0402(12) 0.0790(16) 0.0574(14) 0.0051(12) 0.0070(10) -0.0055(10) C1 0.0707(17) 0.079(2) 0.0815(19) 0.0372(16) 0.0231(15) 0.0057(15) C2 0.0491(15) 0.0397(14) 0.0525(15) -0.0025(12) 0.0084(12) 0.0059(11) C3 0.0382(12) 0.0362(13) 0.0419(12) -0.0028(10) 0.0050(9) 0.0023(9) C4 0.0338(11) 0.0395(13) 0.0461(13) -0.0037(11) 0.0061(10) -0.0037(10) C5 0.0367(11) 0.0403(13) 0.0372(12) -0.0058(11) 0.0023(9) 0.0000(9) C6 0.0374(13) 0.0553(15) 0.0488(13) -0.0016(12) 0.0033(10) -0.0001(10) C7 0.0451(13) 0.0692(17) 0.0418(13) 0.0051(12) -0.0013(10) 0.0076(11) C8 0.0592(16) 0.0598(16) 0.0417(13) 0.0057(12) 0.0035(12) 0.0067(12) C9 0.0415(12) 0.0427(13) 0.0450(13) 0.0009(12) 0.0098(11) -0.0020(10) C10 0.0392(12) 0.0352(12) 0.0392(12) -0.0076(10) 0.0038(9) 0.0002(9) C11 0.0340(11) 0.0364(13) 0.0411(11) -0.0070(11) 0.0039(9) -0.0011(9) C12 0.0358(12) 0.0386(13) 0.0430(13) -0.0068(11) -0.0004(10) 0.0036(10) C13 0.0615(15) 0.0879(19) 0.0623(17) -0.0117(15) -0.0143(13) 0.0145(15) C14 0.0366(12) 0.0317(13) 0.0436(12) 0.0024(11) 0.0020(9) 0.0020(9) C15 0.0350(11) 0.0358(12) 0.0479(14) 0.0062(11) 0.0009(10) 0.0047(9) C16 0.0377(11) 0.0530(15) 0.0433(13) 0.0066(11) -0.0005(10) -0.0002(10) C17 0.0409(12) 0.0514(14) 0.0451(13) 0.0081(11) -0.0078(10) 0.0001(10) C18 0.0560(16) 0.0748(19) 0.0452(14) 0.0044(13) -0.0075(12) -0.0035(13) C19 0.0705(18) 0.0754(19) 0.0613(16) 0.0008(15) -0.0274(14) -0.0093(15) C20 0.0536(16) 0.088(2) 0.0664(18) 0.0066(16) -0.0137(14) -0.0191(14) C21 0.0437(13) 0.0805(19) 0.0618(18) 0.0042(15) -0.0053(12) -0.0116(13) C22 0.0347(11) 0.0500(13) 0.0500(14) 0.0071(12) -0.0060(11) 0.0030(10) C23 0.0330(11) 0.0518(13) 0.0459(13) 0.0072(12) 0.0032(10) 0.0011(10) C24 0.0358(12) 0.0405(12) 0.0409(13) 0.0015(11) 0.0026(10) 0.0065(9) C25 0.0577(14) 0.0697(17) 0.0482(14) -0.0019(13) -0.0067(12) 0.0079(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.335(3) . ? O1 C1 1.434(3) . ? O2 C2 1.194(3) . ? O3 C12 1.382(3) . ? O3 C13 1.422(3) . ? O4 C14 1.222(2) . ? O5 C24 1.378(3) . ? O5 C25 1.432(3) . ? O6 N2 1.199(3) . ? O7 N2 1.200(3) . ? N1 C14 1.350(3) . ? N1 C11 1.429(2) . ? N1 H1 0.8600 . ? N2 C23 1.472(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.479(3) . ? C3 C4 1.379(3) . ? C3 C12 1.427(3) . ? C4 C5 1.401(3) . ? C4 H4 0.9300 . ? C5 C6 1.414(3) . ? C5 C10 1.417(3) . ? C6 C7 1.357(3) . ? C6 H6 0.9300 . ? C7 C8 1.408(3) . ? C7 H7 0.9300 . ? C8 C9 1.353(3) . ? C8 H8 0.9300 . ? C9 C10 1.421(3) . ? C9 H9 0.9300 . ? C10 C11 1.409(3) . ? C11 C12 1.375(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.489(3) . ? C15 C16 1.378(3) . ? C15 C24 1.407(3) . ? C16 C17 1.417(3) . ? C16 H16 0.9300 . ? C17 C18 1.404(3) . ? C17 C22 1.415(3) . ? C18 C19 1.357(3) . ? C18 H18 0.9300 . ? C19 C20 1.388(4) . ? C19 H19 0.9300 . ? C20 C21 1.355(4) . ? C20 H20 0.9300 . ? C21 C22 1.419(3) . ? C21 H21 0.9300 . ? C22 C23 1.415(3) . ? C23 C24 1.359(3) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 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 C2 O1 C1 116.10(19) . . ? C12 O3 C13 116.89(16) . . ? C24 O5 C25 112.27(16) . . ? C14 N1 C11 124.33(17) . . ? C14 N1 H1 117.8 . . ? C11 N1 H1 117.8 . . ? O6 N2 O7 123.0(2) . . ? O6 N2 C23 118.7(2) . . ? O7 N2 C23 118.3(2) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O1 121.3(2) . . ? O2 C2 C3 127.0(2) . . ? O1 C2 C3 111.7(2) . . ? C4 C3 C12 117.9(2) . . ? C4 C3 C2 120.05(19) . . ? C12 C3 C2 122.08(19) . . ? C3 C4 C5 122.45(18) . . ? C3 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C4 C5 C6 121.81(19) . . ? C4 C5 C10 119.37(18) . . ? C6 C5 C10 118.82(19) . . ? C7 C6 C5 121.0(2) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 120.0(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 121.0(2) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 120.4(2) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C5 118.15(19) . . ? C11 C10 C9 123.09(19) . . ? C5 C10 C9 118.76(18) . . ? C12 C11 C10 121.58(19) . . ? C12 C11 N1 118.63(19) . . ? C10 C11 N1 119.8(2) . . ? C11 C12 O3 118.29(18) . . ? C11 C12 C3 120.42(19) . . ? O3 C12 C3 121.21(19) . . ? O3 C13 H13A 109.5 . . ? O3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O4 C14 N1 122.75(18) . . ? O4 C14 C15 123.49(18) . . ? N1 C14 C15 113.71(18) . . ? C16 C15 C24 118.59(19) . . ? C16 C15 C14 118.92(19) . . ? C24 C15 C14 122.5(2) . . ? C15 C16 C17 122.4(2) . . ? C15 C16 H16 118.8 . . ? C17 C16 H16 118.8 . . ? C18 C17 C22 119.3(2) . . ? C18 C17 C16 122.1(2) . . ? C22 C17 C16 118.7(2) . . ? C19 C18 C17 120.7(2) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 120.3(3) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C21 C20 C19 121.1(2) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 120.4(2) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C17 C22 C23 117.16(18) . . ? C17 C22 C21 118.2(2) . . ? C23 C22 C21 124.5(2) . . ? C24 C23 C22 123.3(2) . . ? C24 C23 N2 117.9(2) . . ? C22 C23 N2 118.72(17) . . ? C23 C24 O5 119.26(19) . . ? C23 C24 C15 119.8(2) . . ? O5 C24 C15 120.96(18) . . ? O5 C25 H25A 109.5 . . ? O5 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O5 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 C1 O1 C2 O2 -0.1(3) . . . . ? C1 O1 C2 C3 -179.3(2) . . . . ? O2 C2 C3 C4 173.1(2) . . . . ? O1 C2 C3 C4 -7.8(3) . . . . ? O2 C2 C3 C12 -7.3(4) . . . . ? O1 C2 C3 C12 171.81(19) . . . . ? C12 C3 C4 C5 0.0(3) . . . . ? C2 C3 C4 C5 179.62(19) . . . . ? C3 C4 C5 C6 177.4(2) . . . . ? C3 C4 C5 C10 -2.4(3) . . . . ? C4 C5 C6 C7 178.4(2) . . . . ? C10 C5 C6 C7 -1.8(3) . . . . ? C5 C6 C7 C8 0.8(3) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C7 C8 C9 C10 -0.5(3) . . . . ? C4 C5 C10 C11 1.4(3) . . . . ? C6 C5 C10 C11 -178.43(19) . . . . ? C4 C5 C10 C9 -178.55(19) . . . . ? C6 C5 C10 C9 1.6(3) . . . . ? C8 C9 C10 C11 179.6(2) . . . . ? C8 C9 C10 C5 -0.5(3) . . . . ? C5 C10 C11 C12 2.1(3) . . . . ? C9 C10 C11 C12 -178.0(2) . . . . ? C5 C10 C11 N1 -175.80(18) . . . . ? C9 C10 C11 N1 4.1(3) . . . . ? C14 N1 C11 C12 71.6(3) . . . . ? C14 N1 C11 C10 -110.5(2) . . . . ? C10 C11 C12 O3 172.20(18) . . . . ? N1 C11 C12 O3 -9.9(3) . . . . ? C10 C11 C12 C3 -4.5(3) . . . . ? N1 C11 C12 C3 173.35(18) . . . . ? C13 O3 C12 C11 97.1(2) . . . . ? C13 O3 C12 C3 -86.2(2) . . . . ? C4 C3 C12 C11 3.4(3) . . . . ? C2 C3 C12 C11 -176.1(2) . . . . ? C4 C3 C12 O3 -173.21(19) . . . . ? C2 C3 C12 O3 7.2(3) . . . . ? C11 N1 C14 O4 7.8(3) . . . . ? C11 N1 C14 C15 -169.5(2) . . . . ? O4 C14 C15 C16 -128.3(2) . . . . ? N1 C14 C15 C16 48.9(3) . . . . ? O4 C14 C15 C24 51.0(3) . . . . ? N1 C14 C15 C24 -131.8(2) . . . . ? C24 C15 C16 C17 1.1(3) . . . . ? C14 C15 C16 C17 -179.58(18) . . . . ? C15 C16 C17 C18 175.3(2) . . . . ? C15 C16 C17 C22 -3.4(3) . . . . ? C22 C17 C18 C19 0.4(3) . . . . ? C16 C17 C18 C19 -178.2(2) . . . . ? C17 C18 C19 C20 -0.7(4) . . . . ? C18 C19 C20 C21 0.2(4) . . . . ? C19 C20 C21 C22 0.6(4) . . . . ? C18 C17 C22 C23 -176.1(2) . . . . ? C16 C17 C22 C23 2.6(3) . . . . ? C18 C17 C22 C21 0.4(3) . . . . ? C16 C17 C22 C21 179.0(2) . . . . ? C20 C21 C22 C17 -0.9(4) . . . . ? C20 C21 C22 C23 175.3(2) . . . . ? C17 C22 C23 C24 0.4(3) . . . . ? C21 C22 C23 C24 -175.8(2) . . . . ? C17 C22 C23 N2 178.5(2) . . . . ? C21 C22 C23 N2 2.3(3) . . . . ? O6 N2 C23 C24 70.2(3) . . . . ? O7 N2 C23 C24 -110.2(3) . . . . ? O6 N2 C23 C22 -108.0(3) . . . . ? O7 N2 C23 C22 71.5(3) . . . . ? C22 C23 C24 O5 176.32(19) . . . . ? N2 C23 C24 O5 -1.8(3) . . . . ? C22 C23 C24 C15 -2.7(3) . . . . ? N2 C23 C24 C15 179.1(2) . . . . ? C25 O5 C24 C23 -104.1(2) . . . . ? C25 O5 C24 C15 75.0(2) . . . . ? C16 C15 C24 C23 2.0(3) . . . . ? C14 C15 C24 C23 -177.37(19) . . . . ? C16 C15 C24 O5 -177.07(18) . . . . ? C14 C15 C24 O5 3.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.171 _refine_diff_density_min -0.108 _refine_diff_density_rms 0.028 # Attachment '7c.cif' ##Title:Sterically Controlled Naphthalene Homo-Oligoamides with Interesting ##Structural Architectures ##Communicated to OBC ##By Panchami Prabhakaran, Vedavati G. Puranik, ##P.R.Rajamohanan, Hans-J\"org Hofmann and Gangadhar J. Sanjayan ##Division of Organic Chemistry,Central NMR Facility, Centre For Materials ##Characterization, National Chemical Laboratory Pune 411 008, India.and ##Universit\"at Leipzig, Fakult\"at f\"ur Biowissenschaften, Pharmazie und Psychologie, ##Institut f\"ur Biochemie, Br\"uderstra\&se 34, D-04103 Leipzig (Germany) data_C26H23Cl3N2O5compound7c _database_code_depnum_ccdc_archive 'CCDC 691284' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'aromatic amide' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H23 Cl3 N2 O5' _chemical_formula_weight 549.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1275(13) _cell_length_b 10.7976(14) _cell_length_c 11.7307(14) _cell_angle_alpha 96.883(3) _cell_angle_beta 94.267(3) _cell_angle_gamma 90.920(3) _cell_volume 1269.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 638 _cell_measurement_theta_min 2.424 _cell_measurement_theta_max 19.6995 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.402 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9572 _exptl_absorpt_correction_T_max 0.9888 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10361 _diffrn_reflns_av_R_equivalents 0.2090 _diffrn_reflns_av_sigmaI/netI 0.3550 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 23.50 _reflns_number_total 3749 _reflns_number_gt 1441 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _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 'SHELXTL and PLATON' _computing_publication_material SHELXTL _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^)+(0.0000P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3749 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2465 _refine_ls_R_factor_gt 0.0705 _refine_ls_wR_factor_ref 0.2732 _refine_ls_wR_factor_gt 0.1925 _refine_ls_goodness_of_fit_ref 0.790 _refine_ls_restrained_S_all 0.790 _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 O1 O 0.7614(6) 0.3294(4) -0.0519(5) 0.0767(16) Uani 1 1 d . . . O2 O 0.9096(5) 0.2771(4) -0.1774(5) 0.0723(16) Uani 1 1 d . . . O3 O 0.9524(5) 0.4770(4) -0.3092(4) 0.0695(15) Uani 1 1 d . . . O4 O 0.6232(5) 0.8388(5) -0.0030(4) 0.0736(16) Uani 1 1 d . . . O5 O 0.8423(5) 0.8465(4) 0.3138(4) 0.0571(13) Uani 1 1 d . . . N1 N 0.8090(6) 0.7740(4) 0.0817(4) 0.0469(14) Uani 1 1 d . . . H1 H 0.8602 0.7768 0.1439 0.056 Uiso 1 1 calc R . . N2 N 0.4119(6) 1.1546(5) 0.2569(5) 0.0665(18) Uani 1 1 d . . . H2A H 0.3711 1.1536 0.1898 0.080 Uiso 1 1 calc R . . H2B H 0.3864 1.2030 0.3143 0.080 Uiso 1 1 calc R . . C1 C 0.7359(9) 0.1987(6) -0.0397(8) 0.090(3) Uani 1 1 d . . . H1A H 0.7081 0.1542 -0.1137 0.135 Uiso 1 1 calc R . . H1B H 0.6675 0.1924 0.0119 0.135 Uiso 1 1 calc R . . H1C H 0.8154 0.1632 -0.0094 0.135 Uiso 1 1 calc R . . C2 C 0.8513(8) 0.3550(6) -0.1222(7) 0.0545(19) Uani 1 1 d . . . C3 C 0.8656(6) 0.4933(5) -0.1225(6) 0.0450(17) Uani 1 1 d . . . C4 C 0.9137(6) 0.5459(6) -0.2117(6) 0.0512(18) Uani 1 1 d . . . C5 C 0.9309(6) 0.6765(6) -0.2090(5) 0.0453(17) Uani 1 1 d . . . C6 C 0.9820(7) 0.7310(7) -0.2994(6) 0.061(2) Uani 1 1 d . . . H6 H 1.0041 0.6809 -0.3650 0.073 Uiso 1 1 calc R . . C7 C 0.9999(7) 0.8584(7) -0.2916(7) 0.066(2) Uani 1 1 d . . . H7 H 1.0354 0.8939 -0.3514 0.079 Uiso 1 1 calc R . . C8 C 0.9651(7) 0.9347(6) -0.1944(7) 0.061(2) Uani 1 1 d . . . H8 H 0.9770 1.0208 -0.1900 0.073 Uiso 1 1 calc R . . C9 C 0.9140(6) 0.8845(6) -0.1064(6) 0.0502(18) Uani 1 1 d . . . H9 H 0.8899 0.9364 -0.0426 0.060 Uiso 1 1 calc R . . C10 C 0.8970(6) 0.7542(5) -0.1104(5) 0.0392(16) Uani 1 1 d . . . C11 C 0.8445(6) 0.6983(5) -0.0187(5) 0.0437(17) Uani 1 1 d . . . C12 C 0.8294(6) 0.5744(5) -0.0252(6) 0.0493(18) Uani 1 1 d . . . H12 H 0.7943 0.5400 0.0354 0.059 Uiso 1 1 calc R . . C13 C 0.8513(10) 0.4291(10) -0.3920(8) 0.125(4) Uani 1 1 d . . . H13A H 0.7747 0.4079 -0.3542 0.187 Uiso 1 1 calc R . . H13B H 0.8814 0.3558 -0.4363 0.187 Uiso 1 1 calc R . . H13C H 0.8288 0.4908 -0.4422 0.187 Uiso 1 1 calc R . . C14 C 0.6999(8) 0.8401(6) 0.0832(6) 0.0499(18) Uani 1 1 d . . . C15 C 0.6682(7) 0.9200(5) 0.1915(6) 0.0467(17) Uani 1 1 d . . . C16 C 0.7354(6) 0.9206(5) 0.2974(5) 0.0433(16) Uani 1 1 d . . . C17 C 0.6993(6) 1.0025(5) 0.3933(5) 0.0424(17) Uani 1 1 d . . . C18 C 0.7710(7) 1.0089(6) 0.5014(5) 0.0527(19) Uani 1 1 d . . . H18 H 0.8437 0.9585 0.5107 0.063 Uiso 1 1 calc R . . C19 C 0.7349(8) 1.0884(7) 0.5932(6) 0.068(2) Uani 1 1 d . . . H19 H 0.7847 1.0932 0.6635 0.082 Uiso 1 1 calc R . . C20 C 0.6255(8) 1.1613(7) 0.5821(6) 0.063(2) Uani 1 1 d . . . H20 H 0.5991 1.2119 0.6458 0.076 Uiso 1 1 calc R . . C21 C 0.5560(7) 1.1595(6) 0.4781(6) 0.0563(19) Uani 1 1 d . . . H21 H 0.4842 1.2113 0.4709 0.068 Uiso 1 1 calc R . . C22 C 0.5909(7) 1.0804(5) 0.3813(5) 0.0403(16) Uani 1 1 d . . . C23 C 0.5193(7) 1.0776(5) 0.2725(6) 0.0459(17) Uani 1 1 d . . . C24 C 0.5609(7) 0.9998(5) 0.1813(6) 0.0477(18) Uani 1 1 d . . . H24 H 0.5158 1.0001 0.1093 0.057 Uiso 1 1 calc R . . C25 C 0.8087(9) 0.7331(7) 0.3604(7) 0.088(3) Uani 1 1 d . . . H25A H 0.8831 0.7087 0.4074 0.131 Uiso 1 1 calc R . . H25B H 0.7862 0.6680 0.2984 0.131 Uiso 1 1 calc R . . H25C H 0.7345 0.7472 0.4063 0.131 Uiso 1 1 calc R . . C26 C 0.4520(12) 0.5743(9) 0.7650(12) 0.120(4) Uani 1 1 d . . . Cl1 Cl 0.4704(18) 0.4423(14) 0.8549(15) 0.114(3) Uani 0.50 1 d P A 1 Cl2 Cl 0.2943(16) 0.6130(10) 0.7613(12) 0.110(5) Uani 0.50 1 d P A 1 Cl3 Cl 0.4685(12) 0.5013(11) 0.6096(9) 0.129(3) Uani 0.50 1 d P A 1 Cl1' Cl 0.488(2) 0.484(2) 0.854(2) 0.220(11) Uani 0.50 1 d P A 2 Cl2' Cl 0.285(2) 0.6142(18) 0.7466(18) 0.186(9) Uani 0.50 1 d P A 2 Cl3' Cl 0.5409(14) 0.5309(12) 0.6636(11) 0.182(5) Uani 0.50 1 d P A 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 O1 0.089(4) 0.039(3) 0.105(5) 0.004(3) 0.033(4) 0.001(3) O2 0.078(4) 0.052(3) 0.081(4) -0.021(3) 0.010(3) 0.015(3) O3 0.076(4) 0.067(3) 0.060(3) -0.023(3) 0.022(3) 0.003(3) O4 0.074(4) 0.107(4) 0.035(3) -0.013(3) -0.007(3) 0.043(3) O5 0.062(3) 0.065(3) 0.043(3) 0.004(2) -0.003(2) 0.021(3) N1 0.057(4) 0.049(3) 0.032(3) -0.004(2) -0.003(3) 0.020(3) N2 0.072(5) 0.078(4) 0.045(4) -0.010(3) -0.010(3) 0.031(4) C1 0.110(7) 0.041(4) 0.120(8) 0.006(4) 0.019(6) -0.007(4) C2 0.049(5) 0.044(4) 0.065(5) -0.008(4) -0.007(4) -0.001(4) C3 0.038(4) 0.044(4) 0.049(4) -0.009(3) -0.003(3) 0.005(3) C4 0.043(5) 0.052(4) 0.054(5) -0.012(4) 0.001(4) 0.000(3) C5 0.034(4) 0.062(4) 0.038(4) -0.007(3) 0.004(3) -0.001(3) C6 0.062(5) 0.076(5) 0.044(4) 0.003(4) 0.013(4) -0.007(4) C7 0.057(5) 0.082(5) 0.063(5) 0.022(5) 0.010(4) -0.014(4) C8 0.058(5) 0.052(4) 0.071(6) 0.010(4) -0.006(4) -0.006(4) C9 0.041(4) 0.055(4) 0.052(5) 0.001(3) -0.004(3) -0.002(3) C10 0.031(4) 0.036(3) 0.050(4) 0.003(3) 0.001(3) 0.004(3) C11 0.045(4) 0.047(4) 0.034(4) -0.012(3) 0.000(3) 0.002(3) C12 0.049(5) 0.046(4) 0.050(4) -0.001(3) -0.006(3) 0.010(3) C13 0.104(8) 0.178(10) 0.073(7) -0.060(7) 0.007(6) -0.011(7) C14 0.066(6) 0.046(4) 0.036(4) -0.003(3) 0.006(4) 0.012(4) C15 0.047(4) 0.047(4) 0.045(4) 0.005(3) -0.001(3) 0.005(3) C16 0.043(4) 0.040(3) 0.048(4) 0.009(3) 0.004(3) 0.011(3) C17 0.048(4) 0.045(3) 0.032(4) -0.003(3) 0.004(3) -0.005(3) C18 0.052(5) 0.058(4) 0.046(4) 0.003(3) -0.010(4) 0.003(3) C19 0.082(6) 0.076(5) 0.040(5) -0.011(4) -0.011(4) 0.010(4) C20 0.081(6) 0.065(5) 0.041(5) -0.003(3) 0.008(4) 0.008(4) C21 0.064(5) 0.046(4) 0.061(5) 0.012(3) 0.006(4) 0.004(3) C22 0.057(5) 0.032(3) 0.030(4) -0.007(3) 0.005(3) 0.003(3) C23 0.044(5) 0.043(4) 0.051(4) 0.005(3) 0.006(3) 0.004(3) C24 0.053(5) 0.048(4) 0.040(4) 0.002(3) -0.001(3) 0.009(3) C25 0.109(8) 0.073(5) 0.085(7) 0.019(5) 0.009(5) 0.049(5) C26 0.121(10) 0.093(7) 0.154(11) 0.008(7) 0.067(9) 0.013(7) Cl1 0.093(7) 0.136(6) 0.115(7) 0.031(5) -0.006(5) 0.009(5) Cl2 0.130(12) 0.091(5) 0.117(7) 0.012(5) 0.057(7) 0.036(6) Cl3 0.162(9) 0.116(5) 0.111(7) 0.004(4) 0.045(5) 0.017(5) Cl1' 0.137(11) 0.31(3) 0.219(14) 0.124(16) -0.063(9) -0.028(13) Cl2' 0.108(12) 0.207(14) 0.248(17) 0.070(11) -0.026(10) 0.035(9) Cl3' 0.234(16) 0.147(9) 0.188(13) 0.036(9) 0.124(10) 0.063(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.322(9) . ? O1 C1 1.456(8) . ? O2 C2 1.190(8) . ? O3 C4 1.374(8) . ? O3 C13 1.405(9) . ? O4 C14 1.228(7) . ? O5 C16 1.371(7) . ? O5 C25 1.446(9) . ? N1 C14 1.325(8) . ? N1 C11 1.424(7) . ? N1 H1 0.8600 . ? N2 C23 1.394(8) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.498(9) . ? C3 C4 1.366(9) . ? C3 C12 1.427(8) . ? C4 C5 1.414(9) . ? C5 C6 1.401(9) . ? C5 C10 1.413(8) . ? C6 C7 1.376(10) . ? C6 H6 0.9300 . ? C7 C8 1.396(10) . ? C7 H7 0.9300 . ? C8 C9 1.353(9) . ? C8 H8 0.9300 . ? C9 C10 1.409(8) . ? C9 H9 0.9300 . ? C10 C11 1.426(8) . ? C11 C12 1.337(8) . ? C12 H12 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.506(9) . ? C15 C16 1.370(9) . ? C15 C24 1.405(9) . ? C16 C17 1.420(8) . ? C17 C22 1.403(9) . ? C17 C18 1.407(8) . ? C18 C19 1.370(9) . ? C18 H18 0.9300 . ? C19 C20 1.376(10) . ? C19 H19 0.9300 . ? C20 C21 1.360(9) . ? C20 H20 0.9300 . ? C21 C22 1.407(9) . ? C21 H21 0.9300 . ? C22 C23 1.417(8) . ? C23 C24 1.375(8) . ? C24 H24 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 Cl1' 1.54(3) . ? C26 Cl3' 1.576(16) . ? C26 Cl2 1.657(19) . ? C26 Cl2' 1.76(2) . ? C26 Cl1 1.88(2) . ? C26 Cl3 1.917(17) . ? 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 O1 C1 117.6(6) . . ? C4 O3 C13 116.8(6) . . ? C16 O5 C25 113.0(5) . . ? C14 N1 C11 122.6(5) . . ? C14 N1 H1 118.7 . . ? C11 N1 H1 118.7 . . ? C23 N2 H2A 120.0 . . ? C23 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O1 123.5(6) . . ? O2 C2 C3 126.4(8) . . ? O1 C2 C3 110.1(6) . . ? C4 C3 C12 118.1(6) . . ? C4 C3 C2 122.8(6) . . ? C12 C3 C2 119.2(7) . . ? C3 C4 O3 123.1(6) . . ? C3 C4 C5 122.1(6) . . ? O3 C4 C5 114.8(6) . . ? C6 C5 C10 119.0(6) . . ? C6 C5 C4 122.5(6) . . ? C10 C5 C4 118.5(6) . . ? C7 C6 C5 120.3(7) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 120.3(7) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 120.5(6) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.7(7) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C5 119.1(6) . . ? C9 C10 C11 122.1(6) . . ? C5 C10 C11 118.9(5) . . ? C12 C11 N1 119.1(6) . . ? C12 C11 C10 120.6(6) . . ? N1 C11 C10 120.3(5) . . ? C11 C12 C3 121.9(7) . . ? C11 C12 H12 119.1 . . ? C3 C12 H12 119.1 . . ? O3 C13 H13A 109.5 . . ? O3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O4 C14 N1 121.2(6) . . ? O4 C14 C15 118.5(7) . . ? N1 C14 C15 120.3(6) . . ? C16 C15 C24 118.3(6) . . ? C16 C15 C14 125.2(7) . . ? C24 C15 C14 116.4(6) . . ? C15 C16 O5 121.7(6) . . ? C15 C16 C17 120.5(6) . . ? O5 C16 C17 117.7(5) . . ? C22 C17 C18 118.5(6) . . ? C22 C17 C16 120.0(5) . . ? C18 C17 C16 121.5(7) . . ? C19 C18 C17 120.8(7) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 120.5(7) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 120.1(7) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 121.1(7) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C17 C22 C21 118.9(6) . . ? C17 C22 C23 119.4(6) . . ? C21 C22 C23 121.6(7) . . ? C24 C23 N2 120.5(6) . . ? C24 C23 C22 118.3(7) . . ? N2 C23 C22 121.1(6) . . ? C23 C24 C15 123.3(6) . . ? C23 C24 H24 118.4 . . ? C15 C24 H24 118.4 . . ? O5 C25 H25A 109.5 . . ? O5 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O5 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? Cl1' C26 Cl3' 103.5(12) . . ? Cl1' C26 Cl2 112.8(12) . . ? Cl3' C26 Cl2 130.1(12) . . ? Cl1' C26 Cl2' 117.0(13) . . ? Cl3' C26 Cl2' 124.6(12) . . ? Cl2 C26 Cl2' 5.5(11) . . ? Cl1' C26 Cl1 11.9(13) . . ? Cl3' C26 Cl1 101.6(9) . . ? Cl2 C26 Cl1 107.0(9) . . ? Cl2' C26 Cl1 110.5(10) . . ? Cl1' C26 Cl3 113.0(11) . . ? Cl3' C26 Cl3 29.8(6) . . ? Cl2 C26 Cl3 102.1(9) . . ? Cl2' C26 Cl3 96.9(10) . . ? Cl1 C26 Cl3 105.5(7) . . ? 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 C1 O1 C2 O2 1.7(11) . . . . ? C1 O1 C2 C3 -179.1(6) . . . . ? O2 C2 C3 C4 22.3(11) . . . . ? O1 C2 C3 C4 -156.8(6) . . . . ? O2 C2 C3 C12 -156.9(7) . . . . ? O1 C2 C3 C12 24.0(8) . . . . ? C12 C3 C4 O3 179.6(6) . . . . ? C2 C3 C4 O3 0.4(10) . . . . ? C12 C3 C4 C5 1.4(9) . . . . ? C2 C3 C4 C5 -177.8(6) . . . . ? C13 O3 C4 C3 78.9(9) . . . . ? C13 O3 C4 C5 -102.8(8) . . . . ? C3 C4 C5 C6 179.0(6) . . . . ? O3 C4 C5 C6 0.6(9) . . . . ? C3 C4 C5 C10 0.1(9) . . . . ? O3 C4 C5 C10 -178.3(5) . . . . ? C10 C5 C6 C7 0.5(10) . . . . ? C4 C5 C6 C7 -178.4(6) . . . . ? C5 C6 C7 C8 -1.1(11) . . . . ? C6 C7 C8 C9 0.4(11) . . . . ? C7 C8 C9 C10 1.0(10) . . . . ? C8 C9 C10 C5 -1.6(9) . . . . ? C8 C9 C10 C11 179.5(6) . . . . ? C6 C5 C10 C9 0.9(9) . . . . ? C4 C5 C10 C9 179.8(5) . . . . ? C6 C5 C10 C11 179.8(6) . . . . ? C4 C5 C10 C11 -1.3(8) . . . . ? C14 N1 C11 C12 -105.3(7) . . . . ? C14 N1 C11 C10 75.4(8) . . . . ? C9 C10 C11 C12 179.9(6) . . . . ? C5 C10 C11 C12 1.0(9) . . . . ? C9 C10 C11 N1 -0.8(9) . . . . ? C5 C10 C11 N1 -179.8(6) . . . . ? N1 C11 C12 C3 -178.7(6) . . . . ? C10 C11 C12 C3 0.5(9) . . . . ? C4 C3 C12 C11 -1.7(9) . . . . ? C2 C3 C12 C11 177.5(6) . . . . ? C11 N1 C14 O4 0.4(10) . . . . ? C11 N1 C14 C15 -179.1(5) . . . . ? O4 C14 C15 C16 172.2(6) . . . . ? N1 C14 C15 C16 -8.3(10) . . . . ? O4 C14 C15 C24 -7.9(9) . . . . ? N1 C14 C15 C24 171.6(6) . . . . ? C24 C15 C16 O5 -179.1(6) . . . . ? C14 C15 C16 O5 0.7(10) . . . . ? C24 C15 C16 C17 -1.7(9) . . . . ? C14 C15 C16 C17 178.2(6) . . . . ? C25 O5 C16 C15 -98.6(7) . . . . ? C25 O5 C16 C17 83.9(7) . . . . ? C15 C16 C17 C22 2.5(9) . . . . ? O5 C16 C17 C22 180.0(5) . . . . ? C15 C16 C17 C18 -176.9(6) . . . . ? O5 C16 C17 C18 0.6(9) . . . . ? C22 C17 C18 C19 0.6(9) . . . . ? C16 C17 C18 C19 -180.0(6) . . . . ? C17 C18 C19 C20 1.7(11) . . . . ? C18 C19 C20 C21 -3.2(11) . . . . ? C19 C20 C21 C22 2.3(11) . . . . ? C18 C17 C22 C21 -1.5(9) . . . . ? C16 C17 C22 C21 179.1(6) . . . . ? C18 C17 C22 C23 178.5(6) . . . . ? C16 C17 C22 C23 -0.9(9) . . . . ? C20 C21 C22 C17 0.0(9) . . . . ? C20 C21 C22 C23 -180.0(6) . . . . ? C17 C22 C23 C24 -1.3(9) . . . . ? C21 C22 C23 C24 178.7(6) . . . . ? C17 C22 C23 N2 -179.3(5) . . . . ? C21 C22 C23 N2 0.7(9) . . . . ? N2 C23 C24 C15 -179.9(6) . . . . ? C22 C23 C24 C15 2.1(9) . . . . ? C16 C15 C24 C23 -0.6(9) . . . . ? C14 C15 C24 C23 179.5(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.187 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.043