# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Andrew J.P. White' _publ_contact_author_email a.white@imperial.ac.uk _publ_section_title ; ; loop_ _publ_author_name N.Long 'A. Kornyshev' 'K. Kowalski' 'Marina Kuimova' 'A. G. Taylor' 'A J.P. White ' # Attachment 'Dalton 07-08.cif' data_Compound_3 _database_code_depnum_ccdc_archive 'CCDC 696198' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H18 N2 O2' _chemical_formula_sum 'C24 H18 N2 O2' _chemical_formula_weight 366.40 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 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 13.3702(3) _cell_length_b 15.0329(3) _cell_length_c 9.6952(2) _cell_angle_alpha 90 _cell_angle_beta 104.763(2) _cell_angle_gamma 90 _cell_volume 1884.34(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9597 _cell_measurement_theta_min 4.0278 _cell_measurement_theta_max 32.5824 _exptl_crystal_description 'blocky needles' _exptl_crystal_colour Orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.84222 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur 3' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 15.9863 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17901 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_theta_max 32.64 _reflns_number_total 6348 _reflns_number_gt 4504 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0723P)^2^+0.1669P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6348 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1426 _refine_ls_wR_factor_gt 0.1306 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _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 N1 N 0.36381(7) 0.83257(6) 0.68217(10) 0.0360(2) Uani 1 1 d . . . C2 C 0.31476(8) 0.75032(6) 0.64322(11) 0.02999(19) Uani 1 1 d . . . C3 C 0.33843(8) 0.67712(7) 0.73574(10) 0.0320(2) Uani 1 1 d . . . H3A H 0.3890 0.6831 0.8240 0.038 Uiso 1 1 calc R . . C4 C 0.28888(8) 0.59631(6) 0.69978(10) 0.0309(2) Uani 1 1 d . . . H4A H 0.3060 0.5478 0.7642 0.037 Uiso 1 1 calc R . . C5 C 0.21397(7) 0.58450(6) 0.57040(10) 0.02713(18) Uani 1 1 d . . . C6 C 0.19373(7) 0.65700(6) 0.47716(10) 0.02924(19) Uani 1 1 d . . . H6A H 0.1451 0.6504 0.3874 0.035 Uiso 1 1 calc R . . C7 C 0.24255(8) 0.73817(6) 0.51184(10) 0.0305(2) Uani 1 1 d . . . H7A H 0.2269 0.7861 0.4459 0.037 Uiso 1 1 calc R . . C8 C 0.15773(7) 0.49955(6) 0.53427(10) 0.02699(18) Uani 1 1 d . . . C9 C 0.14672(8) 0.44088(7) 0.64130(11) 0.0331(2) Uani 1 1 d . . . H9A H 0.1742 0.4568 0.7384 0.040 Uiso 1 1 calc R . . C10 C 0.09658(8) 0.35998(7) 0.60902(11) 0.0340(2) Uani 1 1 d . . . H10A H 0.0909 0.3201 0.6827 0.041 Uiso 1 1 calc R . . C11 C 0.05504(7) 0.33859(6) 0.46760(11) 0.0311(2) Uani 1 1 d . . . C12 C 0.06114(9) 0.39537(7) 0.35820(11) 0.0381(2) Uani 1 1 d . . . H12A H 0.0305 0.3801 0.2616 0.046 Uiso 1 1 calc R . . C13 C 0.11315(9) 0.47530(7) 0.39273(11) 0.0357(2) Uani 1 1 d . . . H13A H 0.1186 0.5146 0.3183 0.043 Uiso 1 1 calc R . . C14 C 0.32111(8) 0.91504(6) 0.62469(11) 0.0322(2) Uani 1 1 d . . . C15 C 0.21526(9) 0.93181(7) 0.59333(12) 0.0362(2) Uani 1 1 d . . . H15A H 0.1691 0.8864 0.6065 0.043 Uiso 1 1 calc R . . C16 C 0.17705(10) 1.01467(8) 0.54283(12) 0.0416(3) Uani 1 1 d . . . H16A H 0.1047 1.0255 0.5210 0.050 Uiso 1 1 calc R . . C17 C 0.24314(11) 1.08181(7) 0.52387(12) 0.0446(3) Uani 1 1 d . . . H17A H 0.2165 1.1386 0.4902 0.054 Uiso 1 1 calc R . . C18 C 0.34825(11) 1.06543(7) 0.55433(13) 0.0442(3) Uani 1 1 d . . . H18A H 0.3940 1.1112 0.5414 0.053 Uiso 1 1 calc R . . C19 C 0.38760(9) 0.98251(7) 0.60374(12) 0.0382(2) Uani 1 1 d . . . H19A H 0.4599 0.9717 0.6233 0.046 Uiso 1 1 calc R . . C20 C 0.45881(8) 0.83592(6) 0.79087(12) 0.0351(2) Uani 1 1 d . . . C21 C 0.46314(10) 0.87917(8) 0.91772(13) 0.0445(3) Uani 1 1 d . . . H21A H 0.4029 0.9054 0.9353 0.053 Uiso 1 1 calc R . . C22 C 0.55815(14) 0.88356(10) 1.01987(16) 0.0658(5) Uani 1 1 d . . . H22A H 0.5630 0.9135 1.1076 0.079 Uiso 1 1 calc R . . C23 C 0.64530(12) 0.84440(11) 0.9934(2) 0.0797(6) Uani 1 1 d . . . H23A H 0.7096 0.8476 1.0631 0.096 Uiso 1 1 calc R . . C24 C 0.63898(11) 0.80145(10) 0.8680(2) 0.0742(6) Uani 1 1 d . . . H24A H 0.6989 0.7743 0.8509 0.089 Uiso 1 1 calc R . . C25 C 0.54668(10) 0.79711(8) 0.76576(18) 0.0525(3) Uani 1 1 d . . . H25A H 0.5430 0.7676 0.6780 0.063 Uiso 1 1 calc R . . N26 N 0.00388(7) 0.25249(6) 0.43283(11) 0.0369(2) Uani 1 1 d . . . O27 O 0.01556(8) 0.19576(5) 0.52635(11) 0.0519(2) Uani 1 1 d . . . O28 O -0.04867(9) 0.24059(7) 0.31063(10) 0.0588(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0354(4) 0.0244(4) 0.0435(5) -0.0001(3) 0.0012(4) -0.0035(3) C2 0.0302(4) 0.0259(4) 0.0340(5) -0.0016(3) 0.0083(4) -0.0024(3) C3 0.0319(5) 0.0302(5) 0.0306(5) -0.0006(4) 0.0021(4) -0.0040(4) C4 0.0333(5) 0.0274(4) 0.0295(4) 0.0021(3) 0.0033(4) -0.0024(3) C5 0.0282(4) 0.0260(4) 0.0268(4) -0.0008(3) 0.0063(3) -0.0013(3) C6 0.0308(4) 0.0306(4) 0.0256(4) 0.0000(3) 0.0058(3) -0.0002(3) C7 0.0349(5) 0.0274(4) 0.0293(4) 0.0026(3) 0.0081(4) 0.0000(3) C8 0.0262(4) 0.0270(4) 0.0273(4) -0.0016(3) 0.0059(3) -0.0007(3) C9 0.0370(5) 0.0332(5) 0.0269(4) -0.0007(4) 0.0043(4) -0.0057(4) C10 0.0358(5) 0.0317(5) 0.0335(5) 0.0020(4) 0.0072(4) -0.0052(4) C11 0.0281(4) 0.0285(4) 0.0374(5) -0.0067(4) 0.0094(4) -0.0037(3) C12 0.0438(6) 0.0396(6) 0.0293(5) -0.0071(4) 0.0065(4) -0.0087(4) C13 0.0439(6) 0.0352(5) 0.0269(5) -0.0004(4) 0.0070(4) -0.0080(4) C14 0.0385(5) 0.0263(4) 0.0315(5) -0.0019(3) 0.0081(4) -0.0019(4) C15 0.0388(5) 0.0332(5) 0.0379(5) -0.0003(4) 0.0119(4) 0.0005(4) C16 0.0464(6) 0.0374(5) 0.0390(6) -0.0020(4) 0.0073(5) 0.0070(5) C17 0.0617(8) 0.0304(5) 0.0365(6) 0.0017(4) 0.0031(5) 0.0035(5) C18 0.0573(7) 0.0316(5) 0.0410(6) 0.0022(4) 0.0076(5) -0.0096(5) C19 0.0411(6) 0.0325(5) 0.0397(5) -0.0005(4) 0.0080(4) -0.0065(4) C20 0.0294(5) 0.0258(4) 0.0473(6) 0.0024(4) 0.0045(4) -0.0050(4) C21 0.0484(6) 0.0380(6) 0.0431(6) 0.0030(5) 0.0044(5) -0.0091(5) C22 0.0790(11) 0.0497(7) 0.0514(8) 0.0116(6) -0.0149(7) -0.0279(7) C23 0.0440(8) 0.0542(8) 0.1147(15) 0.0392(9) -0.0281(8) -0.0220(7) C24 0.0310(6) 0.0454(7) 0.1376(17) 0.0212(9) 0.0057(8) -0.0046(5) C25 0.0373(6) 0.0352(6) 0.0868(10) 0.0024(6) 0.0189(6) -0.0011(5) N26 0.0351(4) 0.0335(4) 0.0449(5) -0.0112(4) 0.0152(4) -0.0073(3) O27 0.0554(5) 0.0302(4) 0.0658(6) 0.0031(4) 0.0077(4) -0.0051(4) O28 0.0715(7) 0.0619(6) 0.0430(5) -0.0196(4) 0.0147(4) -0.0349(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.4055(12) . ? N1 C14 1.4182(13) . ? N1 C20 1.4298(13) . ? C2 C7 1.4004(14) . ? C2 C3 1.4039(14) . ? C3 C4 1.3850(13) . ? C4 C5 1.4029(13) . ? C5 C6 1.3977(13) . ? C5 C8 1.4779(13) . ? C6 C7 1.3843(13) . ? C8 C9 1.3980(13) . ? C8 C13 1.3980(13) . ? C9 C10 1.3854(14) . ? C10 C11 1.3798(14) . ? C11 C12 1.3800(15) . ? C11 N26 1.4628(12) . ? C12 C13 1.3859(14) . ? C14 C15 1.3927(15) . ? C14 C19 1.3972(14) . ? C15 C16 1.3874(15) . ? C16 C17 1.3842(18) . ? C17 C18 1.3826(19) . ? C18 C19 1.3898(16) . ? C20 C21 1.3792(17) . ? C20 C25 1.3877(17) . ? C21 C22 1.3992(19) . ? C22 C23 1.386(3) . ? C23 C24 1.361(3) . ? C24 C25 1.373(2) . ? N26 O27 1.2253(13) . ? N26 O28 1.2268(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C14 123.36(8) . . ? C2 N1 C20 119.68(8) . . ? C14 N1 C20 116.86(8) . . ? C7 C2 C3 118.03(8) . . ? C7 C2 N1 121.70(9) . . ? C3 C2 N1 120.27(9) . . ? C4 C3 C2 120.74(9) . . ? C3 C4 C5 121.53(9) . . ? C6 C5 C4 117.13(8) . . ? C6 C5 C8 121.16(8) . . ? C4 C5 C8 121.70(8) . . ? C7 C6 C5 121.92(9) . . ? C6 C7 C2 120.59(9) . . ? C9 C8 C13 117.70(9) . . ? C9 C8 C5 120.84(8) . . ? C13 C8 C5 121.46(8) . . ? C10 C9 C8 121.51(9) . . ? C11 C10 C9 118.56(9) . . ? C10 C11 C12 122.14(9) . . ? C10 C11 N26 118.77(9) . . ? C12 C11 N26 119.08(9) . . ? C11 C12 C13 118.35(9) . . ? C12 C13 C8 121.70(9) . . ? C15 C14 C19 119.05(10) . . ? C15 C14 N1 121.93(9) . . ? C19 C14 N1 118.97(10) . . ? C16 C15 C14 120.13(10) . . ? C17 C16 C15 120.75(11) . . ? C18 C17 C16 119.36(11) . . ? C17 C18 C19 120.55(11) . . ? C18 C19 C14 120.15(11) . . ? C21 C20 C25 120.63(11) . . ? C21 C20 N1 120.09(10) . . ? C25 C20 N1 119.26(11) . . ? C20 C21 C22 118.53(14) . . ? C23 C22 C21 120.22(16) . . ? C24 C23 C22 120.20(13) . . ? C23 C24 C25 120.48(16) . . ? C24 C25 C20 119.92(15) . . ? O27 N26 O28 123.15(9) . . ? O27 N26 C11 118.78(9) . . ? O28 N26 C11 118.08(9) . . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.316 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.040 #===END data_Compound_6 _database_code_depnum_ccdc_archive 'CCDC 696199' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H21 N2, I' _chemical_formula_sum 'C24 H21 I N2' _chemical_formula_weight 464.33 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' I I -0.4742 1.8119 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.69284(14) _cell_length_b 40.9581(10) _cell_length_c 9.1109(2) _cell_angle_alpha 90 _cell_angle_beta 101.802(2) _cell_angle_gamma 90 _cell_volume 2079.46(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7525 _cell_measurement_theta_min 4.4149 _cell_measurement_theta_max 26.8301 _exptl_crystal_description needles _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 1.550 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93330 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur 3' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 15.9863 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15670 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -49 _diffrn_reflns_limit_k_max 50 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.42 _diffrn_reflns_theta_max 26.87 _reflns_number_total 4216 _reflns_number_gt 3113 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0653P)^2^+1.7160P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4216 _refine_ls_number_parameters 384 _refine_ls_number_restraints 128 _refine_ls_R_factor_all 0.0657 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1199 _refine_ls_wR_factor_gt 0.1134 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.003 _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 I I 0.31598(6) 0.698937(8) 0.57650(3) 0.04769(14) Uani 1 1 d . . . N1 N 1.0495(17) 0.9171(2) 0.4828(10) 0.032(2) Uani 0.50 1 d PD A 1 C2 C 0.9021(11) 0.89085(15) 0.5175(8) 0.029(3) Uani 0.50 1 d PGD A 1 C3 C 0.8040(13) 0.86895(16) 0.4050(7) 0.033(2) Uani 0.50 1 d PGD A 1 H3A H 0.8503 0.8698 0.3106 0.039 Uiso 0.50 1 calc PR A 1 C4 C 0.6382(12) 0.84584(14) 0.4306(7) 0.032(2) Uani 0.50 1 d PGD A 1 H4A H 0.5711 0.8309 0.3538 0.039 Uiso 0.50 1 calc PR A 1 C5 C 0.5705(11) 0.84462(14) 0.5687(8) 0.027(3) Uani 0.50 1 d PGD A 1 C6 C 0.6686(12) 0.86651(16) 0.6812(6) 0.031(2) Uani 0.50 1 d PGD A 1 H6A H 0.6224 0.8657 0.7755 0.038 Uiso 0.50 1 calc PR A 1 C7 C 0.8345(11) 0.88963(14) 0.6555(6) 0.0310(19) Uani 0.50 1 d PGD A 1 H7A H 0.9015 0.9046 0.7324 0.037 Uiso 0.50 1 calc PR A 1 C8 C 0.372(2) 0.8220(3) 0.5910(11) 0.032(4) Uani 0.50 1 d PGD A 1 C9 C 0.215(2) 0.8099(3) 0.4656(9) 0.036(3) Uani 0.50 1 d PGDU A 1 H9A H 0.2347 0.8158 0.3680 0.043 Uiso 0.50 1 calc PR A 1 C10 C 0.0299(18) 0.7891(2) 0.4831(10) 0.043(4) Uani 0.50 1 d PGD A 1 H10A H -0.0774 0.7808 0.3974 0.052 Uiso 0.50 1 calc PR A 1 N11 N 0.0014(16) 0.7804(3) 0.6259(12) 0.038(4) Uani 0.50 1 d PGD A 1 C12 C 0.1584(18) 0.7925(2) 0.7513(9) 0.028(2) Uani 0.50 1 d PGDU A 1 H12A H 0.1389 0.7866 0.8489 0.033 Uiso 0.50 1 calc PR A 1 C13 C 0.3438(18) 0.8133(3) 0.7338(10) 0.027(3) Uani 0.50 1 d PGDU A 1 H13A H 0.4511 0.8216 0.8195 0.033 Uiso 0.50 1 calc PR A 1 C14 C -0.187(3) 0.7581(5) 0.6496(18) 0.029(3) Uani 0.50 1 d PDU A 1 H14A H -0.1328 0.7355 0.6435 0.043 Uiso 0.50 1 calc PR A 1 H14B H -0.3320 0.7617 0.5723 0.043 Uiso 0.50 1 calc PR A 1 H14C H -0.2232 0.7619 0.7488 0.043 Uiso 0.50 1 calc PR A 1 C15 C 1.2046(9) 0.93367(12) 0.6038(5) 0.031(2) Uani 0.50 1 d PGD A 1 C16 C 1.3627(10) 0.91648(10) 0.7132(6) 0.0340(19) Uani 0.50 1 d PGD A 1 H16A H 1.3601 0.8933 0.7134 0.041 Uiso 0.50 1 calc PR A 1 C17 C 1.5247(9) 0.93322(14) 0.8222(5) 0.043(2) Uani 0.50 1 d PGD A 1 H17A H 1.6327 0.9215 0.8969 0.052 Uiso 0.50 1 calc PR A 1 C18 C 1.5285(10) 0.96716(14) 0.8218(6) 0.042(2) Uani 0.50 1 d PGD A 1 H18A H 1.6392 0.9786 0.8963 0.050 Uiso 0.50 1 calc PR A 1 C19 C 1.3705(12) 0.98435(10) 0.7124(7) 0.042(6) Uani 0.50 1 d PGD A 1 H19A H 1.3731 1.0075 0.7121 0.051 Uiso 0.50 1 calc PR A 1 C20 C 1.2085(11) 0.96760(12) 0.6034(6) 0.042(2) Uani 0.50 1 d PGD A 1 H20A H 1.1005 0.9794 0.5286 0.050 Uiso 0.50 1 calc PR A 1 C21 C 1.0486(9) 0.92710(15) 0.3343(5) 0.032(2) Uani 0.50 1 d PGD A 1 C22 C 1.2675(7) 0.93337(16) 0.2948(6) 0.039(2) Uani 0.50 1 d PGD A 1 H22A H 1.4126 0.9309 0.3669 0.047 Uiso 0.50 1 calc PR A 1 C23 C 1.2741(8) 0.94327(16) 0.1498(7) 0.038(2) Uani 0.50 1 d PGD A 1 H23A H 1.4237 0.9476 0.1228 0.046 Uiso 0.50 1 calc PR A 1 C24 C 1.0618(11) 0.94692(16) 0.0442(5) 0.035(3) Uani 0.50 1 d PGD A 1 H24A H 1.0663 0.9537 -0.0549 0.042 Uiso 0.50 1 calc PR A 1 C25 C 0.8429(8) 0.94065(15) 0.0837(5) 0.0365(19) Uani 0.50 1 d PGD A 1 H25A H 0.6977 0.9431 0.0116 0.044 Uiso 0.50 1 calc PR A 1 C26 C 0.8362(7) 0.93074(14) 0.2287(6) 0.0329(18) Uani 0.50 1 d PGD A 1 H26A H 0.6866 0.9265 0.2557 0.040 Uiso 0.50 1 calc PR A 1 N1' N 1.0481(17) 0.9145(2) 0.4135(11) 0.034(2) Uani 0.50 1 d PD B 2 C2' C 0.8912(11) 0.88982(14) 0.4525(8) 0.029(3) Uani 0.50 1 d PGD B 2 C3' C 0.7094(13) 0.87706(16) 0.3420(6) 0.039(2) Uani 0.50 1 d PGD B 2 H3'A H 0.6952 0.8837 0.2406 0.047 Uiso 0.50 1 calc PR B 2 C4' C 0.5485(12) 0.85461(16) 0.3798(7) 0.041(3) Uani 0.50 1 d PGD B 2 H4'A H 0.4243 0.8459 0.3042 0.049 Uiso 0.50 1 calc PR B 2 C5' C 0.5693(10) 0.84493(15) 0.5281(8) 0.030(3) Uani 0.50 1 d PGD B 2 C6' C 0.7510(11) 0.85770(16) 0.6387(6) 0.032(2) Uani 0.50 1 d PGD B 2 H6'A H 0.7652 0.8511 0.7400 0.038 Uiso 0.50 1 calc PR B 2 C7' C 0.9120(10) 0.88014(15) 0.6009(7) 0.034(2) Uani 0.50 1 d PGD B 2 H7'A H 1.0362 0.8889 0.6764 0.041 Uiso 0.50 1 calc PR B 2 C8' C 0.386(2) 0.8216(3) 0.5706(13) 0.029(4) Uani 0.50 1 d PGDU B 2 C9' C 0.244(2) 0.8022(3) 0.4627(10) 0.034(3) Uani 0.50 1 d PGDU B 2 H9'A H 0.2654 0.8026 0.3620 0.041 Uiso 0.50 1 calc PR B 2 C10' C 0.0707(18) 0.7820(2) 0.5021(11) 0.029(3) Uani 0.50 1 d PGDU B 2 H10B H -0.0265 0.7687 0.4284 0.035 Uiso 0.50 1 calc PR B 2 N11' N 0.0395(18) 0.7812(2) 0.6495(12) 0.028(3) Uani 0.50 1 d PGDU B 2 C12' C 0.182(2) 0.8007(2) 0.7574(10) 0.043(4) Uani 0.50 1 d PGDU B 2 H12B H 0.1604 0.8002 0.8581 0.051 Uiso 0.50 1 calc PR B 2 C13' C 0.355(2) 0.8209(2) 0.7179(12) 0.038(3) Uani 0.50 1 d PGDU B 2 H13B H 0.4522 0.8342 0.7917 0.045 Uiso 0.50 1 calc PR B 2 C14' C -0.134(4) 0.7583(6) 0.691(2) 0.052(5) Uani 0.50 1 d PDU B 2 H14D H -0.1499 0.7626 0.7948 0.078 Uiso 0.50 1 calc PR B 2 H14E H -0.0775 0.7358 0.6839 0.078 Uiso 0.50 1 calc PR B 2 H14F H -0.2903 0.7611 0.6238 0.078 Uiso 0.50 1 calc PR B 2 C15' C 1.1509(9) 0.93841(12) 0.5213(6) 0.031(2) Uani 0.50 1 d PGD B 2 C16' C 1.3954(9) 0.94486(14) 0.5442(7) 0.038(2) Uani 0.50 1 d PGD B 2 H16B H 1.4939 0.9326 0.4918 0.046 Uiso 0.50 1 calc PR B 2 C17' C 1.4959(8) 0.96920(16) 0.6438(7) 0.043(2) Uani 0.50 1 d PGD B 2 H17B H 1.6630 0.9736 0.6594 0.052 Uiso 0.50 1 calc PR B 2 C18' C 1.3519(11) 0.98708(14) 0.7205(7) 0.043(6) Uani 0.50 1 d PGD B 2 H18B H 1.4205 1.0037 0.7886 0.051 Uiso 0.50 1 calc PR B 2 C19' C 1.1074(11) 0.98063(12) 0.6977(6) 0.0345(19) Uani 0.50 1 d PGD B 2 H19B H 1.0089 0.9929 0.7501 0.041 Uiso 0.50 1 calc PR B 2 C20' C 1.0069(7) 0.95629(13) 0.5981(6) 0.0306(18) Uani 0.50 1 d PGD B 2 H20B H 0.8398 0.9519 0.5824 0.037 Uiso 0.50 1 calc PR B 2 C21' C 1.0978(11) 0.91622(12) 0.2686(5) 0.0324(19) Uani 0.50 1 d PGD B 2 C22' C 1.1088(12) 0.94665(10) 0.2028(6) 0.036(2) Uani 0.50 1 d PGD B 2 H22B H 1.0786 0.9658 0.2545 0.043 Uiso 0.50 1 calc PR B 2 C23' C 1.1639(13) 0.94899(11) 0.0614(6) 0.037(3) Uani 0.50 1 d PGD B 2 H23B H 1.1714 0.9698 0.0165 0.044 Uiso 0.50 1 calc PR B 2 C24' C 1.2081(12) 0.92090(15) -0.0141(5) 0.042(2) Uani 0.50 1 d PGD B 2 H24B H 1.2458 0.9225 -0.1108 0.051 Uiso 0.50 1 calc PR B 2 C25' C 1.1971(12) 0.89047(12) 0.0516(6) 0.046(2) Uani 0.50 1 d PGD B 2 H25B H 1.2273 0.8713 0.0000 0.055 Uiso 0.50 1 calc PR B 2 C26' C 1.1420(12) 0.88813(10) 0.1930(6) 0.038(2) Uani 0.50 1 d PGD B 2 H26B H 1.1345 0.8673 0.2380 0.045 Uiso 0.50 1 calc PR B 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 I 0.0451(2) 0.0601(2) 0.03761(19) 0.00374(15) 0.00786(13) -0.00625(16) N1 0.041(5) 0.030(5) 0.025(5) -0.001(4) 0.005(5) -0.004(4) C2 0.031(5) 0.037(6) 0.019(7) -0.003(5) 0.006(4) -0.001(4) C3 0.051(6) 0.024(5) 0.029(5) -0.003(4) 0.020(5) -0.005(5) C4 0.037(6) 0.031(5) 0.027(6) -0.009(4) 0.005(5) -0.005(4) C5 0.039(7) 0.029(6) 0.017(4) 0.009(4) 0.012(4) 0.008(5) C6 0.032(5) 0.040(5) 0.023(4) 0.002(4) 0.007(4) -0.001(4) C7 0.034(5) 0.032(5) 0.026(5) -0.003(4) 0.005(4) -0.003(4) C8 0.028(8) 0.021(7) 0.043(9) -0.013(6) -0.006(6) 0.003(6) C9 0.040(6) 0.029(6) 0.037(5) 0.003(4) 0.005(4) 0.007(5) C10 0.053(8) 0.024(5) 0.049(7) 0.009(5) 0.001(6) 0.010(6) N11 0.037(6) 0.029(6) 0.038(6) 0.002(4) -0.016(5) 0.002(4) C12 0.025(4) 0.027(4) 0.031(4) -0.007(3) 0.005(3) -0.005(3) C13 0.027(4) 0.027(4) 0.028(4) 0.004(3) 0.007(3) -0.005(3) C14 0.019(8) 0.039(6) 0.025(7) 0.000(5) -0.003(6) -0.008(5) C15 0.035(5) 0.033(5) 0.031(5) -0.009(4) 0.017(4) -0.010(4) C16 0.027(4) 0.040(5) 0.035(5) -0.005(4) 0.004(4) 0.009(4) C17 0.031(5) 0.065(7) 0.033(5) 0.000(4) 0.003(4) 0.007(4) C18 0.034(5) 0.061(6) 0.033(5) -0.008(4) 0.013(4) -0.016(4) C19 0.050(13) 0.039(11) 0.036(12) -0.008(9) 0.005(10) -0.017(9) C20 0.055(6) 0.036(5) 0.035(5) 0.004(4) 0.012(4) 0.002(4) C21 0.045(5) 0.032(5) 0.021(5) -0.004(4) 0.014(4) -0.005(4) C22 0.033(5) 0.045(5) 0.042(5) -0.003(4) 0.012(4) 0.000(4) C23 0.034(5) 0.042(5) 0.044(6) -0.010(4) 0.020(4) -0.011(4) C24 0.044(8) 0.038(5) 0.027(5) -0.004(4) 0.017(5) -0.015(4) C25 0.033(5) 0.039(5) 0.035(5) 0.000(4) 0.001(4) -0.004(4) C26 0.032(4) 0.031(4) 0.035(5) 0.000(4) 0.008(4) 0.002(4) N1' 0.042(5) 0.035(5) 0.030(6) -0.008(5) 0.014(5) -0.007(4) C2' 0.040(5) 0.024(6) 0.022(7) 0.011(5) 0.010(4) 0.010(4) C3' 0.058(7) 0.034(6) 0.021(5) 0.006(4) 0.001(4) 0.004(5) C4' 0.051(7) 0.042(6) 0.028(5) 0.005(4) -0.001(5) -0.002(5) C5' 0.032(7) 0.023(6) 0.030(6) -0.004(4) -0.006(4) 0.004(5) C6' 0.033(5) 0.034(5) 0.028(5) 0.008(4) 0.008(4) 0.004(4) C7' 0.045(6) 0.036(6) 0.023(6) -0.008(4) 0.009(4) -0.003(4) C8' 0.028(7) 0.034(8) 0.027(6) 0.014(5) 0.009(5) 0.009(6) C9' 0.037(5) 0.023(5) 0.040(5) 0.004(3) 0.001(3) 0.004(4) C10' 0.029(4) 0.024(5) 0.029(4) 0.008(3) -0.007(3) -0.001(4) N11' 0.021(4) 0.027(5) 0.038(5) 0.000(4) 0.011(4) -0.002(3) C12' 0.049(5) 0.037(5) 0.042(5) 0.000(4) 0.008(4) 0.001(4) C13' 0.040(5) 0.033(5) 0.040(5) 0.001(4) 0.008(4) -0.005(3) C14' 0.030(9) 0.062(8) 0.060(13) -0.010(9) 0.000(9) -0.012(7) C15' 0.044(5) 0.024(5) 0.030(5) 0.000(4) 0.018(5) 0.002(4) C16' 0.033(5) 0.038(5) 0.045(5) 0.005(4) 0.010(4) 0.008(4) C17' 0.035(5) 0.057(6) 0.035(5) 0.000(4) 0.000(4) -0.008(4) C18' 0.054(14) 0.042(11) 0.034(12) 0.000(9) 0.012(10) -0.001(10) C19' 0.043(5) 0.027(4) 0.034(5) 0.004(3) 0.008(4) 0.005(4) C20' 0.034(5) 0.027(4) 0.032(4) 0.004(3) 0.010(4) -0.001(3) C21' 0.033(5) 0.042(5) 0.022(4) 0.006(4) 0.006(4) -0.001(4) C22' 0.049(5) 0.022(4) 0.034(5) 0.002(3) 0.003(4) -0.002(4) C23' 0.031(7) 0.043(6) 0.035(6) 0.003(5) 0.003(5) -0.010(5) C24' 0.043(5) 0.059(6) 0.026(4) -0.004(4) 0.007(4) -0.006(4) C25' 0.057(6) 0.052(6) 0.033(5) -0.004(4) 0.016(4) 0.000(5) C26' 0.049(5) 0.035(5) 0.030(4) 0.002(4) 0.012(4) 0.003(4) _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 C21 1.412(9) . ? N1 C15 1.434(9) . ? N1 C2 1.439(8) . ? C2 C3 1.3900 . ? C2 C7 1.3900 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C5 C8 1.506(7) . ? C6 C7 1.3900 . ? C8 C9 1.3900 . ? C8 C13 1.3900 . ? C9 C10 1.3900 . ? C10 N11 1.3900 . ? N11 C12 1.3900 . ? N11 C14 1.461(10) . ? C12 C13 1.3900 . ? C15 C16 1.3900 . ? C15 C20 1.3900 . ? C16 C17 1.3900 . ? C17 C18 1.3900 . ? C18 C19 1.3900 . ? C19 C20 1.3900 . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C22 C23 1.3900 . ? C23 C24 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? N1' C21' 1.408(10) . ? N1' C15' 1.424(9) . ? N1' C2' 1.442(9) . ? C2' C3' 1.3900 . ? C2' C7' 1.3900 . ? C3' C4' 1.3900 . ? C4' C5' 1.3900 . ? C5' C6' 1.3900 . ? C5' C8' 1.520(7) . ? C6' C7' 1.3900 . ? C8' C9' 1.3900 . ? C8' C13' 1.3900 . ? C9' C10' 1.3900 . ? C10' N11' 1.3900 . ? N11' C12' 1.3900 . ? N11' C14' 1.471(11) . ? C12' C13' 1.3900 . ? C15' C16' 1.3900 . ? C15' C20' 1.3900 . ? C16' C17' 1.3900 . ? C17' C18' 1.3900 . ? C18' C19' 1.3900 . ? C19' C20' 1.3900 . ? C21' C22' 1.3900 . ? C21' C26' 1.3900 . ? C22' C23' 1.3900 . ? C23' C24' 1.3900 . ? C24' C25' 1.3900 . ? C25' C26' 1.3900 . ? 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 C21 N1 C15 118.7(6) . . ? C21 N1 C2 122.6(7) . . ? C15 N1 C2 118.7(7) . . ? C3 C2 C7 120.0 . . ? C3 C2 N1 119.0(5) . . ? C7 C2 N1 120.5(5) . . ? C4 C3 C2 120.0 . . ? C3 C4 C5 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 C8 119.8(6) . . ? C4 C5 C8 119.9(5) . . ? C7 C6 C5 120.0 . . ? C6 C7 C2 120.0 . . ? C9 C8 C13 120.0 . . ? C9 C8 C5 118.8(6) . . ? C13 C8 C5 121.2(6) . . ? C10 C9 C8 120.0 . . ? N11 C10 C9 120.0 . . ? C10 N11 C12 120.0 . . ? C10 N11 C14 121.9(8) . . ? C12 N11 C14 118.1(8) . . ? N11 C12 C13 120.0 . . ? C12 C13 C8 120.0 . . ? C16 C15 C20 120.0 . . ? C16 C15 N1 121.2(5) . . ? C20 C15 N1 118.6(5) . . ? C15 C16 C17 120.0 . . ? C18 C17 C16 120.0 . . ? C19 C18 C17 120.0 . . ? C18 C19 C20 120.0 . . ? C19 C20 C15 120.0 . . ? C22 C21 C26 120.0 . . ? C22 C21 N1 118.3(5) . . ? C26 C21 N1 121.7(5) . . ? C23 C22 C21 120.0 . . ? C22 C23 C24 120.0 . . ? C25 C24 C23 120.0 . . ? C24 C25 C26 120.0 . . ? C25 C26 C21 120.0 . . ? C21' N1' C15' 118.7(6) . . ? C21' N1' C2' 121.2(7) . . ? C15' N1' C2' 120.0(7) . . ? C3' C2' C7' 120.0 . . ? C3' C2' N1' 119.5(6) . . ? C7' C2' N1' 120.4(6) . . ? C4' C3' C2' 120.0 . . ? C3' C4' C5' 120.0 . . ? C6' C5' C4' 120.0 . . ? C6' C5' C8' 119.9(6) . . ? C4' C5' C8' 120.0(6) . . ? C7' C6' C5' 120.0 . . ? C6' C7' C2' 120.0 . . ? C9' C8' C13' 120.0 . . ? C9' C8' C5' 120.7(7) . . ? C13' C8' C5' 119.2(7) . . ? C8' C9' C10' 120.0 . . ? N11' C10' C9' 120.0 . . ? C10' N11' C12' 120.0 . . ? C10' N11' C14' 119.3(9) . . ? C12' N11' C14' 120.5(9) . . ? C13' C12' N11' 120.0 . . ? C12' C13' C8' 120.0 . . ? C16' C15' C20' 120.0 . . ? C16' C15' N1' 119.5(5) . . ? C20' C15' N1' 120.5(5) . . ? C15' C16' C17' 120.0 . . ? C18' C17' C16' 120.0 . . ? C19' C18' C17' 120.0 . . ? C18' C19' C20' 120.0 . . ? C19' C20' C15' 120.0 . . ? C22' C21' C26' 120.0 . . ? C22' C21' N1' 118.9(5) . . ? C26' C21' N1' 121.1(5) . . ? C21' C22' C23' 120.0 . . ? C22' C23' C24' 120.0 . . ? C25' C24' C23' 120.0 . . ? C26' C25' C24' 120.0 . . ? C25' C26' C21' 120.0 . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.135 _refine_diff_density_min -0.768 _refine_diff_density_rms 0.090 #===END data_Compound_9 _database_code_depnum_ccdc_archive 'CCDC 696200' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H19 N2, Cl, 0.5(H2 O), 0.25(C H2 Cl2)' _chemical_formula_sum 'C23.25 H20.50 Cl1.50 N2 O0.50' _chemical_formula_weight 389.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 9.0670(17) _cell_length_b 10.852(2) _cell_length_c 21.500(4) _cell_angle_alpha 100.431(15) _cell_angle_beta 90.436(15) _cell_angle_gamma 103.375(16) _cell_volume 2021.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 4.2598 _cell_measurement_theta_max 70.8781 _exptl_crystal_description plates _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 814 _exptl_absorpt_coefficient_mu 2.367 _exptl_absorpt_correction_type 'numeric analytical' _exptl_absorpt_correction_T_min 0.66956 _exptl_absorpt_correction_T_max 0.90138 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54248 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19742 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_sigmaI/netI 0.0645 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 4.38 _diffrn_reflns_theta_max 71.09 _reflns_number_total 7479 _reflns_number_gt 3741 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.1053P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7479 _refine_ls_number_parameters 525 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.1145 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1952 _refine_ls_wR_factor_gt 0.1592 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.942 _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 0.5045(3) 0.6621(3) 0.83474(13) 0.0439(7) Uani 1 1 d . . . C2 C 0.4695(4) 0.7170(3) 0.78402(15) 0.0417(8) Uani 1 1 d . . . C3 C 0.3244(4) 0.7386(4) 0.77605(16) 0.0487(9) Uani 1 1 d . . . H3A H 0.2481 0.7120 0.8041 0.058 Uiso 1 1 calc R . . C4 C 0.2916(4) 0.7979(4) 0.72798(17) 0.0506(9) Uani 1 1 d . . . H4A H 0.1916 0.8086 0.7225 0.061 Uiso 1 1 calc R . . C5 C 0.4021(4) 0.8429(3) 0.68676(16) 0.0460(8) Uani 1 1 d . . . C6 C 0.5455(4) 0.8193(3) 0.69499(16) 0.0466(8) Uani 1 1 d . . . H6A H 0.6228 0.8479 0.6677 0.056 Uiso 1 1 calc R . . C7 C 0.5781(4) 0.7561(3) 0.74133(16) 0.0457(8) Uani 1 1 d . . . H7A H 0.6756 0.7387 0.7444 0.055 Uiso 1 1 calc R . . C8 C 0.3680(4) 0.9112(4) 0.63744(16) 0.0466(8) Uani 1 1 d . . . C9 C 0.2205(4) 0.8887(4) 0.61096(18) 0.0569(10) Uani 1 1 d . . . H9A H 0.1406 0.8270 0.6243 0.068 Uiso 1 1 calc R . . C10 C 0.1912(4) 0.9556(4) 0.56579(18) 0.0614(11) Uani 1 1 d . . . H10A H 0.0913 0.9390 0.5474 0.074 Uiso 1 1 calc R . . N11 N 0.3027(4) 1.0445(3) 0.54733(14) 0.0548(8) Uani 1 1 d D . . H11 H 0.278(5) 1.090(4) 0.5197(16) 0.091(15) Uiso 1 1 d D . . C12 C 0.4461(4) 1.0692(4) 0.57111(17) 0.0525(9) Uani 1 1 d . . . H12A H 0.5234 1.1320 0.5571 0.063 Uiso 1 1 calc R . . C13 C 0.4801(4) 1.0035(4) 0.61562(17) 0.0480(9) Uani 1 1 d . . . H13A H 0.5818 1.0207 0.6321 0.058 Uiso 1 1 calc R . . C14 C 0.6571(4) 0.6702(3) 0.85584(16) 0.0424(8) Uani 1 1 d . . . C15 C 0.7678(4) 0.7842(3) 0.86532(16) 0.0465(8) Uani 1 1 d . . . H15A H 0.7437 0.8607 0.8572 0.056 Uiso 1 1 calc R . . C16 C 0.9129(4) 0.7878(4) 0.88645(18) 0.0509(9) Uani 1 1 d . . . H16A H 0.9881 0.8667 0.8927 0.061 Uiso 1 1 calc R . . C17 C 0.9503(4) 0.6770(4) 0.89869(18) 0.0528(9) Uani 1 1 d . . . H17A H 1.0503 0.6796 0.9133 0.063 Uiso 1 1 calc R . . C18 C 0.8408(4) 0.5640(4) 0.88942(19) 0.0545(10) Uani 1 1 d . . . H18A H 0.8651 0.4877 0.8976 0.065 Uiso 1 1 calc R . . C19 C 0.6954(4) 0.5601(3) 0.86832(18) 0.0495(9) Uani 1 1 d . . . H19A H 0.6205 0.4810 0.8623 0.059 Uiso 1 1 calc R . . C20 C 0.3873(4) 0.5924(3) 0.86781(16) 0.0426(8) Uani 1 1 d . . . C21 C 0.3912(4) 0.6207(3) 0.93365(16) 0.0466(8) Uani 1 1 d . . . H21A H 0.4703 0.6878 0.9561 0.056 Uiso 1 1 calc R . . C22 C 0.2818(4) 0.5525(4) 0.96669(17) 0.0493(9) Uani 1 1 d . . . H22A H 0.2867 0.5717 1.0117 0.059 Uiso 1 1 calc R . . C23 C 0.1645(4) 0.4561(4) 0.93438(18) 0.0504(9) Uani 1 1 d . . . H23A H 0.0882 0.4100 0.9572 0.060 Uiso 1 1 calc R . . C24 C 0.1586(4) 0.4267(3) 0.86865(18) 0.0487(9) Uani 1 1 d . . . H24A H 0.0785 0.3601 0.8466 0.058 Uiso 1 1 calc R . . C25 C 0.2691(4) 0.4940(3) 0.83516(17) 0.0460(8) Uani 1 1 d . . . H25A H 0.2649 0.4735 0.7902 0.055 Uiso 1 1 calc R . . N31 N 0.5654(3) 0.1662(3) 0.82775(14) 0.0513(8) Uani 1 1 d . . . C32 C 0.5189(4) 0.2191(3) 0.77793(16) 0.0456(8) Uani 1 1 d . . . C33 C 0.6222(4) 0.3012(4) 0.74828(17) 0.0509(9) Uani 1 1 d . . . H33A H 0.7271 0.3192 0.7605 0.061 Uiso 1 1 calc R . . C34 C 0.5763(4) 0.3580(4) 0.70096(17) 0.0509(9) Uani 1 1 d . . . H34A H 0.6502 0.4141 0.6815 0.061 Uiso 1 1 calc R . . C35 C 0.4233(4) 0.3340(3) 0.68138(16) 0.0446(8) Uani 1 1 d . . . C36 C 0.3195(4) 0.2474(4) 0.70958(17) 0.0475(8) Uani 1 1 d . . . H36A H 0.2153 0.2261 0.6959 0.057 Uiso 1 1 calc R . . C37 C 0.3660(4) 0.1914(4) 0.75751(16) 0.0484(9) Uani 1 1 d . . . H37A H 0.2929 0.1337 0.7765 0.058 Uiso 1 1 calc R . . C38 C 0.3753(4) 0.3997(4) 0.63328(16) 0.0465(8) Uani 1 1 d . . . C39 C 0.4749(4) 0.5010(4) 0.61264(18) 0.0515(9) Uani 1 1 d . . . H39A H 0.5772 0.5273 0.6290 0.062 Uiso 1 1 calc R . . C40 C 0.4277(4) 0.5630(4) 0.56934(18) 0.0549(9) Uani 1 1 d . . . H40A H 0.4967 0.6331 0.5567 0.066 Uiso 1 1 calc R . . N41 N 0.2858(4) 0.5262(3) 0.54453(16) 0.0591(8) Uani 1 1 d D . . H41 H 0.260(4) 0.573(3) 0.5176(14) 0.066(12) Uiso 1 1 d D . . C42 C 0.1870(5) 0.4266(5) 0.5609(2) 0.0778(14) Uani 1 1 d . . . H42A H 0.0869 0.4000 0.5420 0.093 Uiso 1 1 calc R . . C43 C 0.2296(4) 0.3628(4) 0.6047(2) 0.0690(12) Uani 1 1 d . . . H43A H 0.1584 0.2920 0.6158 0.083 Uiso 1 1 calc R . . C44 C 0.4639(4) 0.1303(4) 0.87540(16) 0.0451(8) Uani 1 1 d . . . C45 C 0.3947(4) 0.2212(4) 0.91085(16) 0.0458(8) Uani 1 1 d . . . H45A H 0.4107 0.3059 0.9021 0.055 Uiso 1 1 calc R . . C46 C 0.3022(4) 0.1852(3) 0.95893(16) 0.0449(8) Uani 1 1 d . . . H46A H 0.2541 0.2457 0.9830 0.054 Uiso 1 1 calc R . . C47 C 0.2794(4) 0.0622(4) 0.97229(17) 0.0485(9) Uani 1 1 d . . . H47A H 0.2174 0.0388 1.0057 0.058 Uiso 1 1 calc R . . C48 C 0.3470(4) -0.0250(4) 0.93686(19) 0.0546(10) Uani 1 1 d . . . H48A H 0.3298 -0.1100 0.9453 0.066 Uiso 1 1 calc R . . C49 C 0.4395(4) 0.0080(4) 0.88916(18) 0.0526(9) Uani 1 1 d . . . H49A H 0.4869 -0.0536 0.8656 0.063 Uiso 1 1 calc R . . C50 C 0.7142(4) 0.1434(3) 0.83267(16) 0.0446(8) Uani 1 1 d . . . C51 C 0.7847(4) 0.1585(3) 0.89207(17) 0.0467(8) Uani 1 1 d . . . H51A H 0.7363 0.1873 0.9291 0.056 Uiso 1 1 calc R . . C52 C 0.9250(4) 0.1315(3) 0.89711(17) 0.0485(9) Uani 1 1 d . . . H52A H 0.9728 0.1420 0.9378 0.058 Uiso 1 1 calc R . . C53 C 0.9971(4) 0.0896(3) 0.84411(18) 0.0489(9) Uani 1 1 d . . . H53A H 1.0935 0.0707 0.8482 0.059 Uiso 1 1 calc R . . C54 C 0.9281(4) 0.0754(4) 0.78519(19) 0.0534(9) Uani 1 1 d . . . H54A H 0.9775 0.0468 0.7484 0.064 Uiso 1 1 calc R . . C55 C 0.7870(4) 0.1024(4) 0.77893(18) 0.0513(9) Uani 1 1 d . . . H55A H 0.7404 0.0929 0.7381 0.062 Uiso 1 1 calc R . . Cl1 Cl 0.21591(11) 1.16996(11) 0.44144(5) 0.0668(3) Uani 1 1 d . . . Cl2 Cl 0.22134(11) 0.68355(11) 0.44849(5) 0.0678(3) Uani 1 1 d . . . O60 O 0.0865(4) 0.8712(3) 0.37254(16) 0.0886(10) Uani 1 1 d . . . C70 C 0.094(5) 0.339(3) 0.2944(8) 0.133(10) Uiso 0.181(3) 1 d PDU A 1 H70A H 0.0234 0.2545 0.2785 0.159 Uiso 0.181(3) 1 calc PR A 1 H70B H 0.1976 0.3320 0.2838 0.159 Uiso 0.181(3) 1 calc PR A 1 Cl3 Cl 0.0852(9) 0.3794(9) 0.3790(3) 0.0513(19) Uiso 0.181(3) 1 d PD A 1 Cl4 Cl 0.0426(8) 0.4598(8) 0.2545(3) 0.059(2) Uiso 0.181(3) 1 d PD A 1 C70' C 0.023(4) 0.477(3) 0.3308(16) 0.087(10) Uiso 0.174(4) 1 d PDU B 2 H70C H 0.0136 0.5316 0.3720 0.104 Uiso 0.174(4) 1 calc PR B 2 H70D H -0.0789 0.4174 0.3218 0.104 Uiso 0.174(4) 1 calc PR B 2 Cl3' Cl 0.1201(11) 0.3676(12) 0.3597(5) 0.064(3) Uiso 0.174(4) 1 d PD B 2 Cl4' Cl 0.002(3) 0.590(2) 0.2795(12) 0.280(12) Uiso 0.174(4) 1 d PD B 2 C70" C 0.002(4) 0.456(3) 0.3332(8) 0.039(6) Uiso 0.146(5) 1 d PDU C 3 H70E H 0.0459 0.5467 0.3533 0.047 Uiso 0.146(5) 1 calc PR C 3 H70F H -0.1090 0.4347 0.3371 0.047 Uiso 0.146(5) 1 calc PR C 3 Cl3" Cl 0.0913(14) 0.3462(12) 0.3649(7) 0.050(3) Uiso 0.146(5) 1 d PD C 3 Cl4" Cl 0.0532(10) 0.4210(11) 0.2512(4) 0.064(3) Uiso 0.146(5) 1 d PD C 3 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 0.0376(15) 0.0530(18) 0.0439(16) 0.0197(14) -0.0005(12) 0.0084(13) C2 0.0430(19) 0.046(2) 0.0366(18) 0.0092(15) 0.0005(14) 0.0112(15) C3 0.049(2) 0.062(2) 0.0401(19) 0.0175(17) 0.0049(16) 0.0160(18) C4 0.0366(19) 0.066(3) 0.055(2) 0.0246(19) 0.0050(16) 0.0146(17) C5 0.048(2) 0.053(2) 0.0389(19) 0.0123(16) 0.0023(15) 0.0137(17) C6 0.0419(19) 0.059(2) 0.0415(19) 0.0147(17) 0.0029(15) 0.0125(16) C7 0.0386(18) 0.056(2) 0.046(2) 0.0153(17) 0.0014(15) 0.0129(16) C8 0.044(2) 0.061(2) 0.0404(19) 0.0160(17) 0.0037(15) 0.0190(17) C9 0.048(2) 0.078(3) 0.051(2) 0.024(2) 0.0061(17) 0.0177(19) C10 0.044(2) 0.097(3) 0.052(2) 0.030(2) 0.0036(18) 0.023(2) N11 0.060(2) 0.073(2) 0.0432(17) 0.0262(17) 0.0051(15) 0.0265(18) C12 0.053(2) 0.066(3) 0.046(2) 0.0181(18) 0.0092(17) 0.0215(19) C13 0.046(2) 0.056(2) 0.046(2) 0.0169(17) 0.0044(16) 0.0164(17) C14 0.0356(18) 0.051(2) 0.0414(19) 0.0132(16) 0.0019(14) 0.0083(15) C15 0.046(2) 0.043(2) 0.051(2) 0.0102(16) -0.0032(16) 0.0105(16) C16 0.041(2) 0.052(2) 0.061(2) 0.0168(18) -0.0031(17) 0.0068(16) C17 0.0371(19) 0.064(3) 0.064(2) 0.023(2) 0.0014(17) 0.0159(18) C18 0.048(2) 0.057(2) 0.068(3) 0.028(2) 0.0091(18) 0.0191(18) C19 0.046(2) 0.044(2) 0.061(2) 0.0188(18) 0.0056(17) 0.0095(16) C20 0.0385(18) 0.049(2) 0.047(2) 0.0177(16) 0.0016(15) 0.0154(15) C21 0.044(2) 0.052(2) 0.043(2) 0.0100(16) -0.0015(15) 0.0093(16) C22 0.049(2) 0.061(2) 0.043(2) 0.0171(18) 0.0045(16) 0.0165(18) C23 0.045(2) 0.052(2) 0.064(2) 0.0276(19) 0.0129(18) 0.0167(17) C24 0.0415(19) 0.043(2) 0.063(2) 0.0134(18) 0.0015(17) 0.0102(16) C25 0.046(2) 0.045(2) 0.048(2) 0.0086(16) -0.0026(16) 0.0121(16) N31 0.0463(17) 0.074(2) 0.0418(16) 0.0193(15) 0.0053(13) 0.0239(15) C32 0.045(2) 0.055(2) 0.0385(18) 0.0101(16) 0.0059(15) 0.0136(17) C33 0.042(2) 0.065(3) 0.048(2) 0.0187(19) -0.0009(16) 0.0132(18) C34 0.048(2) 0.057(2) 0.051(2) 0.0162(18) 0.0058(17) 0.0136(17) C35 0.044(2) 0.052(2) 0.0397(18) 0.0095(16) 0.0048(15) 0.0154(16) C36 0.0388(19) 0.059(2) 0.047(2) 0.0115(17) 0.0036(15) 0.0160(16) C37 0.043(2) 0.062(2) 0.0430(19) 0.0165(17) 0.0080(16) 0.0136(17) C38 0.043(2) 0.056(2) 0.045(2) 0.0153(17) 0.0068(16) 0.0169(17) C39 0.046(2) 0.059(2) 0.054(2) 0.0194(19) 0.0033(17) 0.0132(18) C40 0.057(2) 0.055(2) 0.053(2) 0.0128(19) 0.0048(18) 0.0124(19) N41 0.059(2) 0.065(2) 0.062(2) 0.0285(18) 0.0068(17) 0.0206(17) C42 0.049(2) 0.103(4) 0.093(3) 0.054(3) -0.003(2) 0.014(2) C43 0.051(2) 0.078(3) 0.087(3) 0.045(3) -0.002(2) 0.011(2) C44 0.0391(19) 0.058(2) 0.0438(19) 0.0161(17) 0.0027(15) 0.0172(16) C45 0.0394(19) 0.055(2) 0.047(2) 0.0173(17) -0.0012(15) 0.0138(16) C46 0.0408(19) 0.057(2) 0.0392(19) 0.0092(16) 0.0029(15) 0.0167(16) C47 0.043(2) 0.059(2) 0.047(2) 0.0208(18) 0.0041(16) 0.0105(17) C48 0.051(2) 0.044(2) 0.071(3) 0.0184(19) 0.0047(19) 0.0087(17) C49 0.050(2) 0.049(2) 0.059(2) 0.0068(18) 0.0081(18) 0.0166(17) C50 0.0397(19) 0.051(2) 0.044(2) 0.0115(16) 0.0016(15) 0.0109(16) C51 0.045(2) 0.051(2) 0.045(2) 0.0132(16) 0.0046(16) 0.0100(16) C52 0.044(2) 0.053(2) 0.048(2) 0.0168(17) -0.0030(16) 0.0065(17) C53 0.0368(19) 0.049(2) 0.063(2) 0.0203(18) 0.0041(17) 0.0082(16) C54 0.045(2) 0.062(3) 0.056(2) 0.0165(19) 0.0073(17) 0.0137(18) C55 0.048(2) 0.060(2) 0.047(2) 0.0138(18) 0.0024(17) 0.0139(18) Cl1 0.0602(6) 0.0972(8) 0.0580(6) 0.0380(6) 0.0117(5) 0.0301(6) Cl2 0.0594(6) 0.0904(8) 0.0643(6) 0.0374(6) 0.0047(5) 0.0211(5) O60 0.079(2) 0.105(3) 0.088(2) 0.039(2) -0.0069(18) 0.0189(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.401(4) . ? N1 C20 1.428(4) . ? N1 C14 1.432(4) . ? C2 C7 1.398(5) . ? C2 C3 1.403(5) . ? C3 C4 1.377(5) . ? C4 C5 1.404(5) . ? C5 C6 1.397(5) . ? C5 C8 1.468(5) . ? C6 C7 1.375(5) . ? C8 C9 1.400(5) . ? C8 C13 1.401(5) . ? C9 C10 1.372(5) . ? C10 N11 1.343(5) . ? N11 C12 1.343(5) . ? C12 C13 1.365(5) . ? C14 C15 1.382(5) . ? C14 C19 1.389(5) . ? C15 C16 1.378(5) . ? C16 C17 1.390(5) . ? C17 C18 1.369(5) . ? C18 C19 1.380(5) . ? C20 C21 1.391(5) . ? C20 C25 1.404(5) . ? C21 C22 1.378(5) . ? C22 C23 1.386(5) . ? C23 C24 1.389(5) . ? C24 C25 1.385(5) . ? N31 C32 1.408(4) . ? N31 C44 1.429(4) . ? N31 C50 1.434(4) . ? C32 C33 1.381(5) . ? C32 C37 1.398(5) . ? C33 C34 1.388(5) . ? C34 C35 1.397(5) . ? C35 C36 1.394(5) . ? C35 C38 1.473(5) . ? C36 C37 1.396(5) . ? C38 C43 1.392(5) . ? C38 C39 1.394(5) . ? C39 C40 1.362(5) . ? C40 N41 1.332(5) . ? N41 C42 1.338(5) . ? C42 C43 1.367(5) . ? C44 C49 1.381(5) . ? C44 C45 1.403(5) . ? C45 C46 1.390(5) . ? C46 C47 1.385(5) . ? C47 C48 1.366(5) . ? C48 C49 1.375(5) . ? C50 C51 1.389(5) . ? C50 C55 1.389(5) . ? C51 C52 1.378(4) . ? C52 C53 1.376(5) . ? C53 C54 1.376(5) . ? C54 C55 1.387(5) . ? C70 Cl3 1.799(16) . ? C70 Cl4 1.826(16) . ? C70' Cl3' 1.818(14) . ? C70' Cl4' 1.831(15) . ? C70" Cl3" 1.804(14) . ? C70" Cl4" 1.820(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C20 121.0(3) . . ? C2 N1 C14 122.7(3) . . ? C20 N1 C14 116.2(2) . . ? C7 C2 N1 121.6(3) . . ? C7 C2 C3 118.0(3) . . ? N1 C2 C3 120.4(3) . . ? C4 C3 C2 120.6(3) . . ? C3 C4 C5 121.8(3) . . ? C6 C5 C4 116.7(3) . . ? C6 C5 C8 121.9(3) . . ? C4 C5 C8 121.4(3) . . ? C7 C6 C5 122.0(3) . . ? C6 C7 C2 120.8(3) . . ? C9 C8 C13 116.9(3) . . ? C9 C8 C5 121.2(3) . . ? C13 C8 C5 121.8(3) . . ? C10 C9 C8 120.0(4) . . ? N11 C10 C9 120.5(3) . . ? C10 N11 C12 121.7(3) . . ? N11 C12 C13 119.5(4) . . ? C12 C13 C8 121.3(3) . . ? C15 C14 C19 118.5(3) . . ? C15 C14 N1 122.5(3) . . ? C19 C14 N1 118.9(3) . . ? C16 C15 C14 120.5(3) . . ? C15 C16 C17 120.6(4) . . ? C18 C17 C16 119.0(3) . . ? C17 C18 C19 120.6(3) . . ? C18 C19 C14 120.8(3) . . ? C21 C20 C25 119.1(3) . . ? C21 C20 N1 119.7(3) . . ? C25 C20 N1 121.2(3) . . ? C22 C21 C20 120.8(3) . . ? C21 C22 C23 120.1(3) . . ? C22 C23 C24 120.0(3) . . ? C25 C24 C23 120.3(4) . . ? C24 C25 C20 119.8(3) . . ? C32 N31 C44 121.0(3) . . ? C32 N31 C50 122.2(3) . . ? C44 N31 C50 116.8(3) . . ? C33 C32 C37 117.9(3) . . ? C33 C32 N31 121.1(3) . . ? C37 C32 N31 120.9(3) . . ? C32 C33 C34 121.4(3) . . ? C33 C34 C35 121.2(3) . . ? C36 C35 C34 117.4(3) . . ? C36 C35 C38 121.9(3) . . ? C34 C35 C38 120.7(3) . . ? C35 C36 C37 121.1(3) . . ? C36 C37 C32 120.8(3) . . ? C43 C38 C39 116.0(3) . . ? C43 C38 C35 122.3(3) . . ? C39 C38 C35 121.7(3) . . ? C40 C39 C38 121.0(3) . . ? N41 C40 C39 120.7(4) . . ? C40 N41 C42 120.8(3) . . ? N41 C42 C43 120.2(4) . . ? C42 C43 C38 121.2(4) . . ? C49 C44 C45 119.5(3) . . ? C49 C44 N31 120.2(3) . . ? C45 C44 N31 120.2(3) . . ? C46 C45 C44 118.9(3) . . ? C47 C46 C45 120.9(3) . . ? C48 C47 C46 119.2(3) . . ? C47 C48 C49 121.2(3) . . ? C48 C49 C44 120.3(3) . . ? C51 C50 C55 119.5(3) . . ? C51 C50 N31 119.6(3) . . ? C55 C50 N31 120.9(3) . . ? C52 C51 C50 119.8(3) . . ? C53 C52 C51 121.1(3) . . ? C52 C53 C54 119.3(3) . . ? C53 C54 C55 120.6(3) . . ? C54 C55 C50 119.7(3) . . ? Cl3 C70 Cl4 112.3(13) . . ? Cl3' C70' Cl4' 153(2) . . ? Cl3" C70" Cl4" 98.9(10) . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 69.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.377 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.057 #===END