data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Ji-Young Shin' _publ_contact_author_email JIYOUNG@CHEM.UBC.CA _publ_section_title ; Facile synthesis of dicyanovinyl-di(meso-aryl) dipyrromethenes via a dipyrromethene-DDQ adduct ; loop_ _publ_author_name 'Ji-Young Shin' 'David Dolphin' 'Brian O. Patrick' # Attachment 'CIFs.txt' data_dd300 _database_code_depnum_ccdc_archive 'CCDC 708612' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H20 Cl8 N6 O2' _chemical_formula_weight 888.21 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' Cl Cl 0.1484 0.1585 '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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2796(18) _cell_length_b 12.066(2) _cell_length_c 14.734(2) _cell_angle_alpha 83.100(8) _cell_angle_beta 79.807(8) _cell_angle_gamma 89.782(8) _cell_volume 1959.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9982 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 28.10 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.619 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9356 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.00 _reflns_number_total 9356 _reflns_number_gt 6694 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1005P)^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 9356 _refine_ls_number_parameters 504 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1743 _refine_ls_wR_factor_gt 0.1628 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_restrained_S_all 1.172 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0185(3) 0.4463(3) 0.6204(2) 0.0307(7) Uani 1 1 d . . . H1 H 0.0802 0.4622 0.5675 0.037 Uiso 1 1 calc R . . C2 C -0.0460(3) 0.3465(3) 0.6455(2) 0.0312(7) Uani 1 1 d . . . H2 H -0.0374 0.2828 0.6130 0.037 Uiso 1 1 calc R . . C3 C -0.1255(3) 0.3573(2) 0.7273(2) 0.0265(6) Uani 1 1 d . . . H3 H -0.1813 0.3020 0.7613 0.032 Uiso 1 1 calc R . . C4 C -0.1080(2) 0.4659(2) 0.75080(19) 0.0210(6) Uani 1 1 d . . . C5 C -0.1652(2) 0.5171(2) 0.82766(17) 0.0181(5) Uani 1 1 d . . . C6 C -0.1350(2) 0.6223(2) 0.84730(17) 0.0181(5) Uani 1 1 d . . . C7 C -0.1843(2) 0.6773(2) 0.92642(18) 0.0213(6) Uani 1 1 d . . . H7 H -0.2470 0.6492 0.9757 0.026 Uiso 1 1 calc R . . C8 C -0.1248(2) 0.7772(2) 0.91790(19) 0.0221(6) Uani 1 1 d . . . H8 H -0.1367 0.8325 0.9592 0.027 Uiso 1 1 calc R . . C9 C -0.0403(2) 0.7801(2) 0.83275(18) 0.0189(5) Uani 1 1 d . . . C10 C -0.2667(2) 0.4527(2) 0.89133(18) 0.0184(5) Uani 1 1 d . . . C11 C -0.3811(3) 0.4466(2) 0.86831(19) 0.0231(6) Uani 1 1 d . . . C12 C -0.4753(3) 0.3874(3) 0.9247(2) 0.0294(7) Uani 1 1 d . . . H12 H -0.5514 0.3838 0.9059 0.035 Uiso 1 1 calc R . . C13 C -0.4577(3) 0.3328(3) 1.0097(2) 0.0330(7) Uani 1 1 d . . . H13 H -0.5226 0.2925 1.0498 0.040 Uiso 1 1 calc R . . C14 C -0.3465(3) 0.3368(3) 1.0362(2) 0.0289(7) Uani 1 1 d . . . H14 H -0.3346 0.2998 1.0945 0.035 Uiso 1 1 calc R . . C15 C -0.2528(2) 0.3955(2) 0.97702(18) 0.0205(6) Uani 1 1 d . . . C16 C 0.0478(2) 0.8761(2) 0.79010(18) 0.0188(5) Uani 1 1 d . . . C17 C -0.0287(2) 0.9771(2) 0.7624(2) 0.0243(6) Uani 1 1 d . . . C18 C -0.0782(3) 0.9715(2) 0.6758(2) 0.0252(6) Uani 1 1 d . . . C19 C -0.0412(2) 0.8946(2) 0.61671(19) 0.0210(6) Uani 1 1 d . . . C20 C 0.0596(2) 0.8183(2) 0.62887(17) 0.0186(5) Uani 1 1 d . . . C21 C 0.1334(2) 0.8449(2) 0.70253(17) 0.0159(5) Uani 1 1 d . . . C22 C 0.2189(2) 0.9413(2) 0.65764(17) 0.0164(5) Uani 1 1 d . . . C23 C 0.3172(2) 0.9373(2) 0.58182(18) 0.0197(5) Uani 1 1 d . . . H23 H 0.3414 0.8759 0.5486 0.024 Uiso 1 1 calc R . . C24 C 0.3686(2) 1.0431(2) 0.56790(18) 0.0199(5) Uani 1 1 d . . . H24 H 0.4366 1.0689 0.5226 0.024 Uiso 1 1 calc R . . C25 C 0.3002(2) 1.1065(2) 0.63449(17) 0.0168(5) Uani 1 1 d . . . C26 C 0.3242(2) 1.2151(2) 0.65059(17) 0.0161(5) Uani 1 1 d . . . C27 C 0.2574(2) 1.2713(2) 0.71998(18) 0.0192(5) Uani 1 1 d . . . C28 C 0.2706(3) 1.3815(2) 0.74136(19) 0.0252(6) Uani 1 1 d . . . H28 H 0.3308 1.4347 0.7106 0.030 Uiso 1 1 calc R . . C29 C 0.1798(3) 1.3979(3) 0.8154(2) 0.0311(7) Uani 1 1 d . . . H29 H 0.1657 1.4641 0.8442 0.037 Uiso 1 1 calc R . . C30 C 0.1138(3) 1.2988(3) 0.83886(19) 0.0277(6) Uani 1 1 d . . . H30 H 0.0463 1.2857 0.8877 0.033 Uiso 1 1 calc R . . C31 C 0.4320(2) 1.2752(2) 0.59208(18) 0.0178(5) Uani 1 1 d . . . C32 C 0.5426(3) 1.2751(2) 0.62311(19) 0.0219(6) Uani 1 1 d . . . C33 C 0.6450(3) 1.3262(3) 0.5677(2) 0.0269(6) Uani 1 1 d . . . H33 H 0.7189 1.3257 0.5903 0.032 Uiso 1 1 calc R . . C34 C 0.6390(3) 1.3775(3) 0.4801(2) 0.0276(6) Uani 1 1 d . . . H34 H 0.7093 1.4107 0.4414 0.033 Uiso 1 1 calc R . . C35 C 0.5312(3) 1.3808(2) 0.4485(2) 0.0269(6) Uani 1 1 d . . . H35 H 0.5268 1.4171 0.3884 0.032 Uiso 1 1 calc R . . C36 C 0.4295(2) 1.3314(2) 0.50446(18) 0.0204(6) Uani 1 1 d . . . C37 C 0.2054(2) 0.7453(2) 0.72567(17) 0.0184(5) Uani 1 1 d . . . C38 C 0.1152(3) 0.9059(2) 0.8617(2) 0.0265(6) Uani 1 1 d . . . C39 C 0.5510(4) 0.8486(5) 0.7134(3) 0.0712(14) Uani 1 1 d . . . H39A H 0.5140 0.7838 0.6930 0.085 Uiso 1 1 calc R . . H39B H 0.5791 0.9026 0.6577 0.085 Uiso 1 1 calc R . . N1 N -0.0199(2) 0.5165(2) 0.68244(17) 0.0247(5) Uani 1 1 d . . . N2 N -0.0451(2) 0.69053(18) 0.79017(15) 0.0187(5) Uani 1 1 d . . . N3 N 0.1635(3) 0.9248(3) 0.9194(2) 0.0471(8) Uani 1 1 d . . . N4 N 0.2665(2) 0.6719(2) 0.74085(17) 0.0280(6) Uani 1 1 d . . . N5 N 0.20662(19) 1.04010(17) 0.68820(15) 0.0165(4) Uani 1 1 d . . . N6 N 0.1597(2) 1.2242(2) 0.78230(16) 0.0216(5) Uani 1 1 d . . . Cl1 Cl -0.40480(7) 0.51502(7) 0.76243(5) 0.0372(2) Uani 1 1 d . . . Cl2 Cl -0.11255(6) 0.39523(6) 1.01030(4) 0.02438(17) Uani 1 1 d . . . Cl3 Cl -0.18643(8) 1.06554(7) 0.65713(7) 0.0425(2) Uani 1 1 d . . . Cl4 Cl -0.10520(7) 0.88278(6) 0.52249(5) 0.0331(2) Uani 1 1 d . . . Cl5 Cl 0.55248(7) 1.20855(7) 0.73178(5) 0.0338(2) Uani 1 1 d . . . Cl6 Cl 0.29428(7) 1.34035(6) 0.46339(5) 0.03126(19) Uani 1 1 d . . . Cl7 Cl 0.67271(10) 0.80439(10) 0.76231(9) 0.0687(3) Uani 1 1 d . . . Cl8 Cl 0.44181(10) 0.91148(9) 0.78934(8) 0.0566(3) Uani 1 1 d . . . O1 O 0.08899(18) 0.74729(16) 0.57824(13) 0.0245(4) Uani 1 1 d . . . O2 O -0.0556(2) 1.04965(17) 0.81141(16) 0.0344(5) Uani 1 1 d . . . H6N H 0.137(3) 1.161(3) 0.783(2) 0.033(10) Uiso 1 1 d . . . H1N H 0.014(3) 0.571(3) 0.686(2) 0.032(10) 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 C1 0.0299(17) 0.0333(17) 0.0274(15) -0.0094(13) 0.0028(13) -0.0008(13) C2 0.0349(18) 0.0281(16) 0.0323(16) -0.0144(13) -0.0032(13) -0.0016(13) C3 0.0275(16) 0.0213(14) 0.0304(15) -0.0046(12) -0.0030(12) -0.0079(12) C4 0.0196(14) 0.0205(13) 0.0215(13) 0.0006(11) -0.0021(11) -0.0031(11) C5 0.0177(13) 0.0185(13) 0.0173(12) 0.0026(10) -0.0040(10) -0.0005(10) C6 0.0146(13) 0.0203(13) 0.0175(12) 0.0017(10) -0.0003(10) -0.0042(10) C7 0.0192(14) 0.0233(14) 0.0185(13) -0.0005(11) 0.0031(10) -0.0032(11) C8 0.0211(14) 0.0228(14) 0.0205(13) -0.0029(11) 0.0020(11) -0.0051(11) C9 0.0163(13) 0.0191(13) 0.0196(13) 0.0018(10) -0.0014(10) -0.0055(10) C10 0.0176(13) 0.0166(13) 0.0194(12) 0.0005(10) -0.0003(10) -0.0052(10) C11 0.0237(15) 0.0247(14) 0.0205(13) 0.0035(11) -0.0068(11) -0.0034(11) C12 0.0200(15) 0.0355(17) 0.0310(16) 0.0023(13) -0.0035(12) -0.0112(12) C13 0.0268(16) 0.0372(18) 0.0297(16) 0.0088(13) 0.0008(13) -0.0163(14) C14 0.0299(16) 0.0310(16) 0.0224(14) 0.0061(12) -0.0016(12) -0.0054(13) C15 0.0202(14) 0.0207(13) 0.0200(13) -0.0003(11) -0.0037(11) 0.0000(11) C16 0.0187(13) 0.0173(13) 0.0186(12) -0.0027(10) 0.0019(10) -0.0035(10) C17 0.0178(14) 0.0182(14) 0.0325(15) -0.0022(12) 0.0070(12) -0.0049(11) C18 0.0195(14) 0.0190(14) 0.0348(16) 0.0038(12) -0.0026(12) -0.0022(11) C19 0.0190(14) 0.0175(13) 0.0250(14) 0.0042(11) -0.0046(11) -0.0057(10) C20 0.0193(13) 0.0163(13) 0.0178(12) 0.0036(10) -0.0004(10) -0.0059(10) C21 0.0149(12) 0.0135(12) 0.0173(12) -0.0001(10) 0.0010(10) -0.0006(10) C22 0.0149(12) 0.0139(12) 0.0196(12) -0.0010(10) -0.0016(10) -0.0017(10) C23 0.0208(14) 0.0132(12) 0.0224(13) -0.0033(10) 0.0043(11) -0.0020(10) C24 0.0183(13) 0.0166(13) 0.0220(13) -0.0030(10) 0.0044(10) -0.0016(10) C25 0.0140(12) 0.0160(12) 0.0184(12) 0.0009(10) 0.0008(10) -0.0018(10) C26 0.0144(12) 0.0147(12) 0.0185(12) 0.0004(10) -0.0024(10) -0.0018(10) C27 0.0221(14) 0.0166(13) 0.0180(12) -0.0004(10) -0.0018(10) -0.0014(10) C28 0.0326(16) 0.0172(14) 0.0257(14) -0.0053(11) -0.0028(12) -0.0035(12) C29 0.0421(19) 0.0249(15) 0.0266(15) -0.0128(12) -0.0005(13) 0.0065(13) C30 0.0286(16) 0.0309(16) 0.0216(14) -0.0076(12) 0.0036(12) 0.0030(13) C31 0.0185(13) 0.0132(12) 0.0201(12) -0.0051(10) 0.0030(10) -0.0028(10) C32 0.0225(14) 0.0193(13) 0.0227(13) -0.0022(11) -0.0011(11) -0.0003(11) C33 0.0167(14) 0.0280(15) 0.0358(16) -0.0056(13) -0.0026(12) -0.0050(12) C34 0.0235(15) 0.0273(15) 0.0285(15) -0.0043(12) 0.0061(12) -0.0093(12) C35 0.0292(16) 0.0281(15) 0.0208(13) -0.0023(12) 0.0022(12) -0.0087(12) C36 0.0221(14) 0.0179(13) 0.0207(13) -0.0032(10) -0.0016(11) -0.0058(11) C37 0.0194(13) 0.0160(13) 0.0179(12) 0.0001(10) 0.0008(10) -0.0043(11) C38 0.0271(15) 0.0267(15) 0.0232(14) -0.0057(12) 0.0040(12) -0.0089(12) C39 0.053(3) 0.105(4) 0.060(3) -0.019(3) -0.016(2) -0.007(3) N1 0.0252(13) 0.0238(13) 0.0227(12) -0.0033(10) 0.0026(10) -0.0067(11) N2 0.0173(11) 0.0196(11) 0.0177(10) -0.0013(9) 0.0001(9) -0.0032(9) N3 0.0507(19) 0.061(2) 0.0308(15) -0.0134(14) -0.0054(14) -0.0235(16) N4 0.0307(14) 0.0237(13) 0.0285(13) -0.0003(10) -0.0044(11) 0.0020(11) N5 0.0156(11) 0.0142(10) 0.0185(10) -0.0004(8) -0.0004(8) -0.0021(8) N6 0.0223(12) 0.0193(12) 0.0209(12) -0.0042(10) 0.0040(9) -0.0026(10) Cl1 0.0309(4) 0.0471(5) 0.0324(4) 0.0139(3) -0.0151(3) -0.0098(3) Cl2 0.0218(3) 0.0304(4) 0.0214(3) -0.0022(3) -0.0058(3) 0.0018(3) Cl3 0.0297(4) 0.0262(4) 0.0719(6) -0.0011(4) -0.0136(4) 0.0086(3) Cl4 0.0318(4) 0.0323(4) 0.0377(4) 0.0042(3) -0.0184(3) -0.0081(3) Cl5 0.0272(4) 0.0401(4) 0.0328(4) 0.0076(3) -0.0098(3) -0.0007(3) Cl6 0.0281(4) 0.0372(4) 0.0278(4) 0.0061(3) -0.0100(3) -0.0108(3) Cl7 0.0444(6) 0.0705(8) 0.0860(8) 0.0166(6) -0.0147(6) -0.0022(5) Cl8 0.0568(6) 0.0512(6) 0.0631(6) -0.0030(5) -0.0168(5) 0.0029(5) O1 0.0299(11) 0.0213(10) 0.0216(10) -0.0041(8) -0.0014(8) -0.0020(8) O2 0.0311(12) 0.0251(11) 0.0435(13) -0.0131(10) 0.0087(10) -0.0004(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 C1 N1 1.336(4) . ? C1 C2 1.386(4) . ? C1 H1 0.9500 . ? C2 C3 1.388(4) . ? C2 H2 0.9500 . ? C3 C4 1.418(4) . ? C3 H3 0.9500 . ? C4 N1 1.370(4) . ? C4 C5 1.409(4) . ? C5 C6 1.392(4) . ? C5 C10 1.499(4) . ? C6 N2 1.397(3) . ? C6 C7 1.436(4) . ? C7 C8 1.364(4) . ? C7 H7 0.9500 . ? C8 C9 1.432(4) . ? C8 H8 0.9500 . ? C9 N2 1.319(3) . ? C9 C16 1.529(4) . ? C10 C11 1.396(4) . ? C10 C15 1.398(4) . ? C11 C12 1.371(4) . ? C11 Cl1 1.739(3) . ? C12 C13 1.389(4) . ? C12 H12 0.9500 . ? C13 C14 1.381(4) . ? C13 H13 0.9500 . ? C14 C15 1.382(4) . ? C14 H14 0.9500 . ? C15 Cl2 1.737(3) . ? C16 C38 1.483(4) . ? C16 C17 1.548(4) . ? C16 C21 1.553(4) . ? C17 O2 1.205(3) . ? C17 C18 1.489(4) . ? C18 C19 1.362(4) . ? C18 Cl3 1.699(3) . ? C19 C20 1.483(4) . ? C19 Cl4 1.694(3) . ? C20 O1 1.210(3) . ? C20 C21 1.542(4) . ? C21 C37 1.487(4) . ? C21 C22 1.523(4) . ? C22 N5 1.322(3) . ? C22 C23 1.433(4) . ? C23 C24 1.381(4) . ? C23 H23 0.9500 . ? C24 C25 1.432(4) . ? C24 H24 0.9500 . ? C25 N5 1.393(3) . ? C25 C26 1.396(3) . ? C26 C27 1.401(4) . ? C26 C31 1.494(3) . ? C27 N6 1.379(4) . ? C27 C28 1.417(4) . ? C28 C29 1.390(4) . ? C28 H28 0.9500 . ? C29 C30 1.385(4) . ? C29 H29 0.9500 . ? C30 N6 1.340(4) . ? C30 H30 0.9500 . ? C31 C36 1.389(4) . ? C31 C32 1.402(4) . ? C32 C33 1.390(4) . ? C32 Cl5 1.725(3) . ? C33 C34 1.376(4) . ? C33 H33 0.9500 . ? C34 C35 1.375(4) . ? C34 H34 0.9500 . ? C35 C36 1.380(4) . ? C35 H35 0.9500 . ? C36 Cl6 1.736(3) . ? C37 N4 1.145(4) . ? C38 N3 1.133(4) . ? C39 Cl7 1.714(5) . ? C39 Cl8 1.748(5) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? N1 H1N 0.77(4) . ? N6 H6N 0.80(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 N1 C1 C2 109.2(3) . . ? N1 C1 H1 125.4 . . ? C2 C1 H1 125.4 . . ? C1 C2 C3 107.0(3) . . ? C1 C2 H2 126.5 . . ? C3 C2 H2 126.5 . . ? C2 C3 C4 107.4(3) . . ? C2 C3 H3 126.3 . . ? C4 C3 H3 126.3 . . ? N1 C4 C5 124.0(3) . . ? N1 C4 C3 106.3(2) . . ? C5 C4 C3 129.7(3) . . ? C6 C5 C4 124.8(2) . . ? C6 C5 C10 118.5(2) . . ? C4 C5 C10 116.7(2) . . ? C5 C6 N2 122.8(2) . . ? C5 C6 C7 128.0(2) . . ? N2 C6 C7 109.2(2) . . ? C8 C7 C6 107.5(2) . . ? C8 C7 H7 126.3 . . ? C6 C7 H7 126.3 . . ? C7 C8 C9 104.6(2) . . ? C7 C8 H8 127.7 . . ? C9 C8 H8 127.7 . . ? N2 C9 C8 113.8(2) . . ? N2 C9 C16 120.6(2) . . ? C8 C9 C16 125.7(2) . . ? C11 C10 C15 116.0(2) . . ? C11 C10 C5 121.7(2) . . ? C15 C10 C5 122.3(2) . . ? C12 C11 C10 123.0(3) . . ? C12 C11 Cl1 118.4(2) . . ? C10 C11 Cl1 118.6(2) . . ? C11 C12 C13 119.0(3) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.2(3) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C14 C15 C10 122.4(3) . . ? C14 C15 Cl2 118.3(2) . . ? C10 C15 Cl2 119.3(2) . . ? C38 C16 C9 108.9(2) . . ? C38 C16 C17 108.4(2) . . ? C9 C16 C17 106.9(2) . . ? C38 C16 C21 111.9(2) . . ? C9 C16 C21 111.0(2) . . ? C17 C16 C21 109.5(2) . . ? O2 C17 C18 122.2(3) . . ? O2 C17 C16 122.6(3) . . ? C18 C17 C16 114.9(2) . . ? C19 C18 C17 122.3(3) . . ? C19 C18 Cl3 122.3(2) . . ? C17 C18 Cl3 115.4(2) . . ? C18 C19 C20 122.4(2) . . ? C18 C19 Cl4 121.9(2) . . ? C20 C19 Cl4 115.7(2) . . ? O1 C20 C19 122.0(2) . . ? O1 C20 C21 122.3(2) . . ? C19 C20 C21 115.3(2) . . ? C37 C21 C22 109.0(2) . . ? C37 C21 C20 108.3(2) . . ? C22 C21 C20 106.7(2) . . ? C37 C21 C16 111.2(2) . . ? C22 C21 C16 111.5(2) . . ? C20 C21 C16 110.0(2) . . ? N5 C22 C23 113.5(2) . . ? N5 C22 C21 120.5(2) . . ? C23 C22 C21 126.0(2) . . ? C24 C23 C22 104.4(2) . . ? C24 C23 H23 127.8 . . ? C22 C23 H23 127.8 . . ? C23 C24 C25 107.2(2) . . ? C23 C24 H24 126.4 . . ? C25 C24 H24 126.4 . . ? N5 C25 C26 123.0(2) . . ? N5 C25 C24 109.4(2) . . ? C26 C25 C24 127.4(2) . . ? C25 C26 C27 125.0(2) . . ? C25 C26 C31 117.9(2) . . ? C27 C26 C31 117.1(2) . . ? N6 C27 C26 123.5(2) . . ? N6 C27 C28 106.3(2) . . ? C26 C27 C28 130.2(3) . . ? C29 C28 C27 107.8(3) . . ? C29 C28 H28 126.1 . . ? C27 C28 H28 126.1 . . ? C30 C29 C28 106.7(2) . . ? C30 C29 H29 126.7 . . ? C28 C29 H29 126.7 . . ? N6 C30 C29 109.7(3) . . ? N6 C30 H30 125.1 . . ? C29 C30 H30 125.1 . . ? C36 C31 C32 116.6(2) . . ? C36 C31 C26 122.6(2) . . ? C32 C31 C26 120.8(2) . . ? C33 C32 C31 121.5(3) . . ? C33 C32 Cl5 119.1(2) . . ? C31 C32 Cl5 119.4(2) . . ? C34 C33 C32 119.7(3) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C35 C34 C33 120.0(3) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C34 C35 C36 119.9(3) . . ? C34 C35 H35 120.1 . . ? C36 C35 H35 120.1 . . ? C35 C36 C31 122.2(3) . . ? C35 C36 Cl6 118.6(2) . . ? C31 C36 Cl6 119.3(2) . . ? N4 C37 C21 176.1(3) . . ? N3 C38 C16 176.6(3) . . ? Cl7 C39 Cl8 113.1(3) . . ? Cl7 C39 H39A 109.0 . . ? Cl8 C39 H39A 109.0 . . ? Cl7 C39 H39B 109.0 . . ? Cl8 C39 H39B 109.0 . . ? H39A C39 H39B 107.8 . . ? C1 N1 C4 110.1(3) . . ? C1 N1 H1N 124(3) . . ? C4 N1 H1N 124(3) . . ? C9 N2 C6 105.0(2) . . ? C22 N5 C25 105.4(2) . . ? C30 N6 C27 109.5(2) . . ? C30 N6 H6N 128(3) . . ? C27 N6 H6N 123(3) . . ? 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 N1 C1 C2 C3 -0.9(4) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C2 C3 C4 N1 0.5(3) . . . . ? C2 C3 C4 C5 -179.1(3) . . . . ? N1 C4 C5 C6 -4.1(4) . . . . ? C3 C4 C5 C6 175.4(3) . . . . ? N1 C4 C5 C10 175.0(3) . . . . ? C3 C4 C5 C10 -5.4(4) . . . . ? C4 C5 C6 N2 1.8(4) . . . . ? C10 C5 C6 N2 -177.4(2) . . . . ? C4 C5 C6 C7 -176.3(3) . . . . ? C10 C5 C6 C7 4.5(4) . . . . ? C5 C6 C7 C8 177.9(3) . . . . ? N2 C6 C7 C8 -0.4(3) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? C7 C8 C9 N2 0.2(3) . . . . ? C7 C8 C9 C16 178.9(3) . . . . ? C6 C5 C10 C11 101.5(3) . . . . ? C4 C5 C10 C11 -77.7(3) . . . . ? C6 C5 C10 C15 -78.4(3) . . . . ? C4 C5 C10 C15 102.4(3) . . . . ? C15 C10 C11 C12 -0.7(4) . . . . ? C5 C10 C11 C12 179.3(3) . . . . ? C15 C10 C11 Cl1 -179.6(2) . . . . ? C5 C10 C11 Cl1 0.5(4) . . . . ? C10 C11 C12 C13 1.5(5) . . . . ? Cl1 C11 C12 C13 -179.7(2) . . . . ? C11 C12 C13 C14 -0.9(5) . . . . ? C12 C13 C14 C15 -0.3(5) . . . . ? C13 C14 C15 C10 1.0(5) . . . . ? C13 C14 C15 Cl2 -177.8(2) . . . . ? C11 C10 C15 C14 -0.5(4) . . . . ? C5 C10 C15 C14 179.4(3) . . . . ? C11 C10 C15 Cl2 178.3(2) . . . . ? C5 C10 C15 Cl2 -1.8(4) . . . . ? N2 C9 C16 C38 -130.4(3) . . . . ? C8 C9 C16 C38 51.0(4) . . . . ? N2 C9 C16 C17 112.7(3) . . . . ? C8 C9 C16 C17 -66.0(3) . . . . ? N2 C9 C16 C21 -6.7(3) . . . . ? C8 C9 C16 C21 174.6(2) . . . . ? C38 C16 C17 O2 -20.8(4) . . . . ? C9 C16 C17 O2 96.5(3) . . . . ? C21 C16 C17 O2 -143.2(3) . . . . ? C38 C16 C17 C18 165.8(2) . . . . ? C9 C16 C17 C18 -76.9(3) . . . . ? C21 C16 C17 C18 43.4(3) . . . . ? O2 C17 C18 C19 175.1(3) . . . . ? C16 C17 C18 C19 -11.5(4) . . . . ? O2 C17 C18 Cl3 -6.5(4) . . . . ? C16 C17 C18 Cl3 167.00(19) . . . . ? C17 C18 C19 C20 -6.4(4) . . . . ? Cl3 C18 C19 C20 175.2(2) . . . . ? C17 C18 C19 Cl4 175.5(2) . . . . ? Cl3 C18 C19 Cl4 -2.9(4) . . . . ? C18 C19 C20 O1 177.1(3) . . . . ? Cl4 C19 C20 O1 -4.7(3) . . . . ? C18 C19 C20 C21 -9.9(4) . . . . ? Cl4 C19 C20 C21 168.34(18) . . . . ? O1 C20 C21 C37 -23.2(3) . . . . ? C19 C20 C21 C37 163.8(2) . . . . ? O1 C20 C21 C22 94.0(3) . . . . ? C19 C20 C21 C22 -79.0(3) . . . . ? O1 C20 C21 C16 -144.9(2) . . . . ? C19 C20 C21 C16 42.1(3) . . . . ? C38 C16 C21 C37 61.9(3) . . . . ? C9 C16 C21 C37 -60.1(3) . . . . ? C17 C16 C21 C37 -177.9(2) . . . . ? C38 C16 C21 C22 -59.9(3) . . . . ? C9 C16 C21 C22 178.1(2) . . . . ? C17 C16 C21 C22 60.4(3) . . . . ? C38 C16 C21 C20 -178.1(2) . . . . ? C9 C16 C21 C20 59.9(3) . . . . ? C17 C16 C21 C20 -57.9(3) . . . . ? C37 C21 C22 N5 -129.6(2) . . . . ? C20 C21 C22 N5 113.6(3) . . . . ? C16 C21 C22 N5 -6.6(3) . . . . ? C37 C21 C22 C23 50.2(3) . . . . ? C20 C21 C22 C23 -66.6(3) . . . . ? C16 C21 C22 C23 173.2(2) . . . . ? N5 C22 C23 C24 1.2(3) . . . . ? C21 C22 C23 C24 -178.6(2) . . . . ? C22 C23 C24 C25 -0.3(3) . . . . ? C23 C24 C25 N5 -0.6(3) . . . . ? C23 C24 C25 C26 175.1(3) . . . . ? N5 C25 C26 C27 -1.4(4) . . . . ? C24 C25 C26 C27 -176.7(3) . . . . ? N5 C25 C26 C31 176.1(2) . . . . ? C24 C25 C26 C31 0.9(4) . . . . ? C25 C26 C27 N6 1.0(4) . . . . ? C31 C26 C27 N6 -176.5(2) . . . . ? C25 C26 C27 C28 -178.0(3) . . . . ? C31 C26 C27 C28 4.4(4) . . . . ? N6 C27 C28 C29 -0.5(3) . . . . ? C26 C27 C28 C29 178.6(3) . . . . ? C27 C28 C29 C30 0.7(3) . . . . ? C28 C29 C30 N6 -0.5(4) . . . . ? C25 C26 C31 C36 83.7(3) . . . . ? C27 C26 C31 C36 -98.6(3) . . . . ? C25 C26 C31 C32 -95.0(3) . . . . ? C27 C26 C31 C32 82.7(3) . . . . ? C36 C31 C32 C33 -1.7(4) . . . . ? C26 C31 C32 C33 177.0(2) . . . . ? C36 C31 C32 Cl5 179.2(2) . . . . ? C26 C31 C32 Cl5 -2.1(3) . . . . ? C31 C32 C33 C34 -0.5(4) . . . . ? Cl5 C32 C33 C34 178.6(2) . . . . ? C32 C33 C34 C35 1.8(5) . . . . ? C33 C34 C35 C36 -0.8(4) . . . . ? C34 C35 C36 C31 -1.6(4) . . . . ? C34 C35 C36 Cl6 178.4(2) . . . . ? C32 C31 C36 C35 2.8(4) . . . . ? C26 C31 C36 C35 -175.9(2) . . . . ? C32 C31 C36 Cl6 -177.2(2) . . . . ? C26 C31 C36 Cl6 4.1(4) . . . . ? C2 C1 N1 C4 1.2(4) . . . . ? C5 C4 N1 C1 178.6(3) . . . . ? C3 C4 N1 C1 -1.0(3) . . . . ? C8 C9 N2 C6 -0.4(3) . . . . ? C16 C9 N2 C6 -179.2(2) . . . . ? C5 C6 N2 C9 -177.9(2) . . . . ? C7 C6 N2 C9 0.5(3) . . . . ? C23 C22 N5 C25 -1.6(3) . . . . ? C21 C22 N5 C25 178.2(2) . . . . ? C26 C25 N5 C22 -174.6(2) . . . . ? C24 C25 N5 C22 1.4(3) . . . . ? C29 C30 N6 C27 0.2(3) . . . . ? C26 C27 N6 C30 -179.0(3) . . . . ? C28 C27 N6 C30 0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.956 _refine_diff_density_min -1.384 _refine_diff_density_rms 0.090 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 1.000 0.000 155 41 ' ' _platon_squeeze_details ; ; #===END data_dd301 _database_code_depnum_ccdc_archive 'CCDC 710025' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H18 Cl4 N6' _chemical_formula_weight 652.34 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' 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 'P 21/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 14.1530(16) _cell_length_b 10.3574(11) _cell_length_c 20.116(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.535(5) _cell_angle_gamma 90.00 _cell_volume 2945.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9827 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 27.66 _exptl_crystal_description irregular _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.439 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.868 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 61182 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.00 _reflns_number_total 7054 _reflns_number_gt 5367 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0314P)^2^+1.6638P] 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 7054 _refine_ls_number_parameters 405 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0821 _refine_ls_wR_factor_gt 0.0725 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.56806(12) 0.34198(16) 0.54630(8) 0.0269(4) Uani 1 1 d . . . H1 H 0.6225 0.3861 0.5323 0.032 Uiso 1 1 calc R . . C2 C 0.48146(12) 0.33507(16) 0.51130(8) 0.0292(4) Uani 1 1 d . . . H2 H 0.4660 0.3734 0.4693 0.035 Uiso 1 1 calc R . . C3 C 0.42143(11) 0.26152(16) 0.54911(8) 0.0254(3) Uani 1 1 d . . . H3 H 0.3575 0.2405 0.5375 0.031 Uiso 1 1 calc R . . C4 C 0.47220(10) 0.22394(15) 0.60752(8) 0.0206(3) Uani 1 1 d . . . C5 C 0.44306(10) 0.14938(15) 0.66187(8) 0.0204(3) Uani 1 1 d . . . C6 C 0.49905(10) 0.12187(15) 0.71848(8) 0.0211(3) Uani 1 1 d . . . C7 C 0.47464(11) 0.04931(16) 0.77664(8) 0.0241(3) Uani 1 1 d . . . H7 H 0.4158 0.0085 0.7838 0.029 Uiso 1 1 calc R . . C8 C 0.55192(11) 0.05076(16) 0.81898(8) 0.0240(3) Uani 1 1 d . . . H8 H 0.5580 0.0125 0.8619 0.029 Uiso 1 1 calc R . . C9 C 0.62343(10) 0.12299(15) 0.78511(8) 0.0201(3) Uani 1 1 d . . . C10 C 0.34359(10) 0.09940(15) 0.65551(8) 0.0202(3) Uani 1 1 d . . . C11 C 0.32021(11) -0.01125(16) 0.61832(8) 0.0247(3) Uani 1 1 d . . . C12 C 0.22763(11) -0.05287(17) 0.60830(9) 0.0288(4) Uani 1 1 d . . . H12 H 0.2137 -0.1270 0.5818 0.035 Uiso 1 1 calc R . . C13 C 0.15593(11) 0.01426(17) 0.63715(9) 0.0298(4) Uani 1 1 d . . . H13 H 0.0924 -0.0144 0.6308 0.036 Uiso 1 1 calc R . . C14 C 0.17561(11) 0.12285(16) 0.67519(9) 0.0274(4) Uani 1 1 d . . . H14 H 0.1263 0.1678 0.6959 0.033 Uiso 1 1 calc R . . C15 C 0.26836(11) 0.16539(15) 0.68277(8) 0.0225(3) Uani 1 1 d . . . C16 C 0.72038(10) 0.14669(15) 0.80992(8) 0.0208(3) Uani 1 1 d . . . C17 C 0.74053(11) 0.10534(16) 0.87780(8) 0.0246(3) Uani 1 1 d . . . C18 C 0.78994(10) 0.20459(15) 0.77432(8) 0.0216(3) Uani 1 1 d . . . C19 C 0.76910(10) 0.25065(16) 0.70746(8) 0.0237(3) Uani 1 1 d . . . C20 C 0.88725(11) 0.23282(16) 0.79666(8) 0.0226(3) Uani 1 1 d . . . C21 C 0.95496(11) 0.29779(19) 0.75652(8) 0.0309(4) Uani 1 1 d . . . H21 H 0.9460 0.3241 0.7114 0.037 Uiso 1 1 calc R . . C22 C 1.03409(11) 0.31345(18) 0.79652(8) 0.0286(4) Uani 1 1 d . . . H22 H 1.0916 0.3533 0.7850 0.034 Uiso 1 1 calc R . . C23 C 1.01341(10) 0.25769(15) 0.85984(8) 0.0214(3) Uani 1 1 d . . . C24 C 1.07231(10) 0.25682(14) 0.91728(8) 0.0194(3) Uani 1 1 d . . . C25 C 1.04772(10) 0.20542(14) 0.97885(8) 0.0202(3) Uani 1 1 d . . . C26 C 1.10171(11) 0.19303(16) 1.03894(8) 0.0255(3) Uani 1 1 d . . . H26 H 1.1655 0.2196 1.0465 0.031 Uiso 1 1 calc R . . C27 C 1.04556(12) 0.13531(17) 1.08513(8) 0.0288(4) Uani 1 1 d . . . H27 H 1.0638 0.1146 1.1299 0.035 Uiso 1 1 calc R . . C28 C 0.95725(12) 0.11322(16) 1.05371(8) 0.0261(4) Uani 1 1 d . . . H28 H 0.9044 0.0752 1.0737 0.031 Uiso 1 1 calc R . . C29 C 1.16779(10) 0.31960(15) 0.91382(7) 0.0201(3) Uani 1 1 d . . . C30 C 1.24786(11) 0.25255(15) 0.89514(8) 0.0225(3) Uani 1 1 d . . . C31 C 1.33521(11) 0.31206(17) 0.89042(8) 0.0278(4) Uani 1 1 d . . . H31 H 1.3882 0.2643 0.8767 0.033 Uiso 1 1 calc R . . C32 C 1.34417(11) 0.44209(18) 0.90603(9) 0.0323(4) Uani 1 1 d . . . H32 H 1.4039 0.4832 0.9036 0.039 Uiso 1 1 calc R . . C33 C 1.26707(11) 0.51204(17) 0.92510(9) 0.0297(4) Uani 1 1 d . . . H33 H 1.2734 0.6010 0.9360 0.036 Uiso 1 1 calc R . . C34 C 1.18021(11) 0.45088(16) 0.92811(8) 0.0243(3) Uani 1 1 d . . . N1 N 0.56179(10) 0.27578(13) 0.60330(7) 0.0229(3) Uani 1 1 d . . . N2 N 0.59191(9) 0.16545(13) 0.72587(6) 0.0216(3) Uani 1 1 d . . . N3 N 0.74877(10) 0.07236(16) 0.93229(8) 0.0351(4) Uani 1 1 d . . . N4 N 0.76415(10) 0.29410(15) 0.65469(7) 0.0328(3) Uani 1 1 d . . . N5 N 0.92219(8) 0.20791(12) 0.85801(6) 0.0205(3) Uani 1 1 d . . . N6 N 0.95908(9) 0.15436(13) 0.99074(7) 0.0218(3) Uani 1 1 d . . . Cl1 Cl 0.40860(3) -0.10125(4) 0.58265(3) 0.03873(12) Uani 1 1 d . . . Cl2 Cl 0.29094(3) 0.30862(4) 0.72581(2) 0.03386(11) Uani 1 1 d . . . Cl3 Cl 1.23891(3) 0.08934(4) 0.87517(2) 0.03385(11) Uani 1 1 d . . . Cl4 Cl 1.08349(3) 0.54332(4) 0.94891(3) 0.03782(12) Uani 1 1 d . . . H6N H 0.9147(14) 0.1495(18) 0.9593(10) 0.032(5) Uiso 1 1 d . . . H1N H 0.6044(14) 0.2653(19) 0.6324(10) 0.034(5) 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 C1 0.0273(9) 0.0257(8) 0.0279(9) 0.0018(7) 0.0046(7) -0.0049(7) C2 0.0347(10) 0.0287(9) 0.0241(8) 0.0036(7) -0.0019(7) -0.0028(7) C3 0.0208(8) 0.0281(8) 0.0271(9) -0.0005(7) -0.0035(6) -0.0011(7) C4 0.0155(7) 0.0213(8) 0.0250(8) -0.0015(6) 0.0005(6) -0.0019(6) C5 0.0142(7) 0.0211(8) 0.0260(8) -0.0024(6) 0.0007(6) -0.0007(6) C6 0.0141(7) 0.0236(8) 0.0258(8) -0.0001(6) 0.0008(6) -0.0021(6) C7 0.0161(7) 0.0269(8) 0.0292(9) 0.0040(7) 0.0015(6) -0.0039(6) C8 0.0195(8) 0.0278(8) 0.0247(8) 0.0058(7) 0.0013(6) -0.0004(6) C9 0.0153(7) 0.0216(8) 0.0235(8) -0.0004(6) 0.0011(6) 0.0007(6) C10 0.0130(7) 0.0248(8) 0.0225(8) 0.0045(6) -0.0020(6) -0.0021(6) C11 0.0165(8) 0.0251(8) 0.0322(9) 0.0005(7) -0.0011(6) 0.0009(6) C12 0.0214(8) 0.0283(9) 0.0361(10) 0.0002(7) -0.0061(7) -0.0067(7) C13 0.0140(8) 0.0316(9) 0.0435(10) 0.0068(8) -0.0041(7) -0.0050(7) C14 0.0169(8) 0.0300(9) 0.0354(9) 0.0057(7) 0.0025(7) 0.0023(7) C15 0.0202(8) 0.0236(8) 0.0235(8) 0.0031(6) -0.0011(6) -0.0011(6) C16 0.0160(7) 0.0232(8) 0.0230(8) -0.0002(6) -0.0015(6) 0.0012(6) C17 0.0139(7) 0.0310(9) 0.0286(9) 0.0012(7) -0.0007(6) -0.0013(6) C18 0.0163(7) 0.0255(8) 0.0229(8) -0.0018(6) -0.0011(6) 0.0007(6) C19 0.0132(7) 0.0294(8) 0.0284(9) 0.0004(7) -0.0015(6) -0.0051(6) C20 0.0156(7) 0.0286(8) 0.0237(8) -0.0005(7) 0.0008(6) -0.0004(6) C21 0.0185(8) 0.0522(11) 0.0220(8) 0.0038(8) 0.0017(6) -0.0049(8) C22 0.0160(8) 0.0439(10) 0.0261(9) 0.0027(8) 0.0043(6) -0.0056(7) C23 0.0123(7) 0.0251(8) 0.0270(8) -0.0019(6) 0.0016(6) -0.0002(6) C24 0.0133(7) 0.0196(7) 0.0255(8) -0.0024(6) 0.0016(6) 0.0007(6) C25 0.0148(7) 0.0201(7) 0.0259(8) -0.0028(6) 0.0017(6) -0.0003(6) C26 0.0209(8) 0.0298(9) 0.0258(8) -0.0041(7) 0.0005(6) -0.0018(7) C27 0.0326(9) 0.0313(9) 0.0227(8) -0.0011(7) 0.0027(7) 0.0009(7) C28 0.0265(9) 0.0241(8) 0.0286(9) -0.0003(7) 0.0101(7) -0.0017(7) C29 0.0139(7) 0.0263(8) 0.0199(7) 0.0026(6) -0.0010(6) -0.0009(6) C30 0.0181(7) 0.0254(8) 0.0238(8) 0.0030(6) -0.0002(6) 0.0010(6) C31 0.0145(7) 0.0373(10) 0.0316(9) 0.0078(7) 0.0010(6) 0.0025(7) C32 0.0158(8) 0.0387(10) 0.0422(10) 0.0106(8) -0.0008(7) -0.0070(7) C33 0.0221(8) 0.0267(9) 0.0399(10) 0.0041(7) -0.0027(7) -0.0060(7) C34 0.0162(7) 0.0277(8) 0.0290(9) 0.0013(7) 0.0003(6) 0.0010(6) N1 0.0176(7) 0.0261(7) 0.0249(7) 0.0021(6) -0.0008(6) -0.0025(5) N2 0.0140(6) 0.0266(7) 0.0239(7) 0.0015(5) -0.0012(5) -0.0024(5) N3 0.0223(7) 0.0522(10) 0.0305(8) 0.0100(7) -0.0016(6) -0.0019(7) N4 0.0220(7) 0.0435(9) 0.0325(8) 0.0092(7) -0.0032(6) -0.0091(6) N5 0.0128(6) 0.0247(7) 0.0240(7) 0.0000(5) -0.0003(5) -0.0011(5) N6 0.0169(6) 0.0232(7) 0.0254(7) -0.0015(6) 0.0028(6) -0.0021(5) Cl1 0.0228(2) 0.0344(2) 0.0593(3) -0.0166(2) 0.0041(2) 0.00042(17) Cl2 0.0297(2) 0.0316(2) 0.0409(2) -0.01001(19) 0.00812(18) -0.00292(17) Cl3 0.0251(2) 0.0278(2) 0.0495(3) -0.00347(19) 0.01086(18) 0.00209(17) Cl4 0.0227(2) 0.0291(2) 0.0619(3) -0.0096(2) 0.0049(2) 0.00200(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.342(2) . ? C1 C2 1.388(2) . ? C1 H1 0.9500 . ? C2 C3 1.392(2) . ? C2 H2 0.9500 . ? C3 C4 1.405(2) . ? C3 H3 0.9500 . ? C4 N1 1.383(2) . ? C4 C5 1.415(2) . ? C5 C6 1.388(2) . ? C5 C10 1.500(2) . ? C6 N2 1.3914(19) . ? C6 C7 1.445(2) . ? C7 C8 1.356(2) . ? C7 H7 0.9500 . ? C8 C9 1.452(2) . ? C8 H8 0.9500 . ? C9 N2 1.329(2) . ? C9 C16 1.460(2) . ? C10 C15 1.398(2) . ? C10 C11 1.400(2) . ? C11 C12 1.386(2) . ? C11 Cl1 1.7401(17) . ? C12 C13 1.379(2) . ? C12 H12 0.9500 . ? C13 C14 1.382(2) . ? C13 H13 0.9500 . ? C14 C15 1.387(2) . ? C14 H14 0.9500 . ? C15 Cl2 1.7402(16) . ? C16 C18 1.380(2) . ? C16 C17 1.447(2) . ? C17 N3 1.149(2) . ? C18 C19 1.445(2) . ? C18 C20 1.459(2) . ? C19 N4 1.152(2) . ? C20 N5 1.334(2) . ? C20 C21 1.446(2) . ? C21 C22 1.360(2) . ? C21 H21 0.9500 . ? C22 C23 1.440(2) . ? C22 H22 0.9500 . ? C23 N5 1.3891(19) . ? C23 C24 1.395(2) . ? C24 C25 1.406(2) . ? C24 C29 1.504(2) . ? C25 N6 1.3918(19) . ? C25 C26 1.407(2) . ? C26 C27 1.385(2) . ? C26 H26 0.9500 . ? C27 C28 1.394(2) . ? C27 H27 0.9500 . ? C28 N6 1.338(2) . ? C28 H28 0.9500 . ? C29 C30 1.395(2) . ? C29 C34 1.399(2) . ? C30 C31 1.388(2) . ? C30 Cl3 1.7408(17) . ? C31 C32 1.387(3) . ? C31 H31 0.9500 . ? C32 C33 1.378(2) . ? C32 H32 0.9500 . ? C33 C34 1.387(2) . ? C33 H33 0.9500 . ? C34 Cl4 1.7368(16) . ? N1 H1N 0.83(2) . ? N6 H6N 0.873(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 108.46(15) . . ? N1 C1 H1 125.8 . . ? C2 C1 H1 125.8 . . ? C1 C2 C3 107.32(15) . . ? C1 C2 H2 126.3 . . ? C3 C2 H2 126.3 . . ? C2 C3 C4 107.85(14) . . ? C2 C3 H3 126.1 . . ? C4 C3 H3 126.1 . . ? N1 C4 C3 106.11(14) . . ? N1 C4 C5 123.96(14) . . ? C3 C4 C5 129.92(14) . . ? C6 C5 C4 124.81(14) . . ? C6 C5 C10 119.92(14) . . ? C4 C5 C10 115.27(13) . . ? C5 C6 N2 121.56(14) . . ? C5 C6 C7 128.52(14) . . ? N2 C6 C7 109.92(13) . . ? C8 C7 C6 106.71(14) . . ? C8 C7 H7 126.6 . . ? C6 C7 H7 126.6 . . ? C7 C8 C9 105.70(14) . . ? C7 C8 H8 127.2 . . ? C9 C8 H8 127.2 . . ? N2 C9 C8 112.21(13) . . ? N2 C9 C16 121.61(14) . . ? C8 C9 C16 126.16(14) . . ? C15 C10 C11 116.34(14) . . ? C15 C10 C5 121.75(14) . . ? C11 C10 C5 121.78(14) . . ? C12 C11 C10 122.14(15) . . ? C12 C11 Cl1 117.76(13) . . ? C10 C11 Cl1 120.10(12) . . ? C13 C12 C11 119.38(16) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 120.61(15) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C13 C14 C15 119.09(16) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C14 C15 C10 122.37(15) . . ? C14 C15 Cl2 118.54(13) . . ? C10 C15 Cl2 119.07(12) . . ? C18 C16 C17 120.20(14) . . ? C18 C16 C9 125.23(14) . . ? C17 C16 C9 114.57(13) . . ? N3 C17 C16 174.46(17) . . ? C16 C18 C19 120.37(14) . . ? C16 C18 C20 127.77(14) . . ? C19 C18 C20 111.81(13) . . ? N4 C19 C18 171.09(16) . . ? N5 C20 C21 112.26(13) . . ? N5 C20 C18 123.53(14) . . ? C21 C20 C18 124.11(14) . . ? C22 C21 C20 105.89(14) . . ? C22 C21 H21 127.1 . . ? C20 C21 H21 127.1 . . ? C21 C22 C23 106.34(14) . . ? C21 C22 H22 126.8 . . ? C23 C22 H22 126.8 . . ? N5 C23 C24 122.71(14) . . ? N5 C23 C22 110.51(13) . . ? C24 C23 C22 126.72(14) . . ? C23 C24 C25 124.76(14) . . ? C23 C24 C29 117.66(13) . . ? C25 C24 C29 117.55(13) . . ? N6 C25 C24 123.74(14) . . ? N6 C25 C26 106.08(14) . . ? C24 C25 C26 130.17(14) . . ? C27 C26 C25 108.05(14) . . ? C27 C26 H26 126.0 . . ? C25 C26 H26 126.0 . . ? C26 C27 C28 107.23(15) . . ? C26 C27 H27 126.4 . . ? C28 C27 H27 126.4 . . ? N6 C28 C27 108.81(14) . . ? N6 C28 H28 125.6 . . ? C27 C28 H28 125.6 . . ? C30 C29 C34 116.29(14) . . ? C30 C29 C24 122.66(14) . . ? C34 C29 C24 121.04(13) . . ? C31 C30 C29 122.27(15) . . ? C31 C30 Cl3 118.11(12) . . ? C29 C30 Cl3 119.60(12) . . ? C32 C31 C30 119.23(15) . . ? C32 C31 H31 120.4 . . ? C30 C31 H31 120.4 . . ? C33 C32 C31 120.51(15) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C32 C33 C34 119.10(16) . . ? C32 C33 H33 120.5 . . ? C34 C33 H33 120.5 . . ? C33 C34 C29 122.59(15) . . ? C33 C34 Cl4 117.93(13) . . ? C29 C34 Cl4 119.47(12) . . ? C1 N1 C4 110.25(14) . . ? C1 N1 H1N 126.6(14) . . ? C4 N1 H1N 123.1(14) . . ? C9 N2 C6 105.45(13) . . ? C20 N5 C23 105.00(13) . . ? C28 N6 C25 109.83(14) . . ? C28 N6 H6N 128.6(13) . . ? C25 N6 H6N 121.5(13) . . ? 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 N1 C1 C2 C3 -0.09(19) . . . . ? C1 C2 C3 C4 0.13(19) . . . . ? C2 C3 C4 N1 -0.11(18) . . . . ? C2 C3 C4 C5 179.60(16) . . . . ? N1 C4 C5 C6 2.0(3) . . . . ? C3 C4 C5 C6 -177.66(16) . . . . ? N1 C4 C5 C10 -178.37(14) . . . . ? C3 C4 C5 C10 2.0(2) . . . . ? C4 C5 C6 N2 -1.0(2) . . . . ? C10 C5 C6 N2 179.35(14) . . . . ? C4 C5 C6 C7 178.57(16) . . . . ? C10 C5 C6 C7 -1.0(3) . . . . ? C5 C6 C7 C8 -178.90(16) . . . . ? N2 C6 C7 C8 0.76(19) . . . . ? C6 C7 C8 C9 -0.97(18) . . . . ? C7 C8 C9 N2 0.94(19) . . . . ? C7 C8 C9 C16 -177.62(15) . . . . ? C6 C5 C10 C15 84.80(19) . . . . ? C4 C5 C10 C15 -94.84(18) . . . . ? C6 C5 C10 C11 -99.41(19) . . . . ? C4 C5 C10 C11 80.95(19) . . . . ? C15 C10 C11 C12 0.7(2) . . . . ? C5 C10 C11 C12 -175.35(15) . . . . ? C15 C10 C11 Cl1 -179.56(12) . . . . ? C5 C10 C11 Cl1 4.4(2) . . . . ? C10 C11 C12 C13 -1.8(3) . . . . ? Cl1 C11 C12 C13 178.45(13) . . . . ? C11 C12 C13 C14 0.7(3) . . . . ? C12 C13 C14 C15 1.5(3) . . . . ? C13 C14 C15 C10 -2.6(2) . . . . ? C13 C14 C15 Cl2 175.47(13) . . . . ? C11 C10 C15 C14 1.6(2) . . . . ? C5 C10 C15 C14 177.57(15) . . . . ? C11 C10 C15 Cl2 -176.54(12) . . . . ? C5 C10 C15 Cl2 -0.5(2) . . . . ? N2 C9 C16 C18 -5.2(2) . . . . ? C8 C9 C16 C18 173.27(16) . . . . ? N2 C9 C16 C17 174.14(15) . . . . ? C8 C9 C16 C17 -7.4(2) . . . . ? C18 C16 C17 N3 161.4(18) . . . . ? C9 C16 C17 N3 -18(2) . . . . ? C17 C16 C18 C19 -177.53(15) . . . . ? C9 C16 C18 C19 1.7(2) . . . . ? C17 C16 C18 C20 -0.4(3) . . . . ? C9 C16 C18 C20 178.85(15) . . . . ? C16 C18 C19 N4 173.0(11) . . . . ? C20 C18 C19 N4 -4.5(12) . . . . ? C16 C18 C20 N5 -1.9(3) . . . . ? C19 C18 C20 N5 175.44(15) . . . . ? C16 C18 C20 C21 -177.95(17) . . . . ? C19 C18 C20 C21 -0.6(2) . . . . ? N5 C20 C21 C22 -0.7(2) . . . . ? C18 C20 C21 C22 175.80(16) . . . . ? C20 C21 C22 C23 0.2(2) . . . . ? C21 C22 C23 N5 0.3(2) . . . . ? C21 C22 C23 C24 -176.78(16) . . . . ? N5 C23 C24 C25 0.7(2) . . . . ? C22 C23 C24 C25 177.45(16) . . . . ? N5 C23 C24 C29 -177.00(14) . . . . ? C22 C23 C24 C29 -0.3(2) . . . . ? C23 C24 C25 N6 -3.3(2) . . . . ? C29 C24 C25 N6 174.47(14) . . . . ? C23 C24 C25 C26 176.51(16) . . . . ? C29 C24 C25 C26 -5.8(2) . . . . ? N6 C25 C26 C27 0.16(18) . . . . ? C24 C25 C26 C27 -179.64(16) . . . . ? C25 C26 C27 C28 -0.43(19) . . . . ? C26 C27 C28 N6 0.55(19) . . . . ? C23 C24 C29 C30 -89.43(19) . . . . ? C25 C24 C29 C30 92.68(18) . . . . ? C23 C24 C29 C34 89.23(19) . . . . ? C25 C24 C29 C34 -88.66(18) . . . . ? C34 C29 C30 C31 -0.4(2) . . . . ? C24 C29 C30 C31 178.30(15) . . . . ? C34 C29 C30 Cl3 -179.03(12) . . . . ? C24 C29 C30 Cl3 -0.3(2) . . . . ? C29 C30 C31 C32 1.3(2) . . . . ? Cl3 C30 C31 C32 179.96(13) . . . . ? C30 C31 C32 C33 -0.9(3) . . . . ? C31 C32 C33 C34 -0.4(3) . . . . ? C32 C33 C34 C29 1.3(3) . . . . ? C32 C33 C34 Cl4 -177.34(14) . . . . ? C30 C29 C34 C33 -0.9(2) . . . . ? C24 C29 C34 C33 -179.67(15) . . . . ? C30 C29 C34 Cl4 177.72(12) . . . . ? C24 C29 C34 Cl4 -1.0(2) . . . . ? C2 C1 N1 C4 0.02(19) . . . . ? C3 C4 N1 C1 0.06(18) . . . . ? C5 C4 N1 C1 -179.68(15) . . . . ? C8 C9 N2 C6 -0.46(17) . . . . ? C16 C9 N2 C6 178.17(14) . . . . ? C5 C6 N2 C9 179.51(15) . . . . ? C7 C6 N2 C9 -0.17(17) . . . . ? C21 C20 N5 C23 0.80(18) . . . . ? C18 C20 N5 C23 -175.68(15) . . . . ? C24 C23 N5 C20 176.54(15) . . . . ? C22 C23 N5 C20 -0.67(18) . . . . ? C27 C28 N6 C25 -0.45(18) . . . . ? C24 C25 N6 C28 179.99(14) . . . . ? C26 C25 N6 C28 0.18(18) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.323 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.049 #===END data_dd308 _database_code_depnum_ccdc_archive 'CCDC 716868' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H11 Cl4 N3 O3' _chemical_formula_weight 507.14 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 7.8137(8) _cell_length_b 9.9057(11) _cell_length_c 14.0837(16) _cell_angle_alpha 84.895(5) _cell_angle_beta 77.368(5) _cell_angle_gamma 81.828(5) _cell_volume 1051.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9847 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 28.02 _exptl_crystal_description irregular _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.603 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.595 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.864 _exptl_absorpt_correction_T_max 0.931 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36857 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.09 _reflns_number_total 5085 _reflns_number_gt 4365 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0372P)^2^+0.4861P] 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 5085 _refine_ls_number_parameters 294 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.39784(18) 0.85221(14) 1.15211(10) 0.0235(3) Uani 1 1 d . . . C2 C 0.30730(18) 0.87798(15) 1.07067(10) 0.0236(3) Uani 1 1 d . . . C3 C 0.27756(18) 0.75812(15) 1.04394(10) 0.0237(3) Uani 1 1 d . . . C4 C 0.34763(17) 0.65111(15) 1.10628(10) 0.0224(3) Uani 1 1 d . . . C5 C 0.34992(18) 0.51356(15) 1.11345(10) 0.0231(3) Uani 1 1 d . . . C6 C 0.43018(18) 0.41860(14) 1.17950(10) 0.0227(3) Uani 1 1 d . . . C7 C 0.4055(2) 0.28155(15) 1.20163(12) 0.0285(3) Uani 1 1 d . . . H7 H 0.3316 0.2327 1.1758 0.034 Uiso 1 1 calc R . . C8 C 0.5092(2) 0.22988(15) 1.26843(12) 0.0288(3) Uani 1 1 d . . . H8 H 0.5172 0.1395 1.2975 0.035 Uiso 1 1 calc R . . C9 C 0.59936(19) 0.33408(14) 1.28518(10) 0.0231(3) Uani 1 1 d . . . C10 C 0.73335(19) 0.32676(14) 1.34214(10) 0.0228(3) Uani 1 1 d . . . C11 C 0.84056(19) 0.42470(14) 1.33803(10) 0.0228(3) Uani 1 1 d . . . C12 C 0.9877(2) 0.42163(16) 1.38689(11) 0.0284(3) Uani 1 1 d . . . H12 H 1.0247 0.3514 1.4313 0.034 Uiso 1 1 calc R . . C13 C 1.0607(2) 0.53689(16) 1.35718(11) 0.0298(3) Uani 1 1 d . . . H13 H 1.1600 0.5648 1.3752 0.036 Uiso 1 1 calc R . . C14 C 0.95413(18) 0.60992(14) 1.29119(10) 0.0231(3) Uani 1 1 d . . . C15 C 0.26870(19) 0.44838(16) 1.05010(11) 0.0280(3) Uani 1 1 d . . . C16 C 0.75203(19) 0.19872(14) 1.40535(10) 0.0229(3) Uani 1 1 d . . . C17 C 0.6487(2) 0.18563(15) 1.49912(11) 0.0279(3) Uani 1 1 d . . . C18 C 0.6550(2) 0.06465(16) 1.55592(11) 0.0310(3) Uani 1 1 d . . . H18 H 0.5854 0.0597 1.6202 0.037 Uiso 1 1 calc R . . C19 C 0.7632(2) -0.04868(16) 1.51823(12) 0.0304(3) Uani 1 1 d . . . H19 H 0.7647 -0.1331 1.5560 0.036 Uiso 1 1 calc R . . C20 C 0.8694(2) -0.04088(15) 1.42623(12) 0.0280(3) Uani 1 1 d . . . H20 H 0.9450 -0.1189 1.4006 0.034 Uiso 1 1 calc R . . C21 C 0.86408(19) 0.08260(14) 1.37183(10) 0.0234(3) Uani 1 1 d . . . C22 C 0.8618(2) 0.79596(16) 1.19257(12) 0.0317(3) Uani 1 1 d . . . H22A H 0.8582 0.7365 1.1412 0.048 Uiso 1 1 calc R . . H22B H 0.8972 0.8838 1.1629 0.048 Uiso 1 1 calc R . . H22C H 0.7444 0.8111 1.2352 0.048 Uiso 1 1 calc R . . N1 N 0.54751(16) 0.44850(12) 1.23156(9) 0.0220(2) Uani 1 1 d . . . N2 N 0.82636(15) 0.54653(12) 1.27922(9) 0.0221(2) Uani 1 1 d . . . N3 N 0.2148(2) 0.38578(16) 1.00161(12) 0.0412(4) Uani 1 1 d . . . O1 O 0.44719(15) 0.92733(11) 1.19898(8) 0.0299(2) Uani 1 1 d . . . O2 O 0.42204(13) 0.71090(10) 1.16990(7) 0.0235(2) Uani 1 1 d . . . O3 O 0.98780(13) 0.73187(10) 1.24908(8) 0.0262(2) Uani 1 1 d . . . Cl1 Cl 0.24994(5) 1.03820(4) 1.02580(3) 0.03168(10) Uani 1 1 d . . . Cl2 Cl 0.17231(5) 0.73577(4) 0.95475(3) 0.03291(10) Uani 1 1 d . . . Cl3 Cl 0.50590(7) 0.32512(4) 1.54669(3) 0.04787(13) Uani 1 1 d . . . Cl4 Cl 1.00404(5) 0.09365(4) 1.25801(3) 0.03463(10) Uani 1 1 d . . . H1N H 0.595(2) 0.520(2) 1.2286(14) 0.034(5) 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 C1 0.0237(7) 0.0209(7) 0.0242(7) 0.0004(5) -0.0032(5) -0.0014(5) C2 0.0228(7) 0.0245(7) 0.0209(7) 0.0030(5) -0.0029(5) 0.0000(5) C3 0.0188(6) 0.0313(7) 0.0200(7) 0.0000(6) -0.0035(5) -0.0012(5) C4 0.0194(6) 0.0267(7) 0.0217(7) -0.0026(5) -0.0049(5) -0.0031(5) C5 0.0192(6) 0.0266(7) 0.0241(7) -0.0031(6) -0.0041(5) -0.0043(5) C6 0.0210(6) 0.0219(7) 0.0256(7) -0.0013(5) -0.0037(5) -0.0056(5) C7 0.0280(7) 0.0242(7) 0.0350(8) -0.0005(6) -0.0057(6) -0.0113(6) C8 0.0326(8) 0.0209(7) 0.0321(8) 0.0038(6) -0.0042(6) -0.0084(6) C9 0.0267(7) 0.0195(6) 0.0214(7) 0.0015(5) -0.0018(5) -0.0041(5) C10 0.0286(7) 0.0193(6) 0.0184(6) 0.0001(5) -0.0019(5) -0.0014(5) C11 0.0278(7) 0.0207(6) 0.0187(6) -0.0004(5) -0.0037(5) -0.0013(5) C12 0.0337(8) 0.0274(7) 0.0250(7) -0.0016(6) -0.0104(6) -0.0003(6) C13 0.0301(8) 0.0327(8) 0.0294(8) -0.0035(6) -0.0112(6) -0.0042(6) C14 0.0251(7) 0.0230(7) 0.0206(7) -0.0038(5) -0.0024(5) -0.0033(5) C15 0.0238(7) 0.0295(8) 0.0320(8) -0.0024(6) -0.0070(6) -0.0056(6) C16 0.0288(7) 0.0188(6) 0.0207(7) 0.0005(5) -0.0045(5) -0.0033(5) C17 0.0356(8) 0.0210(7) 0.0241(7) -0.0016(6) -0.0012(6) -0.0010(6) C18 0.0405(9) 0.0282(8) 0.0215(7) 0.0037(6) -0.0016(6) -0.0056(6) C19 0.0389(8) 0.0225(7) 0.0308(8) 0.0070(6) -0.0122(7) -0.0048(6) C20 0.0306(7) 0.0196(7) 0.0342(8) -0.0020(6) -0.0097(6) 0.0000(6) C21 0.0257(7) 0.0232(7) 0.0213(7) -0.0024(5) -0.0037(5) -0.0045(5) C22 0.0371(8) 0.0267(7) 0.0349(8) 0.0056(6) -0.0144(7) -0.0099(6) N1 0.0259(6) 0.0169(6) 0.0245(6) 0.0004(5) -0.0065(5) -0.0056(5) N2 0.0254(6) 0.0195(6) 0.0213(6) 0.0002(4) -0.0041(4) -0.0044(5) N3 0.0395(8) 0.0424(8) 0.0484(9) -0.0096(7) -0.0172(7) -0.0110(7) O1 0.0382(6) 0.0232(5) 0.0305(6) -0.0031(4) -0.0117(5) -0.0034(4) O2 0.0287(5) 0.0190(5) 0.0247(5) -0.0001(4) -0.0104(4) -0.0026(4) O3 0.0281(5) 0.0233(5) 0.0290(5) 0.0002(4) -0.0068(4) -0.0087(4) Cl1 0.0349(2) 0.02716(18) 0.02936(19) 0.00753(14) -0.00638(15) 0.00219(15) Cl2 0.02964(19) 0.0427(2) 0.02892(19) -0.00446(16) -0.01421(15) 0.00088(16) Cl3 0.0628(3) 0.0285(2) 0.0365(2) -0.00243(17) 0.0146(2) 0.00872(19) Cl4 0.0374(2) 0.03011(19) 0.0303(2) -0.00501(15) 0.00717(15) -0.00402(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.1909(18) . ? C1 O2 1.3931(17) . ? C1 C2 1.460(2) . ? C2 C3 1.342(2) . ? C2 Cl1 1.6918(14) . ? C3 C4 1.4401(19) . ? C3 Cl2 1.6900(14) . ? C4 C5 1.355(2) . ? C4 O2 1.3827(17) . ? C5 C6 1.4405(19) . ? C5 C15 1.443(2) . ? C6 N1 1.3696(18) . ? C6 C7 1.396(2) . ? C7 C8 1.390(2) . ? C7 H7 0.9500 . ? C8 C9 1.393(2) . ? C8 H8 0.9500 . ? C9 N1 1.3674(18) . ? C9 C10 1.442(2) . ? C10 C11 1.359(2) . ? C10 C16 1.4919(19) . ? C11 N2 1.4067(17) . ? C11 C12 1.459(2) . ? C12 C13 1.342(2) . ? C12 H12 0.9500 . ? C13 C14 1.459(2) . ? C13 H13 0.9500 . ? C14 N2 1.3000(18) . ? C14 O3 1.3323(17) . ? C15 N3 1.142(2) . ? C16 C21 1.3936(19) . ? C16 C17 1.395(2) . ? C17 C18 1.381(2) . ? C17 Cl3 1.7328(15) . ? C18 C19 1.377(2) . ? C18 H18 0.9500 . ? C19 C20 1.380(2) . ? C19 H19 0.9500 . ? C20 C21 1.385(2) . ? C20 H20 0.9500 . ? C21 Cl4 1.7359(15) . ? C22 O3 1.4425(18) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N1 H1N 0.84(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 O1 C1 O2 121.92(13) . . ? O1 C1 C2 131.85(14) . . ? O2 C1 C2 106.22(12) . . ? C3 C2 C1 108.85(12) . . ? C3 C2 Cl1 129.24(12) . . ? C1 C2 Cl1 121.88(11) . . ? C2 C3 C4 107.97(12) . . ? C2 C3 Cl2 126.35(11) . . ? C4 C3 Cl2 125.66(12) . . ? C5 C4 O2 118.85(12) . . ? C5 C4 C3 133.11(13) . . ? O2 C4 C3 108.03(12) . . ? C4 C5 C6 126.43(13) . . ? C4 C5 C15 120.22(13) . . ? C6 C5 C15 113.34(13) . . ? N1 C6 C7 107.78(12) . . ? N1 C6 C5 125.03(13) . . ? C7 C6 C5 127.19(13) . . ? C8 C7 C6 107.31(13) . . ? C8 C7 H7 126.3 . . ? C6 C7 H7 126.3 . . ? C7 C8 C9 107.87(13) . . ? C7 C8 H8 126.1 . . ? C9 C8 H8 126.1 . . ? N1 C9 C8 107.66(13) . . ? N1 C9 C10 123.81(13) . . ? C8 C9 C10 128.40(13) . . ? C11 C10 C9 124.12(13) . . ? C11 C10 C16 121.06(13) . . ? C9 C10 C16 114.78(12) . . ? C10 C11 N2 122.47(13) . . ? C10 C11 C12 127.97(13) . . ? N2 C11 C12 109.51(12) . . ? C13 C12 C11 106.90(13) . . ? C13 C12 H12 126.5 . . ? C11 C12 H12 126.5 . . ? C12 C13 C14 104.87(13) . . ? C12 C13 H13 127.6 . . ? C14 C13 H13 127.6 . . ? N2 C14 O3 124.51(13) . . ? N2 C14 C13 114.29(13) . . ? O3 C14 C13 121.20(13) . . ? N3 C15 C5 173.49(17) . . ? C21 C16 C17 116.22(13) . . ? C21 C16 C10 122.02(12) . . ? C17 C16 C10 121.61(12) . . ? C18 C17 C16 122.37(14) . . ? C18 C17 Cl3 118.34(12) . . ? C16 C17 Cl3 119.29(11) . . ? C19 C18 C17 119.24(14) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 120.68(14) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C19 C20 C21 118.88(14) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C20 C21 C16 122.54(13) . . ? C20 C21 Cl4 118.73(11) . . ? C16 C21 Cl4 118.73(11) . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C9 N1 C6 109.37(12) . . ? C9 N1 H1N 121.1(13) . . ? C6 N1 H1N 129.1(13) . . ? C14 N2 C11 104.42(12) . . ? C4 O2 C1 108.90(10) . . ? C14 O3 C22 114.52(11) . . ? 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 O1 C1 C2 C3 -178.94(16) . . . . ? O2 C1 C2 C3 1.13(16) . . . . ? O1 C1 C2 Cl1 -0.7(2) . . . . ? O2 C1 C2 Cl1 179.35(10) . . . . ? C1 C2 C3 C4 -0.19(16) . . . . ? Cl1 C2 C3 C4 -178.25(11) . . . . ? C1 C2 C3 Cl2 178.48(11) . . . . ? Cl1 C2 C3 Cl2 0.4(2) . . . . ? C2 C3 C4 C5 177.94(15) . . . . ? Cl2 C3 C4 C5 -0.7(2) . . . . ? C2 C3 C4 O2 -0.83(16) . . . . ? Cl2 C3 C4 O2 -179.51(10) . . . . ? O2 C4 C5 C6 -2.8(2) . . . . ? C3 C4 C5 C6 178.52(14) . . . . ? O2 C4 C5 C15 178.14(12) . . . . ? C3 C4 C5 C15 -0.5(2) . . . . ? C4 C5 C6 N1 -14.2(2) . . . . ? C15 C5 C6 N1 164.95(13) . . . . ? C4 C5 C6 C7 166.49(15) . . . . ? C15 C5 C6 C7 -14.4(2) . . . . ? N1 C6 C7 C8 0.40(17) . . . . ? C5 C6 C7 C8 179.85(14) . . . . ? C6 C7 C8 C9 -1.28(18) . . . . ? C7 C8 C9 N1 1.68(17) . . . . ? C7 C8 C9 C10 -174.23(14) . . . . ? N1 C9 C10 C11 -10.0(2) . . . . ? C8 C9 C10 C11 165.34(15) . . . . ? N1 C9 C10 C16 172.14(13) . . . . ? C8 C9 C10 C16 -12.5(2) . . . . ? C9 C10 C11 N2 2.2(2) . . . . ? C16 C10 C11 N2 -179.99(12) . . . . ? C9 C10 C11 C12 -174.92(14) . . . . ? C16 C10 C11 C12 2.8(2) . . . . ? C10 C11 C12 C13 176.61(15) . . . . ? N2 C11 C12 C13 -0.86(17) . . . . ? C11 C12 C13 C14 0.83(16) . . . . ? C12 C13 C14 N2 -0.60(18) . . . . ? C12 C13 C14 O3 178.64(13) . . . . ? C4 C5 C15 N3 157.0(15) . . . . ? C6 C5 C15 N3 -22.2(16) . . . . ? C11 C10 C16 C21 -89.41(18) . . . . ? C9 C10 C16 C21 88.55(17) . . . . ? C11 C10 C16 C17 95.23(18) . . . . ? C9 C10 C16 C17 -86.81(17) . . . . ? C21 C16 C17 C18 -0.5(2) . . . . ? C10 C16 C17 C18 175.15(15) . . . . ? C21 C16 C17 Cl3 179.87(11) . . . . ? C10 C16 C17 Cl3 -4.5(2) . . . . ? C16 C17 C18 C19 -1.8(3) . . . . ? Cl3 C17 C18 C19 177.84(13) . . . . ? C17 C18 C19 C20 2.4(2) . . . . ? C18 C19 C20 C21 -0.7(2) . . . . ? C19 C20 C21 C16 -1.7(2) . . . . ? C19 C20 C21 Cl4 177.59(12) . . . . ? C17 C16 C21 C20 2.3(2) . . . . ? C10 C16 C21 C20 -173.33(14) . . . . ? C17 C16 C21 Cl4 -177.04(11) . . . . ? C10 C16 C21 Cl4 7.36(19) . . . . ? C8 C9 N1 C6 -1.45(16) . . . . ? C10 C9 N1 C6 174.70(13) . . . . ? C7 C6 N1 C9 0.65(16) . . . . ? C5 C6 N1 C9 -178.81(13) . . . . ? O3 C14 N2 C11 -179.15(13) . . . . ? C13 C14 N2 C11 0.06(16) . . . . ? C10 C11 N2 C14 -177.16(13) . . . . ? C12 C11 N2 C14 0.47(15) . . . . ? C5 C4 O2 C1 -177.42(12) . . . . ? C3 C4 O2 C1 1.55(15) . . . . ? O1 C1 O2 C4 178.43(14) . . . . ? C2 C1 O2 C4 -1.64(14) . . . . ? N2 C14 O3 C22 4.2(2) . . . . ? C13 C14 O3 C22 -174.93(13) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.09 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.367 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.048 #===END