# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 # 1. SUBMISSION DETAILS _publ_contact_author_name 'Chao Guo Yan' _publ_contact_author_address ; College of Chemistry & Chemical Engineering Yangzhou University Yangzhou 225002, P.R. China ; _publ_contact_author_phone +86-514-7975531 _publ_contact_author_fax +86-514-7975590-8401 _publ_contact_author_email cgyan@yzu.edu.cn _publ_section_title ; One-step synthesis of polysubstituted benzene derivatives by a four-component tandem cyclization of pyridine, \a-bromoacetate, malononitrile and aromatic aldehydes ; loop_ _publ_author_name _publ_author_footnote _publ_author_address C.G.Yan ? ; College of Chemistry & Chemical Engineering Yangzhou University Yangzhou 225002, P.R. China ; X.K.Song ? ; College of Chemistry & Chemical Engineering Yangzhou University Yangzhou 225002, P.R. China ; Q.F.Wang ? ; College of Chemistry & Chemical Engineering Yangzhou University Yangzhou 225002, P.R. China ; J.Sun ? ; College of Chemistry & Chemical Engineering Yangzhou University Yangzhou 225002, P.R. China ; U.Siemeling ? ; Institute for Chemistry, University of Kassel, Heinrich-Plett-Str. 40, 34132 Kassel Germany ; C.Bruhn ? ; Institute for Chemistry, University of Kassel, Heinrich-Plett-Str. 40, 34132 Kassel Germany ; #====================================================================== data_1a _database_code_depnum_ccdc_archive 'CCDC 663309' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H17 N3 O2' _chemical_formula_sum 'C23 H17 N3 O2' _chemical_formula_weight 367.40 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 10.2906(16) _cell_length_b 9.6726(15) _cell_length_c 38.429(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.455(2) _cell_angle_gamma 90.00 _cell_volume 3821.6(10) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 2455 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 19.55 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9835 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27230 _diffrn_reflns_av_R_equivalents 0.0809 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.05 _reflns_number_total 6769 _reflns_number_gt 3445 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0305P)^2^+2.5860P] 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 6769 _refine_ls_number_parameters 507 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1299 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1307 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _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 C1 C 0.5471(3) 0.7210(3) 0.74496(7) 0.0383(7) Uani 1 1 d . . . C2 C 0.6092(3) 0.8264(3) 0.76418(7) 0.0374(7) Uani 1 1 d . . . C3 C 0.6432(3) 0.8074(3) 0.79977(7) 0.0396(7) Uani 1 1 d . . . C4 C 0.6118(3) 0.6801(3) 0.81439(7) 0.0372(7) Uani 1 1 d . . . C5 C 0.5428(3) 0.5771(3) 0.79575(7) 0.0393(7) Uani 1 1 d . . . C6 C 0.5082(3) 0.5981(3) 0.76039(7) 0.0396(7) Uani 1 1 d . . . C7 C 0.5428(3) 0.7315(4) 0.70597(8) 0.0480(8) Uani 1 1 d . . . C8 C 0.5002(5) 0.8689(4) 0.65573(9) 0.0968(15) Uani 1 1 d . . . H8A H 0.5870 0.8430 0.6493 0.116 Uiso 1 1 calc R . . H8B H 0.4380 0.8127 0.6423 0.116 Uiso 1 1 calc R . . C9 C 0.4786(5) 1.0080(5) 0.64851(11) 0.1174(18) Uani 1 1 d . . . H9A H 0.3934 1.0335 0.6555 0.176 Uiso 1 1 calc R . . H9B H 0.4847 1.0238 0.6240 0.176 Uiso 1 1 calc R . . H9C H 0.5426 1.0628 0.6611 0.176 Uiso 1 1 calc R . . C10 C 0.6421(3) 0.9558(3) 0.74903(7) 0.0434(8) Uani 1 1 d . . . C11 C 0.6568(3) 0.6549(3) 0.84992(8) 0.0445(8) Uani 1 1 d . . . C12 C 0.5129(3) 0.4458(3) 0.81429(7) 0.0443(8) Uani 1 1 d . . . C13 C 0.6123(4) 0.3620(3) 0.82578(9) 0.0602(10) Uani 1 1 d . . . H13 H 0.6970 0.3848 0.8205 0.072 Uiso 1 1 calc R . . C14 C 0.5908(5) 0.2438(4) 0.84508(10) 0.0782(12) Uani 1 1 d . . . H14 H 0.6604 0.1891 0.8529 0.094 Uiso 1 1 calc R . . C15 C 0.4679(5) 0.2083(4) 0.85246(11) 0.0913(14) Uani 1 1 d . . . H15 H 0.4526 0.1295 0.8655 0.110 Uiso 1 1 calc R . . C16 C 0.3658(5) 0.2894(5) 0.84054(12) 0.0982(15) Uani 1 1 d . . . H16 H 0.2812 0.2642 0.8454 0.118 Uiso 1 1 calc R . . C17 C 0.3875(4) 0.4107(4) 0.82103(9) 0.0681(10) Uani 1 1 d . . . H17 H 0.3182 0.4654 0.8130 0.082 Uiso 1 1 calc R . . C18 C 0.4276(3) 0.4958(3) 0.73986(7) 0.0419(8) Uani 1 1 d . . . C19 C 0.4646(3) 0.3587(3) 0.73700(8) 0.0524(9) Uani 1 1 d . . . H19 H 0.5438 0.3294 0.7470 0.063 Uiso 1 1 calc R . . C20 C 0.3844(4) 0.2655(4) 0.71944(9) 0.0644(10) Uani 1 1 d . . . H20 H 0.4094 0.1733 0.7179 0.077 Uiso 1 1 calc R . . C21 C 0.2681(4) 0.3077(4) 0.70423(9) 0.0714(11) Uani 1 1 d . . . H21 H 0.2143 0.2444 0.6924 0.086 Uiso 1 1 calc R . . C22 C 0.2315(4) 0.4433(4) 0.70650(9) 0.0689(11) Uani 1 1 d . . . H22 H 0.1532 0.4723 0.6959 0.083 Uiso 1 1 calc R . . C23 C 0.3097(3) 0.5372(4) 0.72433(8) 0.0564(9) Uani 1 1 d . . . H23 H 0.2835 0.6288 0.7260 0.068 Uiso 1 1 calc R . . C24 C 0.8257(3) -0.0961(3) 0.03401(7) 0.0417(8) Uani 1 1 d . . . C25 C 0.8545(3) -0.2038(3) 0.01141(7) 0.0412(8) Uani 1 1 d . . . C26 C 0.8208(3) -0.1952(3) -0.02447(7) 0.0432(8) Uani 1 1 d . . . C27 C 0.7607(3) -0.0712(3) -0.03599(7) 0.0409(7) Uani 1 1 d . . . C28 C 0.7317(3) 0.0371(3) -0.01326(7) 0.0402(7) Uani 1 1 d . . . C29 C 0.7630(3) 0.0237(3) 0.02257(7) 0.0402(7) Uani 1 1 d . . . C30 C 0.8630(3) -0.1145(3) 0.07183(8) 0.0486(8) Uani 1 1 d . . . C31 C 0.9662(4) -0.0059(4) 0.12109(8) 0.0728(11) Uani 1 1 d . . . H31A H 1.0448 -0.0573 0.1272 0.087 Uiso 1 1 calc R . . H31B H 0.8950 -0.0458 0.1334 0.087 Uiso 1 1 calc R . . C32 C 0.9830(4) 0.1404(4) 0.13061(9) 0.0760(11) Uani 1 1 d . . . H32A H 1.0517 0.1797 0.1177 0.114 Uiso 1 1 calc R . . H32B H 1.0048 0.1476 0.1551 0.114 Uiso 1 1 calc R . . H32C H 0.9036 0.1895 0.1253 0.114 Uiso 1 1 calc R . . C33 C 0.9202(3) -0.3261(3) 0.02435(8) 0.0492(8) Uani 1 1 d . . . C34 C 0.7291(3) -0.0560(3) -0.07253(8) 0.0462(8) Uani 1 1 d . . . C35 C 0.6703(3) 0.1651(3) -0.02778(7) 0.0430(8) Uani 1 1 d . . . C36 C 0.7355(4) 0.2446(3) -0.05137(8) 0.0560(9) Uani 1 1 d . . . H36 H 0.8163 0.2158 -0.0586 0.067 Uiso 1 1 calc R . . C37 C 0.6825(5) 0.3650(4) -0.06420(10) 0.0810(13) Uani 1 1 d . . . H37 H 0.7278 0.4181 -0.0798 0.097 Uiso 1 1 calc R . . C38 C 0.5632(5) 0.4072(4) -0.05409(13) 0.0980(16) Uani 1 1 d . . . H38 H 0.5276 0.4893 -0.0627 0.118 Uiso 1 1 calc R . . C39 C 0.4958(4) 0.3289(5) -0.03125(13) 0.0924(14) Uani 1 1 d . . . H39 H 0.4140 0.3573 -0.0247 0.111 Uiso 1 1 calc R . . C40 C 0.5493(4) 0.2074(4) -0.01791(10) 0.0670(10) Uani 1 1 d . . . H40 H 0.5037 0.1545 -0.0023 0.080 Uiso 1 1 calc R . . C41 C 0.7259(3) 0.1311(3) 0.04807(7) 0.0436(8) Uani 1 1 d . . . C42 C 0.7761(3) 0.2652(3) 0.04734(8) 0.0525(9) Uani 1 1 d . . . H42 H 0.8330 0.2899 0.0302 0.063 Uiso 1 1 calc R . . C43 C 0.7417(4) 0.3611(4) 0.07190(9) 0.0609(10) Uani 1 1 d . . . H43 H 0.7759 0.4500 0.0714 0.073 Uiso 1 1 calc R . . C44 C 0.6569(4) 0.3256(4) 0.09709(9) 0.0677(11) Uani 1 1 d . . . H44 H 0.6338 0.3908 0.1135 0.081 Uiso 1 1 calc R . . C45 C 0.6061(3) 0.1948(4) 0.09813(9) 0.0689(11) Uani 1 1 d . . . H45 H 0.5492 0.1709 0.1153 0.083 Uiso 1 1 calc R . . C46 C 0.6400(3) 0.0983(3) 0.07353(8) 0.0551(9) Uani 1 1 d . . . H46 H 0.6045 0.0099 0.0741 0.066 Uiso 1 1 calc R . . N1 N 0.6695(3) 1.0628(3) 0.73909(7) 0.0638(8) Uani 1 1 d . . . N2 N 0.7055(3) 0.9073(3) 0.81843(6) 0.0611(8) Uani 1 1 d . . . H2A H 0.7272 0.8935 0.8400 0.073 Uiso 1 1 calc R . . H2B H 0.7236 0.9847 0.8088 0.073 Uiso 1 1 calc R . . N3 N 0.6985(3) 0.6421(3) 0.87772(7) 0.0614(8) Uani 1 1 d . . . N4 N 0.9743(3) -0.4224(3) 0.03375(8) 0.0726(9) Uani 1 1 d . . . N5 N 0.8446(3) -0.2993(3) -0.04661(6) 0.0582(8) Uani 1 1 d . . . H5A H 0.8814 -0.3738 -0.0390 0.070 Uiso 1 1 calc R . . H5B H 0.8230 -0.2913 -0.0684 0.070 Uiso 1 1 calc R . . N6 N 0.7058(3) -0.0467(3) -0.10165(7) 0.0627(8) Uani 1 1 d . . . O1 O 0.5963(2) 0.6476(3) 0.68792(6) 0.0692(7) Uani 1 1 d . . . O2 O 0.4858(2) 0.8441(2) 0.69408(6) 0.0662(7) Uani 1 1 d . . . O3 O 0.8291(3) -0.2103(3) 0.08888(6) 0.0813(8) Uani 1 1 d . . . O4 O 0.9383(2) -0.0125(2) 0.08341(5) 0.0575(6) 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 C1 0.0436(19) 0.0410(18) 0.0297(16) 0.0001(14) -0.0040(14) 0.0010(15) C2 0.0464(19) 0.0338(17) 0.0316(17) 0.0017(14) -0.0007(14) 0.0009(14) C3 0.0503(19) 0.0344(17) 0.0338(17) -0.0041(14) -0.0029(15) -0.0010(15) C4 0.0464(19) 0.0378(17) 0.0273(16) -0.0013(14) -0.0023(14) 0.0010(15) C5 0.0435(19) 0.0384(17) 0.0362(18) -0.0003(14) 0.0021(14) 0.0031(15) C6 0.0458(19) 0.0394(18) 0.0336(18) 0.0002(14) 0.0002(15) 0.0011(15) C7 0.056(2) 0.047(2) 0.040(2) 0.0065(17) -0.0107(17) -0.0100(18) C8 0.167(5) 0.074(3) 0.045(2) 0.019(2) -0.040(3) -0.016(3) C9 0.183(5) 0.093(4) 0.075(3) 0.024(3) -0.011(3) -0.006(4) C10 0.053(2) 0.045(2) 0.0323(17) 0.0012(16) -0.0039(15) 0.0011(17) C11 0.062(2) 0.0332(17) 0.038(2) -0.0029(15) -0.0008(17) -0.0028(16) C12 0.058(2) 0.0418(18) 0.0327(17) -0.0003(15) -0.0008(16) -0.0076(17) C13 0.073(3) 0.044(2) 0.063(2) 0.0094(18) 0.000(2) -0.0010(19) C14 0.110(4) 0.048(2) 0.076(3) 0.014(2) -0.011(3) -0.001(2) C15 0.138(4) 0.056(3) 0.081(3) 0.028(2) 0.009(3) -0.016(3) C16 0.099(4) 0.086(3) 0.113(4) 0.030(3) 0.029(3) -0.022(3) C17 0.063(3) 0.071(3) 0.072(3) 0.015(2) 0.013(2) -0.004(2) C18 0.052(2) 0.0420(19) 0.0319(17) -0.0011(14) 0.0012(15) -0.0083(16) C19 0.065(2) 0.048(2) 0.0438(19) -0.0039(17) -0.0029(17) -0.0060(18) C20 0.093(3) 0.046(2) 0.054(2) -0.0075(18) 0.001(2) -0.016(2) C21 0.080(3) 0.073(3) 0.060(2) -0.006(2) -0.008(2) -0.035(2) C22 0.060(2) 0.073(3) 0.071(3) 0.002(2) -0.016(2) -0.015(2) C23 0.055(2) 0.054(2) 0.060(2) -0.0023(18) -0.0111(18) -0.0041(18) C24 0.053(2) 0.0408(18) 0.0304(17) 0.0028(15) -0.0029(15) -0.0024(16) C25 0.049(2) 0.0394(18) 0.0348(18) 0.0054(15) -0.0045(15) 0.0024(15) C26 0.056(2) 0.0423(19) 0.0309(17) -0.0009(15) -0.0020(15) 0.0025(16) C27 0.053(2) 0.0412(18) 0.0285(17) 0.0032(14) -0.0033(14) 0.0009(16) C28 0.0456(19) 0.0382(17) 0.0365(18) 0.0064(14) -0.0023(14) -0.0012(15) C29 0.0498(19) 0.0395(18) 0.0310(17) 0.0013(14) -0.0008(14) -0.0009(15) C30 0.064(2) 0.044(2) 0.036(2) 0.0033(17) -0.0037(17) 0.0028(18) C31 0.104(3) 0.078(3) 0.034(2) 0.0039(19) -0.020(2) -0.007(2) C32 0.087(3) 0.087(3) 0.053(2) -0.013(2) -0.009(2) 0.012(2) C33 0.063(2) 0.043(2) 0.0416(19) -0.0005(16) -0.0036(17) 0.0035(18) C34 0.060(2) 0.0403(19) 0.038(2) -0.0008(16) -0.0010(17) 0.0050(16) C35 0.054(2) 0.0375(18) 0.0368(18) -0.0004(15) -0.0104(16) 0.0022(16) C36 0.075(3) 0.044(2) 0.048(2) 0.0101(17) -0.0049(19) 0.0000(18) C37 0.116(4) 0.054(3) 0.072(3) 0.018(2) -0.015(3) -0.005(3) C38 0.111(4) 0.058(3) 0.121(4) 0.021(3) -0.038(3) 0.019(3) C39 0.068(3) 0.079(3) 0.129(4) 0.007(3) -0.016(3) 0.025(3) C40 0.061(3) 0.060(2) 0.079(3) 0.008(2) -0.007(2) 0.009(2) C41 0.049(2) 0.047(2) 0.0345(18) -0.0010(15) -0.0052(15) 0.0038(16) C42 0.062(2) 0.052(2) 0.043(2) -0.0005(17) -0.0055(17) -0.0005(18) C43 0.075(3) 0.051(2) 0.056(2) -0.0102(19) -0.011(2) 0.0041(19) C44 0.077(3) 0.071(3) 0.055(2) -0.021(2) -0.002(2) 0.023(2) C45 0.065(3) 0.085(3) 0.058(2) -0.014(2) 0.0149(19) 0.004(2) C46 0.059(2) 0.057(2) 0.050(2) -0.0055(18) 0.0068(18) -0.0013(18) N1 0.074(2) 0.0520(18) 0.065(2) 0.0152(16) -0.0054(16) -0.0105(16) N2 0.103(2) 0.0429(16) 0.0357(15) 0.0039(13) -0.0132(15) -0.0203(16) N3 0.096(2) 0.0486(17) 0.0378(17) 0.0032(14) -0.0131(16) -0.0035(16) N4 0.092(2) 0.0546(19) 0.070(2) 0.0078(17) -0.0092(18) 0.0187(18) N5 0.093(2) 0.0461(16) 0.0348(15) -0.0027(13) -0.0076(15) 0.0169(16) N6 0.095(2) 0.0536(18) 0.0387(17) -0.0012(14) -0.0086(16) 0.0073(16) O1 0.095(2) 0.0715(17) 0.0414(14) -0.0102(13) 0.0025(13) 0.0036(15) O2 0.0961(19) 0.0537(15) 0.0469(14) 0.0085(12) -0.0184(13) -0.0045(14) O3 0.127(2) 0.0693(17) 0.0463(15) 0.0199(14) -0.0150(15) -0.0262(17) O4 0.0777(16) 0.0625(15) 0.0309(12) 0.0058(11) -0.0119(11) -0.0091(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.398(4) . ? C1 C6 1.394(4) . ? C1 C7 1.500(4) . ? C2 C3 1.409(4) . ? C2 C10 1.428(4) . ? C3 N2 1.349(3) . ? C3 C4 1.397(4) . ? C4 C5 1.402(4) . ? C4 C11 1.444(4) . ? C5 C6 1.405(4) . ? C5 C12 1.495(4) . ? C6 C18 1.495(4) . ? C7 O1 1.215(4) . ? C7 O2 1.310(4) . ? C8 C9 1.390(5) . ? C8 O2 1.507(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N1 1.142(4) . ? C11 N3 1.141(3) . ? C12 C17 1.369(4) . ? C12 C13 1.364(4) . ? C13 C14 1.386(5) . ? C13 H13 0.9300 . ? C14 C15 1.352(5) . ? C14 H14 0.9300 . ? C15 C16 1.374(6) . ? C15 H15 0.9300 . ? C16 C17 1.416(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C23 1.388(4) . ? C18 C19 1.385(4) . ? C19 C20 1.379(4) . ? C19 H19 0.9300 . ? C20 C21 1.372(5) . ? C20 H20 0.9300 . ? C21 C22 1.369(5) . ? C21 H21 0.9300 . ? C22 C23 1.377(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C29 1.389(4) . ? C24 C25 1.396(4) . ? C24 C30 1.498(4) . ? C25 C26 1.410(4) . ? C25 C33 1.440(4) . ? C26 N5 1.348(3) . ? C26 C27 1.412(4) . ? C27 C28 1.404(4) . ? C27 C34 1.435(4) . ? C28 C29 1.407(4) . ? C28 C35 1.488(4) . ? C29 C41 1.489(4) . ? C30 O3 1.196(3) . ? C30 O4 1.319(4) . ? C31 O4 1.466(3) . ? C31 C32 1.470(5) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 N4 1.137(4) . ? C34 N6 1.138(3) . ? C35 C40 1.379(4) . ? C35 C36 1.384(4) . ? C36 C37 1.369(5) . ? C36 H36 0.9300 . ? C37 C38 1.366(6) . ? C37 H37 0.9300 . ? C38 C39 1.370(6) . ? C38 H38 0.9300 . ? C39 C40 1.387(5) . ? C39 H39 0.9300 . ? C40 H40 0.9300 . ? C41 C46 1.383(4) . ? C41 C42 1.397(4) . ? C42 C43 1.381(4) . ? C42 H42 0.9300 . ? C43 C44 1.374(5) . ? C43 H43 0.9300 . ? C44 C45 1.370(5) . ? C44 H44 0.9300 . ? C45 C46 1.384(4) . ? C45 H45 0.9300 . ? C46 H46 0.9300 . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? N5 H5A 0.8600 . ? N5 H5B 0.8600 . ? 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 C1 C6 122.0(3) . . ? C2 C1 C7 118.1(3) . . ? C6 C1 C7 119.1(3) . . ? C1 C2 C3 120.4(3) . . ? C1 C2 C10 122.4(3) . . ? C3 C2 C10 117.2(3) . . ? N2 C3 C4 122.0(3) . . ? N2 C3 C2 121.0(3) . . ? C4 C3 C2 117.0(3) . . ? C3 C4 C5 122.8(3) . . ? C3 C4 C11 117.3(3) . . ? C5 C4 C11 119.9(3) . . ? C4 C5 C6 119.5(3) . . ? C4 C5 C12 118.1(2) . . ? C6 C5 C12 122.4(3) . . ? C1 C6 C5 118.0(3) . . ? C1 C6 C18 120.2(2) . . ? C5 C6 C18 121.8(3) . . ? O1 C7 O2 124.3(3) . . ? O1 C7 C1 122.0(3) . . ? O2 C7 C1 113.5(3) . . ? C9 C8 O2 109.1(4) . . ? C9 C8 H8A 109.9 . . ? O2 C8 H8A 109.9 . . ? C9 C8 H8B 109.9 . . ? O2 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 C2 175.5(3) . . ? N3 C11 C4 175.3(3) . . ? C17 C12 C13 119.4(3) . . ? C17 C12 C5 121.0(3) . . ? C13 C12 C5 119.5(3) . . ? C12 C13 C14 121.9(4) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C15 C14 C13 119.6(4) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 119.6(4) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C17 120.9(4) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C12 C17 C16 118.5(4) . . ? C12 C17 H17 120.8 . . ? C16 C17 H17 120.8 . . ? C23 C18 C19 118.7(3) . . ? C23 C18 C6 119.4(3) . . ? C19 C18 C6 121.9(3) . . ? C20 C19 C18 120.3(3) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 120.4(3) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 119.7(3) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C21 C22 C23 120.5(3) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C18 C23 C22 120.4(3) . . ? C18 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C29 C24 C25 122.3(3) . . ? C29 C24 C30 120.1(3) . . ? C25 C24 C30 117.6(3) . . ? C24 C25 C26 121.0(3) . . ? C24 C25 C33 120.4(3) . . ? C26 C25 C33 118.6(3) . . ? N5 C26 C25 122.0(3) . . ? N5 C26 C27 121.7(3) . . ? C25 C26 C27 116.3(3) . . ? C28 C27 C26 122.7(3) . . ? C28 C27 C34 119.2(3) . . ? C26 C27 C34 118.1(3) . . ? C27 C28 C29 119.6(3) . . ? C27 C28 C35 119.1(2) . . ? C29 C28 C35 121.3(3) . . ? C24 C29 C28 118.1(3) . . ? C24 C29 C41 120.2(3) . . ? C28 C29 C41 121.7(3) . . ? O3 C30 O4 125.1(3) . . ? O3 C30 C24 123.7(3) . . ? O4 C30 C24 111.1(3) . . ? O4 C31 C32 107.7(3) . . ? O4 C31 H31A 110.2 . . ? C32 C31 H31A 110.2 . . ? O4 C31 H31B 110.2 . . ? C32 C31 H31B 110.2 . . ? H31A C31 H31B 108.5 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N4 C33 C25 178.0(4) . . ? N6 C34 C27 178.4(4) . . ? C40 C35 C36 119.0(3) . . ? C40 C35 C28 121.2(3) . . ? C36 C35 C28 119.8(3) . . ? C37 C36 C35 120.8(4) . . ? C37 C36 H36 119.6 . . ? C35 C36 H36 119.6 . . ? C38 C37 C36 120.1(4) . . ? C38 C37 H37 120.0 . . ? C36 C37 H37 120.0 . . ? C39 C38 C37 120.2(4) . . ? C39 C38 H38 119.9 . . ? C37 C38 H38 119.9 . . ? C38 C39 C40 120.1(4) . . ? C38 C39 H39 120.0 . . ? C40 C39 H39 120.0 . . ? C35 C40 C39 119.9(4) . . ? C35 C40 H40 120.0 . . ? C39 C40 H40 120.0 . . ? C46 C41 C42 118.4(3) . . ? C46 C41 C29 119.6(3) . . ? C42 C41 C29 122.0(3) . . ? C43 C42 C41 120.3(3) . . ? C43 C42 H42 119.9 . . ? C41 C42 H42 119.9 . . ? C44 C43 C42 120.2(3) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C45 C44 C43 120.4(3) . . ? C45 C44 H44 119.8 . . ? C43 C44 H44 119.8 . . ? C44 C45 C46 119.7(3) . . ? C44 C45 H45 120.1 . . ? C46 C45 H45 120.1 . . ? C41 C46 C45 121.0(3) . . ? C41 C46 H46 119.5 . . ? C45 C46 H46 119.5 . . ? C3 N2 H2A 120.0 . . ? C3 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C26 N5 H5A 120.0 . . ? C26 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C7 O2 C8 114.3(3) . . ? C30 O4 C31 117.0(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A N6 0.86 2.33 3.103(4) 148.9 1_566 N2 H2B O1 0.86 2.43 3.109(4) 136.1 2_656 N5 H5A N4 0.86 2.47 3.298(4) 161.9 3_745 N5 H5B N3 0.86 2.47 3.265(4) 153.4 1_544 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.282 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.044 #============================================================================= data_1b _database_code_depnum_ccdc_archive 'CCDC 663310' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H21 N3 O2' _chemical_formula_sum 'C25 H21 N3 O2' _chemical_formula_weight 395.45 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7356(11) _cell_length_b 10.7613(15) _cell_length_c 14.462(2) _cell_angle_alpha 68.201(2) _cell_angle_beta 82.240(2) _cell_angle_gamma 73.073(2) _cell_volume 1068.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 4772 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 27.67 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9766 _exptl_absorpt_correction_T_max 0.9843 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7778 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3757 _reflns_number_gt 3164 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0711P)^2^+0.2472P] 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 SHELXL _refine_ls_extinction_coef 0.062(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3757 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1358 _refine_ls_wR_factor_gt 0.1257 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 C1 C -0.09506(19) 0.52610(15) 0.18213(11) 0.0439(4) Uani 1 1 d . . . C2 C -0.16607(19) 0.48433(15) 0.11781(11) 0.0439(4) Uani 1 1 d . . . C3 C -0.0766(2) 0.36064(15) 0.10055(11) 0.0446(4) Uani 1 1 d . . . C4 C 0.08538(19) 0.28181(15) 0.15172(11) 0.0453(4) Uani 1 1 d . . . C5 C 0.15958(19) 0.32495(15) 0.21458(11) 0.0437(4) Uani 1 1 d . . . C6 C 0.06847(19) 0.44998(15) 0.22945(11) 0.0443(4) Uani 1 1 d . . . C7 C -0.2086(2) 0.65107(17) 0.20594(13) 0.0525(4) Uani 1 1 d . . . C8 C -0.3336(4) 0.8939(2) 0.1389(3) 0.1176(11) Uani 1 1 d . . . H8A H -0.4369 0.9253 0.0969 0.141 Uiso 1 1 calc R . . H8B H -0.3783 0.8751 0.2073 0.141 Uiso 1 1 calc R . . C9 C -0.2454(5) 0.9987(3) 0.1124(3) 0.1293(12) Uani 1 1 d . . . H9A H -0.1479 0.9705 0.1565 0.194 Uiso 1 1 calc R . . H9B H -0.3293 1.0818 0.1173 0.194 Uiso 1 1 calc R . . H9C H -0.1983 1.0161 0.0452 0.194 Uiso 1 1 calc R . . C10 C -0.3346(2) 0.56431(16) 0.07022(12) 0.0495(4) Uani 1 1 d . . . C11 C 0.1705(2) 0.15216(18) 0.13695(13) 0.0570(4) Uani 1 1 d . . . C12 C 0.33308(19) 0.23684(15) 0.26438(11) 0.0445(4) Uani 1 1 d . . . C13 C 0.3535(2) 0.09804(17) 0.32282(12) 0.0536(4) Uani 1 1 d . . . H13 H 0.2573 0.0589 0.3314 0.064 Uiso 1 1 calc R . . C14 C 0.5150(2) 0.01722(18) 0.36842(13) 0.0613(5) Uani 1 1 d . . . H14 H 0.5251 -0.0752 0.4076 0.074 Uiso 1 1 calc R . . C15 C 0.6618(2) 0.07138(19) 0.35677(12) 0.0582(4) Uani 1 1 d . . . C16 C 0.6404(2) 0.20961(19) 0.29960(12) 0.0578(4) Uani 1 1 d . . . H16 H 0.7365 0.2486 0.2916 0.069 Uiso 1 1 calc R . . C17 C 0.4797(2) 0.29160(17) 0.25383(12) 0.0526(4) Uani 1 1 d . . . H17 H 0.4696 0.3844 0.2156 0.063 Uiso 1 1 calc R . . C18 C 0.8398(3) -0.0182(3) 0.40423(18) 0.0885(7) Uani 1 1 d . . . H18A H 0.8174 -0.0777 0.4704 0.133 Uiso 1 1 calc R . . H18B H 0.9110 0.0399 0.4072 0.133 Uiso 1 1 calc R . . H18C H 0.9040 -0.0735 0.3652 0.133 Uiso 1 1 calc R . . C19 C 0.13817(19) 0.50391(15) 0.29445(11) 0.0465(4) Uani 1 1 d . . . C20 C 0.1590(2) 0.43103(18) 0.39571(12) 0.0545(4) Uani 1 1 d . . . H20 H 0.1354 0.3444 0.4235 0.065 Uiso 1 1 calc R . . C21 C 0.2144(2) 0.4859(2) 0.45590(14) 0.0638(5) Uani 1 1 d . . . H21 H 0.2280 0.4352 0.5236 0.077 Uiso 1 1 calc R . . C22 C 0.2499(2) 0.6143(2) 0.41729(15) 0.0649(5) Uani 1 1 d . . . C23 C 0.2322(3) 0.6861(2) 0.31574(16) 0.0690(5) Uani 1 1 d . . . H23 H 0.2575 0.7721 0.2880 0.083 Uiso 1 1 calc R . . C24 C 0.1775(2) 0.63197(18) 0.25497(14) 0.0594(4) Uani 1 1 d . . . H24 H 0.1670 0.6818 0.1870 0.071 Uiso 1 1 calc R . . C25 C 0.3040(4) 0.6751(3) 0.4850(2) 0.0990(8) Uani 1 1 d . . . H25A H 0.2075 0.7523 0.4899 0.149 Uiso 1 1 calc R . . H25B H 0.4108 0.7058 0.4577 0.149 Uiso 1 1 calc R . . H25C H 0.3278 0.6055 0.5500 0.149 Uiso 1 1 calc R . . N1 N -0.4697(2) 0.62313(16) 0.03222(13) 0.0677(4) Uani 1 1 d . . . N2 N -0.14184(19) 0.31847(15) 0.03828(11) 0.0568(4) Uani 1 1 d . . . H2A H -0.2407 0.3678 0.0080 0.068 Uiso 1 1 calc R . . H2B H -0.0845 0.2424 0.0290 0.068 Uiso 1 1 calc R . . N3 N 0.2242(3) 0.04929(19) 0.12341(15) 0.0834(6) Uani 1 1 d . . . O1 O -0.2839(2) 0.64357(16) 0.28428(11) 0.0898(5) Uani 1 1 d . . . O2 O -0.21523(18) 0.76606(12) 0.12868(11) 0.0718(4) 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 C1 0.0410(8) 0.0413(8) 0.0435(8) -0.0087(6) -0.0046(6) -0.0085(6) C2 0.0372(7) 0.0430(8) 0.0438(8) -0.0070(6) -0.0062(6) -0.0079(6) C3 0.0412(8) 0.0453(8) 0.0430(8) -0.0094(6) -0.0044(6) -0.0118(6) C4 0.0398(8) 0.0433(8) 0.0476(8) -0.0130(6) -0.0045(6) -0.0058(6) C5 0.0378(8) 0.0452(8) 0.0423(8) -0.0094(6) -0.0026(6) -0.0095(6) C6 0.0403(8) 0.0441(8) 0.0436(8) -0.0102(6) -0.0048(6) -0.0092(6) C7 0.0436(8) 0.0538(9) 0.0565(10) -0.0198(8) -0.0118(7) -0.0022(7) C8 0.0945(18) 0.0503(12) 0.183(3) -0.0409(16) 0.0146(18) 0.0091(12) C9 0.159(3) 0.0823(17) 0.174(3) -0.080(2) 0.032(2) -0.0416(19) C10 0.0460(9) 0.0445(8) 0.0543(9) -0.0126(7) -0.0102(7) -0.0088(7) C11 0.0495(9) 0.0574(10) 0.0604(10) -0.0227(8) -0.0143(7) -0.0002(8) C12 0.0367(8) 0.0485(8) 0.0434(8) -0.0139(6) -0.0042(6) -0.0057(6) C13 0.0456(9) 0.0504(9) 0.0592(10) -0.0108(7) -0.0094(7) -0.0119(7) C14 0.0557(10) 0.0506(9) 0.0623(10) -0.0048(8) -0.0157(8) -0.0048(8) C15 0.0434(9) 0.0686(11) 0.0508(9) -0.0152(8) -0.0099(7) -0.0011(8) C16 0.0389(8) 0.0732(11) 0.0572(10) -0.0163(8) -0.0034(7) -0.0165(8) C17 0.0433(8) 0.0523(9) 0.0535(9) -0.0089(7) -0.0044(7) -0.0110(7) C18 0.0530(11) 0.0995(16) 0.0874(15) -0.0125(13) -0.0248(10) 0.0013(11) C19 0.0376(8) 0.0469(8) 0.0516(8) -0.0160(7) -0.0081(6) -0.0047(6) C20 0.0520(9) 0.0568(9) 0.0521(9) -0.0169(7) -0.0071(7) -0.0108(7) C21 0.0574(10) 0.0768(12) 0.0568(10) -0.0270(9) -0.0143(8) -0.0064(9) C22 0.0475(9) 0.0730(12) 0.0833(13) -0.0399(10) -0.0171(9) -0.0059(8) C23 0.0623(11) 0.0588(10) 0.0919(14) -0.0274(10) -0.0144(10) -0.0179(9) C24 0.0587(10) 0.0545(10) 0.0616(10) -0.0139(8) -0.0110(8) -0.0144(8) C25 0.0902(16) 0.1054(18) 0.128(2) -0.0677(17) -0.0389(15) -0.0128(14) N1 0.0540(9) 0.0594(9) 0.0843(11) -0.0209(8) -0.0297(8) -0.0004(7) N2 0.0514(8) 0.0562(8) 0.0644(9) -0.0253(7) -0.0179(6) -0.0035(6) N3 0.0818(12) 0.0698(11) 0.0993(14) -0.0459(10) -0.0275(10) 0.0114(9) O1 0.0865(10) 0.0913(11) 0.0663(9) -0.0296(8) 0.0033(8) 0.0142(8) O2 0.0673(8) 0.0418(6) 0.0887(9) -0.0159(6) 0.0010(7) 0.0011(6) _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 C6 1.398(2) . ? C1 C2 1.400(2) . ? C1 C7 1.508(2) . ? C2 C3 1.406(2) . ? C2 C10 1.436(2) . ? C3 N2 1.3532(19) . ? C3 C4 1.415(2) . ? C4 C5 1.408(2) . ? C4 C11 1.440(2) . ? C5 C6 1.405(2) . ? C5 C12 1.4939(19) . ? C6 C19 1.495(2) . ? C7 O1 1.188(2) . ? C7 O2 1.317(2) . ? C8 C9 1.393(4) . ? C8 O2 1.460(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N1 1.143(2) . ? C11 N3 1.144(2) . ? C12 C13 1.390(2) . ? C12 C17 1.390(2) . ? C13 C14 1.384(2) . ? C13 H13 0.9300 . ? C14 C15 1.385(3) . ? C14 H14 0.9300 . ? C15 C16 1.380(3) . ? C15 C18 1.512(2) . ? C16 C17 1.383(2) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.387(2) . ? C19 C24 1.389(2) . ? C20 C21 1.386(2) . ? C20 H20 0.9300 . ? C21 C22 1.379(3) . ? C21 H21 0.9300 . ? C22 C23 1.386(3) . ? C22 C25 1.519(3) . ? C23 C24 1.383(3) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? 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 C6 C1 C2 122.05(14) . . ? C6 C1 C7 120.11(13) . . ? C2 C1 C7 117.65(13) . . ? C1 C2 C3 120.71(13) . . ? C1 C2 C10 120.96(14) . . ? C3 C2 C10 118.30(13) . . ? N2 C3 C2 121.84(13) . . ? N2 C3 C4 121.43(14) . . ? C2 C3 C4 116.73(13) . . ? C5 C4 C3 122.77(13) . . ? C5 C4 C11 121.24(13) . . ? C3 C4 C11 115.98(13) . . ? C6 C5 C4 119.25(13) . . ? C6 C5 C12 121.34(13) . . ? C4 C5 C12 119.41(13) . . ? C1 C6 C5 118.42(13) . . ? C1 C6 C19 118.81(13) . . ? C5 C6 C19 122.77(13) . . ? O1 C7 O2 125.60(16) . . ? O1 C7 C1 123.17(16) . . ? O2 C7 C1 111.21(14) . . ? C9 C8 O2 112.2(2) . . ? C9 C8 H8A 109.2 . . ? O2 C8 H8A 109.2 . . ? C9 C8 H8B 109.2 . . ? O2 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 C2 177.22(17) . . ? N3 C11 C4 174.28(19) . . ? C13 C12 C17 117.77(14) . . ? C13 C12 C5 121.39(13) . . ? C17 C12 C5 120.84(13) . . ? C14 C13 C12 120.93(15) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 121.26(16) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C16 C15 C14 117.63(15) . . ? C16 C15 C18 121.20(17) . . ? C14 C15 C18 121.17(17) . . ? C15 C16 C17 121.69(16) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C16 C17 C12 120.71(15) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 118.17(15) . . ? C20 C19 C6 121.42(14) . . ? C24 C19 C6 120.36(14) . . ? C21 C20 C19 120.71(17) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C22 C21 C20 121.24(17) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 118.04(16) . . ? C21 C22 C25 120.5(2) . . ? C23 C22 C25 121.4(2) . . ? C24 C23 C22 121.16(18) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 C19 120.66(17) . . ? C23 C24 H24 119.7 . . ? C19 C24 H24 119.7 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C3 N2 H2A 120.0 . . ? C3 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C7 O2 C8 116.84(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A N1 0.86 2.36 3.117(2) 147.8 2_465 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.184 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.047 #============================================================================= data_1c _database_code_depnum_ccdc_archive 'CCDC 663311' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 Cl2 N3 O2' _chemical_formula_sum 'C23 H15 Cl2 N3 O2' _chemical_formula_weight 436.28 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' I I -0.4742 1.8119 '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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6007(9) _cell_length_b 10.6932(13) _cell_length_c 14.3335(17) _cell_angle_alpha 68.7230(10) _cell_angle_beta 85.5190(10) _cell_angle_gamma 74.0030(10) _cell_volume 1043.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 4657 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 28.48 _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9059 _exptl_absorpt_correction_T_max 0.9358 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7580 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3668 _reflns_number_gt 3117 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0615P)^2^+0.4735P] 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 3668 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1131 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 Cl1 Cl -0.37531(8) 1.12589(8) 0.41516(5) 0.0776(2) Uani 1 1 d . . . Cl2 Cl 0.19250(10) 0.31294(7) 0.49501(6) 0.0836(2) Uani 1 1 d . . . C1 C 0.5891(2) 0.7916(2) 0.18498(14) 0.0425(4) Uani 1 1 d . . . C2 C 0.6612(2) 0.8983(2) 0.12011(14) 0.0416(4) Uani 1 1 d . . . C3 C 0.5723(2) 1.0384(2) 0.10366(14) 0.0423(4) Uani 1 1 d . . . C4 C 0.4095(2) 1.06509(19) 0.15646(14) 0.0423(4) Uani 1 1 d . . . C5 C 0.3345(2) 0.95926(19) 0.22028(13) 0.0408(4) Uani 1 1 d . . . C6 C 0.4247(2) 0.8193(2) 0.23398(13) 0.0414(4) Uani 1 1 d . . . C7 C 0.7021(3) 0.6437(2) 0.20666(16) 0.0515(5) Uani 1 1 d . . . C8 C 0.8281(5) 0.4718(4) 0.1354(4) 0.1162(13) Uani 1 1 d . . . H8A H 0.9259 0.4850 0.0882 0.139 Uiso 1 1 calc R . . H8B H 0.8832 0.4257 0.2022 0.139 Uiso 1 1 calc R . . C9 C 0.7394(6) 0.3883(3) 0.1168(4) 0.1410(18) Uani 1 1 d . . . H9A H 0.6530 0.3649 0.1684 0.212 Uiso 1 1 calc R . . H9B H 0.8268 0.3047 0.1158 0.212 Uiso 1 1 calc R . . H9C H 0.6761 0.4364 0.0531 0.212 Uiso 1 1 calc R . . C10 C 0.8313(3) 0.8662(2) 0.07103(15) 0.0480(5) Uani 1 1 d . . . C11 C 0.3244(3) 1.2092(2) 0.14157(16) 0.0518(5) Uani 1 1 d . . . C12 C 0.1604(2) 0.99708(19) 0.27156(13) 0.0408(4) Uani 1 1 d . . . C13 C 0.1434(3) 1.0792(2) 0.32986(15) 0.0483(5) Uani 1 1 d . . . H13 H 0.2433 1.1085 0.3386 0.058 Uiso 1 1 calc R . . C14 C -0.0201(3) 1.1180(2) 0.37496(16) 0.0530(5) Uani 1 1 d . . . H14 H -0.0305 1.1730 0.4137 0.064 Uiso 1 1 calc R . . C15 C -0.1671(3) 1.0739(2) 0.36169(15) 0.0497(5) Uani 1 1 d . . . C16 C -0.1538(3) 0.9903(2) 0.30655(15) 0.0505(5) Uani 1 1 d . . . H16 H -0.2534 0.9595 0.2996 0.061 Uiso 1 1 calc R . . C17 C 0.0102(3) 0.9524(2) 0.26124(15) 0.0480(5) Uani 1 1 d . . . H17 H 0.0198 0.8963 0.2234 0.058 Uiso 1 1 calc R . . C18 C 0.3534(2) 0.69976(19) 0.29910(14) 0.0431(4) Uani 1 1 d . . . C19 C 0.3326(3) 0.6710(2) 0.40101(15) 0.0486(5) Uani 1 1 d . . . H19 H 0.3550 0.7308 0.4294 0.058 Uiso 1 1 calc R . . C20 C 0.2789(3) 0.5537(2) 0.46110(16) 0.0547(5) Uani 1 1 d . . . H20 H 0.2640 0.5352 0.5294 0.066 Uiso 1 1 calc R . . C21 C 0.2479(3) 0.4654(2) 0.41848(18) 0.0557(5) Uani 1 1 d . . . C22 C 0.2626(3) 0.4928(2) 0.31692(19) 0.0604(6) Uani 1 1 d . . . H22 H 0.2381 0.4332 0.2889 0.072 Uiso 1 1 calc R . . C23 C 0.3144(3) 0.6106(2) 0.25757(17) 0.0546(5) Uani 1 1 d . . . H23 H 0.3234 0.6308 0.1888 0.065 Uiso 1 1 calc R . . N1 N 0.9676(3) 0.8459(2) 0.03230(17) 0.0682(5) Uani 1 1 d . . . N2 N 0.6391(2) 1.14295(18) 0.04055(13) 0.0544(4) Uani 1 1 d . . . H2A H 0.7384 1.1243 0.0093 0.065 Uiso 1 1 calc R . . H2B H 0.5821 1.2281 0.0317 0.065 Uiso 1 1 calc R . . N3 N 0.2702(3) 1.3254(2) 0.12687(18) 0.0773(6) Uani 1 1 d . . . O1 O 0.7789(3) 0.5722(2) 0.28415(14) 0.0912(6) Uani 1 1 d . . . O2 O 0.7078(2) 0.60743(17) 0.12779(14) 0.0715(5) 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 Cl1 0.0448(3) 0.1121(5) 0.0849(4) -0.0525(4) 0.0253(3) -0.0176(3) Cl2 0.0797(5) 0.0648(4) 0.0990(5) -0.0130(3) 0.0245(4) -0.0356(3) C1 0.0396(9) 0.0481(10) 0.0419(10) -0.0204(8) 0.0042(8) -0.0096(8) C2 0.0347(9) 0.0524(11) 0.0424(10) -0.0227(8) 0.0061(7) -0.0122(8) C3 0.0377(9) 0.0519(11) 0.0406(9) -0.0193(8) 0.0046(7) -0.0141(8) C4 0.0367(9) 0.0457(10) 0.0449(10) -0.0182(8) 0.0036(8) -0.0094(8) C5 0.0352(9) 0.0491(10) 0.0404(9) -0.0190(8) 0.0024(7) -0.0110(8) C6 0.0378(9) 0.0478(10) 0.0406(9) -0.0189(8) 0.0038(7) -0.0109(8) C7 0.0422(10) 0.0530(12) 0.0542(12) -0.0186(10) 0.0107(9) -0.0081(9) C8 0.096(2) 0.085(2) 0.176(4) -0.086(3) -0.014(2) 0.0213(18) C9 0.150(4) 0.0563(18) 0.221(5) -0.056(3) -0.050(3) -0.009(2) C10 0.0449(11) 0.0513(11) 0.0529(11) -0.0242(9) 0.0103(9) -0.0157(9) C11 0.0448(11) 0.0512(12) 0.0550(12) -0.0176(9) 0.0132(9) -0.0109(9) C12 0.0353(9) 0.0444(10) 0.0406(9) -0.0153(8) 0.0039(7) -0.0078(7) C13 0.0413(10) 0.0574(12) 0.0539(11) -0.0264(9) 0.0085(8) -0.0182(9) C14 0.0492(11) 0.0634(13) 0.0556(12) -0.0326(10) 0.0133(9) -0.0170(10) C15 0.0378(10) 0.0602(12) 0.0462(11) -0.0185(9) 0.0089(8) -0.0082(9) C16 0.0354(10) 0.0646(13) 0.0535(11) -0.0210(10) 0.0029(8) -0.0168(9) C17 0.0401(10) 0.0580(12) 0.0511(11) -0.0267(9) 0.0018(8) -0.0117(9) C18 0.0357(9) 0.0444(10) 0.0470(10) -0.0164(8) 0.0066(8) -0.0086(8) C19 0.0457(11) 0.0517(11) 0.0486(11) -0.0202(9) 0.0051(8) -0.0110(9) C20 0.0496(11) 0.0566(12) 0.0486(11) -0.0121(10) 0.0109(9) -0.0111(9) C21 0.0418(11) 0.0497(11) 0.0694(14) -0.0150(10) 0.0129(10) -0.0142(9) C22 0.0594(13) 0.0591(13) 0.0726(15) -0.0304(11) 0.0106(11) -0.0243(11) C23 0.0566(12) 0.0615(13) 0.0519(12) -0.0253(10) 0.0099(9) -0.0209(10) N1 0.0535(11) 0.0727(13) 0.0868(14) -0.0401(11) 0.0319(10) -0.0223(9) N2 0.0498(10) 0.0507(10) 0.0614(11) -0.0192(8) 0.0185(8) -0.0169(8) N3 0.0759(14) 0.0523(12) 0.0908(16) -0.0219(11) 0.0247(12) -0.0081(10) O1 0.0910(14) 0.0818(12) 0.0640(11) -0.0161(10) -0.0043(10) 0.0231(10) O2 0.0694(10) 0.0630(10) 0.0862(12) -0.0463(9) -0.0019(9) 0.0040(8) _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 Cl1 C15 1.7423(19) . ? Cl2 C21 1.745(2) . ? C1 C2 1.401(3) . ? C1 C6 1.397(3) . ? C1 C7 1.507(3) . ? C2 C3 1.402(3) . ? C2 C10 1.440(3) . ? C3 N2 1.354(2) . ? C3 C4 1.415(3) . ? C4 C5 1.402(3) . ? C4 C11 1.439(3) . ? C5 C6 1.411(3) . ? C5 C12 1.491(2) . ? C6 C18 1.495(3) . ? C7 O1 1.182(3) . ? C7 O2 1.316(3) . ? C8 C9 1.362(5) . ? C8 O2 1.456(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N1 1.141(3) . ? C11 N3 1.141(3) . ? C12 C17 1.390(3) . ? C12 C13 1.393(3) . ? C13 C14 1.385(3) . ? C13 H13 0.9300 . ? C14 C15 1.377(3) . ? C14 H14 0.9300 . ? C15 C16 1.372(3) . ? C16 C17 1.388(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.385(3) . ? C18 C23 1.395(3) . ? C19 C20 1.387(3) . ? C19 H19 0.9300 . ? C20 C21 1.373(3) . ? C20 H20 0.9300 . ? C21 C22 1.378(3) . ? C22 C23 1.381(3) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? 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 C1 C6 121.95(17) . . ? C2 C1 C7 117.60(16) . . ? C6 C1 C7 120.30(17) . . ? C3 C2 C1 120.88(16) . . ? C3 C2 C10 118.50(17) . . ? C1 C2 C10 120.59(17) . . ? N2 C3 C2 121.72(17) . . ? N2 C3 C4 121.60(17) . . ? C2 C3 C4 116.69(17) . . ? C5 C4 C3 122.91(17) . . ? C5 C4 C11 121.29(17) . . ? C3 C4 C11 115.80(17) . . ? C4 C5 C6 119.24(16) . . ? C4 C5 C12 119.31(16) . . ? C6 C5 C12 121.45(16) . . ? C1 C6 C5 118.26(17) . . ? C1 C6 C18 118.71(16) . . ? C5 C6 C18 123.03(16) . . ? O1 C7 O2 125.2(2) . . ? O1 C7 C1 123.6(2) . . ? O2 C7 C1 111.24(18) . . ? C9 C8 O2 113.0(3) . . ? C9 C8 H8A 109.0 . . ? O2 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? O2 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 C2 177.0(2) . . ? N3 C11 C4 174.4(2) . . ? C17 C12 C13 118.40(17) . . ? C17 C12 C5 120.63(16) . . ? C13 C12 C5 120.97(16) . . ? C14 C13 C12 120.95(18) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C13 119.10(19) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C16 C15 C14 121.41(18) . . ? C16 C15 Cl1 119.09(15) . . ? C14 C15 Cl1 119.50(16) . . ? C15 C16 C17 119.19(18) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C16 C17 C12 120.93(18) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? C19 C18 C23 118.72(18) . . ? C19 C18 C6 121.72(17) . . ? C23 C18 C6 119.50(17) . . ? C18 C19 C20 120.66(19) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 119.2(2) . . ? C21 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? C20 C21 C22 121.6(2) . . ? C20 C21 Cl2 119.21(18) . . ? C22 C21 Cl2 119.13(18) . . ? C21 C22 C23 118.7(2) . . ? C21 C22 H22 120.6 . . ? C23 C22 H22 120.6 . . ? C22 C23 C18 121.0(2) . . ? C22 C23 H23 119.5 . . ? C18 C23 H23 119.5 . . ? C3 N2 H2A 120.0 . . ? C3 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C7 O2 C8 116.8(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A N1 0.86 2.34 3.108(3) 148.1 2_775 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.238 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.042 #============================================================================= data_i0377 # no. 1h in publication _database_code_depnum_ccdc_archive 'CCDC 663312' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H33 N3 O2, C H Cl3' _chemical_formula_sum 'C32 H34 Cl3 N3 O2' _chemical_formula_weight 598.97 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' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9457(13) _cell_length_b 14.0078(17) _cell_length_c 15.333(2) _cell_angle_alpha 104.185(10) _cell_angle_beta 103.448(12) _cell_angle_gamma 90.181(12) _cell_volume 1605.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 5916 _cell_measurement_theta_min 1.41 _cell_measurement_theta_max 25.27 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.317 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9070 _exptl_absorpt_correction_T_max 0.9902 _exptl_absorpt_process_details 'X-red ver. 1.06 (Stoe & Cie. 2001)' _exptl_special_details ; ? ; _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_voltage 50 _diffrn_source_current 32 _diffrn_source_power 1.60 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_ambient_temperature 133(2) _diffrn_measurement_method 'rotation method' _diffrn_measurement_details ; 232 frames, detector distance = 135 mm ; _diffrn_standards_decay_% none _diffrn_reflns_number 13428 _diffrn_reflns_av_R_equivalents 0.1415 _diffrn_reflns_av_sigmaI/netI 0.1785 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5516 _reflns_number_gt 2406 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0673P)^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 5516 _refine_ls_number_parameters 375 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1328 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1640 _refine_ls_wR_factor_gt 0.1457 _refine_ls_goodness_of_fit_ref 0.776 _refine_ls_restrained_S_all 0.776 _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 C1 C 0.5193(6) 0.1221(3) 0.6797(3) 0.0360(11) Uani 1 1 d . . . C2 C 0.3874(6) 0.0910(3) 0.5974(3) 0.0349(11) Uani 1 1 d . . . C3 C 0.4056(6) 0.1097(3) 0.5130(3) 0.0364(11) Uani 1 1 d . . . C4 C 0.5603(6) 0.1642(3) 0.5172(3) 0.0361(11) Uani 1 1 d . . . C5 C 0.6859(6) 0.2042(3) 0.6010(3) 0.0390(11) Uani 1 1 d . . . C6 C 0.6661(6) 0.1813(3) 0.6842(3) 0.0366(11) Uani 1 1 d . . . C7 C 0.2295(7) 0.0388(3) 0.5989(3) 0.0388(11) Uani 1 1 d . . . C8 C 0.5782(6) 0.1849(3) 0.4318(3) 0.0392(11) Uani 1 1 d . . . C9 C 0.8343(6) 0.2697(3) 0.6029(3) 0.0369(11) Uani 1 1 d . . . C10 C 0.9534(6) 0.2393(3) 0.5480(3) 0.0390(11) Uani 1 1 d . . . H10A H 0.9359 0.1758 0.5060 0.047 Uiso 1 1 calc R . . C11 C 1.0958(6) 0.3003(3) 0.5540(3) 0.0400(11) Uani 1 1 d . . . H11A H 1.1747 0.2769 0.5168 0.048 Uiso 1 1 calc R . . C12 C 1.1270(6) 0.3961(3) 0.6137(3) 0.0365(11) Uani 1 1 d . . . C13 C 1.0044(6) 0.4263(3) 0.6674(3) 0.0420(12) Uani 1 1 d . . . H13A H 1.0197 0.4907 0.7079 0.050 Uiso 1 1 calc R . . C14 C 0.8657(6) 0.3667(3) 0.6633(3) 0.0416(12) Uani 1 1 d . . . H14A H 0.7881 0.3901 0.7013 0.050 Uiso 1 1 calc R . . C15 C 1.2852(6) 0.4654(3) 0.6237(3) 0.0452(12) Uani 1 1 d . . . C16 C 1.4077(7) 0.4155(4) 0.5637(4) 0.0621(16) Uani 1 1 d . . . H16A H 1.3497 0.4048 0.4979 0.074 Uiso 1 1 calc R . . H16B H 1.4375 0.3519 0.5772 0.074 Uiso 1 1 calc R . . H16C H 1.5137 0.4581 0.5779 0.074 Uiso 1 1 calc R . . C17 C 1.2223(7) 0.5591(3) 0.5940(4) 0.0597(15) Uani 1 1 d . . . H17A H 1.1421 0.5902 0.6307 0.072 Uiso 1 1 calc R . . H17B H 1.1627 0.5415 0.5281 0.072 Uiso 1 1 calc R . . H17C H 1.3220 0.6053 0.6044 0.072 Uiso 1 1 calc R . . C18 C 1.3890(7) 0.4936(4) 0.7246(3) 0.0677(17) Uani 1 1 d . . . H18C H 1.4867 0.5398 0.7313 0.081 Uiso 1 1 calc R . . H18B H 1.4327 0.4342 0.7426 0.081 Uiso 1 1 calc R . . H18A H 1.3140 0.5248 0.7644 0.081 Uiso 1 1 calc R . . C19 C 0.7976(6) 0.2195(3) 0.7752(3) 0.0381(11) Uani 1 1 d . . . C20 C 0.7465(6) 0.2799(3) 0.8505(3) 0.0397(11) Uani 1 1 d . . . H20A H 0.6282 0.2941 0.8447 0.048 Uiso 1 1 calc R . . C21 C 0.8674(6) 0.3197(3) 0.9341(3) 0.0393(11) Uani 1 1 d . . . H21A H 0.8304 0.3613 0.9842 0.047 Uiso 1 1 calc R . . C22 C 1.0422(6) 0.2991(3) 0.9451(3) 0.0404(12) Uani 1 1 d . . . C23 C 1.0900(6) 0.2368(3) 0.8687(3) 0.0450(12) Uani 1 1 d . . . H23A H 1.2077 0.2214 0.8742 0.054 Uiso 1 1 calc R . . C24 C 0.9699(6) 0.1974(3) 0.7861(3) 0.0413(12) Uani 1 1 d . . . H24A H 1.0060 0.1547 0.7363 0.050 Uiso 1 1 calc R . . C25 C 1.1855(6) 0.3423(3) 1.0351(3) 0.0483(13) Uani 1 1 d . . . C26 C 1.3272(7) 0.3992(4) 1.0123(3) 0.0629(16) Uani 1 1 d . . . H26A H 1.2759 0.4511 0.9839 0.076 Uiso 1 1 calc R . . H26B H 1.3818 0.3538 0.9691 0.076 Uiso 1 1 calc R . . H26C H 1.4148 0.4290 1.0694 0.076 Uiso 1 1 calc R . . C27 C 1.1098(7) 0.4138(3) 1.1085(3) 0.0530(14) Uani 1 1 d . . . H27A H 1.0218 0.3777 1.1256 0.064 Uiso 1 1 calc R . . H27B H 1.0568 0.4671 1.0828 0.064 Uiso 1 1 calc R . . H27C H 1.2030 0.4417 1.1636 0.064 Uiso 1 1 calc R . . C28 C 1.2604(7) 0.2576(4) 1.0745(3) 0.0636(16) Uani 1 1 d . . . H28A H 1.3170 0.2148 1.0306 0.076 Uiso 1 1 calc R . . H28B H 1.1668 0.2193 1.0850 0.076 Uiso 1 1 calc R . . H28C H 1.3455 0.2841 1.1334 0.076 Uiso 1 1 calc R . . C29 C 0.5033(6) 0.0866(3) 0.7621(3) 0.0408(12) Uani 1 1 d . . . C30 C 0.6124(7) -0.0263(3) 0.8518(3) 0.0529(14) Uani 1 1 d . . . H30B H 0.6583 -0.0926 0.8394 0.063 Uiso 1 1 calc R . . H30A H 0.4916 -0.0339 0.8571 0.063 Uiso 1 1 calc R . . C31 C 0.7217(9) 0.0381(5) 0.9418(3) 0.081(2) Uani 1 1 d . . . H31C H 0.7195 0.0075 0.9926 0.097 Uiso 1 1 calc R . . H31B H 0.6749 0.1033 0.9544 0.097 Uiso 1 1 calc R . . H31A H 0.8415 0.0450 0.9365 0.097 Uiso 1 1 calc R . . C32 C 1.0921(7) -0.1872(4) 0.7480(3) 0.0597(15) Uani 1 1 d . . . H32A H 1.1511 -0.1910 0.6964 0.072 Uiso 1 1 calc R . . N1 N 0.2828(6) 0.0755(3) 0.4332(3) 0.0424(11) Uani 1 1 d D . . H1 H 0.190(7) 0.056(4) 0.430(3) 0.049(11) Uiso 1 1 d D . . H2 H 0.273(7) 0.104(4) 0.394(3) 0.049(11) Uiso 1 1 d D . . N2 N 0.5816(5) 0.1962(3) 0.3606(3) 0.0486(11) Uani 1 1 d . . . N3 N 0.1014(6) -0.0001(3) 0.5981(2) 0.0463(10) Uani 1 1 d . . . O1 O 0.3983(5) 0.1132(2) 0.8078(2) 0.0587(10) Uani 1 1 d . . . O2 O 0.6151(4) 0.0183(2) 0.77509(18) 0.0441(8) Uani 1 1 d . . . Cl1 Cl 1.0548(2) -0.06265(10) 0.79274(10) 0.0754(5) Uani 1 1 d . . . Cl2 Cl 1.2272(2) -0.23400(10) 0.83389(10) 0.0693(4) Uani 1 1 d . . . Cl3 Cl 0.8903(2) -0.25819(11) 0.70246(9) 0.0677(4) 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 C1 0.040(3) 0.032(2) 0.030(2) -0.0014(18) 0.0054(19) 0.005(2) C2 0.039(3) 0.030(2) 0.030(2) -0.0004(17) 0.0041(19) 0.002(2) C3 0.046(3) 0.030(2) 0.026(2) -0.0039(17) 0.006(2) 0.005(2) C4 0.042(3) 0.032(2) 0.028(2) -0.0002(18) 0.0040(19) 0.003(2) C5 0.048(3) 0.032(2) 0.029(2) -0.0086(18) 0.010(2) 0.003(2) C6 0.044(3) 0.032(2) 0.027(2) -0.0041(17) 0.0069(19) 0.003(2) C7 0.054(3) 0.035(2) 0.020(2) -0.0044(18) 0.008(2) 0.005(2) C8 0.039(3) 0.035(2) 0.032(3) -0.0019(19) -0.002(2) -0.002(2) C9 0.044(3) 0.029(2) 0.032(2) -0.0008(18) 0.006(2) -0.004(2) C10 0.043(3) 0.035(2) 0.031(2) -0.0038(18) 0.005(2) -0.004(2) C11 0.046(3) 0.035(2) 0.035(2) -0.0015(19) 0.013(2) 0.004(2) C12 0.037(3) 0.035(2) 0.030(2) 0.0000(18) 0.004(2) 0.001(2) C13 0.053(3) 0.031(2) 0.033(2) -0.0062(18) 0.008(2) 0.000(2) C14 0.055(3) 0.034(2) 0.029(2) -0.0061(18) 0.011(2) 0.001(2) C15 0.046(3) 0.041(3) 0.041(2) 0.000(2) 0.008(2) -0.006(2) C16 0.051(3) 0.048(3) 0.082(4) -0.001(3) 0.023(3) -0.008(3) C17 0.059(3) 0.044(3) 0.073(3) 0.009(3) 0.016(3) -0.010(3) C18 0.056(3) 0.080(4) 0.053(3) 0.005(3) -0.001(3) -0.023(3) C19 0.045(3) 0.033(2) 0.026(2) -0.0053(18) 0.0024(19) -0.007(2) C20 0.043(3) 0.034(2) 0.035(2) -0.0010(19) 0.007(2) 0.001(2) C21 0.051(3) 0.037(2) 0.023(2) -0.0026(18) 0.005(2) 0.003(2) C22 0.048(3) 0.035(2) 0.029(2) -0.0051(18) 0.005(2) 0.000(2) C23 0.041(3) 0.046(3) 0.037(2) -0.003(2) 0.003(2) 0.009(2) C24 0.050(3) 0.036(2) 0.031(2) -0.0056(19) 0.009(2) 0.002(2) C25 0.053(3) 0.048(3) 0.027(2) -0.005(2) -0.007(2) -0.001(3) C26 0.058(3) 0.068(3) 0.046(3) -0.008(3) 0.003(3) -0.008(3) C27 0.058(3) 0.051(3) 0.030(2) -0.011(2) -0.006(2) 0.005(3) C28 0.071(4) 0.066(3) 0.037(3) -0.007(3) 0.000(3) 0.012(3) C29 0.043(3) 0.034(2) 0.033(2) -0.0059(19) 0.001(2) -0.003(2) C30 0.075(4) 0.043(3) 0.038(3) 0.012(2) 0.005(3) 0.013(3) C31 0.105(5) 0.084(4) 0.037(3) 0.001(3) 0.002(3) -0.006(4) C32 0.061(4) 0.070(3) 0.042(3) 0.003(2) 0.014(3) -0.006(3) N1 0.045(3) 0.044(2) 0.029(2) 0.0021(18) -0.001(2) -0.005(2) N2 0.059(3) 0.044(2) 0.036(2) 0.0030(17) 0.005(2) -0.006(2) N3 0.051(3) 0.045(2) 0.034(2) -0.0065(17) 0.0092(19) -0.006(2) O1 0.064(2) 0.064(2) 0.051(2) 0.0066(17) 0.0279(19) 0.008(2) O2 0.057(2) 0.0400(17) 0.0310(16) 0.0050(13) 0.0056(15) 0.0073(16) Cl1 0.1004(12) 0.0586(8) 0.0625(8) 0.0115(7) 0.0146(8) 0.0055(8) Cl2 0.0696(10) 0.0666(8) 0.0597(8) 0.0074(7) 0.0009(7) 0.0076(8) Cl3 0.0714(10) 0.0735(9) 0.0466(7) 0.0044(6) 0.0032(6) -0.0019(8) _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 C6 1.407(6) . ? C1 C2 1.411(6) . ? C1 C29 1.498(6) . ? C2 C3 1.421(6) . ? C2 C7 1.458(7) . ? C3 N1 1.354(6) . ? C3 C4 1.425(6) . ? C4 C5 1.417(6) . ? C4 C8 1.446(7) . ? C5 C6 1.432(6) . ? C5 C9 1.483(6) . ? C6 C19 1.509(6) . ? C7 N3 1.149(6) . ? C8 N2 1.147(5) . ? C9 C10 1.408(6) . ? C9 C14 1.428(5) . ? C10 C11 1.388(6) . ? C10 H10A 0.9500 . ? C11 C12 1.410(5) . ? C11 H11A 0.9500 . ? C12 C13 1.418(6) . ? C12 C15 1.541(6) . ? C13 C14 1.360(6) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 C18 1.528(6) . ? C15 C17 1.540(7) . ? C15 C16 1.545(6) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18C 0.9800 . ? C18 H18B 0.9800 . ? C18 H18A 0.9800 . ? C19 C24 1.385(6) . ? C19 C20 1.398(6) . ? C20 C21 1.396(6) . ? C20 H20A 0.9500 . ? C21 C22 1.399(6) . ? C21 H21A 0.9500 . ? C22 C23 1.409(6) . ? C22 C25 1.556(6) . ? C23 C24 1.382(6) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C25 C28 1.522(7) . ? C25 C26 1.529(7) . ? C25 C27 1.549(6) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 O1 1.214(5) . ? C29 O2 1.327(5) . ? C30 O2 1.465(5) . ? C30 C31 1.516(7) . ? C30 H30B 0.9900 . ? C30 H30A 0.9900 . ? C31 H31C 0.9800 . ? C31 H31B 0.9800 . ? C31 H31A 0.9800 . ? C32 Cl2 1.757(6) . ? C32 Cl1 1.764(5) . ? C32 Cl3 1.782(5) . ? C32 H32A 1.0000 . ? N1 H1 0.77(5) . ? N1 H2 0.78(5) . ? 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 C6 C1 C2 121.8(4) . . ? C6 C1 C29 120.1(4) . . ? C2 C1 C29 118.0(4) . . ? C1 C2 C3 121.1(4) . . ? C1 C2 C7 119.6(4) . . ? C3 C2 C7 119.3(4) . . ? N1 C3 C2 121.1(4) . . ? N1 C3 C4 122.5(4) . . ? C2 C3 C4 116.4(4) . . ? C5 C4 C3 123.0(4) . . ? C5 C4 C8 120.2(4) . . ? C3 C4 C8 116.6(4) . . ? C4 C5 C6 119.0(4) . . ? C4 C5 C9 120.6(4) . . ? C6 C5 C9 120.4(3) . . ? C1 C6 C5 118.3(4) . . ? C1 C6 C19 120.2(4) . . ? C5 C6 C19 121.5(4) . . ? N3 C7 C2 177.3(5) . . ? N2 C8 C4 174.7(4) . . ? C10 C9 C14 116.7(4) . . ? C10 C9 C5 122.3(3) . . ? C14 C9 C5 121.0(4) . . ? C11 C10 C9 121.3(4) . . ? C11 C10 H10A 119.4 . . ? C9 C10 H10A 119.4 . . ? C10 C11 C12 122.1(4) . . ? C10 C11 H11A 119.0 . . ? C12 C11 H11A 119.0 . . ? C11 C12 C13 116.0(4) . . ? C11 C12 C15 123.6(4) . . ? C13 C12 C15 120.4(3) . . ? C14 C13 C12 122.6(3) . . ? C14 C13 H13A 118.7 . . ? C12 C13 H13A 118.7 . . ? C13 C14 C9 121.4(4) . . ? C13 C14 H14A 119.3 . . ? C9 C14 H14A 119.3 . . ? C18 C15 C17 109.5(4) . . ? C18 C15 C12 109.6(4) . . ? C17 C15 C12 109.2(4) . . ? C18 C15 C16 107.6(4) . . ? C17 C15 C16 109.1(4) . . ? C12 C15 C16 111.8(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18C 109.5 . . ? C15 C18 H18B 109.5 . . ? H18C C18 H18B 109.5 . . ? C15 C18 H18A 109.5 . . ? H18C C18 H18A 109.5 . . ? H18B C18 H18A 109.5 . . ? C24 C19 C20 118.6(4) . . ? C24 C19 C6 121.6(4) . . ? C20 C19 C6 119.8(4) . . ? C21 C20 C19 120.8(4) . . ? C21 C20 H20A 119.6 . . ? C19 C20 H20A 119.6 . . ? C20 C21 C22 120.9(4) . . ? C20 C21 H21A 119.5 . . ? C22 C21 H21A 119.5 . . ? C21 C22 C23 117.2(4) . . ? C21 C22 C25 124.1(4) . . ? C23 C22 C25 118.7(4) . . ? C24 C23 C22 121.7(4) . . ? C24 C23 H23A 119.2 . . ? C22 C23 H23A 119.2 . . ? C23 C24 C19 120.7(4) . . ? C23 C24 H24A 119.6 . . ? C19 C24 H24A 119.6 . . ? C28 C25 C26 110.4(4) . . ? C28 C25 C27 108.8(4) . . ? C26 C25 C27 108.5(4) . . ? C28 C25 C22 108.6(4) . . ? C26 C25 C22 109.4(4) . . ? C27 C25 C22 110.9(4) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O1 C29 O2 124.9(5) . . ? O1 C29 C1 125.0(5) . . ? O2 C29 C1 110.1(4) . . ? O2 C30 C31 110.1(4) . . ? O2 C30 H30B 109.6 . . ? C31 C30 H30B 109.6 . . ? O2 C30 H30A 109.6 . . ? C31 C30 H30A 109.6 . . ? H30B C30 H30A 108.2 . . ? C30 C31 H31C 109.5 . . ? C30 C31 H31B 109.5 . . ? H31C C31 H31B 109.5 . . ? C30 C31 H31A 109.5 . . ? H31C C31 H31A 109.5 . . ? H31B C31 H31A 109.5 . . ? Cl2 C32 Cl1 110.8(3) . . ? Cl2 C32 Cl3 110.8(3) . . ? Cl1 C32 Cl3 109.7(3) . . ? Cl2 C32 H32A 108.5 . . ? Cl1 C32 H32A 108.5 . . ? Cl3 C32 H32A 108.5 . . ? C3 N1 H1 125(4) . . ? C3 N1 H2 119(4) . . ? H1 N1 H2 105(6) . . ? C29 O2 C30 116.9(4) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.332 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.082 #============================================================================= data_D1 _database_code_depnum_ccdc_archive 'CCDC 663313' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 Cl N2 O2' _chemical_formula_sum 'C14 H11 Cl N2 O2' _chemical_formula_weight 274.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 8.1061(13) _cell_length_b 11.0894(18) _cell_length_c 15.395(3) _cell_angle_alpha 90.00 _cell_angle_beta 86.357(2) _cell_angle_gamma 90.00 _cell_volume 1381.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5143 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 22.5 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7737 _diffrn_reflns_av_R_equivalents 0.1988 _diffrn_reflns_av_sigmaI/netI 0.1192 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2356 _reflns_number_gt 2035 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART ' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SHELXS (Bruker, 2000)' _computing_structure_refinement 'SHELXL (Bruker, 2000)' _computing_molecular_graphics 'SHELXP (Bruker, 2000)' _computing_publication_material 'SHELXTL (Bruker, 2000)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0309P)^2^+0.1996P] 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 SHELXL _refine_ls_extinction_coef 0.029(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2356 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1306 _refine_ls_wR_factor_gt 0.1206 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _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 C1 C -0.0605(2) 0.52193(15) 0.13574(11) 0.0461(4) Uani 1 1 d . . . C2 C 0.0831(2) 0.48247(16) 0.16952(12) 0.0524(5) Uani 1 1 d . . . H2A H 0.1395 0.5313 0.2068 0.063 Uiso 1 1 calc R . . C3 C 0.1423(2) 0.36841(17) 0.14693(12) 0.0517(5) Uani 1 1 d . . . H3A H 0.2394 0.3410 0.1693 0.062 Uiso 1 1 calc R . . C4 C 0.05916(19) 0.29497(15) 0.09180(11) 0.0407(4) Uani 1 1 d . . . C5 C -0.0874(2) 0.33738(15) 0.05958(11) 0.0453(4) Uani 1 1 d . . . H5A H -0.1455 0.2886 0.0230 0.054 Uiso 1 1 calc R . . C6 C -0.1471(2) 0.45091(15) 0.08147(11) 0.0477(4) Uani 1 1 d . . . H6A H -0.2446 0.4788 0.0598 0.057 Uiso 1 1 calc R . . C7 C 0.11381(19) 0.17095(14) 0.06627(10) 0.0413(4) Uani 1 1 d . . . H7A H 0.0240 0.1199 0.0476 0.050 Uiso 1 1 calc R . . C8 C 0.2451(2) 0.10208(15) 0.10853(11) 0.0446(4) Uani 1 1 d . . . H8A H 0.3014 0.1445 0.1540 0.054 Uiso 1 1 calc R . . C9 C 0.2818(2) 0.14746(15) 0.01468(11) 0.0454(4) Uani 1 1 d . . . C10 C 0.3997(2) 0.24528(19) 0.00377(13) 0.0558(5) Uani 1 1 d . . . C11 C 0.2848(2) 0.06394(18) -0.05736(14) 0.0582(5) Uani 1 1 d . . . C12 C 0.2199(2) -0.03054(16) 0.12132(11) 0.0458(4) Uani 1 1 d . . . C13 C 0.2869(2) -0.19877(17) 0.20576(13) 0.0561(5) Uani 1 1 d . . . H13A H 0.2892 -0.2462 0.1527 0.067 Uiso 1 1 calc R . . H13B H 0.1826 -0.2131 0.2385 0.067 Uiso 1 1 calc R . . C14 C 0.4267(3) -0.2330(2) 0.25829(17) 0.0760(7) Uani 1 1 d . . . H14A H 0.4183 -0.3170 0.2731 0.114 Uiso 1 1 calc R . . H14B H 0.4230 -0.1857 0.3106 0.114 Uiso 1 1 calc R . . H14C H 0.5292 -0.2186 0.2252 0.114 Uiso 1 1 calc R . . Cl1 Cl -0.13235(7) 0.66621(4) 0.16305(3) 0.0634(2) Uani 1 1 d . . . N1 N 0.4941(2) 0.32104(19) -0.00451(15) 0.0791(6) Uani 1 1 d . . . N2 N 0.2904(3) 0.0003(2) -0.11565(14) 0.0921(7) Uani 1 1 d . . . O1 O 0.1323(2) -0.09003(12) 0.07851(10) 0.0740(5) Uani 1 1 d . . . O2 O 0.30517(15) -0.07064(11) 0.18496(8) 0.0522(4) 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 C1 0.0521(9) 0.0378(8) 0.0474(9) 0.0022(7) 0.0046(7) 0.0015(7) C2 0.0601(10) 0.0430(9) 0.0554(11) -0.0063(9) -0.0144(8) -0.0038(8) C3 0.0509(9) 0.0452(9) 0.0608(11) -0.0039(9) -0.0173(8) 0.0016(8) C4 0.0411(8) 0.0382(8) 0.0428(9) 0.0012(7) -0.0025(6) -0.0023(7) C5 0.0431(9) 0.0461(9) 0.0472(10) -0.0022(8) -0.0071(7) -0.0032(7) C6 0.0438(8) 0.0477(9) 0.0518(10) 0.0018(8) -0.0044(7) 0.0050(8) C7 0.0396(8) 0.0403(9) 0.0445(9) -0.0018(7) -0.0060(6) -0.0023(7) C8 0.0466(8) 0.0405(9) 0.0478(10) -0.0009(8) -0.0101(7) 0.0002(7) C9 0.0450(8) 0.0418(8) 0.0496(10) -0.0016(8) -0.0035(7) 0.0002(7) C10 0.0501(9) 0.0552(11) 0.0617(11) 0.0027(9) -0.0002(8) -0.0005(9) C11 0.0618(11) 0.0540(11) 0.0578(12) -0.0042(10) 0.0042(8) 0.0037(9) C12 0.0466(9) 0.0429(9) 0.0488(10) -0.0006(8) -0.0088(7) 0.0010(7) C13 0.0585(10) 0.0472(9) 0.0628(12) 0.0115(9) -0.0056(8) 0.0023(9) C14 0.0627(11) 0.0791(15) 0.0868(15) 0.0310(13) -0.0108(10) 0.0088(11) Cl1 0.0749(4) 0.0442(3) 0.0706(4) -0.0083(2) 0.0002(2) 0.0111(2) N1 0.0666(11) 0.0757(12) 0.0940(14) 0.0083(11) 0.0013(9) -0.0210(10) N2 0.1137(17) 0.0830(15) 0.0772(14) -0.0305(13) 0.0116(12) 0.0019(14) O1 0.0976(11) 0.0444(7) 0.0855(11) 0.0054(7) -0.0475(8) -0.0125(8) O2 0.0553(7) 0.0459(7) 0.0570(7) 0.0058(6) -0.0158(5) 0.0008(6) _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 C6 1.373(3) . ? C1 C2 1.376(3) . ? C1 Cl1 1.7450(17) . ? C2 C3 1.389(3) . ? C2 H2A 0.9300 . ? C3 C4 1.382(2) . ? C3 H3A 0.9300 . ? C4 C5 1.398(2) . ? C4 C7 1.490(2) . ? C5 C6 1.383(2) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.493(2) . ? C7 C9 1.554(2) . ? C7 H7A 0.9800 . ? C8 C12 1.496(2) . ? C8 C9 1.541(2) . ? C8 H8A 0.9800 . ? C9 C11 1.444(3) . ? C9 C10 1.448(3) . ? C10 N1 1.138(3) . ? C11 N2 1.140(3) . ? C12 O1 1.197(2) . ? C12 O2 1.312(2) . ? C13 O2 1.462(2) . ? C13 C14 1.482(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.67(16) . . ? C6 C1 Cl1 119.78(14) . . ? C2 C1 Cl1 118.55(14) . . ? C1 C2 C3 118.80(17) . . ? C1 C2 H2A 120.6 . . ? C3 C2 H2A 120.6 . . ? C4 C3 C2 121.09(17) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C3 C4 C5 118.56(16) . . ? C3 C4 C7 123.88(15) . . ? C5 C4 C7 117.53(15) . . ? C6 C5 C4 120.81(17) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C1 C6 C5 119.06(16) . . ? C1 C6 H6A 120.5 . . ? C5 C6 H6A 120.5 . . ? C4 C7 C8 124.45(15) . . ? C4 C7 C9 121.72(13) . . ? C8 C7 C9 60.73(11) . . ? C4 C7 H7A 113.4 . . ? C8 C7 H7A 113.4 . . ? C9 C7 H7A 113.4 . . ? C7 C8 C12 117.72(15) . . ? C7 C8 C9 61.61(11) . . ? C12 C8 C9 117.45(14) . . ? C7 C8 H8A 116.3 . . ? C12 C8 H8A 116.3 . . ? C9 C8 H8A 116.3 . . ? C11 C9 C10 114.36(15) . . ? C11 C9 C8 120.24(15) . . ? C10 C9 C8 116.08(15) . . ? C11 C9 C7 118.15(15) . . ? C10 C9 C7 118.94(15) . . ? C8 C9 C7 57.66(10) . . ? N1 C10 C9 179.0(2) . . ? N2 C11 C9 177.9(2) . . ? O1 C12 O2 125.68(17) . . ? O1 C12 C8 123.37(16) . . ? O2 C12 C8 110.95(15) . . ? O2 C13 C14 107.38(18) . . ? O2 C13 H13A 110.2 . . ? C14 C13 H13A 110.2 . . ? O2 C13 H13B 110.2 . . ? C14 C13 H13B 110.2 . . ? H13A C13 H13B 108.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 O2 C13 116.26(15) . . ? 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 C6 C1 C2 C3 0.9(3) . . . . ? Cl1 C1 C2 C3 -179.01(14) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C2 C3 C4 C7 -178.77(16) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C7 C4 C5 C6 179.07(15) . . . . ? C2 C1 C6 C5 -0.7(3) . . . . ? Cl1 C1 C6 C5 179.18(13) . . . . ? C4 C5 C6 C1 -0.1(3) . . . . ? C3 C4 C7 C8 11.6(3) . . . . ? C5 C4 C7 C8 -166.57(15) . . . . ? C3 C4 C7 C9 -62.5(2) . . . . ? C5 C4 C7 C9 119.27(17) . . . . ? C4 C7 C8 C12 141.80(16) . . . . ? C9 C7 C8 C12 -107.94(16) . . . . ? C4 C7 C8 C9 -110.26(17) . . . . ? C7 C8 C9 C11 -106.10(18) . . . . ? C12 C8 C9 C11 2.3(2) . . . . ? C7 C8 C9 C10 109.13(17) . . . . ? C12 C8 C9 C10 -142.51(16) . . . . ? C12 C8 C9 C7 108.37(17) . . . . ? C4 C7 C9 C11 -135.71(17) . . . . ? C8 C7 C9 C11 109.71(18) . . . . ? C4 C7 C9 C10 10.4(2) . . . . ? C8 C7 C9 C10 -104.16(18) . . . . ? C4 C7 C9 C8 114.58(18) . . . . ? C11 C9 C10 N1 -77(13) . . . . ? C8 C9 C10 N1 70(13) . . . . ? C7 C9 C10 N1 136(13) . . . . ? C10 C9 C11 N2 -8(7) . . . . ? C8 C9 C11 N2 -154(7) . . . . ? C7 C9 C11 N2 139(7) . . . . ? C7 C8 C12 O1 23.4(3) . . . . ? C9 C8 C12 O1 -47.1(2) . . . . ? C7 C8 C12 O2 -156.25(15) . . . . ? C9 C8 C12 O2 133.15(15) . . . . ? O1 C12 O2 C13 -1.5(3) . . . . ? C8 C12 O2 C13 178.18(14) . . . . ? C14 C13 O2 C12 163.14(16) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.206 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.045 #============================================================================= data_i0373 #no. D2 in publication _database_code_depnum_ccdc_archive 'CCDC 663314' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 Br N2 O2' _chemical_formula_sum 'C14 H11 Br N2 O2' _chemical_formula_weight 319.16 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' Br Br -0.2901 2.4595 '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/n' _symmetry_space_group_name_Hall '-P 2yn' 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 7.0199(7) _cell_length_b 8.0123(5) _cell_length_c 24.381(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.198(8) _cell_angle_gamma 90.00 _cell_volume 1365.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 7781 _cell_measurement_theta_min 1.68 _cell_measurement_theta_max 25.55 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 3.009 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.2908 _exptl_absorpt_correction_T_max 0.4988 _exptl_absorpt_process_details 'X-red ver 1.06 (Stoe & Cie. 2001)' _exptl_special_details ; ? ; _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_voltage 50 _diffrn_source_current 32 _diffrn_source_power 1.60 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_ambient_temperature 133(2) _diffrn_measurement_method 'rotation method' _diffrn_measurement_details ; 180 frames, detector distance = 135 mm ; _diffrn_standards_decay_% none _diffrn_reflns_number 8536 _diffrn_reflns_av_R_equivalents 0.1118 _diffrn_reflns_av_sigmaI/netI 0.0819 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2385 _reflns_number_gt 1887 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0600P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2385 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1085 _refine_ls_wR_factor_gt 0.1061 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _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 C1 C -0.0167(5) 0.7306(5) 0.42878(16) 0.0285(8) Uani 1 1 d . . . C2 C -0.0826(5) 0.7563(6) 0.48054(16) 0.0346(9) Uani 1 1 d . . . H2 H -0.0103 0.7184 0.5130 0.042 Uiso 1 1 calc R . . C3 C -0.2549(5) 0.8380(6) 0.48367(17) 0.0379(10) Uani 1 1 d . . . H3 H -0.3022 0.8556 0.5185 0.045 Uiso 1 1 calc R . . C4 C -0.3584(5) 0.8940(5) 0.43638(17) 0.0342(9) Uani 1 1 d . . . H4 H -0.4767 0.9500 0.4388 0.041 Uiso 1 1 calc R . . C5 C -0.2904(5) 0.8690(5) 0.38536(16) 0.0284(8) Uani 1 1 d . . . H5 H -0.3621 0.9087 0.3531 0.034 Uiso 1 1 calc R . . C6 C -0.1178(5) 0.7859(5) 0.38105(14) 0.0239(8) Uani 1 1 d . . . C7 C -0.0449(5) 0.7550(5) 0.32580(14) 0.0238(8) Uani 1 1 d . . . H7 H -0.0351 0.6349 0.3153 0.029 Uiso 1 1 calc R . . C8 C -0.0873(5) 0.8732(5) 0.27855(15) 0.0249(8) Uani 1 1 d . . . H8 H -0.1666 0.9731 0.2858 0.030 Uiso 1 1 calc R . . C9 C -0.1197(5) 0.7974(5) 0.22227(15) 0.0250(8) Uani 1 1 d . . . C10 C 0.1176(4) 0.8692(5) 0.30789(15) 0.0235(8) Uani 1 1 d . . . C11 C 0.1727(5) 1.0077(5) 0.34340(16) 0.0274(8) Uani 1 1 d . . . C12 C 0.2753(5) 0.7903(5) 0.28173(15) 0.0301(9) Uani 1 1 d . . . C13 C -0.2764(5) 0.8310(5) 0.13290(15) 0.0295(9) Uani 1 1 d . . . H13A H -0.4026 0.8749 0.1181 0.035 Uiso 1 1 calc R . . H13B H -0.2851 0.7077 0.1341 0.035 Uiso 1 1 calc R . . C14 C -0.1253(5) 0.8821(6) 0.09521(17) 0.0346(9) Uani 1 1 d . . . H14C H -0.1579 0.8355 0.0584 0.041 Uiso 1 1 calc R . . H14B H -0.0003 0.8395 0.1101 0.041 Uiso 1 1 calc R . . H14A H -0.1204 1.0041 0.0929 0.041 Uiso 1 1 calc R . . N1 N 0.2111(5) 1.1127(5) 0.37391(14) 0.0343(8) Uani 1 1 d . . . N2 N 0.4031(4) 0.7314(5) 0.26339(15) 0.0408(9) Uani 1 1 d . . . O1 O -0.0567(3) 0.6618(3) 0.21087(10) 0.0298(6) Uani 1 1 d . . . O2 O -0.2289(3) 0.8952(3) 0.18837(10) 0.0282(6) Uani 1 1 d . . . Br Br 0.21987(5) 0.61603(6) 0.425220(16) 0.03630(19) 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 C1 0.0237(16) 0.032(2) 0.030(2) 0.0034(17) 0.0057(14) -0.0013(15) C2 0.0343(19) 0.044(3) 0.025(2) 0.0032(18) 0.0007(15) -0.0023(17) C3 0.039(2) 0.049(3) 0.027(2) -0.0019(19) 0.0137(17) 0.0001(18) C4 0.0296(18) 0.040(3) 0.034(2) -0.0034(19) 0.0078(16) 0.0029(17) C5 0.0258(17) 0.034(2) 0.026(2) 0.0033(17) 0.0033(14) -0.0035(15) C6 0.0240(16) 0.027(2) 0.0209(18) -0.0019(15) 0.0043(13) -0.0045(14) C7 0.0239(16) 0.027(2) 0.0213(18) 0.0011(15) 0.0049(13) -0.0039(14) C8 0.0244(16) 0.029(2) 0.0221(18) -0.0018(15) 0.0040(13) -0.0012(14) C9 0.0224(16) 0.026(2) 0.0271(19) -0.0002(16) 0.0048(14) -0.0031(14) C10 0.0231(16) 0.028(2) 0.0207(18) -0.0022(15) 0.0056(13) -0.0007(14) C11 0.0232(16) 0.034(2) 0.026(2) 0.0071(18) 0.0077(14) 0.0000(15) C12 0.0278(18) 0.035(2) 0.028(2) -0.0011(17) 0.0053(15) -0.0004(16) C13 0.0283(18) 0.035(2) 0.025(2) -0.0014(17) 0.0007(14) -0.0033(15) C14 0.0340(19) 0.043(3) 0.028(2) 0.0006(18) 0.0081(16) 0.0034(17) N1 0.0370(17) 0.037(2) 0.0289(19) -0.0044(16) 0.0055(14) -0.0055(15) N2 0.0335(17) 0.051(3) 0.038(2) -0.0104(18) 0.0073(15) 0.0031(16) O1 0.0344(13) 0.0275(17) 0.0277(15) -0.0027(11) 0.0032(11) 0.0026(11) O2 0.0297(12) 0.0299(16) 0.0249(14) -0.0004(11) 0.0024(10) 0.0026(10) Br 0.0268(2) 0.0473(3) 0.0350(3) 0.00986(19) 0.00373(15) 0.00670(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 C6 1.380(5) . ? C1 C2 1.398(5) . ? C1 Br 1.907(3) . ? C2 C3 1.383(5) . ? C2 H2 0.9500 . ? C3 C4 1.381(6) . ? C3 H3 0.9500 . ? C4 C5 1.387(5) . ? C4 H4 0.9500 . ? C5 C6 1.395(5) . ? C5 H5 0.9500 . ? C6 C7 1.504(5) . ? C7 C8 1.500(5) . ? C7 C10 1.555(4) . ? C7 H7 1.0000 . ? C8 C9 1.499(5) . ? C8 C10 1.547(5) . ? C8 H8 1.0000 . ? C9 O1 1.215(5) . ? C9 O2 1.331(5) . ? C10 C11 1.439(5) . ? C10 C12 1.470(5) . ? C11 N1 1.139(5) . ? C12 N2 1.140(5) . ? C13 O2 1.457(5) . ? C13 C14 1.521(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14C 0.9800 . ? C14 H14B 0.9800 . ? C14 H14A 0.9800 . ? 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 C6 C1 C2 121.8(3) . . ? C6 C1 Br 120.0(3) . . ? C2 C1 Br 118.2(3) . . ? C3 C2 C1 118.8(4) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.3(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 118.3(3) . . ? C1 C6 C7 120.8(3) . . ? C5 C6 C7 120.9(3) . . ? C8 C7 C6 121.6(3) . . ? C8 C7 C10 60.8(2) . . ? C6 C7 C10 118.2(3) . . ? C8 C7 H7 115.1 . . ? C6 C7 H7 115.1 . . ? C10 C7 H7 115.1 . . ? C9 C8 C7 116.7(3) . . ? C9 C8 C10 118.2(3) . . ? C7 C8 C10 61.4(2) . . ? C9 C8 H8 116.4 . . ? C7 C8 H8 116.4 . . ? C10 C8 H8 116.4 . . ? O1 C9 O2 125.9(3) . . ? O1 C9 C8 122.9(3) . . ? O2 C9 C8 111.2(3) . . ? C11 C10 C12 114.9(3) . . ? C11 C10 C8 116.7(3) . . ? C12 C10 C8 120.9(3) . . ? C11 C10 C7 116.7(3) . . ? C12 C10 C7 118.0(3) . . ? C8 C10 C7 57.8(2) . . ? N1 C11 C10 175.9(4) . . ? N2 C12 C10 176.9(4) . . ? O2 C13 C14 110.6(3) . . ? O2 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C13 C14 H14C 109.5 . . ? C13 C14 H14B 109.5 . . ? H14C C14 H14B 109.5 . . ? C13 C14 H14A 109.5 . . ? H14C C14 H14A 109.5 . . ? H14B C14 H14A 109.5 . . ? C9 O2 C13 116.0(3) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.797 _refine_diff_density_min -1.115 _refine_diff_density_rms 0.111 #============================================================================= data_i0370 # no. F in publication _database_code_depnum_ccdc_archive 'CCDC 663315' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H38 Cl4 N4 O2' _chemical_formula_sum 'C34 H38 Cl4 N4 O2' _chemical_formula_weight 676.48 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' Cl Cl 0.1484 0.1585 '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 'P 21/c' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' 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 11.9375(9) _cell_length_b 11.4575(9) _cell_length_c 26.5022(19) _cell_angle_alpha 90.00 _cell_angle_beta 92.363(6) _cell_angle_gamma 90.00 _cell_volume 3621.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 11166 _cell_measurement_theta_min 1.54 _cell_measurement_theta_max 25.67 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 0.361 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8516 _exptl_absorpt_correction_T_max 0.9371 _exptl_absorpt_process_details 'X-red ver. 1.06 (Stoe & Cie., 2001)' _exptl_special_details ; ? ; _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_voltage 50 _diffrn_source_current 32 _diffrn_source_power 1.60 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_ambient_temperature 133(2) _diffrn_measurement_method 'rotation method' _diffrn_measurement_details ; 180 frames, detector distance = 130 mm ; _diffrn_standards_decay_% none _diffrn_reflns_number 23044 _diffrn_reflns_av_R_equivalents 0.0738 _diffrn_reflns_av_sigmaI/netI 0.0848 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 24.99 _reflns_number_total 6375 _reflns_number_gt 3550 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1654P)^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 6375 _refine_ls_number_parameters 411 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1209 _refine_ls_R_factor_gt 0.0814 _refine_ls_wR_factor_ref 0.2466 _refine_ls_wR_factor_gt 0.2266 _refine_ls_goodness_of_fit_ref 0.929 _refine_ls_restrained_S_all 0.929 _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 C1 C 0.5800(3) 0.3085(3) 0.68079(15) 0.0258(8) Uani 1 1 d . . . C2 C 0.6014(3) 0.3293(3) 0.62458(15) 0.0269(9) Uani 1 1 d . . . C3 C 0.7098(3) 0.2620(3) 0.60807(15) 0.0252(8) Uani 1 1 d . . . H3 H 0.7093 0.2637 0.5703 0.030 Uiso 1 1 calc R . . C4 C 0.6999(3) 0.1346(3) 0.62384(14) 0.0260(8) Uani 1 1 d . . . C5 C 0.6464(3) 0.1062(3) 0.66621(15) 0.0268(9) Uani 1 1 d . . . C6 C 0.5965(3) 0.1972(3) 0.69800(15) 0.0279(9) Uani 1 1 d . . . C7 C 0.6115(3) 0.4554(4) 0.61332(15) 0.0296(9) Uani 1 1 d . . . C8 C 0.5037(4) 0.2819(4) 0.59477(16) 0.0333(10) Uani 1 1 d . . . C9 C 0.5715(3) 0.1707(3) 0.74902(16) 0.0292(9) Uani 1 1 d . . . C10 C 0.6278(3) -0.0181(3) 0.68077(14) 0.0276(9) Uani 1 1 d . . . C11 C 0.7018(4) -0.2103(3) 0.68262(18) 0.0386(11) Uani 1 1 d . . . H11A H 0.6426 -0.2382 0.6583 0.046 Uiso 1 1 calc R . . H11B H 0.6797 -0.2299 0.7172 0.046 Uiso 1 1 calc R . . C12 C 0.8130(4) -0.2655(4) 0.6718(2) 0.0500(13) Uani 1 1 d . . . H12C H 0.8706 -0.2366 0.6961 0.060 Uiso 1 1 calc R . . H12B H 0.8336 -0.2452 0.6375 0.060 Uiso 1 1 calc R . . H12A H 0.8070 -0.3505 0.6749 0.060 Uiso 1 1 calc R . . C13 C 0.8170(3) 0.3225(3) 0.62720(15) 0.0252(8) Uani 1 1 d . . . C14 C 0.8707(3) 0.2973(4) 0.67320(16) 0.0350(10) Uani 1 1 d . . . H14 H 0.8408 0.2393 0.6944 0.042 Uiso 1 1 calc R . . C15 C 0.9680(4) 0.3559(4) 0.68858(17) 0.0380(10) Uani 1 1 d . . . H15 H 1.0023 0.3381 0.7206 0.046 Uiso 1 1 calc R . . C16 C 1.0173(3) 0.4405(3) 0.65838(16) 0.0319(9) Uani 1 1 d . . . C17 C 0.9619(3) 0.4648(3) 0.61229(15) 0.0295(9) Uani 1 1 d . . . H17 H 0.9917 0.5226 0.5910 0.035 Uiso 1 1 calc R . . C18 C 0.8647(3) 0.4072(3) 0.59664(15) 0.0269(8) Uani 1 1 d . . . H18 H 0.8299 0.4254 0.5647 0.032 Uiso 1 1 calc R . . C19 C 1.1268(3) 0.5012(4) 0.67614(17) 0.0383(10) Uani 1 1 d . . . C20 C 1.1112(4) 0.5630(5) 0.7264(2) 0.0520(13) Uani 1 1 d . . . H20A H 1.0866 0.5064 0.7513 0.062 Uiso 1 1 calc R . . H20B H 1.0545 0.6244 0.7218 0.062 Uiso 1 1 calc R . . H20C H 1.1825 0.5979 0.7382 0.062 Uiso 1 1 calc R . . C21 C 1.1644(5) 0.5925(6) 0.6374(2) 0.0707(18) Uani 1 1 d . . . H21A H 1.1081 0.6546 0.6341 0.085 Uiso 1 1 calc R . . H21B H 1.1725 0.5548 0.6046 0.085 Uiso 1 1 calc R . . H21C H 1.2365 0.6261 0.6490 0.085 Uiso 1 1 calc R . . C22 C 1.2191(4) 0.4073(5) 0.6835(2) 0.0586(15) Uani 1 1 d . . . H22C H 1.2895 0.4446 0.6950 0.070 Uiso 1 1 calc R . . H22B H 1.2297 0.3673 0.6514 0.070 Uiso 1 1 calc R . . H22A H 1.1965 0.3506 0.7088 0.070 Uiso 1 1 calc R . . C23 C 0.7485(3) 0.0459(3) 0.58990(15) 0.0280(9) Uani 1 1 d . . . C24 C 0.8638(3) 0.0313(4) 0.58792(19) 0.0415(11) Uani 1 1 d . . . H24 H 0.9129 0.0813 0.6070 0.050 Uiso 1 1 calc R . . C25 C 0.9079(4) -0.0566(4) 0.55794(18) 0.0414(11) Uani 1 1 d . . . H25 H 0.9869 -0.0652 0.5573 0.050 Uiso 1 1 calc R . . C26 C 0.8404(3) -0.1312(3) 0.52929(15) 0.0290(9) Uani 1 1 d . . . C27 C 0.7242(4) -0.1122(4) 0.53013(17) 0.0389(10) Uani 1 1 d . . . H27 H 0.6751 -0.1597 0.5099 0.047 Uiso 1 1 calc R . . C28 C 0.6797(3) -0.0259(4) 0.55980(17) 0.0374(10) Uani 1 1 d . . . H28 H 0.6007 -0.0155 0.5596 0.045 Uiso 1 1 calc R . . C29 C 0.8877(4) -0.2298(3) 0.49661(16) 0.0339(10) Uani 1 1 d . . . C30 C 0.8723(4) -0.1959(4) 0.44082(16) 0.0351(10) Uani 1 1 d . . . H30A H 0.9076 -0.1200 0.4353 0.042 Uiso 1 1 calc R . . H30B H 0.7921 -0.1909 0.4316 0.042 Uiso 1 1 calc R . . H30C H 0.9072 -0.2551 0.4199 0.042 Uiso 1 1 calc R . . C31 C 1.0130(4) -0.2499(4) 0.50968(19) 0.0448(12) Uani 1 1 d . . . H31A H 1.0236 -0.2659 0.5459 0.054 Uiso 1 1 calc R . . H31B H 1.0555 -0.1799 0.5011 0.054 Uiso 1 1 calc R . . H31C H 1.0397 -0.3165 0.4904 0.054 Uiso 1 1 calc R . . C32 C 0.8238(4) -0.3446(4) 0.50624(18) 0.0430(11) Uani 1 1 d . . . H32A H 0.7454 -0.3360 0.4944 0.052 Uiso 1 1 calc R . . H32B H 0.8271 -0.3618 0.5425 0.052 Uiso 1 1 calc R . . H32C H 0.8585 -0.4086 0.4880 0.052 Uiso 1 1 calc R . . C33 C 0.7443(9) 0.0372(19) 0.3278(6) 0.300(13) Uani 1 1 d . . . H33A H 0.7030 0.0997 0.3091 0.360 Uiso 1 1 calc R . . H33B H 0.7092 0.0275 0.3607 0.360 Uiso 1 1 calc R . . C34 C 0.5795(5) 0.2849(5) 0.4372(2) 0.0668(16) Uani 1 1 d . . . H34A H 0.4976 0.2763 0.4407 0.080 Uiso 1 1 calc R . . H34B H 0.5930 0.2994 0.4012 0.080 Uiso 1 1 calc R . . Cl1 Cl 0.7284(3) -0.0920(3) 0.29394(19) 0.221(2) Uani 1 1 d . . . Cl2 Cl 0.8739(4) 0.0798(3) 0.33814(16) 0.2053(18) Uani 1 1 d . . . Cl3 Cl 0.64657(19) 0.15640(17) 0.45640(9) 0.1065(7) Uani 1 1 d . . . Cl4 Cl 0.62844(14) 0.40511(14) 0.47358(6) 0.0740(5) Uani 1 1 d . . . N1 N 0.5424(3) 0.3989(3) 0.70724(14) 0.0337(8) Uani 1 1 d D . . H1A H 0.527(4) 0.466(3) 0.6919(16) 0.043(9) Uiso 1 1 d D . . H1B H 0.536(4) 0.397(4) 0.7409(8) 0.043(9) Uiso 1 1 d D . . N2 N 0.6176(3) 0.5533(3) 0.60522(15) 0.0406(9) Uani 1 1 d . . . N3 N 0.4311(3) 0.2420(4) 0.57134(17) 0.0534(11) Uani 1 1 d . . . N4 N 0.5515(3) 0.1499(3) 0.79045(14) 0.0358(8) Uani 1 1 d . . . O1 O 0.5367(2) -0.0534(2) 0.69387(11) 0.0369(7) Uani 1 1 d . . . O2 O 0.7179(2) -0.0840(2) 0.67748(10) 0.0311(7) 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 C1 0.0209(18) 0.0280(19) 0.029(2) -0.0034(16) 0.0037(16) -0.0013(15) C2 0.0249(19) 0.0280(19) 0.028(2) -0.0022(16) 0.0032(17) -0.0004(16) C3 0.025(2) 0.0257(18) 0.025(2) -0.0013(15) 0.0063(16) 0.0002(15) C4 0.0251(19) 0.0266(19) 0.026(2) -0.0023(16) 0.0014(17) -0.0001(15) C5 0.0232(19) 0.0262(19) 0.031(2) -0.0005(16) 0.0045(17) -0.0004(15) C6 0.027(2) 0.029(2) 0.028(2) -0.0013(16) 0.0075(17) 0.0005(16) C7 0.026(2) 0.033(2) 0.030(2) -0.0006(18) 0.0036(17) 0.0046(17) C8 0.028(2) 0.040(2) 0.033(2) -0.0038(19) 0.0034(19) 0.0011(19) C9 0.026(2) 0.0225(18) 0.039(3) -0.0019(17) 0.0079(18) 0.0006(15) C10 0.032(2) 0.029(2) 0.022(2) -0.0016(16) 0.0015(17) -0.0007(17) C11 0.045(3) 0.027(2) 0.044(3) -0.0016(19) 0.007(2) 0.0023(18) C12 0.052(3) 0.036(2) 0.063(3) -0.002(2) 0.006(3) 0.013(2) C13 0.0235(18) 0.0260(18) 0.026(2) -0.0024(16) 0.0047(16) 0.0006(15) C14 0.036(2) 0.036(2) 0.033(3) 0.0076(18) 0.0038(19) -0.0074(18) C15 0.035(2) 0.049(3) 0.030(2) 0.005(2) -0.0045(19) -0.003(2) C16 0.027(2) 0.033(2) 0.036(2) -0.0063(18) 0.0039(18) 0.0002(17) C17 0.031(2) 0.027(2) 0.031(2) 0.0025(17) 0.0068(18) 0.0011(16) C18 0.031(2) 0.0241(18) 0.026(2) -0.0027(16) 0.0021(17) 0.0012(16) C19 0.031(2) 0.046(2) 0.038(3) -0.006(2) 0.0013(19) -0.0050(19) C20 0.042(3) 0.057(3) 0.056(3) -0.020(3) -0.006(2) -0.006(2) C21 0.054(3) 0.092(4) 0.065(4) 0.009(3) -0.008(3) -0.043(3) C22 0.033(3) 0.067(3) 0.075(4) -0.022(3) -0.011(3) -0.001(2) C23 0.033(2) 0.0242(18) 0.028(2) 0.0027(16) 0.0103(17) 0.0006(16) C24 0.028(2) 0.040(2) 0.057(3) -0.018(2) 0.014(2) -0.0106(18) C25 0.028(2) 0.043(2) 0.054(3) -0.013(2) 0.016(2) -0.0047(19) C26 0.036(2) 0.0237(19) 0.028(2) 0.0004(16) 0.0092(18) -0.0012(16) C27 0.034(2) 0.041(2) 0.042(3) -0.013(2) -0.006(2) 0.0038(19) C28 0.027(2) 0.045(2) 0.040(3) -0.009(2) -0.0010(19) 0.0072(18) C29 0.038(2) 0.032(2) 0.032(2) -0.0044(18) 0.0054(19) 0.0028(18) C30 0.037(2) 0.039(2) 0.029(2) -0.0079(18) 0.0067(19) -0.0015(19) C31 0.043(3) 0.050(3) 0.041(3) -0.011(2) 0.004(2) 0.014(2) C32 0.054(3) 0.032(2) 0.044(3) -0.002(2) 0.008(2) 0.003(2) C33 0.104(8) 0.57(3) 0.217(14) -0.235(19) -0.122(9) 0.172(14) C34 0.064(4) 0.066(4) 0.070(4) 0.015(3) -0.002(3) 0.008(3) Cl1 0.171(3) 0.157(3) 0.326(5) -0.158(3) -0.093(3) 0.062(2) Cl2 0.265(5) 0.145(3) 0.201(4) -0.012(3) -0.049(3) -0.076(3) Cl3 0.1167(16) 0.0778(12) 0.1218(17) 0.0063(11) -0.0351(13) 0.0337(11) Cl4 0.0794(11) 0.0765(10) 0.0658(10) -0.0028(8) -0.0032(8) -0.0080(8) N1 0.039(2) 0.0289(17) 0.034(2) -0.0004(16) 0.0102(17) 0.0055(15) N2 0.044(2) 0.034(2) 0.045(2) 0.0018(17) 0.0077(18) 0.0031(17) N3 0.040(2) 0.066(3) 0.053(3) -0.015(2) -0.004(2) -0.004(2) N4 0.042(2) 0.0319(18) 0.034(2) 0.0016(16) 0.0128(17) 0.0043(15) O1 0.0361(16) 0.0320(15) 0.0439(18) 0.0016(13) 0.0178(14) -0.0067(12) O2 0.0324(15) 0.0256(14) 0.0359(16) 0.0021(12) 0.0076(13) -0.0007(11) _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 1.339(5) . ? C1 C6 1.366(5) . ? C1 C2 1.540(5) . ? C2 C7 1.482(5) . ? C2 C8 1.484(6) . ? C2 C3 1.584(5) . ? C3 C13 1.523(5) . ? C3 C4 1.524(5) . ? C3 H3 1.0000 . ? C4 C5 1.354(5) . ? C4 C23 1.491(5) . ? C5 C6 1.481(5) . ? C5 C10 1.495(5) . ? C6 C9 1.429(6) . ? C7 N2 1.145(5) . ? C8 N3 1.141(6) . ? C9 N4 1.158(5) . ? C10 O1 1.224(5) . ? C10 O2 1.320(5) . ? C11 O2 1.467(5) . ? C11 C12 1.508(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12C 0.9800 . ? C12 H12B 0.9800 . ? C12 H12A 0.9800 . ? C13 C14 1.385(6) . ? C13 C18 1.400(5) . ? C14 C15 1.388(6) . ? C14 H14 0.9500 . ? C15 C16 1.402(6) . ? C15 H15 0.9500 . ? C16 C17 1.393(6) . ? C16 C19 1.538(6) . ? C17 C18 1.382(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.526(6) . ? C19 C21 1.545(7) . ? C19 C22 1.547(7) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22C 0.9800 . ? C22 H22B 0.9800 . ? C22 H22A 0.9800 . ? C23 C24 1.389(6) . ? C23 C28 1.391(6) . ? C24 C25 1.399(6) . ? C24 H24 0.9500 . ? C25 C26 1.380(6) . ? C25 H25 0.9500 . ? C26 C27 1.405(6) . ? C26 C29 1.545(5) . ? C27 C28 1.383(6) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.533(6) . ? C29 C31 1.538(6) . ? C29 C32 1.546(6) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 Cl2 1.634(14) . ? C33 Cl1 1.738(16) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 Cl3 1.742(6) . ? C34 Cl4 1.767(6) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? N1 H1A 0.882(19) . ? N1 H1B 0.900(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 C6 126.5(4) . . ? N1 C1 C2 117.4(3) . . ? C6 C1 C2 116.1(3) . . ? C7 C2 C8 108.6(3) . . ? C7 C2 C1 111.3(3) . . ? C8 C2 C1 107.5(3) . . ? C7 C2 C3 110.2(3) . . ? C8 C2 C3 107.9(3) . . ? C1 C2 C3 111.2(3) . . ? C13 C3 C4 114.7(3) . . ? C13 C3 C2 111.8(3) . . ? C4 C3 C2 108.5(3) . . ? C13 C3 H3 107.2 . . ? C4 C3 H3 107.2 . . ? C2 C3 H3 107.2 . . ? C5 C4 C23 123.0(3) . . ? C5 C4 C3 120.1(3) . . ? C23 C4 C3 116.8(3) . . ? C4 C5 C6 121.1(3) . . ? C4 C5 C10 121.5(3) . . ? C6 C5 C10 117.2(3) . . ? C1 C6 C9 118.8(3) . . ? C1 C6 C5 121.6(3) . . ? C9 C6 C5 119.5(3) . . ? N2 C7 C2 178.6(4) . . ? N3 C8 C2 177.4(4) . . ? N4 C9 C6 179.5(4) . . ? O1 C10 O2 124.5(3) . . ? O1 C10 C5 122.1(3) . . ? O2 C10 C5 113.4(3) . . ? O2 C11 C12 106.0(3) . . ? O2 C11 H11A 110.5 . . ? C12 C11 H11A 110.5 . . ? O2 C11 H11B 110.5 . . ? C12 C11 H11B 110.5 . . ? H11A C11 H11B 108.7 . . ? C11 C12 H12C 109.5 . . ? C11 C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? C11 C12 H12A 109.5 . . ? H12C C12 H12A 109.5 . . ? H12B C12 H12A 109.5 . . ? C14 C13 C18 118.0(4) . . ? C14 C13 C3 123.4(3) . . ? C18 C13 C3 118.6(4) . . ? C13 C14 C15 120.6(4) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C16 122.2(4) . . ? C14 C15 H15 118.9 . . ? C16 C15 H15 118.9 . . ? C17 C16 C15 116.3(4) . . ? C17 C16 C19 123.0(4) . . ? C15 C16 C19 120.7(4) . . ? C18 C17 C16 122.0(4) . . ? C18 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? C17 C18 C13 120.9(4) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 119.6 . . ? C20 C19 C16 110.1(3) . . ? C20 C19 C21 108.4(4) . . ? C16 C19 C21 111.7(4) . . ? C20 C19 C22 109.0(4) . . ? C16 C19 C22 108.4(4) . . ? C21 C19 C22 109.3(4) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22C 109.5 . . ? C19 C22 H22B 109.5 . . ? H22C C22 H22B 109.5 . . ? C19 C22 H22A 109.5 . . ? H22C C22 H22A 109.5 . . ? H22B C22 H22A 109.5 . . ? C24 C23 C28 118.0(4) . . ? C24 C23 C4 121.0(4) . . ? C28 C23 C4 121.0(3) . . ? C23 C24 C25 120.3(4) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C26 C25 C24 122.2(4) . . ? C26 C25 H25 118.9 . . ? C24 C25 H25 118.9 . . ? C25 C26 C27 116.7(4) . . ? C25 C26 C29 122.9(4) . . ? C27 C26 C29 120.4(4) . . ? C28 C27 C26 121.5(4) . . ? C28 C27 H27 119.3 . . ? C26 C27 H27 119.3 . . ? C27 C28 C23 121.2(4) . . ? C27 C28 H28 119.4 . . ? C23 C28 H28 119.4 . . ? C30 C29 C31 109.4(3) . . ? C30 C29 C26 108.8(3) . . ? C31 C29 C26 111.0(4) . . ? C30 C29 C32 109.5(4) . . ? C31 C29 C32 108.5(4) . . ? C26 C29 C32 109.6(3) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? Cl2 C33 Cl1 115.1(6) . . ? Cl2 C33 H33A 108.5 . . ? Cl1 C33 H33A 108.5 . . ? Cl2 C33 H33B 108.5 . . ? Cl1 C33 H33B 108.5 . . ? H33A C33 H33B 107.5 . . ? Cl3 C34 Cl4 111.2(4) . . ? Cl3 C34 H34A 109.4 . . ? Cl4 C34 H34A 109.4 . . ? Cl3 C34 H34B 109.4 . . ? Cl4 C34 H34B 109.4 . . ? H34A C34 H34B 108.0 . . ? C1 N1 H1A 120(3) . . ? C1 N1 H1B 123(3) . . ? H1A N1 H1B 117(4) . . ? C10 O2 C11 116.6(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.395 _refine_diff_density_min -0.884 _refine_diff_density_rms 0.085