# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _publ_contact_author_name 'Dr Mario M. Q. Simoes' _publ_contact_author_address ; Department of Chemistry QOPNA University of Aveiro 3810-193 Aveiro Portugal ; _publ_contact_author_email msimoes@ua.pt _publ_contact_author_fax '+351 234 370084' _publ_contact_author_phone '+351 234 370713' loop_ _publ_author_name _publ_author_footnote _publ_author_address C.M.B.Neves . ; Department of Chemistry QOPNA University of Aveiro 3810-193 Aveiro Portugal ; M.M.Q.Simoes . ; Department of Chemistry QOPNA University of Aveiro 3810-193 Aveiro Portugal ; I.C.M.S.Santos . ; Department of Chemistry QOPNA University of Aveiro 3810-193 Aveiro Portugal ; M.G.P.M.S.Neves . ; Department of Chemistry QOPNA University of Aveiro 3810-193 Aveiro Portugal ; ; F.Almeida Paz ; . ; Department of Chemistry CICECO University of Aveiro CICECO 3810-193 Aveiro Portugal ; A.M.S.Silva . ; Department of Chemistry QOPNA University of Aveiro 3810-193 Aveiro Portugal ; J.A.S.Cavaleiro . ; Department of Chemistry QOPNA University of Aveiro 3810-193 Aveiro Portugal ; data_6 _database_code_depnum_ccdc_archive 'CCDC 862153' #TrackingRef '6.cif' # ======================================================================= _audit_creation_method 'SHELXL-97, manual editing plus enCIFer' _audit_creation_date '10 January 2012' # ======================================================================= #============================================================================= # GENERAL AND CHEMICAL DATA #============================================================================= _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H18 Cl4 N2 O3' _chemical_formula_sum 'C27 H18 Cl4 N2 O3' _chemical_formula_weight 560.23 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' #============================================================================== # CRYSTAL DATA #============================================================================== _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 12.923(4) _cell_length_b 8.679(3) _cell_length_c 23.217(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.312(11) _cell_angle_gamma 90.00 _cell_volume 2544.0(13) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 1498 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 17.96 _exptl_crystal_description Plate _exptl_crystal_colour Orange _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.498 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9565 _exptl_absorpt_correction_T_max 0.9950 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1997) ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Kappa CCD APEX II' _diffrn_measurement_method '\w / \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 25989 _diffrn_reflns_av_R_equivalents 0.1442 _diffrn_reflns_av_sigmaI/netI 0.1608 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4645 _reflns_number_gt 2096 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'APEX2 (Bruker, 2006)' _computing_data_reduction 'SAINT+ (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' #============================================================================== # REFINEMENT DATA #============================================================================== _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^)+(0.0498P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4645 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1766 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _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 Cl1 Cl 0.66011(11) 0.5834(2) 0.28146(6) 0.0895(6) Uani 1 1 d . . . Cl2 Cl 0.81470(10) 0.5027(2) 0.08535(6) 0.0702(5) Uani 1 1 d . . . Cl3 Cl 0.42445(10) -0.18700(14) 0.21772(5) 0.0495(4) Uani 1 1 d . . . Cl4 Cl 0.10906(9) -0.42656(14) 0.05081(5) 0.0449(4) Uani 1 1 d . . . N1 N 0.6436(3) 0.4999(4) 0.15627(15) 0.0354(10) Uani 1 1 d . . . N2 N 0.2545(3) -0.1693(4) 0.10913(14) 0.0321(9) Uani 1 1 d . . . H2 H 0.3106 -0.1368 0.0969 0.039 Uiso 1 1 calc R . . O1 O 0.3986(3) 0.8239(4) -0.01611(14) 0.0539(10) Uani 1 1 d . . . O2 O 0.3690(2) 0.3021(3) 0.06175(12) 0.0346(8) Uani 1 1 d . . . O3 O 0.3916(3) 0.0879(4) 0.11573(15) 0.0708(12) Uani 1 1 d . . . C1 C 0.7452(3) 0.5496(5) 0.18634(19) 0.0330(12) Uani 1 1 d . . . C2 C 0.7652(4) 0.5848(6) 0.24639(19) 0.0417(13) Uani 1 1 d . . . C3 C 0.8651(4) 0.6249(6) 0.2766(2) 0.0530(15) Uani 1 1 d . . . H3 H 0.8763 0.6524 0.3171 0.064 Uiso 1 1 calc R . . C4 C 0.9481(4) 0.6256(6) 0.2490(2) 0.0510(14) Uani 1 1 d . . . H4 H 1.0167 0.6542 0.2702 0.061 Uiso 1 1 calc R . . C5 C 0.9330(4) 0.5854(5) 0.1910(2) 0.0469(13) Uani 1 1 d . . . H5 H 0.9913 0.5817 0.1721 0.056 Uiso 1 1 calc R . . C6 C 0.8316(4) 0.5498(5) 0.15965(19) 0.0398(12) Uani 1 1 d . . . C7 C 0.5848(3) 0.5883(5) 0.11865(18) 0.0311(11) Uani 1 1 d . . . C8 C 0.6087(4) 0.7475(5) 0.10624(19) 0.0392(12) Uani 1 1 d . . . H8 H 0.6701 0.7958 0.1288 0.047 Uiso 1 1 calc R . . C9 C 0.5446(4) 0.8267(5) 0.06310(19) 0.0422(13) Uani 1 1 d . . . H9 H 0.5614 0.9307 0.0561 0.051 Uiso 1 1 calc R . . C10 C 0.4502(4) 0.7574(6) 0.02688(19) 0.0362(12) Uani 1 1 d . . . C11 C 0.4225(3) 0.6011(5) 0.04267(17) 0.0321(11) Uani 1 1 d . . . H11 H 0.3586 0.5561 0.0216 0.039 Uiso 1 1 calc R . . C12 C 0.4835(3) 0.5210(5) 0.08528(17) 0.0269(11) Uani 1 1 d . . . C13 C 0.4629(3) 0.3601(5) 0.10232(18) 0.0335(11) Uani 1 1 d . . . H13A H 0.5246 0.2940 0.1006 0.040 Uiso 1 1 calc R . . H13B H 0.4516 0.3582 0.1432 0.040 Uiso 1 1 calc R . . C15 C 0.2464(4) 0.0951(6) 0.03126(19) 0.0441(13) Uani 1 1 d . . . H15A H 0.2210 0.1743 0.0008 0.053 Uiso 1 1 calc R . . H15B H 0.2675 0.0033 0.0112 0.053 Uiso 1 1 calc R . . C14 C 0.3430(4) 0.1572(6) 0.0744(2) 0.0425(13) Uani 1 1 d . . . C16 C 0.1573(4) 0.0518(5) 0.06028(18) 0.0340(12) Uani 1 1 d . . . C17 C 0.0648(4) 0.1392(5) 0.0498(2) 0.0490(14) Uani 1 1 d . . . H17 H 0.0611 0.2279 0.0255 0.059 Uiso 1 1 calc R . . C18 C -0.0220(5) 0.1026(7) 0.0733(2) 0.0593(16) Uani 1 1 d . . . H18 H -0.0844 0.1639 0.0648 0.071 Uiso 1 1 calc R . . C19 C -0.0158(4) -0.0242(7) 0.1091(2) 0.0542(15) Uani 1 1 d . . . H19 H -0.0745 -0.0517 0.1256 0.065 Uiso 1 1 calc R . . C20 C 0.0754(4) -0.1126(6) 0.12136(19) 0.0411(13) Uani 1 1 d . . . H20 H 0.0790 -0.1986 0.1470 0.049 Uiso 1 1 calc R . . C21 C 0.1613(4) -0.0786(5) 0.09718(18) 0.0341(12) Uani 1 1 d . . . C22 C 0.2602(3) -0.3102(5) 0.13999(17) 0.0273(11) Uani 1 1 d . . . C23 C 0.1964(3) -0.4370(5) 0.11915(16) 0.0296(11) Uani 1 1 d . . . C24 C 0.2019(4) -0.5732(5) 0.1507(2) 0.0402(12) Uani 1 1 d . . . H24 H 0.1549 -0.6553 0.1363 0.048 Uiso 1 1 calc R . . C25 C 0.2754(4) -0.5899(6) 0.2029(2) 0.0449(13) Uani 1 1 d . . . H25 H 0.2786 -0.6827 0.2249 0.054 Uiso 1 1 calc R . . C26 C 0.3439(4) -0.4716(6) 0.2227(2) 0.0440(13) Uani 1 1 d . . . H26 H 0.3968 -0.4841 0.2577 0.053 Uiso 1 1 calc R . . C27 C 0.3363(3) -0.3331(5) 0.19189(18) 0.0338(12) 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 0.0564(10) 0.1655(18) 0.0495(9) -0.0155(10) 0.0177(7) -0.0136(12) Cl2 0.0496(9) 0.1174(13) 0.0442(8) -0.0111(8) 0.0114(6) 0.0005(9) Cl3 0.0438(8) 0.0507(8) 0.0471(7) 0.0003(6) -0.0060(6) -0.0114(7) Cl4 0.0508(8) 0.0381(7) 0.0405(7) -0.0051(6) -0.0021(6) -0.0074(7) N1 0.033(2) 0.037(2) 0.035(2) 0.0051(19) 0.0029(19) -0.003(2) N2 0.029(2) 0.033(2) 0.036(2) 0.0050(18) 0.0102(17) -0.004(2) O1 0.057(2) 0.045(2) 0.055(2) 0.0190(18) -0.0010(18) 0.000(2) O2 0.0312(18) 0.0271(19) 0.0400(18) 0.0057(14) -0.0045(14) -0.0069(16) O3 0.062(2) 0.046(2) 0.079(3) 0.035(2) -0.039(2) -0.027(2) C1 0.025(3) 0.034(3) 0.035(3) 0.003(2) -0.004(2) -0.002(2) C2 0.034(3) 0.053(3) 0.038(3) -0.001(3) 0.007(2) -0.007(3) C3 0.046(4) 0.062(4) 0.043(3) -0.011(3) -0.009(3) -0.009(3) C4 0.034(3) 0.050(4) 0.061(4) -0.008(3) -0.009(3) -0.009(3) C5 0.028(3) 0.041(3) 0.069(4) 0.006(3) 0.004(3) -0.003(3) C6 0.033(3) 0.040(3) 0.044(3) 0.001(2) 0.001(2) 0.002(3) C7 0.029(3) 0.036(3) 0.029(2) 0.000(2) 0.009(2) -0.003(3) C8 0.042(3) 0.029(3) 0.044(3) 0.002(2) 0.002(2) -0.012(3) C9 0.051(3) 0.025(3) 0.051(3) 0.007(2) 0.011(3) -0.005(3) C10 0.037(3) 0.038(3) 0.033(3) 0.006(2) 0.005(2) -0.003(3) C11 0.026(3) 0.038(3) 0.033(3) 0.006(2) 0.006(2) -0.008(2) C12 0.026(3) 0.026(3) 0.030(3) 0.005(2) 0.008(2) -0.002(2) C13 0.027(3) 0.034(3) 0.035(3) 0.004(2) -0.003(2) -0.009(2) C15 0.047(3) 0.037(3) 0.039(3) 0.008(2) -0.013(2) -0.008(3) C14 0.038(3) 0.032(3) 0.053(3) 0.007(3) 0.000(3) -0.008(3) C16 0.032(3) 0.022(3) 0.040(3) -0.005(2) -0.009(2) -0.009(3) C17 0.045(4) 0.022(3) 0.067(4) -0.015(3) -0.018(3) 0.001(3) C18 0.042(4) 0.047(4) 0.080(4) -0.028(3) -0.007(3) 0.014(3) C19 0.042(4) 0.060(4) 0.061(4) -0.021(3) 0.010(3) 0.005(3) C20 0.043(3) 0.035(3) 0.043(3) -0.010(2) 0.006(3) 0.001(3) C21 0.030(3) 0.031(3) 0.040(3) -0.013(2) 0.004(2) -0.004(3) C22 0.032(3) 0.027(3) 0.026(2) -0.001(2) 0.013(2) -0.003(2) C23 0.036(3) 0.032(3) 0.021(2) 0.000(2) 0.008(2) -0.003(2) C24 0.049(3) 0.029(3) 0.048(3) -0.006(3) 0.021(3) -0.009(3) C25 0.057(3) 0.037(3) 0.041(3) 0.009(3) 0.011(3) -0.002(3) C26 0.053(3) 0.046(3) 0.033(3) 0.008(3) 0.011(2) 0.004(3) C27 0.035(3) 0.032(3) 0.034(3) -0.004(2) 0.008(2) -0.008(2) _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. ; #============================================================================== # GEOMETRY #============================================================================== 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 C2 1.726(5) . ? Cl2 C6 1.741(5) . ? Cl3 C27 1.725(4) . ? Cl4 C23 1.742(4) . ? N1 C7 1.283(5) . ? N1 C1 1.416(5) . ? N2 C22 1.411(5) . ? N2 C21 1.416(5) . ? N2 H2 0.8800 . ? O1 C10 1.221(5) . ? O2 C14 1.350(5) . ? O2 C13 1.458(5) . ? O3 C14 1.191(5) . ? C1 C6 1.387(6) . ? C1 C2 1.396(6) . ? C2 C3 1.377(6) . ? C3 C4 1.361(6) . ? C3 H3 0.9500 . ? C4 C5 1.365(6) . ? C4 H4 0.9500 . ? C5 C6 1.391(6) . ? C5 H5 0.9500 . ? C7 C8 1.458(6) . ? C7 C12 1.491(6) . ? C8 C9 1.344(6) . ? C8 H8 0.9500 . ? C9 C10 1.456(6) . ? C9 H9 0.9500 . ? C10 C11 1.469(6) . ? C11 C12 1.323(5) . ? C11 H11 0.9500 . ? C12 C13 1.491(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C15 C16 1.501(6) . ? C15 C14 1.523(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.392(6) . ? C16 C21 1.414(6) . ? C17 C18 1.385(7) . ? C17 H17 0.9500 . ? C18 C19 1.371(7) . ? C18 H18 0.9500 . ? C19 C20 1.385(6) . ? C19 H19 0.9500 . ? C20 C21 1.378(6) . ? C20 H20 0.9500 . ? C22 C27 1.397(6) . ? C22 C23 1.398(6) . ? C23 C24 1.384(6) . ? C24 C25 1.379(6) . ? C24 H24 0.9500 . ? C25 C26 1.369(6) . ? C25 H25 0.9500 . ? C26 C27 1.391(6) . ? C26 H26 0.9500 . ? 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 C7 N1 C1 120.4(4) . . ? C22 N2 C21 122.1(4) . . ? C22 N2 H2 118.9 . . ? C21 N2 H2 118.9 . . ? C14 O2 C13 113.1(3) . . ? C6 C1 C2 116.8(4) . . ? C6 C1 N1 122.0(4) . . ? C2 C1 N1 120.9(4) . . ? C3 C2 C1 121.2(4) . . ? C3 C2 Cl1 120.6(4) . . ? C1 C2 Cl1 118.2(4) . . ? C4 C3 C2 120.6(5) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 120.1(5) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 119.6(5) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C1 C6 C5 121.6(4) . . ? C1 C6 Cl2 120.0(3) . . ? C5 C6 Cl2 118.4(4) . . ? N1 C7 C8 125.6(4) . . ? N1 C7 C12 116.5(4) . . ? C8 C7 C12 117.9(4) . . ? C9 C8 C7 120.6(4) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 121.8(4) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? O1 C10 C9 121.4(4) . . ? O1 C10 C11 121.4(4) . . ? C9 C10 C11 117.1(4) . . ? C12 C11 C10 122.3(4) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C11 C12 C13 125.4(4) . . ? C11 C12 C7 119.9(4) . . ? C13 C12 C7 114.6(4) . . ? O2 C13 C12 108.8(3) . . ? O2 C13 H13A 109.9 . . ? C12 C13 H13A 109.9 . . ? O2 C13 H13B 109.9 . . ? C12 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C16 C15 C14 113.1(4) . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? O3 C14 O2 122.2(4) . . ? O3 C14 C15 124.7(4) . . ? O2 C14 C15 113.1(4) . . ? C17 C16 C21 117.5(5) . . ? C17 C16 C15 119.8(4) . . ? C21 C16 C15 122.7(4) . . ? C18 C17 C16 122.9(5) . . ? C18 C17 H17 118.5 . . ? C16 C17 H17 118.5 . . ? C19 C18 C17 118.3(5) . . ? C19 C18 H18 120.8 . . ? C17 C18 H18 120.8 . . ? C18 C19 C20 120.4(5) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C21 C20 C19 121.5(5) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C20 C21 C16 119.3(4) . . ? C20 C21 N2 121.7(4) . . ? C16 C21 N2 118.9(4) . . ? C27 C22 C23 116.2(4) . . ? C27 C22 N2 120.8(4) . . ? C23 C22 N2 122.9(4) . . ? C24 C23 C22 121.9(4) . . ? C24 C23 Cl4 118.5(4) . . ? C22 C23 Cl4 119.6(3) . . ? C25 C24 C23 120.2(4) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C26 C25 C24 119.4(4) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? C25 C26 C27 120.4(4) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C26 C27 C22 121.7(4) . . ? C26 C27 Cl3 119.2(4) . . ? C22 C27 Cl3 119.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N1 C1 C6 -77.7(6) . . . . ? C7 N1 C1 C2 109.4(5) . . . . ? C6 C1 C2 C3 3.1(7) . . . . ? N1 C1 C2 C3 176.4(5) . . . . ? C6 C1 C2 Cl1 -179.2(4) . . . . ? N1 C1 C2 Cl1 -5.9(6) . . . . ? C1 C2 C3 C4 -2.5(8) . . . . ? Cl1 C2 C3 C4 179.8(4) . . . . ? C2 C3 C4 C5 -0.4(8) . . . . ? C3 C4 C5 C6 2.6(8) . . . . ? C2 C1 C6 C5 -0.9(7) . . . . ? N1 C1 C6 C5 -174.1(4) . . . . ? C2 C1 C6 Cl2 178.4(3) . . . . ? N1 C1 C6 Cl2 5.2(6) . . . . ? C4 C5 C6 C1 -1.9(7) . . . . ? C4 C5 C6 Cl2 178.8(4) . . . . ? C1 N1 C7 C8 -5.6(7) . . . . ? C1 N1 C7 C12 174.6(4) . . . . ? N1 C7 C8 C9 175.7(4) . . . . ? C12 C7 C8 C9 -4.6(6) . . . . ? C7 C8 C9 C10 -0.6(7) . . . . ? C8 C9 C10 O1 -172.1(5) . . . . ? C8 C9 C10 C11 5.2(7) . . . . ? O1 C10 C11 C12 172.8(4) . . . . ? C9 C10 C11 C12 -4.5(7) . . . . ? C10 C11 C12 C13 -177.6(4) . . . . ? C10 C11 C12 C7 -0.7(6) . . . . ? N1 C7 C12 C11 -175.0(4) . . . . ? C8 C7 C12 C11 5.2(6) . . . . ? N1 C7 C12 C13 2.2(6) . . . . ? C8 C7 C12 C13 -177.6(4) . . . . ? C14 O2 C13 C12 -178.9(4) . . . . ? C11 C12 C13 O2 4.0(6) . . . . ? C7 C12 C13 O2 -173.0(3) . . . . ? C13 O2 C14 O3 1.8(7) . . . . ? C13 O2 C14 C15 -178.7(4) . . . . ? C16 C15 C14 O3 59.1(7) . . . . ? C16 C15 C14 O2 -120.3(4) . . . . ? C14 C15 C16 C17 110.5(4) . . . . ? C14 C15 C16 C21 -71.4(6) . . . . ? C21 C16 C17 C18 -0.7(6) . . . . ? C15 C16 C17 C18 177.5(4) . . . . ? C16 C17 C18 C19 0.9(7) . . . . ? C17 C18 C19 C20 0.2(7) . . . . ? C18 C19 C20 C21 -1.5(7) . . . . ? C19 C20 C21 C16 1.7(6) . . . . ? C19 C20 C21 N2 -179.4(4) . . . . ? C17 C16 C21 C20 -0.6(6) . . . . ? C15 C16 C21 C20 -178.7(4) . . . . ? C17 C16 C21 N2 -179.5(4) . . . . ? C15 C16 C21 N2 2.4(6) . . . . ? C22 N2 C21 C20 8.4(6) . . . . ? C22 N2 C21 C16 -172.8(4) . . . . ? C21 N2 C22 C27 -122.3(4) . . . . ? C21 N2 C22 C23 62.0(5) . . . . ? C27 C22 C23 C24 5.4(6) . . . . ? N2 C22 C23 C24 -178.8(4) . . . . ? C27 C22 C23 Cl4 -173.1(3) . . . . ? N2 C22 C23 Cl4 2.8(6) . . . . ? C22 C23 C24 C25 -3.3(7) . . . . ? Cl4 C23 C24 C25 175.2(3) . . . . ? C23 C24 C25 C26 -1.0(7) . . . . ? C24 C25 C26 C27 2.8(7) . . . . ? C25 C26 C27 C22 -0.5(7) . . . . ? C25 C26 C27 Cl3 -179.5(4) . . . . ? C23 C22 C27 C26 -3.5(6) . . . . ? N2 C22 C27 C26 -179.5(4) . . . . ? C23 C22 C27 Cl3 175.5(3) . . . . ? N2 C22 C27 Cl3 -0.5(6) . . . . ? 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 H2 O3 0.88 2.21 2.833(5) 127.4 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.256 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.068 #============================================================================== # END #============================================================================== # Attachment '7.cif' data_7 _database_code_depnum_ccdc_archive 'CCDC 862154' #TrackingRef '7.cif' # ======================================================================= _audit_creation_method 'SHELXL-97, manual editing plus enCIFer' _audit_creation_date '10 January 2012' # ======================================================================= #============================================================================= # GENERAL AND CHEMICAL DATA #============================================================================= _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H13 Cl2 N O5' _chemical_formula_sum 'C17 H13 Cl2 N O5' _chemical_formula_weight 382.18 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' #============================================================================= # CRYSTAL DATA #============================================================================= _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 10.851(2) _cell_length_b 10.951(2) _cell_length_c 14.929(3) _cell_angle_alpha 87.827(12) _cell_angle_beta 84.530(11) _cell_angle_gamma 80.818(11) _cell_volume 1742.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2536 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 20.30 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.400 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9687 _exptl_absorpt_correction_T_max 0.9881 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1997) ; #============================================================================= # EXPERIMENTAL DATA #============================================================================= _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Kappa CCD APEX II' _diffrn_measurement_method '\w / \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 21445 _diffrn_reflns_av_R_equivalents 0.1184 _diffrn_reflns_av_sigmaI/netI 0.1378 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 25.35 _reflns_number_total 6267 _reflns_number_gt 3279 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'APEX2 (Bruker, 2006)' _computing_data_reduction 'SAINT+ (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' #============================================================================= # REFINEMENT DATA #============================================================================= _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^)+(0.1436P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6267 _refine_ls_number_parameters 455 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1683 _refine_ls_R_factor_gt 0.0956 _refine_ls_wR_factor_ref 0.2686 _refine_ls_wR_factor_gt 0.2254 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #============================================================================= # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS #============================================================================= 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 0.73228(18) 0.31848(16) 0.07518(12) 0.0593(5) Uani 1 1 d . . . Cl2 Cl 0.44819(19) 0.74327(16) 0.18474(12) 0.0608(6) Uani 1 1 d . . . Cl3 Cl -0.03186(18) 1.25593(16) 0.30763(11) 0.0564(5) Uani 1 1 d . . . Cl4 Cl 0.22047(17) 0.81844(16) 0.41224(12) 0.0552(5) Uani 1 1 d . . . N1 N 0.5679(5) 0.4808(5) 0.2065(3) 0.0388(12) Uani 1 1 d . . . N2 N 0.0711(5) 0.9876(5) 0.2901(3) 0.0378(12) Uani 1 1 d . . . O1 O 0.8513(4) 0.5118(4) 0.4783(3) 0.0551(13) Uani 1 1 d . . . O2 O 0.4679(4) 0.3314(4) 0.4605(3) 0.0399(10) Uani 1 1 d . . . O3 O 0.5224(8) 0.1367(5) 0.4187(4) 0.103(3) Uani 1 1 d . . . O4 O 0.3819(4) 0.4657(4) 0.3550(3) 0.0374(10) Uani 1 1 d . . . O5 O 0.2988(5) 0.3201(5) 0.2877(4) 0.0641(15) Uani 1 1 d . . . O6 O 0.3557(4) 1.0065(5) -0.0238(3) 0.0528(13) Uani 1 1 d . . . O7 O -0.0332(4) 0.8387(4) 0.0610(3) 0.0407(10) Uani 1 1 d . . . O8 O 0.0096(5) 0.6424(4) 0.1147(3) 0.0654(15) Uani 1 1 d . . . O9 O -0.1156(4) 0.9854(4) 0.1630(3) 0.0386(10) Uani 1 1 d . . . O10 O -0.2212(5) 0.8491(5) 0.2409(3) 0.0649(14) Uani 1 1 d . . . C1 C 0.6620(6) 0.4684(6) 0.0509(4) 0.0404(15) Uani 1 1 d . . . C2 C 0.6770(6) 0.5167(6) -0.0357(4) 0.0466(17) Uani 1 1 d . . . H2 H 0.7251 0.4688 -0.0823 0.056 Uiso 1 1 calc R . . C3 C 0.6202(6) 0.6367(6) -0.0530(4) 0.0470(17) Uani 1 1 d . . . H3 H 0.6287 0.6708 -0.1123 0.056 Uiso 1 1 calc R . . C4 C 0.5517(6) 0.7071(6) 0.0141(4) 0.0433(16) Uani 1 1 d . . . H4 H 0.5136 0.7895 0.0016 0.052 Uiso 1 1 calc R . . C5 C 0.5391(6) 0.6562(6) 0.1005(4) 0.0427(16) Uani 1 1 d . . . C6 C 0.5950(5) 0.5347(6) 0.1211(4) 0.0330(14) Uani 1 1 d . . . C7 C 0.6355(6) 0.4949(5) 0.2704(4) 0.0353(14) Uani 1 1 d . . . C8 C 0.7431(6) 0.5616(6) 0.2612(4) 0.0420(16) Uani 1 1 d . . . H8 H 0.7625 0.6029 0.2058 0.050 Uiso 1 1 calc R . . C9 C 0.8139(6) 0.5659(6) 0.3280(4) 0.0435(16) Uani 1 1 d . . . H9 H 0.8851 0.6069 0.3185 0.052 Uiso 1 1 calc R . . C10 C 0.7851(6) 0.5084(6) 0.4171(4) 0.0391(15) Uani 1 1 d . . . C11 C 0.6752(6) 0.4460(5) 0.4261(4) 0.0368(14) Uani 1 1 d . . . H11 H 0.6545 0.4073 0.4823 0.044 Uiso 1 1 calc R . . C12 C 0.6026(6) 0.4401(5) 0.3603(4) 0.0339(14) Uani 1 1 d . . . C13 C 0.4903(6) 0.3748(6) 0.3686(4) 0.0374(15) Uani 1 1 d . . . H13 H 0.5001 0.3059 0.3251 0.045 Uiso 1 1 calc R . . C14 C 0.4841(7) 0.2087(6) 0.4765(5) 0.0512(18) Uani 1 1 d . . . C15 C 0.4523(6) 0.1781(6) 0.5725(4) 0.0485(17) Uani 1 1 d . . . H15A H 0.3610 0.1917 0.5857 0.073 Uiso 1 1 calc R . . H15B H 0.4893 0.2312 0.6103 0.073 Uiso 1 1 calc R . . H15C H 0.4856 0.0912 0.5850 0.073 Uiso 1 1 calc R . . C16 C 0.2922(6) 0.4239(7) 0.3107(4) 0.0444(16) Uani 1 1 d . . . C17 C 0.1861(6) 0.5271(7) 0.2981(4) 0.0531(19) Uani 1 1 d . . . H17A H 0.1325 0.5028 0.2549 0.080 Uiso 1 1 calc R . . H17B H 0.2198 0.6013 0.2753 0.080 Uiso 1 1 calc R . . H17C H 0.1368 0.5447 0.3559 0.080 Uiso 1 1 calc R . . C18 C 0.1605(6) 0.9717(6) 0.4352(4) 0.0402(15) Uani 1 1 d . . . C19 C 0.1774(6) 1.0208(7) 0.5160(4) 0.0475(17) Uani 1 1 d . . . H19 H 0.2210 0.9712 0.5600 0.057 Uiso 1 1 calc R . . C20 C 0.1287(6) 1.1459(7) 0.5318(4) 0.0493(17) Uani 1 1 d . . . H20 H 0.1392 1.1809 0.5873 0.059 Uiso 1 1 calc R . . C21 C 0.0658(6) 1.2183(6) 0.4679(4) 0.0451(16) Uani 1 1 d . . . H21 H 0.0342 1.3030 0.4786 0.054 Uiso 1 1 calc R . . C22 C 0.0495(6) 1.1658(6) 0.3879(4) 0.0402(15) Uani 1 1 d . . . C23 C 0.0967(5) 1.0426(6) 0.3689(4) 0.0324(14) Uani 1 1 d . . . C24 C 0.1405(6) 0.9976(5) 0.2160(4) 0.0375(15) Uani 1 1 d . . . C25 C 0.2551(6) 1.0553(6) 0.2079(4) 0.0396(15) Uani 1 1 d . . . H25 H 0.2786 1.0931 0.2585 0.048 Uiso 1 1 calc R . . C26 C 0.3259(6) 1.0549(6) 0.1297(4) 0.0398(15) Uani 1 1 d . . . H26 H 0.4010 1.0897 0.1270 0.048 Uiso 1 1 calc R . . C27 C 0.2930(6) 1.0037(5) 0.0491(4) 0.0376(15) Uani 1 1 d . . . C28 C 0.1759(6) 0.9489(6) 0.0571(4) 0.0389(15) Uani 1 1 d . . . H28 H 0.1506 0.9154 0.0053 0.047 Uiso 1 1 calc R . . C29 C 0.1050(6) 0.9452(5) 0.1350(4) 0.0345(14) Uani 1 1 d . . . C30 C -0.0122(6) 0.8882(6) 0.1450(4) 0.0378(15) Uani 1 1 d . . . H30 H -0.0092 0.8233 0.1941 0.045 Uiso 1 1 calc R . . C31 C -0.0239(6) 0.7142(6) 0.0541(5) 0.0456(17) Uani 1 1 d . . . C32 C -0.0595(7) 0.6832(7) -0.0346(5) 0.066(2) Uani 1 1 d . . . H32A H -0.0234 0.5973 -0.0482 0.099 Uiso 1 1 calc R . . H32B H -0.0276 0.7386 -0.0811 0.099 Uiso 1 1 calc R . . H32C H -0.1510 0.6930 -0.0331 0.099 Uiso 1 1 calc R . . C33 C -0.2155(6) 0.9536(7) 0.2143(4) 0.0427(16) Uani 1 1 d . . . C34 C -0.3148(7) 1.0620(7) 0.2318(5) 0.0551(19) Uani 1 1 d . . . H34A H -0.3848 1.0363 0.2704 0.083 Uiso 1 1 calc R . . H34B H -0.3445 1.0959 0.1746 0.083 Uiso 1 1 calc R . . H34C H -0.2807 1.1254 0.2620 0.083 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0637(12) 0.0386(10) 0.0650(11) 0.0052(8) 0.0038(9) 0.0169(9) Cl2 0.0748(14) 0.0409(10) 0.0561(11) 0.0034(8) 0.0047(9) 0.0161(9) Cl3 0.0677(12) 0.0401(10) 0.0556(10) 0.0023(8) -0.0154(9) 0.0140(9) Cl4 0.0552(11) 0.0418(10) 0.0631(11) 0.0020(8) -0.0141(9) 0.0133(8) N1 0.039(3) 0.034(3) 0.039(3) 0.004(2) -0.005(2) 0.006(2) N2 0.035(3) 0.036(3) 0.040(3) 0.001(2) -0.005(2) 0.003(2) O1 0.048(3) 0.058(3) 0.060(3) -0.005(2) -0.022(3) 0.001(2) O2 0.046(3) 0.031(2) 0.040(2) 0.0035(19) -0.002(2) -0.002(2) O3 0.187(7) 0.038(3) 0.062(3) 0.007(3) 0.037(4) 0.022(4) O4 0.034(2) 0.032(2) 0.043(2) -0.0033(19) -0.0103(19) 0.0079(19) O5 0.062(3) 0.044(3) 0.090(4) -0.009(3) -0.023(3) -0.008(3) O6 0.043(3) 0.064(3) 0.047(3) 0.001(2) 0.007(2) -0.003(3) O7 0.047(3) 0.028(2) 0.045(2) 0.0005(19) -0.011(2) 0.002(2) O8 0.084(4) 0.037(3) 0.071(3) 0.008(3) -0.017(3) 0.009(3) O9 0.037(2) 0.032(2) 0.043(2) 0.0077(19) -0.003(2) 0.002(2) O10 0.053(3) 0.049(3) 0.086(4) 0.020(3) 0.012(3) -0.002(3) C1 0.038(4) 0.033(3) 0.047(4) 0.007(3) -0.008(3) 0.006(3) C2 0.054(4) 0.045(4) 0.039(4) -0.002(3) 0.005(3) -0.007(4) C3 0.055(4) 0.045(4) 0.041(4) 0.006(3) -0.008(3) -0.008(4) C4 0.047(4) 0.035(4) 0.046(4) 0.012(3) -0.007(3) 0.000(3) C5 0.041(4) 0.038(4) 0.047(4) -0.003(3) -0.006(3) 0.002(3) C6 0.030(3) 0.037(3) 0.032(3) 0.002(3) -0.005(3) -0.004(3) C7 0.041(4) 0.025(3) 0.036(3) 0.003(3) -0.001(3) 0.003(3) C8 0.041(4) 0.039(4) 0.045(4) 0.004(3) -0.003(3) -0.005(3) C9 0.028(3) 0.037(4) 0.063(4) -0.001(3) -0.003(3) 0.001(3) C10 0.033(3) 0.033(3) 0.050(4) -0.005(3) -0.010(3) 0.004(3) C11 0.037(4) 0.027(3) 0.042(3) 0.001(3) 0.000(3) 0.005(3) C12 0.035(3) 0.027(3) 0.036(3) 0.002(3) -0.003(3) 0.008(3) C13 0.043(4) 0.031(3) 0.033(3) -0.002(3) -0.002(3) 0.011(3) C14 0.064(5) 0.029(4) 0.051(4) 0.006(3) 0.010(4) 0.011(3) C15 0.049(4) 0.041(4) 0.052(4) 0.014(3) 0.002(3) -0.004(3) C16 0.037(4) 0.060(5) 0.036(3) 0.002(3) -0.002(3) -0.008(4) C17 0.046(4) 0.065(5) 0.047(4) -0.003(4) -0.014(3) 0.003(4) C18 0.038(4) 0.033(3) 0.044(4) 0.000(3) -0.002(3) 0.007(3) C19 0.046(4) 0.052(4) 0.042(4) 0.001(3) -0.013(3) 0.005(3) C20 0.048(4) 0.054(5) 0.046(4) -0.011(3) -0.006(3) -0.006(4) C21 0.041(4) 0.044(4) 0.048(4) -0.008(3) -0.004(3) -0.001(3) C22 0.038(4) 0.040(4) 0.038(3) 0.009(3) -0.002(3) 0.003(3) C23 0.025(3) 0.037(3) 0.033(3) 0.006(3) -0.003(3) 0.000(3) C24 0.037(4) 0.024(3) 0.046(4) 0.008(3) -0.005(3) 0.011(3) C25 0.039(4) 0.035(4) 0.041(3) 0.002(3) -0.006(3) 0.005(3) C26 0.029(3) 0.038(4) 0.052(4) 0.006(3) -0.007(3) -0.002(3) C27 0.033(4) 0.029(3) 0.046(4) 0.003(3) -0.004(3) 0.009(3) C28 0.048(4) 0.029(3) 0.036(3) -0.001(3) -0.010(3) 0.009(3) C29 0.035(3) 0.024(3) 0.041(3) 0.002(3) -0.011(3) 0.011(3) C30 0.039(4) 0.035(3) 0.038(3) 0.002(3) -0.011(3) 0.003(3) C31 0.033(4) 0.033(4) 0.068(4) 0.003(3) -0.013(3) 0.006(3) C32 0.060(5) 0.048(5) 0.089(6) -0.015(4) -0.027(4) 0.010(4) C33 0.039(4) 0.049(4) 0.037(3) 0.005(3) 0.000(3) -0.002(3) C34 0.052(4) 0.050(4) 0.054(4) -0.002(3) 0.004(4) 0.014(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; #============================================================================= # GEOMETRY #============================================================================= 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 C1 1.737(6) . ? Cl2 C5 1.737(7) . ? Cl3 C22 1.739(6) . ? Cl4 C18 1.735(6) . ? N1 C7 1.286(7) . ? N1 C6 1.410(7) . ? N2 C24 1.288(7) . ? N2 C23 1.412(7) . ? O1 C10 1.220(7) . ? O2 C14 1.342(7) . ? O2 C13 1.446(7) . ? O3 C14 1.191(8) . ? O4 C16 1.372(8) . ? O4 C13 1.440(7) . ? O5 C16 1.189(8) . ? O6 C27 1.229(7) . ? O7 C31 1.357(7) . ? O7 C30 1.436(7) . ? O8 C31 1.220(7) . ? O9 C33 1.351(7) . ? O9 C30 1.431(7) . ? O10 C33 1.206(8) . ? C1 C6 1.378(9) . ? C1 C2 1.383(8) . ? C2 C3 1.385(9) . ? C2 H2 0.9500 . ? C3 C4 1.373(9) . ? C3 H3 0.9500 . ? C4 C5 1.390(8) . ? C4 H4 0.9500 . ? C5 C6 1.407(8) . ? C7 C8 1.466(9) . ? C7 C12 1.486(8) . ? C8 C9 1.322(8) . ? C8 H8 0.9500 . ? C9 C10 1.477(9) . ? C9 H9 0.9500 . ? C10 C11 1.460(9) . ? C11 C12 1.325(8) . ? C11 H11 0.9500 . ? C12 C13 1.501(9) . ? C13 H13 1.0000 . ? C14 C15 1.480(9) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.499(9) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.378(9) . ? C18 C23 1.401(8) . ? C19 C20 1.408(9) . ? C19 H19 0.9500 . ? C20 C21 1.378(9) . ? C20 H20 0.9500 . ? C21 C22 1.383(8) . ? C21 H21 0.9500 . ? C22 C23 1.394(8) . ? C24 C29 1.468(8) . ? C24 C25 1.476(9) . ? C25 C26 1.334(8) . ? C25 H25 0.9500 . ? C26 C27 1.446(8) . ? C26 H26 0.9500 . ? C27 C28 1.482(9) . ? C28 C29 1.335(8) . ? C28 H28 0.9500 . ? C29 C30 1.496(9) . ? C30 H30 1.0000 . ? C31 C32 1.480(9) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C34 1.483(9) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 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 C7 N1 C6 119.1(5) . . ? C24 N2 C23 120.1(5) . . ? C14 O2 C13 117.8(5) . . ? C16 O4 C13 114.7(5) . . ? C31 O7 C30 118.9(5) . . ? C33 O9 C30 116.0(5) . . ? C6 C1 C2 123.1(6) . . ? C6 C1 Cl1 117.1(5) . . ? C2 C1 Cl1 119.8(5) . . ? C1 C2 C3 118.5(6) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 121.1(6) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.0(6) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 121.8(6) . . ? C4 C5 Cl2 119.1(5) . . ? C6 C5 Cl2 119.1(5) . . ? C1 C6 C5 116.5(5) . . ? C1 C6 N1 122.8(6) . . ? C5 C6 N1 120.2(5) . . ? N1 C7 C8 124.8(5) . . ? N1 C7 C12 117.9(5) . . ? C8 C7 C12 117.3(5) . . ? C9 C8 C7 121.8(6) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C10 121.6(6) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? O1 C10 C11 122.7(6) . . ? O1 C10 C9 121.4(6) . . ? C11 C10 C9 115.9(5) . . ? C12 C11 C10 123.8(6) . . ? C12 C11 H11 118.1 . . ? C10 C11 H11 118.1 . . ? C11 C12 C7 119.4(6) . . ? C11 C12 C13 124.2(5) . . ? C7 C12 C13 116.3(5) . . ? O4 C13 O2 104.1(5) . . ? O4 C13 C12 107.7(5) . . ? O2 C13 C12 109.5(5) . . ? O4 C13 H13 111.7 . . ? O2 C13 H13 111.7 . . ? C12 C13 H13 111.7 . . ? O3 C14 O2 122.0(6) . . ? O3 C14 C15 126.2(6) . . ? O2 C14 C15 111.8(6) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O5 C16 O4 123.9(6) . . ? O5 C16 C17 126.2(6) . . ? O4 C16 C17 109.9(6) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 122.0(6) . . ? C19 C18 Cl4 120.2(5) . . ? C23 C18 Cl4 117.8(5) . . ? C18 C19 C20 118.7(6) . . ? C18 C19 H19 120.7 . . ? C20 C19 H19 120.7 . . ? C21 C20 C19 120.8(6) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C20 C21 C22 119.0(6) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C21 C22 C23 122.3(5) . . ? C21 C22 Cl3 119.2(5) . . ? C23 C22 Cl3 118.5(5) . . ? C22 C23 C18 117.3(5) . . ? C22 C23 N2 121.6(5) . . ? C18 C23 N2 120.8(6) . . ? N2 C24 C29 117.8(6) . . ? N2 C24 C25 124.3(6) . . ? C29 C24 C25 117.9(5) . . ? C26 C25 C24 120.4(6) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C27 122.6(6) . . ? C25 C26 H26 118.7 . . ? C27 C26 H26 118.7 . . ? O6 C27 C26 123.0(6) . . ? O6 C27 C28 120.3(6) . . ? C26 C27 C28 116.7(5) . . ? C29 C28 C27 121.9(6) . . ? C29 C28 H28 119.0 . . ? C27 C28 H28 119.0 . . ? C28 C29 C24 120.4(6) . . ? C28 C29 C30 122.8(5) . . ? C24 C29 C30 116.8(5) . . ? O9 C30 O7 104.9(4) . . ? O9 C30 C29 107.6(5) . . ? O7 C30 C29 110.4(5) . . ? O9 C30 H30 111.2 . . ? O7 C30 H30 111.2 . . ? C29 C30 H30 111.2 . . ? O8 C31 O7 122.3(6) . . ? O8 C31 C32 127.3(6) . . ? O7 C31 C32 110.4(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 . . ? O10 C33 O9 123.0(6) . . ? O10 C33 C34 125.5(7) . . ? O9 C33 C34 111.5(6) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.1(10) . . . . ? Cl1 C1 C2 C3 -179.8(5) . . . . ? C1 C2 C3 C4 0.8(10) . . . . ? C2 C3 C4 C5 -0.4(10) . . . . ? C3 C4 C5 C6 0.3(10) . . . . ? C3 C4 C5 Cl2 -177.8(5) . . . . ? C2 C1 C6 C5 1.0(9) . . . . ? Cl1 C1 C6 C5 179.7(4) . . . . ? C2 C1 C6 N1 172.5(6) . . . . ? Cl1 C1 C6 N1 -8.8(8) . . . . ? C4 C5 C6 C1 -0.6(9) . . . . ? Cl2 C5 C6 C1 177.6(5) . . . . ? C4 C5 C6 N1 -172.3(6) . . . . ? Cl2 C5 C6 N1 5.9(8) . . . . ? C7 N1 C6 C1 99.6(7) . . . . ? C7 N1 C6 C5 -89.2(7) . . . . ? C6 N1 C7 C8 -1.5(9) . . . . ? C6 N1 C7 C12 178.4(5) . . . . ? N1 C7 C8 C9 -175.5(6) . . . . ? C12 C7 C8 C9 4.7(9) . . . . ? C7 C8 C9 C10 -2.9(10) . . . . ? C8 C9 C10 O1 179.4(6) . . . . ? C8 C9 C10 C11 0.7(9) . . . . ? O1 C10 C11 C12 -179.3(6) . . . . ? C9 C10 C11 C12 -0.6(9) . . . . ? C10 C11 C12 C7 2.6(9) . . . . ? C10 C11 C12 C13 179.3(6) . . . . ? N1 C7 C12 C11 175.7(6) . . . . ? C8 C7 C12 C11 -4.5(8) . . . . ? N1 C7 C12 C13 -1.2(8) . . . . ? C8 C7 C12 C13 178.6(5) . . . . ? C16 O4 C13 O2 -99.3(5) . . . . ? C16 O4 C13 C12 144.5(5) . . . . ? C14 O2 C13 O4 131.7(6) . . . . ? C14 O2 C13 C12 -113.3(6) . . . . ? C11 C12 C13 O4 118.2(6) . . . . ? C7 C12 C13 O4 -65.0(6) . . . . ? C11 C12 C13 O2 5.6(8) . . . . ? C7 C12 C13 O2 -177.7(5) . . . . ? C13 O2 C14 O3 4.2(11) . . . . ? C13 O2 C14 C15 -177.4(5) . . . . ? C13 O4 C16 O5 2.8(9) . . . . ? C13 O4 C16 C17 -178.4(5) . . . . ? C23 C18 C19 C20 0.1(10) . . . . ? Cl4 C18 C19 C20 179.3(5) . . . . ? C18 C19 C20 C21 -0.3(10) . . . . ? C19 C20 C21 C22 0.9(10) . . . . ? C20 C21 C22 C23 -1.3(10) . . . . ? C20 C21 C22 Cl3 179.0(5) . . . . ? C21 C22 C23 C18 1.1(9) . . . . ? Cl3 C22 C23 C18 -179.2(5) . . . . ? C21 C22 C23 N2 175.0(6) . . . . ? Cl3 C22 C23 N2 -5.3(8) . . . . ? C19 C18 C23 C22 -0.5(9) . . . . ? Cl4 C18 C23 C22 -179.7(5) . . . . ? C19 C18 C23 N2 -174.4(6) . . . . ? Cl4 C18 C23 N2 6.4(8) . . . . ? C24 N2 C23 C22 86.0(7) . . . . ? C24 N2 C23 C18 -100.3(7) . . . . ? C23 N2 C24 C29 -176.3(5) . . . . ? C23 N2 C24 C25 5.3(8) . . . . ? N2 C24 C25 C26 175.8(6) . . . . ? C29 C24 C25 C26 -2.6(8) . . . . ? C24 C25 C26 C27 2.6(9) . . . . ? C25 C26 C27 O6 177.6(6) . . . . ? C25 C26 C27 C28 -0.8(8) . . . . ? O6 C27 C28 C29 -179.4(6) . . . . ? C26 C27 C28 C29 -0.9(8) . . . . ? C27 C28 C29 C24 0.8(8) . . . . ? C27 C28 C29 C30 -178.8(5) . . . . ? N2 C24 C29 C28 -177.6(5) . . . . ? C25 C24 C29 C28 0.9(8) . . . . ? N2 C24 C29 C30 2.0(7) . . . . ? C25 C24 C29 C30 -179.5(5) . . . . ? C33 O9 C30 O7 92.8(5) . . . . ? C33 O9 C30 C29 -149.6(5) . . . . ? C31 O7 C30 O9 -131.8(5) . . . . ? C31 O7 C30 C29 112.6(6) . . . . ? C28 C29 C30 O9 -113.1(6) . . . . ? C24 C29 C30 O9 67.3(6) . . . . ? C28 C29 C30 O7 0.9(7) . . . . ? C24 C29 C30 O7 -178.7(4) . . . . ? C30 O7 C31 O8 -4.8(9) . . . . ? C30 O7 C31 C32 175.1(5) . . . . ? C30 O9 C33 O10 -2.8(8) . . . . ? C30 O9 C33 C34 177.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.681 _refine_diff_density_min -0.865 _refine_diff_density_rms 0.136 #============================================================================= # END #=============================================================================