# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Raju Mondal' _publ_contact_author_email ICRM@IACS.RES.IN _publ_section_title ; Polymorphism study of a three-component system ; loop_ _publ_author_name 'Raju Mondal' 'Judith A. K. Howard' # Attachment 'Complex_1.cif' data_03rmd082 _database_code_depnum_ccdc_archive 'CCDC 669315' #TrackingRef 'Complex_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;1,5-dichloro-trans-9,10-diethynyl-9,10-dihydroxy-9,10- dihydroanthracene ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H29 Cl2 N O4' _chemical_formula_weight 490.40 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.6450(5) _cell_length_b 11.5719(4) _cell_length_c 15.0033(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.8960(10) _cell_angle_gamma 90.00 _cell_volume 2478.48(15) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6235 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.406 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 6K CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 26485 _diffrn_reflns_av_R_equivalents 0.0481 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5684 _reflns_number_gt 4269 _reflns_threshold_expression I>2\s(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^)+(0.0647P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5684 _refine_ls_number_parameters 426 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1041 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _refine_ls_shift/su_max 0.002 _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 0.64202(3) 0.13025(4) 1.24507(3) 0.02663(12) Uani 1 1 d . . . Cl1' Cl 0.51000(4) 0.15018(4) 0.54537(3) 0.03461(13) Uani 1 1 d . . . O1 O 0.47139(8) 0.18765(9) 1.09114(8) 0.0203(3) Uani 1 1 d . . . H1 H 0.4795(16) 0.212(2) 1.0453(16) 0.049(7) Uiso 1 1 d . . . O1' O 0.45020(8) 0.36901(10) 0.62359(8) 0.0225(3) Uani 1 1 d . . . H1' H 0.4668(16) 0.3610(19) 0.6792(17) 0.045(7) Uiso 1 1 d . . . C1 C 0.65619(12) 0.06094(13) 1.14593(10) 0.0200(3) Uani 1 1 d . . . N1 N 0.67583(12) 0.40250(13) 0.98180(10) 0.0254(3) Uani 1 1 d . . . H111 H 0.6268(14) 0.3675(17) 0.9692(14) 0.028(6) Uiso 1 1 d . . . C1' C 0.49431(12) 0.25620(14) 0.46075(11) 0.0236(4) Uani 1 1 d . . . O2 O 0.51736(9) 0.35242(11) 0.80493(8) 0.0316(3) Uani 1 1 d . . . C2 C 0.74642(12) 0.03309(14) 1.14121(12) 0.0231(4) Uani 1 1 d . . . H2 H 0.7952(13) 0.0547(16) 1.1871(13) 0.028(5) Uiso 1 1 d . . . C2' C 0.47800(13) 0.21680(16) 0.37215(12) 0.0287(4) Uani 1 1 d . . . H2' H 0.4815(14) 0.1370(17) 0.3635(14) 0.035(5) Uiso 1 1 d . . . O3 O 0.50835(8) 0.29338(10) 0.94276(7) 0.0252(3) Uani 1 1 d . . . C3 C 0.76224(12) -0.02700(15) 1.06621(12) 0.0256(4) Uani 1 1 d . . . H3A H 0.8215(14) -0.0511(16) 1.0607(13) 0.032(5) Uiso 1 1 d . . . C3' C 0.46268(13) 0.29447(16) 0.30044(12) 0.0293(4) Uani 1 1 d . . . H3' H 0.4497(13) 0.2702(16) 0.2421(14) 0.028(5) Uiso 1 1 d . . . C4 C 0.68781(12) -0.05607(14) 0.99681(12) 0.0219(3) Uani 1 1 d . . . H4 H 0.7001(12) -0.0981(16) 0.9436(12) 0.025(5) Uiso 1 1 d . . . C4' C 0.46239(12) 0.41144(15) 0.31877(11) 0.0245(4) Uani 1 1 d . . . H4' H 0.4514(12) 0.4683(15) 0.2712(12) 0.020(4) Uiso 1 1 d . . . C9 C 0.47906(11) 0.06547(13) 1.08145(10) 0.0170(3) Uani 1 1 d . . . C9' C 0.51979(11) 0.41564(13) 0.58103(10) 0.0184(3) Uani 1 1 d . . . C11 C 0.57825(11) 0.03285(13) 1.07529(10) 0.0165(3) Uani 1 1 d . . . C11' C 0.49708(11) 0.37541(13) 0.48202(10) 0.0185(3) Uani 1 1 d . . . C12 C 0.59646(11) -0.02606(13) 1.00053(10) 0.0169(3) Uani 1 1 d . . . C12' C 0.47969(11) 0.45206(13) 0.40888(10) 0.0181(3) Uani 1 1 d . . . C15 C 0.45629(11) 0.00907(14) 1.16288(10) 0.0202(3) Uani 1 1 d . . . C15' C 0.61485(12) 0.37422(14) 0.62685(11) 0.0232(4) Uani 1 1 d . . . C16 C 0.43510(14) -0.04619(16) 1.22120(12) 0.0312(4) Uani 1 1 d . . . H16 H 0.4166(16) -0.089(2) 1.2659(16) 0.055(7) Uiso 1 1 d . . . C16' C 0.69032(15) 0.34397(18) 0.66615(13) 0.0343(4) Uani 1 1 d . . . H16' H 0.7526(18) 0.320(2) 0.6996(17) 0.061(7) Uiso 1 1 d . . . C19 C 0.6510(2) 0.4125(2) 1.14090(14) 0.0443(6) Uani 1 1 d . . . H19C H 0.6370(16) 0.498(2) 1.1384(14) 0.052(7) Uiso 1 1 d . . . H19B H 0.5936(18) 0.378(2) 1.1231(17) 0.060(8) Uiso 1 1 d . . . H19A H 0.6762(15) 0.3837(19) 1.2027(16) 0.047(6) Uiso 1 1 d . . . C20 C 0.71561(16) 0.37840(17) 1.08084(13) 0.0361(5) Uani 1 1 d . . . H2OC H 0.7775(15) 0.4182(17) 1.0985(13) 0.032(5) Uiso 1 1 d . . . H20A H 0.7289(14) 0.2948(19) 1.0849(14) 0.042(6) Uiso 1 1 d . . . C21 C 0.64940(14) 0.52718(16) 0.96205(13) 0.0307(4) Uani 1 1 d . . . H21B H 0.6238(13) 0.5293(16) 0.8971(14) 0.032(5) Uiso 1 1 d . . . H21A H 0.6016(13) 0.5502(16) 0.9971(13) 0.031(5) Uiso 1 1 d . . . C22 C 0.73044(18) 0.61083(18) 0.98660(18) 0.0446(5) Uani 1 1 d . . . H22C H 0.7782(17) 0.588(2) 0.9523(16) 0.057(7) Uiso 1 1 d . . . H22B H 0.7616(19) 0.608(2) 1.0556(19) 0.071(8) Uiso 1 1 d . . . H22A H 0.7023(16) 0.686(2) 0.9675(15) 0.051(6) Uiso 1 1 d . . . C23 C 0.73658(15) 0.35883(16) 0.92109(14) 0.0313(4) Uani 1 1 d . . . H23A H 0.7068(13) 0.3837(16) 0.8605(14) 0.030(5) Uiso 1 1 d . . . H23B H 0.7973(15) 0.4002(17) 0.9367(13) 0.037(5) Uiso 1 1 d . . . C24 C 0.74607(17) 0.22862(18) 0.92434(17) 0.0387(5) Uani 1 1 d . . . H24B H 0.7726(16) 0.2080(19) 0.8771(16) 0.046(6) Uiso 1 1 d . . . H24A H 0.7825(16) 0.2051(19) 0.9840(16) 0.049(6) Uiso 1 1 d . . . H24C H 0.6843(16) 0.1951(18) 0.9154(14) 0.040(6) Uiso 1 1 d . . . C25 C 0.38464(14) 0.24003(17) 0.81696(14) 0.0279(4) Uani 1 1 d . . . H25C H 0.381(3) 0.154(4) 0.827(4) 0.035(12) Uiso 0.50 1 d P . . H25B H 0.397(3) 0.180(5) 0.779(3) 0.040(12) Uiso 0.50 1 d P . . H25A H 0.340(3) 0.260(4) 0.859(3) 0.032(11) Uiso 0.50 1 d P . . H25F H 0.365(3) 0.249(3) 0.749(3) 0.015(8) Uiso 0.50 1 d P . . H25E H 0.359(3) 0.195(5) 0.859(3) 0.034(12) Uiso 0.50 1 d P . . H25D H 0.339(3) 0.288(3) 0.789(3) 0.024(10) Uiso 0.50 1 d P . . C26 C 0.47608(12) 0.29926(14) 0.85681(11) 0.0220(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0289(2) 0.0319(2) 0.0168(2) -0.00683(16) 0.00041(16) -0.00214(17) Cl1' 0.0518(3) 0.0198(2) 0.0305(2) 0.00466(17) 0.0055(2) 0.00290(19) O1 0.0293(7) 0.0163(5) 0.0167(6) -0.0009(4) 0.0083(5) 0.0000(5) O1' 0.0241(6) 0.0288(6) 0.0161(6) 0.0039(5) 0.0073(5) -0.0014(5) C1 0.0250(9) 0.0193(8) 0.0151(7) 0.0001(6) 0.0033(6) -0.0004(6) N1 0.0275(9) 0.0228(7) 0.0240(8) 0.0001(6) 0.0019(6) -0.0039(6) C1' 0.0275(9) 0.0204(8) 0.0231(8) 0.0010(7) 0.0062(7) 0.0026(7) O2 0.0381(8) 0.0387(7) 0.0183(6) 0.0050(5) 0.0068(5) -0.0106(6) C2 0.0203(9) 0.0243(8) 0.0218(8) 0.0008(7) -0.0018(7) -0.0035(7) C2' 0.0349(10) 0.0230(9) 0.0287(9) -0.0074(7) 0.0081(8) 0.0013(8) O3 0.0310(7) 0.0281(6) 0.0166(6) 0.0028(5) 0.0055(5) -0.0047(5) C3 0.0176(9) 0.0287(9) 0.0304(9) 0.0005(7) 0.0053(7) 0.0011(7) C3' 0.0368(11) 0.0333(10) 0.0191(9) -0.0083(7) 0.0090(8) -0.0010(8) C4 0.0221(9) 0.0229(8) 0.0220(8) -0.0015(7) 0.0076(7) -0.0007(7) C4' 0.0298(10) 0.0289(9) 0.0157(8) -0.0006(7) 0.0066(7) -0.0010(7) C9 0.0211(8) 0.0176(7) 0.0131(7) -0.0005(6) 0.0056(6) 0.0007(6) C9' 0.0197(8) 0.0211(8) 0.0150(7) 0.0030(6) 0.0054(6) 0.0003(6) C11 0.0197(8) 0.0153(7) 0.0138(7) 0.0021(6) 0.0023(6) -0.0023(6) C11' 0.0183(8) 0.0212(8) 0.0170(8) -0.0012(6) 0.0063(6) 0.0017(6) C12 0.0183(8) 0.0167(7) 0.0159(7) 0.0026(6) 0.0042(6) -0.0004(6) C12' 0.0171(8) 0.0221(8) 0.0160(7) -0.0018(6) 0.0057(6) 0.0000(6) C15 0.0230(9) 0.0214(8) 0.0168(8) -0.0038(6) 0.0056(6) -0.0004(6) C15' 0.0263(10) 0.0276(9) 0.0168(8) 0.0011(7) 0.0072(7) 0.0022(7) C16 0.0411(11) 0.0336(10) 0.0201(9) 0.0008(8) 0.0093(8) -0.0078(8) C16' 0.0307(11) 0.0505(12) 0.0229(9) 0.0045(8) 0.0083(8) 0.0081(9) C19 0.0698(17) 0.0380(12) 0.0230(10) -0.0048(9) 0.0064(11) -0.0144(12) C20 0.0475(13) 0.0284(10) 0.0267(10) 0.0038(8) -0.0036(9) -0.0040(9) C21 0.0392(11) 0.0252(9) 0.0259(10) 0.0037(7) 0.0034(9) 0.0016(8) C22 0.0529(15) 0.0243(10) 0.0565(15) 0.0027(10) 0.0121(12) -0.0065(10) C23 0.0303(11) 0.0311(10) 0.0334(11) 0.0009(8) 0.0089(8) -0.0010(8) C24 0.0376(13) 0.0309(10) 0.0491(14) -0.0055(10) 0.0132(11) -0.0013(9) C25 0.0283(10) 0.0255(10) 0.0277(10) 0.0057(8) 0.0015(8) -0.0006(8) C26 0.0285(9) 0.0184(8) 0.0195(8) 0.0020(6) 0.0063(7) 0.0020(7) _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 C1 1.7425(16) . ? Cl1' C1' 1.7435(17) . ? O1 C9 1.4283(18) . ? O1 H1 0.78(2) . ? O1' C9' 1.4241(18) . ? O1' H1' 0.82(2) . ? C1 C2 1.377(2) . ? C1 C11 1.411(2) . ? N1 C23 1.496(2) . ? N1 C20 1.496(2) . ? N1 C21 1.506(2) . ? N1 H111 0.81(2) . ? C1' C2' 1.375(2) . ? C1' C11' 1.414(2) . ? O2 C26 1.2489(19) . ? C2 C3 1.386(2) . ? C2 H2 0.910(19) . ? C2' C3' 1.381(3) . ? C2' H2' 0.936(19) . ? O3 C26 1.2723(19) . ? C3 C4 1.371(2) . ? C3 H3A 0.93(2) . ? C3' C4' 1.381(2) . ? C3' H3' 0.898(19) . ? C4 C12 1.395(2) . ? C4 H4 0.985(18) . ? C4' C12' 1.400(2) . ? C4' H4' 0.958(17) . ? C9 C15 1.487(2) . ? C9 C11 1.524(2) . ? C9 C12 1.529(2) 3_657 ? C9' C15' 1.488(2) . ? C9' C11' 1.521(2) . ? C9' C12' 1.538(2) 3_666 ? C11 C12 1.388(2) . ? C11' C12' 1.389(2) . ? C12 C9 1.529(2) 3_657 ? C12' C9' 1.538(2) 3_666 ? C15 C16 1.180(2) . ? C15' C16' 1.184(3) . ? C16 H16 0.92(2) . ? C16' H16' 0.98(3) . ? C19 C20 1.498(3) . ? C19 H19C 1.01(2) . ? C19 H19B 0.92(3) . ? C19 H19A 0.98(2) . ? C20 H2OC 1.00(2) . ? C20 H20A 0.99(2) . ? C21 C22 1.512(3) . ? C21 H21B 0.96(2) . ? C21 H21A 1.001(19) . ? C22 H22C 0.99(2) . ? C22 H22B 1.03(3) . ? C22 H22A 0.98(2) . ? C23 C24 1.513(3) . ? C23 H23A 0.96(2) . ? C23 H23B 0.99(2) . ? C24 H24B 0.91(2) . ? C24 H24A 0.97(2) . ? C24 H24C 0.97(2) . ? C25 C26 1.504(3) . ? C25 H25C 1.01(5) . ? C25 H25B 0.94(5) . ? C25 H25A 1.02(4) . ? C25 H25F 1.00(4) . ? C25 H25E 0.97(5) . ? C25 H25D 0.89(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 H1 103.7(17) . . ? C9' O1' H1' 114.8(16) . . ? C2 C1 C11 122.14(15) . . ? C2 C1 Cl1 116.74(13) . . ? C11 C1 Cl1 121.10(12) . . ? C23 N1 C20 112.90(16) . . ? C23 N1 C21 111.43(14) . . ? C20 N1 C21 113.58(14) . . ? C23 N1 H111 107.8(14) . . ? C20 N1 H111 105.5(14) . . ? C21 N1 H111 105.0(14) . . ? C2' C1' C11' 122.12(15) . . ? C2' C1' Cl1' 115.91(13) . . ? C11' C1' Cl1' 121.97(12) . . ? C1 C2 C3 119.69(16) . . ? C1 C2 H2 119.8(12) . . ? C3 C2 H2 120.5(12) . . ? C1' C2' C3' 120.01(16) . . ? C1' C2' H2' 117.3(12) . . ? C3' C2' H2' 122.6(12) . . ? C4 C3 C2 119.43(16) . . ? C4 C3 H3A 117.3(12) . . ? C2 C3 H3A 123.3(12) . . ? C2' C3' C4' 119.32(16) . . ? C2' C3' H3' 121.2(12) . . ? C4' C3' H3' 119.4(12) . . ? C3 C4 C12 121.03(16) . . ? C3 C4 H4 118.6(11) . . ? C12 C4 H4 120.4(11) . . ? C3' C4' C12' 120.88(16) . . ? C3' C4' H4' 122.1(10) . . ? C12' C4' H4' 117.0(10) . . ? O1 C9 C15 108.29(12) . . ? O1 C9 C11 110.43(12) . . ? C15 C9 C11 109.43(12) . . ? O1 C9 C12 108.54(12) . 3_657 ? C15 C9 C12 105.99(12) . 3_657 ? C11 C9 C12 113.93(12) . 3_657 ? O1' C9' C15' 111.12(13) . . ? O1' C9' C11' 107.43(13) . . ? C15' C9' C11' 109.31(13) . . ? O1' C9' C12' 108.75(12) . 3_666 ? C15' C9' C12' 106.96(13) . 3_666 ? C11' C9' C12' 113.32(12) . 3_666 ? C12 C11 C1 116.79(14) . . ? C12 C11 C9 121.89(13) . . ? C1 C11 C9 121.31(13) . . ? C12' C11' C1' 116.96(14) . . ? C12' C11' C9' 122.51(13) . . ? C1' C11' C9' 120.52(14) . . ? C11 C12 C4 120.88(14) . . ? C11 C12 C9 124.17(14) . 3_657 ? C4 C12 C9 114.93(13) . 3_657 ? C11' C12' C4' 120.67(15) . . ? C11' C12' C9' 124.17(13) . 3_666 ? C4' C12' C9' 115.15(14) . 3_666 ? C16 C15 C9 172.50(17) . . ? C16' C15' C9' 177.41(18) . . ? C15 C16 H16 178.1(15) . . ? C15' C16' H16' 178.8(15) . . ? C20 C19 H19C 112.6(12) . . ? C20 C19 H19B 111.7(16) . . ? H19C C19 H19B 105(2) . . ? C20 C19 H19A 109.0(13) . . ? H19C C19 H19A 113.6(18) . . ? H19B C19 H19A 105(2) . . ? N1 C20 C19 112.97(18) . . ? N1 C20 H2OC 107.9(11) . . ? C19 C20 H2OC 112.1(11) . . ? N1 C20 H20A 105.8(12) . . ? C19 C20 H20A 111.3(12) . . ? H2OC C20 H20A 106.4(16) . . ? N1 C21 C22 114.33(17) . . ? N1 C21 H21B 104.4(11) . . ? C22 C21 H21B 109.7(11) . . ? N1 C21 H21A 109.3(11) . . ? C22 C21 H21A 107.7(11) . . ? H21B C21 H21A 111.4(16) . . ? C21 C22 H22C 108.1(14) . . ? C21 C22 H22B 111.8(15) . . ? H22C C22 H22B 108(2) . . ? C21 C22 H22A 104.0(13) . . ? H22C C22 H22A 112.5(19) . . ? H22B C22 H22A 112(2) . . ? N1 C23 C24 112.30(16) . . ? N1 C23 H23A 105.6(11) . . ? C24 C23 H23A 110.3(11) . . ? N1 C23 H23B 108.5(11) . . ? C24 C23 H23B 113.7(12) . . ? H23A C23 H23B 105.8(16) . . ? C23 C24 H24B 106.7(14) . . ? C23 C24 H24A 109.7(13) . . ? H24B C24 H24A 113.6(19) . . ? C23 C24 H24C 108.6(12) . . ? H24B C24 H24C 109.5(19) . . ? H24A C24 H24C 108.6(18) . . ? C26 C25 H25C 118(3) . . ? C26 C25 H25B 108(3) . . ? H25C C25 H25B 52(3) . . ? C26 C25 H25A 107(2) . . ? H25C C25 H25A 94(4) . . ? H25B C25 H25A 140(4) . . ? C26 C25 H25F 112.4(19) . . ? H25C C25 H25F 103(3) . . ? H25B C25 H25F 60(3) . . ? H25A C25 H25F 122(3) . . ? C26 C25 H25E 116(3) . . ? H25C C25 H25E 48(3) . . ? H25B C25 H25E 99(4) . . ? H25A C25 H25E 47(3) . . ? H25F C25 H25E 132(3) . . ? C26 C25 H25D 114(2) . . ? H25C C25 H25D 128(3) . . ? H25B C25 H25D 113(4) . . ? H25A C25 H25D 69(3) . . ? H25F C25 H25D 56(3) . . ? H25E C25 H25D 107(4) . . ? O2 C26 O3 122.42(16) . . ? O2 C26 C25 119.24(15) . . ? O3 C26 C25 118.34(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.425 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.066 # Attachment 'Complex_2.cif' data_03rmd137 _database_code_depnum_ccdc_archive 'CCDC 669316' #TrackingRef 'Complex_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,5-dichloro-trans-9,10-diethynyl-9,10-dihydroxy-9,10- dihydroanthracene ; _chemical_name_common ;1,5-dichloro-trans-9,10-diethynyl-9,10-dihydroxy-9,10- dihydroanthracene ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H29 Cl2 N O4' _chemical_formula_weight 490.40 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' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.4892(4) _cell_length_b 13.3457(7) _cell_length_c 24.0116(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.709(2) _cell_angle_gamma 90.00 _cell_volume 2399.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1682 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 26.98 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 6K CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17105 _diffrn_reflns_av_R_equivalents 0.0747 _diffrn_reflns_av_sigmaI/netI 0.1197 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5514 _reflns_number_gt 2757 _reflns_threshold_expression I>2\s(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^)+(0.0387P)^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 5514 _refine_ls_number_parameters 366 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1097 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 0.828 _refine_ls_restrained_S_all 0.828 _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 0.04827(8) 0.89422(5) 0.19921(3) 0.02715(18) Uani 1 1 d . . . O1 O 0.0169(2) 0.81046(14) 0.31597(8) 0.0196(4) Uani 1 1 d . . . H1 H 0.052(3) 0.8578(18) 0.3351(11) 0.019(8) Uiso 1 1 d . . . C1 C 0.2646(3) 0.8886(2) 0.22724(11) 0.0204(6) Uani 1 1 d . . . N1 N 0.3843(4) 1.1856(2) 0.40350(11) 0.0412(7) Uani 1 1 d . . . H111 H 0.307(4) 1.120(2) 0.4131(13) 0.058(10) Uiso 1 1 d . . . Cl2 Cl 0.67327(8) 0.61094(5) 0.43328(3) 0.02774(18) Uani 1 1 d . . . O2 O 0.6959(2) 0.70357(14) 0.32227(8) 0.0226(5) Uani 1 1 d . . . H2 H 0.775(4) 0.740(2) 0.3190(13) 0.040(10) Uiso 1 1 d . . . C2 C 0.3879(4) 0.9507(2) 0.20344(12) 0.0245(7) Uani 1 1 d . . . H2A H 0.354(3) 0.9926(18) 0.1740(11) 0.026(8) Uiso 1 1 d . . . C3 C 0.5622(4) 0.9501(2) 0.22356(13) 0.0266(7) Uani 1 1 d . . . H3 H 0.644(3) 0.9896(18) 0.2078(11) 0.022(7) Uiso 1 1 d . . . O3 O 0.2273(3) 1.03426(16) 0.45096(9) 0.0478(6) Uani 1 1 d . . . C4 C 0.6078(3) 0.8894(2) 0.26770(12) 0.0221(6) Uani 1 1 d . . . H4 H 0.728(3) 0.8909(17) 0.2810(10) 0.013(6) Uiso 1 1 d . . . O4 O 0.1235(2) 0.96695(14) 0.37227(8) 0.0296(5) Uani 1 1 d . . . C5 C 0.4560(3) 0.6218(2) 0.40659(11) 0.0206(6) Uani 1 1 d . . . C6 C 0.3320(4) 0.5601(2) 0.43029(12) 0.0257(7) Uani 1 1 d . . . H6 H 0.357(3) 0.5163(19) 0.4582(11) 0.029(8) Uiso 1 1 d . . . C7 C 0.1556(4) 0.5622(2) 0.41093(13) 0.0270(7) Uani 1 1 d . . . H7 H 0.068(3) 0.5174(17) 0.4274(10) 0.016(7) Uiso 1 1 d . . . C8 C 0.1107(3) 0.6252(2) 0.36830(12) 0.0222(6) Uani 1 1 d . . . H8 H -0.011(3) 0.6279(17) 0.3545(11) 0.023(7) Uiso 1 1 d . . . C9 C 0.1663(3) 0.75464(18) 0.29659(11) 0.0157(6) Uani 1 1 d . . . C10 C 0.5500(3) 0.76262(19) 0.34084(11) 0.0190(6) Uani 1 1 d . . . C11 C 0.2366(3) 0.68866(18) 0.34427(11) 0.0167(6) Uani 1 1 d . . . C12 C 0.4125(3) 0.68922(18) 0.36362(11) 0.0166(6) Uani 1 1 d . . . C13 C 0.3062(3) 0.82436(18) 0.27202(10) 0.0169(6) Uani 1 1 d . . . C14 C 0.4816(3) 0.82686(18) 0.29247(11) 0.0176(6) Uani 1 1 d . . . C15 C 0.1003(3) 0.6848(2) 0.25286(11) 0.0202(6) Uani 1 1 d . . . C16 C 0.0523(4) 0.6231(2) 0.22060(13) 0.0282(7) Uani 1 1 d . . . H16 H 0.014(4) 0.576(2) 0.1949(13) 0.043(9) Uiso 1 1 d . . . C17 C 0.6056(3) 0.8304(2) 0.38727(12) 0.0218(6) Uani 1 1 d . . . C18 C 0.6485(4) 0.8829(2) 0.42451(14) 0.0320(7) Uani 1 1 d . . . H18 H 0.680(4) 0.923(2) 0.4523(12) 0.045(10) Uiso 1 1 d . . . C19 C 0.1582(4) 0.9626(2) 0.42343(12) 0.0307(7) Uani 1 1 d . . . C20 C 0.1218(4) 0.8687(2) 0.45518(13) 0.0389(8) Uani 1 1 d . . . H20A H 0.0699 0.8196 0.4306 0.058 Uiso 1 1 calc R . . H20B H 0.0404 0.8829 0.4847 0.058 Uiso 1 1 calc R . . H20C H 0.2316 0.8432 0.4706 0.058 Uiso 1 1 calc R . . C21 C 0.5709(6) 1.1453(4) 0.4181(2) 0.0624(16) Uani 0.70 1 d P A 1 H21A H 0.5767 1.1285 0.4574 0.075 Uiso 0.70 1 calc PR A 1 H21B H 0.5928 1.0846 0.3970 0.075 Uiso 0.70 1 calc PR A 1 C21' C 0.5124(11) 1.2252(7) 0.4464(4) 0.020(2) Uiso 0.30 1 d P A 2 H21C H 0.5994 1.1731 0.4543 0.024 Uiso 0.30 1 calc PR A 2 H21D H 0.4465 1.2365 0.4803 0.024 Uiso 0.30 1 calc PR A 2 C22 C 0.7134(8) 1.2220(6) 0.4051(3) 0.109(3) Uani 0.70 1 d P A 1 H22A H 0.8287 1.1952 0.4147 0.163 Uiso 0.70 1 calc PR A 1 H22B H 0.6926 1.2817 0.4263 0.163 Uiso 0.70 1 calc PR A 1 H22C H 0.7092 1.2376 0.3661 0.163 Uiso 0.70 1 calc PR A 1 C22' C 0.6126(11) 1.3195(6) 0.4334(4) 0.024(2) Uiso 0.30 1 d P A 2 H22D H 0.6874 1.3372 0.4647 0.036 Uiso 0.30 1 calc PR A 2 H22E H 0.5293 1.3727 0.4261 0.036 Uiso 0.30 1 calc PR A 2 H22F H 0.6851 1.3090 0.4013 0.036 Uiso 0.30 1 calc PR A 2 C23 C 0.3522(7) 1.2024(3) 0.34625(18) 0.0414(12) Uani 0.70 1 d P A 1 H23A H 0.4118 1.2641 0.3360 0.050 Uiso 0.70 1 calc PR A 1 H23B H 0.2250 1.2129 0.3408 0.050 Uiso 0.70 1 calc PR A 1 C23' C 0.4890(16) 1.1682(9) 0.3474(5) 0.047(3) Uiso 0.30 1 d P A 2 H23C H 0.4046 1.1553 0.3173 0.057 Uiso 0.30 1 calc PR A 2 H23D H 0.5558 1.2282 0.3382 0.057 Uiso 0.30 1 calc PR A 2 C24 C 0.4106(5) 1.1214(3) 0.30640(17) 0.0289(10) Uani 0.70 1 d P A 1 H24A H 0.3819 1.1411 0.2689 0.043 Uiso 0.70 1 calc PR A 1 H24B H 0.3499 1.0600 0.3149 0.043 Uiso 0.70 1 calc PR A 1 H24C H 0.5372 1.1115 0.3101 0.043 Uiso 0.70 1 calc PR A 1 C24' C 0.5884(19) 1.0994(11) 0.3520(7) 0.092(5) Uiso 0.30 1 d P A 2 H24D H 0.6518 1.0903 0.3179 0.138 Uiso 0.30 1 calc PR A 2 H24E H 0.5218 1.0398 0.3602 0.138 Uiso 0.30 1 calc PR A 2 H24F H 0.6720 1.1123 0.3818 0.138 Uiso 0.30 1 calc PR A 2 C25 C 0.3413(9) 1.2632(4) 0.4430(2) 0.0739(18) Uani 0.70 1 d P A 1 H25A H 0.4120 1.3223 0.4353 0.089 Uiso 0.70 1 calc PR A 1 H25B H 0.3721 1.2405 0.4803 0.089 Uiso 0.70 1 calc PR A 1 C25' C 0.2429(12) 1.2692(7) 0.3855(4) 0.032(2) Uiso 0.30 1 d P A 2 H25C H 0.3002 1.3342 0.3828 0.039 Uiso 0.30 1 calc PR A 2 H25D H 0.1890 1.2530 0.3497 0.039 Uiso 0.30 1 calc PR A 2 C26 C 0.1455(10) 1.2903(6) 0.4406(3) 0.0442(15) Uani 0.70 1 d P A 1 H26A H 0.1218 1.3418 0.4675 0.066 Uiso 0.70 1 calc PR A 1 H26B H 0.0752 1.2322 0.4489 0.066 Uiso 0.70 1 calc PR A 1 H26C H 0.1151 1.3142 0.4040 0.066 Uiso 0.70 1 calc PR A 1 C26' C 0.100(4) 1.270(2) 0.4315(12) 0.129(14) Uiso 0.30 1 d P A 2 H26D H 0.0105 1.3190 0.4227 0.193 Uiso 0.30 1 calc PR A 2 H26E H 0.1557 1.2864 0.4666 0.193 Uiso 0.30 1 calc PR A 2 H26F H 0.0459 1.2050 0.4339 0.193 Uiso 0.30 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0210(3) 0.0310(4) 0.0293(4) 0.0063(3) -0.0074(3) 0.0017(3) O1 0.0124(9) 0.0208(10) 0.0256(11) -0.0055(9) 0.0000(8) -0.0006(8) C1 0.0170(12) 0.0214(14) 0.0227(15) -0.0013(13) -0.0011(11) 0.0017(12) N1 0.0501(17) 0.0434(17) 0.0301(16) -0.0091(14) -0.0050(14) -0.0077(15) Cl2 0.0200(4) 0.0374(4) 0.0258(4) 0.0070(4) -0.0054(3) 0.0011(3) O2 0.0145(10) 0.0234(11) 0.0301(12) 0.0014(9) 0.0049(9) 0.0022(9) C2 0.0255(15) 0.0242(16) 0.0238(17) 0.0082(14) 0.0005(13) 0.0038(13) C3 0.0217(15) 0.0244(16) 0.0340(19) 0.0069(14) 0.0066(14) -0.0053(13) O3 0.0664(15) 0.0459(14) 0.0309(13) -0.0129(12) -0.0024(12) -0.0170(12) C4 0.0146(13) 0.0231(15) 0.0285(16) 0.0020(14) 0.0014(12) 0.0000(12) O4 0.0361(11) 0.0292(11) 0.0234(11) -0.0019(10) -0.0027(9) -0.0015(9) C5 0.0166(13) 0.0257(15) 0.0192(15) -0.0027(13) -0.0028(11) 0.0030(12) C6 0.0257(15) 0.0280(16) 0.0236(17) 0.0074(14) -0.0003(14) 0.0027(13) C7 0.0213(14) 0.0287(16) 0.0309(17) 0.0072(14) 0.0041(14) -0.0035(13) C8 0.0143(13) 0.0231(16) 0.0291(17) 0.0024(13) -0.0002(12) -0.0020(12) C9 0.0115(12) 0.0172(13) 0.0182(15) -0.0011(12) -0.0015(11) 0.0015(10) C10 0.0123(12) 0.0207(14) 0.0240(16) -0.0019(12) 0.0019(11) 0.0009(11) C11 0.0176(13) 0.0150(13) 0.0174(15) -0.0018(12) 0.0016(11) 0.0008(11) C12 0.0150(12) 0.0156(13) 0.0191(15) -0.0040(12) 0.0014(11) 0.0000(11) C13 0.0179(13) 0.0162(13) 0.0166(14) -0.0036(12) 0.0001(11) 0.0018(11) C14 0.0178(13) 0.0164(14) 0.0186(15) -0.0023(12) 0.0015(12) 0.0007(11) C15 0.0141(13) 0.0218(15) 0.0247(16) 0.0022(13) -0.0009(12) -0.0012(11) C16 0.0296(15) 0.0275(17) 0.0274(17) -0.0015(15) -0.0040(13) -0.0046(14) C17 0.0153(13) 0.0250(15) 0.0252(16) -0.0010(13) -0.0014(12) -0.0022(11) C18 0.0314(16) 0.0346(18) 0.0297(19) -0.0044(16) -0.0046(15) -0.0042(15) C19 0.0278(16) 0.0349(18) 0.0293(19) -0.0042(15) -0.0013(14) 0.0051(14) C20 0.0421(18) 0.047(2) 0.0271(17) -0.0011(16) -0.0028(15) 0.0041(16) C21 0.052(3) 0.074(4) 0.061(4) 0.019(3) -0.018(3) -0.006(3) C22 0.060(4) 0.174(8) 0.090(5) 0.053(5) -0.025(4) -0.054(5) C23 0.059(3) 0.037(3) 0.028(3) 0.005(2) -0.014(2) -0.012(2) C24 0.037(2) 0.027(2) 0.024(2) 0.000(2) -0.0012(19) -0.0069(19) C25 0.128(6) 0.047(3) 0.047(4) -0.004(3) -0.005(4) -0.006(4) C26 0.047(3) 0.048(3) 0.037(4) -0.005(3) -0.002(3) 0.005(3) _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 C1 1.748(2) . ? O1 C9 1.427(3) . ? O1 H1 0.82(2) . ? C1 C2 1.372(4) . ? C1 C13 1.407(3) . ? N1 C23 1.410(5) . ? N1 C25 1.444(6) . ? N1 C21' 1.495(9) . ? N1 C21 1.534(5) . ? N1 C23' 1.584(12) . ? N1 C25' 1.595(9) . ? N1 H111 1.07(3) . ? Cl2 C5 1.747(2) . ? O2 C10 1.423(3) . ? O2 H2 0.77(3) . ? C2 C3 1.386(4) . ? C2 H2A 0.93(3) . ? C3 C4 1.374(4) . ? C3 H3 0.90(2) . ? O3 C19 1.269(3) . ? C4 C14 1.399(3) . ? C4 H4 0.95(2) . ? O4 C19 1.254(3) . ? C5 C6 1.371(4) . ? C5 C12 1.404(3) . ? C6 C7 1.395(4) . ? C6 H6 0.91(3) . ? C7 C8 1.364(4) . ? C7 H7 0.98(2) . ? C8 C11 1.397(3) . ? C8 H8 0.97(2) . ? C9 C15 1.484(3) . ? C9 C13 1.526(3) . ? C9 C11 1.532(3) . ? C10 C17 1.491(4) . ? C10 C14 1.527(3) . ? C10 C12 1.528(3) . ? C11 C12 1.392(3) . ? C13 C14 1.397(3) . ? C15 C16 1.184(4) . ? C16 H16 0.92(3) . ? C17 C18 1.178(4) . ? C18 H18 0.88(3) . ? C19 C20 1.494(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.514(7) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21' C22' 1.500(11) . ? C21' H21C 0.9700 . ? C21' H21D 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C22' H22D 0.9600 . ? C22' H22E 0.9600 . ? C22' H22F 0.9600 . ? C23 C24 1.512(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23' C24' 1.187(16) . ? C23' H23C 0.9700 . ? C23' H23D 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C24' H24D 0.9600 . ? C24' H24E 0.9600 . ? C24' H24F 0.9600 . ? C25 C26 1.511(9) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C25' C26' 1.55(3) . ? C25' H25C 0.9700 . ? C25' H25D 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C26' H26D 0.9600 . ? C26' H26E 0.9600 . ? C26' H26F 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 C9 O1 H1 109.9(17) . . ? C2 C1 C13 122.9(2) . . ? C2 C1 Cl1 116.1(2) . . ? C13 C1 Cl1 121.08(19) . . ? C23 N1 C25 119.3(4) . . ? C23 N1 C21' 135.6(4) . . ? C25 N1 C21' 55.9(4) . . ? C23 N1 C21 115.0(4) . . ? C25 N1 C21 108.1(4) . . ? C21' N1 C21 52.5(4) . . ? C23 N1 C23' 43.5(4) . . ? C25 N1 C23' 141.3(6) . . ? C21' N1 C23' 108.5(6) . . ? C21 N1 C23' 71.6(5) . . ? C23 N1 C25' 61.3(4) . . ? C25 N1 C25' 61.6(4) . . ? C21' N1 C25' 110.9(5) . . ? C21 N1 C25' 155.1(5) . . ? C23' N1 C25' 101.8(6) . . ? C23 N1 H111 104.7(17) . . ? C25 N1 H111 108.5(17) . . ? C21' N1 H111 118.8(18) . . ? C21 N1 H111 99.0(16) . . ? C23' N1 H111 109.7(18) . . ? C25' N1 H111 105.8(17) . . ? C10 O2 H2 106(2) . . ? C1 C2 C3 119.2(3) . . ? C1 C2 H2A 119.9(15) . . ? C3 C2 H2A 120.9(15) . . ? C4 C3 C2 119.7(3) . . ? C4 C3 H3 120.5(16) . . ? C2 C3 H3 119.8(16) . . ? C3 C4 C14 121.2(2) . . ? C3 C4 H4 118.0(14) . . ? C14 C4 H4 120.8(14) . . ? C6 C5 C12 122.5(2) . . ? C6 C5 Cl2 115.5(2) . . ? C12 C5 Cl2 122.0(2) . . ? C5 C6 C7 119.6(3) . . ? C5 C6 H6 124.1(16) . . ? C7 C6 H6 116.3(16) . . ? C8 C7 C6 119.1(3) . . ? C8 C7 H7 121.4(13) . . ? C6 C7 H7 119.5(13) . . ? C7 C8 C11 121.5(2) . . ? C7 C8 H8 120.1(15) . . ? C11 C8 H8 118.3(15) . . ? O1 C9 C15 107.63(19) . . ? O1 C9 C13 110.7(2) . . ? C15 C9 C13 109.5(2) . . ? O1 C9 C11 108.7(2) . . ? C15 C9 C11 106.0(2) . . ? C13 C9 C11 114.1(2) . . ? O2 C10 C17 111.2(2) . . ? O2 C10 C14 108.9(2) . . ? C17 C10 C14 108.4(2) . . ? O2 C10 C12 106.3(2) . . ? C17 C10 C12 107.7(2) . . ? C14 C10 C12 114.3(2) . . ? C12 C11 C8 120.4(2) . . ? C12 C11 C9 124.2(2) . . ? C8 C11 C9 115.4(2) . . ? C11 C12 C5 116.9(2) . . ? C11 C12 C10 121.6(2) . . ? C5 C12 C10 121.5(2) . . ? C14 C13 C1 116.9(2) . . ? C14 C13 C9 121.7(2) . . ? C1 C13 C9 121.3(2) . . ? C13 C14 C4 120.1(2) . . ? C13 C14 C10 124.0(2) . . ? C4 C14 C10 115.9(2) . . ? C16 C15 C9 174.8(3) . . ? C15 C16 H16 178.7(19) . . ? C18 C17 C10 179.0(3) . . ? C17 C18 H18 179(2) . . ? O4 C19 O3 123.6(3) . . ? O4 C19 C20 120.1(3) . . ? O3 C19 C20 116.2(3) . . ? 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 . . ? C22 C21 N1 111.0(4) . . ? C22 C21 H21A 109.4 . . ? N1 C21 H21A 109.4 . . ? C22 C21 H21B 109.4 . . ? N1 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? N1 C21' C22' 118.2(7) . . ? N1 C21' H21C 107.8 . . ? C22' C21' H21C 107.8 . . ? N1 C21' H21D 107.8 . . ? C22' C21' H21D 107.8 . . ? H21C C21' H21D 107.1 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21' C22' H22D 109.5 . . ? C21' C22' H22E 109.5 . . ? H22D C22' H22E 109.5 . . ? C21' C22' H22F 109.5 . . ? H22D C22' H22F 109.5 . . ? H22E C22' H22F 109.5 . . ? N1 C23 C24 117.1(4) . . ? N1 C23 H23A 108.0 . . ? C24 C23 H23A 108.0 . . ? N1 C23 H23B 108.0 . . ? C24 C23 H23B 108.0 . . ? H23A C23 H23B 107.3 . . ? C24' C23' N1 110.5(12) . . ? C24' C23' H23C 109.6 . . ? N1 C23' H23C 109.6 . . ? C24' C23' H23D 109.6 . . ? N1 C23' H23D 109.6 . . ? H23C C23' H23D 108.1 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23' C24' H24D 109.5 . . ? C23' C24' H24E 109.5 . . ? H24D C24' H24E 109.5 . . ? C23' C24' H24F 109.5 . . ? H24D C24' H24F 109.5 . . ? H24E C24' H24F 109.5 . . ? N1 C25 C26 111.8(5) . . ? N1 C25 H25A 109.3 . . ? C26 C25 H25A 109.3 . . ? N1 C25 H25B 109.3 . . ? C26 C25 H25B 109.3 . . ? H25A C25 H25B 107.9 . . ? C26' C25' N1 105.8(13) . . ? C26' C25' H25C 110.6 . . ? N1 C25' H25C 110.6 . . ? C26' C25' H25D 110.6 . . ? N1 C25' H25D 110.6 . . ? H25C C25' H25D 108.7 . . ? 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' C26' H26D 109.5 . . ? C25' C26' H26E 109.5 . . ? H26D C26' H26E 109.5 . . ? C25' C26' H26F 109.5 . . ? H26D C26' H26F 109.5 . . ? H26E C26' H26F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.451 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.064 # Attachment 'Complex_3.cif' ############################################################# # ***durham university chemical crystallography group*** # # this structure was solved by raju mondal on 17/11/2003 ############################################################# data_03rmd132 _database_code_depnum_ccdc_archive 'CCDC 762165' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H25 Cl2 N O3' _chemical_formula_weight 446.35 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.2741(2) _cell_length_b 15.3177(3) _cell_length_c 15.8154(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.0250(10) _cell_angle_gamma 90.00 _cell_volume 2246.34(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7029 _cell_measurement_theta_min 2.526 _cell_measurement_theta_max 27.275 _exptl_crystal_description Cube _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.314 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'smart 6k CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 34371 _diffrn_reflns_av_R_equivalents 0.0650 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5157 _reflns_number_gt 3770 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0533P)^2^+0.4140P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5157 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1086 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.49660(5) 0.95399(4) 0.15070(3) 0.03080(14) Uani 0.90 1 d P . . O1 O 0.68659(14) 0.81522(9) 0.23977(7) 0.0253(3) Uani 1 1 d . . . H1 H 0.773(3) 0.8276(15) 0.2417(14) 0.042(7) Uiso 1 1 d . . . N1 N 1.06851(15) 0.85086(10) 0.30861(9) 0.0246(3) Uani 1 1 d . . . C1 C 0.6457(2) 0.93140(13) 0.08736(12) 0.0288(4) Uani 1 1 d . . . Cl1' Cl 1.0483(7) 0.8940(4) -0.0815(4) 0.0555(15) Uiso 0.10 1 d P . 2 Cl2 Cl 1.11205(6) 0.58403(4) 0.06199(4) 0.03883(16) Uani 0.90 1 d P . . O2 O 1.06708(12) 0.78966(9) 0.09536(8) 0.0276(3) Uani 1 1 d . . . H2 H 1.035(3) 0.8101(17) 0.1428(16) 0.053(7) Uiso 1 1 d . . . C2 C 0.6877(2) 0.99630(15) 0.03355(14) 0.0384(5) Uani 1 1 d . . . H2A H 0.635(3) 1.0520(18) 0.0323(17) 0.062(8) Uiso 1 1 d . . . Cl2' Cl 0.5576(7) 0.6505(4) 0.2732(4) 0.0503(14) Uiso 0.10 1 d P . 2 C3 C 0.8049(2) 0.98215(16) -0.01772(14) 0.0401(5) Uani 1 1 d . . . H3 H 0.834(2) 1.0223(15) -0.0514(15) 0.040(6) Uiso 1 1 d . . . O3 O 0.96844(13) 0.84946(9) 0.24185(8) 0.0285(3) Uani 1 1 d . . . C4 C 0.8788(2) 0.90455(15) -0.01274(13) 0.0346(5) Uani 1 1 d . . . H4 H 0.947(2) 0.8968(14) -0.0419(14) 0.033(6) Uiso 1 1 d . . . C5 C 0.9459(2) 0.60307(13) 0.10983(13) 0.0312(4) Uani 1 1 d . . . C6 C 0.8919(2) 0.53573(14) 0.15700(15) 0.0373(5) Uani 1 1 d . . . H6 H 0.939(3) 0.4852(18) 0.1616(16) 0.055(7) Uiso 1 1 d . . . C7 C 0.7679(2) 0.54736(14) 0.20288(14) 0.0359(5) Uani 1 1 d . . . H7 H 0.733(2) 0.5023(16) 0.2373(15) 0.045(6) Uiso 1 1 d . . . C8 C 0.6991(2) 0.62693(13) 0.20008(13) 0.0287(4) Uani 1 1 d . . . H8 H 0.625(3) 0.6351(16) 0.2331(16) 0.047(7) Uiso 1 1 d . . . C9 C 0.66941(17) 0.78194(12) 0.15576(10) 0.0208(4) Uani 1 1 d . . . C10 C 0.93841(17) 0.75972(13) 0.05296(11) 0.0233(4) Uani 1 1 d . . . C11 C 0.75057(17) 0.69533(12) 0.15035(10) 0.0214(4) Uani 1 1 d . . . C12 C 0.87518(18) 0.68445(12) 0.10317(11) 0.0227(4) Uani 1 1 d . . . C13 C 0.71770(17) 0.85064(12) 0.09301(10) 0.0219(4) Uani 1 1 d . . . C14 C 0.83783(18) 0.83864(12) 0.04272(11) 0.0231(4) Uani 1 1 d . . . C15 C 0.51415(19) 0.76214(13) 0.13975(11) 0.0274(4) Uani 1 1 d . . . C16 C 0.3933(2) 0.74414(15) 0.12114(14) 0.0376(5) Uani 1 1 d . . . H16 H 0.294(3) 0.7432(16) 0.1053(15) 0.054(7) Uiso 1 1 d . . . C17 C 0.97866(19) 0.73059(14) -0.03281(12) 0.0304(4) Uani 1 1 d . . . C18 C 1.0091(2) 0.71319(18) -0.10264(14) 0.0446(6) Uani 1 1 d . . . H18 H 1.042(3) 0.6975(18) -0.1568(17) 0.063(8) Uiso 1 1 d . . . C19 C 1.0138(3) 0.69638(17) 0.3542(2) 0.0512(7) Uani 1 1 d . . . H19C H 0.935(3) 0.6934(18) 0.3188(18) 0.066(8) Uiso 1 1 d . . . H19B H 0.981(3) 0.7124(19) 0.4110(19) 0.068(9) Uiso 1 1 d . . . H19A H 1.067(3) 0.637(2) 0.3520(17) 0.071(9) Uiso 1 1 d . . . C20 C 1.1251(2) 0.75961(14) 0.32345(16) 0.0384(5) Uani 1 1 d . . . H20B H 1.208(2) 0.7602(15) 0.3614(15) 0.043(6) Uiso 1 1 d . . . H20A H 1.168(3) 0.7433(16) 0.2667(16) 0.053(7) Uiso 1 1 d . . . C21 C 1.0876(3) 0.89273(17) 0.46354(14) 0.0405(5) Uani 1 1 d . . . H21C H 1.171(3) 0.9373(15) 0.4564(14) 0.046(6) Uiso 1 1 d . . . H21B H 1.027(3) 0.9136(15) 0.5069(16) 0.045(7) Uiso 1 1 d . . . H21A H 1.127(3) 0.8361(17) 0.4823(15) 0.049(7) Uiso 1 1 d . . . C22 C 0.9933(2) 0.88688(14) 0.38450(12) 0.0291(4) Uani 1 1 d . . . H22B H 0.906(2) 0.8481(14) 0.3936(12) 0.030(5) Uiso 1 1 d . . . H22A H 0.956(2) 0.9455(15) 0.3695(13) 0.037(6) Uiso 1 1 d . . . C23 C 1.1512(3) 1.00002(16) 0.26161(16) 0.0409(5) Uani 1 1 d . . . H23C H 1.067(3) 0.9949(15) 0.2206(15) 0.047(7) Uiso 1 1 d . . . H23B H 1.123(2) 1.0352(16) 0.3118(15) 0.044(6) Uiso 1 1 d . . . H23A H 1.242(3) 1.0256(17) 0.2389(16) 0.060(8) Uiso 1 1 d . . . C24 C 1.1941(2) 0.90790(15) 0.28300(14) 0.0329(5) Uani 1 1 d . . . H24B H 1.259(2) 0.9053(12) 0.3262(13) 0.024(5) Uiso 1 1 d . . . H24A H 1.230(2) 0.8765(14) 0.2360(14) 0.036(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0244(2) 0.0320(3) 0.0362(3) -0.0031(2) 0.0063(2) 0.0079(2) O1 0.0203(6) 0.0381(8) 0.0175(6) -0.0054(5) 0.0024(5) -0.0028(6) N1 0.0202(7) 0.0305(9) 0.0230(7) -0.0046(6) -0.0043(6) -0.0011(6) C1 0.0238(9) 0.0346(11) 0.0280(10) -0.0009(8) 0.0007(7) 0.0050(8) Cl2 0.0245(3) 0.0441(3) 0.0478(3) -0.0124(3) -0.0016(2) 0.0139(2) O2 0.0143(6) 0.0438(8) 0.0248(7) -0.0041(6) -0.0002(5) -0.0019(5) C2 0.0367(11) 0.0361(12) 0.0424(12) 0.0103(10) -0.0003(9) 0.0064(10) C3 0.0392(12) 0.0422(13) 0.0389(12) 0.0183(10) 0.0026(10) 0.0004(10) O3 0.0206(6) 0.0435(8) 0.0211(6) -0.0047(6) -0.0045(5) -0.0043(6) C4 0.0256(10) 0.0508(14) 0.0275(10) 0.0076(9) 0.0064(8) -0.0001(9) C5 0.0242(9) 0.0353(11) 0.0340(11) -0.0085(9) -0.0036(8) 0.0053(8) C6 0.0375(11) 0.0273(11) 0.0466(13) -0.0044(10) -0.0095(10) 0.0063(9) C7 0.0364(11) 0.0308(11) 0.0401(12) 0.0056(10) -0.0100(9) -0.0078(9) C8 0.0230(9) 0.0343(11) 0.0286(10) 0.0002(8) -0.0021(8) -0.0056(8) C9 0.0158(8) 0.0305(10) 0.0162(8) -0.0040(7) 0.0009(6) 0.0009(7) C10 0.0132(8) 0.0374(11) 0.0193(8) -0.0032(8) 0.0011(6) 0.0009(7) C11 0.0163(8) 0.0284(10) 0.0194(8) -0.0031(7) -0.0035(6) -0.0024(7) C12 0.0191(8) 0.0292(10) 0.0197(8) -0.0060(7) -0.0051(7) 0.0018(7) C13 0.0184(8) 0.0293(10) 0.0180(8) -0.0024(7) -0.0023(6) 0.0005(7) C14 0.0190(8) 0.0318(10) 0.0185(8) -0.0009(7) -0.0011(6) -0.0011(7) C15 0.0202(9) 0.0378(11) 0.0245(9) -0.0057(8) 0.0049(7) 0.0024(8) C16 0.0191(9) 0.0521(14) 0.0416(12) -0.0108(10) 0.0005(8) 0.0018(9) C17 0.0179(8) 0.0461(12) 0.0274(10) -0.0038(9) 0.0036(7) 0.0018(8) C18 0.0309(11) 0.0744(18) 0.0287(11) -0.0097(11) 0.0085(9) 0.0008(11) C19 0.0593(16) 0.0332(13) 0.0606(18) 0.0012(12) -0.0179(14) -0.0067(12) C20 0.0379(11) 0.0328(12) 0.0441(13) -0.0044(10) -0.0098(10) 0.0058(9) C21 0.0521(14) 0.0455(14) 0.0237(11) -0.0017(10) -0.0061(10) -0.0070(12) C22 0.0304(10) 0.0349(11) 0.0221(9) -0.0009(8) 0.0000(8) -0.0014(9) C23 0.0385(12) 0.0420(13) 0.0423(13) 0.0017(11) 0.0053(11) -0.0091(10) C24 0.0199(9) 0.0450(13) 0.0337(11) -0.0049(10) -0.0010(8) -0.0057(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 C1 1.7564(19) . ? O1 C9 1.429(2) . ? O1 H1 0.83(2) . ? N1 O3 1.3934(18) . ? N1 C22 1.504(2) . ? N1 C20 1.510(3) . ? N1 C24 1.517(2) . ? C1 C2 1.370(3) . ? C1 C13 1.408(3) . ? Cl1' C4 1.935(7) . ? Cl1' Cl2' 2.400(9) 4_675 ? Cl1' H4 1.14(2) . ? Cl2 C5 1.7530(19) . ? O2 C10 1.434(2) . ? O2 H2 0.87(3) . ? C2 C3 1.385(3) . ? C2 H2A 0.98(3) . ? Cl2' C8 1.801(7) . ? Cl2' Cl1' 2.400(9) 4_576 ? Cl2' H8 0.93(3) . ? C3 C4 1.374(3) . ? C3 H3 0.86(2) . ? C4 C14 1.394(3) . ? C4 H4 0.80(2) . ? C5 C6 1.373(3) . ? C5 C12 1.412(3) . ? C6 C7 1.382(3) . ? C6 H6 0.89(3) . ? C7 C8 1.376(3) . ? C7 H7 0.94(2) . ? C8 C11 1.399(3) . ? C8 H8 0.88(3) . ? C9 C15 1.489(2) . ? C9 C13 1.520(2) . ? C9 C11 1.528(2) . ? C10 C17 1.482(2) . ? C10 C12 1.523(3) . ? C10 C14 1.534(2) . ? C11 C12 1.397(2) . ? C13 C14 1.392(2) . ? C15 C16 1.186(3) . ? C16 H16 0.95(2) . ? C17 C18 1.175(3) . ? C18 H18 0.95(3) . ? C19 C20 1.503(4) . ? C19 H19C 0.92(3) . ? C19 H19B 0.99(3) . ? C19 H19A 1.03(3) . ? C20 H20B 0.97(2) . ? C20 H20A 1.02(2) . ? C21 C22 1.515(3) . ? C21 H21C 1.04(2) . ? C21 H21B 0.95(2) . ? C21 H21A 0.98(3) . ? C22 H22B 1.02(2) . ? C22 H22A 0.99(2) . ? C23 C24 1.503(3) . ? C23 H23C 1.01(2) . ? C23 H23B 1.00(2) . ? C23 H23A 1.00(3) . ? C24 H24B 0.90(2) . ? C24 H24A 0.95(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 H1 102.0(16) . . ? O3 N1 C22 107.37(13) . . ? O3 N1 C20 109.18(14) . . ? C22 N1 C20 112.36(16) . . ? O3 N1 C24 108.11(14) . . ? C22 N1 C24 111.78(15) . . ? C20 N1 C24 107.94(15) . . ? C2 C1 C13 122.50(18) . . ? C2 C1 Cl1 116.55(16) . . ? C13 C1 Cl1 120.95(15) . . ? C4 Cl1' Cl2' 127.3(4) . 4_675 ? C4 Cl1' H4 2.8(11) . . ? Cl2' Cl1' H4 125.6(12) 4_675 . ? C10 O2 H2 103.0(17) . . ? C1 C2 C3 119.0(2) . . ? C1 C2 H2A 119.7(16) . . ? C3 C2 H2A 121.3(16) . . ? C8 Cl2' Cl1' 126.6(4) . 4_576 ? C8 Cl2' H8 4.8(15) . . ? Cl1' Cl2' H8 128.0(16) 4_576 . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 119.7(16) . . ? C2 C3 H3 120.5(16) . . ? C3 C4 C14 121.4(2) . . ? C3 C4 Cl1' 116.7(3) . . ? C14 C4 Cl1' 121.8(3) . . ? C3 C4 H4 119.7(16) . . ? C14 C4 H4 118.8(16) . . ? Cl1' C4 H4 4.0(16) . . ? C6 C5 C12 122.03(18) . . ? C6 C5 Cl2 116.20(16) . . ? C12 C5 Cl2 121.71(16) . . ? C5 C6 C7 120.2(2) . . ? C5 C6 H6 121.0(17) . . ? C7 C6 H6 118.6(16) . . ? C8 C7 C6 119.1(2) . . ? C8 C7 H7 120.4(14) . . ? C6 C7 H7 120.4(14) . . ? C7 C8 C11 121.23(19) . . ? C7 C8 Cl2' 120.0(3) . . ? C11 C8 Cl2' 118.1(3) . . ? C7 C8 H8 118.3(16) . . ? C11 C8 H8 120.3(16) . . ? Cl2' C8 H8 5.1(16) . . ? O1 C9 C15 108.79(13) . . ? O1 C9 C13 109.32(14) . . ? C15 C9 C13 108.99(14) . . ? O1 C9 C11 108.35(13) . . ? C15 C9 C11 106.82(14) . . ? C13 C9 C11 114.41(14) . . ? O2 C10 C17 107.66(14) . . ? O2 C10 C12 108.86(14) . . ? C17 C10 C12 110.79(16) . . ? O2 C10 C14 107.26(14) . . ? C17 C10 C14 107.66(15) . . ? C12 C10 C14 114.36(14) . . ? C12 C11 C8 120.32(17) . . ? C12 C11 C9 123.13(16) . . ? C8 C11 C9 116.43(16) . . ? C11 C12 C5 116.96(17) . . ? C11 C12 C10 121.20(16) . . ? C5 C12 C10 121.63(16) . . ? C14 C13 C1 117.59(17) . . ? C14 C13 C9 121.99(16) . . ? C1 C13 C9 120.33(15) . . ? C13 C14 C4 119.56(18) . . ? C13 C14 C10 122.35(16) . . ? C4 C14 C10 117.72(16) . . ? C16 C15 C9 175.0(2) . . ? C15 C16 H16 167.4(15) . . ? C18 C17 C10 175.5(2) . . ? C17 C18 H18 174.4(16) . . ? C20 C19 H19C 112.4(18) . . ? C20 C19 H19B 111.3(17) . . ? H19C C19 H19B 108(2) . . ? C20 C19 H19A 103.1(16) . . ? H19C C19 H19A 108(2) . . ? H19B C19 H19A 114(2) . . ? C19 C20 N1 114.08(19) . . ? C19 C20 H20B 110.4(13) . . ? N1 C20 H20B 111.0(14) . . ? C19 C20 H20A 114.2(14) . . ? N1 C20 H20A 103.3(14) . . ? H20B C20 H20A 103.2(19) . . ? C22 C21 H21C 111.7(13) . . ? C22 C21 H21B 105.8(14) . . ? H21C C21 H21B 108.1(19) . . ? C22 C21 H21A 113.6(14) . . ? H21C C21 H21A 109.9(19) . . ? H21B C21 H21A 107(2) . . ? N1 C22 C21 114.28(17) . . ? N1 C22 H22B 106.3(11) . . ? C21 C22 H22B 111.5(11) . . ? N1 C22 H22A 107.8(13) . . ? C21 C22 H22A 109.7(13) . . ? H22B C22 H22A 106.8(17) . . ? C24 C23 H23C 105.7(13) . . ? C24 C23 H23B 113.5(14) . . ? H23C C23 H23B 110.0(19) . . ? C24 C23 H23A 103.0(15) . . ? H23C C23 H23A 117(2) . . ? H23B C23 H23A 108(2) . . ? C23 C24 N1 113.51(17) . . ? C23 C24 H24B 112.4(12) . . ? N1 C24 H24B 106.1(12) . . ? C23 C24 H24A 113.3(13) . . ? N1 C24 H24A 101.6(13) . . ? H24B C24 H24A 109.2(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 C18 H18 O1 0.95(3) 2.14(3) 3.043(2) 159(2) 4_675 C16 H16 O2 0.95(2) 2.23(2) 3.125(2) 158(2) 1_455 C19 H19A Cl1 1.03(3) 2.87(3) 3.715(3) 140(2) 2_645 O1 H1 O3 0.83(2) 1.84(2) 2.6656(18) 177(2) . O2 H2 O3 0.87(3) 1.80(3) 2.6681(18) 178(3) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.437 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.048