data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Janet Scott' _publ_contact_author_email JANETSCO@TISCALI.CO.UK _publ_section_title ; Closing the Cavity: Reactive and Light Switchable Dienone-Ether Macrocycles ; loop_ _publ_author_name 'Janet Scott' 'Luke T. Higham' 'Christopher Strauss' # Attachment '3_Diels-Alder_dimer.CIF' data_intramolecular_Diels_Alder_derivative_of_3 _database_code_depnum_ccdc_archive 'CCDC 757254' #TrackingRef '3_Diels-Alder_dimer.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ;[B1],[B2]:[B3],[B4]-Bis(ethylene)-(3'E,8E)-3'-(2-[B1]oxy-3-methoxybenzylidene)- 8-(2-[B2]oxy-3-methoxybenzylidene)-3-(2-[B3]oxy-3-methoxyphenyl)-4-(2-[B4]oxy- 3-methoxyphenyl)-3,4,5,6,7,8-hexahydrospiro[chromene-2,1'-cyclohexan]-2'-one ; _chemical_name_common ; (B1),(B2):(B3),(B4)-Bis(ethylene)-(3'E,8E)-3'-(2-(B1)oxy-3- methoxybenzylidene)-8-(2-(B2)oxy-3-methoxybenzylidene)-3-(2-(B3)oxy-3- methoxyphenyl)-4-(2-(B4)oxy-3-methoxyphenyl)-3,4,5,6,7,8- hexahydrospiro(chromene-2,1'-cyclohexan)-2'-one ; _chemical_melting_point ? _chemical_formula_moiety '(C48 H48 O10)' _chemical_formula_sum 'C48 H48 O10' _chemical_formula_weight 784.86 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.91510(10) _cell_length_b 14.0630(2) _cell_length_c 14.5961(2) _cell_angle_alpha 73.414(1) _cell_angle_beta 81.794(1) _cell_angle_gamma 82.517(1) _cell_volume 1921.96(4) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9677 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32621 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 28.21 _reflns_number_total 9291 _reflns_number_gt 7182 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius collect' _computing_cell_refinement 'Nonius collect' _computing_data_reduction 'Nonius collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-seed _computing_publication_material ciftab _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^)+(0.0357P)^2^+0.7605P] 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 9291 _refine_ls_number_parameters 527 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 O3 O 0.38758(9) 0.02212(7) 0.20662(7) 0.0186(2) Uani 1 1 d . . . O6 O 0.74629(9) -0.33825(7) 0.76401(6) 0.01732(19) Uani 1 1 d . . . O1 O 0.81262(9) -0.29488(7) 0.41795(7) 0.0192(2) Uani 1 1 d . . . O4 O 0.53909(8) -0.21199(7) 0.46993(6) 0.01456(19) Uani 1 1 d . . . O5 O 0.50598(9) -0.45171(7) 0.85647(6) 0.01683(19) Uani 1 1 d . . . O2 O 0.75164(9) 0.02845(7) 0.16836(7) 0.0191(2) Uani 1 1 d . . . O8 O 0.26856(10) 0.08087(8) 0.04407(7) 0.0257(2) Uani 1 1 d . . . O10 O 0.97297(10) -0.45676(8) 0.83021(7) 0.0257(2) Uani 1 1 d . . . O9 O 0.50479(11) -0.64994(7) 0.93380(7) 0.0243(2) Uani 1 1 d . . . C21 C 0.63392(12) -0.35178(9) 0.58973(9) 0.0131(2) Uani 1 1 d . . . H21 H 0.6195 -0.3838 0.5393 0.016 Uiso 1 1 calc R . . O7 O 0.81370(11) 0.21286(8) 0.08353(8) 0.0314(3) Uani 1 1 d . . . C14 C 0.49684(12) -0.35836(9) 0.65614(9) 0.0133(2) Uani 1 1 d . . . H14 H 0.5009 -0.3250 0.7076 0.016 Uiso 1 1 calc R . . C10 C 0.35285(13) -0.15711(9) 0.34478(9) 0.0158(3) Uani 1 1 d . . . H10 H 0.4404 -0.1332 0.3356 0.019 Uiso 1 1 calc R . . C1 C 0.77154(12) -0.22823(9) 0.45559(9) 0.0132(2) Uani 1 1 d . . . C3 C 0.86956(12) -0.09658(10) 0.32707(9) 0.0156(3) Uani 1 1 d . . . H3 H 0.8683 -0.1407 0.2886 0.019 Uiso 1 1 calc R . . C22 C 0.64648(12) -0.24113(9) 0.53414(9) 0.0127(2) Uani 1 1 d . . . C43 C 0.94090(14) -0.54402(10) 0.62015(10) 0.0217(3) Uani 1 1 d . . . H43 H 0.9836 -0.5912 0.5872 0.026 Uiso 1 1 calc R . . C24 C 0.66952(14) -0.06503(10) 0.54247(10) 0.0180(3) Uani 1 1 d . . . H24A H 0.6611 -0.0234 0.5878 0.022 Uiso 1 1 calc R . . H24B H 0.6047 -0.0346 0.4941 0.022 Uiso 1 1 calc R . . C15 C 0.47450(12) -0.46750(9) 0.70210(9) 0.0143(3) Uani 1 1 d . . . C4 C 0.91829(13) 0.00260(10) 0.27892(9) 0.0158(3) Uani 1 1 d . . . C37 C 0.44503(13) -0.52732(10) 0.64664(9) 0.0179(3) Uani 1 1 d . . . H37 H 0.4324 -0.4982 0.5808 0.022 Uiso 1 1 calc R . . C26 C 1.02652(13) 0.03788(10) 0.30742(9) 0.0184(3) Uani 1 1 d . . . H26 H 1.0740 -0.0032 0.3589 0.022 Uiso 1 1 calc R . . C23 C 0.63355(13) -0.16987(9) 0.59719(9) 0.0158(3) Uani 1 1 d . . . H23A H 0.5383 -0.1658 0.6284 0.019 Uiso 1 1 calc R . . H23B H 0.6944 -0.1975 0.6486 0.019 Uiso 1 1 calc R . . C25 C 0.81580(14) -0.06811(10) 0.49206(9) 0.0187(3) Uani 1 1 d . . . H25A H 0.8390 0.0005 0.4583 0.022 Uiso 1 1 calc R . . H25B H 0.8810 -0.0982 0.5402 0.022 Uiso 1 1 calc R . . C44 C 0.82749(13) -0.48253(10) 0.58716(9) 0.0181(3) Uani 1 1 d . . . H44 H 0.7943 -0.4878 0.5311 0.022 Uiso 1 1 calc R . . C42 C 0.99251(14) -0.53718(10) 0.70099(10) 0.0220(3) Uani 1 1 d . . . H42 H 1.0712 -0.5789 0.7232 0.026 Uiso 1 1 calc R . . C20 C 0.75998(12) -0.41262(9) 0.63388(9) 0.0143(3) Uani 1 1 d . . . C19 C 0.81036(13) -0.40775(9) 0.71738(9) 0.0154(3) Uani 1 1 d . . . C13 C 0.38323(13) -0.30474(9) 0.59534(9) 0.0146(3) Uani 1 1 d . . . C12 C 0.41083(12) -0.24344(9) 0.50675(9) 0.0136(2) Uani 1 1 d . . . C17 C 0.63522(14) -0.46737(10) 0.89589(9) 0.0188(3) Uani 1 1 d . . . H17A H 0.6958 -0.5192 0.8724 0.023 Uiso 1 1 calc R . . H17B H 0.6200 -0.4906 0.9669 0.023 Uiso 1 1 calc R . . C9 C 0.27897(13) -0.13019(10) 0.25892(9) 0.0164(3) Uani 1 1 d . . . C5 C 0.85281(13) 0.06401(10) 0.20212(9) 0.0163(3) Uani 1 1 d . . . C30 C 0.23853(13) -0.00982(10) 0.10493(9) 0.0191(3) Uani 1 1 d . . . C27 C 1.06474(14) 0.13256(11) 0.26080(10) 0.0207(3) Uani 1 1 d . . . H27 H 1.1399 0.1551 0.2797 0.025 Uiso 1 1 calc R . . C2 C 0.82704(12) -0.12856(9) 0.42112(9) 0.0142(3) Uani 1 1 d . . . C36 C 0.23738(13) -0.32459(10) 0.63546(10) 0.0191(3) Uani 1 1 d . . . H36A H 0.2205 -0.3170 0.7016 0.023 Uiso 1 1 calc R . . H36B H 0.2243 -0.3942 0.6390 0.023 Uiso 1 1 calc R . . C40 C 0.48264(13) -0.61435(10) 0.83896(9) 0.0182(3) Uani 1 1 d . . . C6 C 0.61563(13) 0.05285(11) 0.20890(10) 0.0193(3) Uani 1 1 d . . . H6A H 0.5938 0.1260 0.1941 0.023 Uiso 1 1 calc R . . H6B H 0.6053 0.0243 0.2796 0.023 Uiso 1 1 calc R . . C35 C 0.13378(13) -0.25422(11) 0.57430(10) 0.0215(3) Uani 1 1 d . . . H35A H 0.0416 -0.2778 0.5951 0.026 Uiso 1 1 calc R . . H35B H 0.1304 -0.1867 0.5831 0.026 Uiso 1 1 calc R . . C16 C 0.48924(13) -0.51117(10) 0.79856(9) 0.0153(3) Uani 1 1 d . . . C11 C 0.31289(12) -0.21113(9) 0.43466(9) 0.0147(3) Uani 1 1 d . . . C28 C 0.99493(14) 0.19506(11) 0.18682(10) 0.0219(3) Uani 1 1 d . . . H28 H 1.0198 0.2608 0.1571 0.026 Uiso 1 1 calc R . . C38 C 0.43409(14) -0.62813(10) 0.68648(10) 0.0215(3) Uani 1 1 d . . . H38 H 0.4127 -0.6674 0.6482 0.026 Uiso 1 1 calc R . . C31 C 0.15219(14) -0.07152(11) 0.08800(10) 0.0222(3) Uani 1 1 d . . . H31 H 0.1083 -0.0521 0.0309 0.027 Uiso 1 1 calc R . . C18 C 0.70212(14) -0.37154(11) 0.86589(9) 0.0199(3) Uani 1 1 d . . . H18A H 0.6368 -0.3189 0.8844 0.024 Uiso 1 1 calc R . . H18B H 0.7825 -0.3804 0.9017 0.024 Uiso 1 1 calc R . . C46 C 0.17807(15) 0.12684(12) -0.02743(10) 0.0258(3) Uani 1 1 d . . . H46A H 0.1853 0.0872 -0.0736 0.039 Uiso 1 1 calc R . . H46B H 0.2031 0.1942 -0.0612 0.039 Uiso 1 1 calc R . . H46C H 0.0838 0.1307 0.0035 0.039 Uiso 1 1 calc R . . C29 C 0.88888(14) 0.16070(10) 0.15690(10) 0.0203(3) Uani 1 1 d . . . C33 C 0.19194(14) -0.19170(11) 0.23991(10) 0.0203(3) Uani 1 1 d . . . H33 H 0.1752 -0.2538 0.2851 0.024 Uiso 1 1 calc R . . C41 C 0.92827(14) -0.46892(10) 0.74933(9) 0.0193(3) Uani 1 1 d . . . C39 C 0.45425(14) -0.67230(10) 0.78254(10) 0.0217(3) Uani 1 1 d . . . H39 H 0.4486 -0.7419 0.8094 0.026 Uiso 1 1 calc R . . C7 C 0.52413(13) 0.00754(11) 0.16254(10) 0.0196(3) Uani 1 1 d . . . H7A H 0.5296 0.0402 0.0926 0.023 Uiso 1 1 calc R . . H7B H 0.5525 -0.0645 0.1723 0.023 Uiso 1 1 calc R . . C8 C 0.30230(13) -0.04017(10) 0.18952(9) 0.0168(3) Uani 1 1 d . . . C34 C 0.17428(13) -0.25014(10) 0.46867(10) 0.0196(3) Uani 1 1 d . . . H34A H 0.1771 -0.3177 0.4600 0.023 Uiso 1 1 calc R . . H34B H 0.1050 -0.2062 0.4295 0.023 Uiso 1 1 calc R . . C47 C 0.52472(16) -0.75606(10) 0.97150(11) 0.0266(3) Uani 1 1 d . . . H47A H 0.4379 -0.7846 0.9771 0.040 Uiso 1 1 calc R . . H47B H 0.5570 -0.7724 1.0351 0.040 Uiso 1 1 calc R . . H47C H 0.5929 -0.7837 0.9281 0.040 Uiso 1 1 calc R . . C48 C 1.09040(16) -0.52119(12) 0.86453(11) 0.0306(4) Uani 1 1 d . . . H48A H 1.0725 -0.5908 0.8761 0.046 Uiso 1 1 calc R . . H48B H 1.1090 -0.5101 0.9246 0.046 Uiso 1 1 calc R . . H48C H 1.1699 -0.5067 0.8163 0.046 Uiso 1 1 calc R . . C32 C 0.13052(14) -0.16229(11) 0.15567(10) 0.0225(3) Uani 1 1 d . . . H32 H 0.0723 -0.2049 0.1437 0.027 Uiso 1 1 calc R . . C45 C 0.8282(2) 0.31608(13) 0.04715(15) 0.0508(5) Uani 1 1 d . . . H45A H 0.8032 0.3484 0.0993 0.076 Uiso 1 1 calc R . . H45B H 0.7680 0.3454 -0.0035 0.076 Uiso 1 1 calc R . . H45C H 0.9234 0.3259 0.0205 0.076 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 O3 0.0152(4) 0.0193(5) 0.0212(5) -0.0034(4) -0.0039(4) -0.0037(4) O6 0.0209(5) 0.0156(5) 0.0147(4) -0.0025(4) -0.0026(4) -0.0023(4) O1 0.0216(5) 0.0149(5) 0.0189(5) -0.0039(4) 0.0021(4) -0.0003(4) O4 0.0109(4) 0.0164(5) 0.0142(4) 0.0006(3) -0.0036(3) -0.0021(3) O5 0.0193(5) 0.0171(5) 0.0143(4) -0.0040(4) -0.0030(4) -0.0022(4) O2 0.0159(4) 0.0229(5) 0.0197(5) -0.0056(4) -0.0030(4) -0.0056(4) O8 0.0245(5) 0.0271(6) 0.0210(5) 0.0069(4) -0.0101(4) -0.0080(4) O10 0.0245(5) 0.0269(6) 0.0259(5) -0.0036(4) -0.0142(4) 0.0012(4) O9 0.0377(6) 0.0154(5) 0.0162(5) 0.0027(4) -0.0045(4) -0.0042(4) C21 0.0144(6) 0.0118(6) 0.0124(6) -0.0019(5) -0.0015(5) -0.0018(5) O7 0.0386(6) 0.0214(6) 0.0303(6) 0.0075(4) -0.0160(5) -0.0084(5) C14 0.0142(6) 0.0125(6) 0.0122(6) -0.0012(5) -0.0013(5) -0.0026(5) C10 0.0140(6) 0.0136(6) 0.0203(6) -0.0041(5) -0.0046(5) -0.0011(5) C1 0.0120(6) 0.0129(6) 0.0132(6) -0.0005(5) -0.0038(5) 0.0002(5) C3 0.0132(6) 0.0155(6) 0.0179(6) -0.0039(5) -0.0023(5) -0.0018(5) C22 0.0114(6) 0.0127(6) 0.0131(6) -0.0013(5) -0.0027(5) -0.0014(5) C43 0.0190(7) 0.0176(7) 0.0247(7) -0.0033(6) 0.0019(6) 0.0021(5) C24 0.0219(7) 0.0129(6) 0.0188(6) -0.0048(5) 0.0001(5) -0.0019(5) C15 0.0116(6) 0.0138(6) 0.0155(6) -0.0015(5) -0.0001(5) -0.0013(5) C4 0.0151(6) 0.0170(7) 0.0143(6) -0.0036(5) 0.0023(5) -0.0035(5) C37 0.0200(6) 0.0179(7) 0.0156(6) -0.0031(5) -0.0029(5) -0.0025(5) C26 0.0173(6) 0.0215(7) 0.0154(6) -0.0033(5) -0.0012(5) -0.0032(5) C23 0.0175(6) 0.0145(6) 0.0148(6) -0.0035(5) -0.0001(5) -0.0024(5) C25 0.0210(7) 0.0171(7) 0.0182(6) -0.0038(5) -0.0009(5) -0.0067(5) C44 0.0188(6) 0.0164(7) 0.0174(6) -0.0025(5) -0.0009(5) -0.0011(5) C42 0.0151(6) 0.0190(7) 0.0263(7) 0.0018(6) -0.0024(6) 0.0010(5) C20 0.0130(6) 0.0122(6) 0.0149(6) 0.0007(5) 0.0005(5) -0.0036(5) C19 0.0149(6) 0.0131(6) 0.0169(6) -0.0022(5) 0.0005(5) -0.0037(5) C13 0.0143(6) 0.0131(6) 0.0167(6) -0.0047(5) -0.0016(5) -0.0011(5) C12 0.0116(6) 0.0119(6) 0.0165(6) -0.0030(5) -0.0009(5) -0.0007(5) C17 0.0211(7) 0.0207(7) 0.0134(6) -0.0016(5) -0.0036(5) -0.0031(5) C9 0.0140(6) 0.0182(7) 0.0159(6) -0.0033(5) -0.0027(5) 0.0004(5) C5 0.0149(6) 0.0187(7) 0.0155(6) -0.0044(5) -0.0007(5) -0.0044(5) C30 0.0164(6) 0.0218(7) 0.0160(6) 0.0001(5) -0.0024(5) -0.0017(5) C27 0.0195(7) 0.0247(7) 0.0198(7) -0.0074(6) 0.0007(5) -0.0095(6) C2 0.0097(6) 0.0145(6) 0.0173(6) -0.0025(5) -0.0024(5) -0.0004(5) C36 0.0152(6) 0.0206(7) 0.0179(6) -0.0005(5) 0.0007(5) -0.0024(5) C40 0.0197(6) 0.0170(7) 0.0147(6) 0.0003(5) -0.0008(5) -0.0019(5) C6 0.0156(6) 0.0219(7) 0.0193(7) -0.0029(5) -0.0027(5) -0.0034(5) C35 0.0140(6) 0.0226(7) 0.0239(7) -0.0015(6) 0.0004(5) -0.0009(5) C16 0.0153(6) 0.0152(6) 0.0152(6) -0.0044(5) -0.0001(5) -0.0021(5) C11 0.0139(6) 0.0116(6) 0.0182(6) -0.0036(5) -0.0030(5) 0.0000(5) C28 0.0262(7) 0.0180(7) 0.0207(7) -0.0028(6) 0.0010(6) -0.0093(6) C38 0.0253(7) 0.0181(7) 0.0239(7) -0.0088(6) -0.0042(6) -0.0037(5) C31 0.0187(7) 0.0299(8) 0.0174(7) -0.0026(6) -0.0065(5) -0.0037(6) C18 0.0234(7) 0.0238(7) 0.0136(6) -0.0055(5) -0.0021(5) -0.0047(6) C46 0.0265(7) 0.0276(8) 0.0200(7) 0.0010(6) -0.0094(6) -0.0002(6) C29 0.0218(7) 0.0191(7) 0.0178(6) -0.0005(5) -0.0030(5) -0.0039(5) C33 0.0190(7) 0.0195(7) 0.0209(7) -0.0020(5) -0.0031(5) -0.0037(5) C41 0.0182(6) 0.0196(7) 0.0178(6) 0.0014(5) -0.0048(5) -0.0051(5) C39 0.0260(7) 0.0126(7) 0.0251(7) -0.0022(5) -0.0020(6) -0.0036(5) C7 0.0159(6) 0.0229(7) 0.0193(7) -0.0031(6) -0.0024(5) -0.0050(5) C8 0.0131(6) 0.0194(7) 0.0180(6) -0.0049(5) -0.0026(5) -0.0019(5) C34 0.0139(6) 0.0204(7) 0.0225(7) -0.0013(6) -0.0049(5) -0.0021(5) C47 0.0333(8) 0.0155(7) 0.0249(7) 0.0051(6) -0.0052(6) -0.0023(6) C48 0.0263(8) 0.0305(9) 0.0316(8) 0.0021(7) -0.0151(7) -0.0014(6) C32 0.0194(7) 0.0266(8) 0.0236(7) -0.0074(6) -0.0045(6) -0.0067(6) C45 0.0633(13) 0.0241(9) 0.0576(12) 0.0167(8) -0.0311(10) -0.0137(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C8 1.3866(16) . ? O3 C7 1.4296(16) . ? O6 C19 1.3846(16) . ? O6 C18 1.4465(15) . ? O1 C1 1.2154(15) . ? O4 C12 1.3848(15) . ? O4 C22 1.4602(14) . ? O5 C16 1.3859(15) . ? O5 C17 1.4444(16) . ? O2 C5 1.3826(15) . ? O2 C6 1.4333(16) . ? O8 C30 1.3715(17) . ? O8 C46 1.4293(16) . ? O10 C41 1.3798(16) . ? O10 C48 1.4353(17) . ? O9 C40 1.3702(16) . ? O9 C47 1.4333(17) . ? C21 C20 1.5318(17) . ? C21 C22 1.5479(17) . ? C21 C14 1.5495(17) . ? O7 C29 1.3702(16) . ? O7 C45 1.415(2) . ? C14 C13 1.5189(17) . ? C14 C15 1.5210(17) . ? C10 C11 1.3477(18) . ? C10 C9 1.4730(17) . ? C1 C2 1.4966(18) . ? C1 C22 1.5553(17) . ? C3 C2 1.3403(18) . ? C3 C4 1.4804(18) . ? C22 C23 1.5255(17) . ? C43 C44 1.3812(19) . ? C43 C42 1.383(2) . ? C24 C23 1.5239(18) . ? C24 C25 1.5310(18) . ? C15 C16 1.3866(17) . ? C15 C37 1.4031(18) . ? C4 C5 1.3903(18) . ? C4 C26 1.3981(18) . ? C37 C38 1.3824(19) . ? C26 C27 1.3856(19) . ? C25 C2 1.5007(18) . ? C44 C20 1.4002(18) . ? C42 C41 1.387(2) . ? C20 C19 1.4035(18) . ? C19 C41 1.4103(18) . ? C13 C12 1.3469(18) . ? C13 C36 1.5108(17) . ? C12 C11 1.4698(17) . ? C17 C18 1.5036(19) . ? C9 C8 1.3997(18) . ? C9 C33 1.4035(19) . ? C5 C29 1.3998(19) . ? C30 C31 1.3868(19) . ? C30 C8 1.3993(18) . ? C27 C28 1.390(2) . ? C36 C35 1.5244(18) . ? C40 C39 1.3896(19) . ? C40 C16 1.4081(18) . ? C6 C7 1.5030(18) . ? C35 C34 1.5234(19) . ? C11 C34 1.5106(18) . ? C28 C29 1.3835(19) . ? C38 C39 1.3935(19) . ? C31 C32 1.394(2) . ? C33 C32 1.3826(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O3 C7 111.66(10) . . ? C19 O6 C18 118.72(10) . . ? C12 O4 C22 117.45(9) . . ? C16 O5 C17 116.78(10) . . ? C5 O2 C6 114.12(10) . . ? C30 O8 C46 116.87(11) . . ? C41 O10 C48 116.16(12) . . ? C40 O9 C47 116.77(11) . . ? C20 C21 C22 117.86(10) . . ? C20 C21 C14 116.65(10) . . ? C22 C21 C14 108.22(10) . . ? C29 O7 C45 116.95(12) . . ? C13 C14 C15 111.49(10) . . ? C13 C14 C21 108.06(10) . . ? C15 C14 C21 108.93(10) . . ? C11 C10 C9 128.71(12) . . ? O1 C1 C2 121.99(11) . . ? O1 C1 C22 119.74(11) . . ? C2 C1 C22 117.89(10) . . ? C2 C3 C4 124.61(12) . . ? O4 C22 C23 109.52(10) . . ? O4 C22 C21 106.76(9) . . ? C23 C22 C21 114.92(10) . . ? O4 C22 C1 97.71(9) . . ? C23 C22 C1 114.13(10) . . ? C21 C22 C1 112.11(10) . . ? C44 C43 C42 120.28(13) . . ? C23 C24 C25 110.45(11) . . ? C16 C15 C37 118.57(12) . . ? C16 C15 C14 120.74(11) . . ? C37 C15 C14 120.62(11) . . ? C5 C4 C26 118.33(12) . . ? C5 C4 C3 118.54(11) . . ? C26 C4 C3 123.13(11) . . ? C38 C37 C15 120.88(12) . . ? C27 C26 C4 120.21(12) . . ? C24 C23 C22 113.83(10) . . ? C2 C25 C24 109.44(10) . . ? C43 C44 C20 122.00(13) . . ? C43 C42 C41 119.40(12) . . ? C44 C20 C19 117.57(11) . . ? C44 C20 C21 115.67(11) . . ? C19 C20 C21 126.71(11) . . ? O6 C19 C20 118.54(11) . . ? O6 C19 C41 121.21(11) . . ? C20 C19 C41 120.15(12) . . ? C12 C13 C36 120.38(11) . . ? C12 C13 C14 121.41(11) . . ? C36 C13 C14 118.18(11) . . ? C13 C12 O4 123.58(11) . . ? C13 C12 C11 123.94(11) . . ? O4 C12 C11 112.18(10) . . ? O5 C17 C18 109.65(11) . . ? C8 C9 C33 117.81(12) . . ? C8 C9 C10 118.13(12) . . ? C33 C9 C10 123.97(12) . . ? O2 C5 C4 119.48(11) . . ? O2 C5 C29 119.12(11) . . ? C4 C5 C29 121.38(12) . . ? O8 C30 C31 124.95(12) . . ? O8 C30 C8 115.77(12) . . ? C31 C30 C8 119.27(12) . . ? C26 C27 C28 121.08(12) . . ? C3 C2 C1 116.99(11) . . ? C3 C2 C25 125.29(12) . . ? C1 C2 C25 117.34(11) . . ? C13 C36 C35 112.26(11) . . ? O9 C40 C39 124.73(12) . . ? O9 C40 C16 115.77(12) . . ? C39 C40 C16 119.50(12) . . ? O2 C6 C7 104.94(11) . . ? C34 C35 C36 109.87(11) . . ? O5 C16 C15 119.37(11) . . ? O5 C16 C40 119.72(11) . . ? C15 C16 C40 120.87(12) . . ? C10 C11 C12 120.06(11) . . ? C10 C11 C34 125.36(12) . . ? C12 C11 C34 114.42(11) . . ? C29 C28 C27 119.36(13) . . ? C37 C38 C39 120.26(13) . . ? C30 C31 C32 119.31(12) . . ? O6 C18 C17 114.19(11) . . ? O7 C29 C28 125.72(13) . . ? O7 C29 C5 114.71(12) . . ? C28 C29 C5 119.56(12) . . ? C32 C33 C9 120.24(13) . . ? O10 C41 C42 123.32(12) . . ? O10 C41 C19 116.14(12) . . ? C42 C41 C19 120.54(12) . . ? C40 C39 C38 119.82(13) . . ? O3 C7 C6 107.36(11) . . ? O3 C8 C30 119.11(12) . . ? O3 C8 C9 118.98(11) . . ? C30 C8 C9 121.88(12) . . ? C11 C34 C35 110.54(11) . . ? C33 C32 C31 121.46(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C20 C21 C14 C13 -172.42(10) . . . . ? C22 C21 C14 C13 51.88(13) . . . . ? C20 C21 C14 C15 -51.15(14) . . . . ? C22 C21 C14 C15 173.15(9) . . . . ? C12 O4 C22 C23 -82.14(12) . . . . ? C12 O4 C22 C21 42.87(13) . . . . ? C12 O4 C22 C1 158.81(10) . . . . ? C20 C21 C22 O4 158.34(10) . . . . ? C14 C21 C22 O4 -66.59(12) . . . . ? C20 C21 C22 C23 -80.01(13) . . . . ? C14 C21 C22 C23 55.06(13) . . . . ? C20 C21 C22 C1 52.46(14) . . . . ? C14 C21 C22 C1 -172.46(10) . . . . ? O1 C1 C22 O4 -83.14(13) . . . . ? C2 C1 C22 O4 89.96(11) . . . . ? O1 C1 C22 C23 161.39(11) . . . . ? C2 C1 C22 C23 -25.51(15) . . . . ? O1 C1 C22 C21 28.52(15) . . . . ? C2 C1 C22 C21 -158.38(10) . . . . ? C13 C14 C15 C16 -133.75(12) . . . . ? C21 C14 C15 C16 107.10(13) . . . . ? C13 C14 C15 C37 49.36(15) . . . . ? C21 C14 C15 C37 -69.79(14) . . . . ? C2 C3 C4 C5 -123.05(14) . . . . ? C2 C3 C4 C26 56.46(18) . . . . ? C16 C15 C37 C38 -1.52(19) . . . . ? C14 C15 C37 C38 175.44(12) . . . . ? C5 C4 C26 C27 1.19(19) . . . . ? C3 C4 C26 C27 -178.32(12) . . . . ? C25 C24 C23 C22 -57.89(14) . . . . ? O4 C22 C23 C24 -69.44(13) . . . . ? C21 C22 C23 C24 170.42(10) . . . . ? C1 C22 C23 C24 38.90(14) . . . . ? C23 C24 C25 C2 61.06(14) . . . . ? C42 C43 C44 C20 -0.8(2) . . . . ? C44 C43 C42 C41 0.8(2) . . . . ? C43 C44 C20 C19 -0.96(19) . . . . ? C43 C44 C20 C21 -178.62(12) . . . . ? C22 C21 C20 C44 -106.81(13) . . . . ? C14 C21 C20 C44 121.82(12) . . . . ? C22 C21 C20 C19 75.77(16) . . . . ? C14 C21 C20 C19 -55.60(17) . . . . ? C18 O6 C19 C20 127.73(12) . . . . ? C18 O6 C19 C41 -55.74(16) . . . . ? C44 C20 C19 O6 179.15(11) . . . . ? C21 C20 C19 O6 -3.48(19) . . . . ? C44 C20 C19 C41 2.58(18) . . . . ? C21 C20 C19 C41 179.95(12) . . . . ? C15 C14 C13 C12 -134.53(12) . . . . ? C21 C14 C13 C12 -14.87(16) . . . . ? C15 C14 C13 C36 43.41(15) . . . . ? C21 C14 C13 C36 163.08(11) . . . . ? C36 C13 C12 O4 171.67(11) . . . . ? C14 C13 C12 O4 -10.43(19) . . . . ? C36 C13 C12 C11 -15.20(19) . . . . ? C14 C13 C12 C11 162.70(12) . . . . ? C22 O4 C12 C13 -4.96(17) . . . . ? C22 O4 C12 C11 -178.81(10) . . . . ? C16 O5 C17 C18 122.55(12) . . . . ? C11 C10 C9 C8 149.62(14) . . . . ? C11 C10 C9 C33 -33.9(2) . . . . ? C6 O2 C5 C4 94.50(14) . . . . ? C6 O2 C5 C29 -86.69(14) . . . . ? C26 C4 C5 O2 175.70(11) . . . . ? C3 C4 C5 O2 -4.77(18) . . . . ? C26 C4 C5 C29 -3.09(19) . . . . ? C3 C4 C5 C29 176.45(12) . . . . ? C46 O8 C30 C31 17.8(2) . . . . ? C46 O8 C30 C8 -162.56(12) . . . . ? C4 C26 C27 C28 1.6(2) . . . . ? C4 C3 C2 C1 175.55(11) . . . . ? C4 C3 C2 C25 2.9(2) . . . . ? O1 C1 C2 C3 31.25(17) . . . . ? C22 C1 C2 C3 -141.69(11) . . . . ? O1 C1 C2 C25 -155.48(12) . . . . ? C22 C1 C2 C25 31.59(15) . . . . ? C24 C25 C2 C3 124.05(13) . . . . ? C24 C25 C2 C1 -48.60(15) . . . . ? C12 C13 C36 C35 -10.98(18) . . . . ? C14 C13 C36 C35 171.06(11) . . . . ? C47 O9 C40 C39 12.0(2) . . . . ? C47 O9 C40 C16 -168.40(12) . . . . ? C5 O2 C6 C7 179.94(10) . . . . ? C13 C36 C35 C34 48.12(15) . . . . ? C17 O5 C16 C15 -115.20(13) . . . . ? C17 O5 C16 C40 67.00(15) . . . . ? C37 C15 C16 O5 -174.18(11) . . . . ? C14 C15 C16 O5 8.86(17) . . . . ? C37 C15 C16 C40 3.59(19) . . . . ? C14 C15 C16 C40 -173.37(11) . . . . ? O9 C40 C16 O5 -5.09(18) . . . . ? C39 C40 C16 O5 174.56(12) . . . . ? O9 C40 C16 C15 177.14(11) . . . . ? C39 C40 C16 C15 -3.21(19) . . . . ? C9 C10 C11 C12 170.03(12) . . . . ? C9 C10 C11 C34 -5.0(2) . . . . ? C13 C12 C11 C10 -173.91(13) . . . . ? O4 C12 C11 C10 -0.09(17) . . . . ? C13 C12 C11 C34 1.67(18) . . . . ? O4 C12 C11 C34 175.49(10) . . . . ? C26 C27 C28 C29 -2.5(2) . . . . ? C15 C37 C38 C39 -0.9(2) . . . . ? O8 C30 C31 C32 179.76(13) . . . . ? C8 C30 C31 C32 0.2(2) . . . . ? C19 O6 C18 C17 -42.67(15) . . . . ? O5 C17 C18 O6 -67.56(14) . . . . ? C45 O7 C29 C28 -12.4(2) . . . . ? C45 O7 C29 C5 168.78(15) . . . . ? C27 C28 C29 O7 -178.21(13) . . . . ? C27 C28 C29 C5 0.6(2) . . . . ? O2 C5 C29 O7 2.35(18) . . . . ? C4 C5 C29 O7 -178.86(12) . . . . ? O2 C5 C29 C28 -176.56(12) . . . . ? C4 C5 C29 C28 2.2(2) . . . . ? C8 C9 C33 C32 -1.0(2) . . . . ? C10 C9 C33 C32 -177.53(12) . . . . ? C48 O10 C41 C42 -1.40(19) . . . . ? C48 O10 C41 C19 178.10(12) . . . . ? C43 C42 C41 O10 -179.72(13) . . . . ? C43 C42 C41 C19 0.8(2) . . . . ? O6 C19 C41 O10 1.46(18) . . . . ? C20 C19 C41 O10 177.94(11) . . . . ? O6 C19 C41 C42 -179.03(12) . . . . ? C20 C19 C41 C42 -2.55(19) . . . . ? O9 C40 C39 C38 -179.69(13) . . . . ? C16 C40 C39 C38 0.7(2) . . . . ? C37 C38 C39 C40 1.3(2) . . . . ? C8 O3 C7 C6 -162.90(11) . . . . ? O2 C6 C7 O3 175.04(10) . . . . ? C7 O3 C8 C30 -85.93(14) . . . . ? C7 O3 C8 C9 96.15(14) . . . . ? O8 C30 C8 O3 0.94(18) . . . . ? C31 C30 C8 O3 -179.42(12) . . . . ? O8 C30 C8 C9 178.80(12) . . . . ? C31 C30 C8 C9 -1.6(2) . . . . ? C33 C9 C8 O3 179.83(11) . . . . ? C10 C9 C8 O3 -3.44(18) . . . . ? C33 C9 C8 C30 1.97(19) . . . . ? C10 C9 C8 C30 178.70(12) . . . . ? C10 C11 C34 C35 -148.24(13) . . . . ? C12 C11 C34 C35 36.45(15) . . . . ? C36 C35 C34 C11 -61.14(15) . . . . ? C9 C33 C32 C31 -0.3(2) . . . . ? C30 C31 C32 C33 0.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.21 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.358 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.047 _exptl_crystal_recrystallization_method 'Slow evaporation from dichloromethane.' # Attachment 'EEZZ-1_CHCl3.CIF' data_E,E,Z,Z_1_CHCl3 _database_code_depnum_ccdc_archive 'CCDC 757255' #TrackingRef 'EEZZ-1_CHCl3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ;(1E,11E,16Z,26Z)-3,4:9,10:18,19:24,25-Tetrabenzo-14,29-dimethyl-5,8,20,23- tetraoxa-tricyclo[25.3.1.1(12,16)]dotriaconta-1,3,9,11,16,18,24,26-octaene- 31,32-dione chloroform solvate ; _chemical_name_common ; (1E,11E,16Z,26Z)-3,4:9,10:18,19:24,25-Tetrabenzo-14,29- dimethyl-5,8,20,23-tetraoxa-tricyclo(25.3.1.1(12,16))dotriaconta- 1,3,9,11,16,18,24,26-octaene-31,32-dione chloroform solvate ; _chemical_melting_point ? _chemical_formula_moiety '(C46 H44 O6)0.5 (C H Cl3)' _chemical_formula_sum 'C24 H23 Cl3 O3' _chemical_formula_weight 465.77 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_int_tables_number 18 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 15.7123(2) _cell_length_b 17.7118(3) _cell_length_c 8.1342(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2263.69(15) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.428 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8823 _exptl_absorpt_correction_T_max 0.9193 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7880 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0630 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 27.87 _reflns_number_total 4996 _reflns_number_gt 3865 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius collect' _computing_cell_refinement 'Nonius collect' _computing_data_reduction 'Nonius collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-seed _computing_publication_material ciftab _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. Macrocycle exhibits disorder of part of the methyl-cyclohexyl moiety, C(14)-C(13)-C(23), and this is modelled over two positions with 70 and 30 % occupancy for major and minor components, respectively. Atoms of the disordered methyl-cyclohexyl moiety are modelled isotropically, while all other non-hydrogen atoms are allowed to refine anisotropically. Hydrogen atoms were inserted in geometrically determined positions with temperature factors fixed at 1.2 of the parent atom. ; _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^)+(0.0322P)^2^+0.3160P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.44(5) _refine_ls_number_reflns 4996 _refine_ls_number_parameters 270 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.0841 _refine_ls_wR_factor_gt 0.0757 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 -0.00148(4) 0.10198(4) 0.57130(9) 0.04642(19) Uani 1 1 d . . . Cl2 Cl 0.03480(4) 0.24342(4) 0.73658(8) 0.04431(19) Uani 1 1 d . . . Cl3 Cl -0.13235(4) 0.17617(4) 0.76025(8) 0.04406(18) Uani 1 1 d . . . C1G C -0.04312(15) 0.18952(14) 0.6332(3) 0.0296(6) Uani 1 1 d . . . H1G H -0.0615 0.2179 0.5330 0.036 Uiso 1 1 calc R . . O3 O -0.01000(9) 0.41701(8) 0.32884(16) 0.0206(3) Uani 1 1 d . . . O2 O -0.09224(8) 0.50468(10) 0.82858(16) 0.0197(3) Uani 1 1 d . . . O1 O -0.14476(10) 0.31136(9) 0.48140(18) 0.0282(4) Uani 1 1 d . . . C3 C -0.19890(13) 0.44994(13) 0.5958(2) 0.0189(5) Uani 1 1 d . A . H3 H -0.1671 0.4146 0.6587 0.023 Uiso 1 1 calc R . . C6 C -0.03691(14) 0.52663(13) 0.9611(2) 0.0208(5) Uani 1 1 d . . . H6A H -0.0676 0.5238 1.0672 0.025 Uiso 1 1 calc R . . H6B H -0.0169 0.5791 0.9449 0.025 Uiso 1 1 calc R . . C7 C 0.02317(16) 0.46337(13) 0.4576(2) 0.0263(5) Uani 1 1 d . . . H7A H 0.0847 0.4722 0.4400 0.032 Uiso 1 1 calc R . . H7B H 0.0158 0.4378 0.5649 0.032 Uiso 1 1 calc R . . C22 C 0.02155(15) 0.22892(14) 0.1671(3) 0.0273(6) Uani 1 1 d . . . H22 H -0.0070 0.1947 0.0960 0.033 Uiso 1 1 calc R . . C5 C -0.16436(13) 0.54748(13) 0.8040(3) 0.0193(5) Uani 1 1 d . A . C2 C -0.21725(13) 0.42760(13) 0.4413(3) 0.0194(5) Uani 1 1 d . . . C17 C -0.25444(15) 0.65373(14) 0.8544(3) 0.0302(6) Uani 1 1 d . . . H17 H -0.2661 0.6992 0.9121 0.036 Uiso 1 1 calc R . . C18 C -0.18112(15) 0.61352(13) 0.8895(3) 0.0240(5) Uani 1 1 d . . . H18 H -0.1427 0.6310 0.9713 0.029 Uiso 1 1 calc R . . C8 C 0.02805(13) 0.34848(13) 0.3039(2) 0.0194(5) Uani 1 1 d . . . C21 C 0.09993(16) 0.20886(15) 0.2314(3) 0.0341(6) Uani 1 1 d . . . H21 H 0.1241 0.1611 0.2063 0.041 Uiso 1 1 calc R . . C16 C -0.31077(16) 0.62852(15) 0.7368(3) 0.0348(6) Uani 1 1 d . . . H16 H -0.3608 0.6567 0.7132 0.042 Uiso 1 1 calc R . . C20 C 0.14265(15) 0.25862(16) 0.3319(3) 0.0337(6) Uani 1 1 d . . . H20 H 0.1965 0.2452 0.3764 0.040 Uiso 1 1 calc R . . C1 C -0.17447(13) 0.35686(13) 0.3846(3) 0.0202(5) Uani 1 1 d . A . C10 C -0.10019(13) 0.31675(13) 0.1296(3) 0.0219(5) Uani 1 1 d . A . H10 H -0.1052 0.3080 0.0147 0.026 Uiso 1 1 calc R . . C9 C -0.01636(13) 0.29759(12) 0.2036(2) 0.0198(5) Uani 1 1 d . . . C15 C -0.29436(15) 0.56225(15) 0.6533(3) 0.0299(6) Uani 1 1 d . A . H15 H -0.3343 0.5448 0.5743 0.036 Uiso 1 1 calc R . . C4 C -0.22024(13) 0.52003(12) 0.6820(2) 0.0193(5) Uani 1 1 d . . . C11 C -0.16932(14) 0.34460(13) 0.2032(3) 0.0227(5) Uani 1 1 d . . . C14 C -0.2784(2) 0.4666(2) 0.3268(4) 0.0184(9) Uiso 0.70 1 d P A 1 H14A H -0.2728 0.5218 0.3426 0.022 Uiso 0.70 1 calc PR A 1 H14B H -0.3371 0.4523 0.3586 0.022 Uiso 0.70 1 calc PR A 1 C12 C -0.24772(15) 0.36802(15) 0.1097(3) 0.0328(6) Uani 1 1 d . A . H12A H -0.2384 0.3607 -0.0096 0.039 Uiso 1 1 calc R B 1 H12B H -0.2966 0.3364 0.1437 0.039 Uiso 1 1 calc R B 1 C23 C -0.3452(3) 0.4754(3) 0.0482(5) 0.0258(11) Uiso 0.70 1 d P A 1 H23A H -0.3358 0.4679 -0.0698 0.039 Uiso 0.70 1 calc PR A 1 H23B H -0.3551 0.5291 0.0700 0.039 Uiso 0.70 1 calc PR A 1 H23C H -0.3949 0.4461 0.0833 0.039 Uiso 0.70 1 calc PR A 1 C19 C 0.10716(14) 0.32827(15) 0.3681(3) 0.0280(6) Uani 1 1 d . . . H19 H 0.1369 0.3625 0.4371 0.034 Uiso 1 1 calc R . . C13 C -0.2665(2) 0.4489(2) 0.1438(4) 0.0236(7) Uiso 0.70 1 d P A 1 H13 H -0.2169 0.4792 0.1040 0.028 Uiso 0.70 1 calc PR A 1 C23' C -0.3678(7) 0.4647(7) 0.0711(14) 0.032(3) Uiso 0.30 1 d P A 2 H23D H -0.4040 0.4270 0.0175 0.048 Uiso 0.30 1 calc PR A 2 H23E H -0.3364 0.4931 -0.0126 0.048 Uiso 0.30 1 calc PR A 2 H23F H -0.4034 0.4995 0.1349 0.048 Uiso 0.30 1 calc PR A 2 C13' C -0.3052(5) 0.4254(5) 0.1852(10) 0.0277(18) Uiso 0.30 1 d P A 2 H13' H -0.3421 0.3955 0.2615 0.033 Uiso 0.30 1 calc PR A 2 C14' C -0.2531(6) 0.4776(5) 0.3003(11) 0.025(2) Uiso 0.30 1 d P A 2 H14C H -0.2899 0.5179 0.3457 0.030 Uiso 0.30 1 calc PR A 2 H14D H -0.2059 0.5016 0.2387 0.030 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 0.0381(4) 0.0376(4) 0.0636(4) -0.0034(3) -0.0102(4) 0.0134(3) Cl2 0.0439(4) 0.0553(5) 0.0337(3) -0.0007(3) -0.0043(3) -0.0186(3) Cl3 0.0394(3) 0.0447(5) 0.0481(4) -0.0005(3) 0.0084(3) -0.0091(3) C1G 0.0305(13) 0.0299(16) 0.0284(12) 0.0043(10) -0.0032(11) 0.0026(11) O3 0.0214(8) 0.0186(9) 0.0217(7) -0.0017(6) -0.0041(7) -0.0035(7) O2 0.0171(7) 0.0240(9) 0.0179(7) -0.0041(6) -0.0032(6) 0.0039(7) O1 0.0300(9) 0.0229(10) 0.0315(8) 0.0046(7) 0.0030(8) 0.0052(8) C3 0.0149(10) 0.0220(14) 0.0198(11) 0.0025(9) -0.0002(9) 0.0026(9) C6 0.0177(10) 0.0299(15) 0.0147(9) -0.0052(8) -0.0003(10) -0.0006(9) C7 0.0399(15) 0.0223(13) 0.0167(10) -0.0010(9) -0.0045(11) -0.0115(11) C22 0.0294(13) 0.0255(15) 0.0270(11) -0.0046(10) 0.0084(11) -0.0018(10) C5 0.0212(11) 0.0208(14) 0.0159(10) 0.0052(9) 0.0041(9) 0.0029(9) C2 0.0157(10) 0.0194(13) 0.0233(11) 0.0029(9) -0.0009(10) -0.0016(9) C17 0.0383(14) 0.0258(16) 0.0265(12) 0.0014(10) 0.0063(12) 0.0134(11) C18 0.0290(12) 0.0211(14) 0.0221(11) -0.0009(9) 0.0047(11) 0.0033(10) C8 0.0211(11) 0.0195(14) 0.0177(10) 0.0036(8) 0.0055(9) -0.0028(9) C21 0.0318(13) 0.0295(16) 0.0411(14) 0.0008(12) 0.0148(13) 0.0092(11) C16 0.0349(13) 0.0412(17) 0.0282(13) -0.0003(11) 0.0017(12) 0.0249(12) C20 0.0202(11) 0.0454(19) 0.0356(13) 0.0087(12) 0.0046(12) 0.0052(12) C1 0.0141(11) 0.0215(14) 0.0250(11) 0.0025(10) 0.0022(10) -0.0052(9) C10 0.0262(12) 0.0192(14) 0.0202(10) -0.0063(9) -0.0014(10) -0.0045(10) C9 0.0211(11) 0.0200(13) 0.0182(10) 0.0003(8) 0.0046(9) -0.0023(9) C15 0.0258(12) 0.0451(18) 0.0188(11) -0.0028(10) -0.0035(10) 0.0128(12) C4 0.0188(11) 0.0242(15) 0.0149(10) 0.0014(8) 0.0015(9) 0.0047(9) C11 0.0214(11) 0.0202(14) 0.0264(11) -0.0048(9) -0.0055(10) -0.0031(9) C12 0.0253(13) 0.0378(17) 0.0352(13) -0.0114(11) -0.0071(12) 0.0019(11) C19 0.0223(12) 0.0338(17) 0.0279(12) 0.0030(11) 0.0009(10) -0.0054(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1G 1.757(3) . ? Cl2 C1G 1.765(2) . ? Cl3 C1G 1.758(2) . ? O3 C8 1.368(3) . ? O3 C7 1.430(2) . ? O2 C5 1.378(3) . ? O2 C6 1.438(2) . ? O1 C1 1.220(3) . ? C3 C2 1.349(3) . ? C3 C4 1.464(3) . ? C6 C6 1.495(4) 2_565 ? C7 C7 1.488(5) 2_565 ? C22 C21 1.384(3) . ? C22 C9 1.386(3) . ? C5 C18 1.386(3) . ? C5 C4 1.411(3) . ? C2 C1 1.495(3) . ? C2 C14 1.506(4) . ? C2 C14' 1.555(8) . ? C17 C16 1.378(3) . ? C17 C18 1.384(3) . ? C8 C19 1.395(3) . ? C8 C9 1.402(3) . ? C21 C20 1.377(4) . ? C16 C15 1.380(3) . ? C20 C19 1.385(3) . ? C1 C11 1.493(3) . ? C10 C11 1.335(3) . ? C10 C9 1.488(3) . ? C15 C4 1.404(3) . ? C11 C12 1.506(3) . ? C14 C13 1.532(5) . ? C12 C13 1.489(4) . ? C12 C13' 1.491(8) . ? C23 C13 1.534(5) . ? C23' C13' 1.522(13) . ? C13' C14' 1.550(11) . ? 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 Cl1 C1G Cl3 110.30(14) . . ? Cl1 C1G Cl2 110.82(13) . . ? Cl3 C1G Cl2 110.25(13) . . ? C8 O3 C7 117.30(16) . . ? C5 O2 C6 117.22(17) . . ? C2 C3 C4 130.2(2) . . ? O2 C6 C6 107.37(16) . 2_565 ? O3 C7 C7 108.82(18) . 2_565 ? C21 C22 C9 121.8(2) . . ? O2 C5 C18 123.2(2) . . ? O2 C5 C4 115.10(19) . . ? C18 C5 C4 121.70(19) . . ? C3 C2 C1 115.93(19) . . ? C3 C2 C14 125.3(2) . . ? C1 C2 C14 118.7(2) . . ? C3 C2 C14' 126.7(4) . . ? C1 C2 C14' 114.4(4) . . ? C14 C2 C14' 18.5(3) . . ? C16 C17 C18 120.7(2) . . ? C17 C18 C5 119.3(2) . . ? O3 C8 C19 124.2(2) . . ? O3 C8 C9 116.04(18) . . ? C19 C8 C9 119.8(2) . . ? C20 C21 C22 119.6(2) . . ? C17 C16 C15 119.8(2) . . ? C21 C20 C19 120.0(2) . . ? O1 C1 C11 121.4(2) . . ? O1 C1 C2 121.80(19) . . ? C11 C1 C2 116.80(19) . . ? C11 C10 C9 128.52(18) . . ? C22 C9 C8 118.4(2) . . ? C22 C9 C10 119.58(19) . . ? C8 C9 C10 121.99(19) . . ? C16 C15 C4 121.8(2) . . ? C15 C4 C5 116.7(2) . . ? C15 C4 C3 124.2(2) . . ? C5 C4 C3 119.09(18) . . ? C10 C11 C1 122.8(2) . . ? C10 C11 C12 122.7(2) . . ? C1 C11 C12 114.5(2) . . ? C2 C14 C13 115.4(3) . . ? C13 C12 C13' 31.6(3) . . ? C13 C12 C11 109.5(2) . . ? C13' C12 C11 118.4(3) . . ? C20 C19 C8 120.5(2) . . ? C12 C13 C14 113.6(3) . . ? C12 C13 C23 111.0(3) . . ? C14 C13 C23 109.4(3) . . ? C12 C13' C23' 116.9(7) . . ? C12 C13' C14' 109.6(6) . . ? C23' C13' C14' 115.9(8) . . ? C13' C14' C2 107.3(6) . . ? 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 C5 O2 C6 C6 -178.85(18) . . . 2_565 ? C8 O3 C7 C7 176.61(18) . . . 2_565 ? C6 O2 C5 C18 6.3(3) . . . . ? C6 O2 C5 C4 -174.81(18) . . . . ? C4 C3 C2 C1 171.3(2) . . . . ? C4 C3 C2 C14 -10.8(4) . . . . ? C4 C3 C2 C14' 12.1(6) . . . . ? C16 C17 C18 C5 0.5(3) . . . . ? O2 C5 C18 C17 178.7(2) . . . . ? C4 C5 C18 C17 -0.1(3) . . . . ? C7 O3 C8 C19 -15.2(3) . . . . ? C7 O3 C8 C9 166.42(17) . . . . ? C9 C22 C21 C20 -1.3(3) . . . . ? C18 C17 C16 C15 0.3(4) . . . . ? C22 C21 C20 C19 0.0(3) . . . . ? C3 C2 C1 O1 19.6(3) . . . . ? C14 C2 C1 O1 -158.5(3) . . . . ? C14' C2 C1 O1 -178.6(4) . . . . ? C3 C2 C1 C11 -160.0(2) . . . . ? C14 C2 C1 C11 21.9(3) . . . . ? C14' C2 C1 C11 1.8(5) . . . . ? C21 C22 C9 C8 2.2(3) . . . . ? C21 C22 C9 C10 179.2(2) . . . . ? O3 C8 C9 C22 176.51(18) . . . . ? C19 C8 C9 C22 -1.9(3) . . . . ? O3 C8 C9 C10 -0.4(3) . . . . ? C19 C8 C9 C10 -178.86(19) . . . . ? C11 C10 C9 C22 132.8(3) . . . . ? C11 C10 C9 C8 -50.3(3) . . . . ? C17 C16 C15 C4 -1.5(4) . . . . ? C16 C15 C4 C5 1.8(3) . . . . ? C16 C15 C4 C3 -179.2(2) . . . . ? O2 C5 C4 C15 -179.91(19) . . . . ? C18 C5 C4 C15 -1.0(3) . . . . ? O2 C5 C4 C3 1.0(3) . . . . ? C18 C5 C4 C3 179.94(19) . . . . ? C2 C3 C4 C15 31.5(4) . . . . ? C2 C3 C4 C5 -149.6(2) . . . . ? C9 C10 C11 C1 -4.2(4) . . . . ? C9 C10 C11 C12 174.3(2) . . . . ? O1 C1 C11 C10 -40.3(3) . . . . ? C2 C1 C11 C10 139.4(2) . . . . ? O1 C1 C11 C12 141.2(2) . . . . ? C2 C1 C11 C12 -39.2(3) . . . . ? C3 C2 C14 C13 159.6(3) . . . . ? C1 C2 C14 C13 -22.5(4) . . . . ? C14' C2 C14 C13 58.6(12) . . . . ? C10 C11 C12 C13 -122.0(3) . . . . ? C1 C11 C12 C13 56.6(3) . . . . ? C10 C11 C12 C13' -155.3(5) . . . . ? C1 C11 C12 C13' 23.3(5) . . . . ? C21 C20 C19 C8 0.3(3) . . . . ? O3 C8 C19 C20 -177.6(2) . . . . ? C9 C8 C19 C20 0.7(3) . . . . ? C13' C12 C13 C14 55.6(6) . . . . ? C11 C12 C13 C14 -57.2(4) . . . . ? C13' C12 C13 C23 -68.2(6) . . . . ? C11 C12 C13 C23 179.0(3) . . . . ? C2 C14 C13 C12 41.0(5) . . . . ? C2 C14 C13 C23 165.7(3) . . . . ? C13 C12 C13' C23' 81.4(9) . . . . ? C11 C12 C13' C23' 162.4(6) . . . . ? C13 C12 C13' C14' -53.0(6) . . . . ? C11 C12 C13' C14' 28.0(8) . . . . ? C12 C13' C14' C2 -63.4(8) . . . . ? C23' C13' C14' C2 161.7(7) . . . . ? C3 C2 C14' C13' -151.6(5) . . . . ? C1 C2 C14' C13' 48.9(8) . . . . ? C14 C2 C14' C13' -59.0(11) . . . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.928 _refine_diff_density_max 0.256 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.054 # Attachment 'EEZZ-2_CHCl3.CIF' data_E,E,Z,Z_2_CHCl3 _database_code_depnum_ccdc_archive 'CCDC 757256' _audit_creation_method SHELXL-97 _chemical_name_systematic ;(1E,11E,16Z,27Z)-3,4:9,10:18,19:25,26-Tetrabenzo-5,8,20,24-tetraoxa- tricyclo[26.3.1.1(12,16)]tritriaconta-1,3,9,11,16,18,25,27-octaene-32,33-dione chloroform solvate ; _chemical_name_common ; (1E,11E,16Z,27Z)-3,4:9,10:18,19:25,26-Tetrabenzo-5,8,20,24- tetraoxa-tricyclo(26.3.1.1(12,16))tritriaconta-1,3,9,11,16,18,25,27- octaene-32,33-dione chloroform solvate ; _chemical_melting_point ? _chemical_formula_moiety '(C45 H42 O6)0.5 (C H Cl3)' _chemical_formula_sum 'C23.50 H22 Cl3 O3' _chemical_formula_weight 458.76 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/n' _symmetry_int_tables_number 13 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 15.2347(5) _cell_length_b 9.1731(3) _cell_length_c 16.4115(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.89(3) _cell_angle_gamma 90.00 _cell_volume 2292.25(14) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.422 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8495 _exptl_absorpt_correction_T_max 0.9591 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22762 _diffrn_reflns_av_R_equivalents 0.1152 _diffrn_reflns_av_sigmaI/netI 0.1597 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 28.31 _reflns_number_total 5042 _reflns_number_gt 1393 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius collect' _computing_cell_refinement 'Nonius collect' _computing_data_reduction 'Nonius collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-seed _computing_publication_material ciftab _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. Disordered phenolate moiety, C(10)-C(23)-C(22)-C(21)-C(20)-C(9)-O(3), was modelled over two positions with occupancy of 60 and 40 % for major and minor components, respectively. The chloroform molecule was highly disordered and was modelled over three positions. Appropriate DFIX restraints are applied to C-C bond lengths of disordered phenolate group. C-Cl Bond lengths of the disordered chloroform guest were restrained using a SADI card to be of equal lengths (+/- 0.03 A). Selected non-hydrogen atoms were refined isotropically, whereas non-hydrogen atoms of the Ar rings and the chloroform guest were refined anisotropically. Hydrogen atoms were inserted in geometrically determined positions with temperature factors fixed at 1.2 of the parent atom. ; _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^)+(0.2000P)^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 5042 _refine_ls_number_parameters 209 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.3581 _refine_ls_R_factor_gt 0.1515 _refine_ls_wR_factor_ref 0.4895 _refine_ls_wR_factor_gt 0.4033 _refine_ls_goodness_of_fit_ref 1.193 _refine_ls_restrained_S_all 1.211 _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 O1 O 0.1524(3) 0.9386(6) 0.0214(3) 0.0788(16) Uani 1 1 d . . . C1 C 0.0941(5) 0.8891(8) 0.0638(4) 0.064(2) Uani 1 1 d . A . C12 C 0.0364(4) 0.9829(9) 0.1121(4) 0.066(2) Uani 1 1 d . A . C2 C 0.0788(5) 0.7270(9) 0.0684(4) 0.072(2) Uani 1 1 d . . . C10 C 0.0236(6) 1.2418(10) 0.1670(6) 0.076(4) Uiso 0.65 1 d PG A 1 C9 C 0.0740(5) 1.3284(11) 0.2200(6) 0.081(4) Uiso 0.60 1 d PG A 1 C20 C 0.0337(6) 1.4325(10) 0.2677(6) 0.094(4) Uiso 0.60 1 d PG A 1 H20 H 0.0673 1.4905 0.3032 0.113 Uiso 0.60 1 calc PR A 1 C21 C -0.0570(7) 1.4500(11) 0.2623(6) 0.094(4) Uiso 0.60 1 d PG A 1 H21 H -0.0839 1.5196 0.2942 0.113 Uiso 0.60 1 calc PR A 1 C22 C -0.1073(5) 1.3634(12) 0.2093(7) 0.088(4) Uiso 0.60 1 d PG A 1 H22 H -0.1679 1.3751 0.2058 0.106 Uiso 0.60 1 calc PR A 1 C23 C -0.0670(6) 1.2593(11) 0.1617(6) 0.074(5) Uiso 0.60 1 d PG A 1 H23 H -0.1007 1.2013 0.1262 0.089 Uiso 0.60 1 calc PR A 1 C10A C 0.0039(5) 1.2227(11) 0.1774(7) 0.054(7) Uiso 0.35 1 d PG A 2 C9A C 0.0443(4) 1.3088(8) 0.2374(4) 0.071(5) Uiso 0.40 1 d PG A 2 C20A C -0.0043(4) 1.4120(11) 0.2785(5) 0.060(5) Uiso 0.40 1 d PG A 2 H20A H 0.0227 1.4696 0.3186 0.072 Uiso 0.40 1 calc PR A 2 C21A C -0.0933(4) 1.4291(14) 0.2595(8) 0.070(5) Uiso 0.40 1 d PG A 2 H21A H -0.1259 1.4982 0.2870 0.084 Uiso 0.40 1 calc PR A 2 C22A C -0.1337(4) 1.3430(15) 0.1995(8) 0.092(7) Uiso 0.40 1 d PG A 2 H22A H -0.1933 1.3545 0.1868 0.111 Uiso 0.40 1 calc PR A 2 C23A C -0.0851(5) 1.2398(15) 0.1584(8) 0.074(7) Uiso 0.40 1 d PG A 2 H23A H -0.1121 1.1822 0.1183 0.089 Uiso 0.40 1 calc PR A 2 O3 O 0.1594(4) 1.3262(8) 0.2126(5) 0.083(3) Uiso 0.60 1 d PG A 1 C8 C 0.2054(4) 1.4303(10) 0.2661(6) 0.152(4) Uiso 1 1 d G . 1 H8A H 0.2059 1.3981 0.3225 0.183 Uiso 1 1 calc R A 1 H8B H 0.1788 1.5262 0.2623 0.183 Uiso 1 1 calc R A 1 O3A O 0.1345(8) 1.2805(15) 0.2544(9) 0.087(4) Uiso 0.40 1 d P A 2 C11 C 0.0633(5) 1.1212(9) 0.1256(4) 0.075(2) Uani 1 1 d . . . H11 H 0.1175 1.1428 0.1041 0.090 Uiso 1 1 calc R A 1 C13 C -0.0454(5) 0.9211(9) 0.1444(6) 0.093(3) Uani 1 1 d . . . H13A H -0.0583 0.9712 0.1947 0.112 Uiso 1 1 calc R A . H13B H -0.0934 0.9407 0.1056 0.112 Uiso 1 1 calc R . . C4 C 0.2353(6) 0.6442(9) 0.0505(5) 0.083(2) Uani 1 1 d . . . C15 C -0.0124(5) 0.6821(9) 0.0865(6) 0.098(3) Uani 1 1 d . A . H15A H -0.0142 0.5779 0.0966 0.117 Uiso 1 1 calc R . . H15B H -0.0514 0.7034 0.0401 0.117 Uiso 1 1 calc R . . C14 C -0.0423(5) 0.7635(10) 0.1605(6) 0.095(3) Uani 1 1 d . A . H14A H -0.1002 0.7296 0.1746 0.114 Uiso 1 1 calc R . . H14B H -0.0022 0.7442 0.2064 0.114 Uiso 1 1 calc R . . C3 C 0.1426(6) 0.6316(9) 0.0584(4) 0.080(2) Uani 1 1 d . B 1 H3 H 0.1228 0.5357 0.0561 0.096 Uiso 1 1 calc R B 1 C7 C 0.2500 0.985(3) 0.2500 0.167(9) Uani 1 2 d S . . H7A H 0.2869 1.0478 0.2840 0.201 Uiso 0.50 1 calc PR . . H7B H 0.2131 1.0478 0.2160 0.201 Uiso 0.50 1 calc PR . . C1G C 0.3223(7) 1.0475(12) -0.0755(7) 0.156(4) Uiso 1 1 d D C 1 H1G H 0.2752 0.9762 -0.0684 0.187 Uiso 1 1 calc R C 1 Cl1 Cl 0.2880(4) 1.1980(7) -0.1410(4) 0.182(2) Uiso 0.70 1 d PD C 1 Cl4 Cl 0.267(2) 1.221(3) -0.083(3) 0.214(12) Uiso 0.15 1 d PD D 3 Cl5 Cl 0.3591(9) 0.9159(13) -0.1294(7) 0.215(4) Uiso 0.43 1 d PD E 2 Cl6 Cl 0.3310(13) 1.161(2) 0.0000(11) 0.277(10) Uiso 0.40 1 d PD C 1 Cl3 Cl 0.4273(6) 0.9601(10) -0.1105(5) 0.188(3) Uiso 0.50 1 d PD C 1 Cl8 Cl 0.2758(12) 1.054(3) -0.1742(11) 0.138(6) Uiso 0.15 1 d PD D 3 Cl7 Cl 0.3726(8) 1.1275(11) 0.0123(5) 0.148(3) Uiso 0.43 1 d PD F 4 C16 C 0.2745(7) 0.5518(12) -0.0064(7) 0.128(3) Uiso 1 1 d . B . H16 H 0.2396 0.4874 -0.0369 0.154 Uiso 1 1 calc R . . C5 C 0.2898(6) 0.7331(11) 0.0946(7) 0.091(3) Uani 1 1 d . B . C18 C 0.4133(8) 0.6469(14) 0.0233(8) 0.143(4) Uiso 1 1 d . B . H18 H 0.4728 0.6501 0.0124 0.171 Uiso 1 1 calc R . . C17 C 0.3647(9) 0.5555(16) -0.0174(8) 0.164(5) Uiso 1 1 d . . . H17 H 0.3899 0.4921 -0.0541 0.197 Uiso 1 1 calc R B . C19 C 0.3833(7) 0.7393(12) 0.0815(7) 0.125(3) Uiso 1 1 d . . . H19 H 0.4204 0.8022 0.1107 0.150 Uiso 1 1 calc R B . O2 O 0.2511(4) 0.8118(7) 0.1534(4) 0.107(2) Uani 1 1 d . . . C6 C 0.3036(8) 0.9099(14) 0.1998(7) 0.129(4) Uani 1 1 d . B . H6A H 0.3478 0.8569 0.2318 0.154 Uiso 1 1 calc R . . H6B H 0.3332 0.9769 0.1641 0.154 Uiso 1 1 calc R . . Cl9 Cl 0.4118(11) 1.083(2) -0.0203(12) 0.115(6) Uiso 0.15 1 d PD G 3 Cl2 Cl 0.2829(14) 0.940(3) -0.1706(12) 0.091(6) Uiso 0.10 1 d PD H 5 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 O1 0.081(3) 0.075(4) 0.081(4) -0.006(3) 0.007(3) 0.004(3) C1 0.065(4) 0.065(6) 0.060(5) 0.002(4) -0.012(4) -0.003(4) C12 0.063(4) 0.065(5) 0.069(5) -0.008(4) -0.007(4) 0.002(4) C2 0.089(6) 0.064(6) 0.062(5) -0.005(4) -0.014(4) -0.001(5) C11 0.065(4) 0.083(6) 0.076(5) -0.012(4) -0.005(4) 0.005(4) C13 0.087(6) 0.082(7) 0.112(7) 0.007(5) 0.018(5) 0.000(5) C4 0.115(7) 0.070(6) 0.064(5) -0.005(4) 0.001(5) 0.029(5) C15 0.086(6) 0.086(6) 0.118(7) 0.016(6) -0.023(5) -0.023(5) C14 0.087(6) 0.087(7) 0.112(8) 0.008(6) 0.021(5) -0.002(5) C3 0.090(6) 0.063(5) 0.086(6) -0.012(4) 0.005(4) -0.002(5) C7 0.18(2) 0.15(2) 0.16(2) 0.000 -0.096(18) 0.000 C5 0.086(6) 0.085(7) 0.103(7) 0.021(6) 0.007(6) 0.013(5) O2 0.095(4) 0.104(5) 0.121(5) -0.017(4) -0.044(4) -0.001(4) C6 0.180(12) 0.108(10) 0.094(8) 0.029(7) -0.046(9) -0.033(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.233(8) . ? C1 C12 1.479(10) . ? C1 C2 1.508(10) . ? C12 C11 1.349(10) . ? C12 C13 1.483(10) . ? C2 C3 1.322(10) . ? C2 C15 1.488(10) . ? C10 C9 1.3900 . ? C10 C23 1.3900 . ? C10 C11 1.442(10) . ? C9 O3 1.311(9) . ? C9 C20 1.3900 . ? C20 C21 1.3900 . ? C21 C22 1.3900 . ? C22 C23 1.3900 . ? C10A C9A 1.3900 . ? C10A C23A 1.3900 . ? C10A C11 1.568(11) . ? C9A C20A 1.3900 . ? C9A O3A 1.417(14) . ? C20A C21A 1.3900 . ? C21A C22A 1.3900 . ? C22A C23A 1.3900 . ? O3 C8 1.4612 . ? C8 C8 1.476(13) 2 ? C13 C14 1.470(11) . ? C4 C5 1.356(12) . ? C4 C16 1.407(12) . ? C4 C3 1.428(11) . ? C15 C14 1.509(11) . ? C7 C6 1.365(14) 2 ? C7 C6 1.365(14) . ? C1G Cl6 1.622(16) . ? C1G Cl1 1.815(12) . ? C1G Cl3 1.896(13) . ? Cl1 Cl6 2.41(2) . ? Cl4 Cl8 2.14(4) . ? C16 C17 1.393(14) . ? C5 O2 1.355(10) . ? C5 C19 1.449(12) . ? C18 C17 1.290(15) . ? C18 C19 1.366(14) . ? O2 C6 1.410(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C12 122.7(7) . . ? O1 C1 C2 120.5(7) . . ? C12 C1 C2 116.8(7) . . ? C11 C12 C1 116.9(6) . . ? C11 C12 C13 123.7(7) . . ? C1 C12 C13 119.4(7) . . ? C3 C2 C15 122.4(8) . . ? C3 C2 C1 122.0(7) . . ? C15 C2 C1 115.5(7) . . ? C9 C10 C23 120.0 . . ? C9 C10 C11 120.2(7) . . ? C23 C10 C11 119.3(7) . . ? O3 C9 C10 117.5(8) . . ? O3 C9 C20 121.4(8) . . ? C10 C9 C20 120.0 . . ? C21 C20 C9 120.0 . . ? C22 C21 C20 120.0 . . ? C21 C22 C23 120.0 . . ? C22 C23 C10 120.0 . . ? C9A C10A C23A 120.0 . . ? C9A C10A C11 118.2(4) . . ? C23A C10A C11 121.4(5) . . ? C10A C9A C20A 120.0 . . ? C10A C9A O3A 116.0(6) . . ? C20A C9A O3A 123.9(6) . . ? C21A C20A C9A 120.0 . . ? C22A C21A C20A 120.0 . . ? C21A C22A C23A 120.0 . . ? C22A C23A C10A 120.0 . . ? C9 O3 C8 113.0(6) . . ? O3 C8 C8 102.3(7) . 2 ? C12 C11 C10 132.0(8) . . ? C12 C11 C10A 118.0(7) . . ? C10 C11 C10A 14.1(6) . . ? C14 C13 C12 114.7(7) . . ? C5 C4 C16 116.9(10) . . ? C5 C4 C3 126.1(8) . . ? C16 C4 C3 117.0(9) . . ? C2 C15 C14 109.4(7) . . ? C13 C14 C15 110.5(7) . . ? C2 C3 C4 133.8(8) . . ? C6 C7 C6 119(2) 2 . ? Cl6 C1G Cl1 88.8(10) . . ? Cl6 C1G Cl3 117.0(10) . . ? Cl1 C1G Cl3 111.8(7) . . ? C1G Cl1 Cl6 42.3(5) . . ? C1G Cl6 Cl1 48.9(7) . . ? C17 C16 C4 120.8(11) . . ? O2 C5 C4 115.4(7) . . ? O2 C5 C19 122.5(10) . . ? C4 C5 C19 122.1(10) . . ? C17 C18 C19 124.4(13) . . ? C18 C17 C16 120.0(14) . . ? C18 C19 C5 115.7(11) . . ? C5 O2 C6 118.2(9) . . ? C7 C6 O2 107.9(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C12 C11 -16.7(9) . . . . ? C2 C1 C12 C11 163.2(6) . . . . ? O1 C1 C12 C13 164.6(7) . . . . ? C2 C1 C12 C13 -15.5(9) . . . . ? O1 C1 C2 C3 28.5(10) . . . . ? C12 C1 C2 C3 -151.4(7) . . . . ? O1 C1 C2 C15 -152.6(7) . . . . ? C12 C1 C2 C15 27.4(9) . . . . ? C23 C10 C9 O3 -168.2(9) . . . . ? C11 C10 C9 O3 20.0(9) . . . . ? C23 C10 C9 C20 0.0 . . . . ? C11 C10 C9 C20 -171.8(9) . . . . ? O3 C9 C20 C21 167.7(10) . . . . ? C10 C9 C20 C21 0.0 . . . . ? C9 C20 C21 C22 0.0 . . . . ? C20 C21 C22 C23 0.0 . . . . ? C21 C22 C23 C10 0.0 . . . . ? C9 C10 C23 C22 0.0 . . . . ? C11 C10 C23 C22 171.9(9) . . . . ? C23A C10A C9A C20A 0.0 . . . . ? C11 C10A C9A C20A 172.8(9) . . . . ? C23A C10A C9A O3A 178.0(6) . . . . ? C11 C10A C9A O3A -9.2(11) . . . . ? C10A C9A C20A C21A 0.0 . . . . ? O3A C9A C20A C21A -177.9(7) . . . . ? C9A C20A C21A C22A 0.0 . . . . ? C20A C21A C22A C23A 0.0 . . . . ? C21A C22A C23A C10A 0.0 . . . . ? C9A C10A C23A C22A 0.0 . . . . ? C11 C10A C23A C22A -172.6(10) . . . . ? C10 C9 O3 C8 174.9(7) . . . . ? C20 C9 O3 C8 6.9(11) . . . . ? C9 O3 C8 C8 -167.9(9) . . . 2 ? C1 C12 C11 C10 177.9(8) . . . . ? C13 C12 C11 C10 -3.5(13) . . . . ? C1 C12 C11 C10A -179.4(7) . . . . ? C13 C12 C11 C10A -0.8(11) . . . . ? C9 C10 C11 C12 136.0(8) . . . . ? C23 C10 C11 C12 -35.9(12) . . . . ? C9 C10 C11 C10A 126(3) . . . . ? C23 C10 C11 C10A -46(3) . . . . ? C9A C10A C11 C12 135.3(7) . . . . ? C23A C10A C11 C12 -52.0(8) . . . . ? C9A C10A C11 C10 -53(2) . . . . ? C23A C10A C11 C10 120(3) . . . . ? C11 C12 C13 C14 -150.2(8) . . . . ? C1 C12 C13 C14 28.4(11) . . . . ? C3 C2 C15 C14 128.2(8) . . . . ? C1 C2 C15 C14 -50.7(9) . . . . ? C12 C13 C14 C15 -51.9(10) . . . . ? C2 C15 C14 C13 63.0(9) . . . . ? C15 C2 C3 C4 -171.3(8) . . . . ? C1 C2 C3 C4 7.4(13) . . . . ? C5 C4 C3 C2 42.2(14) . . . . ? C16 C4 C3 C2 -140.4(10) . . . . ? Cl3 C1G Cl1 Cl6 -118.7(11) . . . . ? Cl3 C1G Cl6 Cl1 114.0(10) . . . . ? C5 C4 C16 C17 -1.6(14) . . . . ? C3 C4 C16 C17 -179.2(9) . . . . ? C16 C4 C5 O2 -174.7(7) . . . . ? C3 C4 C5 O2 2.7(12) . . . . ? C16 C4 C5 C19 3.2(12) . . . . ? C3 C4 C5 C19 -179.4(8) . . . . ? C19 C18 C17 C16 3(2) . . . . ? C4 C16 C17 C18 -1.7(18) . . . . ? C17 C18 C19 C5 -1.7(18) . . . . ? O2 C5 C19 C18 176.1(9) . . . . ? C4 C5 C19 C18 -1.8(14) . . . . ? C4 C5 O2 C6 -178.0(8) . . . . ? C19 C5 O2 C6 4.0(12) . . . . ? C6 C7 C6 O2 54.0(7) 2 . . . ? C5 O2 C6 C7 175.1(11) . . . . ? _diffrn_measured_fraction_theta_max 0.884 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.884 _refine_diff_density_max 0.745 _refine_diff_density_min -0.532 _refine_diff_density_rms 0.081