# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Cammidge, A.N.' 'Zhang, Liang' 'Gopee, Hemant' 'Hughes, David' _publ_contact_author_name 'Cammidge, A.N.' _publ_contact_author_email A.CAMMIDGE@UEA.AC.UK _publ_section_title ; Antiaromatic twinned triphenylene discotics showing nematic phases and 2-dimensional pi-overlap in the solid state. ; # Attachment 'chemcomm.txt' data_09src1148 _database_code_depnum_ccdc_archive 'CCDC 769122' #TrackingRef 'chemcomm.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_structural bis-(tetrahexoxy-triphenylenyl-tetradiynyl) _chemical_formula_moiety 'C92 H116 O8' _chemical_formula_sum 'C92 H116 O8' _chemical_formula_weight 1349.85 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 Monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.8608(6) _cell_length_b 27.2688(16) _cell_length_c 16.3205(12) _cell_angle_alpha 90.00 _cell_angle_beta 95.592(2) _cell_angle_gamma 90.00 _cell_volume 3924.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.806 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 4096x4096pixels/62x62mm _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21077 _diffrn_reflns_av_R_equivalents 0.0697 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 22.50 _reflns_number_total 5106 _reflns_number_gt 3735 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' # Although determined using DirAx, the cell is refined in the HKL # package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP (Johnson, 1971 and Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0239P)^2^+5.0862P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5106 _refine_ls_number_parameters 479 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0996 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.1411 _refine_ls_wR_factor_gt 0.1278 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.126 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4442(3) 0.33936(11) 0.44152(19) 0.0209(7) Uani 1 1 d . . . C11 C 0.5304(3) 0.36890(11) 0.4983(2) 0.0228(8) Uani 1 1 d . . . H11 H 0.5193 0.4027 0.4938 0.027 Uiso 1 1 calc R . . C12 C 0.6307(3) 0.35062(10) 0.56069(19) 0.0214(8) Uani 1 1 d . . . C13 C 0.7064(4) 0.38561(11) 0.6157(2) 0.0223(8) Uani 1 1 d . . . C14 C 0.7471(3) 0.42332(11) 0.6494(2) 0.0245(8) Uani 1 1 d . . . C2 C 0.4596(3) 0.28773(10) 0.4494(2) 0.0210(7) Uani 1 1 d . . . C21 C 0.5653(3) 0.26894(10) 0.51247(19) 0.0206(7) Uani 1 1 d . . . H21 H 0.5784 0.2352 0.5172 0.025 Uiso 1 1 calc R . . C22 C 0.6489(3) 0.29926(11) 0.56687(19) 0.0223(8) Uani 1 1 d . . . O23 O 0.7526(2) 0.28464(7) 0.62959(14) 0.0282(6) Uani 1 1 d . . . C24 C 0.7735(4) 0.23299(11) 0.6461(2) 0.0263(8) Uani 1 1 d . B . H24A H 0.8136 0.2167 0.6000 0.032 Uiso 1 1 calc R . . H24B H 0.6780 0.2177 0.6558 0.032 Uiso 1 1 calc R . . C25 C 0.8847(4) 0.22980(12) 0.7221(2) 0.0363(9) Uani 1 1 d . . . H25A H 0.9804 0.2439 0.7097 0.044 Uiso 1 1 calc R A 1 H25B H 0.8469 0.2495 0.7652 0.044 Uiso 1 1 calc R A 1 C26 C 0.9137(4) 0.17847(13) 0.7544(2) 0.0413(10) Uani 0.545(16) 1 d P B 1 H26A H 0.9172 0.1564 0.7080 0.050 Uiso 0.545(16) 1 calc PR B 1 H26B H 0.8292 0.1686 0.7842 0.050 Uiso 0.545(16) 1 calc PR B 1 C27 C 1.0622(15) 0.1727(3) 0.8119(7) 0.042(3) Uani 0.545(16) 1 d P B 1 H27A H 1.0714 0.1390 0.8310 0.050 Uiso 0.545(16) 1 calc PR B 1 H27B H 1.1481 0.1798 0.7814 0.050 Uiso 0.545(16) 1 calc PR B 1 C28 C 1.0649(16) 0.2064(5) 0.8848(7) 0.050(3) Uani 0.545(16) 1 d P B 1 H28A H 0.9716 0.2029 0.9107 0.060 Uiso 0.545(16) 1 calc PR B 1 H28B H 1.0722 0.2401 0.8667 0.060 Uiso 0.545(16) 1 calc PR B 1 C29 C 1.199(4) 0.1943(11) 0.946(2) 0.066(9) Uani 0.545(16) 1 d P B 1 H29A H 1.2020 0.2169 0.9913 0.099 Uiso 0.545(16) 1 calc PR B 1 H29B H 1.2905 0.1969 0.9197 0.099 Uiso 0.545(16) 1 calc PR B 1 H29C H 1.1882 0.1615 0.9660 0.099 Uiso 0.545(16) 1 calc PR B 1 C26A C 0.9137(4) 0.17847(13) 0.7544(2) 0.0413(10) Uani 0.455(16) 1 d P B 2 H26C H 0.9857 0.1623 0.7223 0.050 Uiso 0.455(16) 1 calc PR B 2 H26D H 0.8198 0.1600 0.7482 0.050 Uiso 0.455(16) 1 calc PR B 2 C27A C 0.9787(16) 0.1788(4) 0.8488(8) 0.040(4) Uani 0.455(16) 1 d P B 2 H27C H 0.9136 0.1984 0.8802 0.047 Uiso 0.455(16) 1 calc PR B 2 H27D H 0.9804 0.1456 0.8703 0.047 Uiso 0.455(16) 1 calc PR B 2 C28A C 1.1368(18) 0.1997(4) 0.8575(9) 0.041(4) Uani 0.455(16) 1 d P B 2 H28C H 1.1334 0.2327 0.8354 0.049 Uiso 0.455(16) 1 calc PR B 2 H28D H 1.1998 0.1801 0.8246 0.049 Uiso 0.455(16) 1 calc PR B 2 C29A C 1.213(5) 0.2013(12) 0.949(3) 0.047(7) Uani 0.455(16) 1 d P B 2 H29D H 1.3150 0.2136 0.9489 0.071 Uiso 0.455(16) 1 calc PR B 2 H29E H 1.2160 0.1689 0.9715 0.071 Uiso 0.455(16) 1 calc PR B 2 H29F H 1.1561 0.2225 0.9809 0.071 Uiso 0.455(16) 1 calc PR B 2 C3 C 0.3646(3) 0.25638(10) 0.39249(19) 0.0214(8) Uani 1 1 d . . . C31 C 0.3744(3) 0.20449(11) 0.3974(2) 0.0230(8) Uani 1 1 d . . . H31 H 0.4417 0.1902 0.4378 0.028 Uiso 1 1 calc R . . C32 C 0.2868(3) 0.17503(10) 0.34405(19) 0.0222(8) Uani 1 1 d . . . O33 O 0.2886(2) 0.12484(7) 0.34415(13) 0.0259(6) Uani 1 1 d . . . C34 C 0.3881(4) 0.10066(10) 0.4061(2) 0.0238(8) Uani 1 1 d . . . H34A H 0.3565 0.1072 0.4603 0.029 Uiso 1 1 calc R . . H34B H 0.4911 0.1124 0.4046 0.029 Uiso 1 1 calc R . . C35 C 0.3798(4) 0.04636(10) 0.3881(2) 0.0241(8) Uani 1 1 d . . . H35A H 0.4587 0.0300 0.4234 0.029 Uiso 1 1 calc R . . H35B H 0.4015 0.0412 0.3316 0.029 Uiso 1 1 calc R . . C36 C 0.2289(4) 0.02213(11) 0.4000(2) 0.0287(8) Uani 1 1 d . . . H36A H 0.1486 0.0387 0.3660 0.034 Uiso 1 1 calc R . . H36B H 0.2083 0.0256 0.4570 0.034 Uiso 1 1 calc R . . C37 C 0.2284(4) -0.03252(11) 0.3773(2) 0.0296(8) Uani 1 1 d . . . H37A H 0.1279 -0.0457 0.3819 0.036 Uiso 1 1 calc R . . H37B H 0.2491 -0.0356 0.3202 0.036 Uiso 1 1 calc R . . C38 C 0.3431(4) -0.06310(11) 0.4304(2) 0.0303(9) Uani 1 1 d . . . H38A H 0.4436 -0.0497 0.4267 0.036 Uiso 1 1 calc R . . H38B H 0.3212 -0.0607 0.4873 0.036 Uiso 1 1 calc R . . C39 C 0.3424(4) -0.11660(11) 0.4054(2) 0.0406(10) Uani 1 1 d . . . H39A H 0.4164 -0.1342 0.4409 0.061 Uiso 1 1 calc R . . H39B H 0.3665 -0.1193 0.3495 0.061 Uiso 1 1 calc R . . H39C H 0.2437 -0.1303 0.4100 0.061 Uiso 1 1 calc R . . C4 C 0.2620(3) 0.27745(10) 0.33145(19) 0.0204(7) Uani 1 1 d . . . C41 C 0.1734(3) 0.24608(11) 0.2771(2) 0.0229(8) Uani 1 1 d . . . H41 H 0.1047 0.2598 0.2367 0.028 Uiso 1 1 calc R . . C42 C 0.1856(4) 0.19613(11) 0.2820(2) 0.0231(8) Uani 1 1 d . . . O43 O 0.1053(2) 0.16382(7) 0.23063(13) 0.0265(6) Uani 1 1 d . . . C44 C 0.0000(4) 0.18364(11) 0.1668(2) 0.0250(8) Uani 1 1 d . . . H44A H 0.0523 0.2053 0.1319 0.030 Uiso 1 1 calc R . . H44B H -0.0778 0.2023 0.1908 0.030 Uiso 1 1 calc R . . C45 C -0.0706(4) 0.14171(11) 0.1171(2) 0.0277(8) Uani 1 1 d . . . H45A H -0.1110 0.1182 0.1538 0.033 Uiso 1 1 calc R . . H45B H 0.0068 0.1253 0.0890 0.033 Uiso 1 1 calc R . . C46 C -0.1973(4) 0.15877(11) 0.0538(2) 0.0281(8) Uani 1 1 d . . . H46A H -0.2804 0.1711 0.0825 0.034 Uiso 1 1 calc R . . H46B H -0.1602 0.1857 0.0225 0.034 Uiso 1 1 calc R . . C47 C -0.2569(4) 0.11860(13) -0.0054(2) 0.0380(9) Uani 1 1 d . . . H47A H -0.1736 0.1062 -0.0338 0.046 Uiso 1 1 calc R . . H47B H -0.2943 0.0918 0.0260 0.046 Uiso 1 1 calc R . . C48 C -0.3829(4) 0.13543(14) -0.0690(2) 0.0458(10) Uani 1 1 d . . . H48A H -0.3478 0.1636 -0.0981 0.055 Uiso 1 1 calc R . . H48B H -0.4689 0.1458 -0.0408 0.055 Uiso 1 1 calc R . . C49 C -0.4348(5) 0.09581(17) -0.1314(3) 0.0682(14) Uani 1 1 d . . . H49A H -0.5142 0.1085 -0.1698 0.102 Uiso 1 1 calc R . . H49B H -0.4720 0.0681 -0.1032 0.102 Uiso 1 1 calc R . . H49C H -0.3508 0.0859 -0.1605 0.102 Uiso 1 1 calc R . . C5 C 0.2473(3) 0.33074(11) 0.32326(19) 0.0208(7) Uani 1 1 d . . . C51 C 0.1447(3) 0.35298(11) 0.2623(2) 0.0228(8) Uani 1 1 d . . . H51 H 0.0841 0.3332 0.2262 0.027 Uiso 1 1 calc R . . C52 C 0.1327(3) 0.40316(11) 0.25501(19) 0.0211(7) Uani 1 1 d . . . O53 O 0.0358(2) 0.42696(7) 0.19818(13) 0.0258(5) Uani 1 1 d . . . C54 C -0.0727(4) 0.39800(11) 0.1476(2) 0.0283(8) Uani 1 1 d . . . H54A H -0.1272 0.3764 0.1816 0.034 Uiso 1 1 calc R . . H54B H -0.0215 0.3781 0.1095 0.034 Uiso 1 1 calc R . . C55 C -0.1813(4) 0.43323(11) 0.10091(19) 0.0255(8) Uani 1 1 d . . . H55A H -0.2482 0.4149 0.0614 0.031 Uiso 1 1 calc R . . H55B H -0.1239 0.4560 0.0704 0.031 Uiso 1 1 calc R . . C56 C -0.2769(4) 0.46220(12) 0.1565(2) 0.0314(9) Uani 1 1 d . . . H56A H -0.2119 0.4852 0.1887 0.038 Uiso 1 1 calc R . . H56B H -0.3184 0.4398 0.1946 0.038 Uiso 1 1 calc R . . C57 C -0.4064(4) 0.49034(12) 0.1100(2) 0.0312(9) Uani 1 1 d . . . H57A H -0.3647 0.5130 0.0723 0.037 Uiso 1 1 calc R . . H57B H -0.4708 0.4674 0.0774 0.037 Uiso 1 1 calc R . . C58 C -0.5026(4) 0.51880(15) 0.1651(2) 0.0459(10) Uani 1 1 d . . . H58A H -0.4420 0.5450 0.1917 0.055 Uiso 1 1 calc R . . H58B H -0.5325 0.4971 0.2078 0.055 Uiso 1 1 calc R . . C59 C -0.6449(4) 0.54095(15) 0.1191(2) 0.0516(11) Uani 1 1 d . . . H59A H -0.7007 0.5586 0.1571 0.077 Uiso 1 1 calc R . . H59B H -0.7071 0.5152 0.0939 0.077 Uiso 1 1 calc R . . H59C H -0.6163 0.5629 0.0773 0.077 Uiso 1 1 calc R . . C6 C 0.3394(3) 0.36087(10) 0.37685(19) 0.0206(8) Uani 1 1 d . . . C61 C 0.3256(3) 0.41191(11) 0.3674(2) 0.0232(8) Uani 1 1 d . . . H61 H 0.3872 0.4320 0.4025 0.028 Uiso 1 1 calc R . . C62 C 0.2248(3) 0.43364(10) 0.30841(19) 0.0215(8) Uani 1 1 d . . . C63 C 0.2146(3) 0.48620(12) 0.3086(2) 0.0239(8) Uani 1 1 d . . . C64 C 0.7758(4) 0.47038(11) 0.6765(2) 0.0247(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0208(18) 0.0188(17) 0.0239(19) -0.0014(14) 0.0062(15) -0.0008(14) C11 0.0231(18) 0.0113(16) 0.034(2) -0.0018(14) 0.0047(16) 0.0004(14) C12 0.0205(18) 0.0162(17) 0.028(2) -0.0001(14) 0.0052(15) 0.0002(14) C13 0.0233(18) 0.0177(18) 0.0258(19) 0.0026(16) 0.0016(15) 0.0021(15) C14 0.0249(19) 0.020(2) 0.028(2) 0.0034(16) -0.0013(15) 0.0021(15) C2 0.0200(17) 0.0155(17) 0.0280(19) 0.0008(14) 0.0043(15) 0.0000(14) C21 0.0224(18) 0.0115(16) 0.0284(19) 0.0005(14) 0.0050(15) 0.0006(14) C22 0.0204(18) 0.0225(18) 0.0240(19) 0.0042(15) 0.0025(15) 0.0031(14) O23 0.0336(14) 0.0137(11) 0.0353(14) 0.0015(10) -0.0073(11) 0.0004(10) C24 0.031(2) 0.0168(17) 0.032(2) 0.0027(14) 0.0048(16) 0.0020(15) C25 0.039(2) 0.0253(19) 0.042(2) 0.0035(17) -0.0060(18) -0.0025(16) C26 0.047(2) 0.029(2) 0.045(2) 0.0082(18) -0.009(2) -0.0016(18) C27 0.048(7) 0.026(4) 0.050(6) 0.011(4) -0.009(5) 0.004(4) C28 0.047(7) 0.070(7) 0.034(6) 0.002(5) 0.003(5) 0.003(6) C29 0.052(10) 0.097(19) 0.043(11) 0.010(11) -0.017(8) -0.030(10) C26A 0.047(2) 0.029(2) 0.045(2) 0.0082(18) -0.009(2) -0.0016(18) C27A 0.032(7) 0.032(5) 0.055(8) 0.010(5) 0.006(6) -0.003(5) C28A 0.039(8) 0.041(6) 0.042(8) 0.005(5) 0.004(6) 0.004(6) C29A 0.050(14) 0.022(6) 0.066(17) 0.019(7) -0.010(12) 0.000(8) C3 0.0201(18) 0.0135(16) 0.031(2) 0.0002(14) 0.0029(15) -0.0024(14) C31 0.0198(18) 0.0188(17) 0.030(2) 0.0021(15) -0.0014(15) 0.0008(14) C32 0.0258(19) 0.0142(17) 0.027(2) -0.0006(14) 0.0039(16) 0.0005(14) O33 0.0309(13) 0.0120(12) 0.0336(14) -0.0003(9) -0.0033(11) 0.0017(10) C34 0.0267(19) 0.0178(17) 0.026(2) 0.0021(14) 0.0001(15) 0.0015(14) C35 0.0278(19) 0.0172(17) 0.0272(19) -0.0003(14) 0.0016(15) 0.0045(14) C36 0.027(2) 0.0214(18) 0.037(2) 0.0050(15) 0.0006(16) -0.0009(15) C37 0.030(2) 0.0211(17) 0.037(2) 0.0008(15) -0.0007(16) -0.0070(15) C38 0.035(2) 0.0171(17) 0.037(2) 0.0012(15) -0.0013(17) -0.0020(15) C39 0.046(2) 0.0211(19) 0.053(3) 0.0000(17) -0.004(2) -0.0012(17) C4 0.0233(18) 0.0160(17) 0.0227(19) -0.0022(14) 0.0062(15) 0.0016(14) C41 0.0218(18) 0.0184(18) 0.029(2) 0.0024(14) 0.0035(15) 0.0005(14) C42 0.0256(19) 0.0181(18) 0.026(2) -0.0052(15) 0.0047(16) -0.0047(15) O43 0.0309(13) 0.0169(11) 0.0301(14) -0.0020(10) -0.0059(11) -0.0006(10) C44 0.0245(19) 0.0228(17) 0.027(2) 0.0005(15) 0.0002(16) -0.0016(14) C45 0.0261(19) 0.0224(18) 0.034(2) -0.0015(16) 0.0000(16) 0.0005(15) C46 0.0267(19) 0.0286(19) 0.029(2) -0.0026(16) 0.0039(16) 0.0026(15) C47 0.036(2) 0.036(2) 0.040(2) -0.0084(17) -0.0071(18) -0.0031(17) C48 0.037(2) 0.059(3) 0.040(2) -0.008(2) -0.0050(19) -0.001(2) C49 0.056(3) 0.083(3) 0.060(3) -0.011(3) -0.022(2) -0.013(3) C5 0.0214(18) 0.0185(17) 0.0233(19) 0.0016(14) 0.0056(15) 0.0007(14) C51 0.0242(18) 0.0176(18) 0.027(2) -0.0062(14) 0.0024(15) -0.0024(14) C52 0.0232(18) 0.0181(17) 0.0224(19) 0.0000(14) 0.0033(15) 0.0019(14) O53 0.0308(13) 0.0166(11) 0.0283(13) 0.0001(10) -0.0058(11) -0.0018(10) C54 0.034(2) 0.0212(17) 0.029(2) -0.0061(15) -0.0008(16) -0.0031(15) C55 0.0277(19) 0.0239(18) 0.0234(19) 0.0001(15) -0.0043(15) 0.0020(15) C56 0.035(2) 0.0280(19) 0.030(2) 0.0006(16) -0.0045(17) 0.0040(16) C57 0.033(2) 0.0314(19) 0.028(2) 0.0009(16) -0.0023(16) 0.0008(16) C58 0.041(2) 0.055(3) 0.041(2) 0.010(2) 0.0015(19) 0.020(2) C59 0.048(3) 0.063(3) 0.042(3) -0.002(2) -0.003(2) 0.023(2) C6 0.0217(18) 0.0158(17) 0.0243(19) -0.0003(14) 0.0028(15) 0.0001(14) C61 0.0203(18) 0.0191(17) 0.030(2) -0.0054(15) -0.0006(15) -0.0029(14) C62 0.0232(18) 0.0134(17) 0.028(2) 0.0009(14) 0.0032(15) -0.0009(14) C63 0.0168(18) 0.025(2) 0.028(2) 0.0011(15) -0.0031(14) -0.0011(14) C64 0.0246(19) 0.018(2) 0.030(2) 0.0035(15) -0.0032(15) -0.0021(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C11 1.398(4) . ? C1 C2 1.419(4) . ? C1 C6 1.459(4) . ? C11 C12 1.378(4) . ? C11 H11 0.9300 . ? C12 C22 1.412(4) . ? C12 C13 1.431(4) . ? C13 C14 1.205(4) . ? C14 C64 1.373(5) . ? C2 C21 1.418(4) . ? C2 C3 1.466(4) . ? C21 C22 1.376(4) . ? C21 H21 0.9300 . ? C22 O23 1.366(4) . ? O23 C24 1.443(3) . ? C24 C25 1.510(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.509(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.548(9) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.50(2) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.51(3) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C27A C28A 1.51(2) . ? C27A H27C 0.9700 . ? C27A H27D 0.9700 . ? C28A C29A 1.57(4) . ? C28A H28C 0.9700 . ? C28A H28D 0.9700 . ? C29A H29D 0.9600 . ? C29A H29E 0.9600 . ? C29A H29F 0.9600 . ? C3 C4 1.405(4) . ? C3 C31 1.420(4) . ? C31 C32 1.369(4) . ? C31 H31 0.9300 . ? C32 O33 1.369(3) . ? C32 C42 1.409(4) . ? O33 C34 1.436(3) . ? C34 C35 1.510(4) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.521(4) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.536(4) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.519(4) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.515(4) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C4 C41 1.415(4) . ? C4 C5 1.464(4) . ? C41 C42 1.368(4) . ? C41 H41 0.9300 . ? C42 O43 1.367(4) . ? O43 C44 1.434(4) . ? C44 C45 1.503(4) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 C46 1.522(4) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 C47 1.521(4) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 C48 1.519(5) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 C49 1.525(5) . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? C49 H49A 0.9600 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? C5 C6 1.403(4) . ? C5 C51 1.417(4) . ? C51 C52 1.377(4) . ? C51 H51 0.9300 . ? C52 O53 1.365(4) . ? C52 C62 1.407(4) . ? O53 C54 1.440(4) . ? C54 C55 1.512(4) . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? C55 C56 1.521(5) . ? C55 H55A 0.9700 . ? C55 H55B 0.9700 . ? C56 C57 1.521(4) . ? C56 H56A 0.9700 . ? C56 H56B 0.9700 . ? C57 C58 1.512(5) . ? C57 H57A 0.9700 . ? C57 H57B 0.9700 . ? C58 C59 1.528(5) . ? C58 H58A 0.9700 . ? C58 H58B 0.9700 . ? C59 H59A 0.9600 . ? C59 H59B 0.9600 . ? C59 H59C 0.9600 . ? C6 C61 1.405(4) . ? C61 C62 1.381(4) . ? C61 H61 0.9300 . ? C62 C63 1.436(4) . ? C63 C64 1.210(4) 3_666 ? C64 C63 1.210(4) 3_666 ? 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 C11 C1 C2 118.1(3) . . ? C11 C1 C6 121.1(3) . . ? C2 C1 C6 120.9(3) . . ? C12 C11 C1 123.6(3) . . ? C12 C11 H11 118.2 . . ? C1 C11 H11 118.2 . . ? C11 C12 C22 118.2(3) . . ? C11 C12 C13 116.8(3) . . ? C22 C12 C13 125.0(3) . . ? C14 C13 C12 163.0(3) . . ? C13 C14 C64 169.3(3) . . ? C21 C2 C1 118.3(3) . . ? C21 C2 C3 123.1(3) . . ? C1 C2 C3 118.5(3) . . ? C22 C21 C2 121.8(3) . . ? C22 C21 H21 119.1 . . ? C2 C21 H21 119.1 . . ? O23 C22 C21 126.1(3) . . ? O23 C22 C12 114.0(3) . . ? C21 C22 C12 120.0(3) . . ? C22 O23 C24 119.3(2) . . ? O23 C24 C25 105.8(2) . . ? O23 C24 H24A 110.6 . . ? C25 C24 H24A 110.6 . . ? O23 C24 H24B 110.6 . . ? C25 C24 H24B 110.6 . . ? H24A C24 H24B 108.7 . . ? C26 C25 C24 114.6(3) . . ? C26 C25 H25A 108.6 . . ? C24 C25 H25A 108.6 . . ? C26 C25 H25B 108.6 . . ? C24 C25 H25B 108.6 . . ? H25A C25 H25B 107.6 . . ? C25 C26 C27 114.3(4) . . ? C25 C26 H26A 108.7 . . ? C27 C26 H26A 108.7 . . ? C25 C26 H26B 108.7 . . ? C27 C26 H26B 108.7 . . ? H26A C26 H26B 107.6 . . ? C28 C27 C26 111.4(11) . . ? C28 C27 H27A 109.3 . . ? C26 C27 H27A 109.3 . . ? C28 C27 H27B 109.3 . . ? C26 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? C27 C28 C29 110.0(18) . . ? C27 C28 H28A 109.7 . . ? C29 C28 H28A 109.7 . . ? C27 C28 H28B 109.7 . . ? C29 C28 H28B 109.7 . . ? H28A C28 H28B 108.2 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28A C27A H27C 109.7 . . ? C28A C27A H27D 109.7 . . ? H27C C27A H27D 108.2 . . ? C27A C28A C29A 114(2) . . ? C27A C28A H28C 108.7 . . ? C29A C28A H28C 108.7 . . ? C27A C28A H28D 108.7 . . ? C29A C28A H28D 108.7 . . ? H28C C28A H28D 107.6 . . ? C28A C29A H29D 109.5 . . ? C28A C29A H29E 109.5 . . ? H29D C29A H29E 109.5 . . ? C28A C29A H29F 109.5 . . ? H29D C29A H29F 109.5 . . ? H29E C29A H29F 109.5 . . ? C4 C3 C31 118.7(3) . . ? C4 C3 C2 120.2(3) . . ? C31 C3 C2 121.1(3) . . ? C32 C31 C3 121.4(3) . . ? C32 C31 H31 119.3 . . ? C3 C31 H31 119.3 . . ? O33 C32 C31 125.5(3) . . ? O33 C32 C42 114.6(3) . . ? C31 C32 C42 120.0(3) . . ? C32 O33 C34 117.8(2) . . ? O33 C34 C35 107.4(2) . . ? O33 C34 H34A 110.2 . . ? C35 C34 H34A 110.2 . . ? O33 C34 H34B 110.2 . . ? C35 C34 H34B 110.2 . . ? H34A C34 H34B 108.5 . . ? C34 C35 C36 115.3(3) . . ? C34 C35 H35A 108.4 . . ? C36 C35 H35A 108.4 . . ? C34 C35 H35B 108.4 . . ? C36 C35 H35B 108.4 . . ? H35A C35 H35B 107.5 . . ? C35 C36 C37 111.9(3) . . ? C35 C36 H36A 109.2 . . ? C37 C36 H36A 109.2 . . ? C35 C36 H36B 109.2 . . ? C37 C36 H36B 109.2 . . ? H36A C36 H36B 107.9 . . ? C38 C37 C36 114.1(3) . . ? C38 C37 H37A 108.7 . . ? C36 C37 H37A 108.7 . . ? C38 C37 H37B 108.7 . . ? C36 C37 H37B 108.7 . . ? H37A C37 H37B 107.6 . . ? C39 C38 C37 113.0(3) . . ? C39 C38 H38A 109.0 . . ? C37 C38 H38A 109.0 . . ? C39 C38 H38B 109.0 . . ? C37 C38 H38B 109.0 . . ? H38A C38 H38B 107.8 . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C3 C4 C41 118.6(3) . . ? C3 C4 C5 121.1(3) . . ? C41 C4 C5 120.3(3) . . ? C42 C41 C4 121.9(3) . . ? C42 C41 H41 119.0 . . ? C4 C41 H41 119.0 . . ? O43 C42 C41 124.9(3) . . ? O43 C42 C32 115.7(3) . . ? C41 C42 C32 119.4(3) . . ? C42 O43 C44 117.7(2) . . ? O43 C44 C45 108.2(2) . . ? O43 C44 H44A 110.1 . . ? C45 C44 H44A 110.1 . . ? O43 C44 H44B 110.1 . . ? C45 C44 H44B 110.1 . . ? H44A C44 H44B 108.4 . . ? C44 C45 C46 112.0(2) . . ? C44 C45 H45A 109.2 . . ? C46 C45 H45A 109.2 . . ? C44 C45 H45B 109.2 . . ? C46 C45 H45B 109.2 . . ? H45A C45 H45B 107.9 . . ? C47 C46 C45 113.5(3) . . ? C47 C46 H46A 108.9 . . ? C45 C46 H46A 108.9 . . ? C47 C46 H46B 108.9 . . ? C45 C46 H46B 108.9 . . ? H46A C46 H46B 107.7 . . ? C48 C47 C46 113.8(3) . . ? C48 C47 H47A 108.8 . . ? C46 C47 H47A 108.8 . . ? C48 C47 H47B 108.8 . . ? C46 C47 H47B 108.8 . . ? H47A C47 H47B 107.7 . . ? C47 C48 C49 113.3(3) . . ? C47 C48 H48A 108.9 . . ? C49 C48 H48A 108.9 . . ? C47 C48 H48B 108.9 . . ? C49 C48 H48B 108.9 . . ? H48A C48 H48B 107.7 . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C6 C5 C51 118.8(3) . . ? C6 C5 C4 118.9(3) . . ? C51 C5 C4 122.3(3) . . ? C52 C51 C5 121.7(3) . . ? C52 C51 H51 119.2 . . ? C5 C51 H51 119.2 . . ? O53 C52 C51 124.7(3) . . ? O53 C52 C62 115.4(3) . . ? C51 C52 C62 119.9(3) . . ? C52 O53 C54 118.0(2) . . ? O53 C54 C55 107.3(2) . . ? O53 C54 H54A 110.3 . . ? C55 C54 H54A 110.3 . . ? O53 C54 H54B 110.3 . . ? C55 C54 H54B 110.3 . . ? H54A C54 H54B 108.5 . . ? C54 C55 C56 113.1(3) . . ? C54 C55 H55A 109.0 . . ? C56 C55 H55A 109.0 . . ? C54 C55 H55B 109.0 . . ? C56 C55 H55B 109.0 . . ? H55A C55 H55B 107.8 . . ? C55 C56 C57 113.6(3) . . ? C55 C56 H56A 108.8 . . ? C57 C56 H56A 108.8 . . ? C55 C56 H56B 108.8 . . ? C57 C56 H56B 108.8 . . ? H56A C56 H56B 107.7 . . ? C58 C57 C56 113.8(3) . . ? C58 C57 H57A 108.8 . . ? C56 C57 H57A 108.8 . . ? C58 C57 H57B 108.8 . . ? C56 C57 H57B 108.8 . . ? H57A C57 H57B 107.7 . . ? C57 C58 C59 113.3(3) . . ? C57 C58 H58A 108.9 . . ? C59 C58 H58A 108.9 . . ? C57 C58 H58B 108.9 . . ? C59 C58 H58B 108.9 . . ? H58A C58 H58B 107.7 . . ? C58 C59 H59A 109.5 . . ? C58 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C58 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C5 C6 C61 118.2(3) . . ? C5 C6 C1 120.4(3) . . ? C61 C6 C1 121.4(3) . . ? C62 C61 C6 123.1(3) . . ? C62 C61 H61 118.5 . . ? C6 C61 H61 118.5 . . ? C61 C62 C52 118.4(3) . . ? C61 C62 C63 117.6(3) . . ? C52 C62 C63 123.9(3) . . ? C64 C63 C62 166.8(3) 3_666 . ? C63 C64 C14 170.5(3) 3_666 . ? 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 C2 C1 C11 C12 1.0(5) . . . . ? C6 C1 C11 C12 179.9(3) . . . . ? C1 C11 C12 C22 0.8(5) . . . . ? C1 C11 C12 C13 -177.8(3) . . . . ? C11 C12 C13 C14 2.0(14) . . . . ? C22 C12 C13 C14 -176.6(11) . . . . ? C12 C13 C14 C64 -3(3) . . . . ? C11 C1 C2 C21 -2.2(5) . . . . ? C6 C1 C2 C21 178.8(3) . . . . ? C11 C1 C2 C3 177.2(3) . . . . ? C6 C1 C2 C3 -1.7(5) . . . . ? C1 C2 C21 C22 1.8(5) . . . . ? C3 C2 C21 C22 -177.6(3) . . . . ? C2 C21 C22 O23 179.7(3) . . . . ? C2 C21 C22 C12 -0.1(5) . . . . ? C11 C12 C22 O23 178.9(3) . . . . ? C13 C12 C22 O23 -2.6(5) . . . . ? C11 C12 C22 C21 -1.3(5) . . . . ? C13 C12 C22 C21 177.2(3) . . . . ? C21 C22 O23 C24 -4.3(5) . . . . ? C12 C22 O23 C24 175.5(3) . . . . ? C22 O23 C24 C25 -175.6(3) . . . . ? O23 C24 C25 C26 175.4(3) . . . . ? C24 C25 C26 C27 160.5(7) . . . . ? C25 C26 C27 C28 57.8(12) . . . . ? C26 C27 C28 C29 171.1(17) . . . . ? C21 C2 C3 C4 179.9(3) . . . . ? C1 C2 C3 C4 0.5(5) . . . . ? C21 C2 C3 C31 -0.4(5) . . . . ? C1 C2 C3 C31 -179.8(3) . . . . ? C4 C3 C31 C32 0.3(5) . . . . ? C2 C3 C31 C32 -179.5(3) . . . . ? C3 C31 C32 O33 180.0(3) . . . . ? C3 C31 C32 C42 0.7(5) . . . . ? C31 C32 O33 C34 1.3(5) . . . . ? C42 C32 O33 C34 -179.5(3) . . . . ? C32 O33 C34 C35 -174.8(3) . . . . ? O33 C34 C35 C36 -67.8(3) . . . . ? C34 C35 C36 C37 177.9(3) . . . . ? C35 C36 C37 C38 62.7(4) . . . . ? C36 C37 C38 C39 -178.8(3) . . . . ? C31 C3 C4 C41 -0.4(5) . . . . ? C2 C3 C4 C41 179.3(3) . . . . ? C31 C3 C4 C5 -179.8(3) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C3 C4 C41 C42 -0.4(5) . . . . ? C5 C4 C41 C42 179.0(3) . . . . ? C4 C41 C42 O43 -178.9(3) . . . . ? C4 C41 C42 C32 1.4(5) . . . . ? O33 C32 C42 O43 -0.6(4) . . . . ? C31 C32 C42 O43 178.7(3) . . . . ? O33 C32 C42 C41 179.1(3) . . . . ? C31 C32 C42 C41 -1.6(5) . . . . ? C41 C42 O43 C44 -0.1(5) . . . . ? C32 C42 O43 C44 179.6(3) . . . . ? C42 O43 C44 C45 178.3(3) . . . . ? O43 C44 C45 C46 173.5(3) . . . . ? C44 C45 C46 C47 172.1(3) . . . . ? C45 C46 C47 C48 -179.7(3) . . . . ? C46 C47 C48 C49 176.3(3) . . . . ? C3 C4 C5 C6 0.9(5) . . . . ? C41 C4 C5 C6 -178.4(3) . . . . ? C3 C4 C5 C51 180.0(3) . . . . ? C41 C4 C5 C51 0.6(5) . . . . ? C6 C5 C51 C52 -0.6(5) . . . . ? C4 C5 C51 C52 -179.7(3) . . . . ? C5 C51 C52 O53 -179.5(3) . . . . ? C5 C51 C52 C62 0.7(5) . . . . ? C51 C52 O53 C54 6.7(5) . . . . ? C62 C52 O53 C54 -173.5(3) . . . . ? C52 O53 C54 C55 170.8(3) . . . . ? O53 C54 C55 C56 -65.5(4) . . . . ? C54 C55 C56 C57 -169.0(3) . . . . ? C55 C56 C57 C58 179.4(3) . . . . ? C56 C57 C58 C59 -171.9(3) . . . . ? C51 C5 C6 C61 -0.1(5) . . . . ? C4 C5 C6 C61 179.0(3) . . . . ? C51 C5 C6 C1 178.7(3) . . . . ? C4 C5 C6 C1 -2.2(5) . . . . ? C11 C1 C6 C5 -176.3(3) . . . . ? C2 C1 C6 C5 2.6(5) . . . . ? C11 C1 C6 C61 2.5(5) . . . . ? C2 C1 C6 C61 -178.6(3) . . . . ? C5 C6 C61 C62 0.6(5) . . . . ? C1 C6 C61 C62 -178.2(3) . . . . ? C6 C61 C62 C52 -0.5(5) . . . . ? C6 C61 C62 C63 176.0(3) . . . . ? O53 C52 C62 C61 -179.9(3) . . . . ? C51 C52 C62 C61 -0.2(5) . . . . ? O53 C52 C62 C63 3.8(5) . . . . ? C51 C52 C62 C63 -176.4(3) . . . . ? C61 C62 C63 C64 -8.9(17) . . . 3_666 ? C52 C62 C63 C64 167.4(14) . . . 3_666 ? C13 C14 C64 C63 4(4) . . . 3_666 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.221 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.050