# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_bcyct03 _database_code_depnum_ccdc_archive 'CCDC 845646' #TrackingRef 'BCYCT03.cif' _audit_update_record ; 2011-09-22 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 O2' _chemical_formula_sum 'C16 H18 O2' _chemical_formula_weight 242.30 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.7097(11) _cell_length_b 19.332(2) _cell_length_c 9.3678(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.144(9) _cell_angle_gamma 90.00 _cell_volume 1394.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3633 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 21.36 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.154 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9679 _exptl_absorpt_correction_T_max 0.9852 _exptl_absorpt_process_details 'SAINT ver. 7.34; Bruker SADABS' _exptl_special_details ? _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13979 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3245 _reflns_number_gt 2414 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. The absolute configuration of the molecule was not determined. Flack parameter and su is 0 and 10, respectively. ; _chemical_absolute_configuration syn _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^)+(0.0410P)^2^+0.0613P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.032(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 3245 _refine_ls_number_parameters 330 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0864 _refine_ls_wR_factor_gt 0.0767 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.005 _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 C11 C -0.0410(3) 0.88018(11) 0.5781(2) 0.0398(5) Uani 1 1 d . . . C12 C -0.1764(3) 0.85304(12) 0.6518(3) 0.0513(6) Uani 1 1 d . . . H12A H -0.1513 0.8237 0.7289 0.062 Uiso 1 1 calc R . . C13 C -0.3466(3) 0.86838(14) 0.6140(3) 0.0581(7) Uani 1 1 d . . . H13A H -0.4350 0.8496 0.6654 0.070 Uiso 1 1 calc R . . C14 C -0.3862(3) 0.91126(14) 0.5007(3) 0.0614(7) Uani 1 1 d . . . H14A H -0.5014 0.9219 0.4752 0.074 Uiso 1 1 calc R . . C15 C -0.2540(3) 0.93861(13) 0.4243(3) 0.0516(6) Uani 1 1 d . . . H15A H -0.2811 0.9675 0.3470 0.062 Uiso 1 1 calc R . . C16 C -0.0807(3) 0.92346(10) 0.4617(2) 0.0387(5) Uani 1 1 d . . . C17 C 0.1455(3) 0.86539(12) 0.6277(2) 0.0443(5) Uani 1 1 d . . . H17A H 0.2195 0.8767 0.5492 0.053 Uiso 1 1 calc R . . O1 O 0.1657(2) 0.79288(8) 0.65904(17) 0.0573(4) Uani 1 1 d . . . H1A H 0.2207 0.7858 0.7573 0.069 Uiso 1 1 d . . . C18 C 0.2013(3) 0.90993(14) 0.7543(3) 0.0612(7) Uani 1 1 d . . . H18A H 0.3192 0.8992 0.7846 0.092 Uiso 1 1 calc R . . H18B H 0.1270 0.9012 0.8312 0.092 Uiso 1 1 calc R . . H18C H 0.1932 0.9578 0.7275 0.092 Uiso 1 1 calc R . . C21 C 0.1244(3) 0.91419(12) 0.2630(2) 0.0447(5) Uani 1 1 d . . . C22 C 0.2515(3) 0.94423(14) 0.1820(3) 0.0584(7) Uani 1 1 d . . . H22A H 0.2988 0.9188 0.1094 0.070 Uiso 1 1 calc R . . C23 C 0.3076(3) 1.01058(17) 0.2080(3) 0.0673(8) Uani 1 1 d . . . H23A H 0.3924 1.0297 0.1531 0.081 Uiso 1 1 calc R . . C24 C 0.2392(4) 1.04894(16) 0.3147(3) 0.0666(7) Uani 1 1 d . . . H24A H 0.2762 1.0941 0.3315 0.080 Uiso 1 1 calc R . . C25 C 0.1155(3) 1.02003(13) 0.3966(3) 0.0539(6) Uani 1 1 d . . . H25A H 0.0701 1.0459 0.4694 0.065 Uiso 1 1 calc R . . C26 C 0.0571(3) 0.95294(11) 0.3727(2) 0.0393(5) Uani 1 1 d . . . C27 C 0.0609(3) 0.84127(12) 0.2320(3) 0.0542(6) Uani 1 1 d . . . H27A H 0.0168 0.8220 0.3197 0.065 Uiso 1 1 calc R . . O2 O 0.1986(3) 0.79839(10) 0.18835(18) 0.0760(6) Uani 1 1 d . . . H2A H 0.2710 0.7922 0.2783 0.091 Uiso 1 1 d . . . C28 C -0.0816(4) 0.83838(15) 0.1165(3) 0.0748(8) Uani 1 1 d . . . H28A H -0.1193 0.7914 0.1032 0.112 Uiso 1 1 calc R . . H28B H -0.0391 0.8556 0.0289 0.112 Uiso 1 1 calc R . . H28C H -0.1775 0.8663 0.1435 0.112 Uiso 1 1 calc R . . C31 C 0.5660(3) 0.66777(11) 0.3404(2) 0.0407(5) Uani 1 1 d . . . C32 C 0.7073(3) 0.69495(12) 0.4198(3) 0.0528(6) Uani 1 1 d . . . H32A H 0.6886 0.7213 0.5006 0.063 Uiso 1 1 calc R . . C33 C 0.8749(3) 0.68348(14) 0.3809(3) 0.0614(7) Uani 1 1 d . . . H33A H 0.9681 0.7024 0.4348 0.074 Uiso 1 1 calc R . . C34 C 0.9040(3) 0.64412(15) 0.2623(3) 0.0647(7) Uani 1 1 d . . . H34A H 1.0170 0.6357 0.2368 0.078 Uiso 1 1 calc R . . C35 C 0.7655(3) 0.61728(13) 0.1815(3) 0.0549(6) Uani 1 1 d . . . H35A H 0.7858 0.5905 0.1017 0.066 Uiso 1 1 calc R . . C36 C 0.5953(3) 0.62960(10) 0.2175(2) 0.0405(5) Uani 1 1 d . . . C37 C 0.3840(3) 0.67881(12) 0.3888(2) 0.0463(5) Uani 1 1 d . . . H37A H 0.3022 0.6714 0.3064 0.056 Uiso 1 1 calc R . . O3 O 0.3686(2) 0.74911(9) 0.43402(18) 0.0596(5) Uani 1 1 d . . . H3A H 0.2924 0.7520 0.5164 0.072 Uiso 1 1 d . . . C38 C 0.3401(4) 0.62834(14) 0.5045(3) 0.0642(7) Uani 1 1 d . . . H38A H 0.2259 0.6381 0.5352 0.096 Uiso 1 1 calc R . . H38B H 0.4232 0.6328 0.5842 0.096 Uiso 1 1 calc R . . H38C H 0.3435 0.5820 0.4678 0.096 Uiso 1 1 calc R . . C41 C 0.3732(3) 0.64237(12) 0.0125(2) 0.0455(5) Uani 1 1 d . . . C42 C 0.2368(4) 0.61470(17) -0.0721(3) 0.0659(8) Uani 1 1 d . . . H42A H 0.1865 0.6407 -0.1469 0.079 Uiso 1 1 calc R . . C43 C 0.1752(4) 0.5493(2) -0.0466(3) 0.0807(9) Uani 1 1 d . . . H43A H 0.0835 0.5316 -0.1040 0.097 Uiso 1 1 calc R . . C44 C 0.2486(4) 0.51012(17) 0.0632(3) 0.0797(9) Uani 1 1 d . . . H44A H 0.2061 0.4661 0.0807 0.096 Uiso 1 1 calc R . . C45 C 0.3847(3) 0.53620(13) 0.1468(3) 0.0599(7) Uani 1 1 d . . . H45A H 0.4351 0.5093 0.2203 0.072 Uiso 1 1 calc R . . C46 C 0.4484(3) 0.60239(11) 0.1233(2) 0.0427(5) Uani 1 1 d . . . C47 C 0.4411(3) 0.71416(13) -0.0171(3) 0.0550(6) Uani 1 1 d . . . H47A H 0.4915 0.7333 0.0728 0.066 Uiso 1 1 calc R . . O4 O 0.3049(3) 0.75939(10) -0.06941(17) 0.0780(6) Uani 1 1 d . . . H4A H 0.2502 0.7768 0.0152 0.094 Uiso 1 1 d . . . C48 C 0.5798(4) 0.71463(17) -0.1255(3) 0.0760(8) Uani 1 1 d . . . H48A H 0.6236 0.7608 -0.1350 0.114 Uiso 1 1 calc R . . H48B H 0.5307 0.6990 -0.2162 0.114 Uiso 1 1 calc R . . H48C H 0.6729 0.6844 -0.0939 0.114 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 C11 0.0410(12) 0.0392(11) 0.0393(11) -0.0034(10) 0.0049(9) 0.0009(9) C12 0.0521(15) 0.0514(14) 0.0516(14) 0.0044(11) 0.0134(11) -0.0030(11) C13 0.0444(14) 0.0636(16) 0.0680(17) 0.0036(14) 0.0178(12) -0.0058(12) C14 0.0386(13) 0.0689(17) 0.0771(18) 0.0028(15) 0.0057(12) 0.0013(12) C15 0.0450(13) 0.0511(13) 0.0586(14) 0.0033(12) 0.0018(11) 0.0039(11) C16 0.0408(11) 0.0369(11) 0.0386(11) -0.0036(9) 0.0045(9) 0.0003(9) C17 0.0446(12) 0.0519(14) 0.0369(11) 0.0063(10) 0.0062(10) 0.0032(10) O1 0.0709(11) 0.0508(9) 0.0494(9) 0.0026(8) -0.0050(8) 0.0149(8) C18 0.0557(15) 0.0612(16) 0.0652(16) -0.0044(13) -0.0108(12) -0.0017(13) C21 0.0473(12) 0.0476(13) 0.0392(12) 0.0102(11) 0.0030(10) 0.0065(10) C22 0.0595(15) 0.0709(18) 0.0459(14) 0.0141(12) 0.0143(12) 0.0090(13) C23 0.0514(15) 0.085(2) 0.0653(18) 0.0251(16) 0.0042(13) -0.0152(15) C24 0.0677(17) 0.0639(17) 0.0678(18) 0.0079(15) -0.0014(14) -0.0255(14) C25 0.0592(14) 0.0483(13) 0.0540(14) 0.0002(11) 0.0011(11) -0.0115(12) C26 0.0371(11) 0.0418(12) 0.0390(11) 0.0054(9) 0.0007(9) 0.0010(9) C27 0.0756(17) 0.0454(13) 0.0424(13) 0.0012(10) 0.0114(12) 0.0116(12) O2 0.1114(16) 0.0680(12) 0.0491(10) -0.0050(9) 0.0083(10) 0.0442(11) C28 0.092(2) 0.0582(17) 0.0734(18) -0.0045(15) -0.0052(17) -0.0037(15) C31 0.0402(11) 0.0346(11) 0.0461(12) 0.0035(10) -0.0079(10) 0.0005(9) C32 0.0529(15) 0.0495(14) 0.0544(14) -0.0026(11) -0.0121(12) -0.0019(11) C33 0.0417(14) 0.0584(16) 0.0818(19) 0.0089(14) -0.0176(13) -0.0114(12) C34 0.0387(13) 0.0754(18) 0.0798(19) 0.0082(16) 0.0003(13) -0.0003(12) C35 0.0470(14) 0.0586(15) 0.0589(15) 0.0012(12) 0.0009(11) 0.0043(11) C36 0.0406(11) 0.0349(11) 0.0452(12) 0.0027(10) -0.0041(9) 0.0012(9) C37 0.0437(12) 0.0455(13) 0.0486(13) -0.0067(11) -0.0070(10) 0.0037(10) O3 0.0689(11) 0.0495(10) 0.0606(10) -0.0085(8) 0.0044(8) 0.0115(8) C38 0.0561(15) 0.0668(17) 0.0702(17) 0.0085(14) 0.0066(13) 0.0000(13) C41 0.0442(12) 0.0529(14) 0.0393(12) -0.0087(11) 0.0010(10) 0.0069(10) C42 0.0592(15) 0.090(2) 0.0469(14) -0.0144(14) -0.0121(12) 0.0076(15) C43 0.0648(18) 0.102(3) 0.074(2) -0.0312(19) -0.0093(16) -0.0237(18) C44 0.083(2) 0.073(2) 0.082(2) -0.0169(17) -0.0009(17) -0.0319(17) C45 0.0697(17) 0.0482(15) 0.0609(16) -0.0037(12) -0.0045(13) -0.0087(12) C46 0.0427(12) 0.0409(12) 0.0442(12) -0.0059(10) -0.0014(10) 0.0006(9) C47 0.0747(17) 0.0505(14) 0.0392(13) 0.0001(11) -0.0030(12) 0.0134(13) O4 0.1100(15) 0.0792(14) 0.0442(10) 0.0073(9) -0.0002(10) 0.0450(12) C48 0.088(2) 0.0749(19) 0.0660(18) 0.0120(15) 0.0148(16) -0.0007(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 C12 1.386(3) . ? C11 C16 1.395(3) . ? C11 C17 1.514(3) . ? C12 C13 1.373(3) . ? C12 H12A 0.9300 . ? C13 C14 1.368(4) . ? C13 H13A 0.9300 . ? C14 C15 1.381(3) . ? C14 H14A 0.9300 . ? C15 C16 1.394(3) . ? C15 H15A 0.9300 . ? C16 C26 1.499(3) . ? C17 O1 1.439(3) . ? C17 C18 1.509(3) . ? C17 H17A 0.9800 . ? O1 H1A 1.0016 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C21 C26 1.394(3) . ? C21 C22 1.398(3) . ? C21 C27 1.515(3) . ? C22 C23 1.371(4) . ? C22 H22A 0.9300 . ? C23 C24 1.373(4) . ? C23 H23A 0.9300 . ? C24 C25 1.374(3) . ? C24 H24A 0.9300 . ? C25 C26 1.387(3) . ? C25 H25A 0.9300 . ? C27 O2 1.425(3) . ? C27 C28 1.500(4) . ? C27 H27A 0.9800 . ? O2 H2A 0.9922 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C31 C32 1.388(3) . ? C31 C36 1.396(3) . ? C31 C37 1.513(3) . ? C32 C33 1.380(4) . ? C32 H32A 0.9300 . ? C33 C34 1.375(4) . ? C33 H33A 0.9300 . ? C34 C35 1.377(4) . ? C34 H34A 0.9300 . ? C35 C36 1.392(3) . ? C35 H35A 0.9300 . ? C36 C46 1.493(3) . ? C37 O3 1.430(3) . ? C37 C38 1.511(4) . ? C37 H37A 0.9800 . ? O3 H3A 0.9966 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C41 C42 1.388(3) . ? C41 C46 1.395(3) . ? C41 C47 1.514(3) . ? C42 C43 1.376(5) . ? C42 H42A 0.9300 . ? C43 C44 1.374(5) . ? C43 H43A 0.9300 . ? C44 C45 1.371(4) . ? C44 H44A 0.9300 . ? C45 C46 1.392(3) . ? C45 H45A 0.9300 . ? C47 O4 1.432(3) . ? C47 C48 1.514(4) . ? C47 H47A 0.9800 . ? O4 H4A 0.9776 . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 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 C12 C11 C16 118.5(2) . . ? C12 C11 C17 120.3(2) . . ? C16 C11 C17 121.17(19) . . ? C13 C12 C11 121.6(2) . . ? C13 C12 H12A 119.2 . . ? C11 C12 H12A 119.2 . . ? C14 C13 C12 120.1(2) . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? C13 C14 C15 119.6(2) . . ? C13 C14 H14A 120.2 . . ? C15 C14 H14A 120.2 . . ? C14 C15 C16 120.9(2) . . ? C14 C15 H15A 119.5 . . ? C16 C15 H15A 119.5 . . ? C15 C16 C11 119.26(19) . . ? C15 C16 C26 118.63(19) . . ? C11 C16 C26 122.08(18) . . ? O1 C17 C18 111.89(19) . . ? O1 C17 C11 109.68(18) . . ? C18 C17 C11 111.01(19) . . ? O1 C17 H17A 108.0 . . ? C18 C17 H17A 108.0 . . ? C11 C17 H17A 108.0 . . ? C17 O1 H1A 110.9 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C26 C21 C22 118.5(2) . . ? C26 C21 C27 120.79(19) . . ? C22 C21 C27 120.7(2) . . ? C23 C22 C21 121.0(2) . . ? C23 C22 H22A 119.5 . . ? C21 C22 H22A 119.5 . . ? C22 C23 C24 120.3(2) . . ? C22 C23 H23A 119.9 . . ? C24 C23 H23A 119.9 . . ? C23 C24 C25 119.5(3) . . ? C23 C24 H24A 120.3 . . ? C25 C24 H24A 120.3 . . ? C24 C25 C26 121.3(2) . . ? C24 C25 H25A 119.4 . . ? C26 C25 H25A 119.4 . . ? C25 C26 C21 119.4(2) . . ? C25 C26 C16 120.0(2) . . ? C21 C26 C16 120.63(19) . . ? O2 C27 C28 107.4(2) . . ? O2 C27 C21 111.0(2) . . ? C28 C27 C21 112.9(2) . . ? O2 C27 H27A 108.5 . . ? C28 C27 H27A 108.5 . . ? C21 C27 H27A 108.5 . . ? C27 O2 H2A 102.7 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C32 C31 C36 119.0(2) . . ? C32 C31 C37 119.9(2) . . ? C36 C31 C37 121.08(18) . . ? C33 C32 C31 121.1(2) . . ? C33 C32 H32A 119.5 . . ? C31 C32 H32A 119.5 . . ? C34 C33 C32 119.9(2) . . ? C34 C33 H33A 120.0 . . ? C32 C33 H33A 120.0 . . ? C33 C34 C35 119.8(2) . . ? C33 C34 H34A 120.1 . . ? C35 C34 H34A 120.1 . . ? C34 C35 C36 121.0(2) . . ? C34 C35 H35A 119.5 . . ? C36 C35 H35A 119.5 . . ? C35 C36 C31 119.1(2) . . ? C35 C36 C46 119.4(2) . . ? C31 C36 C46 121.43(18) . . ? O3 C37 C38 112.1(2) . . ? O3 C37 C31 108.44(18) . . ? C38 C37 C31 111.82(19) . . ? O3 C37 H37A 108.1 . . ? C38 C37 H37A 108.1 . . ? C31 C37 H37A 108.1 . . ? C37 O3 H3A 110.2 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C42 C41 C46 118.8(2) . . ? C42 C41 C47 120.5(2) . . ? C46 C41 C47 120.7(2) . . ? C43 C42 C41 120.9(3) . . ? C43 C42 H42A 119.6 . . ? C41 C42 H42A 119.6 . . ? C44 C43 C42 120.3(3) . . ? C44 C43 H43A 119.9 . . ? C42 C43 H43A 119.9 . . ? C45 C44 C43 119.7(3) . . ? C45 C44 H44A 120.1 . . ? C43 C44 H44A 120.1 . . ? C44 C45 C46 120.9(3) . . ? C44 C45 H45A 119.6 . . ? C46 C45 H45A 119.6 . . ? C45 C46 C41 119.4(2) . . ? C45 C46 C36 119.6(2) . . ? C41 C46 C36 121.03(19) . . ? O4 C47 C41 111.6(2) . . ? O4 C47 C48 107.4(2) . . ? C41 C47 C48 113.1(2) . . ? O4 C47 H47A 108.2 . . ? C41 C47 H47A 108.2 . . ? C48 C47 H47A 108.2 . . ? C47 O4 H4A 105.9 . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.126 _refine_diff_density_min -0.114 _refine_diff_density_rms 0.026 data_bcyct05_2 _database_code_depnum_ccdc_archive 'CCDC 845647' #TrackingRef 'BCYCT05_2.cif' _audit_update_record ; 2011-09-22 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H30 O2' _chemical_formula_sum 'C22 H30 O2' _chemical_formula_weight 326.46 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 Tetragonal _symmetry_space_group_name_H-M 'P 43 21 2' _symmetry_space_group_name_Hall 'P 4nw 2abw' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 9.8930(2) _cell_length_b 9.8930(2) _cell_length_c 40.1220(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3926.80(19) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4954 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 27.32 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.104 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9536 _exptl_absorpt_correction_T_max 0.9784 _exptl_absorpt_process_details 'SAINT ver. 7.34; Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 33091 _diffrn_reflns_av_R_equivalents 0.0791 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -48 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.34 _reflns_number_total 3584 _reflns_number_gt 2450 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _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. The structural solution was obtained through direct method. The two -OH protons were located with the Fourier difference map, are disordered into two equal parts, this is due to the possibility of two modes of hydrogen bonding between neighboring molecules. One of the protons will be left without a H-bond acceptor regardless of the configuration of the hydrogen bonds. These protons are restrained with DFIX. All other protons were calculated. Without any heavy elements, the absolute configuration of the molecule cannot be determined, and thus the Flack parameter and its esd should be ignored. ; _chemical_absolute_configuration syn _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^)+(0.0395P)^2^+0.2788P] 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 SHELXL _refine_ls_extinction_coef 0.0066(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(17) _refine_ls_number_reflns 3584 _refine_ls_number_parameters 236 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0958 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.058 _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 0.7178(2) 0.1409(2) -0.05234(5) 0.0411(6) Uani 1 1 d . . . C2 C 0.7209(3) 0.0401(3) -0.07664(6) 0.0577(7) Uani 1 1 d . . . H2A H 0.7373 0.0639 -0.0987 0.069 Uiso 1 1 calc R . . C3 C 0.7004(3) -0.0941(3) -0.06879(7) 0.0666(8) Uani 1 1 d . . . H3A H 0.7021 -0.1593 -0.0855 0.080 Uiso 1 1 calc R . . C4 C 0.6774(3) -0.1310(3) -0.03649(7) 0.0627(8) Uani 1 1 d . . . H4A H 0.6628 -0.2212 -0.0311 0.075 Uiso 1 1 calc R . . C5 C 0.6761(2) -0.0333(2) -0.01180(6) 0.0534(6) Uani 1 1 d . . . H5A H 0.6596 -0.0590 0.0101 0.064 Uiso 1 1 calc R . . C6 C 0.6990(2) 0.1031(2) -0.01900(5) 0.0403(6) Uani 1 1 d . . . C7 C 0.7034(2) 0.2041(2) 0.00919(5) 0.0427(6) Uani 1 1 d . . . H7A H 0.6899 0.2940 -0.0005 0.051 Uiso 1 1 calc R . . O1 O 0.59266(17) 0.17940(17) 0.03167(4) 0.0608(5) Uani 1 1 d D . . H11 H 0.540(4) 0.257(3) 0.0319(12) 0.073 Uiso 0.50 1 d PD A 1 H12 H 0.522(4) 0.134(5) 0.0215(12) 0.073 Uiso 0.50 1 d PD B 2 C8 C 0.8374(2) 0.2078(2) 0.02907(5) 0.0491(6) Uani 1 1 d . . . C9 C 0.9519(3) 0.2496(3) 0.00578(7) 0.0751(9) Uani 1 1 d . . . H9A H 1.0344 0.2572 0.0182 0.113 Uiso 1 1 calc R . . H9B H 0.9308 0.3353 -0.0042 0.113 Uiso 1 1 calc R . . H9C H 0.9625 0.1828 -0.0114 0.113 Uiso 1 1 calc R . . C10 C 0.8724(3) 0.0724(3) 0.04512(6) 0.0671(8) Uani 1 1 d . . . H10A H 0.9486 0.0836 0.0597 0.101 Uiso 1 1 calc R . . H10B H 0.8941 0.0079 0.0281 0.101 Uiso 1 1 calc R . . H10C H 0.7963 0.0405 0.0577 0.101 Uiso 1 1 calc R . . C11 C 0.8236(3) 0.3139(3) 0.05659(6) 0.0775(9) Uani 1 1 d . . . H11A H 0.9094 0.3263 0.0673 0.116 Uiso 1 1 calc R . . H11B H 0.7582 0.2840 0.0727 0.116 Uiso 1 1 calc R . . H11C H 0.7946 0.3980 0.0470 0.116 Uiso 1 1 calc R . . C12 C 0.7402(2) 0.2839(2) -0.06314(5) 0.0411(6) Uani 1 1 d . . . C13 C 0.8684(2) 0.3198(3) -0.07411(6) 0.0540(7) Uani 1 1 d . . . H13A H 0.9342 0.2530 -0.0757 0.065 Uiso 1 1 calc R . . C14 C 0.9017(3) 0.4497(3) -0.08260(6) 0.0650(8) Uani 1 1 d . . . H14A H 0.9884 0.4703 -0.0899 0.078 Uiso 1 1 calc R . . C15 C 0.8056(3) 0.5490(3) -0.08015(6) 0.0593(7) Uani 1 1 d . . . H15A H 0.8277 0.6383 -0.0849 0.071 Uiso 1 1 calc R . . C16 C 0.6758(3) 0.5156(2) -0.07055(5) 0.0503(7) Uani 1 1 d . . . H16A H 0.6110 0.5834 -0.0694 0.060 Uiso 1 1 calc R . . C17 C 0.6390(2) 0.3840(2) -0.06263(5) 0.0379(6) Uani 1 1 d . . . C18 C 0.4922(2) 0.3525(2) -0.05469(5) 0.0422(6) Uani 1 1 d . . . H18A H 0.4899 0.2692 -0.0415 0.051 Uiso 1 1 calc R . . O2 O 0.43743(17) 0.45977(18) -0.03458(4) 0.0565(5) Uani 1 1 d D . . H21 H 0.444(5) 0.453(5) -0.0121(5) 0.068 Uiso 0.50 1 d PD C 1 H22 H 0.363(3) 0.504(5) -0.0435(11) 0.068 Uiso 0.50 1 d PD D 2 C19 C 0.3999(2) 0.3319(2) -0.08566(5) 0.0474(6) Uani 1 1 d . . . C20 C 0.2603(2) 0.2853(3) -0.07359(7) 0.0748(9) Uani 1 1 d . . . H20A H 0.2052 0.2623 -0.0925 0.112 Uiso 1 1 calc R . . H20B H 0.2180 0.3569 -0.0613 0.112 Uiso 1 1 calc R . . H20C H 0.2704 0.2075 -0.0595 0.112 Uiso 1 1 calc R . . C21 C 0.4585(3) 0.2207(3) -0.10786(6) 0.0724(8) Uani 1 1 d . . . H21A H 0.3982 0.2039 -0.1261 0.109 Uiso 1 1 calc R . . H21B H 0.4694 0.1394 -0.0951 0.109 Uiso 1 1 calc R . . H21C H 0.5448 0.2490 -0.1163 0.109 Uiso 1 1 calc R . . C22 C 0.3835(3) 0.4610(3) -0.10595(6) 0.0692(8) Uani 1 1 d . . . H22A H 0.3190 0.4462 -0.1235 0.104 Uiso 1 1 calc R . . H22B H 0.4689 0.4859 -0.1155 0.104 Uiso 1 1 calc R . . H22C H 0.3521 0.5324 -0.0917 0.104 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 C1 0.0367(13) 0.0434(15) 0.0432(13) -0.0009(12) -0.0037(11) 0.0114(11) C2 0.0650(18) 0.0556(18) 0.0526(16) -0.0071(14) -0.0116(13) 0.0244(14) C3 0.077(2) 0.0463(17) 0.076(2) -0.0174(15) -0.0263(17) 0.0196(15) C4 0.0657(19) 0.0389(16) 0.083(2) -0.0046(15) -0.0211(16) 0.0024(13) C5 0.0520(16) 0.0447(16) 0.0636(16) 0.0069(14) -0.0059(13) 0.0015(12) C6 0.0351(13) 0.0371(14) 0.0488(14) 0.0020(11) -0.0024(11) 0.0053(10) C7 0.0483(14) 0.0363(13) 0.0435(14) 0.0038(11) 0.0064(12) 0.0072(11) O1 0.0591(12) 0.0604(13) 0.0630(11) 0.0035(10) 0.0194(10) 0.0121(9) C8 0.0619(17) 0.0464(15) 0.0389(13) 0.0015(12) -0.0038(12) 0.0034(12) C9 0.0616(19) 0.098(2) 0.0657(18) 0.0048(16) -0.0103(15) -0.0149(16) C10 0.078(2) 0.0607(19) 0.0622(17) 0.0046(14) -0.0177(15) 0.0163(14) C11 0.106(2) 0.062(2) 0.0651(18) -0.0097(15) -0.0163(17) 0.0043(17) C12 0.0422(15) 0.0464(15) 0.0347(13) 0.0041(11) 0.0018(10) 0.0071(12) C13 0.0463(16) 0.0612(18) 0.0543(15) 0.0114(14) 0.0075(12) 0.0155(14) C14 0.0497(17) 0.080(2) 0.0659(18) 0.0199(16) 0.0092(14) 0.0003(16) C15 0.063(2) 0.0540(17) 0.0608(16) 0.0109(14) -0.0009(15) -0.0066(15) C16 0.0595(18) 0.0454(15) 0.0460(14) 0.0017(12) -0.0015(13) 0.0080(13) C17 0.0436(15) 0.0419(15) 0.0284(12) -0.0001(10) -0.0009(11) 0.0067(11) C18 0.0461(15) 0.0453(15) 0.0352(12) 0.0019(11) 0.0041(11) 0.0151(11) O2 0.0634(12) 0.0693(12) 0.0368(9) -0.0083(9) 0.0033(9) 0.0287(9) C19 0.0438(14) 0.0522(16) 0.0464(14) -0.0039(12) -0.0060(11) 0.0106(12) C20 0.0498(18) 0.082(2) 0.093(2) -0.0064(17) -0.0094(15) 0.0018(15) C21 0.071(2) 0.082(2) 0.0646(17) -0.0300(15) -0.0169(15) 0.0177(16) C22 0.083(2) 0.076(2) 0.0480(15) 0.0047(14) -0.0197(14) 0.0164(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.395(3) . ? C1 C6 1.401(3) . ? C1 C12 1.496(3) . ? C2 C3 1.379(4) . ? C2 H2A 0.9300 . ? C3 C4 1.365(4) . ? C3 H3A 0.9300 . ? C4 C5 1.384(3) . ? C4 H4A 0.9300 . ? C5 C6 1.398(3) . ? C5 H5A 0.9300 . ? C6 C7 1.510(3) . ? C7 O1 1.440(3) . ? C7 C8 1.548(3) . ? C7 H7A 0.9800 . ? O1 H11 0.93(2) . ? O1 H12 0.922(19) . ? C8 C9 1.526(3) . ? C8 C10 1.526(3) . ? C8 C11 1.530(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.389(3) . ? C12 C17 1.409(3) . ? C13 C14 1.370(3) . ? C13 H13A 0.9300 . ? C14 C15 1.370(3) . ? C14 H14A 0.9300 . ? C15 C16 1.381(3) . ? C15 H15A 0.9300 . ? C16 C17 1.388(3) . ? C16 H16A 0.9300 . ? C17 C18 1.519(3) . ? C18 O2 1.439(3) . ? C18 C19 1.556(3) . ? C18 H18A 0.9800 . ? O2 H21 0.906(18) . ? O2 H22 0.925(19) . ? C19 C22 1.524(3) . ? C19 C21 1.530(3) . ? C19 C20 1.534(3) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 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 C2 C1 C6 118.6(2) . . ? C2 C1 C12 118.1(2) . . ? C6 C1 C12 123.28(19) . . ? C3 C2 C1 121.7(2) . . ? C3 C2 H2A 119.1 . . ? C1 C2 H2A 119.1 . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C3 C4 C5 119.7(2) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C4 C5 C6 121.6(2) . . ? C4 C5 H5A 119.2 . . ? C6 C5 H5A 119.2 . . ? C5 C6 C1 118.4(2) . . ? C5 C6 C7 119.2(2) . . ? C1 C6 C7 122.30(19) . . ? O1 C7 C6 109.58(17) . . ? O1 C7 C8 109.44(17) . . ? C6 C7 C8 115.23(18) . . ? O1 C7 H7A 107.4 . . ? C6 C7 H7A 107.4 . . ? C8 C7 H7A 107.4 . . ? C7 O1 H11 107(3) . . ? C7 O1 H12 112(3) . . ? H11 O1 H12 89(4) . . ? C9 C8 C10 109.2(2) . . ? C9 C8 C11 108.8(2) . . ? C10 C8 C11 108.54(19) . . ? C9 C8 C7 109.08(18) . . ? C10 C8 C7 113.00(19) . . ? C11 C8 C7 108.17(19) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 118.3(2) . . ? C13 C12 C1 117.9(2) . . ? C17 C12 C1 123.8(2) . . ? C14 C13 C12 122.6(2) . . ? C14 C13 H13A 118.7 . . ? C12 C13 H13A 118.7 . . ? C15 C14 C13 119.2(2) . . ? C15 C14 H14A 120.4 . . ? C13 C14 H14A 120.4 . . ? C14 C15 C16 119.6(2) . . ? C14 C15 H15A 120.2 . . ? C16 C15 H15A 120.2 . . ? C15 C16 C17 122.2(2) . . ? C15 C16 H16A 118.9 . . ? C17 C16 H16A 118.9 . . ? C16 C17 C12 118.0(2) . . ? C16 C17 C18 119.44(19) . . ? C12 C17 C18 122.6(2) . . ? O2 C18 C17 109.04(18) . . ? O2 C18 C19 108.89(17) . . ? C17 C18 C19 114.86(17) . . ? O2 C18 H18A 107.9 . . ? C17 C18 H18A 107.9 . . ? C19 C18 H18A 107.9 . . ? C18 O2 H21 119(4) . . ? C18 O2 H22 115(3) . . ? H21 O2 H22 118(5) . . ? C22 C19 C21 109.4(2) . . ? C22 C19 C20 108.94(19) . . ? C21 C19 C20 108.0(2) . . ? C22 C19 C18 112.3(2) . . ? C21 C19 C18 109.69(19) . . ? C20 C19 C18 108.39(19) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 2.8(3) . . . . ? C12 C1 C2 C3 -179.5(2) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C4 C5 C6 C1 2.8(3) . . . . ? C4 C5 C6 C7 -176.9(2) . . . . ? C2 C1 C6 C5 -3.7(3) . . . . ? C12 C1 C6 C5 178.7(2) . . . . ? C2 C1 C6 C7 175.91(19) . . . . ? C12 C1 C6 C7 -1.7(3) . . . . ? C5 C6 C7 O1 -45.1(3) . . . . ? C1 C6 C7 O1 135.2(2) . . . . ? C5 C6 C7 C8 78.8(2) . . . . ? C1 C6 C7 C8 -100.8(2) . . . . ? O1 C7 C8 C9 -173.70(19) . . . . ? C6 C7 C8 C9 62.3(2) . . . . ? O1 C7 C8 C10 64.7(2) . . . . ? C6 C7 C8 C10 -59.3(2) . . . . ? O1 C7 C8 C11 -55.5(2) . . . . ? C6 C7 C8 C11 -179.51(19) . . . . ? C2 C1 C12 C13 -69.0(3) . . . . ? C6 C1 C12 C13 108.6(2) . . . . ? C2 C1 C12 C17 111.4(2) . . . . ? C6 C1 C12 C17 -71.0(3) . . . . ? C17 C12 C13 C14 3.7(4) . . . . ? C1 C12 C13 C14 -175.9(2) . . . . ? C12 C13 C14 C15 0.3(4) . . . . ? C13 C14 C15 C16 -2.7(4) . . . . ? C14 C15 C16 C17 1.2(4) . . . . ? C15 C16 C17 C12 2.8(3) . . . . ? C15 C16 C17 C18 -175.6(2) . . . . ? C13 C12 C17 C16 -5.1(3) . . . . ? C1 C12 C17 C16 174.49(19) . . . . ? C13 C12 C17 C18 173.26(19) . . . . ? C1 C12 C17 C18 -7.1(3) . . . . ? C16 C17 C18 O2 -40.7(2) . . . . ? C12 C17 C18 O2 141.0(2) . . . . ? C16 C17 C18 C19 81.8(3) . . . . ? C12 C17 C18 C19 -96.5(2) . . . . ? O2 C18 C19 C22 56.6(2) . . . . ? C17 C18 C19 C22 -66.0(3) . . . . ? O2 C18 C19 C21 178.49(19) . . . . ? C17 C18 C19 C21 55.9(3) . . . . ? O2 C18 C19 C20 -63.8(2) . . . . ? C17 C18 C19 C20 173.61(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.126 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.032 # start Validation Reply Form _vrf_PLAT420_bcyct05_2 ; PROBLEM: D-H Without Acceptor O1 - *H12B ... ? RESPONSE: The hydrogen on the hydroxyl group can be considered to be disordered over two positions, the actual location of which may depends on the orientation of the molecules during crystallisation. ; data_bcyct04 _database_code_depnum_ccdc_archive 'CCDC 845648' #TrackingRef 'BCYCT04.cif' _audit_update_record ; 2011-09-22 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H22 O4' _chemical_formula_sum 'C20 H22 O4' _chemical_formula_weight 326.38 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 Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_space_group_name_Hall 'P 2 2ab' 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 9.4979(4) _cell_length_b 16.7194(6) _cell_length_c 5.6273(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 893.61(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3295 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 24.14 _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6054 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SAINT ver. 7.34; Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9507 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 27.59 _reflns_number_total 2045 _reflns_number_gt 1691 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. The flack parameter: _refine_ls_abs_structure_Flack -1(2) ; _chemical_absolute_configuration syn _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^)+(0.0460P)^2^+0.1071P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.067(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), 816 Friedel pairs' _refine_ls_number_reflns 1229 _refine_ls_number_parameters 112 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0941 _refine_ls_wR_factor_gt 0.0879 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.8668(2) 0.33696(10) 0.3643(4) 0.0520(5) Uani 1 1 d . . . H1A H 0.7992 0.3122 0.4587 0.062 Uiso 1 1 calc R . . C2 C 0.9471(2) 0.29137(11) 0.2124(4) 0.0603(6) Uani 1 1 d . . . H2A H 0.9334 0.2363 0.2056 0.072 Uiso 1 1 calc R . . C3 C 1.0466(2) 0.32620(11) 0.0716(4) 0.0557(5) Uani 1 1 d . . . H3A H 1.1003 0.2952 -0.0314 0.067 Uiso 1 1 calc R . . C4 C 1.0671(2) 0.40834(10) 0.0830(3) 0.0445(4) Uani 1 1 d . . . H4A H 1.1348 0.4321 -0.0132 0.053 Uiso 1 1 calc R . . C5 C 0.98779(17) 0.45576(9) 0.2362(3) 0.0366(4) Uani 1 1 d . . . C6 C 0.88489(18) 0.41949(9) 0.3794(3) 0.0388(4) Uani 1 1 d . . . C7 C 0.79571(19) 0.47071(9) 0.5411(3) 0.0410(4) Uani 1 1 d . . . H7A H 0.8566 0.5111 0.6143 0.049 Uiso 1 1 calc R . . C8 C 0.7159(2) 0.42845(13) 0.7362(4) 0.0559(5) Uani 1 1 d . . . H8A H 0.6663 0.4671 0.8306 0.084 Uiso 1 1 calc R . . H8B H 0.7809 0.3996 0.8349 0.084 Uiso 1 1 calc R . . H8C H 0.6498 0.3917 0.6672 0.084 Uiso 1 1 calc R . . O1 O 0.69535(14) 0.51184(7) 0.3843(2) 0.0475(3) Uani 1 1 d . . . C9 C 0.6593(2) 0.58676(12) 0.4424(4) 0.0548(5) Uani 1 1 d . . . O2 O 0.6971(2) 0.61845(9) 0.6231(3) 0.0862(6) Uani 1 1 d . . . C10 C 0.5701(2) 0.62408(14) 0.2577(5) 0.0697(6) Uani 1 1 d . . . H10A H 0.5360 0.6747 0.3139 0.105 Uiso 1 1 calc R . . H10B H 0.4918 0.5897 0.2231 0.105 Uiso 1 1 calc R . . H10C H 0.6246 0.6321 0.1160 0.105 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 C1 0.0617(11) 0.0378(9) 0.0564(11) 0.0033(9) 0.0038(11) -0.0115(8) C2 0.0818(14) 0.0309(9) 0.0683(13) -0.0063(9) -0.0005(13) -0.0062(9) C3 0.0675(12) 0.0410(9) 0.0586(11) -0.0119(9) 0.0027(11) 0.0047(9) C4 0.0518(9) 0.0403(9) 0.0415(9) -0.0021(8) 0.0034(8) -0.0025(8) C5 0.0437(8) 0.0318(8) 0.0343(8) -0.0001(7) -0.0034(8) -0.0019(7) C6 0.0449(9) 0.0353(8) 0.0361(8) 0.0013(7) -0.0039(8) -0.0044(7) C7 0.0443(9) 0.0423(8) 0.0365(8) 0.0013(7) -0.0011(8) -0.0023(8) C8 0.0555(11) 0.0663(12) 0.0458(10) 0.0060(10) 0.0048(10) -0.0059(10) O1 0.0499(7) 0.0480(7) 0.0445(6) 0.0017(6) -0.0024(6) 0.0029(6) C9 0.0584(12) 0.0534(11) 0.0524(11) 0.0011(10) 0.0067(10) 0.0116(9) O2 0.1154(14) 0.0714(10) 0.0717(10) -0.0240(9) -0.0172(12) 0.0395(10) C10 0.0677(13) 0.0723(14) 0.0691(14) 0.0159(13) 0.0054(13) 0.0190(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.376(3) . ? C1 C6 1.393(2) . ? C1 H1A 0.9300 . ? C2 C3 1.364(3) . ? C2 H2A 0.9300 . ? C3 C4 1.388(2) . ? C3 H3A 0.9300 . ? C4 C5 1.392(2) . ? C4 H4A 0.9300 . ? C5 C6 1.404(2) . ? C5 C5 1.498(3) 2_765 ? C6 C7 1.510(2) . ? C7 O1 1.470(2) . ? C7 C8 1.510(2) . ? C7 H7A 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? O1 C9 1.339(2) . ? C9 O2 1.201(3) . ? C9 C10 1.479(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 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 C2 C1 C6 121.20(18) . . ? C2 C1 H1A 119.4 . . ? C6 C1 H1A 119.4 . . ? C3 C2 C1 120.56(16) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C2 C3 C4 119.50(19) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C3 C4 C5 121.09(17) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C4 C5 C6 119.06(14) . . ? C4 C5 C5 118.61(14) . 2_765 ? C6 C5 C5 122.30(15) . 2_765 ? C1 C6 C5 118.60(16) . . ? C1 C6 C7 121.96(16) . . ? C5 C6 C7 119.43(14) . . ? O1 C7 C6 105.51(13) . . ? O1 C7 C8 109.27(15) . . ? C6 C7 C8 117.04(14) . . ? O1 C7 H7A 108.2 . . ? C6 C7 H7A 108.2 . . ? C8 C7 H7A 108.2 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C9 O1 C7 117.19(14) . . ? O2 C9 O1 122.87(19) . . ? O2 C9 C10 125.4(2) . . ? O1 C9 C10 111.68(19) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.2(3) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C3 C4 C5 C5 -178.50(17) . . . 2_765 ? C2 C1 C6 C5 -0.2(3) . . . . ? C2 C1 C6 C7 178.66(18) . . . . ? C4 C5 C6 C1 0.6(3) . . . . ? C5 C5 C6 C1 178.48(16) 2_765 . . . ? C4 C5 C6 C7 -178.33(16) . . . . ? C5 C5 C6 C7 -0.4(2) 2_765 . . . ? C1 C6 C7 O1 -104.55(19) . . . . ? C5 C6 C7 O1 74.33(18) . . . . ? C1 C6 C7 C8 17.2(3) . . . . ? C5 C6 C7 C8 -163.92(16) . . . . ? C6 C7 O1 C9 -144.64(15) . . . . ? C8 C7 O1 C9 88.71(18) . . . . ? C7 O1 C9 O2 -5.6(3) . . . . ? C7 O1 C9 C10 173.98(16) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.172 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.026 data_bcyct11 _database_code_depnum_ccdc_archive 'CCDC 894348' #TrackingRef 'BCYCT11.cif' _audit_update_record ; 2012-07-31 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H15 Br O' _chemical_formula_sum 'C11 H15 Br O' _chemical_formula_weight 243.14 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.6636(24) _cell_length_b 23.3522(52) _cell_length_c 11.4105(27) _cell_angle_alpha 90.00 _cell_angle_beta 114.8955(147) _cell_angle_gamma 90.00 _cell_volume 2335.7(10) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5672 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.23 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 3.483 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2140 _exptl_absorpt_correction_T_max 0.3512 _exptl_absorpt_process_details 'SAINT ver. 7.34; Bruker SADABS' _exptl_special_details ? _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 25743 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0775 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 24.71 _reflns_number_total 7887 _reflns_number_gt 4890 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _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. The quality of this set of data is relatively poor, especially in the high angle region where diffractions were very weak. As a result, some high angle data was discarded from the refinement. All protons were placed to their respective theoretical positions. O3-H3B should form a hydrogen bond intermolecularly with O2 (-X, 0.5+Y, -Z, ca 2.7A). There are two positions possible for H3B, pointing towards and away from O2, but for both locating using Fourier difference map and calculated position, it is pointing away from O2. It is conceivable that H3B could actually be pointed towards O2 to form the H-bond. This led to the B-level alert in checkcif. ; _chemical_absolute_configuration ad _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^)+(0.0412P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.004(9) _refine_ls_number_reflns 7887 _refine_ls_number_parameters 481 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0931 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0813 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.936 _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 Br1 Br 0.29627(8) 0.21553(2) 0.93688(6) 0.0862(2) Uani 1 1 d . . . O1 O -0.0428(4) 0.07588(14) 0.8607(3) 0.0573(9) Uani 1 1 d . . . H1A H -0.0553 0.0810 0.7857 0.086 Uiso 1 1 calc R . . C1 C 0.3286(7) 0.1358(2) 0.9192(5) 0.0558(15) Uani 1 1 d . . . C2 C 0.4561(8) 0.1220(3) 0.8982(6) 0.0748(18) Uani 1 1 d . . . H2A H 0.5241 0.1503 0.8991 0.090 Uiso 1 1 calc R . . C3 C 0.4801(9) 0.0664(4) 0.8763(6) 0.088(2) Uani 1 1 d . . . H3A H 0.5650 0.0568 0.8618 0.106 Uiso 1 1 calc R . . C4 C 0.3810(9) 0.0243(3) 0.8752(6) 0.0782(19) Uani 1 1 d . . . H4A H 0.3970 -0.0136 0.8588 0.094 Uiso 1 1 calc R . . C5 C 0.2584(7) 0.0389(3) 0.8986(5) 0.0591(16) Uani 1 1 d . . . H5A H 0.1929 0.0100 0.9000 0.071 Uiso 1 1 calc R . . C6 C 0.2263(6) 0.0951(2) 0.9207(4) 0.0447(13) Uani 1 1 d . . . C7 C 0.0848(6) 0.1086(2) 0.9452(5) 0.0511(14) Uani 1 1 d . . . H7A H 0.0601 0.1492 0.9249 0.061 Uiso 1 1 calc R . . C8 C 0.1019(7) 0.0982(2) 1.0858(5) 0.0591(15) Uani 1 1 d . . . C9 C -0.0408(9) 0.1228(4) 1.0949(7) 0.104(2) Uani 1 1 d . . . H9A H -0.1271 0.0989 1.0471 0.156 Uiso 1 1 calc R . . H9B H -0.0595 0.1608 1.0596 0.156 Uiso 1 1 calc R . . H9C H -0.0248 0.1241 1.1838 0.156 Uiso 1 1 calc R . . C10 C 0.1168(8) 0.0355(3) 1.1187(6) 0.087(2) Uani 1 1 d . . . H10A H 0.0297 0.0153 1.0576 0.131 Uiso 1 1 calc R . . H10B H 0.1224 0.0304 1.2041 0.131 Uiso 1 1 calc R . . H10C H 0.2079 0.0207 1.1155 0.131 Uiso 1 1 calc R . . C11 C 0.2426(8) 0.1306(3) 1.1803(6) 0.086(2) Uani 1 1 d . . . H11A H 0.2529 0.1250 1.2669 0.129 Uiso 1 1 calc R . . H11B H 0.2312 0.1707 1.1600 0.129 Uiso 1 1 calc R . . H11C H 0.3320 0.1164 1.1732 0.129 Uiso 1 1 calc R . . Br2 Br 0.63523(9) 0.20339(3) 0.23388(6) 0.0975(3) Uani 1 1 d . . . O2 O 0.7780(4) 0.10885(13) 0.6083(3) 0.0573(10) Uani 1 1 d . . . H2B H 0.8137 0.0859 0.5741 0.086 Uiso 1 1 calc R . . C12 C 0.8277(6) 0.2037(2) 0.3750(5) 0.0569(14) Uani 1 1 d . . . C13 C 0.9506(9) 0.2244(2) 0.3515(6) 0.0726(18) Uani 1 1 d . . . H13A H 0.9338 0.2379 0.2699 0.087 Uiso 1 1 calc R . . C14 C 1.0940(8) 0.2245(3) 0.4483(8) 0.0789(19) Uani 1 1 d . . . H14A H 1.1747 0.2386 0.4328 0.095 Uiso 1 1 calc R . . C15 C 1.1205(6) 0.2041(3) 0.5679(7) 0.0760(18) Uani 1 1 d . . . H15A H 1.2191 0.2038 0.6331 0.091 Uiso 1 1 calc R . . C16 C 1.0003(7) 0.1839(2) 0.5918(6) 0.0587(15) Uani 1 1 d . . . H16A H 1.0198 0.1709 0.6743 0.070 Uiso 1 1 calc R . . C17 C 0.8496(6) 0.1824(2) 0.4958(5) 0.0452(12) Uani 1 1 d . . . C18 C 0.7245(6) 0.1587(2) 0.5275(5) 0.0470(13) Uani 1 1 d . . . H18A H 0.6411 0.1466 0.4463 0.056 Uiso 1 1 calc R . . C19 C 0.6574(6) 0.2001(2) 0.5949(5) 0.0552(14) Uani 1 1 d . . . C20 C 0.5998(9) 0.2544(3) 0.5159(8) 0.098(2) Uani 1 1 d . . . H20A H 0.6838 0.2742 0.5101 0.146 Uiso 1 1 calc R . . H20B H 0.5531 0.2787 0.5569 0.146 Uiso 1 1 calc R . . H20C H 0.5261 0.2446 0.4307 0.146 Uiso 1 1 calc R . . C21 C 0.5188(8) 0.1686(3) 0.6050(8) 0.104(3) Uani 1 1 d . . . H21A H 0.4715 0.1937 0.6439 0.156 Uiso 1 1 calc R . . H21B H 0.5546 0.1348 0.6570 0.156 Uiso 1 1 calc R . . H21C H 0.4458 0.1580 0.5201 0.156 Uiso 1 1 calc R . . C22 C 0.7694(7) 0.2147(3) 0.7295(6) 0.0819(19) Uani 1 1 d . . . H22A H 0.8568 0.2331 0.7266 0.123 Uiso 1 1 calc R . . H22B H 0.8009 0.1803 0.7798 0.123 Uiso 1 1 calc R . . H22C H 0.7223 0.2401 0.7681 0.123 Uiso 1 1 calc R . . Br3 Br 0.97633(10) 0.35584(3) 0.56715(7) 0.0950(3) Uani 1 1 d . . . O3 O 1.2156(5) 0.49958(14) 0.4788(3) 0.0605(10) Uani 1 1 d . . . H3B H 1.3047 0.4936 0.4922 0.091 Uiso 1 1 calc R . . C23 C 0.9144(9) 0.4342(3) 0.5422(5) 0.0665(17) Uani 1 1 d . . . C24 C 0.7627(10) 0.4463(4) 0.5179(6) 0.086(2) Uani 1 1 d . . . H24A H 0.6980 0.4167 0.5178 0.103 Uiso 1 1 calc R . . C25 C 0.7097(9) 0.5006(5) 0.4947(6) 0.092(2) Uani 1 1 d . . . H25A H 0.6099 0.5086 0.4812 0.111 Uiso 1 1 calc R . . C26 C 0.8029(10) 0.5433(4) 0.4911(7) 0.089(2) Uani 1 1 d . . . H26A H 0.7658 0.5805 0.4712 0.107 Uiso 1 1 calc R . . C27 C 0.9532(8) 0.5315(3) 0.5171(6) 0.0681(17) Uani 1 1 d . . . H27A H 1.0161 0.5616 0.5168 0.082 Uiso 1 1 calc R . . C28 C 1.0137(7) 0.4774(2) 0.5433(5) 0.0534(15) Uani 1 1 d . . . C29 C 1.1786(7) 0.4669(2) 0.5699(5) 0.0544(15) Uani 1 1 d . . . H29A H 1.1885 0.4262 0.5534 0.065 Uiso 1 1 calc R . . C30 C 1.2959(7) 0.4799(2) 0.7070(5) 0.0604(16) Uani 1 1 d . . . C31 C 1.2540(9) 0.4475(3) 0.8044(6) 0.096(2) Uani 1 1 d . . . H31A H 1.1509 0.4564 0.7893 0.144 Uiso 1 1 calc R . . H31B H 1.3217 0.4587 0.8906 0.144 Uiso 1 1 calc R . . H31C H 1.2634 0.4071 0.7944 0.144 Uiso 1 1 calc R . . C32 C 1.3090(9) 0.5426(3) 0.7366(6) 0.093(2) Uani 1 1 d . . . H32A H 1.2126 0.5569 0.7295 0.139 Uiso 1 1 calc R . . H32B H 1.3376 0.5624 0.6764 0.139 Uiso 1 1 calc R . . H32C H 1.3853 0.5487 0.8228 0.139 Uiso 1 1 calc R . . C33 C 1.4529(8) 0.4571(4) 0.7178(7) 0.108(3) Uani 1 1 d . . . H33A H 1.4835 0.4786 0.6609 0.162 Uiso 1 1 calc R . . H33B H 1.4433 0.4174 0.6938 0.162 Uiso 1 1 calc R . . H33C H 1.5282 0.4613 0.8051 0.162 Uiso 1 1 calc R . . Br4 Br 0.89420(11) 0.37445(3) -0.15129(7) 0.1029(3) Uani 1 1 d . . . O4 O 1.1272(4) 0.46562(14) 0.2253(3) 0.0579(10) Uani 1 1 d . . . H4B H 1.0566 0.4884 0.1929 0.087 Uiso 1 1 calc R . . C34 C 0.8485(7) 0.3710(2) -0.0053(6) 0.0592(14) Uani 1 1 d . . . C35 C 0.7064(8) 0.3462(3) -0.0284(7) 0.0777(19) Uani 1 1 d . . . H35A H 0.6439 0.3321 -0.1100 0.093 Uiso 1 1 calc R . . C36 C 0.6610(8) 0.3429(3) 0.0701(8) 0.088(2) Uani 1 1 d . . . H36A H 0.5678 0.3262 0.0559 0.105 Uiso 1 1 calc R . . C37 C 0.7535(8) 0.3641(3) 0.1897(7) 0.0770(18) Uani 1 1 d . . . H37A H 0.7221 0.3627 0.2563 0.092 Uiso 1 1 calc R . . C38 C 0.8921(7) 0.3875(2) 0.2109(5) 0.0562(14) Uani 1 1 d . . . H38A H 0.9539 0.4012 0.2930 0.067 Uiso 1 1 calc R . . C39 C 0.9448(6) 0.39144(18) 0.1128(5) 0.0430(12) Uani 1 1 d . . . C40 C 1.1007(6) 0.4172(2) 0.1434(5) 0.0469(13) Uani 1 1 d . . . H40A H 1.1010 0.4304 0.0619 0.056 Uiso 1 1 calc R . . C41 C 1.2376(6) 0.3762(2) 0.2084(5) 0.0584(15) Uani 1 1 d . . . C42 C 1.2652(8) 0.3621(3) 0.3457(6) 0.091(2) Uani 1 1 d . . . H42A H 1.1746 0.3456 0.3465 0.137 Uiso 1 1 calc R . . H42B H 1.2910 0.3964 0.3966 0.137 Uiso 1 1 calc R . . H42C H 1.3477 0.3352 0.3812 0.137 Uiso 1 1 calc R . . C43 C 1.3809(8) 0.4065(3) 0.2135(8) 0.107(3) Uani 1 1 d . . . H43A H 1.4663 0.3808 0.2480 0.161 Uiso 1 1 calc R . . H43B H 1.4012 0.4397 0.2678 0.161 Uiso 1 1 calc R . . H43C H 1.3649 0.4180 0.1279 0.161 Uiso 1 1 calc R . . C44 C 1.2125(10) 0.3222(3) 0.1279(9) 0.121(3) Uani 1 1 d . . . H44A H 1.1174 0.3049 0.1163 0.181 Uiso 1 1 calc R . . H44B H 1.2943 0.2958 0.1714 0.181 Uiso 1 1 calc R . . H44C H 1.2097 0.3318 0.0451 0.181 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 Br1 0.1035(5) 0.0571(4) 0.0844(4) -0.0107(3) 0.0262(4) -0.0237(4) O1 0.056(2) 0.056(2) 0.048(2) -0.0099(18) 0.0104(19) -0.0044(19) C1 0.064(4) 0.062(4) 0.033(3) -0.001(3) 0.013(3) -0.009(3) C2 0.075(5) 0.092(6) 0.051(4) -0.003(3) 0.020(4) -0.019(4) C3 0.079(5) 0.124(7) 0.067(4) -0.008(5) 0.037(4) 0.016(5) C4 0.087(5) 0.077(5) 0.079(5) -0.015(4) 0.043(4) -0.005(4) C5 0.063(4) 0.064(4) 0.052(3) 0.000(3) 0.025(3) -0.005(3) C6 0.051(4) 0.042(3) 0.032(3) -0.005(2) 0.010(3) -0.002(3) C7 0.061(4) 0.038(3) 0.044(3) -0.006(2) 0.013(3) -0.003(3) C8 0.064(4) 0.064(4) 0.044(3) -0.008(3) 0.017(3) -0.005(3) C9 0.098(6) 0.132(7) 0.093(6) -0.014(5) 0.052(5) 0.005(5) C10 0.120(6) 0.076(5) 0.065(4) 0.010(4) 0.039(4) -0.005(4) C11 0.097(5) 0.102(5) 0.048(4) -0.011(4) 0.020(4) -0.034(4) Br2 0.1003(6) 0.0961(6) 0.0636(4) 0.0231(4) 0.0027(4) -0.0217(4) O2 0.080(3) 0.039(2) 0.051(2) 0.0085(16) 0.026(2) 0.0040(18) C12 0.060(4) 0.045(3) 0.061(3) 0.009(3) 0.021(3) 0.002(3) C13 0.106(6) 0.053(4) 0.074(4) 0.009(3) 0.052(5) 0.004(4) C14 0.063(5) 0.089(5) 0.101(5) 0.004(4) 0.050(5) -0.009(4) C15 0.041(4) 0.096(5) 0.085(5) 0.000(4) 0.021(3) -0.003(4) C16 0.051(4) 0.065(4) 0.065(4) 0.008(3) 0.030(4) 0.010(3) C17 0.041(3) 0.038(3) 0.051(3) 0.002(2) 0.014(3) 0.003(2) C18 0.042(3) 0.042(3) 0.045(3) 0.010(2) 0.006(3) -0.004(2) C19 0.042(3) 0.056(3) 0.068(4) 0.006(3) 0.023(3) 0.005(3) C20 0.104(6) 0.070(5) 0.120(6) 0.031(4) 0.048(5) 0.045(4) C21 0.067(5) 0.137(7) 0.119(6) 0.010(5) 0.050(5) -0.013(4) C22 0.088(5) 0.065(4) 0.106(5) -0.015(4) 0.054(4) 0.022(4) Br3 0.1488(8) 0.0619(4) 0.0925(5) -0.0108(4) 0.0685(5) -0.0374(4) O3 0.081(3) 0.057(2) 0.050(2) 0.0057(18) 0.034(2) -0.0071(19) C23 0.088(5) 0.071(4) 0.040(3) -0.012(3) 0.027(4) -0.021(4) C24 0.072(6) 0.120(7) 0.060(4) -0.014(4) 0.023(4) -0.039(5) C25 0.064(5) 0.140(8) 0.067(5) -0.001(5) 0.022(4) 0.002(6) C26 0.089(6) 0.101(6) 0.073(5) 0.005(4) 0.031(5) 0.011(5) C27 0.072(5) 0.075(5) 0.059(4) 0.001(3) 0.029(4) -0.001(4) C28 0.076(4) 0.053(4) 0.028(3) -0.005(2) 0.019(3) -0.014(4) C29 0.074(4) 0.046(3) 0.053(4) -0.001(3) 0.037(3) -0.005(3) C30 0.064(4) 0.070(4) 0.043(3) 0.011(3) 0.018(3) -0.001(3) C31 0.112(6) 0.117(6) 0.053(4) 0.009(4) 0.029(4) -0.040(5) C32 0.116(6) 0.072(5) 0.058(4) -0.008(3) 0.004(4) -0.024(4) C33 0.082(6) 0.144(7) 0.090(6) 0.024(5) 0.029(5) 0.013(5) Br4 0.1474(8) 0.1049(6) 0.0680(4) -0.0276(4) 0.0567(5) -0.0415(5) O4 0.075(3) 0.045(2) 0.045(2) -0.0058(17) 0.017(2) 0.0091(18) C34 0.076(4) 0.036(3) 0.074(4) -0.007(3) 0.040(4) -0.004(3) C35 0.081(5) 0.061(4) 0.080(5) -0.013(3) 0.023(4) -0.009(4) C36 0.063(5) 0.095(6) 0.103(6) 0.009(5) 0.033(5) -0.005(4) C37 0.070(5) 0.093(5) 0.087(5) 0.015(4) 0.052(4) 0.008(4) C38 0.056(4) 0.058(4) 0.059(3) 0.000(3) 0.028(3) 0.005(3) C39 0.049(3) 0.031(3) 0.047(3) -0.004(2) 0.019(3) 0.002(2) C40 0.064(4) 0.039(3) 0.044(3) -0.003(2) 0.029(3) -0.003(3) C41 0.051(4) 0.056(3) 0.079(4) -0.003(3) 0.037(3) 0.004(3) C42 0.088(5) 0.084(5) 0.100(5) 0.043(4) 0.038(4) 0.043(4) C43 0.071(5) 0.154(7) 0.108(6) -0.001(5) 0.049(5) -0.002(5) C44 0.115(7) 0.074(5) 0.176(9) -0.034(5) 0.064(6) 0.039(5) _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 Br1 C1 1.913(6) . ? O1 C7 1.426(6) . ? O1 H1A 0.8200 . ? C1 C6 1.376(7) . ? C1 C2 1.388(8) . ? C2 C3 1.361(9) . ? C2 H2A 0.9300 . ? C3 C4 1.368(9) . ? C3 H3A 0.9300 . ? C4 C5 1.363(8) . ? C4 H4A 0.9300 . ? C5 C6 1.397(7) . ? C5 H5A 0.9300 . ? C6 C7 1.538(7) . ? C7 C8 1.561(7) . ? C7 H7A 0.9800 . ? C8 C10 1.504(8) . ? C8 C11 1.533(8) . ? C8 C9 1.538(8) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? Br2 C12 1.879(5) . ? O2 C18 1.439(6) . ? O2 H2B 0.8200 . ? C12 C17 1.395(7) . ? C12 C13 1.409(8) . ? C13 C14 1.361(9) . ? C13 H13A 0.9300 . ? C14 C15 1.364(9) . ? C14 H14A 0.9300 . ? C15 C16 1.383(8) . ? C15 H15A 0.9300 . ? C16 C17 1.407(7) . ? C16 H16A 0.9300 . ? C17 C18 1.506(7) . ? C18 C19 1.539(7) . ? C18 H18A 0.9800 . ? C19 C22 1.499(8) . ? C19 C20 1.519(8) . ? C19 C21 1.574(8) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? Br3 C23 1.909(7) . ? O3 C29 1.451(6) . ? O3 H3B 0.8200 . ? C23 C28 1.390(8) . ? C23 C24 1.401(10) . ? C24 C25 1.352(10) . ? C24 H24A 0.9300 . ? C25 C26 1.356(10) . ? C25 H25A 0.9300 . ? C26 C27 1.382(9) . ? C26 H26A 0.9300 . ? C27 C28 1.370(8) . ? C27 H27A 0.9300 . ? C28 C29 1.512(8) . ? C29 C30 1.528(8) . ? C29 H29A 0.9800 . ? C30 C32 1.495(8) . ? C30 C31 1.533(8) . ? C30 C33 1.564(8) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? Br4 C34 1.896(5) . ? O4 C40 1.419(6) . ? O4 H4B 0.8200 . ? C34 C39 1.361(7) . ? C34 C35 1.410(8) . ? C35 C36 1.370(9) . ? C35 H35A 0.9300 . ? C36 C37 1.371(9) . ? C36 H36A 0.9300 . ? C37 C38 1.370(8) . ? C37 H37A 0.9300 . ? C38 C39 1.415(7) . ? C38 H38A 0.9300 . ? C39 C40 1.521(7) . ? C40 C41 1.547(7) . ? C40 H40A 0.9800 . ? C41 C42 1.510(8) . ? C41 C44 1.517(9) . ? C41 C43 1.535(8) . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 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 C7 O1 H1A 109.5 . . ? C6 C1 C2 122.4(5) . . ? C6 C1 Br1 121.3(4) . . ? C2 C1 Br1 116.2(5) . . ? C3 C2 C1 119.1(6) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 121.0(7) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C5 C4 C3 118.8(6) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C4 C5 C6 123.2(6) . . ? C4 C5 H5A 118.4 . . ? C6 C5 H5A 118.4 . . ? C1 C6 C5 115.5(5) . . ? C1 C6 C7 124.0(5) . . ? C5 C6 C7 120.5(5) . . ? O1 C7 C6 110.4(4) . . ? O1 C7 C8 107.4(4) . . ? C6 C7 C8 115.9(4) . . ? O1 C7 H7A 107.6 . . ? C6 C7 H7A 107.6 . . ? C8 C7 H7A 107.6 . . ? C10 C8 C11 110.0(5) . . ? C10 C8 C9 109.9(5) . . ? C11 C8 C9 108.9(5) . . ? C10 C8 C7 111.5(4) . . ? C11 C8 C7 109.0(4) . . ? C9 C8 C7 107.6(5) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C18 O2 H2B 109.5 . . ? C17 C12 C13 121.4(5) . . ? C17 C12 Br2 121.9(4) . . ? C13 C12 Br2 116.6(4) . . ? C14 C13 C12 119.9(5) . . ? C14 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? C13 C14 C15 120.6(6) . . ? C13 C14 H14A 119.7 . . ? C15 C14 H14A 119.7 . . ? C14 C15 C16 119.8(6) . . ? C14 C15 H15A 120.1 . . ? C16 C15 H15A 120.1 . . ? C15 C16 C17 122.3(5) . . ? C15 C16 H16A 118.8 . . ? C17 C16 H16A 118.8 . . ? C12 C17 C16 115.9(5) . . ? C12 C17 C18 124.4(5) . . ? C16 C17 C18 119.6(5) . . ? O2 C18 C17 110.1(4) . . ? O2 C18 C19 107.5(4) . . ? C17 C18 C19 116.0(4) . . ? O2 C18 H18A 107.6 . . ? C17 C18 H18A 107.6 . . ? C19 C18 H18A 107.6 . . ? C22 C19 C20 110.2(5) . . ? C22 C19 C18 112.3(4) . . ? C20 C19 C18 110.7(5) . . ? C22 C19 C21 107.6(5) . . ? C20 C19 C21 108.9(5) . . ? C18 C19 C21 107.0(5) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C29 O3 H3B 109.5 . . ? C28 C23 C24 121.1(6) . . ? C28 C23 Br3 121.5(6) . . ? C24 C23 Br3 117.3(6) . . ? C25 C24 C23 120.4(7) . . ? C25 C24 H24A 119.8 . . ? C23 C24 H24A 119.8 . . ? C24 C25 C26 119.7(7) . . ? C24 C25 H25A 120.2 . . ? C26 C25 H25A 120.2 . . ? C25 C26 C27 119.8(7) . . ? C25 C26 H26A 120.1 . . ? C27 C26 H26A 120.1 . . ? C28 C27 C26 123.0(6) . . ? C28 C27 H27A 118.5 . . ? C26 C27 H27A 118.5 . . ? C27 C28 C23 116.0(6) . . ? C27 C28 C29 120.7(5) . . ? C23 C28 C29 123.3(6) . . ? O3 C29 C28 109.1(4) . . ? O3 C29 C30 109.1(4) . . ? C28 C29 C30 116.0(4) . . ? O3 C29 H29A 107.4 . . ? C28 C29 H29A 107.4 . . ? C30 C29 H29A 107.4 . . ? C32 C30 C29 112.5(5) . . ? C32 C30 C31 110.1(5) . . ? C29 C30 C31 109.6(5) . . ? C32 C30 C33 109.2(6) . . ? C29 C30 C33 106.8(5) . . ? C31 C30 C33 108.5(5) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C40 O4 H4B 109.5 . . ? C39 C34 C35 122.4(5) . . ? C39 C34 Br4 122.7(4) . . ? C35 C34 Br4 114.9(5) . . ? C36 C35 C34 119.5(6) . . ? C36 C35 H35A 120.2 . . ? C34 C35 H35A 120.2 . . ? C35 C36 C37 119.8(6) . . ? C35 C36 H36A 120.1 . . ? C37 C36 H36A 120.1 . . ? C38 C37 C36 120.0(6) . . ? C38 C37 H37A 120.0 . . ? C36 C37 H37A 120.0 . . ? C37 C38 C39 122.5(5) . . ? C37 C38 H38A 118.8 . . ? C39 C38 H38A 118.8 . . ? C34 C39 C38 115.9(5) . . ? C34 C39 C40 124.4(4) . . ? C38 C39 C40 119.8(4) . . ? O4 C40 C39 110.7(4) . . ? O4 C40 C41 107.3(4) . . ? C39 C40 C41 115.4(4) . . ? O4 C40 H40A 107.7 . . ? C39 C40 H40A 107.7 . . ? C41 C40 H40A 107.7 . . ? C42 C41 C44 111.1(6) . . ? C42 C41 C43 107.3(5) . . ? C44 C41 C43 108.6(5) . . ? C42 C41 C40 112.0(4) . . ? C44 C41 C40 109.8(5) . . ? C43 C41 C40 107.9(5) . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C41 C43 H43A 109.5 . . ? C41 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C41 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C41 C44 H44A 109.5 . . ? C41 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C41 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.0(9) . . . . ? Br1 C1 C2 C3 -175.7(5) . . . . ? C1 C2 C3 C4 -0.2(10) . . . . ? C2 C3 C4 C5 -1.1(10) . . . . ? C3 C4 C5 C6 1.6(9) . . . . ? C2 C1 C6 C5 -0.5(7) . . . . ? Br1 C1 C6 C5 176.0(4) . . . . ? C2 C1 C6 C7 179.3(5) . . . . ? Br1 C1 C6 C7 -4.2(7) . . . . ? C4 C5 C6 C1 -0.9(8) . . . . ? C4 C5 C6 C7 179.3(5) . . . . ? C1 C6 C7 O1 139.2(5) . . . . ? C5 C6 C7 O1 -41.1(6) . . . . ? C1 C6 C7 C8 -98.5(6) . . . . ? C5 C6 C7 C8 81.3(6) . . . . ? O1 C7 C8 C10 55.9(6) . . . . ? C6 C7 C8 C10 -68.1(6) . . . . ? O1 C7 C8 C11 177.4(5) . . . . ? C6 C7 C8 C11 53.5(6) . . . . ? O1 C7 C8 C9 -64.7(6) . . . . ? C6 C7 C8 C9 171.3(5) . . . . ? C17 C12 C13 C14 -0.7(8) . . . . ? Br2 C12 C13 C14 -178.4(5) . . . . ? C12 C13 C14 C15 0.8(10) . . . . ? C13 C14 C15 C16 -1.0(10) . . . . ? C14 C15 C16 C17 1.3(9) . . . . ? C13 C12 C17 C16 0.9(7) . . . . ? Br2 C12 C17 C16 178.4(4) . . . . ? C13 C12 C17 C18 -178.9(5) . . . . ? Br2 C12 C17 C18 -1.4(7) . . . . ? C15 C16 C17 C12 -1.2(8) . . . . ? C15 C16 C17 C18 178.6(5) . . . . ? C12 C17 C18 O2 139.7(5) . . . . ? C16 C17 C18 O2 -40.2(6) . . . . ? C12 C17 C18 C19 -97.9(6) . . . . ? C16 C17 C18 C19 82.2(6) . . . . ? O2 C18 C19 C22 55.7(6) . . . . ? C17 C18 C19 C22 -68.0(6) . . . . ? O2 C18 C19 C20 179.4(5) . . . . ? C17 C18 C19 C20 55.6(6) . . . . ? O2 C18 C19 C21 -62.1(5) . . . . ? C17 C18 C19 C21 174.1(5) . . . . ? C28 C23 C24 C25 0.2(9) . . . . ? Br3 C23 C24 C25 -177.5(5) . . . . ? C23 C24 C25 C26 1.9(10) . . . . ? C24 C25 C26 C27 -3.0(11) . . . . ? C25 C26 C27 C28 2.0(10) . . . . ? C26 C27 C28 C23 0.1(8) . . . . ? C26 C27 C28 C29 179.4(5) . . . . ? C24 C23 C28 C27 -1.2(8) . . . . ? Br3 C23 C28 C27 176.4(4) . . . . ? C24 C23 C28 C29 179.6(5) . . . . ? Br3 C23 C28 C29 -2.8(7) . . . . ? C27 C28 C29 O3 -42.6(6) . . . . ? C23 C28 C29 O3 136.6(5) . . . . ? C27 C28 C29 C30 81.1(6) . . . . ? C23 C28 C29 C30 -99.7(6) . . . . ? O3 C29 C30 C32 54.9(6) . . . . ? C28 C29 C30 C32 -68.8(6) . . . . ? O3 C29 C30 C31 177.7(5) . . . . ? C28 C29 C30 C31 54.0(7) . . . . ? O3 C29 C30 C33 -64.9(6) . . . . ? C28 C29 C30 C33 171.4(5) . . . . ? C39 C34 C35 C36 0.9(9) . . . . ? Br4 C34 C35 C36 -178.5(5) . . . . ? C34 C35 C36 C37 0.6(10) . . . . ? C35 C36 C37 C38 -1.4(10) . . . . ? C36 C37 C38 C39 0.9(9) . . . . ? C35 C34 C39 C38 -1.4(7) . . . . ? Br4 C34 C39 C38 178.0(4) . . . . ? C35 C34 C39 C40 178.4(5) . . . . ? Br4 C34 C39 C40 -2.2(7) . . . . ? C37 C38 C39 C34 0.5(7) . . . . ? C37 C38 C39 C40 -179.3(5) . . . . ? C34 C39 C40 O4 139.8(5) . . . . ? C38 C39 C40 O4 -40.3(6) . . . . ? C34 C39 C40 C41 -98.1(6) . . . . ? C38 C39 C40 C41 81.7(5) . . . . ? O4 C40 C41 C42 53.6(6) . . . . ? C39 C40 C41 C42 -70.3(6) . . . . ? O4 C40 C41 C44 177.5(5) . . . . ? C39 C40 C41 C44 53.6(6) . . . . ? O4 C40 C41 C43 -64.3(5) . . . . ? C39 C40 C41 C43 171.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.284 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.052 # start Validation Reply Form _vrf_PLAT420_bcyct11 ; PROBLEM: D-H Without Acceptor O3 - H3B ... ? RESPONSE: O3-H3B should form a hydrogen bond intermolecularly with O2 (-X, 0.5+Y, -Z, ca 2.7A). There are two positions possible for H3B, pointing towards and away from O2, but for both locating using Fourier difference map and calculated position, it is pointing away from O2. It is conceivable that H3B could actually be pointed towards O2 to form the H-bond. ; data_bcyct13 _database_code_depnum_ccdc_archive 'CCDC 894349' #TrackingRef 'BCYCT13.cif' _audit_update_record ; 2012-07-31 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 O2' _chemical_formula_sum 'C16 H18 O2' _chemical_formula_weight 242.30 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 19.2144(6) _cell_length_b 13.7947(4) _cell_length_c 23.5076(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.5958(16) _cell_angle_gamma 90.00 _cell_volume 5971.3(3) _cell_formula_units_Z 16 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7801 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 21.38 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.56 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.078 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9620 _exptl_absorpt_correction_T_max 0.9821 _exptl_absorpt_process_details 'SAINT ver. 7.34; Bruker SADABS' _exptl_special_details ? _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 47181 _diffrn_reflns_av_R_equivalents 0.0808 _diffrn_reflns_av_sigmaI/netI 0.0731 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 25.00 _reflns_number_total 10402 _reflns_number_gt 6495 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _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. The high angle data is poor for this crystal sample, and the diffraction intensity was quite weak. This led to a relatively high R-factor following refinement. There appears to be a highly disordered solvent molecule in the asymmetric unit (CDCl3), and PLATON/SQUEEZE was used to remove it from refineme All hydroxyl protons were initially located using the Fourier difference map, then either had their position fixed using AFIX or restrained with DFIX. The remaining protons were refined using their respective riding model. ; _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^)+(0.1885P)^2^+0.6559P] 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 10402 _refine_ls_number_parameters 675 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1185 _refine_ls_R_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.3044 _refine_ls_wR_factor_gt 0.2584 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.107 -0.155 0.308 176 62 ' ' 2 -0.107 0.155 0.692 176 62 ' ' 3 0.578 0.042 0.825 8 1 ' ' 4 0.392 0.345 0.192 176 62 ' ' 5 0.608 0.654 0.808 175 62 ' ' 6 0.077 0.452 0.325 7 0 ' ' 7 0.923 0.548 0.675 7 0 ' ' 8 0.423 0.952 0.175 7 0 ' ' _platon_squeeze_details ; ; 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 0.1407(2) 0.8493(2) 0.45316(15) 0.0856(9) Uani 1 1 d D . . H1 H 0.102(2) 0.844(5) 0.425(2) 0.128 Uiso 1 1 d D . . C11 C 0.08958(19) 0.8238(2) 0.58796(14) 0.0500(8) Uani 1 1 d . . . C12 C 0.0439(2) 0.7671(3) 0.61071(19) 0.0702(10) Uani 1 1 d . . . H12A H 0.0545 0.7595 0.6516 0.084 Uiso 1 1 calc R . . C13 C -0.0165(2) 0.7217(3) 0.5746(2) 0.0738(11) Uani 1 1 d . . . H13A H -0.0471 0.6857 0.5908 0.089 Uiso 1 1 calc R . . C14 C -0.0308(2) 0.7309(3) 0.5138(2) 0.0702(11) Uani 1 1 d . . . H14A H -0.0699 0.6981 0.4887 0.084 Uiso 1 1 calc R . . C15 C 0.01241(18) 0.7880(3) 0.49014(16) 0.0557(8) Uani 1 1 d . . . H15A H 0.0003 0.7960 0.4492 0.067 Uiso 1 1 calc R . . C16 C 0.07352(17) 0.8341(2) 0.52554(13) 0.0462(7) Uani 1 1 d . . . C17 C 0.12005(19) 0.8970(3) 0.49910(14) 0.0552(8) Uani 1 1 d . . . H17A H 0.1645 0.9122 0.5306 0.066 Uiso 1 1 calc R . . C18 C 0.0840(3) 0.9919(3) 0.4753(2) 0.0797(12) Uani 1 1 d . . . H18A H 0.1174 1.0314 0.4620 0.120 Uiso 1 1 calc R . . H18B H 0.0699 1.0252 0.5061 0.120 Uiso 1 1 calc R . . H18C H 0.0418 0.9794 0.4426 0.120 Uiso 1 1 calc R . . O2 O 0.30591(15) 0.7373(2) 0.60502(14) 0.0706(7) Uani 1 1 d D . . H2 H 0.290(4) 0.772(4) 0.5740(18) 0.13(2) Uiso 1 1 d D . . C21 C 0.15355(19) 0.8723(2) 0.62997(14) 0.0507(8) Uani 1 1 d . . . C22 C 0.1431(2) 0.9585(3) 0.65586(18) 0.0719(11) Uani 1 1 d . . . H22A H 0.0967 0.9853 0.6461 0.086 Uiso 1 1 calc R . . C23 C 0.1996(3) 1.0064(3) 0.6961(2) 0.0858(14) Uani 1 1 d . . . H23A H 0.1915 1.0652 0.7125 0.103 Uiso 1 1 calc R . . C24 C 0.2666(3) 0.9663(3) 0.71112(17) 0.0753(12) Uani 1 1 d . . . H24A H 0.3047 0.9973 0.7385 0.090 Uiso 1 1 calc R . . C25 C 0.2790(2) 0.8791(3) 0.68598(16) 0.0650(10) Uani 1 1 d . . . H25A H 0.3252 0.8519 0.6970 0.078 Uiso 1 1 calc R . . C26 C 0.22293(19) 0.8323(2) 0.64468(14) 0.0501(8) Uani 1 1 d . . . C27 C 0.2371(2) 0.7374(2) 0.61829(17) 0.0564(8) Uani 1 1 d . . . H27A H 0.1982 0.7255 0.5816 0.068 Uiso 1 1 calc R . . C28 C 0.2400(4) 0.6535(3) 0.6607(3) 0.0990(17) Uani 1 1 d . . . H28A H 0.2385 0.5934 0.6398 0.149 Uiso 1 1 calc R . . H28B H 0.1991 0.6571 0.6764 0.149 Uiso 1 1 calc R . . H28C H 0.2841 0.6571 0.6926 0.149 Uiso 1 1 calc R . . O3 O 0.25224(16) 0.7857(2) 0.37099(14) 0.0765(8) Uani 1 1 d . . . H3 H 0.2254 0.7489 0.3823 0.115 Uiso 1 1 calc R . . C31 C 0.42039(18) 0.6728(2) 0.40081(15) 0.0480(7) Uani 1 1 d . . . C32 C 0.49371(19) 0.6919(3) 0.4276(2) 0.0658(10) Uani 1 1 d . . . H32A H 0.5238 0.6430 0.4481 0.079 Uiso 1 1 calc R . . C33 C 0.5222(2) 0.7833(3) 0.4237(2) 0.0700(11) Uani 1 1 d . . . H33A H 0.5713 0.7951 0.4409 0.084 Uiso 1 1 calc R . . C34 C 0.4781(2) 0.8555(3) 0.39491(19) 0.0662(10) Uani 1 1 d . . . H34A H 0.4971 0.9168 0.3925 0.079 Uiso 1 1 calc R . . C35 C 0.4051(2) 0.8380(2) 0.36904(17) 0.0575(9) Uani 1 1 d . . . H35A H 0.3755 0.8881 0.3494 0.069 Uiso 1 1 calc R . . C36 C 0.37497(18) 0.7469(2) 0.37171(15) 0.0483(8) Uani 1 1 d . . . C37 C 0.2952(2) 0.7313(2) 0.34171(18) 0.0574(9) Uani 1 1 d . . . H37A H 0.2843 0.6623 0.3445 0.069 Uiso 1 1 calc R . . C38 C 0.2729(3) 0.7600(3) 0.27653(19) 0.0745(11) Uani 1 1 d . . . H38A H 0.2224 0.7452 0.2591 0.112 Uiso 1 1 calc R . . H38B H 0.3016 0.7246 0.2562 0.112 Uiso 1 1 calc R . . H38C H 0.2805 0.8283 0.2731 0.112 Uiso 1 1 calc R . . O4 O 0.31075(14) 0.58647(18) 0.52531(12) 0.0626(7) Uani 1 1 d . . . H4 H 0.3088 0.6254 0.5512 0.094 Uiso 1 1 calc R . . C41 C 0.39286(16) 0.5710(2) 0.40504(15) 0.0458(7) Uani 1 1 d . . . C42 C 0.3904(2) 0.5074(2) 0.35903(17) 0.0590(9) Uani 1 1 d . . . H42A H 0.4036 0.5290 0.3261 0.071 Uiso 1 1 calc R . . C43 C 0.3685(2) 0.4126(3) 0.3612(2) 0.0696(11) Uani 1 1 d . . . H43A H 0.3660 0.3709 0.3296 0.083 Uiso 1 1 calc R . . C44 C 0.3506(2) 0.3804(2) 0.4105(2) 0.0639(10) Uani 1 1 d . . . H44A H 0.3377 0.3159 0.4131 0.077 Uiso 1 1 calc R . . C45 C 0.35147(19) 0.4429(2) 0.45583(19) 0.0584(9) Uani 1 1 d . . . H45A H 0.3379 0.4206 0.4885 0.070 Uiso 1 1 calc R . . C46 C 0.37244(16) 0.5399(2) 0.45407(15) 0.0482(8) Uani 1 1 d . . . C47 C 0.37255(17) 0.6080(2) 0.50453(16) 0.0513(8) Uani 1 1 d . . . H47A H 0.3680 0.6746 0.4895 0.062 Uiso 1 1 calc R . . C48 C 0.4408(2) 0.6009(4) 0.5565(2) 0.0856(13) Uani 1 1 d . . . H48A H 0.4351 0.6395 0.5889 0.128 Uiso 1 1 calc R . . H48B H 0.4816 0.6241 0.5446 0.128 Uiso 1 1 calc R . . H48C H 0.4489 0.5345 0.5690 0.128 Uiso 1 1 calc R . . O5 O 0.1927(2) 0.6463(2) 0.43903(19) 0.1183(16) Uani 1 1 d . . . H5 H 0.2186 0.6339 0.4725 0.177 Uiso 1 1 calc R . . C51 C 0.03692(18) 0.5316(2) 0.33814(16) 0.0518(8) Uani 1 1 d . . . C52 C 0.0234(2) 0.4629(3) 0.29245(19) 0.0683(10) Uani 1 1 d . . . H52A H -0.0222 0.4599 0.2650 0.082 Uiso 1 1 calc R . . C53 C 0.0772(3) 0.3994(3) 0.2876(2) 0.0869(14) Uani 1 1 d . . . H53A H 0.0674 0.3539 0.2571 0.104 Uiso 1 1 calc R . . C54 C 0.1443(3) 0.4032(4) 0.3274(2) 0.0868(14) Uani 1 1 d . . . H54A H 0.1804 0.3603 0.3243 0.104 Uiso 1 1 calc R . . C55 C 0.1584(2) 0.4701(3) 0.3716(2) 0.0785(12) Uani 1 1 d . . . H55A H 0.2045 0.4728 0.3984 0.094 Uiso 1 1 calc R . . C56 C 0.1054(2) 0.5346(2) 0.37766(18) 0.0605(9) Uani 1 1 d . . . C57 C 0.1226(2) 0.6025(3) 0.4305(2) 0.0793(13) Uani 1 1 d . . . H57A H 0.0860 0.6541 0.4225 0.095 Uiso 1 1 calc R . . C58 C 0.1194(3) 0.5496(4) 0.4862(3) 0.0997(16) Uani 1 1 d . . . H58A H 0.1286 0.5945 0.5187 0.150 Uiso 1 1 calc R . . H58B H 0.1555 0.4994 0.4952 0.150 Uiso 1 1 calc R . . H58C H 0.0722 0.5214 0.4800 0.150 Uiso 1 1 calc R . . O6 O 0.04401(18) 0.8361(2) 0.33542(15) 0.0796(8) Uani 1 1 d D . . H6 H 0.080(2) 0.863(4) 0.328(3) 0.119 Uiso 1 1 d D . . C61 C -0.02462(17) 0.5956(2) 0.34257(15) 0.0484(7) Uani 1 1 d . . . C62 C -0.0799(2) 0.5545(3) 0.36159(18) 0.0624(9) Uani 1 1 d . . . H62A H -0.0768 0.4891 0.3716 0.075 Uiso 1 1 calc R . . C63 C -0.1387(2) 0.6057(3) 0.3663(2) 0.0732(11) Uani 1 1 d . . . H63A H -0.1749 0.5759 0.3791 0.088 Uiso 1 1 calc R . . C64 C -0.1433(2) 0.7031(3) 0.35153(19) 0.0702(11) Uani 1 1 d . . . H64A H -0.1830 0.7390 0.3546 0.084 Uiso 1 1 calc R . . C65 C -0.08983(19) 0.7473(3) 0.33245(17) 0.0588(9) Uani 1 1 d . . . H65A H -0.0939 0.8127 0.3225 0.071 Uiso 1 1 calc R . . C66 C -0.02934(17) 0.6944(2) 0.32793(14) 0.0471(7) Uani 1 1 d . . . C67 C 0.02728(19) 0.7459(2) 0.30566(16) 0.0533(8) Uani 1 1 d . . . H67A H 0.0713 0.7060 0.3144 0.064 Uiso 1 1 calc R . . C68 C 0.0001(3) 0.7632(4) 0.2392(2) 0.0930(15) Uani 1 1 d . . . H68A H 0.0358 0.7992 0.2266 0.140 Uiso 1 1 calc R . . H68B H -0.0445 0.7992 0.2301 0.140 Uiso 1 1 calc R . . H68C H -0.0082 0.7020 0.2189 0.140 Uiso 1 1 calc R . . O7 O 0.29758(14) 0.84458(17) 0.50523(14) 0.0675(7) Uani 1 1 d D . . H7 H 0.2539(11) 0.864(4) 0.499(2) 0.101 Uiso 1 1 d D . . C71 C 0.28923(17) 1.0916(2) 0.46057(15) 0.0480(7) Uani 1 1 d . . . C72 C 0.2563(2) 1.1778(3) 0.4719(2) 0.0675(10) Uani 1 1 d . . . H72A H 0.2448 1.2261 0.4431 0.081 Uiso 1 1 calc R . . C73 C 0.2409(3) 1.1917(3) 0.5251(3) 0.0852(14) Uani 1 1 d . . . H73A H 0.2182 1.2482 0.5320 0.102 Uiso 1 1 calc R . . C74 C 0.2596(3) 1.1211(4) 0.5678(2) 0.0844(13) Uani 1 1 d . . . H74A H 0.2504 1.1306 0.6042 0.101 Uiso 1 1 calc R . . C75 C 0.2917(2) 1.0363(3) 0.55755(17) 0.0655(10) Uani 1 1 d . . . H75A H 0.3040 0.9892 0.5871 0.079 Uiso 1 1 calc R . . C76 C 0.30605(17) 1.0199(2) 0.50362(14) 0.0476(7) Uani 1 1 d . . . C77 C 0.3391(2) 0.9237(2) 0.49311(16) 0.0548(8) Uani 1 1 d . . . H77A H 0.3386 0.9204 0.4514 0.066 Uiso 1 1 calc R . . C78 C 0.4157(2) 0.9093(3) 0.5312(2) 0.0802(12) Uani 1 1 d . . . H78A H 0.4347 0.8502 0.5200 0.120 Uiso 1 1 calc R . . H78B H 0.4163 0.9056 0.5721 0.120 Uiso 1 1 calc R . . H78C H 0.4451 0.9629 0.5259 0.120 Uiso 1 1 calc R . . O8 O 0.16150(14) 0.93171(18) 0.31321(12) 0.0633(7) Uani 1 1 d D . . H8 H 0.189(2) 0.884(2) 0.328(2) 0.095 Uiso 1 1 d D . . C81 C 0.30781(17) 1.08294(19) 0.40237(15) 0.0452(7) Uani 1 1 d . . . C82 C 0.3767(2) 1.1134(2) 0.40084(18) 0.0570(9) Uani 1 1 d . . . H82A H 0.4097 1.1367 0.4352 0.068 Uiso 1 1 calc R . . C83 C 0.3958(2) 1.1092(3) 0.3490(2) 0.0646(10) Uani 1 1 d . . . H83A H 0.4417 1.1293 0.3484 0.078 Uiso 1 1 calc R . . C84 C 0.3468(2) 1.0750(3) 0.29770(19) 0.0656(10) Uani 1 1 d . . . H84A H 0.3598 1.0727 0.2625 0.079 Uiso 1 1 calc R . . C85 C 0.2785(2) 1.0442(2) 0.29861(16) 0.0557(8) Uani 1 1 d . . . H85A H 0.2460 1.0208 0.2640 0.067 Uiso 1 1 calc R . . C86 C 0.25787(17) 1.0479(2) 0.35084(15) 0.0458(7) Uani 1 1 d . . . C87 C 0.18345(18) 1.0138(2) 0.35128(16) 0.0522(8) Uani 1 1 d . . . H87A H 0.1853 0.9949 0.3919 0.063 Uiso 1 1 calc R . . C88 C 0.1256(2) 1.0908(3) 0.3305(2) 0.0747(11) Uani 1 1 d . . . H88A H 0.0796 1.0656 0.3321 0.112 Uiso 1 1 calc R . . H88B H 0.1225 1.1090 0.2904 0.112 Uiso 1 1 calc R . . H88C H 0.1379 1.1465 0.3558 0.112 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 O1 0.106(2) 0.092(2) 0.085(2) 0.0084(17) 0.0671(19) 0.0287(19) C11 0.0519(19) 0.0556(17) 0.0443(16) 0.0017(13) 0.0166(15) 0.0062(15) C12 0.073(3) 0.079(2) 0.060(2) 0.0034(19) 0.021(2) -0.004(2) C13 0.070(3) 0.078(2) 0.079(3) -0.001(2) 0.030(2) -0.022(2) C14 0.055(2) 0.075(2) 0.074(3) -0.006(2) 0.0072(19) -0.0120(18) C15 0.0453(19) 0.069(2) 0.0518(18) -0.0079(16) 0.0123(15) 0.0005(16) C16 0.0428(17) 0.0576(17) 0.0395(15) -0.0048(13) 0.0137(13) 0.0073(14) C17 0.0437(19) 0.082(2) 0.0413(17) -0.0066(15) 0.0148(15) 0.0026(16) C18 0.087(3) 0.064(2) 0.108(3) 0.005(2) 0.060(3) 0.008(2) O2 0.0611(17) 0.0750(16) 0.082(2) 0.0075(15) 0.0297(15) 0.0151(13) C21 0.052(2) 0.0584(18) 0.0401(16) 0.0002(13) 0.0104(14) 0.0029(15) C22 0.071(3) 0.076(2) 0.061(2) -0.0210(19) 0.0060(19) 0.015(2) C23 0.107(4) 0.066(2) 0.066(3) -0.0220(19) -0.005(2) 0.014(2) C24 0.085(3) 0.071(2) 0.053(2) -0.0061(18) -0.009(2) -0.002(2) C25 0.060(2) 0.077(2) 0.0469(19) 0.0051(17) -0.0021(17) 0.0025(18) C26 0.053(2) 0.0556(17) 0.0400(16) 0.0046(13) 0.0100(14) 0.0001(15) C27 0.055(2) 0.0564(18) 0.0568(19) 0.0026(15) 0.0143(16) 0.0031(15) C28 0.128(5) 0.067(3) 0.121(4) 0.017(3) 0.066(4) 0.017(3) O3 0.0612(17) 0.0886(18) 0.087(2) 0.0227(15) 0.0323(15) 0.0186(14) C31 0.0483(18) 0.0432(15) 0.0550(18) -0.0046(13) 0.0190(15) 0.0004(13) C32 0.0400(19) 0.066(2) 0.086(3) 0.0064(19) 0.0095(18) 0.0021(16) C33 0.048(2) 0.080(3) 0.082(3) -0.017(2) 0.0187(19) -0.0181(19) C34 0.067(3) 0.056(2) 0.081(3) -0.0081(18) 0.030(2) -0.0170(18) C35 0.061(2) 0.0455(16) 0.069(2) 0.0028(15) 0.0223(18) -0.0011(15) C36 0.050(2) 0.0437(16) 0.0546(18) 0.0024(13) 0.0208(15) 0.0010(13) C37 0.052(2) 0.0457(16) 0.073(2) 0.0134(15) 0.0168(17) 0.0036(14) C38 0.086(3) 0.063(2) 0.066(2) -0.0050(18) 0.008(2) 0.002(2) O4 0.0508(14) 0.0705(15) 0.0719(16) 0.0033(12) 0.0264(12) 0.0090(11) C41 0.0330(16) 0.0425(15) 0.0585(18) -0.0003(13) 0.0077(14) 0.0059(12) C42 0.059(2) 0.0515(18) 0.065(2) -0.0028(15) 0.0148(17) 0.0043(15) C43 0.052(2) 0.055(2) 0.100(3) -0.023(2) 0.020(2) 0.0032(16) C44 0.049(2) 0.0391(16) 0.104(3) -0.0029(18) 0.022(2) 0.0017(14) C45 0.0451(19) 0.0426(16) 0.087(3) 0.0088(16) 0.0187(17) 0.0059(14) C46 0.0330(16) 0.0404(15) 0.069(2) 0.0046(14) 0.0106(14) 0.0095(12) C47 0.0372(17) 0.0501(16) 0.068(2) 0.0018(15) 0.0164(15) 0.0084(13) C48 0.049(2) 0.116(4) 0.085(3) -0.020(3) 0.007(2) 0.011(2) O5 0.088(2) 0.087(2) 0.136(3) 0.039(2) -0.039(2) -0.0348(18) C51 0.0429(18) 0.0525(17) 0.063(2) 0.0005(15) 0.0194(15) -0.0023(14) C52 0.070(3) 0.068(2) 0.068(2) 0.0003(18) 0.0220(19) 0.0000(19) C53 0.119(4) 0.078(3) 0.078(3) -0.006(2) 0.051(3) 0.023(3) C54 0.093(4) 0.085(3) 0.095(3) 0.001(3) 0.047(3) 0.025(3) C55 0.064(3) 0.068(2) 0.103(3) 0.010(2) 0.024(2) 0.008(2) C56 0.050(2) 0.0512(17) 0.078(2) 0.0002(16) 0.0150(18) 0.0027(15) C57 0.063(3) 0.063(2) 0.089(3) -0.012(2) -0.016(2) 0.0078(18) C58 0.087(3) 0.111(4) 0.095(4) -0.036(3) 0.017(3) -0.012(3) O6 0.080(2) 0.0759(18) 0.089(2) -0.0105(15) 0.0357(17) -0.0236(15) C61 0.0350(16) 0.0565(17) 0.0530(18) -0.0067(14) 0.0116(14) -0.0049(13) C62 0.050(2) 0.066(2) 0.070(2) -0.0047(17) 0.0166(17) -0.0121(17) C63 0.047(2) 0.097(3) 0.081(3) -0.009(2) 0.0266(19) -0.015(2) C64 0.0387(19) 0.098(3) 0.076(3) -0.022(2) 0.0191(18) 0.0071(19) C65 0.0437(19) 0.072(2) 0.060(2) -0.0109(17) 0.0123(16) 0.0093(16) C66 0.0384(17) 0.0569(17) 0.0436(16) -0.0077(13) 0.0076(13) 0.0018(13) C67 0.0482(19) 0.0513(17) 0.061(2) 0.0002(15) 0.0168(16) -0.0008(14) C68 0.103(4) 0.127(4) 0.059(2) -0.008(2) 0.038(3) -0.026(3) O7 0.0525(15) 0.0492(13) 0.096(2) 0.0067(12) 0.0133(14) -0.0034(11) C71 0.0408(17) 0.0435(15) 0.062(2) -0.0057(14) 0.0192(15) -0.0036(12) C72 0.062(2) 0.0518(18) 0.097(3) -0.0039(19) 0.036(2) 0.0009(16) C73 0.090(3) 0.068(2) 0.111(4) -0.032(3) 0.048(3) -0.001(2) C74 0.099(4) 0.090(3) 0.078(3) -0.028(2) 0.049(3) -0.010(3) C75 0.078(3) 0.069(2) 0.055(2) -0.0062(17) 0.0263(19) -0.0078(19) C76 0.0466(18) 0.0482(16) 0.0506(18) -0.0079(13) 0.0179(14) -0.0083(13) C77 0.059(2) 0.0500(17) 0.059(2) 0.0037(14) 0.0225(17) -0.0042(15) C78 0.048(2) 0.076(2) 0.112(4) -0.006(2) 0.016(2) -0.0028(18) O8 0.0493(14) 0.0605(14) 0.0753(17) 0.0034(12) 0.0101(12) -0.0019(11) C81 0.0402(17) 0.0367(14) 0.0634(19) 0.0093(13) 0.0225(15) 0.0031(12) C82 0.047(2) 0.0554(18) 0.072(2) 0.0067(16) 0.0230(17) -0.0037(15) C83 0.047(2) 0.068(2) 0.089(3) 0.017(2) 0.036(2) -0.0002(16) C84 0.069(3) 0.067(2) 0.076(3) 0.0294(19) 0.044(2) 0.0103(19) C85 0.065(2) 0.0516(17) 0.0555(19) 0.0125(15) 0.0246(17) 0.0088(16) C86 0.0449(17) 0.0407(14) 0.0572(18) 0.0136(13) 0.0231(15) 0.0086(13) C87 0.0447(18) 0.0553(17) 0.0578(19) 0.0051(15) 0.0165(15) -0.0028(14) C88 0.049(2) 0.073(2) 0.102(3) 0.019(2) 0.023(2) 0.0087(18) _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 C17 1.415(4) . ? O1 H1 0.847(10) . ? C11 C12 1.392(5) . ? C11 C16 1.418(4) . ? C11 C21 1.497(5) . ? C12 C13 1.377(6) . ? C12 H12A 0.9300 . ? C13 C14 1.383(6) . ? C13 H13A 0.9300 . ? C14 C15 1.372(6) . ? C14 H14A 0.9300 . ? C15 C16 1.385(5) . ? C15 H15A 0.9300 . ? C16 C17 1.502(5) . ? C17 C18 1.512(6) . ? C17 H17A 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O2 C27 1.442(5) . ? O2 H2 0.851(10) . ? C21 C22 1.377(5) . ? C21 C26 1.392(5) . ? C22 C23 1.387(6) . ? C22 H22A 0.9300 . ? C23 C24 1.352(7) . ? C23 H23A 0.9300 . ? C24 C25 1.391(6) . ? C24 H24A 0.9300 . ? C25 C26 1.386(5) . ? C25 H25A 0.9300 . ? C26 C27 1.507(5) . ? C27 C28 1.517(6) . ? C27 H27A 0.9800 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? O3 C37 1.430(5) . ? O3 H3 0.8200 . ? C31 C36 1.390(5) . ? C31 C32 1.394(5) . ? C31 C41 1.515(4) . ? C32 C33 1.387(6) . ? C32 H32A 0.9300 . ? C33 C34 1.356(6) . ? C33 H33A 0.9300 . ? C34 C35 1.381(6) . ? C34 H34A 0.9300 . ? C35 C36 1.392(5) . ? C35 H35A 0.9300 . ? C36 C37 1.509(5) . ? C37 C38 1.521(6) . ? C37 H37A 0.9800 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? O4 C47 1.438(4) . ? O4 H4 0.8200 . ? C41 C42 1.382(5) . ? C41 C46 1.387(5) . ? C42 C43 1.379(5) . ? C42 H42A 0.9300 . ? C43 C44 1.375(6) . ? C43 H43A 0.9300 . ? C44 C45 1.366(6) . ? C44 H44A 0.9300 . ? C45 C46 1.402(5) . ? C45 H45A 0.9300 . ? C46 C47 1.512(5) . ? C47 C48 1.520(6) . ? C47 H47A 0.9800 . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? O5 C57 1.438(6) . ? O5 H5 0.8200 . ? C51 C56 1.378(5) . ? C51 C52 1.400(5) . ? C51 C61 1.503(5) . ? C52 C53 1.383(6) . ? C52 H52A 0.9300 . ? C53 C54 1.361(8) . ? C53 H53A 0.9300 . ? C54 C55 1.358(7) . ? C54 H54A 0.9300 . ? C55 C56 1.388(6) . ? C55 H55A 0.9300 . ? C56 C57 1.516(6) . ? C57 C58 1.514(8) . ? C57 H57A 0.9800 . ? C58 H58A 0.9600 . ? C58 H58B 0.9600 . ? C58 H58C 0.9600 . ? O6 C67 1.419(4) . ? O6 H6 0.851(10) . ? C61 C62 1.386(5) . ? C61 C66 1.403(5) . ? C62 C63 1.362(6) . ? C62 H62A 0.9300 . ? C63 C64 1.383(6) . ? C63 H63A 0.9300 . ? C64 C65 1.375(6) . ? C64 H64A 0.9300 . ? C65 C66 1.402(5) . ? C65 H65A 0.9300 . ? C66 C67 1.512(5) . ? C67 C68 1.518(6) . ? C67 H67A 0.9800 . ? C68 H68A 0.9600 . ? C68 H68B 0.9600 . ? C68 H68C 0.9600 . ? O7 C77 1.428(4) . ? O7 H7 0.852(10) . ? C71 C76 1.386(5) . ? C71 C72 1.408(5) . ? C71 C81 1.514(5) . ? C72 C73 1.377(7) . ? C72 H72A 0.9300 . ? C73 C74 1.371(7) . ? C73 H73A 0.9300 . ? C74 C75 1.376(6) . ? C74 H74A 0.9300 . ? C75 C76 1.390(5) . ? C75 H75A 0.9300 . ? C76 C77 1.521(5) . ? C77 C78 1.502(6) . ? C77 H77A 0.9800 . ? C78 H78A 0.9600 . ? C78 H78B 0.9600 . ? C78 H78C 0.9600 . ? O8 C87 1.431(4) . ? O8 H8 0.853(10) . ? C81 C82 1.399(5) . ? C81 C86 1.399(5) . ? C82 C83 1.370(6) . ? C82 H82A 0.9300 . ? C83 C84 1.384(6) . ? C83 H83A 0.9300 . ? C84 C85 1.387(5) . ? C84 H84A 0.9300 . ? C85 C86 1.394(5) . ? C85 H85A 0.9300 . ? C86 C87 1.508(5) . ? C87 C88 1.513(5) . ? C87 H87A 0.9800 . ? C88 H88A 0.9600 . ? C88 H88B 0.9600 . ? C88 H88C 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 C17 O1 H1 105(5) . . ? C12 C11 C16 118.7(3) . . ? C12 C11 C21 119.1(3) . . ? C16 C11 C21 122.2(3) . . ? C13 C12 C11 122.1(4) . . ? C13 C12 H12A 118.9 . . ? C11 C12 H12A 118.9 . . ? C12 C13 C14 118.6(4) . . ? C12 C13 H13A 120.7 . . ? C14 C13 H13A 120.7 . . ? C15 C14 C13 120.5(4) . . ? C15 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C14 C15 C16 121.8(3) . . ? C14 C15 H15A 119.1 . . ? C16 C15 H15A 119.1 . . ? C15 C16 C11 118.2(3) . . ? C15 C16 C17 121.3(3) . . ? C11 C16 C17 120.5(3) . . ? O1 C17 C16 112.2(3) . . ? O1 C17 C18 108.6(3) . . ? C16 C17 C18 112.9(3) . . ? O1 C17 H17A 107.6 . . ? C16 C17 H17A 107.6 . . ? C18 C17 H17A 107.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C27 O2 H2 94(5) . . ? C22 C21 C26 118.9(3) . . ? C22 C21 C11 118.8(3) . . ? C26 C21 C11 122.3(3) . . ? C21 C22 C23 121.9(4) . . ? C21 C22 H22A 119.1 . . ? C23 C22 H22A 119.1 . . ? C24 C23 C22 119.0(4) . . ? C24 C23 H23A 120.5 . . ? C22 C23 H23A 120.5 . . ? C23 C24 C25 120.6(4) . . ? C23 C24 H24A 119.7 . . ? C25 C24 H24A 119.7 . . ? C26 C25 C24 120.5(4) . . ? C26 C25 H25A 119.8 . . ? C24 C25 H25A 119.8 . . ? C25 C26 C21 119.2(3) . . ? C25 C26 C27 119.8(3) . . ? C21 C26 C27 121.0(3) . . ? O2 C27 C26 112.0(3) . . ? O2 C27 C28 106.1(3) . . ? C26 C27 C28 111.6(3) . . ? O2 C27 H27A 109.0 . . ? C26 C27 H27A 109.0 . . ? C28 C27 H27A 109.0 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C37 O3 H3 109.5 . . ? C36 C31 C32 119.7(3) . . ? C36 C31 C41 122.2(3) . . ? C32 C31 C41 118.2(3) . . ? C33 C32 C31 120.6(4) . . ? C33 C32 H32A 119.7 . . ? C31 C32 H32A 119.7 . . ? C34 C33 C32 119.9(4) . . ? C34 C33 H33A 120.1 . . ? C32 C33 H33A 120.1 . . ? C33 C34 C35 120.2(3) . . ? C33 C34 H34A 119.9 . . ? C35 C34 H34A 119.9 . . ? C34 C35 C36 121.4(3) . . ? C34 C35 H35A 119.3 . . ? C36 C35 H35A 119.3 . . ? C31 C36 C35 118.3(3) . . ? C31 C36 C37 122.4(3) . . ? C35 C36 C37 119.2(3) . . ? O3 C37 C36 110.4(3) . . ? O3 C37 C38 108.2(3) . . ? C36 C37 C38 113.0(3) . . ? O3 C37 H37A 108.4 . . ? C36 C37 H37A 108.4 . . ? C38 C37 H37A 108.4 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C47 O4 H4 109.5 . . ? C42 C41 C46 120.0(3) . . ? C42 C41 C31 118.1(3) . . ? C46 C41 C31 121.9(3) . . ? C43 C42 C41 121.1(4) . . ? C43 C42 H42A 119.5 . . ? C41 C42 H42A 119.5 . . ? C44 C43 C42 119.3(4) . . ? C44 C43 H43A 120.3 . . ? C42 C43 H43A 120.3 . . ? C45 C44 C43 120.2(3) . . ? C45 C44 H44A 119.9 . . ? C43 C44 H44A 119.9 . . ? C44 C45 C46 121.3(4) . . ? C44 C45 H45A 119.4 . . ? C46 C45 H45A 119.4 . . ? C41 C46 C45 118.1(3) . . ? C41 C46 C47 121.5(3) . . ? C45 C46 C47 120.4(3) . . ? O4 C47 C46 108.8(3) . . ? O4 C47 C48 108.7(3) . . ? C46 C47 C48 113.5(3) . . ? O4 C47 H47A 108.6 . . ? C46 C47 H47A 108.6 . . ? C48 C47 H47A 108.6 . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C57 O5 H5 109.5 . . ? C56 C51 C52 118.0(3) . . ? C56 C51 C61 123.7(3) . . ? C52 C51 C61 118.3(3) . . ? C53 C52 C51 120.9(4) . . ? C53 C52 H52A 119.6 . . ? C51 C52 H52A 119.6 . . ? C54 C53 C52 120.1(4) . . ? C54 C53 H53A 119.9 . . ? C52 C53 H53A 119.9 . . ? C55 C54 C53 119.6(4) . . ? C55 C54 H54A 120.2 . . ? C53 C54 H54A 120.2 . . ? C54 C55 C56 121.5(4) . . ? C54 C55 H55A 119.3 . . ? C56 C55 H55A 119.3 . . ? C51 C56 C55 119.9(4) . . ? C51 C56 C57 120.9(3) . . ? C55 C56 C57 119.1(4) . . ? O5 C57 C58 110.5(4) . . ? O5 C57 C56 110.4(4) . . ? C58 C57 C56 110.9(4) . . ? O5 C57 H57A 108.3 . . ? C58 C57 H57A 108.3 . . ? C56 C57 H57A 108.3 . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C67 O6 H6 112(4) . . ? C62 C61 C66 118.3(3) . . ? C62 C61 C51 118.3(3) . . ? C66 C61 C51 123.4(3) . . ? C63 C62 C61 122.9(4) . . ? C63 C62 H62A 118.5 . . ? C61 C62 H62A 118.5 . . ? C62 C63 C64 118.5(4) . . ? C62 C63 H63A 120.7 . . ? C64 C63 H63A 120.7 . . ? C65 C64 C63 120.8(4) . . ? C65 C64 H64A 119.6 . . ? C63 C64 H64A 119.6 . . ? C64 C65 C66 120.5(4) . . ? C64 C65 H65A 119.8 . . ? C66 C65 H65A 119.8 . . ? C65 C66 C61 118.9(3) . . ? C65 C66 C67 118.4(3) . . ? C61 C66 C67 122.6(3) . . ? O6 C67 C66 109.0(3) . . ? O6 C67 C68 109.4(3) . . ? C66 C67 C68 111.1(3) . . ? O6 C67 H67A 109.1 . . ? C66 C67 H67A 109.1 . . ? C68 C67 H67A 109.1 . . ? C67 C68 H68A 109.5 . . ? C67 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? C67 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 109.5 . . ? C77 O7 H7 108(4) . . ? C76 C71 C72 119.2(3) . . ? C76 C71 C81 122.5(3) . . ? C72 C71 C81 118.2(3) . . ? C73 C72 C71 120.9(4) . . ? C73 C72 H72A 119.5 . . ? C71 C72 H72A 119.5 . . ? C74 C73 C72 119.1(4) . . ? C74 C73 H73A 120.4 . . ? C72 C73 H73A 120.4 . . ? C73 C74 C75 120.8(4) . . ? C73 C74 H74A 119.6 . . ? C75 C74 H74A 119.6 . . ? C74 C75 C76 120.9(4) . . ? C74 C75 H75A 119.5 . . ? C76 C75 H75A 119.5 . . ? C71 C76 C75 118.9(3) . . ? C71 C76 C77 121.7(3) . . ? C75 C76 C77 119.4(3) . . ? O7 C77 C78 106.7(3) . . ? O7 C77 C76 110.6(3) . . ? C78 C77 C76 113.7(3) . . ? O7 C77 H77A 108.6 . . ? C78 C77 H77A 108.6 . . ? C76 C77 H77A 108.6 . . ? C77 C78 H78A 109.5 . . ? C77 C78 H78B 109.5 . . ? H78A C78 H78B 109.5 . . ? C77 C78 H78C 109.5 . . ? H78A C78 H78C 109.5 . . ? H78B C78 H78C 109.5 . . ? C87 O8 H8 108(4) . . ? C82 C81 C86 120.1(3) . . ? C82 C81 C71 117.9(3) . . ? C86 C81 C71 122.0(3) . . ? C83 C82 C81 120.4(4) . . ? C83 C82 H82A 119.8 . . ? C81 C82 H82A 119.8 . . ? C82 C83 C84 120.1(3) . . ? C82 C83 H83A 119.9 . . ? C84 C83 H83A 119.9 . . ? C83 C84 C85 120.1(4) . . ? C83 C84 H84A 119.9 . . ? C85 C84 H84A 119.9 . . ? C84 C85 C86 120.7(4) . . ? C84 C85 H85A 119.6 . . ? C86 C85 H85A 119.6 . . ? C85 C86 C81 118.6(3) . . ? C85 C86 C87 120.2(3) . . ? C81 C86 C87 121.2(3) . . ? O8 C87 C86 110.7(3) . . ? O8 C87 C88 107.2(3) . . ? C86 C87 C88 113.0(3) . . ? O8 C87 H87A 108.6 . . ? C86 C87 H87A 108.6 . . ? C88 C87 H87A 108.6 . . ? C87 C88 H88A 109.5 . . ? C87 C88 H88B 109.5 . . ? H88A C88 H88B 109.5 . . ? C87 C88 H88C 109.5 . . ? H88A C88 H88C 109.5 . . ? H88B C88 H88C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 C12 C13 -0.6(6) . . . . ? C21 C11 C12 C13 178.9(4) . . . . ? C11 C12 C13 C14 1.9(7) . . . . ? C12 C13 C14 C15 -3.3(7) . . . . ? C13 C14 C15 C16 3.5(6) . . . . ? C14 C15 C16 C11 -2.1(5) . . . . ? C14 C15 C16 C17 -179.6(3) . . . . ? C12 C11 C16 C15 0.7(5) . . . . ? C21 C11 C16 C15 -178.8(3) . . . . ? C12 C11 C16 C17 178.2(3) . . . . ? C21 C11 C16 C17 -1.4(5) . . . . ? C15 C16 C17 O1 -51.4(4) . . . . ? C11 C16 C17 O1 131.2(3) . . . . ? C15 C16 C17 C18 71.7(4) . . . . ? C11 C16 C17 C18 -105.7(4) . . . . ? C12 C11 C21 C22 -81.9(5) . . . . ? C16 C11 C21 C22 97.6(4) . . . . ? C12 C11 C21 C26 96.7(4) . . . . ? C16 C11 C21 C26 -83.7(4) . . . . ? C26 C21 C22 C23 0.0(6) . . . . ? C11 C21 C22 C23 178.7(4) . . . . ? C21 C22 C23 C24 -1.3(7) . . . . ? C22 C23 C24 C25 1.0(7) . . . . ? C23 C24 C25 C26 0.6(7) . . . . ? C24 C25 C26 C21 -1.9(6) . . . . ? C24 C25 C26 C27 -179.4(4) . . . . ? C22 C21 C26 C25 1.6(5) . . . . ? C11 C21 C26 C25 -177.1(3) . . . . ? C22 C21 C26 C27 179.1(3) . . . . ? C11 C21 C26 C27 0.4(5) . . . . ? C25 C26 C27 O2 -40.6(4) . . . . ? C21 C26 C27 O2 141.9(3) . . . . ? C25 C26 C27 C28 78.3(5) . . . . ? C21 C26 C27 C28 -99.2(4) . . . . ? C36 C31 C32 C33 -2.1(6) . . . . ? C41 C31 C32 C33 178.3(4) . . . . ? C31 C32 C33 C34 1.5(6) . . . . ? C32 C33 C34 C35 -0.4(6) . . . . ? C33 C34 C35 C36 -0.1(6) . . . . ? C32 C31 C36 C35 1.6(5) . . . . ? C41 C31 C36 C35 -178.9(3) . . . . ? C32 C31 C36 C37 179.8(3) . . . . ? C41 C31 C36 C37 -0.6(5) . . . . ? C34 C35 C36 C31 -0.5(5) . . . . ? C34 C35 C36 C37 -178.8(4) . . . . ? C31 C36 C37 O3 114.6(3) . . . . ? C35 C36 C37 O3 -67.1(4) . . . . ? C31 C36 C37 C38 -124.0(4) . . . . ? C35 C36 C37 C38 54.2(4) . . . . ? C36 C31 C41 C42 86.4(4) . . . . ? C32 C31 C41 C42 -94.0(4) . . . . ? C36 C31 C41 C46 -95.4(4) . . . . ? C32 C31 C41 C46 84.1(4) . . . . ? C46 C41 C42 C43 -0.7(5) . . . . ? C31 C41 C42 C43 177.5(3) . . . . ? C41 C42 C43 C44 -1.5(6) . . . . ? C42 C43 C44 C45 2.7(6) . . . . ? C43 C44 C45 C46 -1.8(5) . . . . ? C42 C41 C46 C45 1.7(4) . . . . ? C31 C41 C46 C45 -176.5(3) . . . . ? C42 C41 C46 C47 -178.4(3) . . . . ? C31 C41 C46 C47 3.5(4) . . . . ? C44 C45 C46 C41 -0.4(5) . . . . ? C44 C45 C46 C47 179.6(3) . . . . ? C41 C46 C47 O4 141.8(3) . . . . ? C45 C46 C47 O4 -38.2(4) . . . . ? C41 C46 C47 C48 -97.0(4) . . . . ? C45 C46 C47 C48 82.9(4) . . . . ? C56 C51 C52 C53 0.7(6) . . . . ? C61 C51 C52 C53 -177.3(4) . . . . ? C51 C52 C53 C54 -0.3(7) . . . . ? C52 C53 C54 C55 -0.4(8) . . . . ? C53 C54 C55 C56 0.6(7) . . . . ? C52 C51 C56 C55 -0.4(5) . . . . ? C61 C51 C56 C55 177.4(4) . . . . ? C52 C51 C56 C57 -176.0(4) . . . . ? C61 C51 C56 C57 1.9(6) . . . . ? C54 C55 C56 C51 -0.2(7) . . . . ? C54 C55 C56 C57 175.4(4) . . . . ? C51 C56 C57 O5 -138.7(4) . . . . ? C55 C56 C57 O5 45.7(5) . . . . ? C51 C56 C57 C58 98.5(5) . . . . ? C55 C56 C57 C58 -77.0(5) . . . . ? C56 C51 C61 C62 -106.2(4) . . . . ? C52 C51 C61 C62 71.6(4) . . . . ? C56 C51 C61 C66 74.4(5) . . . . ? C52 C51 C61 C66 -107.7(4) . . . . ? C66 C61 C62 C63 0.4(6) . . . . ? C51 C61 C62 C63 -179.0(4) . . . . ? C61 C62 C63 C64 -0.1(6) . . . . ? C62 C63 C64 C65 0.1(6) . . . . ? C63 C64 C65 C66 -0.4(6) . . . . ? C64 C65 C66 C61 0.7(5) . . . . ? C64 C65 C66 C67 178.9(3) . . . . ? C62 C61 C66 C65 -0.7(5) . . . . ? C51 C61 C66 C65 178.7(3) . . . . ? C62 C61 C66 C67 -178.8(3) . . . . ? C51 C61 C66 C67 0.5(5) . . . . ? C65 C66 C67 O6 46.5(4) . . . . ? C61 C66 C67 O6 -135.3(3) . . . . ? C65 C66 C67 C68 -74.1(4) . . . . ? C61 C66 C67 C68 104.0(4) . . . . ? C76 C71 C72 C73 0.2(6) . . . . ? C81 C71 C72 C73 -177.2(4) . . . . ? C71 C72 C73 C74 1.4(7) . . . . ? C72 C73 C74 C75 -1.5(7) . . . . ? C73 C74 C75 C76 -0.1(7) . . . . ? C72 C71 C76 C75 -1.8(5) . . . . ? C81 C71 C76 C75 175.5(3) . . . . ? C72 C71 C76 C77 177.7(3) . . . . ? C81 C71 C76 C77 -5.0(5) . . . . ? C74 C75 C76 C71 1.7(6) . . . . ? C74 C75 C76 C77 -177.8(4) . . . . ? C71 C76 C77 O7 -127.0(3) . . . . ? C75 C76 C77 O7 52.4(4) . . . . ? C71 C76 C77 C78 112.9(4) . . . . ? C75 C76 C77 C78 -67.6(4) . . . . ? C76 C71 C81 C82 -86.7(4) . . . . ? C72 C71 C81 C82 90.7(4) . . . . ? C76 C71 C81 C86 94.8(4) . . . . ? C72 C71 C81 C86 -87.8(4) . . . . ? C86 C81 C82 C83 -0.1(5) . . . . ? C71 C81 C82 C83 -178.6(3) . . . . ? C81 C82 C83 C84 0.3(5) . . . . ? C82 C83 C84 C85 -0.5(5) . . . . ? C83 C84 C85 C86 0.5(5) . . . . ? C84 C85 C86 C81 -0.3(4) . . . . ? C84 C85 C86 C87 -179.8(3) . . . . ? C82 C81 C86 C85 0.1(4) . . . . ? C71 C81 C86 C85 178.5(3) . . . . ? C82 C81 C86 C87 179.6(3) . . . . ? C71 C81 C86 C87 -2.0(4) . . . . ? C85 C86 C87 O8 36.5(4) . . . . ? C81 C86 C87 O8 -143.0(3) . . . . ? C85 C86 C87 C88 -83.7(4) . . . . ? C81 C86 C87 C88 96.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.421 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.064