# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Michael Sherburn' _publ_contact_author_address ; Research School of Chemistry Australian National University Science Road Canberra ACT 2601 AUSTRALIA ; _publ_contact_author_email SHERBURN@RSC.ANU.EDU.AU _publ_section_title ; Formal Total Synthesis of Triptolide ; loop_ _publ_author_name 'Michael Sherburn' 'Natalie A. Miller' 'Anthony A. Willis' #------------------------------------------------------------------------------ #===END data_she0610 _database_code_depnum_ccdc_archive 'CCDC 658574' _audit_creation_date 06-05-16 _audit_creation_method CRYSTALS_ver_12.18 _audit_update_record ; 2006-05-17 - Report on C21 H28 O4 by Anthony C. Willis for Natalie Miller and Mick Sherburn 2006-05-17 - passes checkcif tests with minor warnings 2007-08-27 # Formatted by publCIF ; _oxford_structure_analysis_title '5161634 she0610' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 17.8410(3) _cell_length_b 6.4751(1) _cell_length_c 17.9281(3) _cell_angle_alpha 90 _cell_angle_beta 118.2156(8) _cell_angle_gamma 90 _cell_volume 1825.00(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1 ' _symmetry_space_group_name_Hall ? 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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C21 H28 O4 # Dc = 1.25 Fooo = 744.00 Mu = 0.85 M = 344.45 # Found Formula = C21 H28 O4 # Dc = 1.25 FOOO = 744.00 Mu = 0.85 M = 344.45 _chemical_formula_sum 'C21 H28 O4' _chemical_formula_moiety 'C21 H28 O4' _chemical_compound_source local _chemical_formula_weight 344.45 _cell_measurement_reflns_used 21426 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 200 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.085 # Sheldrick geometric approximatio 0.97 0.99 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.220 0 -1 0 0.280 0 0 1 0.030 0 0 -1 0.060 -1 -1 0 0.254 -1 1 0 0.193 2 0 -1 0.114 1 0 3 0.019 -2 0 1 0.211 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.968 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.040 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 2.0 deg at rate 240 sec/frame, crystal-detector distance 28mm, multiple scan sets so over 95 percent of data collected with 4-fold redundancy or more. ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_cell_refinement 'Denzo/Scalepack ' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Watkin et al 2003)' _computing_publication_material 'CRYSTALS ' _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 36062 _reflns_number_total 4190 _diffrn_reflns_av_R_equivalents 0.043 # Number of reflections with Friedels Law is 4190 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4209 _diffrn_reflns_theta_min 2.579 _diffrn_reflns_theta_max 27.5 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.989 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -23 _reflns_limit_h_max 20 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _oxford_diffrn_Wilson_B_factor 2.67 _oxford_diffrn_Wilson_scale 0.96 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.14 _refine_diff_density_max 0.22 _refine_ls_number_reflns 2939 _refine_ls_number_restraints 0 _refine_ls_number_parameters 310 #_refine_ls_R_factor_ref 0.0320 _refine_ls_wR_factor_ref 0.0379 _refine_ls_goodness_of_fit_ref 1.0680 #_reflns_number_all 4181 _refine_ls_R_factor_all 0.0464 _refine_ls_wR_factor_all 0.0459 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 2939 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_gt 0.0379 _refine_ls_shift/su_max 0.004733 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refxyz # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.896 0.362 0.545 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.29032(5) 0.61760(14) 0.46009(5) 0.0439 1.0000 Uani . . . . . . O18 O 0.19778(5) 0.65214(15) 0.50932(6) 0.0472 1.0000 Uani . . . . . . O20 O 0.56428(5) 0.90598(13) 0.81658(5) 0.0397 1.0000 Uani . . . . . . O21 O 0.83929(5) 0.62721(13) 0.80512(5) 0.0374 1.0000 Uani . . . . . . C2 C 0.27067(7) 0.65762(17) 0.52255(7) 0.0368 1.0000 Uani . . . . . . C3 C 0.35027(7) 0.70040(17) 0.60493(7) 0.0324 1.0000 Uani . . . . . . C4 C 0.37000(7) 0.51536(19) 0.66510(7) 0.0348 1.0000 Uani . . . . . . C5 C 0.45978(7) 0.5355(2) 0.73869(7) 0.0333 1.0000 Uani . . . . . . C6 C 0.52857(6) 0.53547(16) 0.70926(6) 0.0277 1.0000 Uani . . . . . . C7 C 0.61720(6) 0.59054(16) 0.78307(6) 0.0273 1.0000 Uani . . . . . . C8 C 0.62439(7) 0.79857(17) 0.82637(6) 0.0296 1.0000 Uani . . . . . . C9 C 0.71163(7) 0.87112(18) 0.88347(7) 0.0334 1.0000 Uani . . . . . . C10 C 0.78186(7) 0.79276(17) 0.88548(7) 0.0309 1.0000 Uani . . . . . . C11 C 0.77415(7) 0.61055(17) 0.82935(7) 0.0313 1.0000 Uani . . . . . . C12 C 0.68540(7) 0.59036(17) 0.75333(7) 0.0297 1.0000 Uani . . . . . . C13 C 0.66482(7) 0.7585(2) 0.68627(7) 0.0341 1.0000 Uani . . . . . . C14 C 0.57095(7) 0.78584(17) 0.63002(7) 0.0316 1.0000 Uani . . . . . . C15 C 0.50897(7) 0.69126(16) 0.63850(6) 0.0277 1.0000 Uani . . . . . . C16 C 0.41731(7) 0.73827(18) 0.57609(7) 0.0324 1.0000 Uani . . . . . . C17 C 0.38211(8) 0.6102(2) 0.49468(8) 0.0445 1.0000 Uani . . . . . . C19 C 0.53145(8) 0.31384(17) 0.67820(8) 0.0359 1.0000 Uani . . . . . . C22 C 0.87066(7) 0.87037(19) 0.94460(7) 0.0363 1.0000 Uani . . . . . . C23 C 0.87223(9) 1.0662(2) 0.99197(9) 0.0482 1.0000 Uani . . . . . . C24 C 0.92230(10) 0.7000(3) 1.00706(11) 0.0558 1.0000 Uani . . . . . . C25 C 0.85635(9) 0.4380(2) 0.77553(9) 0.0439 1.0000 Uani . . . . . . H31 H 0.3396(8) 0.823(2) 0.6305(8) 0.0363 1.0000 Uiso . . . . . . H41 H 0.3285(9) 0.513(2) 0.6870(9) 0.0406 1.0000 Uiso . . . . . . H42 H 0.3626(9) 0.383(2) 0.6334(9) 0.0406 1.0000 Uiso . . . . . . H51 H 0.4623(9) 0.661(2) 0.7689(9) 0.0397 1.0000 Uiso . . . . . . H52 H 0.4728(9) 0.416(2) 0.7783(9) 0.0397 1.0000 Uiso . . . . . . H71 H 0.6341(8) 0.485(2) 0.8285(8) 0.0323 1.0000 Uiso . . . . . . H91 H 0.7141(8) 0.984(2) 0.9189(9) 0.0395 1.0000 Uiso . . . . . . H111 H 0.7847(8) 0.482(2) 0.8648(8) 0.0378 1.0000 Uiso . . . . . . H121 H 0.6835(8) 0.456(2) 0.7270(8) 0.0358 1.0000 Uiso . . . . . . H131 H 0.6891(9) 0.896(2) 0.7149(9) 0.0416 1.0000 Uiso . . . . . . H132 H 0.6917(9) 0.726(2) 0.6510(9) 0.0416 1.0000 Uiso . . . . . . H141 H 0.5541(8) 0.884(2) 0.5834(9) 0.0372 1.0000 Uiso . . . . . . H161 H 0.4143(8) 0.882(2) 0.5592(8) 0.0364 1.0000 Uiso . . . . . . H171 H 0.3998(9) 0.459(3) 0.5058(9) 0.0509 1.0000 Uiso . . . . . . H172 H 0.3948(10) 0.670(2) 0.4533(10) 0.0509 1.0000 Uiso . . . . . . H191 H 0.5717(9) 0.305(2) 0.6533(9) 0.0421 1.0000 Uiso . . . . . . H192 H 0.5501(9) 0.219(2) 0.7248(9) 0.0421 1.0000 Uiso . . . . . . H193 H 0.4739(9) 0.271(2) 0.6338(9) 0.0421 1.0000 Uiso . . . . . . H221 H 0.8967(9) 0.901(2) 0.9086(9) 0.0428 1.0000 Uiso . . . . . . H231 H 0.9324(11) 1.111(2) 1.0287(11) 0.0552 1.0000 Uiso . . . . . . H232 H 0.8469(10) 1.038(3) 1.0316(10) 0.0552 1.0000 Uiso . . . . . . H233 H 0.8398(10) 1.185(3) 0.9515(10) 0.0552 1.0000 Uiso . . . . . . H241 H 0.9827(11) 0.748(3) 1.0450(10) 0.0585 1.0000 Uiso . . . . . . H242 H 0.8954(11) 0.668(3) 1.0429(11) 0.0585 1.0000 Uiso . . . . . . H243 H 0.9254(10) 0.581(3) 0.9765(11) 0.0585 1.0000 Uiso . . . . . . H251 H 0.9094(10) 0.454(3) 0.7710(10) 0.0546 1.0000 Uiso . . . . . . H252 H 0.8636(10) 0.327(3) 0.8164(10) 0.0546 1.0000 Uiso . . . . . . H253 H 0.8076(11) 0.398(2) 0.7181(11) 0.0546 1.0000 Uiso . . . . . . 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 0.0368(4) 0.0506(5) 0.0308(4) -0.0033(4) 0.0050(3) -0.0009(4) O18 0.0295(4) 0.0458(5) 0.0519(5) -0.0044(4) 0.0075(4) -0.0014(4) O20 0.0327(4) 0.0397(4) 0.0449(5) -0.0044(4) 0.0168(3) 0.0063(3) O21 0.0310(4) 0.0406(5) 0.0452(4) -0.0027(4) 0.0218(4) 0.0029(3) C2 0.0341(6) 0.0279(5) 0.0366(6) -0.0002(4) 0.0070(5) 0.0015(4) C3 0.0276(5) 0.0315(5) 0.0317(5) -0.0028(4) 0.0087(4) 0.0010(4) C4 0.0292(5) 0.0400(6) 0.0326(5) 0.0007(5) 0.0125(4) -0.0031(5) C5 0.0297(5) 0.0411(6) 0.0285(5) 0.0028(5) 0.0132(4) -0.0017(4) C6 0.0279(5) 0.0275(5) 0.0258(5) 0.0019(4) 0.0112(4) 0.0003(4) C7 0.0271(5) 0.0288(5) 0.0251(5) 0.0029(4) 0.0116(4) 0.0024(4) C8 0.0297(5) 0.0330(5) 0.0269(5) 0.0018(4) 0.0142(4) 0.0028(4) C9 0.0326(5) 0.0361(6) 0.0303(5) -0.0051(4) 0.0138(4) -0.0002(4) C10 0.0307(5) 0.0335(6) 0.0273(5) 0.0021(4) 0.0126(4) 0.0002(4) C11 0.0275(5) 0.0335(5) 0.0336(5) 0.0018(4) 0.0151(4) 0.0030(4) C12 0.0276(5) 0.0321(5) 0.0301(5) -0.0017(4) 0.0143(4) 0.0016(4) C13 0.0324(5) 0.0423(6) 0.0294(5) 0.0021(5) 0.0162(4) -0.0022(5) C14 0.0349(5) 0.0322(5) 0.0261(5) 0.0022(4) 0.0133(4) -0.0003(4) C15 0.0300(5) 0.0267(5) 0.0240(5) -0.0005(4) 0.0108(4) 0.0010(4) C16 0.0320(5) 0.0300(5) 0.0291(5) 0.0034(4) 0.0094(4) 0.0001(4) C17 0.0366(6) 0.0634(9) 0.0274(5) -0.0032(5) 0.0103(5) -0.0025(6) C19 0.0389(6) 0.0272(5) 0.0393(6) 0.0007(5) 0.0166(5) 0.0000(5) C22 0.0302(5) 0.0445(6) 0.0324(5) 0.0001(5) 0.0133(4) -0.0038(5) C23 0.0434(7) 0.0518(8) 0.0428(7) -0.0111(6) 0.0150(6) -0.0111(6) C24 0.0360(7) 0.0577(9) 0.0526(8) 0.0095(7) 0.0038(6) 0.0009(6) C25 0.0405(7) 0.0453(7) 0.0508(7) -0.0007(6) 0.0256(6) 0.0104(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.0927(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.3476(16) yes O1 . C17 . 1.4520(15) yes O18 . C2 . 1.2069(15) yes O20 . C8 . 1.2194(13) yes O21 . C11 . 1.4241(13) yes O21 . C25 . 1.4241(15) yes C2 . C3 . 1.5138(15) yes C3 . C4 . 1.5376(16) yes C3 . C16 . 1.5306(16) yes C3 . H31 . 0.979(14) no C4 . C5 . 1.5248(15) yes C4 . H41 . 0.988(14) no C4 . H42 . 1.002(14) no C5 . C6 . 1.5482(15) yes C5 . H51 . 0.966(15) no C5 . H52 . 0.999(14) no C6 . C7 . 1.5492(14) yes C6 . C15 . 1.5264(14) yes C6 . C19 . 1.5489(15) yes C7 . C8 . 1.5295(15) yes C7 . C12 . 1.5421(14) yes C7 . H71 . 0.995(13) no C8 . C9 . 1.4780(15) yes C9 . C10 . 1.3364(16) yes C9 . H91 . 0.955(14) no C10 . C11 . 1.5142(15) yes C10 . C22 . 1.5159(15) yes C11 . C12 . 1.5300(14) yes C11 . H111 . 1.009(14) no C12 . C13 . 1.5322(15) yes C12 . H121 . 0.984(14) no C13 . C14 . 1.5021(15) yes C13 . H131 . 1.016(14) no C13 . H132 . 0.980(14) no C14 . C15 . 1.3341(15) yes C14 . H141 . 0.978(14) no C15 . C16 . 1.5128(14) yes C16 . C17 . 1.5316(16) yes C16 . H161 . 0.970(14) no C17 . H171 . 1.019(16) no C17 . H172 . 0.955(16) no C19 . H191 . 1.010(14) no C19 . H192 . 0.959(15) no C19 . H193 . 0.996(14) no C22 . C23 . 1.5193(18) yes C22 . C24 . 1.5309(19) yes C22 . H221 . 0.976(15) no C23 . H231 . 1.001(17) no C23 . H232 . 1.025(16) no C23 . H233 . 1.026(17) no C24 . H241 . 1.014(17) no C24 . H242 . 0.989(18) no C24 . H243 . 0.961(18) no C25 . H251 . 0.993(16) no C25 . H252 . 0.989(17) no C25 . H253 . 1.018(17) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C17 . 109.60(9) yes C11 . O21 . C25 . 113.42(9) yes O1 . C2 . O18 . 120.70(11) yes O1 . C2 . C3 . 110.69(10) yes O18 . C2 . C3 . 128.60(12) yes C2 . C3 . C4 . 109.87(9) yes C2 . C3 . C16 . 102.84(9) yes C4 . C3 . C16 . 113.93(9) yes C2 . C3 . H31 . 107.8(8) no C4 . C3 . H31 . 109.4(8) no C16 . C3 . H31 . 112.6(8) no C3 . C4 . C5 . 109.81(9) yes C3 . C4 . H41 . 109.1(8) no C5 . C4 . H41 . 109.6(8) no C3 . C4 . H42 . 110.1(8) no C5 . C4 . H42 . 111.5(8) no H41 . C4 . H42 . 106.7(11) no C4 . C5 . C6 . 112.51(9) yes C4 . C5 . H51 . 107.9(8) no C6 . C5 . H51 . 110.9(8) no C4 . C5 . H52 . 110.2(8) no C6 . C5 . H52 . 106.7(8) no H51 . C5 . H52 . 108.6(11) no C5 . C6 . C7 . 111.25(8) yes C5 . C6 . C15 . 112.10(9) yes C7 . C6 . C15 . 107.34(8) yes C5 . C6 . C19 . 106.79(9) yes C7 . C6 . C19 . 109.05(9) yes C15 . C6 . C19 . 110.30(8) yes C6 . C7 . C8 . 116.30(9) yes C6 . C7 . C12 . 110.99(8) yes C8 . C7 . C12 . 106.59(8) yes C6 . C7 . H71 . 109.4(7) no C8 . C7 . H71 . 105.7(7) no C12 . C7 . H71 . 107.4(7) no C7 . C8 . O20 . 124.91(10) yes C7 . C8 . C9 . 116.08(9) yes O20 . C8 . C9 . 119.01(10) yes C8 . C9 . C10 . 124.40(10) yes C8 . C9 . H91 . 113.9(8) no C10 . C9 . H91 . 121.7(8) no C9 . C10 . C11 . 119.23(10) yes C9 . C10 . C22 . 123.35(10) yes C11 . C10 . C22 . 117.36(9) yes C10 . C11 . O21 . 108.23(9) yes C10 . C11 . C12 . 112.91(9) yes O21 . C11 . C12 . 112.64(9) yes C10 . C11 . H111 . 107.0(8) no O21 . C11 . H111 . 108.6(7) no C12 . C11 . H111 . 107.3(8) no C7 . C12 . C11 . 110.20(9) yes C7 . C12 . C13 . 109.58(9) yes C11 . C12 . C13 . 113.67(9) yes C7 . C12 . H121 . 108.3(8) no C11 . C12 . H121 . 106.8(8) no C13 . C12 . H121 . 108.1(8) no C12 . C13 . C14 . 112.84(9) yes C12 . C13 . H131 . 109.7(8) no C14 . C13 . H131 . 108.0(8) no C12 . C13 . H132 . 110.2(8) no C14 . C13 . H132 . 108.8(8) no H131 . C13 . H132 . 106.9(11) no C13 . C14 . C15 . 126.19(10) yes C13 . C14 . H141 . 116.4(8) no C15 . C14 . H141 . 117.4(8) no C6 . C15 . C14 . 121.44(9) yes C6 . C15 . C16 . 119.37(9) yes C14 . C15 . C16 . 119.19(10) yes C3 . C16 . C15 . 117.52(9) yes C3 . C16 . C17 . 101.62(9) yes C15 . C16 . C17 . 114.12(10) yes C3 . C16 . H161 . 108.7(8) no C15 . C16 . H161 . 107.7(8) no C17 . C16 . H161 . 106.5(8) no C16 . C17 . O1 . 105.11(10) yes C16 . C17 . H171 . 112.6(8) no O1 . C17 . H171 . 107.3(8) no C16 . C17 . H172 . 112.2(9) no O1 . C17 . H172 . 106.8(9) no H171 . C17 . H172 . 112.2(13) no C6 . C19 . H191 . 111.3(8) no C6 . C19 . H192 . 109.5(8) no H191 . C19 . H192 . 108.8(11) no C6 . C19 . H193 . 110.3(8) no H191 . C19 . H193 . 108.1(11) no H192 . C19 . H193 . 108.8(12) no C10 . C22 . C23 . 113.86(10) yes C10 . C22 . C24 . 109.95(11) yes C23 . C22 . C24 . 110.30(12) yes C10 . C22 . H221 . 105.7(8) no C23 . C22 . H221 . 108.2(8) no C24 . C22 . H221 . 108.6(8) no C22 . C23 . H231 . 110.0(9) no C22 . C23 . H232 . 109.8(9) no H231 . C23 . H232 . 106.5(13) no C22 . C23 . H233 . 111.9(9) no H231 . C23 . H233 . 108.6(12) no H232 . C23 . H233 . 109.9(13) no C22 . C24 . H241 . 110.5(10) no C22 . C24 . H242 . 108.6(10) no H241 . C24 . H242 . 108.6(13) no C22 . C24 . H243 . 109.7(10) no H241 . C24 . H243 . 107.4(14) no H242 . C24 . H243 . 112.1(14) no O21 . C25 . H251 . 108.5(10) no O21 . C25 . H252 . 108.9(9) no H251 . C25 . H252 . 110.1(13) no O21 . C25 . H253 . 111.2(9) no H251 . C25 . H253 . 109.6(13) no H252 . C25 . H253 . 108.5(13) no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O18 3.053(1) . 3_546 no O1 C2 3.236(2) . 3_546 no O1 C3 3.490(1) . 3_546 no O1 O18 3.495(1) . 3_556 no O18 C17 3.277(2) . 3_556 no O18 C16 3.282(1) . 3_546 no O18 C2 3.347(2) . 3_546 no O18 C2 3.415(2) . 3_556 no O18 C3 3.439(2) . 3_546 no O18 C13 3.537(2) . 4_465 no O20 C19 3.478(2) . 1_565 no O20 C25 3.570(2) . 4_465 no C2 C2 3.3340(4) . 3_556 no C2 C2 3.3340(4) . 3_546 no C8 C23 3.562(2) . 3_647 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C2 C3 C4 . . . . -106.5(1) no O1 C2 C3 C16 . . . . 15.1(1) no O1 C17 C16 C3 . . . . 31.5(1) no O1 C17 C16 C15 . . . . 159.0(1) no O18 C2 O1 C17 . . . . -173.3(1) no O18 C2 C3 C4 . . . . 71.8(2) no O18 C2 C3 C16 . . . . -166.5(1) no O20 C8 C7 C6 . . . . 12.3(2) no O20 C8 C7 C12 . . . . 136.6(1) no O20 C8 C9 C10 . . . . -164.7(1) no O21 C11 C10 C9 . . . . 147.6(1) no O21 C11 C10 C22 . . . . -35.2(1) no O21 C11 C12 C7 . . . . -175.47(9) no O21 C11 C12 C13 . . . . -52.0(1) no C2 O1 C17 C16 . . . . -23.7(1) no C2 C3 C4 C5 . . . . 166.9(1) no C2 C3 C16 C15 . . . . -152.87(9) no C2 C3 C16 C17 . . . . -27.6(1) no C3 C2 O1 C17 . . . . 5.2(1) no C3 C4 C5 C6 . . . . -61.6(1) no C3 C16 C15 C6 . . . . 24.3(1) no C3 C16 C15 C14 . . . . -156.3(1) no C4 C3 C16 C15 . . . . -34.0(1) no C4 C3 C16 C17 . . . . 91.3(1) no C4 C5 C6 C7 . . . . 171.01(9) no C4 C5 C6 C15 . . . . 50.8(1) no C4 C5 C6 C19 . . . . -70.1(1) no C5 C4 C3 C16 . . . . 52.1(1) no C5 C6 C7 C8 . . . . -57.9(1) no C5 C6 C7 C12 . . . . -179.97(9) no C5 C6 C15 C14 . . . . 148.8(1) no C5 C6 C15 C16 . . . . -31.8(1) no C6 C7 C8 C9 . . . . -167.2(1) no C6 C7 C12 C11 . . . . -170.95(8) no C6 C7 C12 C13 . . . . 63.3(1) no C6 C15 C14 C13 . . . . -0.9(2) no C6 C15 C16 C17 . . . . -94.6(1) no C7 C6 C15 C14 . . . . 26.3(2) no C7 C6 C15 C16 . . . . -154.2(1) no C7 C8 C9 C10 . . . . 14.8(2) no C7 C12 C11 C10 . . . . -52.5(1) no C7 C12 C13 C14 . . . . -35.2(1) no C8 C7 C6 C15 . . . . 65.1(1) no C8 C7 C6 C19 . . . . -175.4(1) no C8 C7 C12 C11 . . . . 61.5(1) no C8 C7 C12 C13 . . . . -64.29(9) no C8 C9 C10 C11 . . . . -3.1(2) no C8 C9 C10 C22 . . . . 179.9(1) no C9 C8 C7 C12 . . . . -42.9(1) no C9 C10 C11 C12 . . . . 22.3(2) no C9 C10 C22 C23 . . . . -8.8(2) no C9 C10 C22 C24 . . . . 115.5(2) no C10 C11 O21 C25 . . . . 161.27(8) no C10 C11 C12 C13 . . . . 70.9(2) no C11 C10 C22 C23 . . . . 174.1(1) no C11 C10 C22 C24 . . . . -61.5(2) no C11 C12 C13 C14 . . . . -159.0(1) no C12 C7 C6 C15 . . . . -57.0(1) no C12 C7 C6 C19 . . . . 62.5(1) no C12 C11 O21 C25 . . . . -73.2(1) no C12 C11 C10 C22 . . . . -160.6(1) no C12 C13 C14 C15 . . . . 5.3(2) no C13 C14 C15 C16 . . . . 179.6(1) no C14 C15 C6 C19 . . . . -92.4(1) no C14 C15 C16 C17 . . . . 84.9(1) no C16 C15 C6 C19 . . . . 87.1(1) no #------------------------------------------------------------------------------ #===END data_she0616 _database_code_depnum_ccdc_archive 'CCDC 658575' _audit_creation_date 06-06-28 _audit_creation_method CRYSTALS_ver_12.18 _audit_update_record ; 2006-06-29 - Report on C21 H26 O3 by Anthony C. Willis for Natalie Miller and Mick Sherburn 2006-06-29 - passes checkcif tests with minor warnings ; _oxford_structure_analysis_title '6281225 she0616' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.6828(3) _cell_length_b 10.5296(5) _cell_length_c 35.1809(15) _cell_angle_alpha 90 _cell_angle_beta 97.868(2) _cell_angle_gamma 90 _cell_volume 3553.1(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C21 H26 O3 # Dc = 1.22 Fooo = 1408.00 Mu = 0.80 M = 652.87 # Found Formula = C21 H26 O3 # Dc = 1.22 FOOO = 1408.00 Mu = 0.80 M = 652.87 _chemical_formula_sum 'C21 H26 O3' _chemical_formula_moiety 'C21 H26 O3' _chemical_compound_source ? _chemical_formula_weight 326.44 _cell_measurement_reflns_used 45271 _cell_measurement_theta_min 3 _cell_measurement_theta_max 25 _cell_measurement_temperature 200 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.03 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_max 0.33 _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.080 # Sheldrick geometric approximatio 0.98 1.00 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 1 0 0.150 3 -4 0 0.138 -1 1 0 0.152 -3 -14 0 0.127 0 0 1 0.001 0 0 -1 0.025 0 1 0 0.199 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 0.7 deg at rate 84 sec/frame, crystal-detector distance 55mm, multiple scan sets so over 95 percent of data collected with 4-fold redundancy or more. ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_cell_refinement 'Denzo/Scalepack ' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Watkin et al 2003)' _computing_publication_material 'CRYSTALS ' _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 29916 _reflns_number_total 6212 _diffrn_reflns_av_R_equivalents 0.093 # Number of reflections with Friedels Law is 6212 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 6285 _diffrn_reflns_theta_min 2.560 _diffrn_reflns_theta_max 25.038 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.038 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 41 _oxford_diffrn_Wilson_B_factor 2.76 _oxford_diffrn_Wilson_scale 24.95 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.22 _refine_diff_density_max 0.25 _refine_ls_number_reflns 2641 _refine_ls_number_restraints 0 _refine_ls_number_parameters 433 #_refine_ls_R_factor_ref 0.0534 _refine_ls_wR_factor_ref 0.0494 _refine_ls_goodness_of_fit_ref 1.1722 #_reflns_number_all 6191 _refine_ls_R_factor_all 0.1597 _refine_ls_wR_factor_all 0.0771 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.5\s(I) _reflns_number_gt 2641 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_gt 0.0494 _refine_ls_shift/su_max 0.000361 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.91 1.87 1.51 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O101 O 1.2719(2) 0.1745(2) 0.71214(7) 0.0504 1.0000 Uani . . . . . . O118 O 1.2295(2) 0.1223(2) 0.77064(8) 0.0610 1.0000 Uani . . . . . . O123 O 0.5656(2) 0.2727(2) 0.53354(6) 0.0528 1.0000 Uani . . . . . . C102 C 1.1854(4) 0.1451(3) 0.73746(11) 0.0473 1.0000 Uani . . . . . . C103 C 1.0346(3) 0.1473(3) 0.71872(10) 0.0454 1.0000 Uani . . . . . . C104 C 0.9648(3) 0.2703(3) 0.72935(9) 0.0436 1.0000 Uani . . . . . . C105 C 0.8269(3) 0.2916(3) 0.70376(9) 0.0376 1.0000 Uani . . . . . . C106 C 0.8457(3) 0.3067(3) 0.66097(8) 0.0323 1.0000 Uani . . . . . . C107 C 0.7039(3) 0.3144(3) 0.63524(8) 0.0343 1.0000 Uani . . . . . . C108 C 0.5858(3) 0.3660(3) 0.64844(9) 0.0383 1.0000 Uani . . . . . . C109 C 0.4633(3) 0.3851(3) 0.62403(9) 0.0401 1.0000 Uani . . . . . . C110 C 0.4521(3) 0.3554(3) 0.58508(9) 0.0388 1.0000 Uani . . . . . . C111 C 0.5680(3) 0.3008(3) 0.57267(8) 0.0365 1.0000 Uani . . . . . . C112 C 0.6922(3) 0.2788(3) 0.59656(9) 0.0364 1.0000 Uani . . . . . . C113 C 0.8151(3) 0.2213(4) 0.58109(10) 0.0494 1.0000 Uani . . . . . . C114 C 0.9178(4) 0.1633(3) 0.61169(10) 0.0486 1.0000 Uani . . . . . . C115 C 0.9341(3) 0.2002(3) 0.64824(9) 0.0354 1.0000 Uani . . . . . . C116 C 1.0489(3) 0.1417(3) 0.67585(10) 0.0437 1.0000 Uani . . . . . . C117 C 1.1916(3) 0.2044(4) 0.67534(10) 0.0483 1.0000 Uani . . . . . . C119 C 0.9177(3) 0.4372(3) 0.65616(9) 0.0418 1.0000 Uani . . . . . . C120 C 0.3224(4) 0.3922(3) 0.55750(10) 0.0507 1.0000 Uani . . . . . . C121 C 0.3295(6) 0.5293(5) 0.54617(16) 0.1053 1.0000 Uani . . . . . . C122 C 0.1892(5) 0.3623(7) 0.57169(16) 0.1314 1.0000 Uani . . . . . . C124 C 0.5101(4) 0.1511(4) 0.52318(11) 0.0629 1.0000 Uani . . . . . . O1 O 0.2269(2) 0.0483(2) 0.27396(7) 0.0511 1.0000 Uani . . . . . . O18 O 0.2761(3) 0.0149(2) 0.21510(8) 0.0571 1.0000 Uani . . . . . . O23 O 0.9414(2) 0.0735(2) 0.45446(6) 0.0444 1.0000 Uani . . . . . . C2 C 0.3183(4) 0.0292(3) 0.24855(11) 0.0438 1.0000 Uani . . . . . . C3 C 0.4649(3) 0.0344(3) 0.26875(9) 0.0405 1.0000 Uani . . . . . . C4 C 0.5277(3) 0.1653(3) 0.26345(9) 0.0367 1.0000 Uani . . . . . . C5 C 0.6625(3) 0.1815(3) 0.29024(8) 0.0348 1.0000 Uani . . . . . . C6 C 0.6425(3) 0.1777(3) 0.33310(8) 0.0316 1.0000 Uani . . . . . . C7 C 0.7840(3) 0.1805(3) 0.35876(8) 0.0306 1.0000 Uani . . . . . . C8 C 0.8973(3) 0.2457(3) 0.34806(9) 0.0386 1.0000 Uani . . . . . . C9 C 1.0217(3) 0.2536(3) 0.37187(9) 0.0409 1.0000 Uani . . . . . . C10 C 1.0401(3) 0.2007(3) 0.40832(8) 0.0371 1.0000 Uani . . . . . . C11 C 0.9268(3) 0.1359(3) 0.41900(8) 0.0334 1.0000 Uani . . . . . . C12 C 0.8004(3) 0.1229(3) 0.39523(9) 0.0322 1.0000 Uani . . . . . . C13 C 0.6841(3) 0.0454(3) 0.40779(9) 0.0424 1.0000 Uani . . . . . . C14 C 0.5796(3) 0.0022(3) 0.37524(9) 0.0416 1.0000 Uani . . . . . . C15 C 0.5593(3) 0.0605(3) 0.34124(9) 0.0339 1.0000 Uani . . . . . . C16 C 0.4473(3) 0.0103(3) 0.31071(10) 0.0436 1.0000 Uani . . . . . . C17 C 0.3015(3) 0.0671(4) 0.31227(10) 0.0530 1.0000 Uani . . . . . . C19 C 0.5636(3) 0.2991(3) 0.34285(9) 0.0392 1.0000 Uani . . . . . . C20 C 1.1767(4) 0.2138(3) 0.43446(10) 0.0489 1.0000 Uani . . . . . . C21 C 1.2058(5) 0.3518(5) 0.44520(13) 0.0837 1.0000 Uani . . . . . . C22 C 1.2976(4) 0.1591(5) 0.41594(12) 0.0728 1.0000 Uani . . . . . . C24 C 0.9006(5) 0.1484(4) 0.48521(10) 0.0635 1.0000 Uani . . . . . . H31 H 0.5230 -0.0336 0.25903 0.0474 1.0000 Uiso R . . . . . H41 H 0.4602 0.2322 0.26910 0.0434 1.0000 Uiso R . . . . . H42 H 0.5466 0.1742 0.23634 0.0434 1.0000 Uiso R . . . . . H51 H 0.7044 0.2652 0.28477 0.0418 1.0000 Uiso R . . . . . H52 H 0.7276 0.1116 0.28524 0.0418 1.0000 Uiso R . . . . . H81 H 0.8879 0.2880 0.32238 0.0457 1.0000 Uiso R . . . . . H91 H 1.1016 0.2988 0.36264 0.0485 1.0000 Uiso R . . . . . H131 H 0.7254 -0.0311 0.42185 0.0509 1.0000 Uiso R . . . . . H132 H 0.6352 0.0983 0.42543 0.0509 1.0000 Uiso R . . . . . H141 H 0.5218 -0.0743 0.37909 0.0500 1.0000 Uiso R . . . . . H161 H 0.4408 -0.0836 0.31436 0.0513 1.0000 Uiso R . . . . . H171 H 0.2536 0.0217 0.33174 0.0630 1.0000 Uiso R . . . . . H172 H 0.3085 0.1595 0.31871 0.0630 1.0000 Uiso R . . . . . H191 H 0.5503 0.2973 0.37053 0.0472 1.0000 Uiso R . . . . . H192 H 0.6190 0.3758 0.33775 0.0472 1.0000 Uiso R . . . . . H193 H 0.4706 0.3022 0.32654 0.0472 1.0000 Uiso R . . . . . H201 H 1.1696 0.1651 0.45851 0.0572 1.0000 Uiso R . . . . . H211 H 1.2965 0.3582 0.46248 0.0959 1.0000 Uiso R . . . . . H212 H 1.1292 0.3854 0.45878 0.0959 1.0000 Uiso R . . . . . H213 H 1.2108 0.4027 0.42143 0.0959 1.0000 Uiso R . . . . . H221 H 1.3864 0.1692 0.43390 0.0861 1.0000 Uiso R . . . . . H222 H 1.2804 0.0669 0.41032 0.0861 1.0000 Uiso R . . . . . H223 H 1.3052 0.2055 0.39151 0.0861 1.0000 Uiso R . . . . . H241 H 0.9139 0.0977 0.50948 0.0767 1.0000 Uiso R . . . . . H242 H 0.9592 0.2268 0.48862 0.0767 1.0000 Uiso R . . . . . H243 H 0.8002 0.1727 0.47893 0.0767 1.0000 Uiso R . . . . . H1031 H 0.9831 0.0714 0.72654 0.0533 1.0000 Uiso R . . . . . H1041 H 0.9473 0.2650 0.75666 0.0516 1.0000 Uiso R . . . . . H1042 H 1.0283 0.3433 0.72632 0.0516 1.0000 Uiso R . . . . . H1051 H 0.7826 0.3704 0.71237 0.0448 1.0000 Uiso R . . . . . H1052 H 0.7646 0.2172 0.70635 0.0448 1.0000 Uiso R . . . . . H1081 H 0.5904 0.3894 0.67613 0.0456 1.0000 Uiso R . . . . . H1091 H 0.3807 0.4210 0.63452 0.0477 1.0000 Uiso R . . . . . H1131 H 0.8631 0.2892 0.56796 0.0597 1.0000 Uiso R . . . . . H1132 H 0.7806 0.1538 0.56212 0.0597 1.0000 Uiso R . . . . . H1141 H 0.9780 0.0927 0.60433 0.0586 1.0000 Uiso R . . . . . H1161 H 1.0571 0.0504 0.66863 0.0515 1.0000 Uiso R . . . . . H1171 H 1.1810 0.2984 0.67216 0.0578 1.0000 Uiso R . . . . . H1172 H 1.2382 0.1691 0.65396 0.0578 1.0000 Uiso R . . . . . H1191 H 0.9310 0.4491 0.62869 0.0508 1.0000 Uiso R . . . . . H1192 H 1.0105 0.4390 0.67262 0.0508 1.0000 Uiso R . . . . . H1193 H 0.8578 0.5071 0.66408 0.0508 1.0000 Uiso R . . . . . H1201 H 0.3245 0.3411 0.53363 0.0594 1.0000 Uiso R . . . . . H1211 H 0.2441 0.5520 0.52813 0.1184 1.0000 Uiso R . . . . . H1212 H 0.3352 0.5839 0.56959 0.1184 1.0000 Uiso R . . . . . H1213 H 0.4140 0.5434 0.53324 0.1184 1.0000 Uiso R . . . . . H1221 H 0.1097 0.3891 0.55214 0.1557 1.0000 Uiso R . . . . . H1222 H 0.1844 0.4089 0.59624 0.1557 1.0000 Uiso R . . . . . H1223 H 0.1835 0.2689 0.57627 0.1557 1.0000 Uiso R . . . . . H1241 H 0.5112 0.1370 0.49511 0.0742 1.0000 Uiso R . . . . . H1242 H 0.5679 0.0845 0.53810 0.0742 1.0000 Uiso R . . . . . H1243 H 0.4120 0.1460 0.52900 0.0742 1.0000 Uiso 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 O101 0.0335(13) 0.0545(15) 0.0612(16) 0.0103(13) -0.0003(12) 0.0047(12) O118 0.0498(16) 0.0604(17) 0.0666(18) 0.0266(14) -0.0137(14) -0.0071(13) O123 0.0561(16) 0.0624(17) 0.0383(14) -0.0062(12) 0.0007(11) -0.0083(13) C102 0.044(2) 0.031(2) 0.063(2) 0.0133(18) -0.009(2) 0.0028(16) C103 0.0367(19) 0.035(2) 0.062(2) 0.0087(17) -0.0037(17) -0.0045(16) C104 0.0326(18) 0.060(2) 0.0363(18) 0.0079(16) -0.0018(14) -0.0051(17) C105 0.0365(18) 0.041(2) 0.0346(17) 0.0028(15) 0.0024(14) 0.0009(15) C106 0.0325(17) 0.0307(18) 0.0333(17) 0.0009(15) 0.0035(13) -0.0027(15) C107 0.0370(19) 0.0331(18) 0.0331(18) 0.0033(15) 0.0062(14) 0.0012(15) C108 0.040(2) 0.043(2) 0.0304(17) -0.0008(15) 0.0014(15) 0.0048(16) C109 0.039(2) 0.0373(19) 0.043(2) 0.0003(15) 0.0012(16) 0.0031(16) C110 0.0333(19) 0.0386(19) 0.0423(19) 0.0046(16) -0.0032(15) -0.0012(15) C111 0.037(2) 0.046(2) 0.0260(17) -0.0004(15) 0.0007(15) -0.0052(16) C112 0.0395(19) 0.0357(19) 0.0358(19) -0.0024(14) 0.0117(15) -0.0021(15) C113 0.038(2) 0.066(2) 0.045(2) -0.0135(18) 0.0089(16) -0.0012(18) C114 0.039(2) 0.052(2) 0.056(2) -0.0130(19) 0.0086(17) 0.0063(17) C115 0.0248(17) 0.0295(18) 0.052(2) -0.0050(15) 0.0045(15) 0.0004(14) C116 0.040(2) 0.0309(18) 0.058(2) -0.0097(17) -0.0018(17) 0.0034(15) C117 0.0332(19) 0.056(2) 0.056(2) -0.0060(18) 0.0045(16) 0.0103(17) C119 0.0410(19) 0.0405(19) 0.045(2) -0.0014(16) 0.0109(16) -0.0044(17) C120 0.052(2) 0.053(2) 0.043(2) 0.0034(18) -0.0063(18) 0.0099(18) C121 0.116(4) 0.073(3) 0.107(4) 0.031(3) -0.057(3) 0.008(3) C122 0.042(3) 0.245(8) 0.102(4) 0.065(5) -0.008(3) -0.005(4) C124 0.064(3) 0.070(3) 0.052(2) -0.014(2) -0.0031(19) 0.000(2) O1 0.0348(14) 0.0539(15) 0.0613(17) 0.0043(12) -0.0045(13) -0.0053(12) O18 0.0553(16) 0.0490(15) 0.0598(17) -0.0133(12) -0.0179(13) 0.0048(12) O23 0.0540(15) 0.0489(14) 0.0308(13) 0.0100(11) 0.0079(11) 0.0100(12) C2 0.047(2) 0.0260(17) 0.054(2) -0.0048(16) -0.010(2) 0.0037(16) C3 0.0365(19) 0.033(2) 0.049(2) -0.0099(15) -0.0050(15) 0.0118(15) C4 0.0341(19) 0.041(2) 0.0332(17) -0.0029(15) -0.0008(14) 0.0002(15) C5 0.0338(18) 0.0376(18) 0.0333(17) 0.0033(15) 0.0052(14) -0.0022(15) C6 0.0330(18) 0.0313(16) 0.0298(16) 0.0059(14) 0.0020(13) -0.0007(15) C7 0.0329(18) 0.0261(16) 0.0333(17) -0.0029(14) 0.0061(14) 0.0014(14) C8 0.0436(19) 0.0368(19) 0.0340(17) 0.0058(15) 0.0003(15) -0.0093(17) C9 0.0378(19) 0.0409(19) 0.042(2) 0.0036(16) -0.0003(15) -0.0133(17) C10 0.0361(19) 0.0388(19) 0.0343(19) 0.0046(15) -0.0029(15) -0.0031(16) C11 0.0372(19) 0.0362(18) 0.0250(16) 0.0038(14) -0.0019(14) 0.0085(15) C12 0.0333(18) 0.0305(17) 0.0338(18) 0.0058(14) 0.0080(14) 0.0093(14) C13 0.0326(18) 0.053(2) 0.0416(19) 0.0145(17) 0.0058(15) 0.0012(17) C14 0.0342(19) 0.0421(19) 0.049(2) 0.0084(17) 0.0068(16) -0.0031(16) C15 0.0298(17) 0.0339(17) 0.0377(18) -0.0008(15) 0.0035(14) -0.0005(14) C16 0.044(2) 0.0273(18) 0.057(2) 0.0085(15) -0.0023(17) -0.0049(15) C17 0.037(2) 0.066(2) 0.054(2) 0.010(2) 0.0010(17) -0.0081(19) C19 0.045(2) 0.0294(18) 0.0436(19) -0.0003(15) 0.0071(16) 0.0029(15) C20 0.042(2) 0.058(2) 0.043(2) 0.0054(18) -0.0075(16) -0.0033(17) C21 0.081(3) 0.090(4) 0.069(3) -0.006(3) -0.030(2) -0.016(3) C22 0.034(2) 0.114(4) 0.067(3) 0.006(3) -0.0043(19) 0.007(2) C24 0.075(3) 0.086(3) 0.0308(19) 0.002(2) 0.0111(18) 0.016(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2238(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O101 . C102 . 1.340(4) yes O101 . C117 . 1.450(4) yes O118 . C102 . 1.211(4) yes O123 . C111 . 1.405(3) yes O123 . C124 . 1.417(4) yes C102 . C103 . 1.517(5) yes C103 . C104 . 1.530(5) yes C103 . C116 . 1.535(5) yes C103 . H1031 . 1.000 no C104 . C105 . 1.522(4) yes C104 . H1041 . 1.000 no C104 . H1042 . 1.000 no C105 . C106 . 1.549(4) yes C105 . H1051 . 1.000 no C105 . H1052 . 1.000 no C106 . C107 . 1.540(4) yes C106 . C115 . 1.515(4) yes C106 . C119 . 1.561(4) yes C107 . C108 . 1.400(4) yes C107 . C112 . 1.401(4) yes C108 . C109 . 1.381(4) yes C108 . H1081 . 1.000 no C109 . C110 . 1.395(4) yes C109 . H1091 . 1.000 no C110 . C111 . 1.384(4) yes C110 . C120 . 1.528(4) yes C111 . C112 . 1.389(4) yes C112 . C113 . 1.502(5) yes C113 . C114 . 1.493(5) yes C113 . H1131 . 1.000 no C113 . H1132 . 1.000 no C114 . C115 . 1.332(4) yes C114 . H1141 . 1.000 no C115 . C116 . 1.504(4) yes C116 . C117 . 1.533(5) yes C116 . H1161 . 1.000 no C117 . H1171 . 1.000 no C117 . H1172 . 1.000 no C119 . H1191 . 1.000 no C119 . H1192 . 1.000 no C119 . H1193 . 1.000 no C120 . C121 . 1.502(6) yes C120 . C122 . 1.479(6) yes C120 . H1201 . 1.000 no C121 . H1211 . 1.000 no C121 . H1212 . 1.000 no C121 . H1213 . 1.000 no C122 . H1221 . 1.000 no C122 . H1222 . 1.000 no C122 . H1223 . 1.000 no C124 . H1241 . 1.000 no C124 . H1242 . 1.000 no C124 . H1243 . 1.000 no O1 . C2 . 1.356(4) yes O1 . C17 . 1.453(4) yes O18 . C2 . 1.201(4) yes O23 . C11 . 1.400(3) yes O23 . C24 . 1.437(4) yes C2 . C3 . 1.499(5) yes C3 . C4 . 1.528(5) yes C3 . C16 . 1.530(5) yes C3 . H31 . 1.000 no C4 . C5 . 1.511(4) yes C4 . H41 . 1.000 no C4 . H42 . 1.000 no C5 . C6 . 1.547(4) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C6 . C7 . 1.534(4) yes C6 . C15 . 1.523(4) yes C6 . C19 . 1.551(4) yes C7 . C8 . 1.390(4) yes C7 . C12 . 1.408(4) yes C8 . C9 . 1.372(4) yes C8 . H81 . 1.000 no C9 . C10 . 1.387(4) yes C9 . H91 . 1.000 no C10 . C11 . 1.387(4) yes C10 . C20 . 1.510(4) yes C11 . C12 . 1.391(4) yes C12 . C13 . 1.505(4) yes C13 . C14 . 1.492(4) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C14 . C15 . 1.335(4) yes C14 . H141 . 1.000 no C15 . C16 . 1.513(4) yes C16 . C17 . 1.541(5) yes C16 . H161 . 1.000 no C17 . H171 . 1.000 no C17 . H172 . 1.000 no C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C20 . C21 . 1.518(6) yes C20 . C22 . 1.528(5) yes C20 . H201 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no C22 . H221 . 1.000 no C22 . H222 . 1.000 no C22 . H223 . 1.000 no C24 . H241 . 1.000 no C24 . H242 . 1.000 no C24 . H243 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C102 . O101 . C117 . 109.6(2) yes C111 . O123 . C124 . 113.4(3) yes O101 . C102 . O118 . 121.1(3) yes O101 . C102 . C103 . 111.1(3) yes O118 . C102 . C103 . 127.8(4) yes C102 . C103 . C104 . 109.7(3) yes C102 . C103 . C116 . 102.5(3) yes C104 . C103 . C116 . 112.0(3) yes C102 . C103 . H1031 . 110.8 no C104 . C103 . H1031 . 110.8 no C116 . C103 . H1031 . 110.8 no C103 . C104 . C105 . 111.2(3) yes C103 . C104 . H1041 . 109.0 no C105 . C104 . H1041 . 109.0 no C103 . C104 . H1042 . 109.0 no C105 . C104 . H1042 . 109.0 no H1041 . C104 . H1042 . 109.5 no C104 . C105 . C106 . 112.3(3) yes C104 . C105 . H1051 . 108.8 no C106 . C105 . H1051 . 108.8 no C104 . C105 . H1052 . 108.8 no C106 . C105 . H1052 . 108.8 no H1051 . C105 . H1052 . 109.5 no C105 . C106 . C107 . 111.3(2) yes C105 . C106 . C115 . 111.0(2) yes C107 . C106 . C115 . 111.1(2) yes C105 . C106 . C119 . 108.0(2) yes C107 . C106 . C119 . 105.4(2) yes C115 . C106 . C119 . 109.9(2) yes C106 . C107 . C108 . 121.9(3) yes C106 . C107 . C112 . 120.2(3) yes C108 . C107 . C112 . 117.7(3) yes C107 . C108 . C109 . 121.4(3) yes C107 . C108 . H1081 . 119.3 no C109 . C108 . H1081 . 119.3 no C108 . C109 . C110 . 121.5(3) yes C108 . C109 . H1091 . 119.2 no C110 . C109 . H1091 . 119.2 no C109 . C110 . C111 . 116.4(3) yes C109 . C110 . C120 . 120.9(3) yes C111 . C110 . C120 . 122.4(3) yes O123 . C111 . C110 . 119.4(3) yes O123 . C111 . C112 . 117.1(3) yes C110 . C111 . C112 . 123.4(3) yes C107 . C112 . C111 . 119.4(3) yes C107 . C112 . C113 . 119.8(3) yes C111 . C112 . C113 . 120.8(3) yes C112 . C113 . C114 . 112.7(3) yes C112 . C113 . H1131 . 108.7 no C114 . C113 . H1131 . 108.7 no C112 . C113 . H1132 . 108.7 no C114 . C113 . H1132 . 108.6 no H1131 . C113 . H1132 . 109.5 no C113 . C114 . C115 . 123.8(3) yes C113 . C114 . H1141 . 118.1 no C115 . C114 . H1141 . 118.1 no C106 . C115 . C114 . 120.3(3) yes C106 . C115 . C116 . 120.6(3) yes C114 . C115 . C116 . 118.9(3) yes C103 . C116 . C115 . 117.4(3) yes C103 . C116 . C117 . 101.4(3) yes C115 . C116 . C117 . 113.8(3) yes C103 . C116 . H1161 . 107.9 no C115 . C116 . H1161 . 107.9 no C117 . C116 . H1161 . 107.9 no C116 . C117 . O101 . 105.7(3) yes C116 . C117 . H1171 . 110.4 no O101 . C117 . H1171 . 110.4 no C116 . C117 . H1172 . 110.4 no O101 . C117 . H1172 . 110.4 no H1171 . C117 . H1172 . 109.5 no C106 . C119 . H1191 . 109.5 no C106 . C119 . H1192 . 109.5 no H1191 . C119 . H1192 . 109.5 no C106 . C119 . H1193 . 109.5 no H1191 . C119 . H1193 . 109.5 no H1192 . C119 . H1193 . 109.5 no C110 . C120 . C121 . 110.4(3) yes C110 . C120 . C122 . 114.2(3) yes C121 . C120 . C122 . 111.6(4) yes C110 . C120 . H1201 . 106.7 no C121 . C120 . H1201 . 106.7 no C122 . C120 . H1201 . 106.7 no C120 . C121 . H1211 . 109.5 no C120 . C121 . H1212 . 109.5 no H1211 . C121 . H1212 . 109.5 no C120 . C121 . H1213 . 109.5 no H1211 . C121 . H1213 . 109.5 no H1212 . C121 . H1213 . 109.5 no C120 . C122 . H1221 . 109.5 no C120 . C122 . H1222 . 109.5 no H1221 . C122 . H1222 . 109.5 no C120 . C122 . H1223 . 109.5 no H1221 . C122 . H1223 . 109.5 no H1222 . C122 . H1223 . 109.5 no O123 . C124 . H1241 . 109.5 no O123 . C124 . H1242 . 109.5 no H1241 . C124 . H1242 . 109.5 no O123 . C124 . H1243 . 109.5 no H1241 . C124 . H1243 . 109.5 no H1242 . C124 . H1243 . 109.5 no C2 . O1 . C17 . 110.2(2) yes C11 . O23 . C24 . 114.1(2) yes O1 . C2 . O18 . 120.0(3) yes O1 . C2 . C3 . 110.1(3) yes O18 . C2 . C3 . 129.9(4) yes C2 . C3 . C4 . 110.0(3) yes C2 . C3 . C16 . 103.2(3) yes C4 . C3 . C16 . 111.5(3) yes C2 . C3 . H31 . 110.6 no C4 . C3 . H31 . 110.6 no C16 . C3 . H31 . 110.6 no C3 . C4 . C5 . 110.5(3) yes C3 . C4 . H41 . 109.2 no C5 . C4 . H41 . 109.2 no C3 . C4 . H42 . 109.2 no C5 . C4 . H42 . 109.2 no H41 . C4 . H42 . 109.5 no C4 . C5 . C6 . 113.1(3) yes C4 . C5 . H51 . 108.6 no C6 . C5 . H51 . 108.6 no C4 . C5 . H52 . 108.6 no C6 . C5 . H52 . 108.6 no H51 . C5 . H52 . 109.5 no C5 . C6 . C7 . 110.7(2) yes C5 . C6 . C15 . 110.1(2) yes C7 . C6 . C15 . 110.9(2) yes C5 . C6 . C19 . 109.0(2) yes C7 . C6 . C19 . 106.4(2) yes C15 . C6 . C19 . 109.7(2) yes C6 . C7 . C8 . 121.6(3) yes C6 . C7 . C12 . 120.6(3) yes C8 . C7 . C12 . 117.7(3) yes C7 . C8 . C9 . 121.6(3) yes C7 . C8 . H81 . 119.2 no C9 . C8 . H81 . 119.2 no C8 . C9 . C10 . 122.1(3) yes C8 . C9 . H91 . 119.0 no C10 . C9 . H91 . 119.0 no C9 . C10 . C11 . 116.2(3) yes C9 . C10 . C20 . 121.1(3) yes C11 . C10 . C20 . 122.6(3) yes O23 . C11 . C10 . 119.0(3) yes O23 . C11 . C12 . 117.6(3) yes C10 . C11 . C12 . 123.3(3) yes C7 . C12 . C11 . 119.1(3) yes C7 . C12 . C13 . 120.3(3) yes C11 . C12 . C13 . 120.6(3) yes C12 . C13 . C14 . 113.3(3) yes C12 . C13 . H131 . 108.5 no C14 . C13 . H131 . 108.5 no C12 . C13 . H132 . 108.5 no C14 . C13 . H132 . 108.5 no H131 . C13 . H132 . 109.5 no C13 . C14 . C15 . 123.3(3) yes C13 . C14 . H141 . 118.4 no C15 . C14 . H141 . 118.4 no C6 . C15 . C14 . 121.6(3) yes C6 . C15 . C16 . 119.7(3) yes C14 . C15 . C16 . 118.6(3) yes C3 . C16 . C15 . 117.6(3) yes C3 . C16 . C17 . 101.1(2) yes C15 . C16 . C17 . 114.2(3) yes C3 . C16 . H161 . 107.8 no C15 . C16 . H161 . 107.8 no C17 . C16 . H161 . 107.8 no C16 . C17 . O1 . 104.8(3) yes C16 . C17 . H171 . 110.6 no O1 . C17 . H171 . 110.6 no C16 . C17 . H172 . 110.6 no O1 . C17 . H172 . 110.6 no H171 . C17 . H172 . 109.5 no C6 . C19 . H191 . 109.5 no C6 . C19 . H192 . 109.5 no H191 . C19 . H192 . 109.5 no C6 . C19 . H193 . 109.5 no H191 . C19 . H193 . 109.5 no H192 . C19 . H193 . 109.5 no C10 . C20 . C21 . 110.9(3) yes C10 . C20 . C22 . 111.4(3) yes C21 . C20 . C22 . 109.9(4) yes C10 . C20 . H201 . 108.2 no C21 . C20 . H201 . 108.2 no C22 . C20 . H201 . 108.2 no C20 . C21 . H211 . 109.5 no C20 . C21 . H212 . 109.5 no H211 . C21 . H212 . 109.5 no C20 . C21 . H213 . 109.5 no H211 . C21 . H213 . 109.5 no H212 . C21 . H213 . 109.5 no C20 . C22 . H221 . 109.5 no C20 . C22 . H222 . 109.5 no H221 . C22 . H222 . 109.5 no C20 . C22 . H223 . 109.5 no H221 . C22 . H223 . 109.5 no H222 . C22 . H223 . 109.5 no O23 . C24 . H241 . 109.5 no O23 . C24 . H242 . 109.5 no H241 . C24 . H242 . 109.5 no O23 . C24 . H243 . 109.5 no H241 . C24 . H243 . 109.5 no H242 . C24 . H243 . 109.5 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C103 3.301(4) . 2_656 no O1 C104 3.385(4) . 4_454 no O1 O118 3.471(3) . 4_454 no O1 C102 3.477(4) . 4_454 no O18 O101 3.272(3) . 4_454 no O18 C117 3.324(5) . 4_454 no O18 C19 3.549(4) . 3_645 no O18 C5 3.570(4) . 3_645 no O23 C24 3.379(4) . 2_756 no O23 O23 3.599(4) . 2_756 no O101 C4 3.319(4) . 4_655 no O101 C3 3.364(4) . 2_756 no O101 C2 3.379(4) . 4_655 no O101 C16 3.525(4) . 2_756 no C9 C119 3.475(4) . 2_766 no C19 C109 3.545(4) . 2_666 no C124 C124 3.569(8) . 2_656 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C2 C3 C4 . . . . -98.9(3) no O1 C2 C3 C16 . . . . 20.2(3) no O1 C17 C16 C3 . . . . 30.8(3) no O1 C17 C16 C15 . . . . 158.1(3) no O18 C2 O1 C17 . . . . -178.2(3) no O18 C2 C3 C4 . . . . 78.9(4) no O18 C2 C3 C16 . . . . -162.0(3) no O23 C11 C10 C9 . . . . 176.0(3) no O23 C11 C10 C20 . . . . -3.9(5) no O23 C11 C12 C7 . . . . -177.7(3) no O23 C11 C12 C13 . . . . 0.6(4) no O101 C102 C103 C104 . . . . -102.0(3) no O101 C102 C103 C116 . . . . 17.1(3) no O101 C117 C116 C103 . . . . 30.6(3) no O101 C117 C116 C115 . . . . 157.6(3) no O118 C102 O101 C117 . . . . -176.7(3) no O118 C102 C103 C104 . . . . 77.1(4) no O118 C102 C103 C116 . . . . -163.7(3) no O123 C111 C110 C109 . . . . -177.7(3) no O123 C111 C110 C120 . . . . -2.8(5) no O123 C111 C112 C107 . . . . 175.0(3) no O123 C111 C112 C113 . . . . -3.0(5) no C2 O1 C17 C16 . . . . -20.0(4) no C2 C3 C4 C5 . . . . 168.0(3) no C2 C3 C16 C15 . . . . -155.3(3) no C2 C3 C16 C17 . . . . -30.2(3) no C3 C2 O1 C17 . . . . -0.1(4) no C3 C4 C5 C6 . . . . -63.5(3) no C3 C16 C15 C6 . . . . 28.3(4) no C3 C16 C15 C14 . . . . -153.6(3) no C4 C3 C16 C15 . . . . -37.3(4) no C4 C3 C16 C17 . . . . 87.8(3) no C4 C5 C6 C7 . . . . 174.0(3) no C4 C5 C6 C15 . . . . 51.0(3) no C4 C5 C6 C19 . . . . -69.4(3) no C5 C4 C3 C16 . . . . 54.2(3) no C5 C6 C7 C8 . . . . 32.7(4) no C5 C6 C7 C12 . . . . -151.2(3) no C5 C6 C15 C14 . . . . 148.6(3) no C5 C6 C15 C16 . . . . -33.4(4) no C6 C7 C8 C9 . . . . 176.6(3) no C6 C7 C12 C11 . . . . -174.9(3) no C6 C7 C12 C13 . . . . 6.8(5) no C6 C15 C14 C13 . . . . -0.2(5) no C6 C15 C16 C17 . . . . -90.0(4) no C7 C6 C15 C14 . . . . 25.7(4) no C7 C6 C15 C16 . . . . -156.3(3) no C7 C8 C9 C10 . . . . -2.1(5) no C7 C12 C11 C10 . . . . -1.6(5) no C7 C12 C13 C14 . . . . 19.2(4) no C8 C7 C6 C15 . . . . 155.2(3) no C8 C7 C6 C19 . . . . -85.5(3) no C8 C7 C12 C11 . . . . 1.3(5) no C8 C7 C12 C13 . . . . -177.0(3) no C8 C9 C10 C11 . . . . 1.9(5) no C8 C9 C10 C20 . . . . -178.2(3) no C9 C8 C7 C12 . . . . 0.4(5) no C9 C10 C11 C12 . . . . -0.0(5) no C9 C10 C20 C21 . . . . 64.6(4) no C9 C10 C20 C22 . . . . -58.0(4) no C10 C11 O23 C24 . . . . 93.2(4) no C10 C11 C12 C13 . . . . 176.7(3) no C11 C10 C20 C21 . . . . -115.5(4) no C11 C10 C20 C22 . . . . 121.9(4) no C11 C12 C13 C14 . . . . -159.1(3) no C12 C7 C6 C15 . . . . -28.7(4) no C12 C7 C6 C19 . . . . 90.6(3) no C12 C11 O23 C24 . . . . -90.5(4) no C12 C11 C10 C20 . . . . -179.9(3) no C12 C13 C14 C15 . . . . -23.2(4) no C13 C14 C15 C16 . . . . -178.2(3) no C14 C15 C6 C19 . . . . -91.5(3) no C14 C15 C16 C17 . . . . 88.1(4) no C16 C15 C6 C19 . . . . 86.6(3) no C102 O101 C117 C116 . . . . -21.4(4) no C102 C103 C104 C105 . . . . 166.0(3) no C102 C103 C116 C115 . . . . -152.6(3) no C102 C103 C116 C117 . . . . -27.9(3) no C103 C102 O101 C117 . . . . 2.5(4) no C103 C104 C105 C106 . . . . -62.2(3) no C103 C116 C115 C106 . . . . 26.3(4) no C103 C116 C115 C114 . . . . -158.5(3) no C104 C103 C116 C115 . . . . -35.1(4) no C104 C103 C116 C117 . . . . 89.6(3) no C104 C105 C106 C107 . . . . 174.2(3) no C104 C105 C106 C115 . . . . 50.0(3) no C104 C105 C106 C119 . . . . -70.6(3) no C105 C104 C103 C116 . . . . 52.9(3) no C105 C106 C107 C108 . . . . 30.3(4) no C105 C106 C107 C112 . . . . -154.9(3) no C105 C106 C115 C114 . . . . 152.3(3) no C105 C106 C115 C116 . . . . -32.6(4) no C106 C107 C108 C109 . . . . 172.9(3) no C106 C107 C112 C111 . . . . -172.2(3) no C106 C107 C112 C113 . . . . 5.8(5) no C106 C115 C114 C113 . . . . 0.1(5) no C106 C115 C116 C117 . . . . -91.9(4) no C107 C106 C115 C114 . . . . 28.0(4) no C107 C106 C115 C116 . . . . -156.9(3) no C107 C108 C109 C110 . . . . -0.8(5) no C107 C112 C111 C110 . . . . -0.9(5) no C107 C112 C113 C114 . . . . 22.3(5) no C108 C107 C106 C115 . . . . 154.4(3) no C108 C107 C106 C119 . . . . -86.6(3) no C108 C107 C112 C111 . . . . 2.8(5) no C108 C107 C112 C113 . . . . -179.1(3) no C108 C109 C110 C111 . . . . 2.8(5) no C108 C109 C110 C120 . . . . -172.3(3) no C109 C108 C107 C112 . . . . -2.1(5) no C109 C110 C111 C112 . . . . -1.9(5) no C109 C110 C120 C121 . . . . 80.4(4) no C109 C110 C120 C122 . . . . -46.3(5) no C110 C111 O123 C124 . . . . -87.6(4) no C110 C111 C112 C113 . . . . -178.9(3) no C111 C110 C120 C121 . . . . -94.3(4) no C111 C110 C120 C122 . . . . 138.9(4) no C111 C112 C113 C114 . . . . -159.7(3) no C112 C107 C106 C115 . . . . -30.8(4) no C112 C107 C106 C119 . . . . 88.2(3) no C112 C111 O123 C124 . . . . 96.4(3) no C112 C111 C110 C120 . . . . 173.0(3) no C112 C113 C114 C115 . . . . -26.3(5) no C113 C114 C115 C116 . . . . -175.1(3) no C114 C115 C106 C119 . . . . -88.3(3) no C114 C115 C116 C117 . . . . 83.3(4) no C116 C115 C106 C119 . . . . 86.8(3) no #------------------------------------------------------------------------------ #===END data_she0617a _database_code_depnum_ccdc_archive 'CCDC 658576' _audit_creation_date 06-09-05 _audit_creation_method CRYSTALS_ver_12.18 _audit_update_record ; 2006-09-05 - Report on C20 H24 O3 by Anthony C. Willis for Natalie Miller and Mick Sherburn 2006-09-06 - passes checkcif tests with minor warnings 2007-08-27 # Formatted by publCIF ; _oxford_structure_analysis_title '9041512 she0617a' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 22.0658(4) _cell_length_b 6.9171(1) _cell_length_c 24.1734(4) _cell_angle_alpha 90 _cell_angle_beta 115.5026(8) _cell_angle_gamma 90 _cell_volume 3330.12(10) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1 ' _symmetry_space_group_name_Hall ? 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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C20 H24 O3 # Dc = 1.25 Fooo = 1344.00 Mu = 0.82 M = 624.82 # Found Formula = C20 H24 O3 # Dc = 1.25 FOOO = 1344.00 Mu = 0.82 M = 624.82 _chemical_formula_sum 'C20 H24 O3' _chemical_formula_moiety 'C20 H24 O3' _chemical_compound_source local _chemical_formula_weight 312.41 _cell_measurement_reflns_used 44279 _cell_measurement_theta_min 3 _cell_measurement_theta_max 25 _cell_measurement_temperature 200 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.082 # Sheldrick geometric approximatio 0.99 1.00 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.010 -1 0 0 0.050 0 1 0 0.200 0 -1 0 0.200 0 0 1 0.001 0 0 -1 0.050 1 0 -1 0.030 -1 0 1 0.040 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 1.3 deg at rate 520 sec/frame, crystal-detector distance 35mm, multiple scan sets so over 95 percent of data collected with 4-fold redundancy or more. ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_cell_refinement 'Denzo/Scalepack ' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Watkin et al 2003)' _computing_publication_material 'CRYSTALS ' _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 54540 _reflns_number_total 5856 _diffrn_reflns_av_R_equivalents 0.076 # Number of reflections with Friedels Law is 5856 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5860 _diffrn_reflns_theta_min 2.588 _diffrn_reflns_theta_max 24.992 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.992 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min -26 _reflns_limit_h_max 23 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _oxford_diffrn_Wilson_B_factor 3.28 _oxford_diffrn_Wilson_scale 7.84 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.25 _refine_diff_density_max 0.18 _refine_ls_number_reflns 3109 _refine_ls_number_restraints 142 _refine_ls_number_parameters 507 #_refine_ls_R_factor_ref 0.0410 _refine_ls_wR_factor_ref 0.0356 _refine_ls_goodness_of_fit_ref 1.1332 #_reflns_number_all 5833 _refine_ls_R_factor_all 0.0948 _refine_ls_wR_factor_all 0.0401 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3109 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_gt 0.0356 _refine_ls_shift/su_max 0.010079 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.30 -1.11 1.44 -0.536 0.473 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.19255(7) 0.8589(2) 0.45315(7) 0.0494 1.0000 Uani . . . . . . O19 O 0.15071(8) 0.5767(3) 0.41065(7) 0.0612 1.0000 Uani . . . . . . O23 O 0.29772(8) 1.3209(2) 0.73698(7) 0.0585 1.0000 Uani . . . . . . O123 O 0.38151(9) 1.0810(3) 0.96762(8) 0.0697 1.0000 Uani . . . . . . O1011 O 0.4963(4) 0.9823(9) 0.7028(3) 0.0655 0.628(5) Uani D U P . . . O1012 O 0.4826(5) 1.0675(13) 0.7109(5) 0.0595 0.372(5) Uani D U P . . . O1191 O 0.49466(18) 0.7379(6) 0.64178(16) 0.0768 0.628(5) Uani D U P . . . O1192 O 0.5202(3) 0.8897(12) 0.6558(3) 0.0777 0.372(5) Uani D U P . . . C2 C 0.14396(10) 0.7241(4) 0.43389(9) 0.0446 1.0000 Uani . . . . . . C3 C 0.08625(10) 0.7833(3) 0.44675(9) 0.0415 1.0000 Uani . . . . . . C4 C 0.06365(11) 0.6284(3) 0.47951(10) 0.0476 1.0000 Uani . . . . . . C5 C 0.06453(10) 0.7306(3) 0.53580(9) 0.0401 1.0000 Uani . . . . . . C6 C 0.11998(9) 0.8864(3) 0.55394(8) 0.0325 1.0000 Uani . . . . . . C7 C 0.11093(9) 1.0469(3) 0.59451(9) 0.0371 1.0000 Uani . . . . . . C8 C 0.14057(9) 0.9489(3) 0.65870(9) 0.0367 1.0000 Uani . . . . . . C9 C 0.14777(10) 1.0738(3) 0.71202(9) 0.0435 1.0000 Uani . . . . . . C10 C 0.19815(10) 1.1990(3) 0.73959(9) 0.0424 1.0000 Uani . . . . . . C11 C 0.24703(10) 1.2220(3) 0.71275(9) 0.0420 1.0000 Uani . . . . . . C12 C 0.22899(10) 1.1203(3) 0.65270(9) 0.0383 1.0000 Uani . . . . . . C13 C 0.20828(9) 0.9094(3) 0.65764(9) 0.0358 1.0000 Uani . . . . . . C14 C 0.18883(9) 0.8053(3) 0.59769(8) 0.0319 1.0000 Uani . . . . . . C15 C 0.22350(10) 0.6633(3) 0.58880(10) 0.0416 1.0000 Uani . . . . . . C16 C 0.16168(10) 1.2083(3) 0.60397(9) 0.0409 1.0000 Uani . . . . . . C17 C 0.11260(10) 0.9572(3) 0.49027(9) 0.0386 1.0000 Uani . . . . . . C18 C 0.17623(11) 1.0175(3) 0.48387(10) 0.0447 1.0000 Uani . . . . . . C20 C 0.20846(12) 1.3207(3) 0.79456(10) 0.0527 1.0000 Uani . . . . . . C21 C 0.18790(14) 1.5304(3) 0.77558(12) 0.0642 1.0000 Uani . . . . . . C22 C 0.17248(17) 1.2424(4) 0.83103(13) 0.0808 1.0000 Uani . . . . . . C106 C 0.44059(10) 0.7415(3) 0.79573(9) 0.0429 1.0000 Uani D U . . . . C107 C 0.38511(10) 0.7065(3) 0.81794(9) 0.0409 1.0000 Uani . . . . . . C108 C 0.42659(11) 0.6280(3) 0.88411(9) 0.0448 1.0000 Uani . . . . . . C109 C 0.39014(11) 0.5989(3) 0.92338(10) 0.0520 1.0000 Uani . . . . . . C110 C 0.37538(11) 0.7411(3) 0.95293(10) 0.0488 1.0000 Uani D . . . . . C111 C 0.39207(11) 0.9398(3) 0.94209(10) 0.0506 1.0000 Uani . . . . . . C112 C 0.41881(11) 0.9603(3) 0.89497(10) 0.0480 1.0000 Uani . . . . . . C113 C 0.47269(10) 0.8054(3) 0.90398(9) 0.0463 1.0000 Uani . . . . . . C114 C 0.49665(10) 0.8219(3) 0.85433(10) 0.0450 1.0000 Uani . . . . . . C115 C 0.55692(12) 0.8818(4) 0.86316(11) 0.0612 1.0000 Uani . . . . . . C116 C 0.36191(10) 0.9023(3) 0.83133(9) 0.0459 1.0000 Uani . . . . . . C120 C 0.34214(12) 0.7111(4) 0.99532(11) 0.0586 1.0000 Uani D U . . . . C1021 C 0.4706(4) 0.8146(9) 0.6727(4) 0.0516 0.628(5) Uani D U P . . . C1022 C 0.4855(6) 0.9008(16) 0.6832(6) 0.0510 0.372(5) Uani D U P . . . C1031 C 0.4134(2) 0.7503(7) 0.6846(2) 0.0398 0.628(5) Uani D U P . . . C1032 C 0.4457(5) 0.7435(14) 0.6956(4) 0.0486 0.372(5) Uani D U P . . . C1041 C 0.42129(18) 0.5410(5) 0.70762(15) 0.0455 0.628(5) Uani D U P . . . C1042 C 0.4897(3) 0.5802(8) 0.7343(3) 0.0511 0.372(5) Uani D U P . . . C1051 C 0.4663(6) 0.5604(13) 0.7751(5) 0.0482 0.628(5) Uani D U P . . . C1052 C 0.4587(11) 0.535(2) 0.7785(9) 0.0491 0.372(5) Uani D U P . . . C1171 C 0.4156(5) 0.8765(13) 0.7366(4) 0.0447 0.628(5) Uani D U P . . . C1172 C 0.4138(8) 0.846(2) 0.7336(6) 0.0377 0.372(5) Uani D U P . . . C1181 C 0.4561(5) 1.0486(13) 0.7333(5) 0.0595 0.628(5) Uani D U P . . . C1182 C 0.4333(9) 1.057(2) 0.7359(10) 0.0520 0.372(5) Uani D U P . . . C1211 C 0.3706(11) 0.537(3) 1.0369(9) 0.1200 0.54(3) Uani D U P . . . C1212 C 0.3901(11) 0.614(3) 1.0531(7) 0.1091 0.46(3) Uani D U P . . . C1221 C 0.2676(6) 0.702(3) 0.9594(7) 0.0980 0.54(3) Uani D U P . . . C1222 C 0.2761(9) 0.608(4) 0.9656(9) 0.1165 0.46(3) Uani D U P . . . H31 H 0.04749 0.8236 0.40790 0.0492 1.0000 Uiso R . . . . . H41 H 0.01740 0.5817 0.45235 0.0585 1.0000 Uiso R . . . . . H42 H 0.09545 0.5165 0.49194 0.0585 1.0000 Uiso R . . . . . H51 H 0.02001 0.7922 0.52573 0.0492 1.0000 Uiso R . . . . . H52 H 0.07506 0.6363 0.57009 0.0492 1.0000 Uiso R . . . . . H71 H 0.06361 1.0927 0.58028 0.0448 1.0000 Uiso R . . . . . H81 H 0.11652 0.8258 0.65805 0.0450 1.0000 Uiso R . . . . . H91 H 0.11286 1.0627 0.72786 0.0537 1.0000 Uiso R . . . . . H121 H 0.26590 1.1271 0.63923 0.0475 1.0000 Uiso R . . . . . H131 H 0.24097 0.8375 0.69422 0.0419 1.0000 Uiso R . . . . . H151 H 0.20511 0.5925 0.54885 0.0496 1.0000 Uiso R . . . . . H152 H 0.26818 0.6264 0.62201 0.0496 1.0000 Uiso R . . . . . H161 H 0.16504 1.2386 0.56493 0.0506 1.0000 Uiso R . . . . . H162 H 0.14933 1.3281 0.61991 0.0506 1.0000 Uiso R . . . . . H171 H 0.07899 1.0645 0.47550 0.0462 1.0000 Uiso R . . . . . H181 H 0.16770 1.1382 0.45888 0.0569 1.0000 Uiso R . . . . . H182 H 0.21396 1.0399 0.52522 0.0569 1.0000 Uiso R . . . . . H201 H 0.25763 1.3205 0.82227 0.0637 1.0000 Uiso R . . . . . H211 H 0.19510 1.6088 0.81265 0.0781 1.0000 Uiso R . . . . . H212 H 0.13940 1.5351 0.74590 0.0781 1.0000 Uiso R . . . . . H213 H 0.21577 1.5843 0.75578 0.0781 1.0000 Uiso R . . . . . H221 H 0.18123 1.3291 0.86678 0.1053 1.0000 Uiso R . . . . . H222 H 0.12312 1.2370 0.80423 0.1053 1.0000 Uiso R . . . . . H223 H 0.18940 1.1095 0.84612 0.1053 1.0000 Uiso R . . . . . H1031 H 0.3700 0.7676 0.6474 0.0474 0.6281 Uiso R . . . . . H1032 H 0.4101 0.6924 0.6563 0.0594 0.3719 Uiso R . . . . . H1041 H 0.44272 0.4590 0.68691 0.0567 0.6281 Uiso R . . . . . H1042 H 0.37690 0.4842 0.70067 0.0567 0.6281 Uiso R . . . . . H1043 H 0.4876 0.4654 0.7084 0.0633 0.3719 Uiso R . . . . . H1044 H 0.5374 0.6231 0.7569 0.0633 0.3719 Uiso R . . . . . H1051 H 0.5141 0.5784 0.7822 0.0591 0.6281 Uiso R . . . . . H1052 H 0.4628 0.4434 0.7979 0.0591 0.6281 Uiso R . . . . . H1053 H 0.4175 0.454 0.7582 0.0626 0.3719 Uiso R . . . . . H1054 H 0.4917 0.467 0.8158 0.0626 0.3719 Uiso R . . . . . H1071 H 0.34793 0.6195 0.79092 0.0479 1.0000 Uiso R . . . . . H1081 H 0.45222 0.5094 0.88359 0.0552 1.0000 Uiso R . . . . . H1091 H 0.37598 0.4646 0.92774 0.0630 1.0000 Uiso R . . . . . H1121 H 0.43586 1.0939 0.89441 0.0564 1.0000 Uiso R . . . . . H1131 H 0.50943 0.7978 0.94653 0.0529 1.0000 Uiso R . . . . . H1151 H 0.57058 0.8775 0.82874 0.0719 1.0000 Uiso R . . . . . H1152 H 0.58892 0.9315 0.90427 0.0719 1.0000 Uiso R . . . . . H1161 H 0.35780 0.9994 0.79925 0.0549 1.0000 Uiso R . . . . . H1162 H 0.31785 0.8900 0.83354 0.0549 1.0000 Uiso R . . . . . H1171 H 0.3690 0.9209 0.7268 0.0517 0.6281 Uiso R . . . . . H1172 H 0.3638 0.833 0.7123 0.0464 0.3719 Uiso R . . . . . H1181 H 0.4255 1.1553 0.7093 0.0691 0.6281 Uiso R . . . . . H1182 H 0.4858 1.0958 0.7755 0.0691 0.6281 Uiso R . . . . . H1183 H 0.3930 1.137 0.7106 0.0650 0.3719 Uiso R . . . . . H1184 H 0.4533 1.105 0.7791 0.0650 0.3719 Uiso R . . . . . H1201 H 0.35236 0.8276 1.02233 0.0724 0.5400 Uiso R . . . . . H1202 H 0.33265 0.8423 1.00709 0.0724 0.4600 Uiso R . . . . . H1211 H 0.3473 0.522 1.0642 0.1640 0.5403 Uiso R . . . . . H1212 H 0.3634 0.418 1.0113 0.1640 0.5403 Uiso R . . . . . H1213 H 0.4197 0.556 1.0625 0.1640 0.5403 Uiso R . . . . . H1214 H 0.3678 0.594 1.0810 0.1391 0.4597 Uiso R . . . . . H1215 H 0.4037 0.486 1.0429 0.1391 0.4597 Uiso R . . . . . H1216 H 0.4308 0.697 1.0740 0.1391 0.4597 Uiso R . . . . . H1221 H 0.2462 0.683 0.9880 0.1237 0.5403 Uiso R . . . . . H1222 H 0.2555 0.593 0.9297 0.1237 0.5403 Uiso R . . . . . H1223 H 0.2511 0.826 0.9365 0.1237 0.5403 Uiso R . . . . . H1224 H 0.2567 0.593 0.9959 0.1492 0.4597 Uiso R . . . . . H1225 H 0.2445 0.685 0.9297 0.1492 0.4597 Uiso R . . . . . H1226 H 0.2832 0.478 0.9514 0.1492 0.4597 Uiso 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 0.0448(8) 0.0580(10) 0.0536(9) -0.0046(8) 0.0288(7) -0.0098(8) O19 0.0555(10) 0.0736(12) 0.0636(10) -0.0220(9) 0.0343(8) -0.0086(9) O23 0.0537(9) 0.0554(10) 0.0651(10) -0.0161(8) 0.0244(8) -0.0188(9) O123 0.0934(13) 0.0574(11) 0.0625(11) -0.0210(9) 0.0375(10) -0.0014(10) O1011 0.064(3) 0.062(5) 0.067(4) 0.002(4) 0.025(3) -0.023(3) O1012 0.056(4) 0.063(6) 0.061(4) 0.000(5) 0.027(3) -0.004(4) O1191 0.076(2) 0.083(3) 0.096(2) 0.013(2) 0.060(2) 0.014(2) O1192 0.065(3) 0.108(5) 0.081(4) 0.034(4) 0.051(3) 0.032(4) C2 0.0387(11) 0.0600(15) 0.0361(11) -0.0023(11) 0.0170(9) -0.0037(11) C3 0.0326(10) 0.0548(13) 0.0356(11) 0.0006(10) 0.0133(9) -0.0022(10) C4 0.0420(12) 0.0535(14) 0.0508(13) -0.0087(11) 0.0233(10) -0.0137(11) C5 0.0323(10) 0.0463(13) 0.0444(11) 0.0001(10) 0.0190(9) -0.0054(10) C6 0.0264(9) 0.0353(11) 0.0369(10) 0.0019(9) 0.0146(8) -0.0004(8) C7 0.0314(10) 0.0412(12) 0.0394(11) 0.0034(9) 0.0160(8) 0.0069(9) C8 0.0346(10) 0.0363(11) 0.0415(11) -0.0005(9) 0.0185(9) -0.0057(9) C9 0.0411(11) 0.0507(13) 0.0425(12) 0.0030(11) 0.0217(9) 0.0005(11) C10 0.0465(12) 0.0408(12) 0.0397(11) 0.0003(10) 0.0186(10) -0.0002(10) C11 0.0410(11) 0.0351(11) 0.0467(12) 0.0015(10) 0.0159(10) -0.0024(10) C12 0.0365(11) 0.0352(11) 0.0471(12) -0.0021(10) 0.0216(9) -0.0077(9) C13 0.0324(10) 0.0328(11) 0.0396(11) 0.0069(9) 0.0130(8) 0.0014(9) C14 0.0295(9) 0.0305(10) 0.0398(11) 0.0051(9) 0.0188(8) -0.0027(9) C15 0.0342(11) 0.0382(12) 0.0516(12) 0.0009(10) 0.0178(10) 0.0007(10) C16 0.0510(12) 0.0341(11) 0.0416(11) 0.0016(9) 0.0237(10) 0.0031(10) C17 0.0363(11) 0.0410(12) 0.0382(11) 0.0046(9) 0.0158(9) 0.0039(9) C18 0.0505(12) 0.0448(13) 0.0469(12) 0.0042(10) 0.0287(10) -0.0051(10) C20 0.0629(14) 0.0534(15) 0.0429(13) -0.0046(11) 0.0239(11) -0.0023(12) C21 0.0787(18) 0.0502(15) 0.0663(16) -0.0067(13) 0.0338(14) 0.0019(13) C22 0.130(3) 0.0707(19) 0.0630(16) -0.0170(15) 0.0614(18) -0.0186(18) C106 0.0428(11) 0.0419(12) 0.0407(11) -0.0019(9) 0.0150(9) 0.0040(10) C107 0.0399(11) 0.0409(12) 0.0391(11) -0.0084(10) 0.0142(9) -0.0022(10) C108 0.0546(13) 0.0375(12) 0.0460(12) -0.0014(10) 0.0253(11) 0.0051(10) C109 0.0607(14) 0.0459(13) 0.0510(13) 0.0011(11) 0.0257(12) 0.0005(12) C110 0.0524(13) 0.0512(14) 0.0438(12) -0.0057(11) 0.0218(11) 0.0001(11) C111 0.0533(13) 0.0497(14) 0.0425(12) -0.0137(11) 0.0146(10) 0.0019(11) C112 0.0569(14) 0.0370(13) 0.0472(13) -0.0082(10) 0.0196(11) -0.0061(11) C113 0.0422(12) 0.0532(14) 0.0369(11) -0.0023(10) 0.0109(10) -0.0027(10) C114 0.0388(11) 0.0466(13) 0.0434(12) 0.0006(10) 0.0120(9) 0.0018(10) C115 0.0526(15) 0.0729(17) 0.0542(14) -0.0059(13) 0.0193(12) -0.0105(13) C116 0.0454(12) 0.0476(13) 0.0443(12) -0.0016(10) 0.0190(10) 0.0075(11) C120 0.0668(15) 0.0639(16) 0.0503(13) -0.0063(12) 0.0301(12) 0.0030(13) C1021 0.049(4) 0.047(4) 0.056(4) 0.006(3) 0.020(3) 0.007(3) C1022 0.048(8) 0.064(11) 0.041(7) 0.005(8) 0.020(7) 0.015(7) C1031 0.039(3) 0.037(2) 0.043(3) 0.0019(18) 0.017(2) 0.003(2) C1032 0.045(5) 0.062(5) 0.042(5) -0.008(3) 0.021(5) 0.006(5) C1041 0.057(2) 0.0344(19) 0.050(2) -0.0051(16) 0.0282(18) -0.0018(16) C1042 0.052(4) 0.040(3) 0.067(4) 0.002(3) 0.030(3) 0.005(3) C1051 0.059(5) 0.037(3) 0.052(3) 0.012(3) 0.027(3) 0.011(3) C1052 0.045(5) 0.053(7) 0.058(6) -0.015(5) 0.031(5) 0.006(5) C1171 0.045(5) 0.046(4) 0.038(3) -0.002(3) 0.013(3) 0.011(3) C1172 0.032(6) 0.040(6) 0.043(6) -0.003(4) 0.019(5) -0.009(4) C1181 0.087(8) 0.035(3) 0.051(4) -0.001(3) 0.025(4) -0.006(4) C1182 0.064(8) 0.041(5) 0.057(5) 0.000(4) 0.033(5) 0.006(5) C1211 0.173(12) 0.136(12) 0.099(9) 0.057(8) 0.105(9) 0.075(9) C1212 0.144(11) 0.138(14) 0.065(6) 0.032(8) 0.063(6) 0.073(9) C1221 0.079(4) 0.152(12) 0.079(5) -0.001(7) 0.049(4) 0.001(6) C1222 0.107(8) 0.171(15) 0.097(8) -0.040(10) 0.067(7) -0.064(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4193(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.344(3) yes O1 . C18 . 1.454(3) yes O19 . C2 . 1.204(3) yes O23 . C11 . 1.224(2) yes O123 . C111 . 1.230(3) yes O1011 . C1021 . 1.357(6) yes O1011 . C1181 . 1.450(8) yes O1012 . C1022 . 1.349(11) yes O1012 . C1182 . 1.455(11) yes O1191 . C1021 . 1.210(7) yes O1192 . C1022 . 1.212(10) yes C2 . C3 . 1.492(3) yes C3 . C4 . 1.537(3) yes C3 . C17 . 1.538(3) yes C3 . H31 . 1.000 no C4 . C5 . 1.526(3) yes C4 . H41 . 1.000 no C4 . H42 . 1.000 no C5 . C6 . 1.546(3) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C6 . C7 . 1.550(3) yes C6 . C14 . 1.535(3) yes C6 . C17 . 1.556(3) yes C7 . C8 . 1.556(3) yes C7 . C16 . 1.527(3) yes C7 . H71 . 1.000 no C8 . C9 . 1.502(3) yes C8 . C13 . 1.530(3) yes C8 . H81 . 1.000 no C9 . C10 . 1.339(3) yes C9 . H91 . 1.000 no C10 . C11 . 1.487(3) yes C10 . C20 . 1.505(3) yes C11 . C12 . 1.505(3) yes C12 . C13 . 1.549(3) yes C12 . C16 . 1.568(3) yes C12 . H121 . 1.000 no C13 . C14 . 1.505(3) yes C13 . H131 . 1.000 no C14 . C15 . 1.318(3) yes C15 . H151 . 1.000 no C15 . H152 . 1.000 no C16 . H161 . 1.000 no C16 . H162 . 1.000 no C17 . C18 . 1.535(3) yes C17 . H171 . 1.000 no C18 . H181 . 1.000 no C18 . H182 . 1.000 no C20 . C21 . 1.530(3) yes C20 . C22 . 1.518(3) yes C20 . H201 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no C22 . H221 . 1.000 no C22 . H222 . 1.000 no C22 . H223 . 1.000 no C106 . C107 . 1.553(3) yes C106 . C114 . 1.529(3) yes C106 . C1051 . 1.544(9) yes C106 . C1052 . 1.587(13) yes C106 . C1171 . 1.593(8) yes C106 . C1172 . 1.538(13) yes C107 . C108 . 1.559(3) yes C107 . C116 . 1.531(3) yes C107 . H1071 . 1.000 no C108 . C109 . 1.499(3) yes C108 . C113 . 1.533(3) yes C108 . H1081 . 1.000 no C109 . C110 . 1.336(3) yes C109 . H1091 . 1.000 no C110 . C111 . 1.475(3) yes C110 . C120 . 1.509(3) yes C111 . C112 . 1.498(3) yes C112 . C113 . 1.545(3) yes C112 . C116 . 1.562(3) yes C112 . H1121 . 1.000 no C113 . C114 . 1.510(3) yes C113 . H1131 . 1.000 no C114 . C115 . 1.320(3) yes C115 . H1151 . 1.000 no C115 . H1152 . 1.000 no C116 . H1161 . 1.000 no C116 . H1162 . 1.000 no C120 . C1211 . 1.522(13) yes C120 . C1212 . 1.501(13) yes C120 . C1221 . 1.495(11) yes C120 . C1222 . 1.498(13) yes C120 . H1201 . 1.000 no C120 . H1202 . 1.000 no C1021 . C1031 . 1.480(7) yes C1022 . C1032 . 1.508(12) yes C1031 . C1041 . 1.533(6) yes C1031 . H1031 . 1.000 no C1032 . C1042 . 1.521(10) yes C1032 . C1172 . 1.547(13) yes C1032 . H1032 . 1.000 no C1041 . C1051 . 1.508(11) yes C1041 . H1041 . 1.000 no C1041 . H1042 . 1.000 no C1042 . C1052 . 1.530(14) yes C1042 . H1043 . 1.000 no C1042 . H1044 . 1.000 no C1051 . H1051 . 1.000 no C1051 . H1052 . 1.000 no C1052 . H1053 . 1.000 no C1052 . H1054 . 1.000 no C1171 . C1181 . 1.511(10) yes C1171 . H1171 . 1.000 no C1172 . H1172 . 1.000 no C1181 . H1181 . 1.000 no C1181 . H1182 . 1.000 no C1182 . H1183 . 1.000 no C1182 . H1184 . 1.000 no C1211 . H1211 . 1.000 no C1211 . H1212 . 1.000 no C1211 . H1213 . 1.000 no C1212 . H1214 . 1.000 no C1212 . H1215 . 1.000 no C1212 . H1216 . 1.000 no C1221 . H1221 . 1.000 no C1221 . H1222 . 1.000 no C1221 . H1223 . 1.000 no C1222 . H1224 . 1.000 no C1222 . H1225 . 1.000 no C1222 . H1226 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C18 . 111.36(15) yes C1021 . O1011 . C1181 . 109.8(6) yes C1022 . O1012 . C1182 . 111.5(9) yes O1 . C2 . O19 . 120.58(19) yes O1 . C2 . C3 . 111.25(19) yes O19 . C2 . C3 . 128.2(2) yes C2 . C3 . C4 . 114.29(19) yes C2 . C3 . C17 . 104.59(17) yes C4 . C3 . C17 . 107.68(16) yes C2 . C3 . H31 . 110.0 no C4 . C3 . H31 . 110.0 no C17 . C3 . H31 . 110.0 no C3 . C4 . C5 . 104.74(17) yes C3 . C4 . H41 . 110.6 no C5 . C4 . H41 . 110.6 no C3 . C4 . H42 . 110.6 no C5 . C4 . H42 . 110.6 no H41 . C4 . H42 . 109.5 no C4 . C5 . C6 . 106.29(16) yes C4 . C5 . H51 . 110.3 no C6 . C5 . H51 . 110.3 no C4 . C5 . H52 . 110.3 no C6 . C5 . H52 . 110.3 no H51 . C5 . H52 . 109.5 no C5 . C6 . C7 . 112.15(15) yes C5 . C6 . C14 . 111.60(15) yes C7 . C6 . C14 . 100.64(14) yes C5 . C6 . C17 . 101.88(15) yes C7 . C6 . C17 . 114.44(16) yes C14 . C6 . C17 . 116.59(14) yes C6 . C7 . C8 . 101.89(15) yes C6 . C7 . C16 . 109.40(15) yes C8 . C7 . C16 . 101.70(15) yes C6 . C7 . H71 . 114.2 no C8 . C7 . H71 . 114.2 no C16 . C7 . H71 . 114.2 no C7 . C8 . C9 . 116.69(17) yes C7 . C8 . C13 . 93.17(15) yes C9 . C8 . C13 . 111.96(16) yes C7 . C8 . H81 . 111.3 no C9 . C8 . H81 . 111.3 no C13 . C8 . H81 . 111.3 no C8 . C9 . C10 . 123.88(18) yes C8 . C9 . H91 . 118.1 no C10 . C9 . H91 . 118.1 no C9 . C10 . C11 . 117.07(18) yes C9 . C10 . C20 . 125.36(19) yes C11 . C10 . C20 . 117.56(18) yes C10 . C11 . O23 . 122.42(19) yes C10 . C11 . C12 . 115.49(17) yes O23 . C11 . C12 . 122.06(19) yes C11 . C12 . C13 . 109.30(17) yes C11 . C12 . C16 . 108.35(16) yes C13 . C12 . C16 . 102.02(15) yes C11 . C12 . H121 . 112.2 no C13 . C12 . H121 . 112.2 no C16 . C12 . H121 . 112.2 no C12 . C13 . C8 . 98.95(15) yes C12 . C13 . C14 . 110.33(16) yes C8 . C13 . C14 . 103.05(15) yes C12 . C13 . H131 . 114.3 no C8 . C13 . H131 . 114.3 no C14 . C13 . H131 . 114.3 no C6 . C14 . C13 . 106.01(15) yes C6 . C14 . C15 . 129.15(18) yes C13 . C14 . C15 . 124.63(18) yes C14 . C15 . H151 . 120.0 no C14 . C15 . H152 . 120.0 no H151 . C15 . H152 . 120.0 no C7 . C16 . C12 . 103.00(15) yes C7 . C16 . H161 . 111.1 no C12 . C16 . H161 . 111.1 no C7 . C16 . H162 . 111.1 no C12 . C16 . H162 . 111.1 no H161 . C16 . H162 . 109.5 no C3 . C17 . C6 . 106.16(16) yes C3 . C17 . C18 . 103.67(16) yes C6 . C17 . C18 . 118.33(16) yes C3 . C17 . H171 . 109.4 no C6 . C17 . H171 . 109.4 no C18 . C17 . H171 . 109.4 no C17 . C18 . O1 . 106.56(16) yes C17 . C18 . H181 . 110.2 no O1 . C18 . H181 . 110.2 no C17 . C18 . H182 . 110.2 no O1 . C18 . H182 . 110.2 no H181 . C18 . H182 . 109.5 no C10 . C20 . C21 . 110.66(19) yes C10 . C20 . C22 . 113.3(2) yes C21 . C20 . C22 . 110.5(2) yes C10 . C20 . H201 . 107.4 no C21 . C20 . H201 . 107.4 no C22 . C20 . H201 . 107.4 no C20 . C21 . H211 . 109.5 no C20 . C21 . H212 . 109.5 no H211 . C21 . H212 . 109.5 no C20 . C21 . H213 . 109.5 no H211 . C21 . H213 . 109.5 no H212 . C21 . H213 . 109.5 no C20 . C22 . H221 . 109.5 no C20 . C22 . H222 . 109.5 no H221 . C22 . H222 . 109.5 no C20 . C22 . H223 . 109.5 no H221 . C22 . H223 . 109.5 no H222 . C22 . H223 . 109.5 no C107 . C106 . C114 . 100.39(16) yes C107 . C106 . C1051 . 116.1(5) yes C114 . C106 . C1051 . 109.3(5) yes C107 . C106 . C1052 . 106.0(7) yes C114 . C106 . C1052 . 112.1(8) yes C107 . C106 . C1171 . 112.4(4) yes C114 . C106 . C1171 . 116.6(4) yes C1051 . C106 . C1171 . 102.7(5) yes C114 . C106 . C1172 . 123.5(6) yes C1052 . C106 . C1172 . 101.6(8) yes C106 . C107 . C108 . 101.96(16) yes C106 . C107 . C116 . 108.67(17) yes C108 . C107 . C116 . 101.12(16) yes C106 . C107 . H1071 . 114.5 no C108 . C107 . H1071 . 114.5 no C116 . C107 . H1071 . 114.5 no C107 . C108 . C109 . 117.31(18) yes C107 . C108 . C113 . 93.46(16) yes C109 . C108 . C113 . 111.95(18) yes C107 . C108 . H1081 . 111.0 no C109 . C108 . H1081 . 111.0 no C113 . C108 . H1081 . 111.0 no C108 . C109 . C110 . 124.1(2) yes C108 . C109 . H1091 . 118.0 no C110 . C109 . H1091 . 118.0 no C109 . C110 . C111 . 117.0(2) yes C109 . C110 . C120 . 124.3(2) yes C111 . C110 . C120 . 118.7(2) yes C110 . C111 . O123 . 122.4(2) yes C110 . C111 . C112 . 115.69(19) yes O123 . C111 . C112 . 121.9(2) yes C111 . C112 . C113 . 110.98(18) yes C111 . C112 . C116 . 108.16(18) yes C113 . C112 . C116 . 101.78(16) yes C111 . C112 . H1121 . 111.8 no C113 . C112 . H1121 . 111.8 no C116 . C112 . H1121 . 111.8 no C112 . C113 . C108 . 98.30(16) yes C112 . C113 . C114 . 110.31(18) yes C108 . C113 . C114 . 102.92(17) yes C112 . C113 . H1131 . 114.5 no C108 . C113 . H1131 . 114.5 no C114 . C113 . H1131 . 114.5 no C106 . C114 . C113 . 106.77(17) yes C106 . C114 . C115 . 128.4(2) yes C113 . C114 . C115 . 124.7(2) yes C114 . C115 . H1151 . 120.0 no C114 . C115 . H1152 . 120.0 no H1151 . C115 . H1152 . 120.0 no C107 . C116 . C112 . 103.61(16) yes C107 . C116 . H1161 . 110.9 no C112 . C116 . H1161 . 110.9 no C107 . C116 . H1162 . 110.9 no C112 . C116 . H1162 . 110.9 no H1161 . C116 . H1162 . 109.5 no C110 . C120 . C1211 . 112.0(7) yes C110 . C120 . C1212 . 109.8(9) yes C110 . C120 . C1221 . 110.3(7) yes C1211 . C120 . C1221 . 112.9(8) yes C110 . C120 . C1222 . 113.3(8) yes C1212 . C120 . C1222 . 112.6(10) yes C110 . C120 . H1201 . 107.1 no C1211 . C120 . H1201 . 107.2 no C1221 . C120 . H1201 . 107.1 no C110 . C120 . H1202 . 106.9 no C1212 . C120 . H1202 . 107.0 no C1222 . C120 . H1202 . 106.8 no O1011 . C1021 . O1191 . 120.9(7) yes O1011 . C1021 . C1031 . 110.3(6) yes O1191 . C1021 . C1031 . 128.8(5) yes O1012 . C1022 . O1192 . 120.2(10) yes O1012 . C1022 . C1032 . 111.2(8) yes O1192 . C1022 . C1032 . 128.5(9) yes C1021 . C1031 . C1041 . 112.4(5) yes C1021 . C1031 . C1171 . 105.2(5) yes C1041 . C1031 . C1171 . 106.6(4) yes C1021 . C1031 . H1031 . 110.8 no C1041 . C1031 . H1031 . 110.8 no C1171 . C1031 . H1031 . 110.8 no C1022 . C1032 . C1042 . 112.6(8) yes C1022 . C1032 . C1172 . 103.9(8) yes C1042 . C1032 . C1172 . 108.0(7) yes C1022 . C1032 . H1032 . 110.7 no C1042 . C1032 . H1032 . 110.7 no C1172 . C1032 . H1032 . 110.7 no C1031 . C1041 . C1051 . 103.2(4) yes C1031 . C1041 . H1041 . 111.0 no C1051 . C1041 . H1041 . 111.0 no C1031 . C1041 . H1042 . 111.0 no C1051 . C1041 . H1042 . 111.0 no H1041 . C1041 . H1042 . 109.5 no C1032 . C1042 . C1052 . 102.9(8) yes C1032 . C1042 . H1043 . 111.1 no C1052 . C1042 . H1043 . 111.1 no C1032 . C1042 . H1044 . 111.1 no C1052 . C1042 . H1044 . 111.1 no H1043 . C1042 . H1044 . 109.5 no C106 . C1051 . C1041 . 105.0(6) yes C106 . C1051 . H1051 . 110.5 no C1041 . C1051 . H1051 . 110.6 no C106 . C1051 . H1052 . 110.6 no C1041 . C1051 . H1052 . 110.6 no H1051 . C1051 . H1052 . 109.5 no C1042 . C1052 . C106 . 103.7(9) yes C1042 . C1052 . H1053 . 110.9 no C106 . C1052 . H1053 . 110.9 no C1042 . C1052 . H1054 . 110.9 no C106 . C1052 . H1054 . 110.9 no H1053 . C1052 . H1054 . 109.5 no C1031 . C1171 . C106 . 106.4(6) yes C1031 . C1171 . C1181 . 102.7(6) yes C106 . C1171 . C1181 . 121.7(7) yes C1031 . C1171 . H1171 . 108.5 no C106 . C1171 . H1171 . 108.5 no C1181 . C1171 . H1171 . 108.5 no C106 . C1172 . C1032 . 106.5(9) yes C106 . C1172 . C1182 . 115.6(11) yes C1032 . C1172 . C1182 . 105.6(9) yes C106 . C1172 . H1172 . 109.7 no C1032 . C1172 . H1172 . 109.7 no C1182 . C1172 . H1172 . 109.6 no C1171 . C1181 . O1011 . 106.4(6) yes C1171 . C1181 . H1181 . 110.2 no O1011 . C1181 . H1181 . 110.2 no C1171 . C1181 . H1182 . 110.2 no O1011 . C1181 . H1182 . 110.2 no H1181 . C1181 . H1182 . 109.5 no C1172 . C1182 . O1012 . 106.5(10) yes C1172 . C1182 . H1183 . 110.2 no O1012 . C1182 . H1183 . 110.2 no C1172 . C1182 . H1184 . 110.2 no O1012 . C1182 . H1184 . 110.2 no H1183 . C1182 . H1184 . 109.5 no C120 . C1211 . H1211 . 109.5 no C120 . C1211 . H1212 . 109.6 no H1211 . C1211 . H1212 . 109.5 no C120 . C1211 . H1213 . 109.3 no H1211 . C1211 . H1213 . 109.5 no H1212 . C1211 . H1213 . 109.5 no C120 . C1212 . H1214 . 109.4 no C120 . C1212 . H1215 . 109.5 no H1214 . C1212 . H1215 . 109.5 no C120 . C1212 . H1216 . 109.4 no H1214 . C1212 . H1216 . 109.5 no H1215 . C1212 . H1216 . 109.5 no C120 . C1221 . H1221 . 109.4 no C120 . C1221 . H1222 . 109.5 no H1221 . C1221 . H1222 . 109.5 no C120 . C1221 . H1223 . 109.5 no H1221 . C1221 . H1223 . 109.5 no H1222 . C1221 . H1223 . 109.5 no C120 . C1222 . H1224 . 109.5 no C120 . C1222 . H1225 . 109.5 no H1224 . C1222 . H1225 . 109.5 no C120 . C1222 . H1226 . 109.3 no H1224 . C1222 . H1226 . 109.5 no H1225 . C1222 . H1226 . 109.5 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C15 3.242(3) . 3_556 no O1 C18 3.533(2) . 3_546 no O19 C1031 3.098(5) . 3_546 no O19 C1022 3.13(1) . 3_546 no O19 O1012 3.138(9) . 3_546 no O19 C1021 3.141(7) . 3_546 no O19 C1182 3.22(2) . 3_546 no O19 C1181 3.26(1) . 3_546 no O19 O1011 3.288(7) . 3_546 no O19 C1032 3.425(9) . 3_546 no O19 C1171 3.499(9) . 3_546 no O19 C1172 3.53(1) . 3_546 no O19 C18 3.587(2) . 3_546 no O23 C107 3.378(2) . 1_565 no O23 C1041 3.453(5) . 1_565 no O23 C1182 3.51(2) . . no O23 C1052 3.57(2) . 1_565 no O23 C116 3.579(2) . . no O123 C113 3.464(2) . 2_677 no O1012 C1041 3.53(1) . 1_565 no O1012 C2 3.579(9) . 3_556 no O1012 C1042 3.58(1) . 1_565 no O1191 C8 3.327(5) . 4_565 no O1191 C5 3.520(5) . 4_565 no O1192 C4 3.411(7) . 3_556 no O1192 C8 3.519(8) . 4_565 no O1192 C5 3.537(9) . 4_565 no C15 C16 3.512(3) . 1_545 no C15 C18 3.514(4) . 3_546 no C1041 C1182 3.40(1) . 1_545 no C1041 C1181 3.49(1) . 1_545 no C1051 C1182 3.60(2) . 1_545 no C1052 C1182 3.44(2) . 1_545 no C1052 C1181 3.53(2) . 1_545 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C2 C3 C4 . . . . -129.8(2) no O1 C2 C3 C17 . . . . -12.3(2) no O1 C18 C17 C3 . . . . -14.2(2) no O1 C18 C17 C6 . . . . 103.0(2) no O19 C2 O1 C18 . . . . -175.6(2) no O19 C2 C3 C4 . . . . 48.9(3) no O19 C2 C3 C17 . . . . 166.4(2) no O23 C11 C10 C9 . . . . -174.2(2) no O23 C11 C10 C20 . . . . 7.0(3) no O23 C11 C12 C13 . . . . 133.8(2) no O23 C11 C12 C16 . . . . -115.8(2) no O123 C111 C110 C109 . . . . -178.9(2) no O123 C111 C110 C120 . . . . 2.0(3) no O123 C111 C112 C113 . . . . 138.2(2) no O123 C111 C112 C116 . . . . -110.9(2) no O1011 C1021 C1031 C1041 . . . . -127.2(5) no O1011 C1021 C1031 C1171 . . . . -11.6(7) no O1011 C1181 C1171 C106 . . . . 95(1) no O1011 C1181 C1171 C1031 . . . . -23.5(8) no O1012 C1022 C1032 C1042 . . . . -114(1) no O1012 C1022 C1032 C1172 . . . . 3(1) no O1012 C1182 C1172 C106 . . . . 108(2) no O1012 C1182 C1172 C1032 . . . . -10(1) no O1191 C1021 O1011 C1181 . . . . 176.7(7) no O1191 C1021 C1031 C1041 . . . . 52.3(8) no O1191 C1021 C1031 C1171 . . . . 167.9(7) no O1192 C1022 O1012 C1182 . . . . 174(1) no O1192 C1022 C1032 C1172 . . . . 179(1) no C2 O1 C18 C17 . . . . 7.4(2) no C2 C3 C4 C5 . . . . 126.5(2) no C2 C3 C17 C6 . . . . -109.8(2) no C2 C3 C17 C18 . . . . 15.6(2) no C3 C2 O1 C18 . . . . 3.2(2) no C3 C4 C5 C6 . . . . -30.0(2) no C3 C17 C6 C5 . . . . -29.7(2) no C3 C17 C6 C7 . . . . -150.9(2) no C3 C17 C6 C14 . . . . 92.1(2) no C4 C3 C17 C6 . . . . 12.2(2) no C4 C3 C17 C18 . . . . 137.5(2) no C4 C5 C6 C7 . . . . 159.8(1) no C4 C5 C6 C14 . . . . -88.1(2) no C4 C5 C6 C17 . . . . 37.0(2) no C5 C4 C3 C17 . . . . 10.8(2) no C5 C6 C7 C8 . . . . 80.0(2) no C5 C6 C7 C16 . . . . -172.9(1) no C5 C6 C14 C13 . . . . -114.3(2) no C5 C6 C14 C15 . . . . 60.6(3) no C5 C6 C17 C18 . . . . -145.5(2) no C6 C7 C8 C9 . . . . 172.8(2) no C6 C7 C8 C13 . . . . 56.3(2) no C6 C7 C16 C12 . . . . -76.4(2) no C6 C14 C13 C8 . . . . 31.3(2) no C6 C14 C13 C12 . . . . -73.5(2) no C7 C6 C14 C13 . . . . 4.8(2) no C7 C6 C14 C15 . . . . 179.7(2) no C7 C6 C17 C18 . . . . 93.3(2) no C7 C8 C9 C10 . . . . -79.7(2) no C7 C8 C13 C12 . . . . 60.6(2) no C7 C8 C13 C14 . . . . -52.9(2) no C7 C16 C12 C11 . . . . -108.1(2) no C7 C16 C12 C13 . . . . 7.1(2) no C8 C7 C6 C14 . . . . -38.7(2) no C8 C7 C6 C17 . . . . -164.6(2) no C8 C7 C16 C12 . . . . 30.8(2) no C8 C9 C10 C11 . . . . 3.8(3) no C8 C9 C10 C20 . . . . -177.5(2) no C8 C13 C12 C11 . . . . 71.5(2) no C8 C13 C12 C16 . . . . -43.1(2) no C8 C13 C14 C15 . . . . -143.8(2) no C9 C8 C7 C16 . . . . 59.8(2) no C9 C8 C13 C12 . . . . -59.9(2) no C9 C8 C13 C14 . . . . -173.3(2) no C9 C10 C11 C12 . . . . 7.6(3) no C9 C10 C20 C21 . . . . -104.0(3) no C9 C10 C20 C22 . . . . 20.8(3) no C10 C9 C8 C13 . . . . 26.0(3) no C10 C11 C12 C13 . . . . -48.0(2) no C10 C11 C12 C16 . . . . 62.4(2) no C11 C10 C20 C21 . . . . 74.7(3) no C11 C10 C20 C22 . . . . -160.5(2) no C11 C12 C13 C14 . . . . 179.0(2) no C12 C11 C10 C20 . . . . -171.2(2) no C12 C13 C14 C15 . . . . 111.3(2) no C13 C8 C7 C16 . . . . -56.7(2) no C13 C14 C6 C17 . . . . 129.2(2) no C14 C6 C7 C16 . . . . 68.4(2) no C14 C6 C17 C18 . . . . -23.7(3) no C14 C13 C12 C16 . . . . 64.5(2) no C15 C14 C6 C17 . . . . -55.9(3) no C16 C7 C6 C17 . . . . -57.5(2) no C106 C107 C108 C109 . . . . 173.0(2) no C106 C107 C108 C113 . . . . 56.1(2) no C106 C107 C116 C112 . . . . -77.8(2) no C106 C114 C113 C108 . . . . 29.9(2) no C106 C114 C113 C112 . . . . -74.2(2) no C106 C1051 C1041 C1031 . . . . 41.2(8) no C106 C1052 C1042 C1032 . . . . -40(1) no C106 C1171 C1031 C1021 . . . . -107.7(6) no C106 C1171 C1031 C1041 . . . . 11.9(7) no C106 C1172 C1032 C1022 . . . . -119.2(9) no C106 C1172 C1032 C1042 . . . . 1(1) no C107 C106 C114 C113 . . . . 6.0(2) no C107 C106 C114 C115 . . . . -178.7(2) no C107 C106 C1051 C1041 . . . . 89.7(7) no C107 C106 C1052 C1042 . . . . 157.8(7) no C107 C106 C1171 C1031 . . . . -112.6(6) no C107 C106 C1171 C1181 . . . . 130.7(9) no C107 C106 C1172 C1032 . . . . -137.4(8) no C107 C106 C1172 C1182 . . . . 106(1) no C107 C108 C109 C110 . . . . -79.4(2) no C107 C108 C113 C112 . . . . 61.5(2) no C107 C108 C113 C114 . . . . -51.7(2) no C107 C116 C112 C111 . . . . -107.7(2) no C107 C116 C112 C113 . . . . 9.3(2) no C108 C107 C106 C114 . . . . -39.3(2) no C108 C107 C106 C1051 . . . . 78.4(4) no C108 C107 C106 C1052 . . . . 77.5(7) no C108 C107 C106 C1171 . . . . -163.9(4) no C108 C107 C106 C1172 . . . . -172.4(6) no C108 C107 C116 C112 . . . . 29.0(2) no C108 C109 C110 C111 . . . . 4.6(3) no C108 C109 C110 C120 . . . . -176.4(2) no C108 C113 C112 C111 . . . . 70.1(2) no C108 C113 C112 C116 . . . . -44.8(2) no C108 C113 C114 C115 . . . . -145.6(2) no C109 C108 C107 C116 . . . . 61.0(2) no C109 C108 C113 C112 . . . . -59.8(2) no C109 C108 C113 C114 . . . . -173.0(2) no C109 C110 C111 C112 . . . . 4.7(3) no C109 C110 C120 C1211 . . . . 42.2(8) no C109 C110 C120 C1212 . . . . 70.5(8) no C109 C110 C120 C1221 . . . . -84.4(9) no C109 C110 C120 C1222 . . . . -56(1) no C110 C109 C108 C113 . . . . 26.9(3) no C110 C111 C112 C113 . . . . -45.4(2) no C110 C111 C112 C116 . . . . 65.5(2) no C111 C110 C120 C1211 . . . . -138.8(8) no C111 C110 C120 C1212 . . . . -110.6(8) no C111 C110 C120 C1221 . . . . 94.6(9) no C111 C110 C120 C1222 . . . . 123(1) no C111 C112 C113 C114 . . . . 177.2(2) no C112 C111 C110 C120 . . . . -174.3(2) no C112 C113 C114 C115 . . . . 110.4(2) no C113 C108 C107 C116 . . . . -55.9(2) no C113 C114 C106 C1051 . . . . -116.5(5) no C113 C114 C106 C1052 . . . . -106(1) no C113 C114 C106 C1171 . . . . 127.7(5) no C113 C114 C106 C1172 . . . . 132.0(8) no C114 C106 C107 C116 . . . . 67.0(2) no C114 C106 C1051 C1041 . . . . -157.7(5) no C114 C106 C1052 C1042 . . . . -93.6(9) no C114 C106 C1171 C1031 . . . . 132.2(5) no C114 C106 C1171 C1181 . . . . 16(1) no C114 C106 C1172 C1032 . . . . 102.1(8) no C114 C106 C1172 C1182 . . . . -15(2) no C114 C113 C112 C116 . . . . 62.3(2) no C115 C114 C106 C1051 . . . . 58.8(6) no C115 C114 C106 C1052 . . . . 69(1) no C115 C114 C106 C1171 . . . . -57.0(6) no C115 C114 C106 C1172 . . . . -52.8(9) no C116 C107 C106 C1051 . . . . -175.4(4) no C116 C107 C106 C1052 . . . . -176.3(7) no C116 C107 C106 C1171 . . . . -57.6(4) no C116 C107 C106 C1172 . . . . -66.1(6) no C1021 O1011 C1181 C1171 . . . . 17.7(9) no C1021 C1031 C1041 C1051 . . . . 82.1(8) no C1021 C1031 C1171 C1181 . . . . 21.1(7) no C1022 O1012 C1182 C1172 . . . . 12(2) no C1022 C1032 C1042 C1052 . . . . 139(1) no C1022 C1032 C1172 C1182 . . . . 4(1) no C1031 C1021 O1011 C1181 . . . . -3.7(8) no C1031 C1171 C106 C1051 . . . . 12.8(8) no C1032 C1022 O1012 C1182 . . . . -10(1) no C1032 C1172 C106 C1052 . . . . -25(1) no C1041 C1031 C1171 C1181 . . . . 140.6(5) no C1041 C1051 C106 C1171 . . . . -33.3(9) no C1042 C1032 C1172 C1182 . . . . 124(1) no C1042 C1052 C106 C1172 . . . . 40(1) no C1051 C106 C1171 C1181 . . . . -104(1) no C1051 C1041 C1031 C1171 . . . . -32.7(8) no C1052 C106 C1172 C1182 . . . . -141(2) no C1052 C1042 C1032 C1172 . . . . 25(1) no #------------------------------------------------------------------------------ #===END data_she0524 _database_code_depnum_ccdc_archive 'CCDC 658577' _audit_creation_date 06-01-09 _audit_creation_method CRYSTALS_ver_12.18 # 10281406 she0519 _audit_update_record ; 2006-01-09 - Report on C20 H24 O4 by Anthony C. Willis for Natalie Miller and Mick Sherburn 2006-01-09 - passes checkcif tests with minor warnings ; # _oxford_structure_analysis_title '1091122 she0524' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.9554(2) _cell_length_b 9.8045(3) _cell_length_c 10.6568(3) _cell_angle_alpha 102.9314(13) _cell_angle_beta 113.3780(16) _cell_angle_gamma 91.0740(17) _cell_volume 831.03(4) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C19 H22 O4 # Dc = 1.26 Fooo = 352.00 Mu = 0.87 M = 314.38 # Found Formula = C20 H24 O4 # Dc = 1.31 FOOO = 352.00 Mu = 0.90 M = 328.41 _chemical_formula_sum 'C20 H24 O4' _chemical_formula_moiety 'C20 H24 O4' _chemical_compound_source local _chemical_formula_weight 328.41 _cell_measurement_reflns_used 12495 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 200 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.18 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.090 # Sheldrick geometric approximatio 0.97 0.98 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.200 0 -1 0 0.180 0 0 1 0.100 0 0 -1 0.080 1 0 -1 0.250 -1 0 1 0.250 1 0 3 0.091 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.049 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 2.0 deg at rate 60 sec/frame, crystal-detector distance 28mm, multiple scan sets so over 95 percent of data collected with 2-fold redundancy or more. ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_cell_refinement 'Denzo/Scalepack ' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Watkin et al 2003)' _computing_publication_material 'CRYSTALS ' _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 16625 _reflns_number_total 3765 _diffrn_reflns_av_R_equivalents 0.057 # Number of reflections with Friedels Law is 3765 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3818 _diffrn_reflns_theta_min 3.091 _diffrn_reflns_theta_max 27.500 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.500 _diffrn_measured_fraction_theta_full 0.986 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -11 _reflns_limit_h_max 10 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _oxford_diffrn_Wilson_B_factor 1.95 _oxford_diffrn_Wilson_scale 0.29 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.16 _refine_diff_density_max 0.22 _refine_ls_number_reflns 2983 _refine_ls_number_restraints 0 _refine_ls_number_parameters 217 #_refine_ls_R_factor_ref 0.0373 _refine_ls_wR_factor_ref 0.0413 _refine_ls_goodness_of_fit_ref 1.1107 #_reflns_number_all 3758 _refine_ls_R_factor_all 0.0478 _refine_ls_wR_factor_all 0.0455 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 2983 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_gt 0.0413 _refine_ls_shift/su_max 0.000501 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.32 -0.193 1.11 -0.142 0.316 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.90014(10) 0.62267(9) 0.90238(9) 0.0412 1.0000 Uani . . . . . . O18 O 1.08945(10) 0.51671(11) 0.84350(10) 0.0470 1.0000 Uani . . . . . . O20 O 0.41662(9) 0.19606(8) 0.38789(8) 0.0319 1.0000 Uani . . . . . . O21 O -0.09766(10) 0.14238(10) 0.50601(9) 0.0395 1.0000 Uani . . . . . . C2 C 0.94751(14) 0.51803(13) 0.82487(12) 0.0346 1.0000 Uani . . . . . . C3 C 0.80162(13) 0.41221(12) 0.72168(11) 0.0289 1.0000 Uani . . . . . . C4 C 0.79688(13) 0.28099(12) 0.77619(12) 0.0312 1.0000 Uani . . . . . . C5 C 0.63350(13) 0.18906(11) 0.68495(12) 0.0310 1.0000 Uani . . . . . . C6 C 0.48515(12) 0.26457(11) 0.69009(11) 0.0251 1.0000 Uani . . . . . . C7 C 0.32357(12) 0.18176(11) 0.57159(11) 0.0245 1.0000 Uani . . . . . . C8 C 0.30595(12) 0.16769(10) 0.42070(11) 0.0246 1.0000 Uani . . . . . . C9 C 0.13994(13) 0.11569(11) 0.30666(11) 0.0278 1.0000 Uani . . . . . . C10 C 0.00121(13) 0.11418(11) 0.32693(11) 0.0268 1.0000 Uani . . . . . . C11 C 0.01570(13) 0.16695(11) 0.47492(11) 0.0279 1.0000 Uani . . . . . . C12 C 0.17457(12) 0.25235(11) 0.58298(11) 0.0274 1.0000 Uani . . . . . . C13 C 0.18497(13) 0.40395(11) 0.56489(12) 0.0307 1.0000 Uani . . . . . . C14 C 0.35714(13) 0.47260(11) 0.61628(11) 0.0280 1.0000 Uani . . . . . . C15 C 0.49357(12) 0.41340(10) 0.67089(10) 0.0241 1.0000 Uani . . . . . . C16 C 0.65758(13) 0.49654(11) 0.71512(11) 0.0278 1.0000 Uani . . . . . . C17 C 0.72530(14) 0.59497(13) 0.86404(13) 0.0365 1.0000 Uani . . . . . . C19 C 0.48362(15) 0.27101(13) 0.83626(12) 0.0355 1.0000 Uani . . . . . . C22 C -0.16834(13) 0.06133(12) 0.21265(12) 0.0319 1.0000 Uani . . . . . . C23 C -0.28051(16) 0.17816(16) 0.20159(15) 0.0477 1.0000 Uani . . . . . . C24 C -0.16937(16) -0.00471(17) 0.06872(14) 0.0508 1.0000 Uani . . . . . . H31 H 0.80546 0.38541 0.62688 0.0334 1.0000 Uiso R . . . . . H41 H 0.80929 0.31025 0.87627 0.0350 1.0000 Uiso R . . . . . H42 H 0.88848 0.22631 0.77148 0.0350 1.0000 Uiso R . . . . . H51 H 0.63382 0.10202 0.71918 0.0343 1.0000 Uiso R . . . . . H52 H 0.62154 0.16238 0.58491 0.0343 1.0000 Uiso R . . . . . H71 H 0.31494 0.08470 0.58513 0.0288 1.0000 Uiso R . . . . . H91 H 0.13087 0.07935 0.20812 0.0324 1.0000 Uiso R . . . . . H121 H 0.17901 0.25780 0.67926 0.0326 1.0000 Uiso R . . . . . H131 H 0.12959 0.46283 0.61897 0.0352 1.0000 Uiso R . . . . . H132 H 0.12622 0.40041 0.46225 0.0352 1.0000 Uiso R . . . . . H141 H 0.37079 0.57157 0.60892 0.0322 1.0000 Uiso R . . . . . H161 H 0.64446 0.55575 0.64708 0.0318 1.0000 Uiso R . . . . . H171 H 0.67361 0.68449 0.86376 0.0397 1.0000 Uiso R . . . . . H172 H 0.70537 0.54814 0.93119 0.0397 1.0000 Uiso R . . . . . H191 H 0.38885 0.31938 0.84321 0.0412 1.0000 Uiso R . . . . . H192 H 0.58815 0.32467 0.91253 0.0412 1.0000 Uiso R . . . . . H193 H 0.47289 0.17313 0.84729 0.0412 1.0000 Uiso R . . . . . H221 H -0.21582 -0.01377 0.24070 0.0358 1.0000 Uiso R . . . . . H231 H -0.39167 0.14008 0.12519 0.0522 1.0000 Uiso R . . . . . H232 H -0.28966 0.21292 0.29362 0.0522 1.0000 Uiso R . . . . . H233 H -0.23344 0.25776 0.17875 0.0522 1.0000 Uiso R . . . . . H241 H -0.28482 -0.03736 -0.00188 0.0526 1.0000 Uiso R . . . . . H242 H -0.10474 -0.08692 0.07496 0.0526 1.0000 Uiso R . . . . . H243 H -0.11921 0.06676 0.03853 0.0526 1.0000 Uiso 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 0.0335(4) 0.0398(5) 0.0371(5) -0.0019(4) 0.0077(4) -0.0094(3) O18 0.0276(4) 0.0663(6) 0.0432(5) 0.0133(4) 0.0114(4) -0.0082(4) O20 0.0269(4) 0.0354(4) 0.0353(4) 0.0064(3) 0.0160(3) 0.0015(3) O21 0.0296(4) 0.0511(5) 0.0405(5) 0.0070(4) 0.0197(4) -0.0014(4) C2 0.0309(6) 0.0413(6) 0.0283(5) 0.0102(5) 0.0085(4) -0.0053(5) C3 0.0238(5) 0.0341(6) 0.0255(5) 0.0053(4) 0.0083(4) 0.0001(4) C4 0.0230(5) 0.0318(5) 0.0327(6) 0.0073(4) 0.0057(4) 0.0032(4) C5 0.0241(5) 0.0249(5) 0.0366(6) 0.0058(4) 0.0060(4) 0.0046(4) C6 0.0225(5) 0.0243(5) 0.0253(5) 0.0060(4) 0.0069(4) 0.0022(4) C7 0.0215(5) 0.0238(5) 0.0265(5) 0.0058(4) 0.0086(4) 0.0017(4) C8 0.0227(5) 0.0214(5) 0.0283(5) 0.0037(4) 0.0105(4) 0.0044(4) C9 0.0259(5) 0.0295(5) 0.0256(5) 0.0031(4) 0.0102(4) 0.0019(4) C10 0.0239(5) 0.0259(5) 0.0277(5) 0.0046(4) 0.0090(4) 0.0018(4) C11 0.0234(5) 0.0305(5) 0.0295(5) 0.0064(4) 0.0113(4) 0.0039(4) C12 0.0237(5) 0.0330(5) 0.0249(5) 0.0039(4) 0.0111(4) 0.0035(4) C13 0.0255(5) 0.0284(5) 0.0340(6) 0.0030(4) 0.0103(4) 0.0073(4) C14 0.0299(5) 0.0238(5) 0.0267(5) 0.0022(4) 0.0102(4) 0.0052(4) C15 0.0251(5) 0.0224(5) 0.0215(5) 0.0018(4) 0.0083(4) 0.0016(4) C16 0.0285(5) 0.0242(5) 0.0266(5) 0.0050(4) 0.0082(4) -0.0001(4) C17 0.0319(6) 0.0330(6) 0.0343(6) -0.0030(5) 0.0095(5) -0.0027(4) C19 0.0322(6) 0.0434(7) 0.0273(5) 0.0123(5) 0.0070(4) -0.0023(5) C22 0.0238(5) 0.0335(6) 0.0322(6) 0.0042(4) 0.0075(4) -0.0010(4) C23 0.0332(6) 0.0508(8) 0.0462(8) 0.0075(6) 0.0054(5) 0.0121(6) C24 0.0323(6) 0.0643(9) 0.0349(7) -0.0095(6) 0.0043(5) 0.0022(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.248(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.3527(16) yes O1 . C17 . 1.4557(14) yes O18 . C2 . 1.2070(14) yes O20 . C8 . 1.2207(13) yes O21 . C11 . 1.2215(13) yes C2 . C3 . 1.5136(15) yes C3 . C4 . 1.5318(16) yes C3 . C16 . 1.5318(15) yes C3 . H31 . 1.000 no C4 . C5 . 1.5257(15) yes C4 . H41 . 1.000 no C4 . H42 . 1.000 no C5 . C6 . 1.5468(14) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C6 . C7 . 1.5475(14) yes C6 . C15 . 1.5227(14) yes C6 . C19 . 1.5504(15) yes C7 . C8 . 1.5258(14) yes C7 . C12 . 1.5491(14) yes C7 . H71 . 1.000 no C8 . C9 . 1.4858(14) yes C9 . C10 . 1.3431(15) yes C9 . H91 . 1.000 no C10 . C11 . 1.4972(15) yes C10 . C22 . 1.5092(14) yes C11 . C12 . 1.5083(15) yes C12 . C13 . 1.5468(16) yes C12 . H121 . 1.000 no C13 . C14 . 1.5021(15) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C14 . C15 . 1.3348(14) yes C14 . H141 . 1.000 no C15 . C16 . 1.5092(14) yes C16 . C17 . 1.5318(15) yes C16 . H161 . 1.000 no C17 . H171 . 1.000 no C17 . H172 . 1.000 no C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C22 . C23 . 1.5312(17) yes C22 . C24 . 1.5219(17) yes C22 . H221 . 1.000 no C23 . H231 . 1.000 no C23 . H232 . 1.000 no C23 . H233 . 1.000 no C24 . H241 . 1.000 no C24 . H242 . 1.000 no C24 . H243 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C17 . 109.72(9) yes O1 . C2 . O18 . 120.94(11) yes O1 . C2 . C3 . 110.42(9) yes O18 . C2 . C3 . 128.64(12) yes C2 . C3 . C4 . 110.71(9) yes C2 . C3 . C16 . 102.14(9) yes C4 . C3 . C16 . 112.86(9) yes C2 . C3 . H31 . 110.3 no C4 . C3 . H31 . 110.3 no C16 . C3 . H31 . 110.3 no C3 . C4 . C5 . 109.47(9) yes C3 . C4 . H41 . 109.5 no C5 . C4 . H41 . 109.5 no C3 . C4 . H42 . 109.5 no C5 . C4 . H42 . 109.5 no H41 . C4 . H42 . 109.5 no C4 . C5 . C6 . 112.75(9) yes C4 . C5 . H51 . 108.6 no C6 . C5 . H51 . 108.6 no C4 . C5 . H52 . 108.7 no C6 . C5 . H52 . 108.6 no H51 . C5 . H52 . 109.5 no C5 . C6 . C7 . 110.47(8) yes C5 . C6 . C15 . 112.75(9) yes C7 . C6 . C15 . 107.26(8) yes C5 . C6 . C19 . 107.34(9) yes C7 . C6 . C19 . 109.70(8) yes C15 . C6 . C19 . 109.31(9) yes C6 . C7 . C8 . 115.90(8) yes C6 . C7 . C12 . 110.33(8) yes C8 . C7 . C12 . 106.53(8) yes C6 . C7 . H71 . 107.9 no C8 . C7 . H71 . 107.9 no C12 . C7 . H71 . 107.9 no C7 . C8 . O20 . 125.09(9) yes C7 . C8 . C9 . 116.40(9) yes O20 . C8 . C9 . 118.51(10) yes C8 . C9 . C10 . 124.44(10) yes C8 . C9 . H91 . 117.8 no C10 . C9 . H91 . 117.8 no C9 . C10 . C11 . 117.56(9) yes C9 . C10 . C22 . 125.23(10) yes C11 . C10 . C22 . 117.21(9) yes C10 . C11 . O21 . 120.99(10) yes C10 . C11 . C12 . 117.42(9) yes O21 . C11 . C12 . 121.60(10) yes C7 . C12 . C11 . 110.98(8) yes C7 . C12 . C13 . 109.50(8) yes C11 . C12 . C13 . 110.93(9) yes C7 . C12 . H121 . 108.5 no C11 . C12 . H121 . 108.5 no C13 . C12 . H121 . 108.5 no C12 . C13 . C14 . 113.83(9) yes C12 . C13 . H131 . 108.4 no C14 . C13 . H131 . 108.4 no C12 . C13 . H132 . 108.4 no C14 . C13 . H132 . 108.4 no H131 . C13 . H132 . 109.5 no C13 . C14 . C15 . 125.88(10) yes C13 . C14 . H141 . 117.1 no C15 . C14 . H141 . 117.1 no C6 . C15 . C14 . 120.82(9) yes C6 . C15 . C16 . 120.06(9) yes C14 . C15 . C16 . 119.12(9) yes C3 . C16 . C15 . 116.99(9) yes C3 . C16 . C17 . 101.54(9) yes C15 . C16 . C17 . 114.54(9) yes C3 . C16 . H161 . 107.8 no C15 . C16 . H161 . 107.8 no C17 . C16 . H161 . 107.8 no C16 . C17 . O1 . 104.53(9) yes C16 . C17 . H171 . 110.7 no O1 . C17 . H171 . 110.7 no C16 . C17 . H172 . 110.7 no O1 . C17 . H172 . 110.7 no H171 . C17 . H172 . 109.5 no C6 . C19 . H191 . 109.5 no C6 . C19 . H192 . 109.5 no H191 . C19 . H192 . 109.5 no C6 . C19 . H193 . 109.5 no H191 . C19 . H193 . 109.5 no H192 . C19 . H193 . 109.5 no C10 . C22 . C23 . 111.32(9) yes C10 . C22 . C24 . 113.51(10) yes C23 . C22 . C24 . 110.06(11) yes C10 . C22 . H221 . 107.2 no C23 . C22 . H221 . 107.2 no C24 . C22 . H221 . 107.2 no C22 . C23 . H231 . 109.5 no C22 . C23 . H232 . 109.5 no H231 . C23 . H232 . 109.5 no C22 . C23 . H233 . 109.5 no H231 . C23 . H233 . 109.5 no H232 . C23 . H233 . 109.5 no C22 . C24 . H241 . 109.5 no C22 . C24 . H242 . 109.5 no H241 . C24 . H242 . 109.5 no C22 . C24 . H243 . 109.5 no H241 . C24 . H243 . 109.5 no H242 . C24 . H243 . 109.5 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O18 3.267(2) . 2_767 no O1 C2 3.306(2) . 2_767 no O1 C4 3.327(1) . 2_767 no O1 O1 3.572(2) . 2_767 no O18 C17 3.340(2) . 2_767 no O18 C13 3.369(2) . 1_655 no O20 C16 3.422(1) . 2_666 no O20 C17 3.588(2) . 2_666 no O21 C11 3.165(2) . 2_556 no O21 O21 3.327(2) . 2_556 no O21 C10 3.333(2) . 2_556 no O21 C4 3.389(2) . 1_455 no O21 C3 3.480(2) . 1_455 no O21 C7 3.483(1) . 2_556 no O21 C5 3.597(2) . 1_455 no C2 C2 3.572(3) . 2_767 no C5 C8 3.548(1) . 2_656 no C11 C11 3.457(2) . 2_556 no C14 C16 3.563(2) . 2_666 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C2 C3 C4 . . . . -101.4(1) no O1 C2 C3 C16 . . . . 19.0(1) no O1 C17 C16 C3 . . . . 33.1(1) no O1 C17 C16 C15 . . . . 160.11(9) no O18 C2 O1 C17 . . . . -177.0(1) no O18 C2 C3 C4 . . . . 77.8(2) no O18 C2 C3 C16 . . . . -161.8(1) no O20 C8 C7 C6 . . . . 12.2(2) no O20 C8 C7 C12 . . . . 135.3(1) no O20 C8 C9 C10 . . . . -162.5(1) no O21 C11 C10 C9 . . . . -164.7(1) no O21 C11 C10 C22 . . . . 14.3(2) no O21 C11 C12 C7 . . . . 134.8(1) no O21 C11 C12 C13 . . . . -103.3(1) no C2 O1 C17 C16 . . . . -22.8(1) no C2 C3 C4 C5 . . . . 169.6(1) no C2 C3 C16 C15 . . . . -156.2(1) no C2 C3 C16 C17 . . . . -30.8(1) no C3 C2 O1 C17 . . . . 2.3(1) no C3 C4 C5 C6 . . . . -61.8(1) no C3 C16 C15 C6 . . . . 23.8(2) no C3 C16 C15 C14 . . . . -156.8(1) no C4 C3 C16 C15 . . . . -37.3(1) no C4 C3 C16 C17 . . . . 88.1(1) no C4 C5 C6 C7 . . . . 167.1(1) no C4 C5 C6 C15 . . . . 47.1(1) no C4 C5 C6 C19 . . . . -73.4(1) no C5 C4 C3 C16 . . . . 55.8(1) no C5 C6 C7 C8 . . . . -62.5(1) no C5 C6 C7 C12 . . . . 176.4(1) no C5 C6 C15 C14 . . . . 152.6(1) no C5 C6 C15 C16 . . . . -28.0(1) no C6 C7 C8 C9 . . . . -167.59(9) no C6 C7 C12 C11 . . . . -175.8(1) no C6 C7 C12 C13 . . . . 61.4(1) no C6 C15 C14 C13 . . . . -1.7(2) no C6 C15 C16 C17 . . . . -94.8(1) no C7 C6 C15 C14 . . . . 30.8(1) no C7 C6 C15 C16 . . . . -149.8(1) no C7 C8 C9 C10 . . . . 17.2(2) no C7 C12 C11 C10 . . . . -45.8(1) no C7 C12 C13 C14 . . . . -30.5(1) no C8 C7 C6 C15 . . . . 60.7(1) no C8 C7 C6 C19 . . . . 179.37(9) no C8 C7 C12 C11 . . . . 57.6(1) no C8 C7 C12 C13 . . . . -65.18(9) no C8 C9 C10 C11 . . . . -0.8(2) no C8 C9 C10 C22 . . . . -179.8(1) no C9 C8 C7 C12 . . . . -44.4(1) no C9 C10 C11 C12 . . . . 15.8(2) no C9 C10 C22 C23 . . . . -119.6(1) no C9 C10 C22 C24 . . . . 5.2(2) no C10 C11 C12 C13 . . . . 76.2(1) no C11 C10 C22 C23 . . . . 61.4(2) no C11 C10 C22 C24 . . . . -173.7(1) no C11 C12 C13 C14 . . . . -153.3(1) no C12 C7 C6 C15 . . . . -60.4(1) no C12 C7 C6 C19 . . . . 58.2(1) no C12 C11 C10 C22 . . . . -165.1(1) no C12 C13 C14 C15 . . . . 1.3(2) no C13 C14 C15 C16 . . . . 178.9(1) no C14 C15 C6 C19 . . . . -88.1(1) no C14 C15 C16 C17 . . . . 84.6(1) no C16 C15 C6 C19 . . . . 91.3(1) no #------------------------------------------------------------------------------ #===END data_she0601 _database_code_depnum_ccdc_archive 'CCDC 658578' _oxford_structure_analysis_title '1160928 she0601' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.8313(1) _cell_length_b 10.1677(2) _cell_length_c 25.1585(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1747.47(5) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C20 H26 O4 # Dc = 1.26 Fooo = 712.00 Mu = 0.86 M = 330.42 # Found Formula = C20 H26 O4 # Dc = 1.26 FOOO = 712.00 Mu = 0.86 M = 330.42 _chemical_formula_sum 'C20 H26 O4' _chemical_formula_moiety 'C20 H26 O4' _chemical_compound_source local _chemical_formula_weight 330.42 _cell_measurement_reflns_used 17752 _cell_measurement_theta_min 3 _cell_measurement_theta_max 25 _cell_measurement_temperature 200 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.36 _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.086 # Sheldrick geometric approximatio 0.99 0.99 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.170 -1 0 0 0.190 0 1 0 0.040 0 -1 0 0.020 0 0 1 0.070 0 0 -1 0.070 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.033 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 1.3 deg at rate 260 sec/frame, crystal-detector distance 34mm, multiple scan sets so over 95 percent of data collected with 4-fold redundancy or more [assuming Friedel's law]. ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_cell_refinement 'Denzo/Scalepack ' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Watkin et al 2003)' _computing_publication_material 'CRYSTALS ' _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 18576 _reflns_number_total 1806 _diffrn_reflns_av_R_equivalents 0.037 # Number of reflections with Friedels Law is 1806 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1542 _diffrn_reflns_theta_min 2.576 _diffrn_reflns_theta_max 25.0 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.020 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 29 _oxford_diffrn_Wilson_B_factor 3.19 _oxford_diffrn_Wilson_scale 1.41 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.15 _refine_diff_density_max 0.14 _refine_ls_number_reflns 1522 _refine_ls_number_restraints 0 _refine_ls_number_parameters 220 #_refine_ls_R_factor_ref 0.0336 _refine_ls_wR_factor_ref 0.0403 _refine_ls_goodness_of_fit_ref 1.0504 #_reflns_number_all 1796 _refine_ls_R_factor_all 0.0410 _refine_ls_wR_factor_all 0.0451 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.5\s(I) _reflns_number_gt 1522 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_gt 0.0403 _refine_ls_shift/su_max 0.000230 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_abs_structure_details ; The crystal comes from racemic solution. The absolute configuration could not be determined. The chirality of the molecule has been chosen arbitrarily. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.929 0.719 0.555 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.5150(3) 0.0543(2) 0.48965(7) 0.0664 1.0000 Uani . . . . . . O18 O 0.2000(4) 0.1061(2) 0.49993(8) 0.0742 1.0000 Uani . . . . . . O20 O 0.3465(2) 0.1541(2) 0.25217(6) 0.0482 1.0000 Uani . . . . . . O21 O 1.0591(2) 0.1341(2) 0.17644(6) 0.0449 1.0000 Uani . . . . . . C2 C 0.3399(5) 0.0963(3) 0.47116(10) 0.0547 1.0000 Uani . . . . . . C3 C 0.3539(4) 0.1283(2) 0.41263(8) 0.0396 1.0000 Uani . . . . . . C4 C 0.3811(4) 0.2773(2) 0.40587(8) 0.0367 1.0000 Uani . . . . . . C5 C 0.4390(3) 0.3077(2) 0.34864(8) 0.0357 1.0000 Uani . . . . . . C6 C 0.6332(3) 0.24246(19) 0.33136(7) 0.0277 1.0000 Uani . . . . . . C7 C 0.6640(3) 0.25335(19) 0.27035(7) 0.0269 1.0000 Uani . . . . . . C8 C 0.5026(3) 0.1977(2) 0.23532(8) 0.0321 1.0000 Uani . . . . . . C9 C 0.5461(3) 0.1865(2) 0.17817(8) 0.0315 1.0000 Uani . . . . . . C10 C 0.7271(3) 0.1861(2) 0.15819(8) 0.0293 1.0000 Uani . . . . . . C11 C 0.8988(3) 0.2112(2) 0.19437(8) 0.0321 1.0000 Uani . . . . . . C12 C 0.8544(3) 0.1849(2) 0.25295(8) 0.0300 1.0000 Uani . . . . . . C13 C 0.8421(3) 0.0378(2) 0.26555(8) 0.0359 1.0000 Uani . . . . . . C14 C 0.7343(3) 0.0088(2) 0.31638(8) 0.0354 1.0000 Uani . . . . . . C15 C 0.6387(3) 0.0963(2) 0.34606(7) 0.0296 1.0000 Uani . . . . . . C16 C 0.5363(4) 0.0510(2) 0.39583(9) 0.0404 1.0000 Uani . . . . . . C17 C 0.6578(5) 0.0575(3) 0.44693(9) 0.0594 1.0000 Uani . . . . . . C19 C 0.8031(3) 0.3151(3) 0.35946(8) 0.0411 1.0000 Uani . . . . . . C22 C 0.7715(3) 0.1617(2) 0.10012(8) 0.0362 1.0000 Uani . . . . . . C23 C 0.5896(4) 0.1417(3) 0.06586(8) 0.0474 1.0000 Uani . . . . . . C24 C 0.9005(5) 0.2704(3) 0.07671(9) 0.0566 1.0000 Uani . . . . . . H1 H 1.134(4) 0.133(3) 0.2001(11) 0.0520 1.0000 Uiso . . . . . . H31 H 0.2353 0.0969 0.39309 0.0475 1.0000 Uiso R . . . . . H41 H 0.4862 0.3087 0.43044 0.0440 1.0000 Uiso R . . . . . H42 H 0.2555 0.3232 0.41449 0.0440 1.0000 Uiso R . . . . . H51 H 0.4530 0.4051 0.34485 0.0428 1.0000 Uiso R . . . . . H52 H 0.3324 0.2758 0.32463 0.0428 1.0000 Uiso R . . . . . H71 H 0.6773 0.34886 0.26158 0.0323 1.0000 Uiso R . . . . . H91 H 0.4337 0.1789 0.15290 0.0377 1.0000 Uiso R . . . . . H111 H 0.9360 0.3059 0.19078 0.0386 1.0000 Uiso R . . . . . H121 H 0.9640 0.2227 0.27442 0.0359 1.0000 Uiso R . . . . . H131 H 0.9781 0.0022 0.26863 0.0431 1.0000 Uiso R . . . . . H132 H 0.7727 -0.0072 0.23565 0.0431 1.0000 Uiso R . . . . . H141 H 0.7344 -0.0845 0.32901 0.0425 1.0000 Uiso R . . . . . H161 H 0.4963 -0.0426 0.39038 0.0486 1.0000 Uiso R . . . . . H171 H 0.7356 0.1407 0.44823 0.0713 1.0000 Uiso R . . . . . H172 H 0.7482 -0.0196 0.44935 0.0713 1.0000 Uiso R . . . . . H191 H 0.9305 0.2744 0.34882 0.0492 1.0000 Uiso R . . . . . H192 H 0.7865 0.3079 0.39884 0.0492 1.0000 Uiso R . . . . . H193 H 0.8021 0.4099 0.34886 0.0492 1.0000 Uiso R . . . . . H221 H 0.8488 0.0783 0.09827 0.0435 1.0000 Uiso R . . . . . H231 H 0.6298 0.1261 0.02816 0.0568 1.0000 Uiso R . . . . . H232 H 0.5052 0.2219 0.06779 0.0568 1.0000 Uiso R . . . . . H233 H 0.5146 0.0639 0.07917 0.0568 1.0000 Uiso R . . . . . H241 H 0.9268 0.2511 0.03840 0.0679 1.0000 Uiso R . . . . . H242 H 1.0271 0.2742 0.09658 0.0679 1.0000 Uiso R . . . . . H243 H 0.8316 0.3568 0.07987 0.0679 1.0000 Uiso 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 0.0923(17) 0.0748(13) 0.0321(9) 0.0153(9) 0.0121(10) 0.0133(13) O18 0.0929(17) 0.0766(13) 0.0532(11) -0.0020(11) 0.0413(12) -0.0043(14) O20 0.0289(8) 0.0830(13) 0.0326(7) -0.0052(8) 0.0019(7) -0.0103(9) O21 0.0258(7) 0.0750(12) 0.0338(8) -0.0114(9) 0.0012(7) 0.0052(8) C2 0.079(2) 0.0455(13) 0.0394(13) -0.0013(11) 0.0191(15) -0.0036(16) C3 0.0451(13) 0.0419(12) 0.0319(10) -0.0032(9) 0.0091(11) -0.0048(11) C4 0.0400(12) 0.0402(11) 0.0298(10) -0.0036(9) 0.0026(10) 0.0035(10) C5 0.0421(11) 0.0381(11) 0.0270(10) -0.0026(10) 0.0025(9) 0.0085(11) C6 0.0294(10) 0.0307(9) 0.0228(9) -0.0006(8) -0.0008(9) 0.0005(9) C7 0.0297(10) 0.0278(9) 0.0232(8) -0.0008(8) 0.0001(8) 0.0005(9) C8 0.0262(10) 0.0412(11) 0.0289(11) 0.0004(9) -0.0014(9) 0.0043(9) C9 0.0294(10) 0.0408(11) 0.0242(10) -0.0003(9) -0.0032(8) 0.0031(10) C10 0.0339(10) 0.0286(9) 0.0255(9) -0.0012(8) -0.0006(8) -0.0003(9) C11 0.0271(10) 0.0384(11) 0.0308(10) -0.0042(9) 0.0049(8) -0.0037(9) C12 0.0235(9) 0.0405(11) 0.0259(9) -0.0041(9) -0.0008(8) -0.0006(9) C13 0.0366(11) 0.0404(11) 0.0308(10) 0.0005(9) 0.0033(10) 0.0108(11) C14 0.0389(11) 0.0343(11) 0.0330(10) 0.0035(9) -0.0003(10) 0.0068(9) C15 0.0298(10) 0.0339(10) 0.0250(9) 0.0021(8) -0.0012(9) 0.0005(9) C16 0.0532(13) 0.0343(11) 0.0339(11) 0.0064(9) 0.0091(11) 0.0015(11) C17 0.0704(18) 0.0749(18) 0.0329(12) 0.0167(12) 0.0040(13) 0.0212(17) C19 0.0439(12) 0.0484(13) 0.0309(11) -0.0066(10) -0.0017(10) -0.0108(12) C22 0.0420(11) 0.0413(12) 0.0254(9) -0.0014(9) 0.0040(9) 0.0037(11) C23 0.0535(15) 0.0618(15) 0.0268(10) -0.0069(10) -0.0071(10) 0.0107(13) C24 0.0662(18) 0.0661(17) 0.0375(13) 0.0094(12) 0.0173(12) -0.0049(14) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.856(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.353(4) yes O1 . C17 . 1.452(3) yes O18 . C2 . 1.203(3) yes O20 . C8 . 1.230(3) yes O21 . C11 . 1.421(3) yes O21 . H1 . 0.78(3) no C2 . C3 . 1.511(3) yes C3 . C4 . 1.536(3) yes C3 . C16 . 1.533(3) yes C3 . H31 . 1.000 no C4 . C5 . 1.525(3) yes C4 . H41 . 1.000 no C4 . H42 . 1.000 no C5 . C6 . 1.546(3) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C6 . C7 . 1.553(3) yes C6 . C15 . 1.532(3) yes C6 . C19 . 1.547(3) yes C7 . C8 . 1.521(3) yes C7 . C12 . 1.539(3) yes C7 . H71 . 1.000 no C8 . C9 . 1.473(3) yes C9 . C10 . 1.334(3) yes C9 . H91 . 1.000 no C10 . C11 . 1.506(3) yes C10 . C22 . 1.513(3) yes C11 . C12 . 1.528(3) yes C11 . H111 . 1.000 no C12 . C13 . 1.531(3) yes C12 . H121 . 1.000 no C13 . C14 . 1.505(3) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C14 . C15 . 1.333(3) yes C14 . H141 . 1.000 no C15 . C16 . 1.506(3) yes C16 . C17 . 1.532(3) yes C16 . H161 . 1.000 no C17 . H171 . 1.000 no C17 . H172 . 1.000 no C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C22 . C23 . 1.526(3) yes C22 . C24 . 1.531(3) yes C22 . H221 . 1.000 no C23 . H231 . 1.000 no C23 . H232 . 1.000 no C23 . H233 . 1.000 no C24 . H241 . 1.000 no C24 . H242 . 1.000 no C24 . H243 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C17 . 109.40(19) yes C11 . O21 . H1 . 105(2) no O1 . C2 . O18 . 121.5(2) yes O1 . C2 . C3 . 110.3(2) yes O18 . C2 . C3 . 128.2(3) yes C2 . C3 . C4 . 109.14(18) yes C2 . C3 . C16 . 102.1(2) yes C4 . C3 . C16 . 112.2(2) yes C2 . C3 . H31 . 111.0 no C4 . C3 . H31 . 111.0 no C16 . C3 . H31 . 111.0 no C3 . C4 . C5 . 109.63(18) yes C3 . C4 . H41 . 109.4 no C5 . C4 . H41 . 109.4 no C3 . C4 . H42 . 109.4 no C5 . C4 . H42 . 109.4 no H41 . C4 . H42 . 109.5 no C4 . C5 . C6 . 113.66(18) yes C4 . C5 . H51 . 108.4 no C6 . C5 . H51 . 108.4 no C4 . C5 . H52 . 108.4 no C6 . C5 . H52 . 108.4 no H51 . C5 . H52 . 109.5 no C5 . C6 . C7 . 111.33(16) yes C5 . C6 . C15 . 111.69(18) yes C7 . C6 . C15 . 107.73(15) yes C5 . C6 . C19 . 108.10(16) yes C7 . C6 . C19 . 108.41(16) yes C15 . C6 . C19 . 109.52(17) yes C6 . C7 . C8 . 116.62(17) yes C6 . C7 . C12 . 111.30(16) yes C8 . C7 . C12 . 106.23(15) yes C6 . C7 . H71 . 107.4 no C8 . C7 . H71 . 107.4 no C12 . C7 . H71 . 107.4 no C7 . C8 . O20 . 124.24(18) yes C7 . C8 . C9 . 116.62(17) yes O20 . C8 . C9 . 118.94(19) yes C8 . C9 . C10 . 123.72(18) yes C8 . C9 . H91 . 118.1 no C10 . C9 . H91 . 118.1 no C9 . C10 . C11 . 119.55(18) yes C9 . C10 . C22 . 123.38(18) yes C11 . C10 . C22 . 117.07(17) yes C10 . C11 . O21 . 108.37(16) yes C10 . C11 . C12 . 113.51(16) yes O21 . C11 . C12 . 111.25(18) yes C10 . C11 . H111 . 107.8 no O21 . C11 . H111 . 107.8 no C12 . C11 . H111 . 107.8 no C7 . C12 . C11 . 111.25(17) yes C7 . C12 . C13 . 109.65(17) yes C11 . C12 . C13 . 112.44(17) yes C7 . C12 . H121 . 107.8 no C11 . C12 . H121 . 107.8 no C13 . C12 . H121 . 107.8 no C12 . C13 . C14 . 113.23(17) yes C12 . C13 . H131 . 108.5 no C14 . C13 . H131 . 108.5 no C12 . C13 . H132 . 108.5 no C14 . C13 . H132 . 108.5 no H131 . C13 . H132 . 109.5 no C13 . C14 . C15 . 125.8(2) yes C13 . C14 . H141 . 117.1 no C15 . C14 . H141 . 117.1 no C6 . C15 . C14 . 121.65(19) yes C6 . C15 . C16 . 119.06(17) yes C14 . C15 . C16 . 119.3(2) yes C3 . C16 . C15 . 116.75(18) yes C3 . C16 . C17 . 100.78(19) yes C15 . C16 . C17 . 115.7(2) yes C3 . C16 . H161 . 107.7 no C15 . C16 . H161 . 107.7 no C17 . C16 . H161 . 107.7 no C16 . C17 . O1 . 104.9(2) yes C16 . C17 . H171 . 110.6 no O1 . C17 . H171 . 110.6 no C16 . C17 . H172 . 110.6 no O1 . C17 . H172 . 110.6 no H171 . C17 . H172 . 109.5 no C6 . C19 . H191 . 109.5 no C6 . C19 . H192 . 109.5 no H191 . C19 . H192 . 109.5 no C6 . C19 . H193 . 109.5 no H191 . C19 . H193 . 109.5 no H192 . C19 . H193 . 109.5 no C10 . C22 . C23 . 113.82(18) yes C10 . C22 . C24 . 111.63(19) yes C23 . C22 . C24 . 110.3(2) yes C10 . C22 . H221 . 106.9 no C23 . C22 . H221 . 106.9 no C24 . C22 . H221 . 106.9 no C22 . C23 . H231 . 109.4 no C22 . C23 . H232 . 109.5 no H231 . C23 . H232 . 109.5 no C22 . C23 . H233 . 109.5 no H231 . C23 . H233 . 109.5 no H232 . C23 . H233 . 109.5 no C22 . C24 . H241 . 109.5 no C22 . C24 . H242 . 109.5 no H241 . C24 . H242 . 109.5 no C22 . C24 . H243 . 109.5 no H241 . C24 . H243 . 109.5 no H242 . C24 . H243 . 109.5 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O18 C4 3.430(3) . 2_456 no O20 O21 2.743(2) . 1_455 no O20 C12 3.376(2) . 1_455 no O20 C11 3.436(2) . 1_455 no O21 C9 3.369(2) . 1_655 no O21 C8 3.434(2) . 1_655 no O21 C19 3.496(4) . 3_745 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C2 C3 C4 . . . . -98.4(3) no O1 C2 C3 C16 . . . . 20.5(3) no O1 C17 C16 C3 . . . . 34.0(2) no O1 C17 C16 C15 . . . . 160.9(2) no O18 C2 O1 C17 . . . . -177.6(3) no O18 C2 C3 C4 . . . . 80.5(4) no O18 C2 C3 C16 . . . . -160.6(3) no O20 C8 C7 C6 . . . . 5.3(3) no O20 C8 C7 C12 . . . . 130.0(2) no O20 C8 C9 C10 . . . . -155.6(2) no O21 C11 C10 C9 . . . . 145.5(2) no O21 C11 C10 C22 . . . . -34.6(2) no O21 C11 C12 C7 . . . . -172.1(2) no O21 C11 C12 C13 . . . . -48.6(2) no C2 O1 C17 C16 . . . . -22.9(3) no C2 C3 C4 C5 . . . . 167.9(2) no C2 C3 C16 C15 . . . . -158.2(2) no C2 C3 C16 C17 . . . . -32.1(2) no C3 C2 O1 C17 . . . . 1.4(3) no C3 C4 C5 C6 . . . . -60.6(3) no C3 C16 C15 C6 . . . . 30.9(3) no C3 C16 C15 C14 . . . . -150.1(2) no C4 C3 C16 C15 . . . . -41.5(3) no C4 C3 C16 C17 . . . . 84.6(2) no C4 C5 C6 C7 . . . . 168.7(2) no C4 C5 C6 C15 . . . . 48.3(2) no C4 C5 C6 C19 . . . . -72.3(2) no C5 C4 C3 C16 . . . . 55.5(3) no C5 C6 C7 C8 . . . . -56.3(2) no C5 C6 C7 C12 . . . . -178.4(2) no C5 C6 C15 C14 . . . . 148.0(2) no C5 C6 C15 C16 . . . . -33.1(2) no C6 C7 C8 C9 . . . . -169.5(2) no C6 C7 C12 C11 . . . . -172.4(2) no C6 C7 C12 C13 . . . . 62.6(2) no C6 C15 C14 C13 . . . . -1.6(3) no C6 C15 C16 C17 . . . . -87.4(3) no C7 C6 C15 C14 . . . . 25.5(3) no C7 C6 C15 C16 . . . . -155.6(2) no C7 C8 C9 C10 . . . . 19.5(3) no C7 C12 C11 C10 . . . . -49.6(2) no C7 C12 C13 C14 . . . . -36.1(2) no C8 C7 C6 C15 . . . . 66.5(2) no C8 C7 C6 C19 . . . . -175.0(2) no C8 C7 C12 C11 . . . . 59.7(2) no C8 C7 C12 C13 . . . . -65.3(2) no C8 C9 C10 C11 . . . . -6.1(3) no C8 C9 C10 C22 . . . . 174.0(2) no C9 C8 C7 C12 . . . . -44.8(2) no C9 C10 C11 C12 . . . . 21.4(3) no C9 C10 C22 C23 . . . . 1.8(3) no C9 C10 C22 C24 . . . . 127.5(2) no C10 C11 C12 C13 . . . . 73.9(2) no C11 C10 C22 C23 . . . . -178.1(2) no C11 C10 C22 C24 . . . . -52.3(3) no C11 C12 C13 C14 . . . . -160.4(2) no C12 C7 C6 C15 . . . . -55.6(2) no C12 C7 C6 C19 . . . . 62.9(2) no C12 C11 C10 C22 . . . . -158.8(2) no C12 C13 C14 C15 . . . . 6.8(3) no C13 C14 C15 C16 . . . . 179.5(2) no C14 C15 C6 C19 . . . . -92.3(2) no C14 C15 C16 C17 . . . . 91.6(3) no C16 C15 C6 C19 . . . . 86.7(2) no #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O21 H1 O20 0.79(3) 1.97(3) 2.743(2) 170(3) 1_655 yes #------------------------------------------------------------------------------ #===END data_she0601a _database_code_depnum_ccdc_archive 'CCDC 669352' _audit_creation_date 06-01-16 _audit_creation_method CRYSTALS_ver_12.18 _audit_update_record ; 2006-01-17 - Report on C20 H26 O4 [monoclinic] by Anthony C. Willis for Natalie Miller and Mick Sherburn 2006-01-17 - passes checkcif tests with minor warnings ; _oxford_structure_analysis_title '1161020 she0601a' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 30.8694(6) _cell_length_b 6.9089(1) _cell_length_c 17.0770(4) _cell_angle_alpha 90 _cell_angle_beta 102.9197(12) _cell_angle_gamma 90 _cell_volume 3549.87(12) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' _symmetry_space_group_name_Hall ? 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 -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C20 H26 O4 # Dc = 1.24 Fooo = 1424.00 Mu = 0.85 M = 330.42 # Found Formula = C20 H26 O4 # Dc = 1.24 FOOO = 1424.00 Mu = 0.85 M = 330.42 _chemical_formula_sum 'C20 H26 O4' _chemical_formula_moiety 'C20 H26 O4' _chemical_compound_source local _chemical_formula_weight 330.42 _cell_measurement_reflns_used 23282 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 200 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.13 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_max 0.29 _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.085 # Sheldrick geometric approximatio 0.98 0.99 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.050 -1 0 0 0.080 0 1 0 0.130 0 -1 0 0.160 0 0 1 0.140 0 0 -1 0.140 2 0 1 0.053 -2 0 -1 0.100 2 -1 4 0.073 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.042 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 2.0 deg at rate 48 sec/frame, crystal-detector distance 28mm, multiple scan sets so over 95 percent of data collected with 4-fold redundancy or more. ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_cell_refinement 'Denzo/Scalepack ' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Watkin et al 2003)' _computing_publication_material 'CRYSTALS ' _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 41222 _reflns_number_total 4060 _diffrn_reflns_av_R_equivalents 0.047 # Number of reflections with Friedels Law is 4060 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4076 _diffrn_reflns_theta_min 2.708 _diffrn_reflns_theta_max 27.5 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.497 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -40 _reflns_limit_h_max 38 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_diffrn_Wilson_B_factor 2.83 _oxford_diffrn_Wilson_scale 13.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.13 _refine_diff_density_max 0.19 _refine_ls_number_reflns 2406 _refine_ls_number_restraints 0 _refine_ls_number_parameters 295 #_refine_ls_R_factor_ref 0.0321 _refine_ls_wR_factor_ref 0.0380 _refine_ls_goodness_of_fit_ref 1.1124 #_reflns_number_all 4049 _refine_ls_R_factor_all 0.0612 _refine_ls_wR_factor_all 0.0614 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2406 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_gt 0.0380 _refine_ls_shift/su_max 0.002020 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refxyz # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.481 0.301 0.233 ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.30972(5) 0.5142(2) 0.82664(7) 0.0646 1.0000 Uani . . . . . . O18 O 0.29095(5) 0.2030(2) 0.81366(9) 0.0802 1.0000 Uani . . . . . . O20 O 0.39093(4) 0.35312(14) 0.53086(7) 0.0460 1.0000 Uani . . . . . . O21 O 0.43763(4) 1.06836(15) 0.47610(8) 0.0510 1.0000 Uani . . . . . . C2 C 0.30661(6) 0.3424(3) 0.78795(10) 0.0566 1.0000 Uani . . . . . . C3 C 0.32486(5) 0.3596(2) 0.71312(9) 0.0398 1.0000 Uani . . . . . . C4 C 0.28679(5) 0.3951(2) 0.63954(9) 0.0379 1.0000 Uani . . . . . . C5 C 0.30558(5) 0.4558(2) 0.56786(9) 0.0328 1.0000 Uani . . . . . . C6 C 0.33374(4) 0.64358(18) 0.58292(8) 0.0284 1.0000 Uani . . . . . . C7 C 0.35930(4) 0.67669(17) 0.51557(8) 0.0275 1.0000 Uani . . . . . . C8 C 0.38964(4) 0.51450(18) 0.50030(8) 0.0306 1.0000 Uani . . . . . . C9 C 0.42068(5) 0.5604(2) 0.44896(8) 0.0312 1.0000 Uani . . . . . . C10 C 0.43141(4) 0.74077(19) 0.43188(8) 0.0311 1.0000 Uani . . . . . . C11 C 0.40766(5) 0.91021(19) 0.45982(10) 0.0360 1.0000 Uani . . . . . . C12 C 0.38822(5) 0.85996(18) 0.53215(8) 0.0318 1.0000 Uani . . . . . . C13 C 0.42377(5) 0.8346(2) 0.60974(9) 0.0372 1.0000 Uani . . . . . . C14 C 0.40724(5) 0.7222(2) 0.67254(9) 0.0349 1.0000 Uani . . . . . . C15 C 0.36761(4) 0.63715(19) 0.66285(8) 0.0302 1.0000 Uani . . . . . . C16 C 0.35562(5) 0.5347(2) 0.73325(9) 0.0385 1.0000 Uani . . . . . . C17 C 0.33054(7) 0.6560(3) 0.78386(11) 0.0554 1.0000 Uani . . . . . . C19 C 0.30172(5) 0.8168(2) 0.58197(10) 0.0384 1.0000 Uani . . . . . . C22 C 0.46664(5) 0.7881(2) 0.38606(9) 0.0364 1.0000 Uani . . . . . . C23 C 0.49229(6) 0.6133(2) 0.36656(11) 0.0426 1.0000 Uani . . . . . . C24 C 0.44632(7) 0.9014(3) 0.30941(13) 0.0589 1.0000 Uani . . . . . . H1 H 0.4235(6) 1.158(3) 0.4942(12) 0.0600 1.0000 Uiso . . . . . . H31 H 0.3403(6) 0.240(3) 0.7055(10) 0.0480 1.0000 Uiso . . . . . . H41 H 0.2668(5) 0.495(3) 0.6528(10) 0.0460 1.0000 Uiso . . . . . . H42 H 0.2697(5) 0.271(3) 0.6288(10) 0.0460 1.0000 Uiso . . . . . . H51 H 0.3242(5) 0.348(2) 0.5563(9) 0.0394 1.0000 Uiso . . . . . . H52 H 0.2814(5) 0.479(2) 0.5192(10) 0.0394 1.0000 Uiso . . . . . . H71 H 0.3383(5) 0.692(2) 0.4650(9) 0.0327 1.0000 Uiso . . . . . . H91 H 0.4354(5) 0.448(2) 0.4326(9) 0.0380 1.0000 Uiso . . . . . . H111 H 0.3814(6) 0.939(2) 0.4129(10) 0.0442 1.0000 Uiso . . . . . . H121 H 0.3684(5) 0.970(2) 0.5382(9) 0.0390 1.0000 Uiso . . . . . . H131 H 0.4348(5) 0.965(2) 0.6318(10) 0.0449 1.0000 Uiso . . . . . . H132 H 0.4516(6) 0.770(2) 0.6006(10) 0.0449 1.0000 Uiso . . . . . . H141 H 0.4275(5) 0.708(2) 0.7240(10) 0.0413 1.0000 Uiso . . . . . . H161 H 0.3836(6) 0.490(2) 0.7683(10) 0.0457 1.0000 Uiso . . . . . . H171 H 0.3507(7) 0.738(3) 0.8265(13) 0.0693 1.0000 Uiso . . . . . . H172 H 0.3059(7) 0.738(3) 0.7488(13) 0.0693 1.0000 Uiso . . . . . . H191 H 0.3182(6) 0.936(3) 0.6058(10) 0.0469 1.0000 Uiso . . . . . . H192 H 0.2781(6) 0.785(2) 0.6110(10) 0.0469 1.0000 Uiso . . . . . . H193 H 0.2867(6) 0.844(2) 0.5257(11) 0.0469 1.0000 Uiso . . . . . . H221 H 0.4876(6) 0.875(2) 0.4212(10) 0.0448 1.0000 Uiso . . . . . . H231 H 0.5165(6) 0.657(3) 0.3416(11) 0.0527 1.0000 Uiso . . . . . . H232 H 0.5056(6) 0.537(3) 0.4171(11) 0.0527 1.0000 Uiso . . . . . . H233 H 0.4728(6) 0.523(3) 0.3306(11) 0.0527 1.0000 Uiso . . . . . . H241 H 0.4701(8) 0.942(3) 0.2843(12) 0.0746 1.0000 Uiso . . . . . . H242 H 0.4302(7) 1.018(3) 0.3217(13) 0.0746 1.0000 Uiso . . . . . . H243 H 0.4257(7) 0.817(3) 0.2692(13) 0.0746 1.0000 Uiso . . . . . . 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 0.0774(9) 0.0838(9) 0.0411(6) 0.0019(7) 0.0313(6) -0.0089(8) O18 0.0846(10) 0.0985(11) 0.0626(9) 0.0229(8) 0.0274(8) -0.0340(9) O20 0.0561(7) 0.0240(5) 0.0682(7) 0.0074(5) 0.0361(6) 0.0065(5) O21 0.0596(7) 0.0230(5) 0.0839(9) -0.0010(5) 0.0446(7) 0.0000(5) C2 0.0521(10) 0.0769(13) 0.0431(9) 0.0136(9) 0.0154(8) -0.0100(9) C3 0.0408(8) 0.0416(8) 0.0398(8) 0.0069(7) 0.0148(6) -0.0033(7) C4 0.0344(7) 0.0403(8) 0.0418(8) 0.0010(6) 0.0145(6) -0.0018(6) C5 0.0315(7) 0.0335(7) 0.0339(7) -0.0009(6) 0.0083(6) -0.0019(6) C6 0.0306(6) 0.0263(6) 0.0298(6) -0.0006(5) 0.0099(5) 0.0026(5) C7 0.0317(7) 0.0248(6) 0.0269(6) 0.0008(5) 0.0081(5) 0.0036(5) C8 0.0380(7) 0.0236(6) 0.0321(7) -0.0025(5) 0.0119(6) 0.0015(5) C9 0.0392(7) 0.0261(6) 0.0312(7) -0.0010(5) 0.0140(6) 0.0055(6) C10 0.0370(7) 0.0303(7) 0.0278(6) 0.0036(5) 0.0112(5) 0.0066(6) C11 0.0412(8) 0.0234(6) 0.0478(8) 0.0067(6) 0.0194(7) 0.0050(6) C12 0.0382(7) 0.0213(6) 0.0400(7) -0.0003(6) 0.0176(6) 0.0046(5) C13 0.0396(8) 0.0339(7) 0.0404(8) -0.0086(6) 0.0143(6) -0.0081(6) C14 0.0384(7) 0.0344(7) 0.0312(7) -0.0053(6) 0.0063(6) -0.0023(6) C15 0.0361(7) 0.0286(6) 0.0276(6) -0.0029(5) 0.0107(5) 0.0016(6) C16 0.0417(8) 0.0430(8) 0.0314(7) 0.0025(6) 0.0096(6) -0.0029(6) C17 0.0743(12) 0.0619(11) 0.0374(9) -0.0048(8) 0.0278(9) -0.0070(10) C19 0.0361(8) 0.0364(8) 0.0454(9) 0.0011(7) 0.0153(7) 0.0076(6) C22 0.0390(8) 0.0361(7) 0.0385(8) 0.0059(6) 0.0178(6) 0.0046(6) C23 0.0439(8) 0.0464(9) 0.0425(8) -0.0010(7) 0.0203(7) 0.0072(7) C24 0.0566(11) 0.0703(12) 0.0583(11) 0.0339(10) 0.0310(9) 0.0162(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3001(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.351(2) yes O1 . C17 . 1.455(2) yes O18 . C2 . 1.204(2) yes O20 . C8 . 1.2279(16) yes O21 . C11 . 1.4184(18) yes O21 . H1 . 0.85(2) no C2 . C3 . 1.512(2) yes C3 . C4 . 1.536(2) yes C3 . C16 . 1.529(2) yes C3 . H31 . 0.978(18) no C4 . C5 . 1.5259(19) yes C4 . H41 . 0.987(17) no C4 . H42 . 0.999(17) no C5 . C6 . 1.5506(18) yes C5 . H51 . 0.989(16) no C5 . H52 . 0.999(16) no C6 . C7 . 1.5503(17) yes C6 . C15 . 1.5232(18) yes C6 . C19 . 1.5496(19) yes C7 . C8 . 1.5200(17) yes C7 . C12 . 1.5386(18) yes C7 . H71 . 0.963(15) no C8 . C9 . 1.4707(18) yes C9 . C10 . 1.3380(19) yes C9 . H91 . 0.970(16) no C10 . C11 . 1.5140(18) yes C10 . C22 . 1.5107(19) yes C11 . C12 . 1.5289(19) yes C11 . H111 . 1.023(17) no C12 . C13 . 1.530(2) yes C12 . H121 . 0.998(16) no C13 . C14 . 1.503(2) yes C13 . H131 . 1.003(17) no C13 . H132 . 1.010(17) no C14 . C15 . 1.334(2) yes C14 . H141 . 0.963(17) no C15 . C16 . 1.5106(19) yes C16 . C17 . 1.532(2) yes C16 . H161 . 0.982(17) no C17 . H171 . 1.02(2) no C17 . H172 . 1.03(2) no C19 . H191 . 1.008(17) no C19 . H192 . 0.993(17) no C19 . H193 . 0.988(18) no C22 . C23 . 1.521(2) yes C22 . C24 . 1.534(2) yes C22 . H221 . 0.982(18) no C23 . H231 . 0.986(18) no C23 . H232 . 1.018(19) no C23 . H233 . 0.981(19) no C24 . H241 . 0.97(2) no C24 . H242 . 1.00(2) no C24 . H243 . 1.01(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C17 . 109.70(13) yes C11 . O21 . H1 . 105.3(13) no O1 . C2 . O18 . 120.99(16) yes O1 . C2 . C3 . 110.17(14) yes O18 . C2 . C3 . 128.84(19) yes C2 . C3 . C4 . 110.02(13) yes C2 . C3 . C16 . 101.68(13) yes C4 . C3 . C16 . 112.38(13) yes C2 . C3 . H31 . 109.3(10) no C4 . C3 . H31 . 109.4(10) no C16 . C3 . H31 . 113.8(10) no C3 . C4 . C5 . 109.97(12) yes C3 . C4 . H41 . 109.1(9) no C5 . C4 . H41 . 111.2(10) no C3 . C4 . H42 . 106.8(9) no C5 . C4 . H42 . 111.5(10) no H41 . C4 . H42 . 108.1(13) no C4 . C5 . C6 . 113.36(11) yes C4 . C5 . H51 . 107.1(9) no C6 . C5 . H51 . 109.7(9) no C4 . C5 . H52 . 111.4(9) no C6 . C5 . H52 . 107.0(9) no H51 . C5 . H52 . 108.3(13) no C5 . C6 . C7 . 111.09(10) yes C5 . C6 . C15 . 111.79(11) yes C7 . C6 . C15 . 107.93(10) yes C5 . C6 . C19 . 108.16(11) yes C7 . C6 . C19 . 107.91(11) yes C15 . C6 . C19 . 109.90(11) yes C6 . C7 . C8 . 117.00(10) yes C6 . C7 . C12 . 110.83(10) yes C8 . C7 . C12 . 106.49(10) yes C6 . C7 . H71 . 109.2(9) no C8 . C7 . H71 . 104.1(9) no C12 . C7 . H71 . 108.9(9) no C7 . C8 . O20 . 124.00(12) yes C7 . C8 . C9 . 116.86(11) yes O20 . C8 . C9 . 119.06(12) yes C8 . C9 . C10 . 123.83(12) yes C8 . C9 . H91 . 114.2(9) no C10 . C9 . H91 . 121.7(9) no C9 . C10 . C11 . 119.37(12) yes C9 . C10 . C22 . 123.80(12) yes C11 . C10 . C22 . 116.83(11) yes C10 . C11 . O21 . 108.47(11) yes C10 . C11 . C12 . 112.59(11) yes O21 . C11 . C12 . 111.91(13) yes C10 . C11 . H111 . 104.8(9) no O21 . C11 . H111 . 111.8(9) no C12 . C11 . H111 . 107.0(9) no C7 . C12 . C11 . 110.77(11) yes C7 . C12 . C13 . 109.85(11) yes C11 . C12 . C13 . 112.99(12) yes C7 . C12 . H121 . 107.7(9) no C11 . C12 . H121 . 105.7(9) no C13 . C12 . H121 . 109.6(9) no C12 . C13 . C14 . 112.64(12) yes C12 . C13 . H131 . 109.9(9) no C14 . C13 . H131 . 109.6(9) no C12 . C13 . H132 . 112.7(9) no C14 . C13 . H132 . 108.6(9) no H131 . C13 . H132 . 103.0(13) no C13 . C14 . C15 . 125.99(14) yes C13 . C14 . H141 . 116.8(9) no C15 . C14 . H141 . 117.2(9) no C6 . C15 . C14 . 121.68(12) yes C6 . C15 . C16 . 119.05(12) yes C14 . C15 . C16 . 119.26(13) yes C3 . C16 . C15 . 116.24(12) yes C3 . C16 . C17 . 101.10(13) yes C15 . C16 . C17 . 115.94(13) yes C3 . C16 . H161 . 107.9(10) no C15 . C16 . H161 . 107.1(10) no C17 . C16 . H161 . 108.1(10) no C16 . C17 . O1 . 104.53(14) yes C16 . C17 . H171 . 113.7(11) no O1 . C17 . H171 . 106.5(11) no C16 . C17 . H172 . 112.0(11) no O1 . C17 . H172 . 108.2(11) no H171 . C17 . H172 . 111.5(16) no C6 . C19 . H191 . 111.4(10) no C6 . C19 . H192 . 111.2(10) no H191 . C19 . H192 . 110.0(13) no C6 . C19 . H193 . 108.5(10) no H191 . C19 . H193 . 108.7(13) no H192 . C19 . H193 . 106.9(13) no C10 . C22 . C23 . 114.32(12) yes C10 . C22 . C24 . 110.37(12) yes C23 . C22 . C24 . 110.60(14) yes C10 . C22 . H221 . 105.5(10) no C23 . C22 . H221 . 108.2(10) no C24 . C22 . H221 . 107.4(10) no C22 . C23 . H231 . 109.5(10) no C22 . C23 . H232 . 111.0(10) no H231 . C23 . H232 . 109.0(14) no C22 . C23 . H233 . 111.3(11) no H231 . C23 . H233 . 110.0(15) no H232 . C23 . H233 . 106.0(14) no C22 . C24 . H241 . 108.7(12) no C22 . C24 . H242 . 111.2(12) no H241 . C24 . H242 . 108.7(17) no C22 . C24 . H243 . 111.1(13) no H241 . C24 . H243 . 107.0(17) no H242 . C24 . H243 . 110.1(17) no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C8 3.413(2) . 6_565 no O1 C7 3.505(2) . 6_565 no O18 C4 3.432(2) . 7_546 no O20 O21 2.725(2) . 1_545 no O20 C11 3.374(2) . 1_545 no O20 C12 3.408(2) . 1_545 no O21 C9 3.455(2) . 1_565 no O21 C8 3.484(2) . 1_565 no O21 C22 3.485(2) . 2_676 no C14 C24 3.524(2) . 6_575 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C2 C3 C4 . . . . -96.5(1) no O1 C2 C3 C16 . . . . 22.8(2) no O1 C17 C16 C3 . . . . 33.7(1) no O1 C17 C16 C15 . . . . 160.3(1) no O18 C2 O1 C17 . . . . 178.9(2) no O18 C2 C3 C4 . . . . 83.4(2) no O18 C2 C3 C16 . . . . -157.4(2) no O20 C8 C7 C6 . . . . 9.0(2) no O20 C8 C7 C12 . . . . 133.6(1) no O20 C8 C9 C10 . . . . -159.8(1) no O21 C11 C10 C9 . . . . 148.1(1) no O21 C11 C10 C22 . . . . -31.5(2) no O21 C11 C12 C7 . . . . -174.7(1) no O21 C11 C12 C13 . . . . -51.0(1) no C2 O1 C17 C16 . . . . -21.0(2) no C2 C3 C4 C5 . . . . 167.7(1) no C2 C3 C16 C15 . . . . -159.7(1) no C2 C3 C16 C17 . . . . -33.3(1) no C3 C2 O1 C17 . . . . -1.3(2) no C3 C4 C5 C6 . . . . -59.7(1) no C3 C16 C15 C6 . . . . 32.6(2) no C3 C16 C15 C14 . . . . -148.4(1) no C4 C3 C16 C15 . . . . -42.1(2) no C4 C3 C16 C17 . . . . 84.3(2) no C4 C5 C6 C7 . . . . 169.0(1) no C4 C5 C6 C15 . . . . 48.4(2) no C4 C5 C6 C19 . . . . -72.7(1) no C5 C4 C3 C16 . . . . 55.2(2) no C5 C6 C7 C8 . . . . -56.0(1) no C5 C6 C7 C12 . . . . -178.4(1) no C5 C6 C15 C14 . . . . 146.5(1) no C5 C6 C15 C16 . . . . -34.6(2) no C6 C7 C8 C9 . . . . -167.6(1) no C6 C7 C12 C11 . . . . -171.2(1) no C6 C7 C12 C13 . . . . 63.3(1) no C6 C15 C14 C13 . . . . 0.9(2) no C6 C15 C16 C17 . . . . -86.0(2) no C7 C6 C15 C14 . . . . 24.0(2) no C7 C6 C15 C16 . . . . -157.0(1) no C7 C8 C9 C10 . . . . 17.0(2) no C7 C12 C11 C10 . . . . -52.2(1) no C7 C12 C13 C14 . . . . -36.2(2) no C8 C7 C6 C15 . . . . 66.8(1) no C8 C7 C6 C19 . . . . -174.4(1) no C8 C7 C12 C11 . . . . 60.6(1) no C8 C7 C12 C13 . . . . -64.9(1) no C8 C9 C10 C11 . . . . -5.9(2) no C8 C9 C10 C22 . . . . 173.7(1) no C9 C8 C7 C12 . . . . -43.1(1) no C9 C10 C11 C12 . . . . 23.7(2) no C9 C10 C22 C23 . . . . -5.1(2) no C9 C10 C22 C24 . . . . 120.4(1) no C10 C11 C12 C13 . . . . 71.5(1) no C11 C10 C22 C23 . . . . 174.5(1) no C11 C10 C22 C24 . . . . -60.1(2) no C11 C12 C13 C14 . . . . -160.5(1) no C12 C7 C6 C15 . . . . -55.5(1) no C12 C7 C6 C19 . . . . 63.2(1) no C12 C11 C10 C22 . . . . -155.9(1) no C12 C13 C14 C15 . . . . 5.3(2) no C13 C14 C15 C16 . . . . -178.1(1) no C14 C15 C6 C19 . . . . -93.4(2) no C14 C15 C16 C17 . . . . 93.0(2) no C16 C15 C6 C19 . . . . 85.5(1) no #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O21 H1 O20 0.85(2) 1.87(2) 2.725(2) 178(2) 1_565 yes