Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_mss048 _database_code_depnum_ccdc_archive 'CCDC 644828' _audit_creation_date 04-01-11 _audit_creation_method CRYSTALS_ver_12-03-99 # 11010926 mss048 _audit_update_record ; 2004-11-01 - Report on C25 H24 O4 by Anthony C. Willis for Regis Tripoli and Mick Sherburn 2004-11-01 - passes checkcif tests with minor warnings ; #============================================================================== # 4. TEXT _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment refxyz #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; #============================================================= _cell_length_a 13.9345(2) _cell_angle_alpha 90 _cell_length_b 8.7920(2) _cell_angle_beta 96.0142(11) _cell_length_c 16.3108(3) _cell_angle_gamma 90 _cell_volume 1987.27(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1 ' 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 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . 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_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C25 H24 O4 ' _chemical_formula_moiety ' C25 H24 O4 ' _chemical_compound_source ; ? ; _chemical_formula_weight 388.46 _cell_measurement_reflns_used 24969 _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 0.14 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_max 0.46 _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_meas ' not measured ' # Non-dispersive F(000): _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.087 _diffrn_measurement_device_type ; Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _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 160 sec/frame, crystal-detector distance 28mm, multiple scan sets so over 95 percent of data collected with 4-fold redundancy or more [assuming Friedel Law]. ; # 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 0.200 -1 0 0 0.260 0 0 1 0.060 0 0 -1 0.080 0 -2 -2 0.113 0 1 1 0.130 0 -1 1 0.110 0 2 -2 0.148 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.968 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.037 # Sheldrick geometric definitions 0.98 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 200 _diffrn_reflns_number 41962 _reflns_number_total 4543 _diffrn_reflns_av_R_equivalents 0.05 # Number of reflections with Friedels Law is 4543 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4555 _diffrn_reflns_theta_min 2.635 _diffrn_reflns_theta_max 27.477 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.477 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -18 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _refine_diff_density_min -0.15 _refine_diff_density_max 0.17 _refine_ls_number_reflns 3260 _refine_ls_number_restraints 0 _refine_ls_number_parameters 334 #_refine_ls_R_factor_ref 0.0325 _refine_ls_wR_factor_ref 0.0351 _refine_ls_goodness_of_fit_ref 1.1283 #_reflns_number_all 4528 _refine_ls_R_factor_all 0.0485 _refine_ls_wR_factor_all 0.0427 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 3260 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_gt 0.0351 _refine_ls_shift/su_max 0.001518 _refine_ls_structure_factor_coef F _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: 0.857 0.561 0.698 0.187 0.178 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order 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 O2 O 0.89211(8) 0.50973(11) 0.54392(6) 0.0493 1.0000 Uani . . . . . . O10 O 0.92875(7) 0.26942(11) 0.51531(6) 0.0456 1.0000 Uani . . . . . . O12 O 0.81234(6) 0.10566(10) 0.35750(6) 0.0365 1.0000 Uani . . . . . . O13 O 0.96413(6) 0.14818(10) 0.33011(6) 0.0392 1.0000 Uani . . . . . . C1 C 0.84255(12) 0.63844(17) 0.50033(9) 0.0475 1.0000 Uani . . . . . . C3 C 0.89201(9) 0.38771(15) 0.49282(8) 0.0366 1.0000 Uani . . . . . . C4 C 0.83806(8) 0.43061(13) 0.41122(7) 0.0290 1.0000 Uani . . . . . . C5 C 0.86318(8) 0.36228(12) 0.33051(7) 0.0265 1.0000 Uani . . . . . . C6 C 0.78584(8) 0.41926(13) 0.26102(7) 0.0281 1.0000 Uani . . . . . . C7 C 0.75970(9) 0.58555(14) 0.27532(8) 0.0342 1.0000 Uani . . . . . . C8 C 0.78618(9) 0.66869(14) 0.34184(8) 0.0363 1.0000 Uani . . . . . . C9 C 0.85138(9) 0.60186(13) 0.41077(8) 0.0327 1.0000 Uani . . . . . . C11 C 0.87393(8) 0.19171(13) 0.33962(7) 0.0272 1.0000 Uani . . . . . . C14 C 0.98600(12) -0.00864(17) 0.35089(14) 0.0557 1.0000 Uani . . . . . . C15 C 0.69281(8) 0.32708(13) 0.24812(7) 0.0274 1.0000 Uani . . . . . . C16 C 0.62144(9) 0.37266(14) 0.17613(8) 0.0327 1.0000 Uani . . . . . . C17 C 0.67045(8) 0.21954(13) 0.17480(7) 0.0280 1.0000 Uani . . . . . . C18 C 0.74641(8) 0.19290(13) 0.11728(7) 0.0295 1.0000 Uani . . . . . . C19 C 0.75259(10) 0.27943(17) 0.04683(8) 0.0410 1.0000 Uani . . . . . . C20 C 0.82476(11) 0.25248(18) -0.00452(9) 0.0477 1.0000 Uani . . . . . . C21 C 0.89103(10) 0.13875(17) 0.01400(9) 0.0436 1.0000 Uani . . . . . . C22 C 0.88483(9) 0.04953(16) 0.08289(8) 0.0396 1.0000 Uani . . . . . . C23 C 0.81305(8) 0.07576(15) 0.13397(8) 0.0340 1.0000 Uani . . . . . . C24 C 0.60597(8) 0.08410(13) 0.18381(7) 0.0286 1.0000 Uani . . . . . . C25 C 0.61487(9) -0.00948(14) 0.25270(8) 0.0338 1.0000 Uani . . . . . . C26 C 0.55372(9) -0.13356(15) 0.25751(9) 0.0391 1.0000 Uani . . . . . . C27 C 0.48299(9) -0.16487(16) 0.19353(9) 0.0408 1.0000 Uani . . . . . . C28 C 0.47304(10) -0.07185(17) 0.12491(9) 0.0437 1.0000 Uani . . . . . . C29 C 0.53406(9) 0.05128(16) 0.11997(8) 0.0386 1.0000 Uani . . . . . . H11 H 0.8780(12) 0.735(2) 0.5213(10) 0.0587 1.0000 Uiso . . . . . . H12 H 0.7747(13) 0.6384(19) 0.5139(10) 0.0587 1.0000 Uiso . . . . . . H41 H 0.7694(10) 0.4090(15) 0.4179(8) 0.0348 1.0000 Uiso . . . . . . H51 H 0.9254(10) 0.4041(15) 0.3192(8) 0.0320 1.0000 Uiso . . . . . . H61 H 0.8164(10) 0.4155(15) 0.2085(9) 0.0342 1.0000 Uiso . . . . . . H71 H 0.7175(10) 0.6318(17) 0.2283(9) 0.0418 1.0000 Uiso . . . . . . H81 H 0.7680(10) 0.7748(18) 0.3452(9) 0.0436 1.0000 Uiso . . . . . . H91 H 0.9190(10) 0.6236(16) 0.4005(9) 0.0402 1.0000 Uiso . . . . . . H141 H 1.0496(14) -0.027(2) 0.3384(11) 0.0693 1.0000 Uiso . . . . . . H142 H 0.9785(13) -0.025(2) 0.4102(13) 0.0693 1.0000 Uiso . . . . . . H143 H 0.9400(14) -0.079(2) 0.3178(12) 0.0693 1.0000 Uiso . . . . . . H151 H 0.6647(9) 0.2983(15) 0.2992(8) 0.0322 1.0000 Uiso . . . . . . H161 H 0.6419(10) 0.4537(17) 0.1392(9) 0.0394 1.0000 Uiso . . . . . . H162 H 0.5526(11) 0.3696(16) 0.1841(8) 0.0394 1.0000 Uiso . . . . . . H191 H 0.7035(11) 0.3625(18) 0.0324(10) 0.0504 1.0000 Uiso . . . . . . H201 H 0.8274(12) 0.316(2) -0.0530(11) 0.0587 1.0000 Uiso . . . . . . H211 H 0.9419(11) 0.1224(18) -0.0218(10) 0.0526 1.0000 Uiso . . . . . . H221 H 0.9297(11) -0.0335(18) 0.0964(10) 0.0489 1.0000 Uiso . . . . . . H231 H 0.8098(10) 0.0132(17) 0.1839(9) 0.0420 1.0000 Uiso . . . . . . H251 H 0.6637(11) 0.0140(16) 0.2986(9) 0.0417 1.0000 Uiso . . . . . . H261 H 0.5590(11) -0.1965(18) 0.3082(10) 0.0486 1.0000 Uiso . . . . . . H271 H 0.4390(11) -0.2518(19) 0.1978(10) 0.0504 1.0000 Uiso . . . . . . H281 H 0.4230(12) -0.0913(18) 0.0794(10) 0.0527 1.0000 Uiso . . . . . . H291 H 0.5255(11) 0.1184(18) 0.0728(10) 0.0471 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 O2 0.0673(7) 0.0435(5) 0.0359(5) -0.0063(4) 0.0004(5) 0.0061(5) O10 0.0532(6) 0.0377(5) 0.0430(5) 0.0054(4) -0.0086(4) 0.0024(4) O12 0.0305(4) 0.0290(4) 0.0495(5) 0.0056(4) 0.0019(4) -0.0025(3) O13 0.0329(4) 0.0269(4) 0.0597(6) 0.0052(4) 0.0139(4) 0.0081(3) C1 0.0584(9) 0.0388(8) 0.0456(8) -0.0088(6) 0.0071(7) 0.0083(7) C3 0.0385(6) 0.0362(7) 0.0347(6) -0.0011(5) 0.0020(5) -0.0015(5) C4 0.0274(5) 0.0265(5) 0.0332(6) 0.0003(5) 0.0036(4) 0.0025(4) C5 0.0234(5) 0.0238(5) 0.0326(6) 0.0008(4) 0.0047(4) 0.0010(4) C6 0.0282(5) 0.0258(5) 0.0306(6) 0.0037(5) 0.0040(4) 0.0018(4) C7 0.0339(6) 0.0263(6) 0.0419(7) 0.0071(5) 0.0012(5) 0.0025(5) C8 0.0338(6) 0.0244(6) 0.0510(8) 0.0016(5) 0.0054(5) 0.0041(5) C9 0.0329(6) 0.0258(6) 0.0394(7) -0.0039(5) 0.0044(5) 0.0017(5) C11 0.0260(5) 0.0266(5) 0.0289(6) -0.0014(4) 0.0017(4) 0.0020(4) C14 0.0454(8) 0.0283(7) 0.0955(14) 0.0098(8) 0.0176(9) 0.0136(6) C15 0.0256(5) 0.0270(5) 0.0297(6) 0.0024(4) 0.0035(4) 0.0034(4) C16 0.0283(6) 0.0326(6) 0.0366(6) 0.0038(5) 0.0001(5) 0.0062(5) C17 0.0263(5) 0.0292(6) 0.0283(5) 0.0037(5) 0.0014(4) 0.0033(4) C18 0.0275(5) 0.0312(6) 0.0293(6) -0.0016(5) 0.0015(4) -0.0013(5) C19 0.0466(7) 0.0413(7) 0.0360(7) 0.0068(6) 0.0093(5) 0.0043(6) C20 0.0585(9) 0.0493(8) 0.0379(7) 0.0023(6) 0.0171(6) -0.0063(7) C21 0.0387(7) 0.0499(8) 0.0447(7) -0.0149(6) 0.0163(6) -0.0106(6) C22 0.0308(6) 0.0437(7) 0.0441(7) -0.0120(6) 0.0034(5) 0.0025(6) C23 0.0325(6) 0.0367(6) 0.0326(6) -0.0018(5) 0.0024(5) 0.0029(5) C24 0.0247(5) 0.0300(6) 0.0314(6) -0.0011(5) 0.0042(4) 0.0025(4) C25 0.0315(6) 0.0332(6) 0.0359(6) 0.0025(5) 0.0004(5) -0.0015(5) C26 0.0406(7) 0.0340(7) 0.0429(7) 0.0025(6) 0.0059(5) -0.0045(5) C27 0.0357(6) 0.0374(7) 0.0506(8) -0.0095(6) 0.0114(6) -0.0087(6) C28 0.0353(6) 0.0519(8) 0.0428(7) -0.0094(6) -0.0011(5) -0.0070(6) C29 0.0355(6) 0.0463(7) 0.0331(6) 0.0017(6) -0.0005(5) -0.0020(6) _refine_ls_extinction_method None 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 O2 . C1 . 1.4697(18) yes O2 . C3 . 1.3584(16) yes O10 . C3 . 1.1995(16) yes O12 . C11 . 1.2027(14) yes O13 . C11 . 1.3383(13) yes O13 . C14 . 1.4447(16) yes C1 . C9 . 1.5133(19) yes C1 . H11 . 1.025(18) no C1 . H12 . 0.993(17) no C3 . C4 . 1.5065(17) yes C4 . C5 . 1.5208(16) yes C4 . C9 . 1.5171(16) yes C4 . H41 . 0.993(14) no C5 . C6 . 1.5625(15) yes C5 . C11 . 1.5129(15) yes C5 . H51 . 0.977(14) no C6 . C7 . 1.5304(16) yes C6 . C15 . 1.5246(16) yes C6 . H61 . 0.997(14) no C7 . C8 . 1.3281(19) yes C7 . H71 . 1.002(15) no C8 . C9 . 1.4902(18) yes C8 . H81 . 0.969(16) no C9 . H91 . 0.992(14) no C14 . H141 . 0.94(2) no C14 . H142 . 0.99(2) no C14 . H143 . 1.00(2) no C15 . C16 . 1.5112(16) yes C15 . C17 . 1.5307(16) yes C15 . H151 . 0.990(14) no C16 . C17 . 1.5107(16) yes C16 . H161 . 0.994(15) no C16 . H162 . 0.982(14) no C17 . C18 . 1.5046(16) yes C17 . C24 . 1.5082(16) yes C18 . C19 . 1.3882(17) yes C18 . C23 . 1.3943(17) yes C19 . C20 . 1.3948(19) yes C19 . H191 . 1.011(16) no C20 . C21 . 1.373(2) yes C20 . H201 . 0.972(18) no C21 . C22 . 1.380(2) yes C21 . H211 . 0.975(16) no C22 . C23 . 1.3865(17) yes C22 . H221 . 0.971(16) no C23 . H231 . 0.987(15) no C24 . C25 . 1.3876(17) yes C24 . C29 . 1.3974(17) yes C25 . C26 . 1.3916(17) yes C25 . H251 . 0.980(15) no C26 . C27 . 1.3859(19) yes C26 . H261 . 0.991(16) no C27 . C28 . 1.381(2) yes C27 . H271 . 0.987(16) no C28 . C29 . 1.3841(19) yes C28 . H281 . 0.979(17) no C29 . H291 . 0.968(16) 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 C1 . O2 . C3 . 109.94(10) yes C11 . O13 . C14 . 115.05(10) yes O2 . C1 . C9 . 102.81(10) yes O2 . C1 . H11 . 107.0(9) no C9 . C1 . H11 . 114.4(10) no O2 . C1 . H12 . 107.6(10) no C9 . C1 . H12 . 112.9(10) no H11 . C1 . H12 . 111.3(14) no O2 . C3 . O10 . 121.61(12) yes O2 . C3 . C4 . 108.22(10) yes O10 . C3 . C4 . 130.15(12) yes C3 . C4 . C5 . 121.81(10) yes C3 . C4 . C9 . 101.70(10) yes C5 . C4 . C9 . 110.40(10) yes C3 . C4 . H41 . 104.6(8) no C5 . C4 . H41 . 109.3(8) no C9 . C4 . H41 . 108.1(8) no C4 . C5 . C6 . 107.31(9) yes C4 . C5 . C11 . 109.63(9) yes C6 . C5 . C11 . 116.27(9) yes C4 . C5 . H51 . 107.7(8) no C6 . C5 . H51 . 107.5(8) no C11 . C5 . H51 . 108.1(8) no C5 . C6 . C7 . 110.66(10) yes C5 . C6 . C15 . 116.20(9) yes C7 . C6 . C15 . 108.44(9) yes C5 . C6 . H61 . 106.8(8) no C7 . C6 . H61 . 107.0(8) no C15 . C6 . H61 . 107.3(8) no C6 . C7 . C8 . 126.88(11) yes C6 . C7 . H71 . 113.6(8) no C8 . C7 . H71 . 119.5(8) no C7 . C8 . C9 . 119.64(11) yes C7 . C8 . H81 . 121.6(9) no C9 . C8 . H81 . 118.6(9) no C4 . C9 . C1 . 100.60(11) yes C4 . C9 . C8 . 109.25(10) yes C1 . C9 . C8 . 122.66(11) yes C4 . C9 . H91 . 108.1(8) no C1 . C9 . H91 . 107.2(8) no C8 . C9 . H91 . 108.2(8) no C5 . C11 . O13 . 110.89(9) yes C5 . C11 . O12 . 125.56(10) yes O13 . C11 . O12 . 123.43(10) yes O13 . C14 . H141 . 107.1(12) no O13 . C14 . H142 . 108.9(11) no H141 . C14 . H142 . 112.5(16) no O13 . C14 . H143 . 110.7(11) no H141 . C14 . H143 . 109.7(15) no H142 . C14 . H143 . 108.0(15) no C6 . C15 . C16 . 116.56(10) yes C6 . C15 . C17 . 122.45(10) yes C16 . C15 . C17 . 59.55(7) yes C6 . C15 . H151 . 115.1(8) no C16 . C15 . H151 . 115.9(8) no C17 . C15 . H151 . 115.7(8) no C15 . C16 . C17 . 60.87(7) yes C15 . C16 . H161 . 117.0(8) no C17 . C16 . H161 . 118.1(8) no C15 . C16 . H162 . 117.6(8) no C17 . C16 . H162 . 115.3(8) no H161 . C16 . H162 . 116.5(12) no C15 . C17 . C16 . 59.58(7) yes C15 . C17 . C18 . 118.98(9) yes C16 . C17 . C18 . 119.76(10) yes C15 . C17 . C24 . 119.09(10) yes C16 . C17 . C24 . 115.30(9) yes C18 . C17 . C24 . 113.77(9) yes C17 . C18 . C19 . 122.65(11) yes C17 . C18 . C23 . 119.40(10) yes C19 . C18 . C23 . 117.95(11) yes C18 . C19 . C20 . 121.00(13) yes C18 . C19 . H191 . 119.3(9) no C20 . C19 . H191 . 119.7(9) no C19 . C20 . C21 . 120.14(13) yes C19 . C20 . H201 . 118.8(10) no C21 . C20 . H201 . 121.1(10) no C20 . C21 . C22 . 119.66(12) yes C20 . C21 . H211 . 119.3(10) no C22 . C21 . H211 . 121.0(10) no C21 . C22 . C23 . 120.35(13) yes C21 . C22 . H221 . 121.2(9) no C23 . C22 . H221 . 118.5(9) no C18 . C23 . C22 . 120.87(12) yes C18 . C23 . H231 . 119.0(8) no C22 . C23 . H231 . 120.1(8) no C17 . C24 . C25 . 122.92(10) yes C17 . C24 . C29 . 118.58(11) yes C25 . C24 . C29 . 118.50(11) yes C24 . C25 . C26 . 120.48(12) yes C24 . C25 . H251 . 119.3(9) no C26 . C25 . H251 . 120.2(9) no C25 . C26 . C27 . 120.30(13) yes C25 . C26 . H261 . 119.5(9) no C27 . C26 . H261 . 120.2(9) no C26 . C27 . C28 . 119.71(12) yes C26 . C27 . H271 . 119.9(9) no C28 . C27 . H271 . 120.3(9) no C27 . C28 . C29 . 120.00(13) yes C27 . C28 . H281 . 120.9(10) no C29 . C28 . H281 . 119.1(10) no C24 . C29 . C28 . 121.00(13) yes C24 . C29 . H291 . 119.1(9) no C28 . C29 . H291 . 119.8(9) 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 O2 C3 3.256(2) . 2_766 no O2 C25 3.333(2) . 3_656 no O2 O10 3.382(2) . 2_766 no O2 O2 3.468(2) . 2_766 no O2 C26 3.484(2) . 3_656 no O2 O12 3.517(1) . 3_656 no O10 C14 3.300(2) . 2_756 no O10 C1 3.324(2) . 2_766 no O10 C9 3.368(2) . 2_766 no O12 C1 3.342(2) . 3_646 no O13 C16 3.507(2) . 4 no O13 C15 3.589(2) . 4 no C3 C3 3.587(2) . 2_766 no C7 C27 3.580(2) . 4 no C16 C22 3.550(2) . 4_455 no C19 C22 3.596(2) . 3_655 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 O2 C1 C9 C4 . . . . 38.0(1) no O2 C1 C9 C8 . . . . 159.2(1) no O2 C3 C4 C5 . . . . 149.1(1) no O2 C3 C4 C9 . . . . 25.9(1) no O10 C3 O2 C1 . . . . 179.9(1) no O10 C3 C4 C5 . . . . -32.6(2) no O10 C3 C4 C9 . . . . -155.8(1) no O12 C11 O13 C14 . . . . -5.9(2) no O12 C11 C5 C4 . . . . 59.3(1) no O12 C11 C5 C6 . . . . -62.6(2) no O13 C11 C5 C4 . . . . -116.9(1) no O13 C11 C5 C6 . . . . 121.2(1) no C1 O2 C3 C4 . . . . -1.6(1) no C1 C9 C4 C3 . . . . -38.5(1) no C1 C9 C4 C5 . . . . -169.1(1) no C1 C9 C8 C7 . . . . -144.4(1) no C3 O2 C1 C9 . . . . -23.5(1) no C3 C4 C5 C6 . . . . 174.0(1) no C3 C4 C5 C11 . . . . 46.9(1) no C3 C4 C9 C8 . . . . -168.8(1) no C4 C5 C6 C7 . . . . 39.0(1) no C4 C5 C6 C15 . . . . -85.2(1) no C4 C9 C8 C7 . . . . -27.3(2) no C5 C4 C9 C8 . . . . 60.6(1) no C5 C6 C7 C8 . . . . -8.9(2) no C5 C6 C15 C16 . . . . -174.6(1) no C5 C6 C15 C17 . . . . -105.3(1) no C5 C11 O13 C14 . . . . 170.3(1) no C6 C5 C4 C9 . . . . -67.0(1) no C6 C7 C8 C9 . . . . 2.6(2) no C6 C15 C16 C17 . . . . 113.7(1) no C6 C15 C17 C16 . . . . -103.9(1) no C6 C15 C17 C18 . . . . 5.5(2) no C6 C15 C17 C24 . . . . 152.2(1) no C7 C6 C5 C11 . . . . 162.1(1) no C7 C6 C15 C16 . . . . 60.0(1) no C7 C6 C15 C17 . . . . 129.3(1) no C8 C7 C6 C15 . . . . 119.6(1) no C9 C4 C5 C11 . . . . 165.90(9) no C11 C5 C6 C15 . . . . 37.9(1) no C15 C16 C17 C18 . . . . -108.1(1) no C15 C16 C17 C24 . . . . 110.2(1) no C15 C17 C18 C19 . . . . -91.7(1) no C15 C17 C18 C23 . . . . 89.2(1) no C15 C17 C24 C25 . . . . -44.4(2) no C15 C17 C24 C29 . . . . 135.6(1) no C16 C15 C17 C18 . . . . 109.4(1) no C16 C15 C17 C24 . . . . -103.9(1) no C16 C17 C18 C19 . . . . -22.2(2) no C16 C17 C18 C23 . . . . 158.7(1) no C16 C17 C24 C25 . . . . -112.2(1) no C16 C17 C24 C29 . . . . 67.8(1) no C17 C18 C19 C20 . . . . 179.2(1) no C17 C18 C23 C22 . . . . -179.1(1) no C17 C24 C25 C26 . . . . -179.6(1) no C17 C24 C29 C28 . . . . 179.8(1) no C18 C17 C24 C25 . . . . 103.9(1) no C18 C17 C24 C29 . . . . -76.1(1) no C18 C19 C20 C21 . . . . 0.2(2) no C18 C23 C22 C21 . . . . -0.5(2) no C19 C18 C17 C24 . . . . 120.0(1) no C19 C18 C23 C22 . . . . 1.8(2) no C19 C20 C21 C22 . . . . 1.1(2) no C20 C19 C18 C23 . . . . -1.6(2) no C20 C21 C22 C23 . . . . -1.0(2) no C23 C18 C17 C24 . . . . -59.2(1) no C24 C25 C26 C27 . . . . -0.2(2) no C24 C29 C28 C27 . . . . -0.3(2) no C25 C24 C29 C28 . . . . -0.2(2) no C25 C26 C27 C28 . . . . -0.3(2) no C26 C25 C24 C29 . . . . 0.4(2) no C26 C27 C28 C29 . . . . 0.5(2) no data_she0501 _database_code_depnum_ccdc_archive 'CCDC 644829' _audit_creation_date 05-07-01 _audit_creation_method CRYSTALS_ver_12-03-99 # 1061713 she0501 _audit_update_record ; 2005-01-07 - Report on C27 H26 O6 by Anthony C. Willis for Regis Tripoli and Mick Sherburn 2005-01-07 - passes checkcif tests with minor warnings ; #============================================================================== # 4. TEXT _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; #============================================================= _cell_length_a 15.0402(3) _cell_angle_alpha 90 _cell_length_b 15.3235(3) _cell_angle_beta 90 _cell_length_c 19.7863(5) _cell_angle_gamma 90 _cell_volume 4560.12(17) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' 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+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . 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_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B _cell_formula_units_Z 8 _chemical_formula_sum ' C27 H26 O6 ' _chemical_formula_moiety ' C27 H26 O6 ' _chemical_compound_source ; ? ; _chemical_formula_weight 446.50 _cell_measurement_reflns_used 34830 _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 0.04 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1888 _exptl_absorpt_coefficient_mu 0.092 _diffrn_measurement_device_type ; Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 1.8 deg at rate 324 sec/frame, crystal-detector distance 32mm, multiple scan sets so over 95 percent of data collected with 4-fold redundancy or more [assuming Friedel Law]. ; # 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 0.140 -1 0 0 0.110 0 0 1 0.020 0 0 -1 0.020 0 -1 0 0.191 -1 2 0 0.200 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.049 # Sheldrick geometric definitions 0.98 1.00 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 200 _diffrn_reflns_number 40672 _reflns_number_total 4046 _diffrn_reflns_av_R_equivalents 0.05 # Number of reflections with Friedels Law is 4046 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4064 _diffrn_reflns_theta_min 2.658 _diffrn_reflns_theta_max 25.0 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.105 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min 0 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _refine_diff_density_min -0.17 _refine_diff_density_max 0.23 _refine_ls_number_reflns 2621 _refine_ls_number_restraints 0 _refine_ls_number_parameters 298 #_refine_ls_R_factor_ref 0.0325 _refine_ls_wR_factor_ref 0.0361 _refine_ls_goodness_of_fit_ref 1.0664 #_reflns_number_all 3212 _refine_ls_R_factor_all 0.0402 _refine_ls_wR_factor_all 0.0410 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 2621 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_gt 0.0361 _refine_ls_shift/su_max 0.000306 _refine_ls_structure_factor_coef F _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: 0.792 0.326 0.497 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order 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 O2 O 0.32220(9) 0.29842(8) 0.23847(6) 0.0472 1.0000 Uani . . . . . . O10 O 0.35786(9) 0.17698(9) 0.29476(6) 0.0478 1.0000 Uani . . . . . . O12 O 0.28398(8) 0.14272(8) 0.48829(6) 0.0446 1.0000 Uani . . . . . . O13 O 0.39997(7) 0.21299(7) 0.44218(6) 0.0348 1.0000 Uani . . . . . . O31 O 0.09680(8) 0.23921(10) 0.43206(8) 0.0549 1.0000 Uani . . . . . . O32 O 0.17547(8) 0.15795(8) 0.36054(6) 0.0460 1.0000 Uani . . . . . . C1 C 0.28088(13) 0.38282(13) 0.25321(10) 0.0476 1.0000 Uani . . . . . . C3 C 0.32737(11) 0.24904(12) 0.29587(8) 0.0375 1.0000 Uani . . . . . . C4 C 0.29380(10) 0.30441(10) 0.35368(8) 0.0314 1.0000 Uani . . . . . . C5 C 0.25493(10) 0.26747(10) 0.41884(8) 0.0305 1.0000 Uani . . . . . . C6 C 0.23846(11) 0.34656(10) 0.46818(8) 0.0325 1.0000 Uani . . . . . . C7 C 0.20703(12) 0.42718(11) 0.43086(9) 0.0400 1.0000 Uani . . . . . . C8 C 0.20369(12) 0.43845(11) 0.36420(9) 0.0417 1.0000 Uani . . . . . . C9 C 0.22932(11) 0.36564(11) 0.31786(8) 0.0368 1.0000 Uani . . . . . . C11 C 0.31375(11) 0.20011(10) 0.45350(8) 0.0319 1.0000 Uani . . . . . . C14 C 0.45857(12) 0.15355(11) 0.47797(10) 0.0436 1.0000 Uani . . . . . . C15 C 0.31900(11) 0.37172(10) 0.51063(8) 0.0332 1.0000 Uani . . . . . . C16 C 0.34753(13) 0.32025(11) 0.57179(9) 0.0391 1.0000 Uani . . . . . . C17 C 0.30605(11) 0.40904(10) 0.58189(8) 0.0323 1.0000 Uani . . . . . . C18 C 0.21395(11) 0.41457(10) 0.61178(8) 0.0331 1.0000 Uani . . . . . . C19 C 0.17692(13) 0.34725(12) 0.64948(9) 0.0442 1.0000 Uani . . . . . . C20 C 0.09200(15) 0.35547(14) 0.67661(10) 0.0556 1.0000 Uani . . . . . . C21 C 0.04317(13) 0.43021(14) 0.66733(10) 0.0526 1.0000 Uani . . . . . . C22 C 0.07976(12) 0.49852(13) 0.63103(9) 0.0463 1.0000 Uani . . . . . . C23 C 0.16436(11) 0.49073(11) 0.60353(9) 0.0375 1.0000 Uani . . . . . . C24 C 0.36559(11) 0.48311(10) 0.60360(8) 0.0317 1.0000 Uani . . . . . . C25 C 0.38827(12) 0.55013(12) 0.56018(10) 0.0431 1.0000 Uani . . . . . . C26 C 0.43921(13) 0.62034(12) 0.58240(11) 0.0513 1.0000 Uani . . . . . . C27 C 0.46696(12) 0.62353(12) 0.64897(11) 0.0470 1.0000 Uani . . . . . . C28 C 0.44549(12) 0.55691(12) 0.69259(10) 0.0440 1.0000 Uani . . . . . . C29 C 0.39493(11) 0.48668(11) 0.67052(9) 0.0372 1.0000 Uani . . . . . . C30 C 0.16591(11) 0.22168(11) 0.40570(8) 0.0344 1.0000 Uani . . . . . . C33 C 0.09733(13) 0.10436(14) 0.34939(11) 0.0546 1.0000 Uani . . . . . . H11 H 0.24010(13) 0.40095(13) 0.21585(10) 0.0559 1.0000 Uiso R . . . . . H12 H 0.32698(13) 0.42893(13) 0.26034(10) 0.0559 1.0000 Uiso R . . . . . H41 H 0.34553(10) 0.34129(10) 0.36755(8) 0.0357 1.0000 Uiso R . . . . . H61 H 0.19010(11) 0.32880(10) 0.50001(8) 0.0368 1.0000 Uiso R . . . . . H71 H 0.18674(12) 0.47729(11) 0.45933(9) 0.0462 1.0000 Uiso R . . . . . H81 H 0.18415(12) 0.49572(11) 0.34506(9) 0.0480 1.0000 Uiso R . . . . . H91 H 0.17459(11) 0.33192(11) 0.30597(8) 0.0424 1.0000 Uiso R . . . . . H141 H 0.52180(12) 0.16763(11) 0.46678(10) 0.0508 1.0000 Uiso R . . . . . H142 H 0.44519(12) 0.09219(11) 0.46410(10) 0.0508 1.0000 Uiso R . . . . . H143 H 0.44904(12) 0.15992(11) 0.52775(10) 0.0508 1.0000 Uiso R . . . . . H151 H 0.36880(11) 0.39886(10) 0.48456(8) 0.0384 1.0000 Uiso R . . . . . H161 H 0.31392(13) 0.26651(11) 0.58483(9) 0.0453 1.0000 Uiso R . . . . . H162 H 0.41220(13) 0.31157(11) 0.58139(9) 0.0453 1.0000 Uiso R . . . . . H191 H 0.21153(13) 0.29242(12) 0.65717(9) 0.0512 1.0000 Uiso R . . . . . H201 H 0.06596(15) 0.30618(14) 0.70317(10) 0.0654 1.0000 Uiso R . . . . . H211 H -0.01798(13) 0.43542(14) 0.68675(10) 0.0615 1.0000 Uiso R . . . . . H221 H 0.04521(12) 0.55366(13) 0.62462(9) 0.0533 1.0000 Uiso R . . . . . H231 H 0.19004(11) 0.54051(11) 0.57732(9) 0.0430 1.0000 Uiso R . . . . . H251 H 0.36757(12) 0.54831(12) 0.51218(10) 0.0503 1.0000 Uiso R . . . . . H261 H 0.45597(13) 0.66807(12) 0.55037(11) 0.0598 1.0000 Uiso R . . . . . H271 H 0.50248(12) 0.67442(12) 0.66547(11) 0.0546 1.0000 Uiso R . . . . . H281 H 0.46654(12) 0.55890(12) 0.74050(10) 0.0507 1.0000 Uiso R . . . . . H291 H 0.37931(11) 0.43861(11) 0.70257(9) 0.0428 1.0000 Uiso R . . . . . H331 H 0.11092(13) 0.05872(14) 0.31477(11) 0.0651 1.0000 Uiso R . . . . . H332 H 0.04743(13) 0.14192(14) 0.33297(11) 0.0651 1.0000 Uiso R . . . . . H333 H 0.07972(13) 0.07561(14) 0.39274(11) 0.0651 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 O2 0.0525(8) 0.0566(8) 0.0325(6) 0.0008(6) 0.0052(6) 0.0050(6) O10 0.0501(8) 0.0487(8) 0.0447(7) -0.0120(6) -0.0009(6) 0.0127(6) O12 0.0438(7) 0.0371(7) 0.0529(8) 0.0111(6) -0.0013(6) -0.0036(6) O13 0.0311(6) 0.0349(6) 0.0384(6) 0.0003(5) -0.0030(5) 0.0026(5) O31 0.0318(7) 0.0672(9) 0.0658(9) -0.0213(7) 0.0083(6) -0.0074(6) O32 0.0397(7) 0.0462(7) 0.0522(8) -0.0164(6) 0.0016(6) -0.0110(6) C1 0.0535(11) 0.0491(10) 0.0401(10) 0.0077(9) 0.0022(8) 0.0044(9) C3 0.0319(8) 0.0473(11) 0.0333(9) -0.0046(8) -0.0008(7) -0.0014(8) C4 0.0294(8) 0.0320(8) 0.0328(8) -0.0015(7) -0.0009(7) -0.0005(7) C5 0.0293(8) 0.0303(8) 0.0320(8) -0.0019(7) -0.0003(7) -0.0010(7) C6 0.0316(8) 0.0332(8) 0.0327(8) -0.0040(7) -0.0003(7) 0.0009(7) C7 0.0394(9) 0.0350(9) 0.0455(10) -0.0065(8) -0.0035(8) 0.0079(8) C8 0.0436(10) 0.0360(9) 0.0456(10) 0.0019(8) -0.0059(8) 0.0076(8) C9 0.0359(9) 0.0387(9) 0.0357(9) 0.0026(8) -0.0034(7) 0.0018(8) C11 0.0342(8) 0.0284(8) 0.0332(8) -0.0055(7) -0.0004(7) -0.0021(7) C14 0.0387(10) 0.0420(10) 0.0500(11) 0.0009(8) -0.0075(8) 0.0087(8) C15 0.0340(8) 0.0327(9) 0.0329(8) -0.0041(7) -0.0005(7) 0.0009(7) C16 0.0443(10) 0.0315(8) 0.0414(9) -0.0030(7) -0.0076(8) 0.0041(8) C17 0.0375(9) 0.0283(8) 0.0310(8) -0.0014(7) -0.0004(7) 0.0010(7) C18 0.0375(9) 0.0340(9) 0.0278(8) -0.0036(7) -0.0021(7) -0.0054(7) C19 0.0577(12) 0.0364(10) 0.0383(9) 0.0006(8) 0.0050(9) -0.0094(9) C20 0.0670(13) 0.0531(12) 0.0466(11) -0.0041(9) 0.0190(10) -0.0241(11) C21 0.0465(11) 0.0635(13) 0.0480(11) -0.0163(10) 0.0132(9) -0.0146(10) C22 0.0422(10) 0.0529(11) 0.0440(10) -0.0075(9) 0.0041(8) 0.0012(9) C23 0.0408(10) 0.0366(9) 0.0350(9) -0.0002(7) 0.0030(8) -0.0028(7) C24 0.0305(8) 0.0290(8) 0.0355(9) -0.0029(7) 0.0002(7) 0.0029(7) C25 0.0446(10) 0.0410(10) 0.0437(10) 0.0056(8) -0.0054(8) -0.0047(8) C26 0.0474(11) 0.0375(10) 0.0691(14) 0.0080(9) -0.0028(10) -0.0087(9) C27 0.0326(9) 0.0372(9) 0.0712(13) -0.0131(9) -0.0057(9) -0.0009(8) C28 0.0396(10) 0.0458(10) 0.0466(10) -0.0128(9) -0.0082(8) 0.0047(8) C29 0.0383(9) 0.0353(9) 0.0380(9) -0.0035(7) -0.0018(8) 0.0020(7) C30 0.0341(9) 0.0369(9) 0.0321(8) -0.0010(7) -0.0011(7) -0.0030(7) C33 0.0518(12) 0.0538(12) 0.0583(12) -0.0102(10) -0.0054(10) -0.0229(10) _refine_ls_extinction_method None 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 O2 . C1 . 1.464(2) yes O2 . C3 . 1.367(2) yes O10 . C3 . 1.196(2) yes O12 . C11 . 1.203(2) yes O13 . C11 . 1.3307(19) yes O13 . C14 . 1.452(2) yes O31 . C30 . 1.194(2) yes O32 . C30 . 1.331(2) yes O32 . C33 . 1.450(2) yes C1 . C9 . 1.519(2) yes C1 . H11 . 1.000 no C1 . H12 . 1.000 no C3 . C4 . 1.511(2) yes C4 . C5 . 1.525(2) yes C4 . C9 . 1.524(2) yes C4 . H41 . 1.000 no C5 . C6 . 1.576(2) yes C5 . C11 . 1.523(2) yes C5 . C30 . 1.534(2) yes C6 . C7 . 1.515(2) yes C6 . C15 . 1.524(2) yes C6 . H61 . 1.000 no C7 . C8 . 1.331(3) yes C7 . H71 . 1.000 no C8 . C9 . 1.495(2) yes C8 . H81 . 1.000 no C9 . H91 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 1.000 no C15 . C16 . 1.507(2) yes C15 . C17 . 1.534(2) yes C15 . H151 . 1.000 no C16 . C17 . 1.510(2) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 no C17 . C18 . 1.509(2) yes C17 . C24 . 1.508(2) yes C18 . C19 . 1.390(2) yes C18 . C23 . 1.395(2) yes C19 . C20 . 1.391(3) yes C19 . H191 . 1.000 no C20 . C21 . 1.373(3) yes C20 . H201 . 1.000 no C21 . C22 . 1.384(3) yes C21 . H211 . 1.000 no C22 . C23 . 1.389(3) yes C22 . H221 . 1.000 no C23 . H231 . 1.000 no C24 . C25 . 1.382(2) yes C24 . C29 . 1.397(2) yes C25 . C26 . 1.392(3) yes C25 . H251 . 1.000 no C26 . C27 . 1.383(3) yes C26 . H261 . 1.000 no C27 . C28 . 1.375(3) yes C27 . H271 . 1.000 no C28 . C29 . 1.388(3) yes C28 . H281 . 1.000 no C29 . H291 . 1.000 no C33 . H331 . 1.000 no C33 . H332 . 1.000 no C33 . H333 . 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 C1 . O2 . C3 . 110.34(13) yes C11 . O13 . C14 . 114.61(13) yes C30 . O32 . C33 . 115.45(14) yes O2 . C1 . C9 . 103.38(14) yes O2 . C1 . H11 . 111.007 no C9 . C1 . H11 . 110.952 no O2 . C1 . H12 . 110.969 no C9 . C1 . H12 . 110.964 no H11 . C1 . H12 . 109.467 no O2 . C3 . O10 . 121.19(16) yes O2 . C3 . C4 . 107.40(14) yes O10 . C3 . C4 . 131.34(16) yes C3 . C4 . C5 . 124.04(14) yes C3 . C4 . C9 . 101.91(13) yes C5 . C4 . C9 . 112.19(13) yes C3 . C4 . H41 . 105.371 no C5 . C4 . H41 . 106.027 no C9 . C4 . H41 . 105.953 no C4 . C5 . C6 . 107.37(12) yes C4 . C5 . C11 . 114.20(13) yes C6 . C5 . C11 . 109.49(12) yes C4 . C5 . C30 . 111.18(13) yes C6 . C5 . C30 . 108.64(12) yes C11 . C5 . C30 . 105.86(13) yes C5 . C6 . C7 . 111.98(13) yes C5 . C6 . C15 . 114.28(13) yes C7 . C6 . C15 . 108.09(13) yes C5 . C6 . H61 . 107.175 no C7 . C6 . H61 . 107.580 no C15 . C6 . H61 . 107.446 no C6 . C7 . C8 . 126.91(16) yes C6 . C7 . H71 . 116.546 no C8 . C7 . H71 . 116.548 no C7 . C8 . C9 . 120.09(16) yes C7 . C8 . H81 . 120.013 no C9 . C8 . H81 . 119.901 no C4 . C9 . C1 . 99.98(13) yes C4 . C9 . C8 . 109.78(14) yes C1 . C9 . C8 . 121.26(15) yes C4 . C9 . H91 . 108.363 no C1 . C9 . H91 . 108.158 no C8 . C9 . H91 . 108.534 no C5 . C11 . O13 . 112.94(14) yes C5 . C11 . O12 . 122.48(15) yes O13 . C11 . O12 . 124.57(15) yes O13 . C14 . H141 . 109.503 no O13 . C14 . H142 . 109.498 no H141 . C14 . H142 . 109.476 no O13 . C14 . H143 . 109.398 no H141 . C14 . H143 . 109.476 no H142 . C14 . H143 . 109.476 no C6 . C15 . C16 . 122.46(14) yes C6 . C15 . C17 . 120.01(14) yes C16 . C15 . C17 . 59.55(10) yes C6 . C15 . H151 . 114.594 no C16 . C15 . H151 . 114.753 no C17 . C15 . H151 . 114.474 no C15 . C16 . C17 . 61.12(11) yes C15 . C16 . H161 . 119.615 no C17 . C16 . H161 . 119.930 no C15 . C16 . H162 . 119.934 no C17 . C16 . H162 . 119.777 no H161 . C16 . H162 . 109.467 no C15 . C17 . C16 . 59.34(10) yes C15 . C17 . C18 . 119.86(13) yes C16 . C17 . C18 . 118.80(14) yes C15 . C17 . C24 . 117.84(14) yes C16 . C17 . C24 . 118.06(14) yes C18 . C17 . C24 . 113.03(13) yes C17 . C18 . C19 . 122.47(15) yes C17 . C18 . C23 . 119.49(15) yes C19 . C18 . C23 . 118.02(16) yes C18 . C19 . C20 . 120.53(18) yes C18 . C19 . H191 . 119.787 no C20 . C19 . H191 . 119.685 no C19 . C20 . C21 . 121.00(18) yes C19 . C20 . H201 . 119.609 no C21 . C20 . H201 . 119.395 no C20 . C21 . C22 . 119.20(18) yes C20 . C21 . H211 . 120.476 no C22 . C21 . H211 . 120.327 no C21 . C22 . C23 . 120.18(19) yes C21 . C22 . H221 . 119.886 no C23 . C22 . H221 . 119.936 no C18 . C23 . C22 . 121.06(17) yes C18 . C23 . H231 . 119.501 no C22 . C23 . H231 . 119.434 no C17 . C24 . C25 . 121.93(15) yes C17 . C24 . C29 . 119.15(15) yes C25 . C24 . C29 . 118.84(16) yes C24 . C25 . C26 . 120.93(17) yes C24 . C25 . H251 . 119.543 no C26 . C25 . H251 . 119.530 no C25 . C26 . C27 . 119.63(18) yes C25 . C26 . H261 . 120.250 no C27 . C26 . H261 . 120.120 no C26 . C27 . C28 . 120.05(17) yes C26 . C27 . H271 . 119.989 no C28 . C27 . H271 . 119.962 no C27 . C28 . C29 . 120.44(17) yes C27 . C28 . H281 . 119.864 no C29 . C28 . H281 . 119.695 no C24 . C29 . C28 . 120.11(17) yes C24 . C29 . H291 . 119.881 no C28 . C29 . H291 . 120.011 no C5 . C30 . O32 . 110.79(13) yes C5 . C30 . O31 . 125.68(15) yes O32 . C30 . O31 . 123.53(15) yes O32 . C33 . H331 . 109.544 no O32 . C33 . H332 . 109.373 no H331 . C33 . H332 . 109.475 no O32 . C33 . H333 . 109.484 no H331 . C33 . H333 . 109.475 no H332 . C33 . H333 . 109.476 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 O2 C19 3.586(2) . 5_554 no O10 C21 3.321(2) . 4_556 no O10 C29 3.556(2) . 5_554 no O12 C25 3.278(2) . 3_545 no O12 C23 3.351(2) . 3_545 no O12 C7 3.496(2) . 3_545 no O13 C26 3.551(2) . 2_666 no O31 C14 3.192(2) . 4_456 no O31 C26 3.530(3) . 3_545 no C14 C21 3.396(3) . 4_556 no C20 C33 3.475(3) . 5 no C28 C33 3.466(3) . 4_556 no C29 C33 3.372(3) . 4_556 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 O2 C1 C9 C4 . . . . 37.4(2) no O2 C1 C9 C8 . . . . 158.0(1) no O2 C3 C4 C5 . . . . 155.4(1) no O2 C3 C4 C9 . . . . 27.9(2) no O10 C3 O2 C1 . . . . 178.9(2) no O10 C3 C4 C5 . . . . -27.9(3) no O10 C3 C4 C9 . . . . -155.3(2) no O12 C11 O13 C14 . . . . -2.5(2) no O12 C11 C5 C4 . . . . -151.7(2) no O12 C11 C5 C6 . . . . 87.8(2) no O12 C11 C5 C30 . . . . -29.1(2) no O13 C11 C5 C4 . . . . 29.5(2) no O13 C11 C5 C6 . . . . -90.9(2) no O13 C11 C5 C30 . . . . 152.2(1) no O31 C30 O32 C33 . . . . -5.6(2) no O31 C30 C5 C4 . . . . -122.7(2) no O31 C30 C5 C6 . . . . -4.8(2) no O31 C30 C5 C11 . . . . 112.8(2) no O32 C30 C5 C4 . . . . 57.8(2) no O32 C30 C5 C6 . . . . 175.7(1) no O32 C30 C5 C11 . . . . -66.8(2) no C1 O2 C3 C4 . . . . -4.0(2) no C1 C9 C4 C3 . . . . -39.2(2) no C1 C9 C4 C5 . . . . -174.0(1) no C1 C9 C8 C7 . . . . -141.3(2) no C3 O2 C1 C9 . . . . -21.8(2) no C3 C4 C5 C6 . . . . 173.8(1) no C3 C4 C5 C11 . . . . 52.2(2) no C3 C4 C5 C30 . . . . -67.5(2) no C3 C4 C9 C8 . . . . -167.8(1) no C4 C5 C6 C7 . . . . 37.0(2) no C4 C5 C6 C15 . . . . -86.3(2) no C4 C9 C8 C7 . . . . -25.6(2) no C5 C4 C9 C8 . . . . 57.5(2) no C5 C6 C7 C8 . . . . -8.7(2) no C5 C6 C15 C16 . . . . -77.2(2) no C5 C6 C15 C17 . . . . -148.1(1) no C5 C11 O13 C14 . . . . 176.1(1) no C5 C30 O32 C33 . . . . 173.9(1) no C6 C5 C4 C9 . . . . -63.2(2) no C6 C7 C8 C9 . . . . 2.6(3) no C6 C15 C16 C17 . . . . -108.3(2) no C6 C15 C17 C16 . . . . 112.3(2) no C6 C15 C17 C18 . . . . 4.5(2) no C6 C15 C17 C24 . . . . -139.9(1) no C7 C6 C5 C11 . . . . 161.5(1) no C7 C6 C5 C30 . . . . -83.4(2) no C7 C6 C15 C16 . . . . 157.4(2) no C7 C6 C15 C17 . . . . 86.5(2) no C8 C7 C6 C15 . . . . 118.0(2) no C9 C4 C5 C11 . . . . 175.2(1) no C9 C4 C5 C30 . . . . 55.5(2) no C11 C5 C6 C15 . . . . 38.1(2) no C15 C6 C5 C30 . . . . 153.3(1) no C15 C16 C17 C18 . . . . 109.5(2) no C15 C16 C17 C24 . . . . -107.4(2) no C15 C17 C18 C19 . . . . 90.0(2) no C15 C17 C18 C23 . . . . -92.1(2) no C15 C17 C24 C25 . . . . 40.3(2) no C15 C17 C24 C29 . . . . -143.2(2) no C16 C15 C17 C18 . . . . -107.8(2) no C16 C15 C17 C24 . . . . 107.8(2) no C16 C17 C18 C19 . . . . 20.8(2) no C16 C17 C18 C23 . . . . -161.2(2) no C16 C17 C24 C25 . . . . 108.4(2) no C16 C17 C24 C29 . . . . -75.0(2) no C17 C18 C19 C20 . . . . 179.4(2) no C17 C18 C23 C22 . . . . -179.2(2) no C17 C24 C25 C26 . . . . 176.4(2) no C17 C24 C29 C28 . . . . -176.3(2) no C18 C17 C24 C25 . . . . -106.5(2) no C18 C17 C24 C29 . . . . 70.0(2) no C18 C19 C20 C21 . . . . -0.5(3) no C18 C23 C22 C21 . . . . 0.0(3) no C19 C18 C17 C24 . . . . -124.0(2) no C19 C18 C23 C22 . . . . -1.2(3) no C19 C20 C21 C22 . . . . -0.7(3) no C20 C19 C18 C23 . . . . 1.5(3) no C20 C21 C22 C23 . . . . 1.0(3) no C23 C18 C17 C24 . . . . 53.9(2) no C24 C25 C26 C27 . . . . -0.5(3) no C24 C29 C28 C27 . . . . 0.1(3) no C25 C24 C29 C28 . . . . 0.4(3) no C25 C26 C27 C28 . . . . 1.1(3) no C26 C25 C24 C29 . . . . -0.2(3) no C26 C27 C28 C29 . . . . -0.9(3) no #------------------------------------------------------------------------------ #===END data_mss041 _database_code_depnum_ccdc_archive 'CCDC 644830' _audit_creation_date 04-14-04 _audit_creation_method CRYSTALS_ver_12-03-99 # 4131751 mss041 _audit_update_record ; 2004-04-14 - Report on C25 H24 O4 by Anthony C. Willis for Regis Tripoli and Mick Sherburn 2004-04-14 - passes checkcif tests with minor warnings ; #============================================================================= # 4. TEXT _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 11.0190(4) _cell_angle_alpha 90 _cell_length_b 7.6264(3) _cell_angle_beta 91.3965(17) _cell_length_c 12.1306(5) _cell_angle_gamma 90 _cell_volume 1019.10(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration unk _refine_ls_abs_structure_details ; Not determined. The enantiomer has been assigned arbitrarily. ; 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_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C25 H24 O4 ' _chemical_formula_moiety ' C25 H24 O4 ' _chemical_compound_source ; ? ; _chemical_formula_weight 388.46 _cell_measurement_reflns_used 38388 _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 0.14 _exptl_crystal_size_max 0.26 _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.085 _diffrn_measurement_device_type ; Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 1.0 deg at rate 180 sec/frame, crystal-detector distance 32mm, multiple scan sets so over 95 percent of data collected with 2-fold redundancy or more [assuming Friedel Law]. ; # 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 0.020 -1 0 0 0.030 0 1 0 0.120 0 0 1 0.060 0 0 -1 0.080 0 1 -2 0.090 0 1 3 0.068 0 -3 2 0.134 0 -1 -1 0.155 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.983 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.048 # Sheldrick geometric definitions 0.99 1.00 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 200 _diffrn_reflns_number 12952 _reflns_number_total 1943 _diffrn_reflns_av_R_equivalents 0.03 # Number of reflections with Friedels Law is 1943 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1807 _diffrn_reflns_theta_min 3.155 _diffrn_reflns_theta_max 25.061 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.061 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _refine_diff_density_min -0.15 _refine_diff_density_max 0.14 _refine_ls_number_reflns 1460 _refine_ls_number_restraints 0 _refine_ls_number_parameters 262 #_refine_ls_R_factor_ref 0.0353 _refine_ls_wR_factor_ref 0.0391 _refine_ls_goodness_of_fit_ref 1.0875 #_reflns_number_all 1460 _refine_ls_R_factor_all 0.0353 _refine_ls_wR_factor_all 0.0391 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.5u(I) _reflns_number_gt 1460 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_gt 0.0391 _refine_ls_shift/su_max 0.000197 _refine_ls_structure_factor_coef F _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: 0.527 0.278 0.218 ; _refine_ls_extinction_method None _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order 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 O2 O 0.6669(2) 0.1496(4) 0.4334(2) 0.0630 1.0000 Uani . . . . . . O10 O 0.5204(3) -0.0523(4) 0.4175(2) 0.0644 1.0000 Uani . . . . . . O12 O 0.3673(2) 0.1220(4) 0.07235(19) 0.0618 1.0000 Uani . . . . . . O13 O 0.5284(2) 0.0302(3) 0.17161(17) 0.0537 1.0000 Uani . . . . . . C1 C 0.6847(3) 0.3334(6) 0.4023(3) 0.0581 1.0000 Uani . . . . . . C3 C 0.5543(3) 0.0937(5) 0.3996(3) 0.0530 1.0000 Uani . . . . . . C4 C 0.4895(3) 0.2459(5) 0.3455(2) 0.0403 1.0000 Uani . . . . . . C5 C 0.3904(3) 0.2234(4) 0.2590(2) 0.0375 1.0000 Uani . . . . . . C6 C 0.3412(3) 0.4081(4) 0.2261(3) 0.0392 1.0000 Uani . . . . . . C7 C 0.4343(3) 0.5526(5) 0.2388(3) 0.0492 1.0000 Uani . . . . . . C8 C 0.5482(3) 0.5350(5) 0.2757(3) 0.0515 1.0000 Uani . . . . . . C9 C 0.5940(3) 0.3569(5) 0.3061(3) 0.0454 1.0000 Uani . . . . . . C11 C 0.4263(3) 0.1227(4) 0.1571(3) 0.0415 1.0000 Uani . . . . . . C14 C 0.5659(4) -0.0733(5) 0.0778(3) 0.0609 1.0000 Uani . . . . . . C15 C 0.2285(3) 0.4584(4) 0.2890(3) 0.0389 1.0000 Uani . . . . . . C16 C 0.1100(3) 0.3670(4) 0.2639(3) 0.0426 1.0000 Uani . . . . . . C17 C 0.1256(3) 0.5568(4) 0.2313(2) 0.0381 1.0000 Uani . . . . . . C18 C 0.0601(3) 0.6927(4) 0.2969(2) 0.0386 1.0000 Uani . . . . . . C19 C 0.1237(3) 0.8225(5) 0.3546(3) 0.0489 1.0000 Uani . . . . . . C20 C 0.0627(4) 0.9515(5) 0.4132(3) 0.0581 1.0000 Uani . . . . . . C21 C -0.0632(4) 0.9496(5) 0.4150(3) 0.0598 1.0000 Uani . . . . . . C22 C -0.1273(3) 0.8213(5) 0.3589(3) 0.0572 1.0000 Uani . . . . . . C23 C -0.0665(3) 0.6936(5) 0.2993(3) 0.0475 1.0000 Uani . . . . . . C24 C 0.1357(3) 0.6014(4) 0.1100(2) 0.0372 1.0000 Uani . . . . . . C25 C 0.1944(3) 0.7551(4) 0.0784(2) 0.0411 1.0000 Uani . . . . . . C26 C 0.2060(3) 0.7975(5) -0.0325(3) 0.0465 1.0000 Uani . . . . . . C27 C 0.1568(3) 0.6888(5) -0.1130(3) 0.0485 1.0000 Uani . . . . . . C28 C 0.0961(3) 0.5389(6) -0.0837(3) 0.0518 1.0000 Uani . . . . . . C29 C 0.0863(3) 0.4941(5) 0.0275(3) 0.0452 1.0000 Uani . . . . . . H11 H 0.7697(3) 0.3542(6) 0.3784(3) 0.0698 1.0000 Uiso R . . . . . H12 H 0.6659(3) 0.4142(6) 0.4645(3) 0.0698 1.0000 Uiso R . . . . . H41 H 0.4528(3) 0.3145(5) 0.4066(2) 0.0486 1.0000 Uiso R . . . . . H51 H 0.3265(3) 0.1491(4) 0.2930(2) 0.0452 1.0000 Uiso R . . . . . H61 H 0.3196(3) 0.3963(4) 0.1459(3) 0.0470 1.0000 Uiso R . . . . . H71 H 0.4075(3) 0.6734(5) 0.2173(3) 0.0589 1.0000 Uiso R . . . . . H81 H 0.6024(3) 0.6397(5) 0.2832(3) 0.0621 1.0000 Uiso R . . . . . H91 H 0.6334(3) 0.3084(5) 0.2392(3) 0.0546 1.0000 Uiso R . . . . . H141 H 0.6429(4) -0.1368(5) 0.0972(3) 0.0739 1.0000 Uiso R . . . . . H142 H 0.5795(4) 0.0060(5) 0.0136(3) 0.0739 1.0000 Uiso R . . . . . H143 H 0.5010(4) -0.1602(5) 0.0579(3) 0.0739 1.0000 Uiso R . . . . . H151 H 0.2519(3) 0.4878(4) 0.3670(3) 0.0467 1.0000 Uiso R . . . . . H161 H 0.0549(3) 0.3355(4) 0.3251(3) 0.0509 1.0000 Uiso R . . . . . H162 H 0.1057(3) 0.2739(4) 0.2058(3) 0.0509 1.0000 Uiso R . . . . . H191 H 0.2144(3) 0.8233(5) 0.3540(3) 0.0590 1.0000 Uiso R . . . . . H201 H 0.1094(4) 1.0448(5) 0.4536(3) 0.0695 1.0000 Uiso R . . . . . H211 H -0.1075(4) 1.0413(5) 0.4572(3) 0.0714 1.0000 Uiso R . . . . . H221 H -0.2180(3) 0.8198(5) 0.3608(3) 0.0689 1.0000 Uiso R . . . . . H231 H -0.1140(3) 0.6019(5) 0.2580(3) 0.0570 1.0000 Uiso R . . . . . H251 H 0.2286(3) 0.8359(4) 0.1361(2) 0.0495 1.0000 Uiso R . . . . . H261 H 0.2498(3) 0.9066(5) -0.0539(3) 0.0556 1.0000 Uiso R . . . . . H271 H 0.1651(3) 0.7193(5) -0.1926(3) 0.0584 1.0000 Uiso R . . . . . H281 H 0.0592(3) 0.4615(6) -0.1420(3) 0.0620 1.0000 Uiso R . . . . . H291 H 0.0435(3) 0.3837(5) 0.0480(3) 0.0543 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 O2 0.0556(16) 0.077(2) 0.0558(14) 0.0067(14) -0.0087(12) 0.0209(14) O10 0.0875(19) 0.0513(17) 0.0545(15) 0.0177(14) 0.0087(13) 0.0177(16) O12 0.0788(17) 0.0553(16) 0.0505(14) -0.0115(13) -0.0129(13) 0.0029(14) O13 0.0610(15) 0.0559(15) 0.0446(12) -0.0088(13) 0.0095(11) 0.0117(13) C1 0.050(2) 0.069(3) 0.055(2) -0.008(2) -0.0066(16) 0.007(2) C3 0.063(2) 0.058(2) 0.0389(18) 0.0049(17) 0.0070(16) 0.020(2) C4 0.0471(17) 0.0400(17) 0.0336(15) -0.0005(14) 0.0024(13) 0.0076(15) C5 0.0409(16) 0.0340(17) 0.0379(15) 0.0024(14) 0.0066(12) 0.0015(14) C6 0.0400(17) 0.0363(17) 0.0414(17) 0.0030(14) 0.0018(13) 0.0032(14) C7 0.0498(19) 0.0352(18) 0.063(2) 0.0096(18) 0.0041(16) -0.0006(16) C8 0.049(2) 0.0400(19) 0.066(2) 0.0028(18) -0.0002(16) -0.0078(17) C9 0.0416(18) 0.050(2) 0.0448(18) -0.0016(16) 0.0015(14) 0.0034(17) C11 0.0507(18) 0.0307(16) 0.0433(17) 0.0033(15) 0.0053(14) -0.0032(16) C14 0.073(2) 0.055(2) 0.055(2) -0.0167(19) 0.0212(18) 0.001(2) C15 0.0405(16) 0.0381(17) 0.0381(15) 0.0006(14) -0.0005(13) 0.0045(14) C16 0.0412(18) 0.0406(19) 0.0460(18) 0.0036(16) 0.0037(14) -0.0031(15) C17 0.0378(15) 0.0355(17) 0.0408(16) -0.0009(14) -0.0002(13) 0.0014(14) C18 0.0458(17) 0.0365(17) 0.0337(15) 0.0055(13) 0.0043(13) 0.0045(15) C19 0.058(2) 0.046(2) 0.0421(17) -0.0028(16) -0.0020(15) 0.0094(17) C20 0.078(3) 0.046(2) 0.050(2) -0.0048(18) -0.0048(18) 0.012(2) C21 0.077(3) 0.058(2) 0.0454(19) 0.0030(19) 0.0130(18) 0.026(2) C22 0.054(2) 0.059(2) 0.059(2) 0.011(2) 0.0149(17) 0.015(2) C23 0.0456(18) 0.049(2) 0.0484(18) 0.0085(17) 0.0048(14) 0.0021(17) C24 0.0358(15) 0.0399(17) 0.0359(15) 0.0015(14) 0.0004(12) 0.0029(14) C25 0.0449(17) 0.0382(17) 0.0402(16) 0.0011(15) -0.0013(13) -0.0007(15) C26 0.0447(18) 0.048(2) 0.0473(18) 0.0081(17) 0.0016(14) -0.0004(16) C27 0.0443(18) 0.062(2) 0.0388(16) -0.0021(17) 0.0017(14) 0.0017(18) C28 0.0487(19) 0.063(2) 0.0434(19) -0.0079(19) -0.0009(14) -0.0044(19) C29 0.0450(18) 0.048(2) 0.0428(17) -0.0049(16) 0.0028(14) -0.0077(15) 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 O2 . C1 . 1.466(5) yes O2 . C3 . 1.367(5) yes O10 . C3 . 1.196(5) yes O12 . C11 . 1.203(4) yes O13 . C11 . 1.336(4) yes O13 . C14 . 1.454(4) yes C1 . C9 . 1.529(5) yes C1 . H11 . 1.000 no C1 . H12 . 1.000 no C3 . C4 . 1.505(5) yes C4 . C5 . 1.506(4) yes C4 . C9 . 1.516(5) yes C4 . H41 . 1.000 no C5 . C6 . 1.557(4) yes C5 . C11 . 1.515(4) yes C5 . H51 . 1.000 no C6 . C7 . 1.511(5) yes C6 . C15 . 1.523(4) yes C6 . H61 . 1.000 no C7 . C8 . 1.329(5) yes C7 . H71 . 1.000 no C8 . C9 . 1.492(5) yes C8 . H81 . 1.000 no C9 . H91 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 1.000 no C15 . C16 . 1.505(4) yes C15 . C17 . 1.517(4) yes C15 . H151 . 1.000 no C16 . C17 . 1.512(4) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 no C17 . C18 . 1.502(4) yes C17 . C24 . 1.516(4) yes C18 . C19 . 1.392(5) yes C18 . C23 . 1.396(4) yes C19 . C20 . 1.395(5) yes C19 . H191 . 1.000 no C20 . C21 . 1.388(5) yes C20 . H201 . 1.000 no C21 . C22 . 1.377(6) yes C21 . H211 . 1.000 no C22 . C23 . 1.393(5) yes C22 . H221 . 1.000 no C23 . H231 . 1.000 no C24 . C25 . 1.397(4) yes C24 . C29 . 1.393(4) yes C25 . C26 . 1.392(4) yes C25 . H251 . 1.000 no C26 . C27 . 1.381(5) yes C26 . H261 . 1.000 no C27 . C28 . 1.376(5) yes C27 . H271 . 1.000 no C28 . C29 . 1.398(5) yes C28 . H281 . 1.000 no C29 . H291 . 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 C1 . O2 . C3 . 110.3(3) yes C11 . O13 . C14 . 116.0(3) yes O2 . C1 . C9 . 102.7(3) yes O2 . C1 . H11 . 111.017 no C9 . C1 . H11 . 111.037 no O2 . C1 . H12 . 111.318 no C9 . C1 . H12 . 111.144 no H11 . C1 . H12 . 109.467 no O2 . C3 . O10 . 121.4(3) yes O2 . C3 . C4 . 107.9(3) yes O10 . C3 . C4 . 130.6(4) yes C3 . C4 . C5 . 122.9(3) yes C3 . C4 . C9 . 102.3(3) yes C5 . C4 . C9 . 112.8(3) yes C3 . C4 . H41 . 106.057 no C5 . C4 . H41 . 106.049 no C9 . C4 . H41 . 105.412 no C4 . C5 . C6 . 108.5(3) yes C4 . C5 . C11 . 115.3(3) yes C6 . C5 . C11 . 110.2(2) yes C4 . C5 . H51 . 106.467 no C6 . C5 . H51 . 111.950 no C11 . C5 . H51 . 104.442 no C5 . C6 . C7 . 113.8(3) yes C5 . C6 . C15 . 112.5(3) yes C7 . C6 . C15 . 109.0(3) yes C5 . C6 . H61 . 103.958 no C7 . C6 . H61 . 108.020 no C15 . C6 . H61 . 109.409 no C6 . C7 . C8 . 126.4(3) yes C6 . C7 . H71 . 116.746 no C8 . C7 . H71 . 116.850 no C7 . C8 . C9 . 119.1(3) yes C7 . C8 . H81 . 120.458 no C9 . C8 . H81 . 120.457 no C1 . C9 . C4 . 100.4(3) yes C1 . C9 . C8 . 120.4(3) yes C4 . C9 . C8 . 109.4(3) yes C1 . C9 . H91 . 106.669 no C4 . C9 . H91 . 113.430 no C8 . C9 . H91 . 106.718 no C5 . C11 . O13 . 113.3(3) yes C5 . C11 . O12 . 123.6(3) yes O13 . C11 . O12 . 123.0(3) yes O13 . C14 . H141 . 109.509 no O13 . C14 . H142 . 109.403 no H141 . C14 . H142 . 109.476 no O13 . C14 . H143 . 109.488 no H141 . C14 . H143 . 109.476 no H142 . C14 . H143 . 109.476 no C6 . C15 . C16 . 119.8(3) yes C6 . C15 . C17 . 120.2(3) yes C16 . C15 . C17 . 60.0(2) yes C6 . C15 . H151 . 109.587 no C16 . C15 . H151 . 119.899 no C17 . C15 . H151 . 119.920 no C15 . C16 . C17 . 60.4(2) yes C15 . C16 . H161 . 120.022 no C17 . C16 . H161 . 119.966 no C15 . C16 . H162 . 119.829 no C17 . C16 . H162 . 119.929 no H161 . C16 . H162 . 109.467 no C15 . C17 . C16 . 59.6(2) yes C15 . C17 . C18 . 117.4(3) yes C16 . C17 . C18 . 117.6(3) yes C15 . C17 . C24 . 119.1(3) yes C16 . C17 . C24 . 118.7(3) yes C18 . C17 . C24 . 114.0(2) yes C17 . C18 . C19 . 121.0(3) yes C17 . C18 . C23 . 120.5(3) yes C19 . C18 . C23 . 118.5(3) yes C18 . C19 . C20 . 121.0(3) yes C18 . C19 . H191 . 119.460 no C20 . C19 . H191 . 119.561 no C19 . C20 . C21 . 119.7(4) yes C19 . C20 . H201 . 120.175 no C21 . C20 . H201 . 120.168 no C20 . C21 . C22 . 120.0(3) yes C20 . C21 . H211 . 120.055 no C22 . C21 . H211 . 119.954 no C21 . C22 . C23 . 120.4(3) yes C21 . C22 . H221 . 119.810 no C23 . C22 . H221 . 119.790 no C18 . C23 . C22 . 120.5(4) yes C18 . C23 . H231 . 119.790 no C22 . C23 . H231 . 119.744 no C17 . C24 . C25 . 120.0(3) yes C17 . C24 . C29 . 121.9(3) yes C25 . C24 . C29 . 118.1(3) yes C24 . C25 . C26 . 120.9(3) yes C24 . C25 . H251 . 119.559 no C26 . C25 . H251 . 119.493 no C25 . C26 . C27 . 120.0(3) yes C25 . C26 . H261 . 120.015 no C27 . C26 . H261 . 119.992 no C26 . C27 . C28 . 120.1(3) yes C26 . C27 . H271 . 119.970 no C28 . C27 . H271 . 119.946 no C27 . C28 . C29 . 120.1(3) yes C27 . C28 . H281 . 119.997 no C29 . C28 . H281 . 119.916 no C28 . C29 . C24 . 120.8(3) yes C28 . C29 . H291 . 119.599 no C24 . C29 . H291 . 119.604 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 O2 C21 3.355(5) . 1_645 no O2 C22 3.511(4) . 1_645 no O2 O10 3.589(4) . 2_656 no O10 C4 3.265(4) . 2_646 no O10 C1 3.299(5) . 2_646 no O12 C14 3.054(5) . 2_655 no O12 C26 3.285(4) . 1_545 no O12 C25 3.387(4) . 1_545 no C1 C19 3.586(5) . 2_646 no C26 C29 3.555(5) . 2 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 O2 C1 C9 C4 . . . . 37.4(3) no O2 C1 C9 C8 . . . . 157.3(3) no O2 C3 C4 C5 . . . . 153.7(3) no O2 C3 C4 C9 . . . . 25.8(3) no O10 C3 O2 C1 . . . . -179.3(3) no O10 C3 C4 C5 . . . . -28.9(6) no O10 C3 C4 C9 . . . . -156.8(4) no O12 C11 O13 C14 . . . . 0.2(5) no O12 C11 C5 C4 . . . . -165.0(3) no O12 C11 C5 C6 . . . . -41.8(4) no O13 C11 C5 C4 . . . . 16.9(4) no O13 C11 C5 C6 . . . . 140.1(3) no C1 O2 C3 C4 . . . . -1.6(4) no C1 C9 C4 C3 . . . . -38.1(3) no C1 C9 C4 C5 . . . . -172.2(3) no C1 C9 C8 C7 . . . . -145.0(4) no C3 O2 C1 C9 . . . . -23.1(3) no C3 C4 C5 C6 . . . . 177.5(3) no C3 C4 C5 C11 . . . . -58.4(4) no C3 C4 C9 C8 . . . . -165.7(3) no C4 C5 C6 C7 . . . . 28.8(4) no C4 C5 C6 C15 . . . . -95.7(3) no C4 C9 C8 C7 . . . . -29.6(5) no C5 C4 C9 C8 . . . . 60.2(4) no C5 C6 C7 C8 . . . . -1.1(5) no C5 C6 C15 C16 . . . . -70.9(4) no C5 C6 C15 C17 . . . . -141.5(3) no C5 C11 O13 C14 . . . . 178.3(3) no C6 C5 C4 C9 . . . . -59.3(4) no C6 C7 C8 C9 . . . . 1.6(6) no C6 C15 C16 C17 . . . . -109.8(3) no C6 C15 C17 C16 . . . . 109.1(3) no C6 C15 C17 C18 . . . . -143.4(3) no C6 C15 C17 C24 . . . . 1.0(4) no C7 C6 C5 C11 . . . . -98.3(3) no C7 C6 C15 C16 . . . . 162.0(3) no C7 C6 C15 C17 . . . . 91.4(4) no C8 C7 C6 C15 . . . . 125.2(4) no C9 C4 C5 C11 . . . . 64.8(4) no C11 C5 C6 C15 . . . . 137.2(3) no C15 C16 C17 C18 . . . . -107.2(3) no C15 C16 C17 C24 . . . . 108.8(3) no C15 C17 C18 C19 . . . . 51.0(4) no C15 C17 C18 C23 . . . . -130.4(3) no C15 C17 C24 C25 . . . . -86.4(4) no C15 C17 C24 C29 . . . . 94.5(4) no C16 C15 C17 C18 . . . . 107.5(3) no C16 C15 C17 C24 . . . . -108.1(3) no C16 C17 C18 C19 . . . . 119.2(3) no C16 C17 C18 C23 . . . . -62.2(4) no C16 C17 C24 C25 . . . . -155.6(3) no C16 C17 C24 C29 . . . . 25.3(5) no C17 C18 C19 C20 . . . . 178.3(3) no C17 C18 C23 C22 . . . . -179.1(3) no C17 C24 C25 C26 . . . . 179.2(3) no C17 C24 C29 C28 . . . . 179.5(3) no C18 C17 C24 C25 . . . . 59.2(4) no C18 C17 C24 C29 . . . . -119.9(3) no C18 C19 C20 C21 . . . . 0.6(5) no C18 C23 C22 C21 . . . . 0.9(5) no C19 C18 C17 C24 . . . . -95.2(3) no C19 C18 C23 C22 . . . . -0.4(5) no C19 C20 C21 C22 . . . . -0.2(6) no C20 C19 C18 C23 . . . . -0.3(5) no C20 C21 C22 C23 . . . . -0.5(6) no C23 C18 C17 C24 . . . . 83.4(4) no C24 C25 C26 C27 . . . . 1.4(5) no C24 C29 C28 C27 . . . . 1.1(5) no C25 C24 C29 C28 . . . . 0.4(5) no C25 C26 C27 C28 . . . . 0.2(5) no C26 C25 C24 C29 . . . . -1.7(5) no C26 C27 C28 C29 . . . . -1.4(5) no