# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Martin Banwell' _publ_contact_author_email MGB@RSC.ANU.EDU.AU _publ_section_title ; Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks ; loop_ _publ_author_name 'Martin Banwell' 'Kerrie A.B Austin' 'Jon D. Elsworth' 'Anthony C Willis' data_ban0629 _database_code_depnum_ccdc_archive 'CCDC 747028' _audit_creation_date 06-09-22 _audit_creation_method CRYSTALS_ver_12.18 _audit_update_record ; 2006-09-22 - Report on C14 H18 O3 by Anthony C. Willis for Kerrie Austin and Martin Banwell 2006-09-22 - passes checkcif tests with minor warnings ; _oxford_structure_analysis_title '9221409 ban0629' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.3882(1) _cell_length_b 10.3973(2) _cell_length_c 18.3495(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1218.77(4) _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 = C14 H18 O3 # Dc = 1.28 Fooo = 504.00 Mu = 0.89 M = 234.30 # Found Formula = C14 H18 O3 # Dc = 1.28 FOOO = 504.00 Mu = 0.89 M = 234.30 _chemical_formula_sum 'C14 H18 O3' _chemical_formula_moiety 'C14 H18 O3' _chemical_compound_source local _chemical_formula_weight 234.30 _cell_measurement_reflns_used 14878 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 200 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_max 0.44 _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.089 # 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 0.200 -1 0 0 0.220 0 1 0 0.100 0 -1 0 0.130 0 0 1 0.080 0 0 -1 0.070 0 -1 -2 0.095 0 1 2 0.090 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.031 # 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 1.8 deg at rate 108 sec/frame, crystal-detector distance 32mm, 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 ' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _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 21975 _reflns_number_total 1631 _diffrn_reflns_av_R_equivalents 0.038 # Number of reflections with Friedels Law is 1631 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1400 _diffrn_reflns_theta_min 2.961 _diffrn_reflns_theta_max 27.503 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.503 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _oxford_diffrn_Wilson_B_factor 2.79 _oxford_diffrn_Wilson_scale 0.71 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.11 _refine_diff_density_max 0.20 _refine_ls_number_reflns 1293 _refine_ls_number_restraints 0 _refine_ls_number_parameters 154 #_refine_ls_R_factor_ref 0.0258 _refine_ls_wR_factor_ref 0.0301 _refine_ls_goodness_of_fit_ref 1.1495 #_reflns_number_all 1627 _refine_ls_R_factor_all 0.0331 _refine_ls_wR_factor_all 0.0346 # 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 1293 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_gt 0.0301 _refine_ls_shift/su_max 0.000122 # 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 syn _refine_ls_abs_structure_details ; The enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure. ; _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, (Carruthers & Watkin, 1979, 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: 0.536 0.170 0.290 ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~14~H~18~O~3~ is reported. ; _publ_section_comment #Text of the paper ; The compound is enantiometrically pure but the anomolous dispersion terms are very low for all elements in the structure and so the absolute configuration was not determined in this experiment. Friedel-pair reflections have been averaged. The absolute configuration of the molecule has been assigned on the basis of the synthetic precursors. The crystallographic asymmetric unit consists of one molecule of C~14~H~18~O~3~. Hydrogen atoms were included at idealized positions with the methyl groups oriented to best-fit peaks in difference electron density maps. During refinement the H atoms ride on the atoms to which they were bonded. The final difference electron density map is essentially featureless, with the largest peaks being located between atoms. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; Hydrogen atoms were included at idealized positions and ride on the atoms to which they were bonded. ; _publ_section_exptl_prep ; The compound was prepared by KAA and recrystallized from dichloromethane/hexanes. The sample ID is KATV-02-81b. ; #**************************************************************************** # Insert your own references if required - in alphabetical order _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Carruthers, J.R. & Watkin, D.J. (1979), Acta Cryst. A35, 698-699. Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 0.8282(2) 0.32825(12) -0.01687(6) 0.0418 1.0000 Uani . . . . . . O2 O 0.74065(18) 0.23780(9) 0.30129(5) 0.0328 1.0000 Uani . . . . . . O3 O 0.78869(19) 0.45075(10) 0.32191(5) 0.0363 1.0000 Uani . . . . . . C1 C 0.7833(2) 0.27769(15) 0.04051(7) 0.0320 1.0000 Uani . . . . . . C2 C 0.8125(3) 0.13613(15) 0.05882(8) 0.0353 1.0000 Uani . . . . . . C3 C 0.7470(3) 0.12330(13) 0.13930(8) 0.0316 1.0000 Uani . . . . . . C4 C 0.7826(2) 0.25920(13) 0.16907(7) 0.0269 1.0000 Uani . . . . . . C5 C 0.6624(2) 0.29954(14) 0.23724(7) 0.0279 1.0000 Uani . . . . . . C6 C 0.7001(3) 0.44524(13) 0.25067(7) 0.0315 1.0000 Uani . . . . . . C7 C 0.8532(3) 0.50012(15) 0.19379(8) 0.0358 1.0000 Uani . . . . . . C8 C 1.0456(3) 0.41786(17) 0.19193(8) 0.0381 1.0000 Uani . . . . . . C9 C 1.0105(2) 0.29425(16) 0.17880(8) 0.0330 1.0000 Uani . . . . . . C10 C 0.7426(3) 0.48720(14) 0.11874(9) 0.0406 1.0000 Uani . . . . . . C11 C 0.6945(2) 0.34449(14) 0.10677(7) 0.0304 1.0000 Uani . . . . . . C12 C 0.7457(3) 0.33226(14) 0.35774(7) 0.0329 1.0000 Uani . . . . . . C13 C 0.5354(3) 0.33846(17) 0.39649(10) 0.0446 1.0000 Uani . . . . . . C14 C 0.9240(3) 0.3012(2) 0.40864(10) 0.0507 1.0000 Uani . . . . . . H21 H 0.9621(3) 0.11030(15) 0.05232(8) 0.0423 1.0000 Uiso R . . . . . H22 H 0.7215(3) 0.08142(15) 0.02710(8) 0.0423 1.0000 Uiso R . . . . . H31 H 0.8365(3) 0.05914(13) 0.16532(8) 0.0379 1.0000 Uiso R . . . . . H32 H 0.5966(3) 0.09764(13) 0.14363(8) 0.0379 1.0000 Uiso R . . . . . H51 H 0.5096(2) 0.28173(14) 0.23120(7) 0.0335 1.0000 Uiso R . . . . . H61 H 0.5644(3) 0.49319(13) 0.24925(7) 0.0378 1.0000 Uiso R . . . . . H71 H 0.8887(3) 0.59181(15) 0.20465(8) 0.0429 1.0000 Uiso R . . . . . H81 H 1.1892(3) 0.45335(17) 0.19996(8) 0.0457 1.0000 Uiso R . . . . . H91 H 1.1257(2) 0.22941(16) 0.17560(8) 0.0395 1.0000 Uiso R . . . . . H101 H 0.8366(3) 0.51942(14) 0.07919(9) 0.0488 1.0000 Uiso R . . . . . H102 H 0.6096(3) 0.53795(14) 0.11872(9) 0.0488 1.0000 Uiso R . . . . . H111 H 0.5390(2) 0.33384(14) 0.10587(7) 0.0365 1.0000 Uiso R . . . . . H131 H 0.4230(3) 0.35924(17) 0.36040(10) 0.0535 1.0000 Uiso R . . . . . H132 H 0.5399(3) 0.40675(17) 0.43483(10) 0.0535 1.0000 Uiso R . . . . . H133 H 0.5049(3) 0.25347(17) 0.41970(10) 0.0535 1.0000 Uiso R . . . . . H141 H 1.0580(3) 0.2984(2) 0.38050(10) 0.0609 1.0000 Uiso R . . . . . H142 H 0.9336(3) 0.3690(2) 0.44715(10) 0.0609 1.0000 Uiso R . . . . . H143 H 0.8987(3) 0.2158(2) 0.43201(10) 0.0609 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 0.0432(6) 0.0497(7) 0.0324(5) 0.0057(5) 0.0038(5) 0.0026(5) O2 0.0429(6) 0.0285(5) 0.0270(5) 0.0009(4) 0.0001(4) 0.0040(5) O3 0.0476(6) 0.0323(5) 0.0288(5) -0.0001(4) -0.0007(5) -0.0084(5) C1 0.0280(7) 0.0380(8) 0.0300(7) -0.0001(6) -0.0023(6) -0.0006(6) C2 0.0377(8) 0.0336(8) 0.0346(7) -0.0037(6) 0.0021(7) 0.0000(6) C3 0.0351(8) 0.0268(6) 0.0329(7) -0.0014(6) 0.0021(6) -0.0017(6) C4 0.0271(6) 0.0260(6) 0.0276(6) 0.0005(5) -0.0008(5) -0.0001(6) C5 0.0301(7) 0.0258(6) 0.0280(6) 0.0013(5) -0.0001(5) -0.0006(6) C6 0.0385(8) 0.0261(7) 0.0300(6) -0.0007(6) -0.0002(6) 0.0003(6) C7 0.0493(9) 0.0265(6) 0.0314(7) 0.0012(6) 0.0015(7) -0.0088(7) C8 0.0341(8) 0.0471(9) 0.0331(7) -0.0013(7) 0.0015(6) -0.0123(7) C9 0.0275(7) 0.0411(8) 0.0302(7) 0.0014(6) -0.0006(6) -0.0018(6) C10 0.0598(11) 0.0288(7) 0.0333(7) 0.0039(6) -0.0033(8) -0.0002(8) C11 0.0334(7) 0.0302(7) 0.0276(6) 0.0014(6) -0.0020(6) 0.0012(6) C12 0.0420(8) 0.0285(7) 0.0282(7) 0.0008(6) 0.0020(6) 0.0018(7) C13 0.0558(10) 0.0352(8) 0.0426(8) 0.0025(7) 0.0165(8) 0.0032(8) C14 0.0580(11) 0.0533(11) 0.0408(9) -0.0019(8) -0.0134(8) 0.0049(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.217(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 . C1 . 1.2112(18) yes O2 . C5 . 1.4295(16) yes O2 . C12 . 1.4278(17) yes O3 . C6 . 1.4258(17) yes O3 . C12 . 1.4233(18) yes C1 . C2 . 1.521(2) yes C1 . C11 . 1.511(2) yes C2 . C3 . 1.541(2) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.5318(19) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . C5 . 1.5264(19) yes C4 . C9 . 1.512(2) yes C4 . C11 . 1.5523(19) yes C5 . C6 . 1.554(2) yes C5 . H51 . 1.000 no C6 . C7 . 1.540(2) yes C6 . H61 . 1.000 no C7 . C8 . 1.498(2) yes C7 . C10 . 1.554(2) yes C7 . H71 . 1.000 no C8 . C9 . 1.327(2) yes C8 . H81 . 1.000 no C9 . H91 . 1.000 no C10 . C11 . 1.531(2) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C11 . H111 . 1.000 no C12 . C13 . 1.521(2) yes C12 . C14 . 1.508(2) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 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 C5 . O2 . C12 . 107.18(10) yes C6 . O3 . C12 . 108.18(11) yes O1 . C1 . C2 . 125.65(14) yes O1 . C1 . C11 . 126.08(14) yes C2 . C1 . C11 . 108.24(12) yes C1 . C2 . C3 . 105.20(12) yes C1 . C2 . H21 . 110.5 no C3 . C2 . H21 . 110.5 no C1 . C2 . H22 . 110.5 no C3 . C2 . H22 . 110.5 no H21 . C2 . H22 . 109.5 no C2 . C3 . C4 . 102.80(11) yes C2 . C3 . H31 . 111.1 no C4 . C3 . H31 . 111.1 no C2 . C3 . H32 . 111.1 no C4 . C3 . H32 . 111.1 no H31 . C3 . H32 . 109.5 no C3 . C4 . C5 . 118.11(12) yes C3 . C4 . C9 . 114.04(12) yes C5 . C4 . C9 . 108.74(11) yes C3 . C4 . C11 . 102.16(11) yes C5 . C4 . C11 . 105.32(11) yes C9 . C4 . C11 . 107.35(12) yes C4 . C5 . O2 . 112.00(11) yes C4 . C5 . C6 . 108.67(12) yes O2 . C5 . C6 . 104.67(11) yes C4 . C5 . H51 . 110.4 no O2 . C5 . H51 . 110.4 no C6 . C5 . H51 . 110.4 no C5 . C6 . O3 . 104.25(11) yes C5 . C6 . C7 . 110.62(12) yes O3 . C6 . C7 . 110.75(12) yes C5 . C6 . H61 . 110.4 no O3 . C6 . H61 . 110.4 no C7 . C6 . H61 . 110.4 no C6 . C7 . C8 . 108.97(13) yes C6 . C7 . C10 . 106.25(13) yes C8 . C7 . C10 . 107.68(13) yes C6 . C7 . H71 . 111.2 no C8 . C7 . H71 . 111.2 no C10 . C7 . H71 . 111.2 no C7 . C8 . C9 . 114.76(14) yes C7 . C8 . H81 . 122.6 no C9 . C8 . H81 . 122.6 no C4 . C9 . C8 . 114.69(14) yes C4 . C9 . H91 . 122.7 no C8 . C9 . H91 . 122.7 no C7 . C10 . C11 . 107.59(12) yes C7 . C10 . H101 . 109.9 no C11 . C10 . H101 . 109.9 no C7 . C10 . H102 . 109.9 no C11 . C10 . H102 . 109.9 no H101 . C10 . H102 . 109.5 no C10 . C11 . C4 . 112.05(12) yes C10 . C11 . C1 . 119.06(13) yes C4 . C11 . C1 . 101.18(11) yes C10 . C11 . H111 . 108.0 no C4 . C11 . H111 . 108.0 no C1 . C11 . H111 . 108.0 no O2 . C12 . O3 . 105.34(10) yes O2 . C12 . C13 . 110.39(14) yes O3 . C12 . C13 . 110.47(13) yes O2 . C12 . C14 . 108.61(13) yes O3 . C12 . C14 . 108.98(14) yes C13 . C12 . C14 . 112.76(14) yes C12 . C13 . H131 . 109.5 no C12 . C13 . H132 . 109.5 no H131 . C13 . H132 . 109.5 no C12 . C13 . H133 . 109.5 no H131 . C13 . H133 . 109.5 no H132 . C13 . H133 . 109.5 no C12 . C14 . H141 . 109.5 no C12 . C14 . H142 . 109.5 no H141 . C14 . H142 . 109.5 no C12 . C14 . H143 . 109.5 no H141 . C14 . H143 . 109.5 no H142 . C14 . H143 . 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 C1 3.139(2) . 2 no O1 C2 3.210(2) . 2 no O1 C11 3.380(2) . 2 no O1 C2 3.403(2) . 2_455 no O1 C3 3.530(2) . 2 no O2 C7 3.584(2) . 3_745 no O2 C8 3.598(2) . 3_745 no O3 C3 3.539(2) . 3_755 no C1 C1 3.570(1) . 2 no C1 C1 3.570(1) . 2_455 no C3 C13 3.529(2) . 3_645 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 C1 C2 C3 . . . . 176.0(1) no O1 C1 C11 C4 . . . . -150.2(1) no O1 C1 C11 C10 . . . . -27.0(2) no O2 C5 C4 C3 . . . . 72.5(2) no O2 C5 C4 C9 . . . . -59.5(1) no O2 C5 C4 C11 . . . . -174.3(1) no O2 C5 C6 O3 . . . . -2.0(2) no O2 C5 C6 C7 . . . . 117.1(1) no O2 C12 O3 C6 . . . . 31.1(2) no O3 C6 C5 C4 . . . . -121.8(1) no O3 C6 C7 C8 . . . . 63.3(2) no O3 C6 C7 C10 . . . . 179.1(1) no O3 C12 O2 C5 . . . . -32.2(2) no C1 C2 C3 C4 . . . . -24.9(2) no C1 C11 C4 C3 . . . . -43.5(1) no C1 C11 C4 C5 . . . . -167.4(1) no C1 C11 C4 C9 . . . . 76.8(1) no C1 C11 C10 C7 . . . . -121.5(1) no C2 C1 C11 C4 . . . . 28.3(1) no C2 C1 C11 C10 . . . . 151.5(1) no C2 C3 C4 C5 . . . . 157.4(1) no C2 C3 C4 C9 . . . . -73.1(2) no C2 C3 C4 C11 . . . . 42.4(1) no C3 C2 C1 C11 . . . . -2.5(2) no C3 C4 C5 C6 . . . . -172.3(1) no C3 C4 C9 C8 . . . . 168.5(1) no C3 C4 C11 C10 . . . . -171.3(1) no C4 C5 O2 C12 . . . . 138.3(1) no C4 C5 C6 C7 . . . . -2.7(2) no C4 C9 C8 C7 . . . . -0.7(2) no C4 C11 C10 C7 . . . . -3.9(2) no C5 O2 C12 C13 . . . . 87.0(1) no C5 O2 C12 C14 . . . . -148.9(1) no C5 C4 C9 C8 . . . . -57.3(2) no C5 C4 C11 C10 . . . . 64.7(1) no C5 C6 O3 C12 . . . . -17.6(2) no C5 C6 C7 C8 . . . . -51.8(2) no C5 C6 C7 C10 . . . . 64.0(2) no C6 O3 C12 C13 . . . . -88.1(1) no C6 O3 C12 C14 . . . . 147.5(1) no C6 C5 O2 C12 . . . . 20.8(1) no C6 C5 C4 C9 . . . . 55.7(1) no C6 C5 C4 C11 . . . . -59.2(1) no C6 C7 C8 C9 . . . . 56.1(2) no C6 C7 C10 C11 . . . . -58.8(2) no C7 C6 O3 C12 . . . . -136.6(1) no C8 C7 C10 C11 . . . . 57.8(2) no C8 C9 C4 C11 . . . . 56.1(2) no C9 C4 C11 C10 . . . . -51.1(2) no C9 C8 C7 C10 . . . . -58.8(2) no data_ban0632 _database_code_depnum_ccdc_archive 'CCDC 747029' _audit_creation_date 06-10-12 _audit_creation_method CRYSTALS_ver_12.18 _audit_update_record ; 2006-10-12 - Report on C14 H18 O3 by Anthony C. Willis for Kerrie Austin and Martin Banwell 2006-10-13 - passes checkcif tests with minor warnings ; _oxford_structure_analysis_title '10121435 ban0632' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.2050(1) _cell_length_b 11.5001(3) _cell_length_c 17.0648(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1217.71(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 = C14 H18 O3 # Dc = 1.28 Fooo = 504.00 Mu = 0.89 M = 234.30 # Found Formula = C14 H18 O3 # Dc = 1.28 FOOO = 504.00 Mu = 0.89 M = 234.30 _chemical_formula_sum 'C14 H18 O3' _chemical_formula_moiety 'C14 H18 O3' _chemical_compound_source local _chemical_formula_weight 234.30 _cell_measurement_reflns_used 10886 _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 0.18 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.46 _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.089 # Sheldrick geometric approximatio 0.98 0.98 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.843 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ; from symmetry-related measurements Sortav (Blessing 1995) ; # 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 40 sec/frame, crystal-detector distance 40mm, 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, 1997)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _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) ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 18151 _reflns_number_total 1612 _diffrn_reflns_av_R_equivalents 0.051 # Number of reflections with Friedels Law is 1612 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1396 _diffrn_reflns_theta_min 3.494 _diffrn_reflns_theta_max 27.482 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.482 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_diffrn_Wilson_B_factor 2.96 _oxford_diffrn_Wilson_scale 1.02 _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 0.18 _refine_ls_number_reflns 1169 _refine_ls_number_restraints 0 _refine_ls_number_parameters 154 #_refine_ls_R_factor_ref 0.0286 _refine_ls_wR_factor_ref 0.0331 _refine_ls_goodness_of_fit_ref 1.1573 #_reflns_number_all 1609 _refine_ls_R_factor_all 0.0398 _refine_ls_wR_factor_all 0.0389 # 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 1169 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_gt 0.0331 _refine_ls_shift/su_max 0.000289 # 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 syn _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: 0.656 0.188 0.430 ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~14~H~18~O~3~ is reported. ; _publ_section_comment #Text of the paper ; The compound is enantiometrically pure but the anomolous dispersion terms are very low for all elements in the structure and so the absolute configuration was not determined in this experiment. Friedel-pair reflections have been averaged. The absolute configuration of the molecule has been assigned on the basis of the synthetic precursors. The crystallographic asymmetric unit consists of one molecule of C~14~H~18~O~3~. Hydrogen atoms were included at idealized positions with the methyl groups oriented to best-fit peaks in difference electron density maps. During refinement the H atoms ride on the atoms to which they were bonded. The final difference electron density map is essentially featureless, with the largest peaks being located between carbon atoms. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; Hydrogen atoms were included at idealized positions and ride on the atoms to which they were bonded. ; _publ_section_exptl_prep ; The compound was prepared by KAA and recrystallized from dichloromethane/hexanes. The sample ID is KATV-02-46a. ; #**************************************************************************** # Insert your own references if required - in alphabetical order _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Blessing, R. H.; Acta Crystallogr., Section A, 51, 33-37 (1995). Blessing, R. H.; J. Appl. Crystallogr., 30, 421-426 (1997). Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Carruthers, J.R. & Watkin, D.J. (1979), Acta Cryst. A35, 698-699. Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 0.6935(3) 0.69425(13) 0.71218(9) 0.0543 1.0000 Uani . . . . . . O2 O 0.4377(2) 0.36003(10) 0.49840(7) 0.0352 1.0000 Uani . . . . . . O3 O 0.3135(2) 0.53566(10) 0.45982(7) 0.0351 1.0000 Uani . . . . . . C1 C 0.5547(3) 0.68656(16) 0.66278(11) 0.0358 1.0000 Uani . . . . . . C2 C 0.3910(4) 0.78062(16) 0.64345(13) 0.0453 1.0000 Uani . . . . . . C3 C 0.2386(3) 0.72577(15) 0.58261(12) 0.0381 1.0000 Uani . . . . . . C4 C 0.2635(3) 0.59441(15) 0.59673(10) 0.0298 1.0000 Uani . . . . . . C5 C 0.1463(3) 0.55035(16) 0.66823(10) 0.0364 1.0000 Uani . . . . . . C6 C 0.1953(3) 0.44190(17) 0.68845(10) 0.0386 1.0000 Uani . . . . . . C7 C 0.3628(3) 0.38479(15) 0.63760(10) 0.0337 1.0000 Uani . . . . . . C8 C 0.2730(3) 0.38629(15) 0.55408(10) 0.0324 1.0000 Uani . . . . . . C9 C 0.2009(3) 0.51130(15) 0.53066(9) 0.0318 1.0000 Uani . . . . . . C10 C 0.5678(3) 0.46102(15) 0.64240(11) 0.0333 1.0000 Uani . . . . . . C11 C 0.5090(3) 0.58175(15) 0.61174(10) 0.0281 1.0000 Uani . . . . . . C12 C 0.3940(3) 0.42733(15) 0.43008(10) 0.0336 1.0000 Uani . . . . . . C13 C 0.2247(4) 0.36849(19) 0.37962(12) 0.0481 1.0000 Uani . . . . . . C14 C 0.6026(3) 0.44990(18) 0.38742(11) 0.0420 1.0000 Uani . . . . . . H21 H 0.3093(4) 0.80362(16) 0.69151(13) 0.0543 1.0000 Uiso R . . . . . H22 H 0.4645(4) 0.85047(16) 0.62099(13) 0.0543 1.0000 Uiso R . . . . . H31 H 0.0864(3) 0.75110(15) 0.59161(12) 0.0459 1.0000 Uiso R . . . . . H32 H 0.2832(3) 0.74698(15) 0.52815(12) 0.0459 1.0000 Uiso R . . . . . H51 H 0.0404(3) 0.59876(16) 0.69801(10) 0.0437 1.0000 Uiso R . . . . . H61 H 0.1262(3) 0.40146(17) 0.73384(10) 0.0465 1.0000 Uiso R . . . . . H71 H 0.3927(3) 0.30352(15) 0.65539(10) 0.0406 1.0000 Uiso R . . . . . H81 H 0.1502(3) 0.33049(15) 0.54897(10) 0.0389 1.0000 Uiso R . . . . . H91 H 0.0417(3) 0.51367(15) 0.52160(9) 0.0381 1.0000 Uiso R . . . . . H101 H 0.6178(3) 0.46648(15) 0.69798(11) 0.0401 1.0000 Uiso R . . . . . H102 H 0.6846(3) 0.42649(15) 0.60945(11) 0.0401 1.0000 Uiso R . . . . . H111 H 0.5852(3) 0.59331(15) 0.56068(10) 0.0338 1.0000 Uiso R . . . . . H131 H 0.1964(4) 0.41702(19) 0.33209(12) 0.0580 1.0000 Uiso R . . . . . H132 H 0.0884(4) 0.35962(19) 0.41031(12) 0.0580 1.0000 Uiso R . . . . . H133 H 0.2778(4) 0.29009(19) 0.36318(12) 0.0580 1.0000 Uiso R . . . . . H141 H 0.5732(3) 0.49712(18) 0.33938(11) 0.0506 1.0000 Uiso R . . . . . H142 H 0.7033(3) 0.49339(18) 0.42254(11) 0.0506 1.0000 Uiso R . . . . . H143 H 0.6694(3) 0.37415(18) 0.37205(11) 0.0506 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 0.0479(8) 0.0564(9) 0.0586(9) -0.0243(8) -0.0186(8) 0.0122(7) O2 0.0442(7) 0.0293(6) 0.0321(6) 0.0014(5) 0.0058(6) 0.0040(6) O3 0.0461(7) 0.0305(6) 0.0286(6) 0.0006(5) -0.0013(6) 0.0022(6) C1 0.0341(9) 0.0330(9) 0.0404(10) -0.0084(8) -0.0016(8) 0.0036(8) C2 0.0514(11) 0.0294(9) 0.0550(12) -0.0084(9) -0.0115(11) 0.0094(9) C3 0.0387(10) 0.0314(8) 0.0441(10) -0.0014(7) -0.0059(9) 0.0099(8) C4 0.0295(9) 0.0278(8) 0.0320(8) -0.0005(6) -0.0020(7) 0.0061(7) C5 0.0326(9) 0.0432(10) 0.0333(8) -0.0043(8) 0.0029(7) 0.0069(8) C6 0.0397(10) 0.0421(10) 0.0341(9) 0.0021(7) 0.0089(8) -0.0017(9) C7 0.0397(10) 0.0282(8) 0.0331(8) 0.0045(7) 0.0038(8) 0.0036(8) C8 0.0355(9) 0.0279(8) 0.0337(8) -0.0021(7) 0.0032(8) -0.0031(7) C9 0.0277(8) 0.0330(8) 0.0346(9) 0.0001(7) -0.0023(8) 0.0035(7) C10 0.0333(9) 0.0320(8) 0.0344(9) 0.0007(7) -0.0040(8) 0.0077(7) C11 0.0288(8) 0.0266(8) 0.0291(8) -0.0020(7) -0.0007(7) 0.0027(7) C12 0.0412(10) 0.0288(8) 0.0307(8) -0.0027(7) -0.0015(8) -0.0020(8) C13 0.0532(12) 0.0510(11) 0.0402(10) -0.0107(9) -0.0015(10) -0.0135(11) C14 0.0431(11) 0.0441(10) 0.0389(10) -0.0002(8) 0.0052(9) -0.0032(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.043(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 . C1 . 1.208(2) yes O2 . C8 . 1.427(2) yes O2 . C12 . 1.425(2) yes O3 . C9 . 1.424(2) yes O3 . C12 . 1.435(2) yes C1 . C2 . 1.520(3) yes C1 . C11 . 1.514(2) yes C2 . C3 . 1.540(3) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.538(2) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . C5 . 1.508(2) yes C4 . C9 . 1.528(2) yes C4 . C11 . 1.552(2) yes C5 . C6 . 1.329(3) yes C5 . H51 . 1.000 no C6 . C7 . 1.505(3) yes C6 . H61 . 1.000 no C7 . C8 . 1.530(2) yes C7 . C10 . 1.547(3) yes C7 . H71 . 1.000 no C8 . C9 . 1.558(2) yes C8 . H81 . 1.000 no C9 . H91 . 1.000 no C10 . C11 . 1.528(2) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C11 . H111 . 1.000 no C12 . C13 . 1.518(3) yes C12 . C14 . 1.507(3) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 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 C8 . O2 . C12 . 107.08(13) yes C9 . O3 . C12 . 107.47(12) yes O1 . C1 . C2 . 125.14(17) yes O1 . C1 . C11 . 126.38(16) yes C2 . C1 . C11 . 108.45(15) yes C1 . C2 . C3 . 105.39(15) yes C1 . C2 . H21 . 110.4 no C3 . C2 . H21 . 110.5 no C1 . C2 . H22 . 110.5 no C3 . C2 . H22 . 110.5 no H21 . C2 . H22 . 109.5 no C2 . C3 . C4 . 103.58(15) yes C2 . C3 . H31 . 110.9 no C4 . C3 . H31 . 110.9 no C2 . C3 . H32 . 110.9 no C4 . C3 . H32 . 110.9 no H31 . C3 . H32 . 109.5 no C3 . C4 . C5 . 114.10(15) yes C3 . C4 . C9 . 118.24(14) yes C5 . C4 . C9 . 105.31(14) yes C3 . C4 . C11 . 102.54(15) yes C5 . C4 . C11 . 107.96(14) yes C9 . C4 . C11 . 108.23(15) yes C4 . C5 . C6 . 114.53(16) yes C4 . C5 . H51 . 122.7 no C6 . C5 . H51 . 122.7 no C5 . C6 . C7 . 114.69(17) yes C5 . C6 . H61 . 122.7 no C7 . C6 . H61 . 122.7 no C6 . C7 . C8 . 106.30(15) yes C6 . C7 . C10 . 106.86(15) yes C8 . C7 . C10 . 110.00(14) yes C6 . C7 . H71 . 111.2 no C8 . C7 . H71 . 111.2 no C10 . C7 . H71 . 111.2 no C7 . C8 . O2 . 110.92(14) yes C7 . C8 . C9 . 110.73(14) yes O2 . C8 . C9 . 103.31(13) yes C7 . C8 . H81 . 110.6 no O2 . C8 . H81 . 110.6 no C9 . C8 . H81 . 110.5 no C4 . C9 . C8 . 108.35(13) yes C4 . C9 . O3 . 112.23(14) yes C8 . C9 . O3 . 104.96(13) yes C4 . C9 . H91 . 110.4 no C8 . C9 . H91 . 110.4 no O3 . C9 . H91 . 110.4 no C7 . C10 . C11 . 107.51(14) yes C7 . C10 . H101 . 109.9 no C11 . C10 . H101 . 110.0 no C7 . C10 . H102 . 110.0 no C11 . C10 . H102 . 110.0 no H101 . C10 . H102 . 109.5 no C4 . C11 . C10 . 112.09(15) yes C4 . C11 . C1 . 101.78(14) yes C10 . C11 . C1 . 118.81(15) yes C4 . C11 . H111 . 107.9 no C10 . C11 . H111 . 107.9 no C1 . C11 . H111 . 107.9 no O3 . C12 . O2 . 104.38(12) yes O3 . C12 . C13 . 110.29(16) yes O2 . C12 . C13 . 110.70(15) yes O3 . C12 . C14 . 108.67(15) yes O2 . C12 . C14 . 109.00(16) yes C13 . C12 . C14 . 113.40(15) yes C12 . C13 . H131 . 109.4 no C12 . C13 . H132 . 109.5 no H131 . C13 . H132 . 109.5 no C12 . C13 . H133 . 109.5 no H131 . C13 . H133 . 109.5 no H132 . C13 . H133 . 109.5 no C12 . C14 . H141 . 109.5 no C12 . C14 . H142 . 109.5 no H141 . C14 . H142 . 109.5 no C12 . C14 . H143 . 109.4 no H141 . C14 . H143 . 109.5 no H142 . C14 . H143 . 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 C5 3.346(3) . 1_655 no O1 C6 3.386(2) . 3_656 no O1 C7 3.390(2) . 3_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 C1 C2 C3 . . . . -175.1(2) no O1 C1 C11 C4 . . . . 150.6(2) no O1 C1 C11 C10 . . . . 27.1(3) no O2 C8 C7 C6 . . . . 166.1(1) no O2 C8 C7 C10 . . . . 50.7(2) no O2 C8 C9 O3 . . . . 6.6(2) no O2 C8 C9 C4 . . . . -113.5(1) no O2 C12 O3 C9 . . . . -32.1(2) no O3 C9 C4 C3 . . . . 56.0(2) no O3 C9 C4 C5 . . . . -175.1(1) no O3 C9 C4 C11 . . . . -59.9(2) no O3 C9 C8 C7 . . . . 125.3(1) no O3 C12 O2 C8 . . . . 36.9(2) no C1 C2 C3 C4 . . . . 23.0(2) no C1 C11 C4 C3 . . . . 41.3(2) no C1 C11 C4 C5 . . . . -79.4(2) no C1 C11 C4 C9 . . . . 167.0(1) no C1 C11 C10 C7 . . . . 126.0(2) no C2 C1 C11 C4 . . . . -27.5(2) no C2 C1 C11 C10 . . . . -151.1(2) no C2 C3 C4 C5 . . . . 76.5(2) no C2 C3 C4 C9 . . . . -158.9(2) no C2 C3 C4 C11 . . . . -40.0(2) no C3 C2 C1 C11 . . . . 3.1(2) no C3 C4 C5 C6 . . . . -169.3(2) no C3 C4 C9 C8 . . . . 171.4(2) no C3 C4 C11 C10 . . . . 169.4(1) no C4 C5 C6 C7 . . . . 1.6(2) no C4 C9 O3 C12 . . . . 133.0(1) no C4 C9 C8 C7 . . . . 5.2(2) no C4 C11 C10 C7 . . . . 7.6(2) no C5 C4 C9 C8 . . . . -59.7(2) no C5 C4 C11 C10 . . . . 48.6(2) no C5 C6 C7 C8 . . . . -58.7(2) no C5 C6 C7 C10 . . . . 58.8(2) no C6 C5 C4 C9 . . . . 59.4(2) no C6 C5 C4 C11 . . . . -56.0(2) no C6 C7 C8 C9 . . . . 52.0(2) no C6 C7 C10 C11 . . . . -60.4(2) no C7 C8 O2 C12 . . . . -145.1(1) no C8 O2 C12 C13 . . . . -81.8(2) no C8 O2 C12 C14 . . . . 152.8(1) no C8 C7 C10 C11 . . . . 54.6(2) no C8 C9 O3 C12 . . . . 15.5(2) no C8 C9 C4 C11 . . . . 55.6(2) no C9 O3 C12 C13 . . . . 86.8(2) no C9 O3 C12 C14 . . . . -148.3(1) no C9 C4 C11 C10 . . . . -65.0(2) no C9 C8 O2 C12 . . . . -26.4(2) no C9 C8 C7 C10 . . . . -63.3(2) no data_ban0814 _database_code_depnum_ccdc_archive 'CCDC 747030' _audit_creation_date 08-06-23 _audit_creation_method CRYSTALS_ver_12.85 _audit_update_record ; 2008-06-23 - Report on C18 H18 O3 by Anthony C. Willis for Kerrie Austin and Martin Banwell 2008-06-23 - passes checkcif tests with minor warnings ; _oxford_structure_analysis_title '6231006 ban0814' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.7159(2) _cell_length_b 9.7758(2) _cell_length_c 14.8253(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1408.12(6) _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 = C18 H18 O3 # Dc = 1.33 Fooo = 600.00 Mu = 0.90 M = 282.34 # Found Formula = C18 H18 O3 # Dc = 1.33 FOOO = 600.00 Mu = 0.90 M = 282.34 _chemical_formula_sum 'C18 H18 O3' _chemical_formula_moiety 'C18 H18 O3' _chemical_compound_source ? _chemical_formula_weight 282.34 _cell_measurement_reflns_used 10654 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 30 _cell_measurement_temperature 200 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.46 _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.090 # Sheldrick geometric approximatio 0.96 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 1 0 0 0.230 -1 0 0 0.250 0 1 0 0.220 0 -1 0 0.170 0 0 1 0.110 0 0 -1 0.090 -3 4 0 0.228 1 -1 0 0.233 0 3 -3 0.190 0 -1 1 0.172 0 1 1 0.209 0 -5 -5 0.158 -8 0 -8 0.224 6 0 6 0.207 5 0 -5 0.208 -5 0 5 0.230 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.025 # 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 'Nonius KappaCCD' _diffrn_measurement_device_type Area _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 180 sec/frame, crystal-detector distance 40mm, multiple scan sets so over 90 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, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _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 18313 _reflns_number_total 2326 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections with Friedels Law is 2326 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2062 _diffrn_reflns_theta_min 2.956 _diffrn_reflns_theta_max 30.043 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.043 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min 0 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _oxford_diffrn_Wilson_B_factor 2.42 _oxford_diffrn_Wilson_scale 0.35 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.12 _refine_diff_density_max 0.21 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 2326 _refine_ls_number_restraints 0 _refine_ls_number_parameters 244 _oxford_refine_ls_R_factor_ref 0.0341 _refine_ls_wR_factor_ref 0.0810 _refine_ls_goodness_of_fit_ref 0.9550 _refine_ls_shift/su_max 0.004411 # The values computed from all data _oxford_reflns_number_all 2326 _refine_ls_R_factor_all 0.0341 _refine_ls_wR_factor_all 0.0810 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2075 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_gt 0.0797 # 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 syn _refine_ls_abs_structure_details ; The enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure. ; _refine_ls_structure_factor_coef Fsqd _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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~18~H~18~O~3~ is reported. ; _publ_section_comment #Text of the paper ; The compound is enantiometrically pure but the anomolous dispersion terms are very low for all elements in the structure and so the absolute configuration can not be determined in this experiment. Consequently Friedel-pair reflections have been averaged and the Flack parameter has not been refined. The absolute configuration of the molecule has been assigned on the basis of the synthetic precursors. The crystallographic asymmetric unit consists of one molecule of C~18~H~18~O~3~. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; All hydrogen atoms were observed in difference electron density maps prior to their inclusion. They were included at calculated positions and were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined without restraints and displacement factors were kept fixed. The final difference electron density map is essentially featureless, with the largest peaks being located between carbon atoms. ; _publ_section_exptl_prep ; The compound was prepared by KAA and recrystallized from ethylacetate. The sample ID is KATV-07-97. ; #**************************************************************************** # Insert your own references if required - in alphabetical order _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O 0.52237(13) 0.21291(11) 0.52709(7) 0.0424 1.0000 Uani . . . . . . . O2 O 0.53523(10) 0.81157(10) 0.34673(7) 0.0363 1.0000 Uani . . . . . . . O3 O 0.68373(10) 0.79652(10) 0.46335(6) 0.0308 1.0000 Uani . . . . . . . C1 C 0.57063(14) 0.32655(13) 0.53627(9) 0.0314 1.0000 Uani . . . . . . . C2 C 0.70213(17) 0.36124(15) 0.58683(10) 0.0405 1.0000 Uani . . . . . . . C3 C 0.71395(16) 0.51811(15) 0.58240(9) 0.0377 1.0000 Uani . . . . . . . C4 C 0.63954(12) 0.55318(12) 0.49407(8) 0.0250 1.0000 Uani . . . . . . . C5 C 0.71977(14) 0.52025(13) 0.40983(9) 0.0334 1.0000 Uani . . . . . . . C6 C 0.64793(19) 0.52859(16) 0.33451(9) 0.0425 1.0000 Uani . . . . . . . C7 C 0.49863(18) 0.56353(16) 0.34706(10) 0.0421 1.0000 Uani . . . . . . . C8 C 0.48583(14) 0.69824(14) 0.39899(10) 0.0344 1.0000 Uani . . . . . . . C9 C 0.58028(13) 0.69667(13) 0.48332(8) 0.0283 1.0000 Uani . . . . . . . C10 C 0.43501(18) 0.45148(17) 0.40789(12) 0.0461 1.0000 Uani . . . . . . . C11 C 0.51250(13) 0.45707(13) 0.49775(9) 0.0299 1.0000 Uani . . . . . . . C12 C 0.62074(13) 0.89116(13) 0.40384(9) 0.0308 1.0000 Uani . . . . . . . C13 C 0.72468(13) 0.96545(13) 0.34754(8) 0.0279 1.0000 Uani . . . . . . . C14 C 0.81067(16) 0.89227(14) 0.29021(9) 0.0356 1.0000 Uani . . . . . . . C15 C 0.90107(18) 0.96025(18) 0.23365(11) 0.0431 1.0000 Uani . . . . . . . C16 C 0.90561(19) 1.10230(18) 0.23402(10) 0.0437 1.0000 Uani . . . . . . . C17 C 0.82143(18) 1.17528(15) 0.29140(11) 0.0421 1.0000 Uani . . . . . . . C18 C 0.73044(15) 1.10759(14) 0.34818(9) 0.0335 1.0000 Uani . . . . . . . H21 H 0.702(2) 0.322(2) 0.6461(13) 0.0511 1.0000 Uiso . . . . . . . H22 H 0.780(2) 0.313(2) 0.5496(12) 0.0499 1.0000 Uiso . . . . . . . H31 H 0.811(2) 0.5512(19) 0.5830(12) 0.0472 1.0000 Uiso . . . . . . . H32 H 0.660(2) 0.567(2) 0.6369(13) 0.0471 1.0000 Uiso . . . . . . . H51 H 0.819(2) 0.4952(18) 0.4131(12) 0.0414 1.0000 Uiso . . . . . . . H61 H 0.683(2) 0.514(2) 0.2749(14) 0.0506 1.0000 Uiso . . . . . . . H71 H 0.448(2) 0.569(2) 0.2861(13) 0.0505 1.0000 Uiso . . . . . . . H81 H 0.390(2) 0.7131(19) 0.4199(12) 0.0410 1.0000 Uiso . . . . . . . H91 H 0.5330(18) 0.7267(18) 0.5388(11) 0.0340 1.0000 Uiso . . . . . . . H101 H 0.331(2) 0.468(2) 0.4181(14) 0.0577 1.0000 Uiso . . . . . . . H102 H 0.450(2) 0.362(2) 0.3798(12) 0.0561 1.0000 Uiso . . . . . . . H111 H 0.4487(18) 0.4910(17) 0.5470(11) 0.0370 1.0000 Uiso . . . . . . . H121 H 0.5626(18) 0.9570(18) 0.4412(10) 0.0356 1.0000 Uiso . . . . . . . H141 H 0.808(2) 0.7911(19) 0.2909(13) 0.0430 1.0000 Uiso . . . . . . . H151 H 0.960(2) 0.910(2) 0.1916(13) 0.0523 1.0000 Uiso . . . . . . . H161 H 0.972(2) 1.149(2) 0.1897(13) 0.0552 1.0000 Uiso . . . . . . . H171 H 0.824(2) 1.275(2) 0.2869(13) 0.0523 1.0000 Uiso . . . . . . . H181 H 0.673(2) 1.1614(19) 0.3909(12) 0.0400 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 0.0531(6) 0.0300(5) 0.0441(6) 0.0003(4) 0.0023(5) -0.0056(5) O2 0.0343(5) 0.0321(5) 0.0426(5) 0.0083(4) -0.0143(4) -0.0032(4) O3 0.0348(4) 0.0278(4) 0.0298(4) 0.0022(3) -0.0080(4) -0.0045(4) C1 0.0346(6) 0.0299(6) 0.0298(5) 0.0017(5) 0.0070(5) -0.0005(5) C2 0.0436(8) 0.0373(7) 0.0408(7) 0.0136(6) -0.0079(6) -0.0028(6) C3 0.0417(8) 0.0381(7) 0.0332(6) 0.0087(6) -0.0114(6) -0.0083(6) C4 0.0249(5) 0.0257(5) 0.0244(5) 0.0011(4) -0.0012(4) -0.0010(4) C5 0.0345(7) 0.0281(6) 0.0376(6) 0.0037(5) 0.0111(5) 0.0055(5) C6 0.0702(10) 0.0309(6) 0.0265(6) -0.0028(5) 0.0082(6) 0.0031(7) C7 0.0553(9) 0.0336(7) 0.0373(7) 0.0039(5) -0.0214(7) -0.0069(6) C8 0.0262(6) 0.0292(6) 0.0478(7) 0.0069(5) -0.0089(5) 0.0004(5) C9 0.0299(6) 0.0271(5) 0.0280(6) -0.0023(4) 0.0011(5) 0.0009(5) C10 0.0453(9) 0.0358(7) 0.0573(9) 0.0072(7) -0.0227(7) -0.0119(7) C11 0.0255(5) 0.0289(6) 0.0352(6) 0.0002(5) 0.0021(5) -0.0016(5) C12 0.0313(6) 0.0263(5) 0.0349(6) -0.0014(5) -0.0033(5) 0.0035(5) C13 0.0301(5) 0.0253(5) 0.0282(5) -0.0011(5) -0.0069(5) 0.0016(5) C14 0.0408(7) 0.0274(6) 0.0385(6) -0.0040(5) 0.0007(6) 0.0011(6) C15 0.0449(8) 0.0434(8) 0.0410(7) -0.0044(6) 0.0067(6) 0.0001(7) C16 0.0454(8) 0.0437(8) 0.0419(7) 0.0066(7) 0.0007(7) -0.0083(7) C17 0.0491(8) 0.0275(6) 0.0496(8) 0.0037(6) -0.0073(7) -0.0052(6) C18 0.0393(6) 0.0253(6) 0.0357(6) -0.0040(5) -0.0064(6) 0.0027(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.885(14) 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 . C1 . 1.2134(17) yes O2 . C8 . 1.4346(17) yes O2 . C12 . 1.4186(16) yes O3 . C9 . 1.4320(15) yes O3 . C12 . 1.4173(15) yes C1 . C2 . 1.520(2) yes C1 . C11 . 1.5077(18) yes C2 . C3 . 1.539(2) yes C2 . H21 . 0.961(19) no C2 . H22 . 1.05(2) no C3 . C4 . 1.5346(17) yes C3 . H31 . 1.00(2) no C3 . H32 . 1.07(2) no C4 . C5 . 1.5070(17) yes C4 . C9 . 1.5247(17) yes C4 . C11 . 1.5521(17) yes C5 . C6 . 1.319(2) yes C5 . H51 . 0.998(19) no C6 . C7 . 1.502(3) yes C6 . H61 . 0.96(2) no C7 . C8 . 1.531(2) yes C7 . C10 . 1.548(2) yes C7 . H71 . 1.031(19) no C8 . C9 . 1.5509(18) yes C8 . H81 . 0.994(19) no C9 . H91 . 0.987(16) no C10 . C11 . 1.531(2) yes C10 . H101 . 1.04(2) no C10 . H102 . 0.98(2) no C11 . H111 . 1.014(17) no C12 . C13 . 1.4980(18) yes C12 . H121 . 1.020(17) no C13 . C14 . 1.3900(19) yes C13 . C18 . 1.3907(18) yes C14 . C15 . 1.384(2) yes C14 . H141 . 0.990(19) no C15 . C16 . 1.389(2) yes C15 . H151 . 0.98(2) no C16 . C17 . 1.379(2) yes C16 . H161 . 1.03(2) no C17 . C18 . 1.389(2) yes C17 . H171 . 0.98(2) no C18 . H181 . 0.997(19) 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 C8 . O2 . C12 . 107.29(10) yes C9 . O3 . C12 . 105.69(9) yes O1 . C1 . C2 . 125.77(13) yes O1 . C1 . C11 . 125.99(13) yes C2 . C1 . C11 . 108.23(11) yes C1 . C2 . C3 . 105.31(12) yes C1 . C2 . H21 . 111.2(13) no C3 . C2 . H21 . 116.1(13) no C1 . C2 . H22 . 104.3(11) no C3 . C2 . H22 . 111.9(11) no H21 . C2 . H22 . 107.4(16) no C2 . C3 . C4 . 102.94(11) yes C2 . C3 . H31 . 113.2(11) no C4 . C3 . H31 . 112.4(10) no C2 . C3 . H32 . 112.0(11) no C4 . C3 . H32 . 108.3(10) no H31 . C3 . H32 . 108.0(16) no C3 . C4 . C5 . 114.57(11) yes C3 . C4 . C9 . 118.21(11) yes C5 . C4 . C9 . 107.77(10) yes C3 . C4 . C11 . 102.09(10) yes C5 . C4 . C11 . 108.13(10) yes C9 . C4 . C11 . 105.09(10) yes C4 . C5 . C6 . 114.49(12) yes C4 . C5 . H51 . 120.8(11) no C6 . C5 . H51 . 124.7(11) no C5 . C6 . C7 . 114.86(13) yes C5 . C6 . H61 . 125.4(13) no C7 . C6 . H61 . 119.8(13) no C6 . C7 . C8 . 109.66(12) yes C6 . C7 . C10 . 107.28(13) yes C8 . C7 . C10 . 106.46(13) yes C6 . C7 . H71 . 111.5(11) no C8 . C7 . H71 . 110.9(11) no C10 . C7 . H71 . 110.9(11) no C7 . C8 . O2 . 111.45(12) yes C7 . C8 . C9 . 110.42(11) yes O2 . C8 . C9 . 104.18(10) yes C7 . C8 . H81 . 111.0(10) no O2 . C8 . H81 . 111.7(11) no C9 . C8 . H81 . 107.8(10) no C8 . C9 . C4 . 108.47(10) yes C8 . C9 . O3 . 104.00(10) yes C4 . C9 . O3 . 112.56(10) yes C8 . C9 . H91 . 113.2(10) no C4 . C9 . H91 . 111.3(10) no O3 . C9 . H91 . 107.2(10) no C7 . C10 . C11 . 106.58(11) yes C7 . C10 . H101 . 111.5(12) no C11 . C10 . H101 . 110.4(12) no C7 . C10 . H102 . 109.0(12) no C11 . C10 . H102 . 109.1(11) no H101 . C10 . H102 . 110.2(18) no C10 . C11 . C4 . 112.46(11) yes C10 . C11 . C1 . 118.91(12) yes C4 . C11 . C1 . 103.17(10) yes C10 . C11 . H111 . 109.7(9) no C4 . C11 . H111 . 108.3(10) no C1 . C11 . H111 . 103.5(9) no O2 . C12 . O3 . 105.45(10) yes O2 . C12 . C13 . 109.16(10) yes O3 . C12 . C13 . 111.85(10) yes O2 . C12 . H121 . 110.2(9) no O3 . C12 . H121 . 108.3(9) no C13 . C12 . H121 . 111.7(10) no C12 . C13 . C14 . 119.76(12) yes C12 . C13 . C18 . 120.51(13) yes C14 . C13 . C18 . 119.62(13) yes C13 . C14 . C15 . 120.31(14) yes C13 . C14 . H141 . 119.4(11) no C15 . C14 . H141 . 120.3(11) no C14 . C15 . C16 . 119.84(16) yes C14 . C15 . H151 . 120.9(12) no C16 . C15 . H151 . 119.2(12) no C15 . C16 . C17 . 120.04(16) yes C15 . C16 . H161 . 117.7(12) no C17 . C16 . H161 . 122.3(12) no C16 . C17 . C18 . 120.34(14) yes C16 . C17 . H171 . 117.3(12) no C18 . C17 . H171 . 122.2(12) no C13 . C18 . C17 . 119.84(14) yes C13 . C18 . H181 . 120.6(10) no C17 . C18 . H181 . 119.5(10) 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 C18 3.490(2) . 1_545 no O1 C17 3.500(2) . 2_466 no O1 C15 3.577(2) . 4_665 no O3 C8 3.575(2) . 2_566 no C1 C17 3.520(2) . 2_466 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 C1 C2 C3 . . . . -177.4(1) no O1 C1 C11 C4 . . . . -156.7(1) no O1 C1 C11 C10 . . . . -31.4(2) no O2 C8 C7 C6 . . . . 67.4(1) no O2 C8 C7 C10 . . . . -176.9(1) no O2 C8 C9 O3 . . . . -7.7(1) no O2 C8 C9 C4 . . . . -127.8(1) no O2 C12 O3 C9 . . . . -37.8(1) no O2 C12 C13 C14 . . . . -56.0(2) no O2 C12 C13 C18 . . . . 120.2(1) no O3 C9 C4 C3 . . . . 77.0(1) no O3 C9 C4 C5 . . . . -54.9(1) no O3 C9 C4 C11 . . . . -170.0(1) no O3 C9 C8 C7 . . . . 112.0(1) no O3 C12 O2 C8 . . . . 32.6(1) no O3 C12 C13 C14 . . . . 60.3(2) no O3 C12 C13 C18 . . . . -123.5(1) no C1 C2 C3 C4 . . . . -28.5(1) no C1 C11 C4 C3 . . . . -39.3(1) no C1 C11 C4 C5 . . . . 81.8(1) no C1 C11 C4 C9 . . . . -163.3(1) no C1 C11 C10 C7 . . . . -129.4(1) no C2 C1 C11 C4 . . . . 22.0(1) no C2 C1 C11 C10 . . . . 147.3(1) no C2 C3 C4 C5 . . . . -74.8(1) no C2 C3 C4 C9 . . . . 156.4(1) no C2 C3 C4 C11 . . . . 41.8(1) no C3 C2 C1 C11 . . . . 3.9(1) no C3 C4 C5 C6 . . . . 169.2(1) no C3 C4 C9 C8 . . . . -168.5(1) no C3 C4 C11 C10 . . . . -168.7(1) no C4 C5 C6 C7 . . . . -2.4(2) no C4 C9 O3 C12 . . . . 144.6(1) no C4 C9 C8 C7 . . . . -8.0(1) no C4 C11 C10 C7 . . . . -8.7(2) no C5 C4 C9 C8 . . . . 59.6(1) no C5 C4 C11 C10 . . . . -47.5(1) no C5 C6 C7 C8 . . . . 56.6(2) no C5 C6 C7 C10 . . . . -58.7(2) no C6 C5 C4 C9 . . . . -57.0(1) no C6 C5 C4 C11 . . . . 56.1(1) no C6 C7 C8 C9 . . . . -47.9(2) no C6 C7 C10 C11 . . . . 61.0(2) no C7 C8 O2 C12 . . . . -133.9(1) no C8 O2 C12 C13 . . . . 153.0(1) no C8 C7 C10 C11 . . . . -56.4(2) no C8 C9 O3 C12 . . . . 27.4(1) no C8 C9 C4 C11 . . . . -55.5(1) no C9 O3 C12 C13 . . . . -156.3(1) no C9 C4 C11 C10 . . . . 67.4(1) no C9 C8 O2 C12 . . . . -14.8(1) no C9 C8 C7 C10 . . . . 67.8(2) no C12 C13 C14 C15 . . . . 175.9(1) no C12 C13 C18 C17 . . . . -175.9(1) no C13 C14 C15 C16 . . . . -0.2(2) no C13 C18 C17 C16 . . . . 0.3(2) no C14 C13 C18 C17 . . . . 0.3(2) no C14 C15 C16 C17 . . . . 0.8(3) no C15 C14 C13 C18 . . . . -0.4(2) no C15 C16 C17 C18 . . . . -0.9(3) no data_ban0809 _database_code_depnum_ccdc_archive 'CCDC 747031' _audit_creation_date 08-05-12 _audit_creation_method CRYSTALS_ver_12.18 _audit_update_record ; 2008-05-12 - Report on C16 H22 O3 by Anthony C. Willis for Kerrie Austin and Martin Banwell 2008-05-12 - passes checkcif tests with minor warnings ; _oxford_structure_analysis_title '5121139 ban0809' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.3467(2) _cell_length_b 21.7077(6) _cell_length_c 10.3198(3) _cell_angle_alpha 90 _cell_angle_beta 90.9585(16) _cell_angle_gamma 90 _cell_volume 1421.58(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,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 = C16 H22 O3 # Dc = 1.23 Fooo = 568.00 Mu = 0.83 M = 524.70 # Found Formula = C16 H22 O3 # Dc = 1.23 FOOO = 568.00 Mu = 0.83 M = 524.70 _chemical_formula_sum 'C16 H22 O3' _chemical_formula_moiety 'C16 H22 O3' _chemical_compound_source local _chemical_formula_weight 262.35 _cell_measurement_reflns_used 78878 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 25 _cell_measurement_temperature 200 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_max 0.36 _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.083 # 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 0.140 -1 0 0 0.220 0 1 0 0.010 0 -1 0 0.080 0 0 1 0.030 0 0 -1 0.100 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.979 _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 0.6 deg at rate 66 sec/frame, crystal-detector distance 40mm, multiple scan sets so over 90 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, 1997)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _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) ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 21145 _reflns_number_total 2589 _diffrn_reflns_av_R_equivalents 0.054 # Number of reflections with Friedels Law is 2589 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2517 _diffrn_reflns_theta_min 2.724 _diffrn_reflns_theta_max 25.048 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.048 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 25 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _oxford_diffrn_Wilson_B_factor 3.49 _oxford_diffrn_Wilson_scale 0.95 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.12 _refine_diff_density_max 0.11 _refine_ls_number_reflns 2064 _refine_ls_number_restraints 1 _refine_ls_number_parameters 343 #_refine_ls_R_factor_ref 0.0279 _refine_ls_wR_factor_ref 0.0308 _refine_ls_goodness_of_fit_ref 1.1875 #_reflns_number_all 2583 _refine_ls_R_factor_all 0.0384 _refine_ls_wR_factor_all 0.0358 # 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 2064 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_gt 0.0308 _refine_ls_shift/su_max 0.000469 # 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 syn _refine_ls_abs_structure_details ; The enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure. ; _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, (Carruthers & Watkin, 1979, 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: 0.733 0.166 0.518 ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~16~H~22~O~3~ is reported. ; _publ_section_comment #Text of the paper ; The compound is enantiometrically pure but the anomolous dispersion terms are very low for all elements in the structure and so the absolute configuration can not be determined in this experiment. Consequently Friedel-pair reflections have been averaged and the Flack parameter has not been refined. The absolute configuration of the molecule has been assigned on the basis of the synthetic precursors. The crystallographic asymmetric unit consists of two molecules of C~16~H~22~O~3~. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; All hydrogen atoms were observed in difference electron density maps prior to their inclusion. They were included at calculated positions (C---H 1.00\%A, U~iso~(H) = 1.2\\timesU~eq~(C)) and ride on the atom to which they are bonded. The final difference electron density map is essentially featureless, with the largest peaks being located between carbon atoms. ; _publ_section_exptl_prep ; The compound was prepared by KAA and recrystallized from methanol. The sample ID is KATV-07-61d. ; #**************************************************************************** # Insert your own references if required - in alphabetical order _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Carruthers, J.R. & Watkin, D.J. (1979), Acta Cryst. A35, 698-699. Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 0.1866(3) 0.66748(9) 0.13935(16) 0.0497 1.0000 Uani . . . . . . O2 O 0.0194(3) 0.73698(8) 0.69306(15) 0.0406 1.0000 Uani . . . . . . O3 O 0.1079(3) 0.83661(9) 0.65590(15) 0.0430 1.0000 Uani . . . . . . O101 O 0.6876(3) 0.62613(9) 1.21649(16) 0.0502 1.0000 Uani . . . . . . O102 O 0.5099(3) 0.55487(8) 0.66160(15) 0.0411 1.0000 Uani . . . . . . O103 O 0.6018(3) 0.45566(8) 0.70099(14) 0.0425 1.0000 Uani . . . . . . C1 C 0.1595(4) 0.66907(12) 0.2558(2) 0.0395 1.0000 Uani . . . . . . C2 C 0.1880(4) 0.61508(13) 0.3470(2) 0.0454 1.0000 Uani . . . . . . C3 C 0.0904(4) 0.63563(11) 0.4751(2) 0.0412 1.0000 Uani . . . . . . C4 C 0.1302(3) 0.70501(11) 0.4760(2) 0.0342 1.0000 Uani . . . . . . C5 C -0.0149(4) 0.74554(11) 0.5571(2) 0.0341 1.0000 Uani . . . . . . C6 C 0.0400(4) 0.81368(11) 0.5323(2) 0.0357 1.0000 Uani . . . . . . C7 C 0.2226(4) 0.81907(11) 0.4370(2) 0.0370 1.0000 Uani . . . . . . C8 C 0.4005(4) 0.78108(12) 0.4926(2) 0.0388 1.0000 Uani . . . . . . C9 C 0.3546(4) 0.72235(11) 0.5113(2) 0.0370 1.0000 Uani . . . . . . C10 C 0.1580(4) 0.79052(12) 0.3024(2) 0.0366 1.0000 Uani . . . . . . C11 C 0.0841(3) 0.72389(11) 0.3328(2) 0.0346 1.0000 Uani . . . . . . C12 C 0.0297(4) 0.79598(12) 0.7522(2) 0.0390 1.0000 Uani . . . . . . C13 C 0.1879(4) 0.79343(13) 0.8620(3) 0.0501 1.0000 Uani . . . . . . C14 C -0.1860(4) 0.81731(13) 0.7947(3) 0.0490 1.0000 Uani . . . . . . C15 C 0.3516(4) 0.79319(13) 0.2150(2) 0.0450 1.0000 Uani . . . . . . C16 C -0.0195(4) 0.82813(13) 0.2378(2) 0.0464 1.0000 Uani . . . . . . C101 C 0.6572(4) 0.62429(12) 1.1004(2) 0.0405 1.0000 Uani . . . . . . C102 C 0.6822(4) 0.67813(12) 1.0080(2) 0.0451 1.0000 Uani . . . . . . C103 C 0.5846(4) 0.65669(11) 0.8785(2) 0.0419 1.0000 Uani . . . . . . C104 C 0.6247(3) 0.58738(11) 0.8795(2) 0.0347 1.0000 Uani . . . . . . C105 C 0.4784(4) 0.54675(11) 0.7973(2) 0.0363 1.0000 Uani . . . . . . C106 C 0.5345(4) 0.47866(11) 0.8235(2) 0.0367 1.0000 Uani . . . . . . C107 C 0.7181(4) 0.47369(11) 0.9225(2) 0.0363 1.0000 Uani . . . . . . C108 C 0.8956(4) 0.51144(12) 0.8685(2) 0.0380 1.0000 Uani . . . . . . C109 C 0.8489(4) 0.57015(12) 0.8486(2) 0.0370 1.0000 Uani . . . . . . C110 C 0.6560(4) 0.50233(12) 1.0553(2) 0.0374 1.0000 Uani . . . . . . C111 C 0.5808(3) 0.56896(12) 1.0223(2) 0.0364 1.0000 Uani . . . . . . C112 C 0.5215(4) 0.49569(11) 0.6022(2) 0.0390 1.0000 Uani . . . . . . C113 C 0.6784(5) 0.49922(13) 0.4946(2) 0.0512 1.0000 Uani . . . . . . C114 C 0.3055(5) 0.47390(13) 0.5569(3) 0.0503 1.0000 Uani . . . . . . C115 C 0.8476(4) 0.50021(14) 1.1466(2) 0.0460 1.0000 Uani . . . . . . C116 C 0.4781(4) 0.46557(13) 1.1182(2) 0.0468 1.0000 Uani . . . . . . H21 H 0.3410 0.60555 0.3600 0.0544 1.0000 Uiso R . . . . . H22 H 0.1136 0.57788 0.3120 0.0544 1.0000 Uiso R . . . . . H31 H 0.1617 0.61521 0.5508 0.0495 1.0000 Uiso R . . . . . H32 H -0.0639 0.62636 0.4761 0.0495 1.0000 Uiso R . . . . . H51 H -0.1658 0.73741 0.5334 0.0411 1.0000 Uiso R . . . . . H61 H -0.0863 0.83679 0.4995 0.0428 1.0000 Uiso R . . . . . H71 H 0.2666 0.86302 0.4270 0.0444 1.0000 Uiso R . . . . . H81 H 0.5423 0.79885 0.5137 0.0466 1.0000 Uiso R . . . . . H91 H 0.4597 0.69194 0.5460 0.0443 1.0000 Uiso R . . . . . H111 H -0.0728 0.72427 0.3225 0.0415 1.0000 Uiso R . . . . . H131 H 0.1972 0.83470 0.9048 0.0601 1.0000 Uiso R . . . . . H132 H 0.1429 0.76194 0.9266 0.0601 1.0000 Uiso R . . . . . H133 H 0.3290 0.78195 0.8277 0.0601 1.0000 Uiso R . . . . . H141 H -0.1737 0.85888 0.8359 0.0588 1.0000 Uiso R . . . . . H142 H -0.2831 0.81974 0.7175 0.0588 1.0000 Uiso R . . . . . H143 H -0.2434 0.78734 0.8587 0.0588 1.0000 Uiso R . . . . . H151 H 0.3147 0.77527 0.1283 0.0540 1.0000 Uiso R . . . . . H152 H 0.3966 0.83701 0.2042 0.0540 1.0000 Uiso R . . . . . H153 H 0.4693 0.76899 0.2557 0.0540 1.0000 Uiso R . . . . . H161 H -0.0582 0.80923 0.1523 0.0559 1.0000 Uiso R . . . . . H162 H 0.0293 0.87141 0.2242 0.0559 1.0000 Uiso R . . . . . H163 H -0.1454 0.82822 0.2948 0.0559 1.0000 Uiso R . . . . . H1021 H 0.6062 0.71516 1.0410 0.0541 1.0000 Uiso R . . . . . H1022 H 0.8347 0.68828 0.9975 0.0541 1.0000 Uiso R . . . . . H1031 H 0.6555 0.67682 0.8038 0.0503 1.0000 Uiso R . . . . . H1032 H 0.4302 0.66582 0.8743 0.0503 1.0000 Uiso R . . . . . H1051 H 0.3280 0.55486 0.8191 0.0436 1.0000 Uiso R . . . . . H1061 H 0.4086 0.45545 0.8541 0.0442 1.0000 Uiso R . . . . . H1071 H 0.7622 0.42976 0.9339 0.0437 1.0000 Uiso R . . . . . H1081 H 1.0370 0.49359 0.8493 0.0458 1.0000 Uiso R . . . . . H1091 H 0.9535 0.60060 0.8157 0.0444 1.0000 Uiso R . . . . . H1111 H 0.4240 0.56849 1.0302 0.0437 1.0000 Uiso R . . . . . H1131 H 0.6890 0.45810 0.4515 0.0618 1.0000 Uiso R . . . . . H1132 H 0.8194 0.51120 0.5312 0.0618 1.0000 Uiso R . . . . . H1133 H 0.6308 0.53068 0.4296 0.0618 1.0000 Uiso R . . . . . H1141 H 0.3181 0.43238 0.5158 0.0604 1.0000 Uiso R . . . . . H1142 H 0.2100 0.47119 0.6329 0.0604 1.0000 Uiso R . . . . . H1143 H 0.2459 0.50378 0.4923 0.0604 1.0000 Uiso R . . . . . H1151 H 0.8100 0.51843 1.2322 0.0553 1.0000 Uiso R . . . . . H1152 H 0.9654 0.52435 1.1083 0.0553 1.0000 Uiso R . . . . . H1153 H 0.8930 0.45647 1.1592 0.0553 1.0000 Uiso R . . . . . H1161 H 0.4418 0.48493 1.2029 0.0565 1.0000 Uiso R . . . . . H1162 H 0.5254 0.42218 1.1332 0.0565 1.0000 Uiso R . . . . . H1163 H 0.3511 0.46570 1.0595 0.0565 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 0.0564(11) 0.0554(12) 0.0372(10) -0.0088(8) 0.0019(7) 0.0013(9) O2 0.0556(10) 0.0333(9) 0.0331(9) -0.0004(7) 0.0070(7) -0.0020(7) O3 0.0570(11) 0.0355(9) 0.0367(9) -0.0021(7) 0.0077(7) -0.0050(8) O101 0.0572(11) 0.0556(12) 0.0380(11) -0.0095(8) 0.0052(8) -0.0048(9) O102 0.0540(10) 0.0333(9) 0.0360(9) 0.0003(7) -0.0020(7) 0.0017(8) O103 0.0592(11) 0.0361(9) 0.0323(8) -0.0011(7) 0.0027(7) 0.0080(8) C1 0.0361(12) 0.0442(14) 0.0382(14) -0.0045(11) -0.0027(9) -0.0018(10) C2 0.0537(15) 0.0383(13) 0.0443(14) -0.0068(11) -0.0008(11) 0.0031(11) C3 0.0491(14) 0.0349(13) 0.0398(13) 0.0002(10) 0.0005(10) -0.0002(10) C4 0.0368(12) 0.0318(12) 0.0340(12) -0.0010(9) 0.0019(9) 0.0015(9) C5 0.0348(12) 0.0366(12) 0.0310(11) -0.0017(10) 0.0008(9) -0.0015(9) C6 0.0427(13) 0.0322(12) 0.0322(12) 0.0004(9) 0.0011(9) 0.0012(10) C7 0.0411(13) 0.0325(12) 0.0375(12) 0.0009(9) 0.0049(10) -0.0040(10) C8 0.0352(12) 0.0474(15) 0.0338(12) -0.0031(10) -0.0009(9) -0.0042(10) C9 0.0383(12) 0.0405(13) 0.0324(12) -0.0014(10) 0.0009(9) 0.0043(10) C10 0.0402(13) 0.0376(12) 0.0320(12) 0.0013(9) 0.0014(9) 0.0000(10) C11 0.0312(11) 0.0392(13) 0.0334(12) -0.0003(9) -0.0016(9) 0.0013(10) C12 0.0458(13) 0.0358(13) 0.0356(12) -0.0012(9) 0.0064(10) -0.0004(10) C13 0.0559(16) 0.0489(15) 0.0454(15) -0.0024(12) -0.0010(11) -0.0019(13) C14 0.0528(16) 0.0447(15) 0.0496(15) -0.0032(12) 0.0103(11) 0.0056(12) C15 0.0473(14) 0.0505(15) 0.0372(13) 0.0016(11) 0.0052(10) -0.0032(11) C16 0.0498(15) 0.0457(15) 0.0436(14) 0.0068(11) -0.0027(11) 0.0035(11) C101 0.0391(13) 0.0424(14) 0.0403(14) -0.0061(10) 0.0086(10) 0.0009(11) C102 0.0529(15) 0.0355(13) 0.0470(14) -0.0067(11) 0.0065(11) -0.0005(11) C103 0.0482(14) 0.0329(13) 0.0447(13) -0.0034(10) 0.0022(11) 0.0018(11) C104 0.0370(12) 0.0344(12) 0.0328(12) -0.0011(9) 0.0037(9) 0.0013(9) C105 0.0349(12) 0.0394(13) 0.0345(12) -0.0025(10) 0.0034(9) 0.0045(10) C106 0.0404(13) 0.0351(12) 0.0348(12) -0.0004(9) 0.0066(9) -0.0008(9) C107 0.0394(12) 0.0341(12) 0.0355(12) -0.0007(9) 0.0054(9) 0.0029(9) C108 0.0331(11) 0.0478(15) 0.0333(12) -0.0001(10) 0.0063(9) 0.0041(10) C109 0.0375(12) 0.0411(13) 0.0326(12) 0.0008(10) 0.0060(9) -0.0038(10) C110 0.0397(12) 0.0366(12) 0.0361(12) 0.0008(10) 0.0064(9) -0.0004(10) C111 0.0334(11) 0.0399(13) 0.0361(12) -0.0028(10) 0.0071(9) -0.0016(10) C112 0.0503(13) 0.0347(13) 0.0322(12) -0.0012(9) 0.0015(10) 0.0006(11) C113 0.0631(17) 0.0477(15) 0.0431(14) 0.0041(12) 0.0075(12) 0.0023(14) C114 0.0596(17) 0.0438(15) 0.0473(15) 0.0006(11) -0.0028(12) -0.0049(12) C115 0.0497(14) 0.0505(15) 0.0379(13) -0.0005(11) 0.0036(10) 0.0033(12) C116 0.0504(15) 0.0459(15) 0.0443(14) 0.0033(11) 0.0133(11) -0.0061(11) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.0034(17) 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 . C1 . 1.218(3) yes O2 . C5 . 1.428(3) yes O2 . C12 . 1.420(3) yes O3 . C6 . 1.429(3) yes O3 . C12 . 1.424(3) yes O101 . C101 . 1.211(3) yes O102 . C105 . 1.429(3) yes O102 . C112 . 1.426(3) yes O103 . C106 . 1.431(3) yes O103 . C112 . 1.427(3) yes C1 . C2 . 1.512(4) yes C1 . C11 . 1.513(3) yes C2 . C3 . 1.535(3) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.527(3) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . C5 . 1.532(3) yes C4 . C9 . 1.512(3) yes C4 . C11 . 1.557(3) yes C5 . C6 . 1.542(3) yes C5 . H51 . 1.000 no C6 . C7 . 1.536(3) yes C6 . H61 . 1.000 no C7 . C8 . 1.504(3) yes C7 . C10 . 1.570(3) yes C7 . H71 . 1.000 no C8 . C9 . 1.323(3) yes C8 . H81 . 1.000 no C9 . H91 . 1.000 no C10 . C11 . 1.555(3) yes C10 . C15 . 1.537(3) yes C10 . C16 . 1.535(3) yes C11 . H111 . 1.000 no C12 . C13 . 1.503(4) yes C12 . C14 . 1.517(4) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 1.000 no C15 . H151 . 1.000 no C15 . H152 . 1.000 no C15 . H153 . 1.000 no C16 . H161 . 1.000 no C16 . H162 . 1.000 no C16 . H163 . 1.000 no C101 . C102 . 1.518(4) yes C101 . C111 . 1.521(3) yes C102 . C103 . 1.536(3) yes C102 . H1021 . 1.000 no C102 . H1022 . 1.000 no C103 . C104 . 1.526(3) yes C103 . H1031 . 1.000 no C103 . H1032 . 1.000 no C104 . C105 . 1.527(3) yes C104 . C109 . 1.511(3) yes C104 . C111 . 1.556(3) yes C105 . C106 . 1.543(3) yes C105 . H1051 . 1.000 no C106 . C107 . 1.541(3) yes C106 . H1061 . 1.000 no C107 . C108 . 1.508(3) yes C107 . C110 . 1.561(3) yes C107 . H1071 . 1.000 no C108 . C109 . 1.324(3) yes C108 . H1081 . 1.000 no C109 . H1091 . 1.000 no C110 . C111 . 1.559(3) yes C110 . C115 . 1.527(3) yes C110 . C116 . 1.536(3) yes C111 . H1111 . 1.000 no C112 . C113 . 1.506(4) yes C112 . C114 . 1.517(4) yes C113 . H1131 . 1.000 no C113 . H1132 . 1.000 no C113 . H1133 . 1.000 no C114 . H1141 . 1.000 no C114 . H1142 . 1.000 no C114 . H1143 . 1.000 no C115 . H1151 . 1.000 no C115 . H1152 . 1.000 no C115 . H1153 . 1.000 no C116 . H1161 . 1.000 no C116 . H1162 . 1.000 no C116 . H1163 . 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 C5 . O2 . C12 . 108.06(16) yes C6 . O3 . C12 . 107.70(18) yes C105 . O102 . C112 . 108.62(16) yes C106 . O103 . C112 . 108.08(17) yes O1 . C1 . C2 . 125.1(2) yes O1 . C1 . C11 . 126.3(2) yes C2 . C1 . C11 . 108.56(19) yes C1 . C2 . C3 . 105.4(2) yes C1 . C2 . H21 . 110.5 no C3 . C2 . H21 . 110.5 no C1 . C2 . H22 . 110.5 no C3 . C2 . H22 . 110.5 no H21 . C2 . H22 . 109.5 no C2 . C3 . C4 . 102.88(19) yes C2 . C3 . H31 . 111.1 no C4 . C3 . H31 . 111.1 no C2 . C3 . H32 . 111.1 no C4 . C3 . H32 . 111.1 no H31 . C3 . H32 . 109.5 no C3 . C4 . C5 . 117.96(19) yes C3 . C4 . C9 . 113.69(19) yes C5 . C4 . C9 . 107.35(18) yes C3 . C4 . C11 . 103.02(18) yes C5 . C4 . C11 . 105.19(17) yes C9 . C4 . C11 . 108.93(18) yes C4 . C5 . O2 . 112.23(18) yes C4 . C5 . C6 . 108.67(18) yes O2 . C5 . C6 . 104.89(17) yes C4 . C5 . H51 . 110.3 no O2 . C5 . H51 . 110.3 no C6 . C5 . H51 . 110.3 no C5 . C6 . O3 . 104.55(18) yes C5 . C6 . C7 . 110.77(19) yes O3 . C6 . C7 . 108.99(18) yes C5 . C6 . H61 . 110.8 no O3 . C6 . H61 . 110.8 no C7 . C6 . H61 . 110.8 no C6 . C7 . C8 . 106.49(19) yes C6 . C7 . C10 . 110.35(18) yes C8 . C7 . C10 . 107.70(18) yes C6 . C7 . H71 . 110.7 no C8 . C7 . H71 . 110.7 no C10 . C7 . H71 . 110.7 no C7 . C8 . C9 . 114.8(2) yes C7 . C8 . H81 . 122.6 no C9 . C8 . H81 . 122.6 no C4 . C9 . C8 . 114.4(2) yes C4 . C9 . H91 . 122.8 no C8 . C9 . H91 . 122.8 no C7 . C10 . C11 . 105.28(17) yes C7 . C10 . C15 . 107.77(19) yes C11 . C10 . C15 . 113.6(2) yes C7 . C10 . C16 . 110.7(2) yes C11 . C10 . C16 . 111.14(19) yes C15 . C10 . C16 . 108.3(2) yes C10 . C11 . C4 . 112.61(18) yes C10 . C11 . C1 . 121.77(19) yes C4 . C11 . C1 . 103.62(18) yes C10 . C11 . H111 . 105.9 no C4 . C11 . H111 . 105.9 no C1 . C11 . H111 . 105.9 no O3 . C12 . O2 . 105.83(17) yes O3 . C12 . C13 . 108.2(2) yes O2 . C12 . C13 . 108.4(2) yes O3 . C12 . C14 . 109.8(2) yes O2 . C12 . C14 . 111.4(2) yes C13 . C12 . C14 . 112.9(2) yes C12 . C13 . H131 . 109.5 no C12 . C13 . H132 . 109.5 no H131 . C13 . H132 . 109.5 no C12 . C13 . H133 . 109.5 no H131 . C13 . H133 . 109.5 no H132 . C13 . H133 . 109.5 no C12 . C14 . H141 . 109.5 no C12 . C14 . H142 . 109.5 no H141 . C14 . H142 . 109.5 no C12 . C14 . H143 . 109.4 no H141 . C14 . H143 . 109.5 no H142 . C14 . H143 . 109.5 no C10 . C15 . H151 . 109.4 no C10 . C15 . H152 . 109.5 no H151 . C15 . H152 . 109.5 no C10 . C15 . H153 . 109.5 no H151 . C15 . H153 . 109.5 no H152 . C15 . H153 . 109.5 no C10 . C16 . H161 . 109.4 no C10 . C16 . H162 . 109.5 no H161 . C16 . H162 . 109.5 no C10 . C16 . H163 . 109.5 no H161 . C16 . H163 . 109.5 no H162 . C16 . H163 . 109.5 no O101 . C101 . C102 . 125.4(2) yes O101 . C101 . C111 . 126.5(2) yes C102 . C101 . C111 . 108.1(2) yes C101 . C102 . C103 . 105.5(2) yes C101 . C102 . H1021 . 110.4 no C103 . C102 . H1021 . 110.4 no C101 . C102 . H1022 . 110.5 no C103 . C102 . H1022 . 110.4 no H1021 . C102 . H1022 . 109.5 no C102 . C103 . C104 . 103.2(2) yes C102 . C103 . H1031 . 111.0 no C104 . C103 . H1031 . 111.0 no C102 . C103 . H1032 . 111.0 no C104 . C103 . H1032 . 111.0 no H1031 . C103 . H1032 . 109.5 no C103 . C104 . C105 . 117.8(2) yes C103 . C104 . C109 . 113.6(2) yes C105 . C104 . C109 . 107.79(18) yes C103 . C104 . C111 . 103.14(19) yes C105 . C104 . C111 . 105.10(18) yes C109 . C104 . C111 . 108.69(18) yes C104 . C105 . O102 . 112.30(18) yes C104 . C105 . C106 . 108.66(18) yes O102 . C105 . C106 . 104.71(17) yes C104 . C105 . H1051 . 110.3 no O102 . C105 . H1051 . 110.3 no C106 . C105 . H1051 . 110.4 no C105 . C106 . O103 . 104.54(18) yes C105 . C106 . C107 . 110.66(19) yes O103 . C106 . C107 . 109.16(18) yes C105 . C106 . H1061 . 110.8 no O103 . C106 . H1061 . 110.8 no C107 . C106 . H1061 . 110.8 no C106 . C107 . C108 . 106.13(18) yes C106 . C107 . C110 . 110.80(19) yes C108 . C107 . C110 . 108.02(19) yes C106 . C107 . H1071 . 110.6 no C108 . C107 . H1071 . 110.6 no C110 . C107 . H1071 . 110.6 no C107 . C108 . C109 . 114.5(2) yes C107 . C108 . H1081 . 122.8 no C109 . C108 . H1081 . 122.8 no C104 . C109 . C108 . 114.5(2) yes C104 . C109 . H1091 . 122.7 no C108 . C109 . H1091 . 122.8 no C107 . C110 . C111 . 105.00(18) yes C107 . C110 . C115 . 108.63(19) yes C111 . C110 . C115 . 113.6(2) yes C107 . C110 . C116 . 111.2(2) yes C111 . C110 . C116 . 110.49(19) yes C115 . C110 . C116 . 107.9(2) yes C104 . C111 . C110 . 112.73(18) yes C104 . C111 . C101 . 103.79(19) yes C110 . C111 . C101 . 121.5(2) yes C104 . C111 . H1111 . 105.9 no C110 . C111 . H1111 . 105.9 no C101 . C111 . H1111 . 105.9 no O103 . C112 . O102 . 105.19(17) yes O103 . C112 . C113 . 109.0(2) yes O102 . C112 . C113 . 108.1(2) yes O103 . C112 . C114 . 109.9(2) yes O102 . C112 . C114 . 111.1(2) yes C113 . C112 . C114 . 113.2(2) yes C112 . C113 . H1131 . 109.5 no C112 . C113 . H1132 . 109.5 no H1131 . C113 . H1132 . 109.5 no C112 . C113 . H1133 . 109.5 no H1131 . C113 . H1133 . 109.5 no H1132 . C113 . H1133 . 109.5 no C112 . C114 . H1141 . 109.5 no C112 . C114 . H1142 . 109.5 no H1141 . C114 . H1142 . 109.5 no C112 . C114 . H1143 . 109.4 no H1141 . C114 . H1143 . 109.5 no H1142 . C114 . H1143 . 109.5 no C110 . C115 . H1151 . 109.5 no C110 . C115 . H1152 . 109.5 no H1151 . C115 . H1152 . 109.5 no C110 . C115 . H1153 . 109.5 no H1151 . C115 . H1153 . 109.5 no H1152 . C115 . H1153 . 109.5 no C110 . C116 . H1161 . 109.4 no C110 . C116 . H1162 . 109.5 no H1161 . C116 . H1162 . 109.5 no C110 . C116 . H1163 . 109.5 no H1161 . C116 . H1163 . 109.5 no H1162 . C116 . H1163 . 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 C101 3.162(3) . 1_554 no O1 O101 3.386(3) . 1_554 no O1 O101 3.399(3) . 1_454 no O1 C102 3.454(3) . 1_554 no O1 C102 3.463(3) . 1_454 no O1 C101 3.505(3) . 1_454 no O1 C111 3.520(3) . 1_554 no O101 C1 3.156(3) . 1_656 no O101 C2 3.437(3) . 1_656 no O101 C2 3.474(3) . 1_556 no O101 C11 3.489(3) . 1_656 no O101 C1 3.509(3) . 1_556 no O103 C7 3.481(3) . 2_646 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 C1 C2 C3 . . . . -168.0(2) no O1 C1 C11 C4 . . . . -166.9(2) no O1 C1 C11 C10 . . . . -38.9(4) no O2 C5 C4 C3 . . . . 70.2(2) no O2 C5 C4 C9 . . . . -59.8(2) no O2 C5 C4 C11 . . . . -175.7(2) no O2 C5 C6 O3 . . . . 2.1(2) no O2 C5 C6 C7 . . . . 119.4(2) no O2 C12 O3 C6 . . . . 30.3(2) no O3 C6 C5 C4 . . . . -118.1(2) no O3 C6 C7 C8 . . . . 59.9(2) no O3 C6 C7 C10 . . . . 176.5(2) no O3 C12 O2 C5 . . . . -28.8(2) no O101 C101 C102 C103 . . . . -169.0(2) no O101 C101 C111 C104 . . . . -166.2(2) no O101 C101 C111 C110 . . . . -38.1(4) no O102 C105 C104 C103 . . . . 70.1(3) no O102 C105 C104 C109 . . . . -60.0(2) no O102 C105 C104 C111 . . . . -175.8(2) no O102 C105 C106 O103 . . . . 2.6(2) no O102 C105 C106 C107 . . . . 120.0(2) no O102 C112 O103 C106 . . . . 30.1(2) no O103 C106 C105 C104 . . . . -117.6(2) no O103 C106 C107 C108 . . . . 59.2(2) no O103 C106 C107 C110 . . . . 176.3(2) no O103 C112 O102 C105 . . . . -28.4(2) no C1 C2 C3 C4 . . . . -31.5(2) no C1 C11 C4 C3 . . . . -34.7(2) no C1 C11 C4 C5 . . . . -158.9(2) no C1 C11 C4 C9 . . . . 86.3(2) no C1 C11 C10 C7 . . . . -132.7(2) no C1 C11 C10 C15 . . . . -15.0(3) no C1 C11 C10 C16 . . . . 107.4(2) no C2 C1 C11 C4 . . . . 15.3(2) no C2 C1 C11 C10 . . . . 143.3(2) no C2 C3 C4 C5 . . . . 156.1(2) no C2 C3 C4 C9 . . . . -76.9(2) no C2 C3 C4 C11 . . . . 40.8(2) no C3 C2 C1 C11 . . . . 9.8(3) no C3 C4 C5 C6 . . . . -174.3(2) no C3 C4 C9 C8 . . . . 169.7(2) no C3 C4 C11 C10 . . . . -168.2(2) no C4 C5 O2 C12 . . . . 134.0(2) no C4 C5 C6 C7 . . . . -0.9(2) no C4 C9 C8 C7 . . . . -1.3(3) no C4 C11 C10 C7 . . . . -8.8(2) no C4 C11 C10 C15 . . . . 108.9(2) no C4 C11 C10 C16 . . . . -128.7(2) no C5 O2 C12 C13 . . . . -144.7(2) no C5 O2 C12 C14 . . . . 90.5(2) no C5 C4 C9 C8 . . . . -58.0(2) no C5 C4 C11 C10 . . . . 67.7(2) no C5 C6 O3 C12 . . . . -19.6(2) no C5 C6 C7 C8 . . . . -54.6(2) no C5 C6 C7 C10 . . . . 62.0(2) no C6 O3 C12 C13 . . . . 146.3(2) no C6 O3 C12 C14 . . . . -90.1(2) no C6 C5 O2 C12 . . . . 16.2(2) no C6 C5 C4 C9 . . . . 55.8(2) no C6 C5 C4 C11 . . . . -60.2(2) no C6 C7 C8 C9 . . . . 58.5(2) no C6 C7 C10 C11 . . . . -54.5(2) no C6 C7 C10 C15 . . . . -176.1(2) no C6 C7 C10 C16 . . . . 65.7(2) no C7 C6 O3 C12 . . . . -138.1(2) no C8 C7 C10 C11 . . . . 61.3(2) no C8 C7 C10 C15 . . . . -60.2(2) no C8 C7 C10 C16 . . . . -178.4(2) no C8 C9 C4 C11 . . . . 55.5(3) no C9 C4 C11 C10 . . . . -47.1(2) no C9 C8 C7 C10 . . . . -59.9(3) no C101 C102 C103 C104 . . . . -30.8(2) no C101 C111 C104 C103 . . . . -34.7(2) no C101 C111 C104 C105 . . . . -158.7(2) no C101 C111 C104 C109 . . . . 86.1(2) no C101 C111 C110 C107 . . . . -133.0(2) no C101 C111 C110 C115 . . . . -14.4(3) no C101 C111 C110 C116 . . . . 107.0(2) no C102 C101 C111 C104 . . . . 15.7(2) no C102 C101 C111 C110 . . . . 143.8(2) no C102 C103 C104 C105 . . . . 155.6(2) no C102 C103 C104 C109 . . . . -77.0(2) no C102 C103 C104 C111 . . . . 40.4(2) no C103 C102 C101 C111 . . . . 9.1(3) no C103 C104 C105 C106 . . . . -174.6(2) no C103 C104 C109 C108 . . . . 170.0(2) no C103 C104 C111 C110 . . . . -168.1(2) no C104 C105 O102 C112 . . . . 133.4(2) no C104 C105 C106 C107 . . . . -0.2(2) no C104 C109 C108 C107 . . . . -2.0(3) no C104 C111 C110 C107 . . . . -8.9(2) no C104 C111 C110 C115 . . . . 109.6(2) no C104 C111 C110 C116 . . . . -128.9(2) no C105 O102 C112 C113 . . . . -144.7(2) no C105 O102 C112 C114 . . . . 90.5(2) no C105 C104 C109 C108 . . . . -57.6(2) no C105 C104 C111 C110 . . . . 68.0(2) no C105 C106 O103 C112 . . . . -20.0(2) no C105 C106 C107 C108 . . . . -55.3(2) no C105 C106 C107 C110 . . . . 61.8(2) no C106 O103 C112 C113 . . . . 145.8(2) no C106 O103 C112 C114 . . . . -89.6(2) no C106 C105 O102 C112 . . . . 15.7(2) no C106 C105 C104 C109 . . . . 55.3(2) no C106 C105 C104 C111 . . . . -60.5(2) no C106 C107 C108 C109 . . . . 59.0(2) no C106 C107 C110 C111 . . . . -54.3(2) no C106 C107 C110 C115 . . . . -176.2(2) no C106 C107 C110 C116 . . . . 65.2(3) no C107 C106 O103 C112 . . . . -138.4(2) no C108 C107 C110 C111 . . . . 61.6(2) no C108 C107 C110 C115 . . . . -60.3(3) no C108 C107 C110 C116 . . . . -178.9(2) no C108 C109 C104 C111 . . . . 55.8(3) no C109 C104 C111 C110 . . . . -47.2(2) no C109 C108 C107 C110 . . . . -59.9(3) no data_ban0815 _database_code_depnum_ccdc_archive 'CCDC 747032' _audit_creation_date 08-07-01 _audit_creation_method CRYSTALS_ver_12.18 _audit_update_record ; 2008-07-01 - Report on C18 H18 O3 by Anthony C. Willis for Kerrie Austin and Martin Banwell 2008-07-01 - passes checkcif tests with warnings ; _oxford_structure_analysis_title '6301249 ban0815' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.1347(6) _cell_length_b 6.1641(4) _cell_length_c 21.3826(15) _cell_angle_alpha 90 _cell_angle_beta 98.820(3) _cell_angle_gamma 90 _cell_volume 1189.76(14) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,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' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 '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 = C24 H28 N2 O8 # Dc = 1.32 Fooo = 500.00 Mu = 1.00 M = 472.49 # Found Formula = C24 H28 N2 O8 # Dc = 1.32 FOOO = 500.00 Mu = 1.00 M = 472.49 _chemical_formula_sum 'C24 H28 N2 O8' _chemical_formula_moiety 'C24 H28 N2 O8' _chemical_compound_source local _chemical_formula_weight 472.49 _cell_measurement_reflns_used 115021 _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 0.20 _exptl_crystal_size_max 0.43 _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 0.100 # 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 0 0 0.100 -1 0 0 0.100 0 1 0 0.180 0 -1 0 0.250 0 0 1 0.001 0 0 -1 0.025 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_T_max 0.997 _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 0.5 deg at rate 130 sec/frame, crystal-detector distance 35mm, multiple scan sets so over 90 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, 1997)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _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) ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 14469 _reflns_number_total 2322 _diffrn_reflns_av_R_equivalents 0.090 # Number of reflections with Friedels Law is 2322 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2123 _diffrn_reflns_theta_min 2.586 _diffrn_reflns_theta_max 25.117 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.117 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _oxford_diffrn_Wilson_B_factor 3.47 _oxford_diffrn_Wilson_scale 1.83 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.30 _refine_diff_density_max 0.36 _refine_ls_number_reflns 1661 _refine_ls_number_restraints 1 _refine_ls_number_parameters 308 #_refine_ls_R_factor_ref 0.0822 _refine_ls_wR_factor_ref 0.0767 _refine_ls_goodness_of_fit_ref 1.1501 #_reflns_number_all 2308 _refine_ls_R_factor_all 0.1111 _refine_ls_wR_factor_all 0.1035 # 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 1661 _refine_ls_R_factor_gt 0.0822 _refine_ls_wR_factor_gt 0.0767 _refine_ls_shift/su_max 0.003390 # 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 syn _refine_ls_abs_structure_details ; The enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure. ; _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: 2.26 0.991 1.81 ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~24~H~28~N~2~O~8~ is reported. ; _publ_section_comment #Text of the paper ; The compound is enantiometrically pure but the anomolous dispersion terms are very low for all elements in the structure and so the absolute configuration can not be determined in this experiment. Consequently Friedel-pair reflections have been averaged and the Flack parameter has not been refined. The absolute configuration of the molecule has been assigned on the basis of the synthetic precursors. The crystallographic asymmetric unit consists of one molecule of C~24~H~28~N~2~O~8~. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; Crystals of this compound were obtained as very thin fragile plates which diffracted only weakly. Even with long exposure times, the number of reflections with intensities above background is limited. The observation:parameter ratio is therefore lower than we would like but the identity of the compound is clearly established, nonetheless. There do not appear to be any significant refinement anomalies. Streaks in synthesised "precession photographs" suggested that twinning might occur perpendicular to c*. Addition of such a twinning component aided refinement considerably. Hydrogen atoms were included at calculated positions and ride on the atom to which they are attached. The final difference electron density map shows many peaks with similar intensity which are located randomly through the structure. ; _publ_section_exptl_prep ; The compound was prepared by KAA and recrystallized from ethylacetate/hexane. The sample ID is KATV-07-105. ; #**************************************************************************** # Insert your own references if required - in alphabetical order _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 0.1296(7) 0.5579(12) 0.4367(2) 0.0610 1.0000 Uani . . . . . . O2 O 0.3752(6) 0.4873(11) 0.4407(2) 0.0545 1.0000 Uani . . . . . . O3 O 0.3450(5) 0.4770(9) 0.1582(2) 0.0412 1.0000 Uani . . . . . . O4 O 0.4413(6) 0.7491(11) 0.1087(2) 0.0539 1.0000 Uani . . . . . . O5 O 0.1052(6) -0.1242(10) 0.0395(3) 0.0536 1.0000 Uani . . . . . . O6 O 0.0750(7) -0.1246(10) -0.0634(3) 0.0576 1.0000 Uani . . . . . . O7 O 0.2730(6) 0.4701(12) -0.1737(3) 0.0584 1.0000 Uani . . . . . . O8 O 0.3753(7) 0.7343(13) -0.1202(3) 0.0660 1.0000 Uani . . . . . . N1 N 0.1228(6) -0.0453(11) -0.0124(3) 0.0436 1.0000 Uani . . . . . . N2 N 0.3158(7) 0.5567(13) -0.1250(3) 0.0443 1.0000 Uani . . . . . . C1 C 0.3848(9) 0.5854(15) 0.2198(3) 0.0482 1.0000 Uani . . . . . . C2 C 0.5434(7) 0.5330(17) 0.2506(4) 0.0565 1.0000 Uani . . . . . . C3 C 0.5374(8) 0.5161(17) 0.3218(4) 0.0561 1.0000 Uani . . . . . . C4 C 0.3764(8) 0.5707(15) 0.3299(3) 0.0427 1.0000 Uani . . . . . . C5 C 0.3454(10) 0.7994(13) 0.3416(4) 0.0492 1.0000 Uani . . . . . . C6 C 0.2047(9) 0.8500(15) 0.3406(4) 0.0481 1.0000 Uani . . . . . . C7 C 0.0949(8) 0.6655(15) 0.3260(4) 0.0472 1.0000 Uani . . . . . . C8 C 0.1461(8) 0.4874(15) 0.3734(3) 0.0478 1.0000 Uani . . . . . . C9 C 0.3114(8) 0.4334(13) 0.3782(3) 0.0441 1.0000 Uani . . . . . . C10 C 0.1191(8) 0.5803(14) 0.2581(3) 0.0393 1.0000 Uani . . . . . . C11 C 0.2862(7) 0.5061(13) 0.2646(3) 0.0395 1.0000 Uani . . . . . . C12 C 0.2588(10) 0.4866(16) 0.4788(3) 0.0562 1.0000 Uani . . . . . . C13 C 0.2323(14) 0.253(2) 0.5007(5) 0.0803 1.0000 Uani . . . . . . C14 C 0.2902(13) 0.6428(19) 0.5316(5) 0.0747 1.0000 Uani . . . . . . C15 C -0.0588(10) 0.734(2) 0.3283(4) 0.0644 1.0000 Uani . . . . . . C16 C 0.0181(9) 0.3867(15) 0.2344(4) 0.0508 1.0000 Uani . . . . . . C17 C 0.0860(9) 0.7630(16) 0.2080(3) 0.0535 1.0000 Uani . . . . . . C18 C 0.3780(8) 0.5798(15) 0.1075(3) 0.0396 1.0000 Uani . . . . . . C19 C 0.3270(7) 0.4545(13) 0.0482(3) 0.0381 1.0000 Uani . . . . . . C20 C 0.2547(7) 0.2571(12) 0.0473(3) 0.0346 1.0000 Uani . . . . . . C21 C 0.2049(8) 0.1603(12) -0.0101(3) 0.0364 1.0000 Uani . . . . . . C22 C 0.2269(7) 0.2481(12) -0.0679(4) 0.0388 1.0000 Uani . . . . . . C23 C 0.2987(8) 0.4485(14) -0.0657(3) 0.0392 1.0000 Uani . . . . . . C24 C 0.3506(7) 0.5550(13) -0.0083(3) 0.0402 1.0000 Uani . . . . . . H11 H 0.3732 0.7459 0.2143 0.0572 1.0000 Uiso R . . . . . H21 H 0.6125 0.6514 0.2420 0.0676 1.0000 Uiso R . . . . . H22 H 0.5767 0.3925 0.2341 0.0676 1.0000 Uiso R . . . . . H31 H 0.6076 0.6220 0.3458 0.0670 1.0000 Uiso R . . . . . H32 H 0.5635 0.3658 0.3372 0.0670 1.0000 Uiso R . . . . . H51 H 0.4260 0.9102 0.3498 0.0602 1.0000 Uiso R . . . . . H61 H 0.1724 1.0009 0.3490 0.0586 1.0000 Uiso R . . . . . H81 H 0.0859 0.3535 0.3623 0.0584 1.0000 Uiso R . . . . . H91 H 0.3253 0.2756 0.3701 0.0527 1.0000 Uiso R . . . . . H111 H 0.2862 0.3440 0.2624 0.0469 1.0000 Uiso R . . . . . H131 H 0.3215 0.202 0.5300 0.0957 1.0000 Uiso R . . . . . H132 H 0.1441 0.251 0.5232 0.0957 1.0000 Uiso R . . . . . H133 H 0.2143 0.155 0.4630 0.0957 1.0000 Uiso R . . . . . H141 H 0.3799 0.5945 0.5612 0.0903 1.0000 Uiso R . . . . . H142 H 0.2034 0.6501 0.5549 0.0903 1.0000 Uiso R . . . . . H143 H 0.3087 0.7895 0.5145 0.0903 1.0000 Uiso R . . . . . H151 H -0.1269 0.608 0.3184 0.0768 1.0000 Uiso R . . . . . H152 H -0.0667 0.790 0.3715 0.0768 1.0000 Uiso R . . . . . H153 H -0.0870 0.852 0.2964 0.0768 1.0000 Uiso R . . . . . H161 H 0.0384 0.3408 0.1917 0.0610 1.0000 Uiso R . . . . . H162 H 0.0386 0.2629 0.2647 0.0610 1.0000 Uiso R . . . . . H163 H -0.0881 0.4311 0.2314 0.0610 1.0000 Uiso R . . . . . H171 H 0.1017 0.7066 0.1657 0.0635 1.0000 Uiso R . . . . . H172 H 0.1539 0.8883 0.2201 0.0635 1.0000 Uiso R . . . . . H173 H -0.0191 0.8117 0.2058 0.0635 1.0000 Uiso R . . . . . H201 H 0.2387 0.1858 0.0877 0.0421 1.0000 Uiso R . . . . . H221 H 0.1931 0.1718 -0.1089 0.0472 1.0000 Uiso R . . . . . H241 H 0.4027 0.6979 -0.0078 0.0493 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 0.072(4) 0.078(4) 0.036(3) -0.003(3) 0.019(3) 0.007(3) O2 0.052(3) 0.072(4) 0.038(3) 0.006(3) 0.003(2) 0.006(3) O3 0.039(2) 0.053(3) 0.034(3) -0.012(3) 0.0105(19) -0.008(3) O4 0.058(3) 0.058(4) 0.049(3) -0.010(3) 0.017(3) -0.026(3) O5 0.053(3) 0.048(3) 0.060(4) 0.003(3) 0.008(3) -0.006(3) O6 0.060(4) 0.051(3) 0.059(4) -0.007(3) 0.000(3) -0.018(3) O7 0.056(3) 0.078(4) 0.041(3) 0.010(3) 0.005(2) -0.021(3) O8 0.070(4) 0.079(5) 0.047(3) 0.016(3) 0.002(3) -0.024(4) N1 0.038(3) 0.042(4) 0.051(4) 0.009(4) 0.009(3) 0.005(3) N2 0.036(3) 0.060(5) 0.039(4) 0.005(3) 0.009(3) -0.007(3) C1 0.052(4) 0.052(5) 0.040(4) -0.012(4) 0.002(3) -0.010(4) C2 0.027(4) 0.089(7) 0.053(4) -0.008(5) 0.005(3) -0.001(4) C3 0.037(4) 0.081(7) 0.049(4) -0.003(5) 0.005(3) 0.002(4) C4 0.036(4) 0.059(5) 0.033(4) -0.003(4) 0.006(3) 0.001(4) C5 0.061(5) 0.054(6) 0.037(4) -0.002(4) 0.017(4) -0.012(4) C6 0.048(5) 0.050(5) 0.049(4) -0.002(4) 0.014(4) 0.007(4) C7 0.047(5) 0.054(5) 0.043(4) -0.008(4) 0.014(3) -0.006(4) C8 0.054(4) 0.050(5) 0.042(4) -0.010(4) 0.016(3) -0.004(4) C9 0.053(4) 0.046(5) 0.033(4) 0.001(3) 0.004(3) -0.003(4) C10 0.032(3) 0.051(4) 0.036(4) -0.005(4) 0.007(3) 0.003(3) C11 0.035(4) 0.037(4) 0.045(4) 0.000(4) 0.002(3) -0.004(3) C12 0.069(5) 0.067(6) 0.029(4) 0.000(4) -0.002(3) -0.005(5) C13 0.109(8) 0.075(7) 0.054(5) 0.017(6) 0.008(5) -0.007(7) C14 0.088(7) 0.083(7) 0.053(5) -0.010(5) 0.015(5) -0.012(6) C15 0.057(5) 0.095(7) 0.040(4) -0.009(5) 0.005(4) 0.020(5) C16 0.042(4) 0.060(5) 0.050(5) -0.005(4) 0.007(4) -0.001(4) C17 0.047(4) 0.067(5) 0.044(4) -0.003(4) 0.001(3) 0.017(4) C18 0.039(4) 0.056(5) 0.027(4) -0.008(4) 0.015(3) 0.001(4) C19 0.034(3) 0.039(4) 0.043(4) -0.005(3) 0.011(3) 0.003(3) C20 0.029(3) 0.042(4) 0.035(4) -0.004(3) 0.010(3) 0.011(3) C21 0.036(4) 0.028(3) 0.047(4) 0.003(3) 0.013(3) 0.004(3) C22 0.032(4) 0.032(4) 0.054(4) -0.005(4) 0.012(3) -0.017(3) C23 0.034(4) 0.051(5) 0.033(4) -0.001(3) 0.005(3) 0.008(4) C24 0.025(3) 0.048(4) 0.050(4) 0.005(4) 0.014(3) -0.003(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.792(4) loop_ _oxford_twin_element_scale_factors 0.858(3) 0.142(3) 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 . C8 . 1.450(9) yes O1 . C12 . 1.440(11) yes O2 . C9 . 1.412(9) yes O2 . C12 . 1.437(10) yes O3 . C1 . 1.472(9) yes O3 . C18 . 1.329(9) yes O4 . C18 . 1.192(10) yes O5 . N1 . 1.243(8) yes O6 . N1 . 1.213(8) yes O7 . N2 . 1.183(9) yes O8 . N2 . 1.219(10) yes N1 . C21 . 1.470(10) yes N2 . C23 . 1.462(10) yes C1 . C2 . 1.531(11) yes C1 . C11 . 1.494(11) yes C1 . H11 . 1.000 no C2 . C3 . 1.536(11) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.545(11) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . C5 . 1.467(12) yes C4 . C9 . 1.523(11) yes C4 . C11 . 1.561(10) yes C5 . C6 . 1.320(12) yes C5 . H51 . 1.000 no C6 . C7 . 1.517(12) yes C6 . H61 . 1.000 no C7 . C8 . 1.518(12) yes C7 . C10 . 1.591(10) yes C7 . C15 . 1.475(11) yes C8 . C9 . 1.535(11) yes C8 . H81 . 1.000 no C9 . H91 . 1.000 no C10 . C11 . 1.579(10) yes C10 . C16 . 1.546(12) yes C10 . C17 . 1.552(12) yes C11 . H111 . 1.000 no C12 . C13 . 1.545(15) yes C12 . C14 . 1.478(13) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 1.000 no C15 . H151 . 1.000 no C15 . H152 . 1.000 no C15 . H153 . 1.000 no C16 . H161 . 1.000 no C16 . H162 . 1.000 no C16 . H163 . 1.000 no C17 . H171 . 1.000 no C17 . H172 . 1.000 no C17 . H173 . 1.000 no C18 . C19 . 1.497(10) yes C19 . C20 . 1.383(11) yes C19 . C24 . 1.403(10) yes C20 . C21 . 1.377(10) yes C20 . H201 . 1.000 no C21 . C22 . 1.392(10) yes C22 . C23 . 1.395(11) yes C22 . H221 . 1.000 no C23 . C24 . 1.409(11) yes C24 . H241 . 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 C8 . O1 . C12 . 107.5(6) yes C9 . O2 . C12 . 107.6(6) yes C1 . O3 . C18 . 117.2(6) yes O5 . N1 . O6 . 124.4(7) yes O5 . N1 . C21 . 116.3(6) yes O6 . N1 . C21 . 119.3(6) yes O8 . N2 . O7 . 124.2(7) yes O8 . N2 . C23 . 116.2(7) yes O7 . N2 . C23 . 119.5(7) yes O3 . C1 . C2 . 112.1(7) yes O3 . C1 . C11 . 109.6(6) yes C2 . C1 . C11 . 106.2(6) yes O3 . C1 . H11 . 109.6 no C2 . C1 . H11 . 109.6 no C11 . C1 . H11 . 109.6 no C1 . C2 . C3 . 105.4(6) yes C1 . C2 . H21 . 110.5 no C3 . C2 . H21 . 110.5 no C1 . C2 . H22 . 110.5 no C3 . C2 . H22 . 110.5 no H21 . C2 . H22 . 109.5 no C2 . C3 . C4 . 106.0(6) yes C2 . C3 . H31 . 110.3 no C4 . C3 . H31 . 110.3 no C2 . C3 . H32 . 110.3 no C4 . C3 . H32 . 110.3 no H31 . C3 . H32 . 109.5 no C3 . C4 . C5 . 116.1(7) yes C3 . C4 . C9 . 115.6(7) yes C5 . C4 . C9 . 108.2(6) yes C3 . C4 . C11 . 103.0(6) yes C5 . C4 . C11 . 108.0(7) yes C9 . C4 . C11 . 105.0(6) yes C4 . C5 . C6 . 115.9(8) yes C4 . C5 . H51 . 122.0 no C6 . C5 . H51 . 122.0 no C5 . C6 . C7 . 115.9(8) yes C5 . C6 . H61 . 122.0 no C7 . C6 . H61 . 122.0 no C6 . C7 . C8 . 106.2(6) yes C6 . C7 . C10 . 104.8(6) yes C8 . C7 . C10 . 107.4(7) yes C6 . C7 . C15 . 112.4(8) yes C8 . C7 . C15 . 112.5(7) yes C10 . C7 . C15 . 113.0(6) yes C7 . C8 . O1 . 109.9(7) yes C7 . C8 . C9 . 113.6(6) yes O1 . C8 . C9 . 104.1(6) yes C7 . C8 . H81 . 109.7 no O1 . C8 . H81 . 109.7 no C9 . C8 . H81 . 109.7 no C8 . C9 . C4 . 108.4(6) yes C8 . C9 . O2 . 105.8(6) yes C4 . C9 . O2 . 111.3(6) yes C8 . C9 . H91 . 110.4 no C4 . C9 . H91 . 110.4 no O2 . C9 . H91 . 110.4 no C7 . C10 . C11 . 106.5(6) yes C7 . C10 . C16 . 113.3(6) yes C11 . C10 . C16 . 109.0(6) yes C7 . C10 . C17 . 110.6(7) yes C11 . C10 . C17 . 110.7(6) yes C16 . C10 . C17 . 106.8(6) yes C4 . C11 . C10 . 112.0(6) yes C4 . C11 . C1 . 101.7(6) yes C10 . C11 . C1 . 121.3(7) yes C4 . C11 . H111 . 107.0 no C10 . C11 . H111 . 107.0 no C1 . C11 . H111 . 107.0 no O1 . C12 . O2 . 104.5(5) yes O1 . C12 . C13 . 108.9(8) yes O2 . C12 . C13 . 109.8(8) yes O1 . C12 . C14 . 108.9(8) yes O2 . C12 . C14 . 110.9(7) yes C13 . C12 . C14 . 113.4(8) yes C12 . C13 . H131 . 109.4 no C12 . C13 . H132 . 109.5 no H131 . C13 . H132 . 109.5 no C12 . C13 . H133 . 109.5 no H131 . C13 . H133 . 109.5 no H132 . C13 . H133 . 109.5 no C12 . C14 . H141 . 109.5 no C12 . C14 . H142 . 109.5 no H141 . C14 . H142 . 109.5 no C12 . C14 . H143 . 109.5 no H141 . C14 . H143 . 109.5 no H142 . C14 . H143 . 109.5 no C7 . C15 . H151 . 109.5 no C7 . C15 . H152 . 109.5 no H151 . C15 . H152 . 109.5 no C7 . C15 . H153 . 109.4 no H151 . C15 . H153 . 109.5 no H152 . C15 . H153 . 109.5 no C10 . C16 . H161 . 109.5 no C10 . C16 . H162 . 109.4 no H161 . C16 . H162 . 109.5 no C10 . C16 . H163 . 109.5 no H161 . C16 . H163 . 109.5 no H162 . C16 . H163 . 109.5 no C10 . C17 . H171 . 109.5 no C10 . C17 . H172 . 109.5 no H171 . C17 . H172 . 109.5 no C10 . C17 . H173 . 109.5 no H171 . C17 . H173 . 109.5 no H172 . C17 . H173 . 109.5 no O3 . C18 . O4 . 124.7(7) yes O3 . C18 . C19 . 111.4(7) yes O4 . C18 . C19 . 123.9(7) yes C18 . C19 . C20 . 123.4(7) yes C18 . C19 . C24 . 115.6(7) yes C20 . C19 . C24 . 120.9(7) yes C19 . C20 . C21 . 119.0(6) yes C19 . C20 . H201 . 120.5 no C21 . C20 . H201 . 120.5 no N1 . C21 . C20 . 120.0(6) yes N1 . C21 . C22 . 116.6(7) yes C20 . C21 . C22 . 123.4(7) yes C21 . C22 . C23 . 116.4(7) yes C21 . C22 . H221 . 121.8 no C23 . C22 . H221 . 121.8 no N2 . C23 . C22 . 119.1(7) yes N2 . C23 . C24 . 118.4(7) yes C22 . C23 . C24 . 122.4(7) yes C23 . C24 . C19 . 117.9(7) yes C23 . C24 . H241 . 121.0 no C19 . C24 . H241 . 121.1 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 O3 O8 3.172(9) . 2_645 no O4 N2 2.899(9) . 2_655 no O4 C23 2.94(1) . 2_655 no O4 O7 3.080(8) . 2_655 no O4 C22 3.280(9) . 2_655 no O4 O5 3.291(7) . 1_565 no O4 O8 3.42(1) . 2_655 no O4 O8 3.58(1) . 2_645 no O5 C21 3.105(9) . 2_545 no O5 C18 3.247(9) . 1_545 no O5 C24 3.268(9) . 1_545 no O5 C22 3.280(9) . 2_545 no O5 C19 3.282(9) . 1_545 no O5 N1 3.323(9) . 2_545 no O5 O6 3.566(9) . 2 no O5 O6 3.570(9) . 2_545 no O5 C20 3.594(8) . 2_545 no O6 C20 3.168(9) . 2_545 no O6 C24 3.274(9) . 1_545 no O6 O8 3.28(1) . 1_545 no O6 C23 3.34(1) . 1_545 no O6 N2 3.36(1) . 1_545 no O6 C21 3.46(1) . 2_545 no O7 C17 3.49(1) . 2_545 no O8 C18 3.08(1) . 2_655 no O8 C19 3.213(9) . 2_655 no O8 C20 3.501(9) . 2_655 no O8 C2 3.51(1) . 2_655 no N1 C24 3.22(1) . 1_545 no N1 C21 3.60(1) . 2_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 C8 C7 C6 . . . . 67.1(8) no O1 C8 C7 C10 . . . . 178.8(6) no O1 C8 C7 C15 . . . . -56.2(9) no O1 C8 C9 O2 . . . . -3.1(8) no O1 C8 C9 C4 . . . . -122.6(7) no O1 C12 O2 C9 . . . . -32.8(9) no O2 C9 C4 C3 . . . . 71.9(9) no O2 C9 C4 C5 . . . . -60.3(8) no O2 C9 C4 C11 . . . . -175.4(6) no O2 C9 C8 C7 . . . . 116.4(7) no O2 C12 O1 C8 . . . . 30.5(9) no O3 C1 C2 C3 . . . . -143.2(7) no O3 C1 C11 C4 . . . . 161.1(6) no O3 C1 C11 C10 . . . . -73.9(9) no O3 C18 C19 C20 . . . . 0(1) no O3 C18 C19 C24 . . . . 177.1(6) no O4 C18 O3 C1 . . . . 2(1) no O4 C18 C19 C20 . . . . 179.4(7) no O4 C18 C19 C24 . . . . -4(1) no O5 N1 C21 C20 . . . . -1(1) no O5 N1 C21 C22 . . . . 179.1(6) no O6 N1 C21 C20 . . . . 177.4(7) no O6 N1 C21 C22 . . . . -2(1) no O7 N2 C23 C22 . . . . -2(1) no O7 N2 C23 C24 . . . . 180.0(7) no O8 N2 C23 C22 . . . . 177.8(7) no O8 N2 C23 C24 . . . . 0(1) no N1 C21 C20 C19 . . . . -177.7(6) no N1 C21 C22 C23 . . . . 177.0(6) no N2 C23 C22 C21 . . . . -175.7(6) no N2 C23 C24 C19 . . . . 176.9(6) no C1 O3 C18 C19 . . . . -178.2(6) no C1 C2 C3 C4 . . . . -3(1) no C1 C11 C4 C3 . . . . -40.6(8) no C1 C11 C4 C5 . . . . 82.8(8) no C1 C11 C4 C9 . . . . -161.9(6) no C1 C11 C10 C7 . . . . -128.6(7) no C1 C11 C10 C16 . . . . 108.9(8) no C1 C11 C10 C17 . . . . -8.4(9) no C2 C1 O3 C18 . . . . -87.3(8) no C2 C1 C11 C4 . . . . 39.8(8) no C2 C1 C11 C10 . . . . 164.8(7) no C2 C3 C4 C5 . . . . -91.3(8) no C2 C3 C4 C9 . . . . 140.3(7) no C2 C3 C4 C11 . . . . 26.5(9) no C3 C2 C1 C11 . . . . -24(1) no C3 C4 C5 C6 . . . . 171.8(7) no C3 C4 C9 C8 . . . . -172.2(7) no C3 C4 C11 C10 . . . . -171.5(7) no C4 C5 C6 C7 . . . . -1(1) no C4 C9 O2 C12 . . . . 139.6(7) no C4 C9 C8 C7 . . . . -3.0(9) no C4 C11 C10 C7 . . . . -8.5(9) no C4 C11 C10 C16 . . . . -131.0(7) no C4 C11 C10 C17 . . . . 111.7(7) no C5 C4 C9 C8 . . . . 55.6(7) no C5 C4 C11 C10 . . . . -48.1(9) no C5 C6 C7 C8 . . . . 54(1) no C5 C6 C7 C10 . . . . -59.1(9) no C5 C6 C7 C15 . . . . 177.7(8) no C6 C5 C4 C9 . . . . -56.3(9) no C6 C5 C4 C11 . . . . 56.8(9) no C6 C7 C8 C9 . . . . -49.1(9) no C6 C7 C10 C11 . . . . 59.3(8) no C6 C7 C10 C16 . . . . 179.1(6) no C6 C7 C10 C17 . . . . -61.0(8) no C7 C8 O1 C12 . . . . -138.9(7) no C8 O1 C12 C13 . . . . -86.9(8) no C8 O1 C12 C14 . . . . 149.1(8) no C8 C7 C10 C11 . . . . -53.3(8) no C8 C7 C10 C16 . . . . 66.5(8) no C8 C7 C10 C17 . . . . -173.6(6) no C8 C9 O2 C12 . . . . 22.0(8) no C8 C9 C4 C11 . . . . -59.5(8) no C9 O2 C12 C13 . . . . 83.9(8) no C9 O2 C12 C14 . . . . -150.0(7) no C9 C4 C11 C10 . . . . 67.1(8) no C9 C8 O1 C12 . . . . -16.8(9) no C9 C8 C7 C10 . . . . 62.5(8) no C9 C8 C7 C15 . . . . -172.5(7) no C11 C1 O3 C18 . . . . 155.1(6) no C11 C10 C7 C15 . . . . -177.9(8) no C15 C7 C10 C16 . . . . -58(1) no C15 C7 C10 C17 . . . . 62(1) no C18 C19 C20 C21 . . . . 176.4(7) no C18 C19 C24 C23 . . . . -177.2(6) no C19 C20 C21 C22 . . . . 2(1) no C19 C24 C23 C22 . . . . -1(1) no C20 C19 C24 C23 . . . . -0(1) no C20 C21 C22 C23 . . . . -2(1) no C21 C20 C19 C24 . . . . -0(1) no C21 C22 C23 C24 . . . . 2(1) no #------------------------------------------------------------------------------ #===END data_ban0818 _database_code_depnum_ccdc_archive 'CCDC 750107' _audit_creation_date 08-08-01 _audit_creation_method CRYSTALS_ver_12.85 _audit_update_record ; 2008-08-01 - Report on C14 H20 O3 by Anthony C. Willis for Jon Elsworth and Martin Banwell 2008-08-04 - passes checkcif tests with minor warnings ; _oxford_structure_analysis_title '8011529 ban0818' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.3638(1) _cell_length_b 12.4427(3) _cell_length_c 15.6175(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1236.64(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 = C14 H20 O3 # Dc = 1.27 Fooo = 512.00 Mu = 0.88 M = 236.31 # Found Formula = C14 H20 O3 # Dc = 1.27 FOOO = 512.00 Mu = 0.88 M = 236.31 _chemical_formula_sum 'C14 H20 O3' _chemical_formula_moiety 'C14 H20 O3' _chemical_compound_source local _chemical_formula_weight 236.31 _cell_measurement_reflns_used 14685 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 30 _cell_measurement_temperature 200 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.16 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.26 _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.088 # 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 0.140 -1 0 0 0.120 0 -1 1 0.080 0 1 -1 0.080 0 1 1 0.100 0 -1 -1 0.100 -8 16 -16 0.080 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.035 # 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 'Nonius KappaCCD' _diffrn_measurement_device_type Area _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 90 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, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _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 22478 _reflns_number_total 2075 _diffrn_reflns_av_R_equivalents 0.044 # Number of reflections with Friedels Law is 2075 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1809 _diffrn_reflns_theta_min 2.608 _diffrn_reflns_theta_max 30.033 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.033 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _oxford_diffrn_Wilson_B_factor 2.66 _oxford_diffrn_Wilson_scale 1.07 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.18 _refine_diff_density_max 0.20 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 2074 _refine_ls_number_restraints 0 _refine_ls_number_parameters 214 _oxford_refine_ls_R_factor_ref 0.0432 _refine_ls_wR_factor_ref 0.0701 _refine_ls_goodness_of_fit_ref 0.8107 _refine_ls_shift/su_max 0.004325 # The values computed from all data _oxford_reflns_number_all 2074 _refine_ls_R_factor_all 0.0432 _refine_ls_wR_factor_all 0.0701 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1595 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_gt 0.0680 # 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 syn _refine_ls_abs_structure_details ; The enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure. ; _refine_ls_structure_factor_coef Fsqd _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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~14~H~20~O~3~ is reported. ; _publ_section_comment #Text of the paper ; The compound is enantiometrically pure but the anomolous dispersion terms are very low for all elements in the structure and so the absolute configuration can not be determined in this experiment. Consequently Friedel-pair reflections have been averaged and the Flack parameter has not been refined. The absolute configuration of the molecule has been assigned on the basis of the synthetic precursors. The crystallographic asymmetric unit consists of one molecule of C~14~H~20~O~3~. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined without restraints and the displacement parameters were held fixed. The final difference electron density map is essentially featureless, with the largest peaks being located between carbon atoms. ; _publ_section_exptl_prep ; The compound was prepared by JDE and recrystallized from ethylacetate. The sample ID is JE1-90. ; #**************************************************************************** # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O 0.3610(2) 0.12745(10) 0.23650(8) 0.0449 1.0000 Uani . . . . . . . O2 O 0.18683(19) 0.43970(8) 0.45163(7) 0.0373 1.0000 Uani . . . . . . . O3 O 0.26696(16) 0.55169(8) 0.34227(6) 0.0332 1.0000 Uani . . . . . . . C1 C 0.4078(2) 0.17208(12) 0.31873(11) 0.0354 1.0000 Uani . . . . . . . C2 C 0.2706(3) 0.11815(13) 0.38724(12) 0.0409 1.0000 Uani . . . . . . . C3 C 0.1122(3) 0.20164(13) 0.41954(11) 0.0397 1.0000 Uani . . . . . . . C4 C 0.1171(2) 0.29100(11) 0.35235(10) 0.0299 1.0000 Uani . . . . . . . C5 C 0.0583(2) 0.40419(13) 0.38208(10) 0.0331 1.0000 Uani . . . . . . . C6 C 0.1020(2) 0.48490(12) 0.30894(10) 0.0326 1.0000 Uani . . . . . . . C7 C 0.1746(3) 0.42545(13) 0.22818(10) 0.0375 1.0000 Uani . . . . . . . C8 C 0.0075(3) 0.34238(14) 0.21150(12) 0.0434 1.0000 Uani . . . . . . . C9 C -0.0172(3) 0.27158(13) 0.27416(11) 0.0397 1.0000 Uani . . . . . . . C10 C 0.3812(3) 0.36362(13) 0.24510(10) 0.0351 1.0000 Uani . . . . . . . C11 C 0.3516(2) 0.29209(12) 0.32401(9) 0.0289 1.0000 Uani . . . . . . . C12 C 0.2552(3) 0.54608(12) 0.43378(9) 0.0349 1.0000 Uani . . . . . . . C13 C 0.4740(3) 0.56089(17) 0.46863(12) 0.0496 1.0000 Uani . . . . . . . C14 C 0.0986(4) 0.62753(16) 0.46777(14) 0.0558 1.0000 Uani . . . . . . . H1 H 0.475(4) 0.1107(17) 0.2127(13) 0.0670 1.0000 Uiso . . . . . . . H11 H 0.565(3) 0.1626(13) 0.3325(11) 0.0420 1.0000 Uiso . . . . . . . H21 H 0.355(3) 0.0887(16) 0.4347(12) 0.0508 1.0000 Uiso . . . . . . . H22 H 0.200(3) 0.0610(15) 0.3596(11) 0.0495 1.0000 Uiso . . . . . . . H31 H 0.167(3) 0.2308(14) 0.4762(11) 0.0477 1.0000 Uiso . . . . . . . H32 H -0.027(3) 0.1729(14) 0.4277(11) 0.0483 1.0000 Uiso . . . . . . . H51 H -0.089(3) 0.4063(14) 0.4011(10) 0.0397 1.0000 Uiso . . . . . . . H61 H -0.020(3) 0.5311(13) 0.2944(9) 0.0382 1.0000 Uiso . . . . . . . H71 H 0.192(2) 0.4770(13) 0.1794(11) 0.0431 1.0000 Uiso . . . . . . . H81 H -0.071(3) 0.3351(14) 0.1556(13) 0.0528 1.0000 Uiso . . . . . . . H91 H -0.115(3) 0.2122(15) 0.2719(11) 0.0477 1.0000 Uiso . . . . . . . H101 H 0.504(3) 0.4131(13) 0.2536(11) 0.0408 1.0000 Uiso . . . . . . . H102 H 0.417(3) 0.3170(13) 0.1934(11) 0.0418 1.0000 Uiso . . . . . . . H111 H 0.427(3) 0.3212(13) 0.3713(10) 0.0338 1.0000 Uiso . . . . . . . H131 H 0.519(4) 0.6347(19) 0.4540(15) 0.0732 1.0000 Uiso . . . . . . . H132 H 0.470(4) 0.5547(16) 0.5321(14) 0.0734 1.0000 Uiso . . . . . . . H133 H 0.570(4) 0.5018(18) 0.4436(14) 0.0725 1.0000 Uiso . . . . . . . H141 H 0.156(4) 0.700(2) 0.4569(15) 0.0816 1.0000 Uiso . . . . . . . H142 H 0.079(4) 0.6175(18) 0.5318(15) 0.0832 1.0000 Uiso . . . . . . . H143 H -0.048(4) 0.621(2) 0.4410(16) 0.0824 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 0.0428(6) 0.0431(6) 0.0488(7) -0.0163(6) 0.0057(6) 0.0034(6) O2 0.0531(7) 0.0297(5) 0.0290(5) 0.0017(5) 0.0043(5) -0.0019(5) O3 0.0410(5) 0.0310(5) 0.0276(5) 0.0022(5) -0.0010(5) -0.0057(5) C1 0.0287(7) 0.0334(8) 0.0439(9) -0.0043(7) -0.0006(7) 0.0023(6) C2 0.0469(9) 0.0322(8) 0.0437(9) 0.0043(8) -0.0006(8) 0.0031(8) C3 0.0408(8) 0.0330(8) 0.0454(9) 0.0065(7) 0.0102(8) -0.0032(8) C4 0.0258(6) 0.0272(7) 0.0366(7) 0.0016(6) 0.0051(6) -0.0010(6) C5 0.0305(7) 0.0325(7) 0.0362(8) -0.0001(7) 0.0065(7) 0.0007(6) C6 0.0318(7) 0.0277(7) 0.0382(8) 0.0012(6) -0.0055(6) 0.0000(6) C7 0.0477(9) 0.0350(8) 0.0298(7) 0.0032(7) -0.0055(7) -0.0030(8) C8 0.0474(10) 0.0391(9) 0.0435(10) -0.0049(8) -0.0137(8) -0.0007(8) C9 0.0294(7) 0.0346(8) 0.0551(10) -0.0061(8) -0.0042(8) -0.0028(7) C10 0.0380(8) 0.0341(8) 0.0332(8) -0.0039(7) 0.0075(7) -0.0041(7) C11 0.0257(6) 0.0292(7) 0.0318(7) -0.0026(6) 0.0015(6) -0.0022(6) C12 0.0484(8) 0.0290(7) 0.0273(7) -0.0008(6) 0.0030(7) 0.0010(8) C13 0.0637(11) 0.0455(10) 0.0397(9) -0.0026(9) -0.0124(9) -0.0071(10) C14 0.0749(14) 0.0386(9) 0.0540(12) -0.0056(9) 0.0132(11) 0.0098(11) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.045(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 . C1 . 1.431(2) yes O1 . H1 . 0.84(2) no O2 . C5 . 1.4297(19) yes O2 . C12 . 1.4209(18) yes O3 . C6 . 1.4367(18) yes O3 . C12 . 1.4328(16) yes C1 . C2 . 1.535(2) yes C1 . C11 . 1.538(2) yes C1 . H11 . 1.033(17) no C2 . C3 . 1.533(2) yes C2 . H21 . 0.986(19) no C2 . H22 . 0.944(19) no C3 . C4 . 1.529(2) yes C3 . H31 . 1.017(17) no C3 . H32 . 0.962(19) no C4 . C5 . 1.529(2) yes C4 . C9 . 1.510(2) yes C4 . C11 . 1.5568(18) yes C5 . C6 . 1.546(2) yes C5 . H51 . 0.987(17) no C6 . C7 . 1.533(2) yes C6 . H61 . 0.993(17) no C7 . C8 . 1.506(2) yes C7 . C10 . 1.547(2) yes C7 . H71 . 1.003(17) no C8 . C9 . 1.326(2) yes C8 . H81 . 1.01(2) no C9 . H91 . 0.965(19) no C10 . C11 . 1.532(2) yes C10 . H101 . 1.005(18) no C10 . H102 . 1.020(17) no C11 . H111 . 0.954(16) no C12 . C13 . 1.506(3) yes C12 . C14 . 1.517(2) yes C13 . H131 . 0.99(2) no C13 . H132 . 1.00(2) no C13 . H133 . 1.03(2) no C14 . H141 . 0.99(2) no C14 . H142 . 1.02(2) no C14 . H143 . 1.02(3) 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 . O1 . H1 . 108.1(14) no C5 . O2 . C12 . 108.30(11) yes C6 . O3 . C12 . 107.16(12) yes O1 . C1 . C2 . 109.72(13) yes O1 . C1 . C11 . 112.13(13) yes C2 . C1 . C11 . 104.75(12) yes O1 . C1 . H11 . 110.2(9) no C2 . C1 . H11 . 110.9(10) no C11 . C1 . H11 . 109.0(9) no C1 . C2 . C3 . 107.88(13) yes C1 . C2 . H21 . 112.2(10) no C3 . C2 . H21 . 111.2(11) no C1 . C2 . H22 . 106.2(11) no C3 . C2 . H22 . 110.5(10) no H21 . C2 . H22 . 108.7(15) no C2 . C3 . C4 . 104.70(13) yes C2 . C3 . H31 . 107.7(10) no C4 . C3 . H31 . 109.3(10) no C2 . C3 . H32 . 113.3(11) no C4 . C3 . H32 . 112.3(10) no H31 . C3 . H32 . 109.2(14) no C3 . C4 . C5 . 117.15(13) yes C3 . C4 . C9 . 115.29(13) yes C5 . C4 . C9 . 104.75(12) yes C3 . C4 . C11 . 102.75(12) yes C5 . C4 . C11 . 108.22(12) yes C9 . C4 . C11 . 108.31(12) yes C4 . C5 . O2 . 112.05(12) yes C4 . C5 . C6 . 109.26(12) yes O2 . C5 . C6 . 104.94(11) yes C4 . C5 . H51 . 110.4(11) no O2 . C5 . H51 . 107.9(10) no C6 . C5 . H51 . 112.1(10) no C5 . C6 . O3 . 103.85(11) yes C5 . C6 . C7 . 110.40(12) yes O3 . C6 . C7 . 110.91(12) yes C5 . C6 . H61 . 113.8(9) no O3 . C6 . H61 . 108.7(9) no C7 . C6 . H61 . 109.1(9) no C6 . C7 . C8 . 105.11(14) yes C6 . C7 . C10 . 110.83(13) yes C8 . C7 . C10 . 106.78(13) yes C6 . C7 . H71 . 110.5(9) no C8 . C7 . H71 . 112.8(9) no C10 . C7 . H71 . 110.7(9) no C7 . C8 . C9 . 114.34(15) yes C7 . C8 . H81 . 124.2(10) no C9 . C8 . H81 . 121.2(10) no C4 . C9 . C8 . 115.05(14) yes C4 . C9 . H91 . 121.1(10) no C8 . C9 . H91 . 123.9(10) no C7 . C10 . C11 . 108.77(13) yes C7 . C10 . H101 . 112.3(9) no C11 . C10 . H101 . 110.3(10) no C7 . C10 . H102 . 109.8(10) no C11 . C10 . H102 . 109.5(9) no H101 . C10 . H102 . 106.1(14) no C1 . C11 . C10 . 119.49(13) yes C1 . C11 . C4 . 103.29(12) yes C10 . C11 . C4 . 110.60(12) yes C1 . C11 . H111 . 107.1(10) no C10 . C11 . H111 . 109.9(9) no C4 . C11 . H111 . 105.5(10) no O3 . C12 . O2 . 104.90(11) yes O3 . C12 . C13 . 107.83(14) yes O2 . C12 . C13 . 109.04(14) yes O3 . C12 . C14 . 110.52(14) yes O2 . C12 . C14 . 110.63(14) yes C13 . C12 . C14 . 113.52(16) yes C12 . C13 . H131 . 107.3(14) no C12 . C13 . H132 . 109.1(14) no H131 . C13 . H132 . 108.0(18) no C12 . C13 . H133 . 108.7(12) no H131 . C13 . H133 . 113.8(18) no H132 . C13 . H133 . 109.7(18) no C12 . C14 . H141 . 108.0(14) no C12 . C14 . H142 . 109.9(13) no H141 . C14 . H142 . 109.0(19) no C12 . C14 . H143 . 113.4(14) no H141 . C14 . H143 . 110(2) no H142 . C14 . H143 . 106(2) 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 O3 2.830(2) . 3_645 no O1 C13 3.471(2) . 3_645 no O1 C6 3.512(2) . 3_545 no O3 C1 3.585(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 O1 C1 C2 C3 . . . . -110.8(1) no O1 C1 C11 C4 . . . . 87.8(1) no O1 C1 C11 C10 . . . . -35.5(2) no O2 C5 C4 C3 . . . . 56.4(2) no O2 C5 C4 C9 . . . . -174.4(1) no O2 C5 C4 C11 . . . . -59.1(2) no O2 C5 C6 O3 . . . . 5.5(1) no O2 C5 C6 C7 . . . . 124.4(1) no O2 C12 O3 C6 . . . . 33.8(2) no O3 C6 C5 C4 . . . . -114.8(1) no O3 C6 C7 C8 . . . . 168.2(1) no O3 C6 C7 C10 . . . . 53.2(2) no O3 C12 O2 C5 . . . . -30.1(2) no C1 C2 C3 C4 . . . . 15.9(2) no C1 C11 C4 C3 . . . . 41.1(1) no C1 C11 C4 C5 . . . . 165.6(1) no C1 C11 C4 C9 . . . . -81.3(1) no C1 C11 C10 C7 . . . . 128.5(1) no C2 C1 C11 C4 . . . . -31.1(1) no C2 C1 C11 C10 . . . . -154.4(1) no C2 C3 C4 C5 . . . . -153.3(1) no C2 C3 C4 C9 . . . . 82.7(2) no C2 C3 C4 C11 . . . . -34.9(2) no C3 C2 C1 C11 . . . . 9.8(2) no C3 C4 C5 C6 . . . . 172.3(1) no C3 C4 C9 C8 . . . . -171.9(2) no C3 C4 C11 C10 . . . . 170.1(1) no C4 C5 O2 C12 . . . . 133.5(1) no C4 C5 C6 C7 . . . . 4.1(2) no C4 C9 C8 C7 . . . . 3.4(2) no C4 C11 C10 C7 . . . . 8.9(2) no C5 O2 C12 C13 . . . . -145.4(1) no C5 O2 C12 C14 . . . . 89.1(2) no C5 C4 C9 C8 . . . . 57.8(2) no C5 C4 C11 C10 . . . . -65.4(2) no C5 C6 O3 C12 . . . . -23.8(1) no C5 C6 C7 C8 . . . . 53.7(2) no C5 C6 C7 C10 . . . . -61.3(2) no C6 O3 C12 C13 . . . . 149.9(1) no C6 O3 C12 C14 . . . . -85.5(2) no C6 C5 O2 C12 . . . . 15.0(1) no C6 C5 C4 C9 . . . . -58.6(1) no C6 C5 C4 C11 . . . . 56.8(1) no C6 C7 C8 C9 . . . . -60.8(2) no C6 C7 C10 C11 . . . . 53.0(2) no C7 C6 O3 C12 . . . . -142.4(1) no C8 C7 C10 C11 . . . . -61.0(2) no C8 C9 C4 C11 . . . . -57.5(2) no C9 C4 C11 C10 . . . . 47.7(2) no C9 C8 C7 C10 . . . . 57.0(2) no #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O1 . H1 . O3 3_645 173(2) 0.84(2) 1.99(2) 2.830(2) no #===END