# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_i146 _database_code_depnum_ccdc_archive 'CCDC 773208' #TrackingRef '- 773208.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H30 O' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C28 H30 O' _chemical_formula_iupac ? _chemical_formula_weight 382.52 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_space_group_name_H-M 'P b c n' _symmetry_Int_Tables_number 60 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,y,1/2-z 5 -x,-y,-z 6 1/2+x,1/2+y,1/2-z 7 1/2-x,1/2+y,z 8 x,-y,1/2+z _cell_length_a 7.6851(3) _cell_length_b 16.8705(5) _cell_length_c 16.3611(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2121.24(12) _cell_formula_units_Z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 3799 _cell_measurement_theta_min 3.7519 _cell_measurement_theta_max 64.9278 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour 'translucent, colourless' _exptl_crystal_size_max 0.270 _exptl_crystal_size_mid 0.190 _exptl_crystal_size_min 0.050 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.536 _exptl_crystal_density_meas_temp ? # Permitted for # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.88389 _exptl_absorpt_correction_T_max 1.00000 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 123 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Ruby (Gemini ultra Mo)' _diffrn_measurement_method '\w scans' _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -13.00 76.60 1.4000 3.0000 omega____ theta____ kappa____ phi______ frames - 8.2112 38.0000 150.0000 64 #__ type_ start__ end____ width___ exp.time_ 2 omega -23.00 37.20 1.4000 3.0000 omega____ theta____ kappa____ phi______ frames - 8.2112 -77.0000 120.0000 43 #__ type_ start__ end____ width___ exp.time_ 3 omega -129.00 -101.00 1.4000 80.0000 omega____ theta____ kappa____ phi______ frames - -88.8475 -114.0000 25.0000 20 #__ type_ start__ end____ width___ exp.time_ 4 omega -116.00 -60.00 1.4000 80.0000 omega____ theta____ kappa____ phi______ frames - -88.8475 125.0000 -180.0000 40 #__ type_ start__ end____ width___ exp.time_ 5 omega -64.00 -17.80 1.4000 80.0000 omega____ theta____ kappa____ phi______ frames - -88.8475 45.0000 30.0000 33 #__ type_ start__ end____ width___ exp.time_ 6 omega -141.00 -89.20 1.4000 80.0000 omega____ theta____ kappa____ phi______ frames - -88.8475 167.0000 -9.0000 37 #__ type_ start__ end____ width___ exp.time_ 7 omega 17.00 73.00 1.4000 80.0000 omega____ theta____ kappa____ phi______ frames - 90.0975 -45.0000 150.0000 40 #__ type_ start__ end____ width___ exp.time_ 8 omega 23.00 76.20 1.4000 80.0000 omega____ theta____ kappa____ phi______ frames - 90.0975 -45.0000 90.0000 38 #__ type_ start__ end____ width___ exp.time_ 9 omega 18.00 54.40 1.4000 80.0000 omega____ theta____ kappa____ phi______ frames - 90.0975 -45.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 10 omega 36.00 114.40 1.4000 80.0000 omega____ theta____ kappa____ phi______ frames - 90.0975 -167.0000 9.0000 56 ; _diffrn_detector_area_resol_mean 10.5431 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 6017 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 5.24 _diffrn_reflns_theta_max 65.05 _diffrn_reflns_theta_full 65.05 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measured_fraction_theta_full 0.982 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1772 # number of observed reflections (> n sig(I)) _reflns_number_gt 1511 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) ; _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0753P)^2^+0.6737P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 1772 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1282 _refine_ls_wR_factor_gt 0.1234 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.263 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.044 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.50000 0.06359(9) 0.75000 1.000 0.0298(5) . . C1 C Uani 0.27516(19) 0.16155(10) 0.71876(9) 1.000 0.0283(4) . . C2 C Uani 0.2497(2) 0.24222(10) 0.72698(9) 1.000 0.0288(4) . . C3 C Uani 0.17762(19) 0.28537(9) 0.65941(10) 1.000 0.0289(5) . . C4 C Uani 0.1561(2) 0.36867(10) 0.66161(10) 1.000 0.0339(5) . . C5 C Uani 0.0910(2) 0.40992(10) 0.59625(11) 1.000 0.0370(5) . . C6 C Uani 0.0401(2) 0.36979(10) 0.52534(11) 1.000 0.0366(5) . . C7 C Uani 0.0558(2) 0.28924(10) 0.52096(10) 1.000 0.0328(5) . . C8 C Uani 0.12607(18) 0.24499(10) 0.58669(10) 1.000 0.0283(5) . . C9 C Uani 0.14581(19) 0.16070(10) 0.58201(9) 1.000 0.0291(5) . . C10 C Uani 0.22058(19) 0.12265(9) 0.64676(10) 1.000 0.0294(5) . . C11 C Uani 0.36025(19) 0.11012(10) 0.78395(10) 1.000 0.0302(5) . . C12 C Uani 0.2331(2) 0.05150(11) 0.82115(11) 1.000 0.0376(5) . . C13 C Uani 0.2932(2) 0.28585(10) 0.80509(11) 1.000 0.0369(5) . . C14 C Uani 0.0859(2) 0.11552(10) 0.50795(10) 1.000 0.0359(5) . . H4 H Uiso 0.18770 0.39670 0.70970 1.000 0.0410 calc R H5 H Uiso 0.08040 0.46600 0.59910 1.000 0.0440 calc R H6 H Uiso -0.00550 0.39860 0.48020 1.000 0.0440 calc R H7 H Uiso 0.01900 0.26240 0.47290 1.000 0.0390 calc R H10 H Uiso 0.23680 0.06690 0.64320 1.000 0.0350 calc R H11 H Uiso 0.40760 0.14500 0.82810 1.000 0.0360 calc R H12A H Uiso 0.18750 0.01670 0.77820 1.000 0.0450 calc R H12B H Uiso 0.13680 0.08040 0.84670 1.000 0.0450 calc R H12C H Uiso 0.29300 0.01960 0.86250 1.000 0.0450 calc R H13A H Uiso 0.30710 0.24760 0.84970 1.000 0.0440 calc R H13B H Uiso 0.40180 0.31540 0.79780 1.000 0.0440 calc R H13C H Uiso 0.19890 0.32280 0.81840 1.000 0.0440 calc R H14A H Uiso 0.14780 0.13490 0.45950 1.000 0.0430 calc R H14B H Uiso -0.03950 0.12320 0.50060 1.000 0.0430 calc R H14C H Uiso 0.11030 0.05900 0.51550 1.000 0.0430 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0202(7) 0.0297(8) 0.0395(9) 0.0000 0.0033(6) 0.0000 C1 0.0197(7) 0.0332(8) 0.0320(8) -0.0016(6) 0.0027(6) 0.0002(6) C2 0.0191(7) 0.0342(8) 0.0332(8) -0.0045(6) -0.0003(6) 0.0012(6) C3 0.0193(7) 0.0326(8) 0.0348(9) -0.0041(6) 0.0016(6) 0.0000(6) C4 0.0275(8) 0.0327(9) 0.0414(9) -0.0067(7) -0.0023(7) 0.0009(6) C5 0.0294(8) 0.0308(9) 0.0508(10) 0.0002(7) -0.0011(7) 0.0017(7) C6 0.0284(9) 0.0399(9) 0.0416(9) 0.0067(7) -0.0016(7) 0.0027(7) C7 0.0250(8) 0.0406(9) 0.0327(9) -0.0009(7) -0.0005(6) -0.0015(7) C8 0.0182(7) 0.0335(9) 0.0332(8) -0.0018(6) 0.0027(6) -0.0007(6) C9 0.0220(7) 0.0331(9) 0.0323(8) -0.0031(7) 0.0028(6) -0.0037(6) C10 0.0241(8) 0.0280(8) 0.0360(9) -0.0025(6) 0.0044(6) -0.0014(6) C11 0.0231(8) 0.0341(9) 0.0333(8) -0.0023(6) 0.0021(6) 0.0038(6) C12 0.0265(8) 0.0453(10) 0.0411(10) 0.0076(7) 0.0050(7) 0.0025(7) C13 0.0356(9) 0.0371(9) 0.0380(9) -0.0089(7) -0.0063(7) 0.0061(7) C14 0.0380(9) 0.0361(9) 0.0337(9) -0.0041(7) -0.0002(7) -0.0045(7) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.4416(18) . . yes O1 C11 1.4416(18) . 4_656 yes C1 C2 1.382(2) . . no C1 C10 1.412(2) . . no C1 C11 1.523(2) . . no C2 C3 1.435(2) . . no C2 C13 1.512(2) . . no C3 C4 1.416(2) . . no C3 C8 1.427(2) . . no C4 C5 1.370(2) . . no C5 C6 1.399(2) . . no C6 C7 1.366(2) . . no C7 C8 1.416(2) . . no C8 C9 1.432(2) . . no C9 C10 1.366(2) . . no C9 C14 1.504(2) . . no C11 C12 1.518(2) . . no C4 H4 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C10 H10 0.9500 . . no C11 H11 1.0000 . . no C12 H12A 0.9800 . . no C12 H12B 0.9800 . . no C12 H12C 0.9800 . . no C13 H13A 0.9800 . . no C13 H13B 0.9800 . . no C13 H13C 0.9800 . . no C14 H14A 0.9800 . . no C14 H14B 0.9800 . . no C14 H14C 0.9800 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 C11 114.02(14) . . 4_656 yes C2 C1 C10 119.80(14) . . . no C2 C1 C11 123.64(14) . . . no C10 C1 C11 116.56(14) . . . no C1 C2 C3 118.65(14) . . . no C1 C2 C13 122.04(14) . . . no C3 C2 C13 119.31(14) . . . no C2 C3 C4 121.95(15) . . . no C2 C3 C8 120.49(14) . . . no C4 C3 C8 117.56(14) . . . no C3 C4 C5 121.80(15) . . . no C4 C5 C6 120.23(16) . . . no C5 C6 C7 120.01(16) . . . no C6 C7 C8 121.21(15) . . . no C3 C8 C7 119.17(15) . . . no C3 C8 C9 119.29(14) . . . no C7 C8 C9 121.55(15) . . . no C8 C9 C10 118.03(14) . . . no C8 C9 C14 120.93(14) . . . no C10 C9 C14 121.05(15) . . . no C1 C10 C9 123.62(15) . . . no O1 C11 C1 111.12(12) . . . yes O1 C11 C12 106.22(13) . . . yes C1 C11 C12 112.07(13) . . . no C3 C4 H4 119.00 . . . no C5 C4 H4 119.00 . . . no C4 C5 H5 120.00 . . . no C6 C5 H5 120.00 . . . no C5 C6 H6 120.00 . . . no C7 C6 H6 120.00 . . . no C6 C7 H7 119.00 . . . no C8 C7 H7 119.00 . . . no C1 C10 H10 118.00 . . . no C9 C10 H10 118.00 . . . no O1 C11 H11 109.00 . . . no C1 C11 H11 109.00 . . . no C12 C11 H11 109.00 . . . no C11 C12 H12A 109.00 . . . no C11 C12 H12B 109.00 . . . no C11 C12 H12C 109.00 . . . no H12A C12 H12B 109.00 . . . no H12A C12 H12C 110.00 . . . no H12B C12 H12C 109.00 . . . no C2 C13 H13A 109.00 . . . no C2 C13 H13B 109.00 . . . no C2 C13 H13C 109.00 . . . no H13A C13 H13B 109.00 . . . no H13A C13 H13C 109.00 . . . no H13B C13 H13C 109.00 . . . no C9 C14 H14A 110.00 . . . no C9 C14 H14B 109.00 . . . no C9 C14 H14C 109.00 . . . no H14A C14 H14B 110.00 . . . no H14A C14 H14C 109.00 . . . no H14B C14 H14C 109.00 . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 O1 C11 C1 61.47(14) 4_656 . . . no C11 O1 C11 C12 -176.39(11) 4_656 . . . no C11 C1 C2 C3 176.27(14) . . . . no C11 C1 C2 C13 -4.5(2) . . . . no C2 C1 C10 C9 1.6(2) . . . . no C11 C1 C10 C9 -178.48(14) . . . . no C2 C1 C11 O1 -128.16(15) . . . . no C2 C1 C11 C12 113.17(17) . . . . no C10 C1 C11 O1 51.95(18) . . . . no C10 C1 C11 C12 -66.73(18) . . . . no C10 C1 C2 C13 175.35(14) . . . . no C10 C1 C2 C3 -3.8(2) . . . . no C1 C2 C3 C8 2.8(2) . . . . no C13 C2 C3 C4 4.1(2) . . . . no C1 C2 C3 C4 -176.66(14) . . . . no C13 C2 C3 C8 -176.38(14) . . . . no C8 C3 C4 C5 -1.1(2) . . . . no C2 C3 C4 C5 178.45(15) . . . . no C4 C3 C8 C7 -0.3(2) . . . . no C4 C3 C8 C9 179.97(14) . . . . no C2 C3 C8 C7 -179.83(14) . . . . no C2 C3 C8 C9 0.5(2) . . . . no C3 C4 C5 C6 1.4(2) . . . . no C4 C5 C6 C7 -0.2(2) . . . . no C5 C6 C7 C8 -1.2(2) . . . . no C6 C7 C8 C3 1.4(2) . . . . no C6 C7 C8 C9 -178.88(14) . . . . no C3 C8 C9 C14 177.31(13) . . . . no C7 C8 C9 C10 177.61(14) . . . . no C3 C8 C9 C10 -2.7(2) . . . . no C7 C8 C9 C14 -2.4(2) . . . . no C14 C9 C10 C1 -178.27(14) . . . . no C8 C9 C10 C1 1.7(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 H10 2.6700 . . no O1 H10 2.6700 . 4_656 no C6 C14 3.542(2) . 3_456 no C6 C9 3.540(2) . 3_456 no C9 C6 3.540(2) . 3_556 no C10 C11 3.422(2) . 4_656 no C11 C10 3.422(2) . 4_656 no C14 C6 3.542(2) . 3_556 no C1 H11 2.5700 . 4_656 no C2 H13B 2.9800 . 4_656 no C3 H13C 2.9800 . 4_556 no C4 H13C 2.8500 . 4_556 no C4 H13C 2.7000 . . no C4 H13B 3.0600 . . no C5 H10 3.0600 . 7_555 no C5 H12C 3.0200 . 6_456 no C5 H13C 3.0100 . 4_556 no C6 H14A 3.0300 . 3_456 no C7 H14A 2.8800 . . no C7 H13A 3.0600 . 2_554 no C7 H14B 2.9100 . . no C9 H12B 2.8100 . 4_556 no C9 H6 3.0400 . 3_556 no C10 H12A 2.8100 . . no C10 H6 2.9800 . 3_556 no C10 H11 2.9100 . 4_656 no C10 H12B 2.8400 . 4_556 no C11 H13A 2.5900 . . no C12 H10 2.9200 . . no C13 H4 2.5700 . . no C13 H11 2.5600 . . no C13 H13B 2.9300 . 4_656 no C13 H14A 2.8900 . 2_555 no C14 H7 2.5900 . . no C14 H12B 2.9900 . 4_556 no H4 C13 2.5700 . . no H4 H13B 2.5800 . . no H4 H13C 2.1700 . . no H4 H12A 2.5000 . 7_555 no H5 H12C 2.4700 . 6_456 no H5 H10 2.3200 . 7_555 no H6 C9 3.0400 . 3_456 no H6 C10 2.9800 . 3_456 no H7 C14 2.5900 . . no H7 H14A 2.3800 . . no H7 H14B 2.4300 . . no H7 H13A 2.4200 . 2_554 no H10 O1 2.6700 . . no H10 C12 2.9200 . . no H10 H12A 2.4000 . . no H10 H14C 2.3100 . . no H10 C5 3.0600 . 7_545 no H10 H5 2.3200 . 7_545 no H11 C13 2.5600 . . no H11 H13A 1.9300 . . no H11 C1 2.5700 . 4_656 no H11 C10 2.9100 . 4_656 no H12A C10 2.8100 . . no H12A H10 2.4000 . . no H12A H4 2.5000 . 7_545 no H12B C9 2.8100 . 4_556 no H12B C10 2.8400 . 4_556 no H12B C14 2.9900 . 4_556 no H12C C5 3.0200 . 6_546 no H12C H5 2.4700 . 6_546 no H13A C11 2.5900 . . no H13A H11 1.9300 . . no H13A C7 3.0600 . 2_555 no H13A H7 2.4200 . 2_555 no H13B C4 3.0600 . . no H13B H4 2.5800 . . no H13B C2 2.9800 . 4_656 no H13B C13 2.9300 . 4_656 no H13B H13B 2.1700 . 4_656 no H13C C4 2.7000 . . no H13C H4 2.1700 . . no H13C C3 2.9800 . 4_556 no H13C C4 2.8500 . 4_556 no H13C C5 3.0100 . 4_556 no H14A C7 2.8800 . . no H14A H7 2.3800 . . no H14A C13 2.8900 . 2_554 no H14A C6 3.0300 . 3_556 no H14B C7 2.9100 . . no H14B H7 2.4300 . . no H14C H10 2.3100 . . no data_i191 _database_code_depnum_ccdc_archive 'CCDC 773209' #TrackingRef '- 773209.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H16 O' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C14 H16 O' _chemical_formula_iupac ? _chemical_formula_weight 200.27 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 8.1442(3) _cell_length_b 4.8533(2) _cell_length_c 27.8100(11) _cell_angle_alpha 90 _cell_angle_beta 94.010(4) _cell_angle_gamma 90 _cell_volume 1096.53(7) _cell_formula_units_Z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 2699 _cell_measurement_theta_min 3.1919 _cell_measurement_theta_max 66.2056 _cell_special_details ; ; _exptl_crystal_description 'elongated plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.042 _exptl_crystal_size_min 0.008 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.574 _exptl_crystal_density_meas_temp ? # Permitted for # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_T_min 0.84432 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 123 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Goniometer Xcalibur, detector: Ruby (Gemini ultra Mo)' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5431 # number of measured reflections (redundant set) _diffrn_reflns_number 4568 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 66.33 _diffrn_reflns_theta_full 66.33 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measured_fraction_theta_full 0.987 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1897 # number of observed reflections (> n sig(I)) _reflns_number_gt 1574 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) ; _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0787P)^2^+0.0414P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 1897 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.171 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.041 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.29011(12) -0.32532(19) 0.73059(3) 1.000 0.0311(3) . . C1 C Uani 0.27036(16) -0.3203(3) 0.67899(5) 1.000 0.0280(4) . . C2 C Uani 0.11159(16) -0.1752(3) 0.66207(5) 1.000 0.0366(4) . . C3 C Uani 0.41773(15) -0.1906(2) 0.65671(4) 1.000 0.0242(3) . . C4 C Uani 0.51095(15) 0.0094(2) 0.68392(4) 1.000 0.0246(3) . . C5 C Uani 0.64233(15) 0.1457(3) 0.66677(4) 1.000 0.0252(3) . . C6 C Uani 0.68628(15) 0.0848(3) 0.61898(4) 1.000 0.0268(4) . . C7 C Uani 0.81622(16) 0.2244(3) 0.59786(5) 1.000 0.0329(4) . . C8 C Uani 0.85524(18) 0.1687(3) 0.55172(5) 1.000 0.0405(5) . . C9 C Uani 0.76642(18) -0.0314(3) 0.52449(5) 1.000 0.0402(5) . . C10 C Uani 0.64013(17) -0.1698(3) 0.54353(5) 1.000 0.0340(4) . . C11 C Uani 0.59383(16) -0.1168(3) 0.59106(4) 1.000 0.0274(4) . . C12 C Uani 0.45807(15) -0.2558(3) 0.61067(4) 1.000 0.0261(4) . . C13 C Uani 0.73723(16) 0.3526(3) 0.69778(5) 1.000 0.0312(4) . . C14 C Uani 0.36271(17) -0.4677(3) 0.58005(5) 1.000 0.0332(4) . . H1 H Uiso 0.26170 -0.51550 0.66760 1.000 0.0340 calc R H1O H Uiso 0.264(2) -0.161(5) 0.7420(7) 1.000 0.053(5) . . H2A H Uiso 0.01900 -0.26240 0.67690 1.000 0.0550 calc R H2B H Uiso 0.09500 -0.18880 0.62690 1.000 0.0550 calc R H2C H Uiso 0.11830 0.01920 0.67150 1.000 0.0550 calc R H4 H Uiso 0.48100 0.05100 0.71550 1.000 0.0300 calc R H7 H Uiso 0.87760 0.35950 0.61610 1.000 0.0390 calc R H8 H Uiso 0.94230 0.26570 0.53820 1.000 0.0490 calc R H9 H Uiso 0.79420 -0.07100 0.49260 1.000 0.0480 calc R H10 H Uiso 0.58160 -0.30510 0.52450 1.000 0.0410 calc R H13A H Uiso 0.68480 0.37550 0.72820 1.000 0.0470 calc R H13B H Uiso 0.73840 0.52980 0.68090 1.000 0.0470 calc R H13C H Uiso 0.85040 0.28760 0.70450 1.000 0.0470 calc R H14A H Uiso 0.28320 -0.56010 0.59950 1.000 0.0500 calc R H14B H Uiso 0.43910 -0.60420 0.56830 1.000 0.0500 calc R H14C H Uiso 0.30410 -0.37610 0.55250 1.000 0.0500 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0411(5) 0.0236(5) 0.0300(5) 0.0017(4) 0.0118(4) 0.0005(4) C1 0.0336(7) 0.0206(6) 0.0303(7) -0.0012(5) 0.0054(5) -0.0031(5) C2 0.0277(7) 0.0355(8) 0.0468(8) 0.0016(6) 0.0043(6) -0.0046(6) C3 0.0273(6) 0.0186(6) 0.0268(6) 0.0018(5) 0.0022(5) 0.0039(5) C4 0.0288(6) 0.0207(6) 0.0246(6) 0.0005(5) 0.0038(5) 0.0047(5) C5 0.0248(6) 0.0214(6) 0.0293(6) 0.0021(5) 0.0017(5) 0.0042(5) C6 0.0261(6) 0.0239(6) 0.0307(7) 0.0052(5) 0.0041(5) 0.0073(5) C7 0.0269(7) 0.0330(7) 0.0392(7) 0.0071(6) 0.0056(5) 0.0045(6) C8 0.0337(7) 0.0453(9) 0.0443(8) 0.0137(7) 0.0162(6) 0.0085(6) C9 0.0460(8) 0.0452(9) 0.0311(7) 0.0054(7) 0.0147(6) 0.0145(7) C10 0.0402(8) 0.0342(7) 0.0282(7) 0.0009(6) 0.0061(5) 0.0109(6) C11 0.0325(7) 0.0242(6) 0.0259(6) 0.0030(5) 0.0045(5) 0.0090(5) C12 0.0316(7) 0.0201(6) 0.0265(6) 0.0017(5) 0.0014(5) 0.0046(5) C13 0.0300(7) 0.0272(7) 0.0365(7) -0.0012(6) 0.0023(5) -0.0008(5) C14 0.0427(8) 0.0271(7) 0.0295(7) -0.0035(6) 0.0001(5) 0.0017(6) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.4330(16) . . yes O1 H1O 0.89(2) . . no C1 C3 1.5247(18) . . no C1 C2 1.5180(19) . . no C3 C12 1.3807(16) . . no C3 C4 1.4180(15) . . no C4 C5 1.3716(17) . . no C5 C13 1.5021(19) . . no C5 C6 1.4312(16) . . no C6 C7 1.4181(19) . . no C6 C11 1.4302(19) . . no C7 C8 1.370(2) . . no C8 C9 1.401(2) . . no C9 C10 1.366(2) . . no C10 C11 1.4231(18) . . no C11 C12 1.4350(18) . . no C12 C14 1.5144(19) . . no C1 H1 1.0000 . . no C2 H2A 0.9800 . . no C2 H2B 0.9800 . . no C2 H2C 0.9800 . . no C4 H4 0.9500 . . no C7 H7 0.9500 . . no C8 H8 0.9500 . . no C9 H9 0.9500 . . no C10 H10 0.9500 . . no C13 H13A 0.9800 . . no C13 H13B 0.9800 . . no C13 H13C 0.9800 . . no C14 H14A 0.9800 . . no C14 H14B 0.9800 . . no C14 H14C 0.9800 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1O 109.2(13) . . . no O1 C1 C2 110.60(11) . . . yes C2 C1 C3 111.11(11) . . . no O1 C1 C3 112.18(10) . . . yes C1 C3 C4 118.23(10) . . . no C1 C3 C12 121.83(11) . . . no C4 C3 C12 119.90(11) . . . no C3 C4 C5 123.10(11) . . . no C4 C5 C6 118.37(11) . . . no C6 C5 C13 121.28(11) . . . no C4 C5 C13 120.36(10) . . . no C5 C6 C11 119.28(11) . . . no C7 C6 C11 118.80(11) . . . no C5 C6 C7 121.89(12) . . . no C6 C7 C8 121.49(13) . . . no C7 C8 C9 119.87(13) . . . no C8 C9 C10 120.37(13) . . . no C9 C10 C11 121.79(13) . . . no C6 C11 C12 120.38(10) . . . no C10 C11 C12 121.95(12) . . . no C6 C11 C10 117.67(12) . . . no C3 C12 C14 122.08(11) . . . no C11 C12 C14 118.95(10) . . . no C3 C12 C11 118.97(11) . . . no O1 C1 H1 108.00 . . . no C2 C1 H1 108.00 . . . no C3 C1 H1 108.00 . . . no C1 C2 H2A 109.00 . . . no C1 C2 H2B 109.00 . . . no C1 C2 H2C 109.00 . . . no H2A C2 H2B 110.00 . . . no H2A C2 H2C 109.00 . . . no H2B C2 H2C 109.00 . . . no C3 C4 H4 118.00 . . . no C5 C4 H4 118.00 . . . no C6 C7 H7 119.00 . . . no C8 C7 H7 119.00 . . . no C7 C8 H8 120.00 . . . no C9 C8 H8 120.00 . . . no C8 C9 H9 120.00 . . . no C10 C9 H9 120.00 . . . no C9 C10 H10 119.00 . . . no C11 C10 H10 119.00 . . . no C5 C13 H13A 109.00 . . . no C5 C13 H13B 109.00 . . . no C5 C13 H13C 109.00 . . . no H13A C13 H13B 109.00 . . . no H13A C13 H13C 109.00 . . . no H13B C13 H13C 109.00 . . . no C12 C14 H14A 109.00 . . . no C12 C14 H14B 110.00 . . . no C12 C14 H14C 110.00 . . . no H14A C14 H14B 109.00 . . . no H14A C14 H14C 110.00 . . . no H14B C14 H14C 109.00 . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C3 C4 -28.09(15) . . . . no O1 C1 C3 C12 154.20(11) . . . . no C2 C1 C3 C4 96.30(13) . . . . no C2 C1 C3 C12 -81.42(15) . . . . no C1 C3 C4 C5 -177.74(11) . . . . no C12 C3 C4 C5 0.02(18) . . . . no C1 C3 C12 C11 177.16(12) . . . . no C1 C3 C12 C14 -2.33(19) . . . . no C4 C3 C12 C11 -0.51(18) . . . . no C4 C3 C12 C14 -180.00(12) . . . . no C3 C4 C5 C6 0.60(18) . . . . no C3 C4 C5 C13 -179.17(11) . . . . no C4 C5 C6 C7 177.44(12) . . . . no C4 C5 C6 C11 -0.71(19) . . . . no C13 C5 C6 C7 -2.8(2) . . . . no C13 C5 C6 C11 179.06(12) . . . . no C5 C6 C7 C8 -178.64(13) . . . . no C11 C6 C7 C8 -0.5(2) . . . . no C5 C6 C11 C10 179.38(12) . . . . no C5 C6 C11 C12 0.2(2) . . . . no C7 C6 C11 C10 1.17(19) . . . . no C7 C6 C11 C12 -177.98(13) . . . . no C6 C7 C8 C9 -0.4(2) . . . . no C7 C8 C9 C10 0.6(2) . . . . no C8 C9 C10 C11 0.2(2) . . . . no C9 C10 C11 C6 -1.1(2) . . . . no C9 C10 C11 C12 178.09(13) . . . . no C6 C11 C12 C3 0.38(19) . . . . no C6 C11 C12 C14 179.89(12) . . . . no C10 C11 C12 C3 -178.73(12) . . . . no C10 C11 C12 C14 0.8(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 O1 2.7531(13) . 2_546 no O1 O1 2.7531(13) . 2_556 no O1 H4 2.4500 . . no O1 H1O 1.87(2) . 2_546 no O1 H2C 2.8700 . 2_546 no O1 H4 2.8200 . 2_546 no C2 C14 3.472(2) . . no C2 C7 3.484(2) . 1_455 no C3 C13 3.5461(18) . 1_545 no C5 C12 3.5771(19) . 1_565 no C6 C14 3.5263(19) . 1_565 no C7 C10 3.561(2) . 1_565 no C7 C2 3.484(2) . 1_655 no C10 C7 3.561(2) . 1_545 no C12 C5 3.5771(19) . 1_545 no C13 C3 3.5461(18) . 1_565 no C14 C6 3.5263(19) . 1_545 no C14 C2 3.472(2) . . no C1 H1O 2.78(2) . 2_546 no C1 H14A 2.5100 . . no C2 H14A 2.9700 . . no C3 H13B 2.9800 . 1_545 no C4 H1 3.0800 . 1_565 no C4 H13B 2.9800 . 1_545 no C4 H1O 2.791(18) . . no C6 H14B 2.8100 . 1_565 no C7 H2B 3.0900 . 1_655 no C7 H13C 2.9800 . . no C7 H13B 2.8500 . . no C9 H14C 2.9400 . 3_656 no C10 H14C 2.9400 . . no C10 H14B 2.7900 . . no C11 H14B 2.8400 . 1_565 no C12 H13B 3.0800 . 1_545 no C12 H2B 3.0400 . . no C13 H7 2.6100 . . no C13 H2A 3.0500 . 1_665 no C14 H1 2.6300 . . no C14 H2B 2.9500 . . no C14 H10 2.5600 . . no H1 C4 3.0800 . 1_545 no H1 C14 2.6300 . . no H1 H2C 2.5500 . 1_545 no H1 H14A 1.9300 . . no H1O C4 2.791(18) . . no H1O H2C 2.3900 . . no H1O H4 2.2200 . . no H1O O1 1.87(2) . 2_556 no H1O C1 2.78(2) . 2_556 no H1O H1O 2.48(3) . 2_546 no H1O H1O 2.48(3) . 2_556 no H2A C13 3.0500 . 1_445 no H2A H13B 2.5100 . 1_445 no H2B C7 3.0900 . 1_455 no H2B C12 3.0400 . . no H2B C14 2.9500 . . no H2B H14A 2.5200 . . no H2C H1 2.5500 . 1_565 no H2C H1O 2.3900 . . no H2C O1 2.8700 . 2_556 no H4 O1 2.4500 . . no H4 H1O 2.2200 . . no H4 H13A 2.3000 . . no H4 O1 2.8200 . 2_556 no H7 C13 2.6100 . . no H7 H13B 2.3500 . . no H7 H13C 2.5100 . . no H8 H9 2.5500 . 3_756 no H9 H8 2.5500 . 3_756 no H10 C14 2.5600 . . no H10 H14B 2.2700 . . no H10 H14C 2.4700 . . no H13A H4 2.3000 . . no H13B C3 2.9800 . 1_565 no H13B C4 2.9800 . 1_565 no H13B C7 2.8500 . . no H13B C12 3.0800 . 1_565 no H13B H2A 2.5100 . 1_665 no H13B H7 2.3500 . . no H13C C7 2.9800 . . no H13C H7 2.5100 . . no H14A C1 2.5100 . . no H14A C2 2.9700 . . no H14A H1 1.9300 . . no H14A H2B 2.5200 . . no H14B C6 2.8100 . 1_545 no H14B C10 2.7900 . . no H14B C11 2.8400 . 1_545 no H14B H10 2.2700 . . no H14C C10 2.9400 . . no H14C H10 2.4700 . . no H14C C9 2.9400 . 3_656 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1 H1O O1 0.89(2) 1.87(2) 2.7531(13) 177(2) 2_556 yes C4 H4 O1 0.9500 2.4500 2.8080(15) 102.00 . yes #===END