# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jeremy Robertson' _publ_contact_author_email jeremy.robertson@chem.ox.ac.uk _publ_author_name J.Robertson data_AxOH _database_code_depnum_ccdc_archive 'CCDC 842957' #TrackingRef 'AxOH.cif' _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. 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, N---H in the range 0.86--0.89 N---H to 0.86 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 with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 7.0008(2) _cell_length_b 9.0561(2) _cell_length_c 24.0388(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1524.06(6) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C8 H10 O4 # Dc = 1.48 Fooo = 720.00 Mu = 1.20 M = 170.16 # Found Formula = C8 H10 O4 # Dc = 1.48 FOOO = 720.00 Mu = 1.20 M = 170.16 _chemical_formula_sum 'C8 H10 O4' _chemical_formula_moiety 'C8 H10 O4' _chemical_compound_source ? _chemical_formula_weight 170.16 _cell_measurement_reflns_used 1982 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.16 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.24 _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.120 # Sheldrick geometric approximatio 0.98 0.98 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.98 # 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 \w # 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 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 3461 _reflns_number_total 1723 _diffrn_reflns_av_R_equivalents 0.024 # Number of reflections with Friedels Law is 1723 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1743 _diffrn_reflns_theta_min 5.172 _diffrn_reflns_theta_max 27.454 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.454 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _reflns_limit_h_min 0 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 30 _oxford_diffrn_Wilson_B_factor 2.04 _oxford_diffrn_Wilson_scale 3.24 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.34 _refine_diff_density_max 0.32 # 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>-3.0\s(I) _refine_ls_number_reflns 1723 _refine_ls_number_restraints 0 _refine_ls_number_parameters 109 _oxford_refine_ls_R_factor_ref 0.0536 _refine_ls_wR_factor_ref 0.1020 _refine_ls_goodness_of_fit_ref 1.0222 _refine_ls_shift/su_max 0.000360 # The values computed from all data _oxford_reflns_number_all 1723 _refine_ls_R_factor_all 0.0536 _refine_ls_wR_factor_all 0.1020 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1276 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_gt 0.0972 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # 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 0.47487(13) 0.20068(10) 0.38659(3) 0.0225 1.0000 Uani . . . . . . . C2 C 0.48759(19) 0.16096(14) 0.32821(5) 0.0230 1.0000 Uani . . . . . . . C3 C 0.60029(18) 0.27413(14) 0.29540(5) 0.0220 1.0000 Uani . . . . . . . O4 O 0.79742(12) 0.27413(11) 0.31079(4) 0.0268 1.0000 Uani . . . . . . . C5 C 0.50921(18) 0.42561(14) 0.30253(5) 0.0237 1.0000 Uani . . . . . . . C6 C 0.49055(17) 0.46425(14) 0.36384(5) 0.0216 1.0000 Uani . . . . . . . C7 C 0.39429(18) 0.34024(13) 0.39634(5) 0.0206 1.0000 Uani . . . . . . . O8 O 0.19158(11) 0.33573(10) 0.38095(4) 0.0213 1.0000 Uani . . . . . . . C9 C 0.08354(19) 0.35831(14) 0.42698(5) 0.0223 1.0000 Uani . . . . . . . O10 O -0.08910(13) 0.35648(11) 0.42499(4) 0.0297 1.0000 Uani . . . . . . . C11 C 0.21091(19) 0.38001(15) 0.47532(6) 0.0272 1.0000 Uani . . . . . . . C12 C 0.38908(19) 0.36611(14) 0.45784(5) 0.0246 1.0000 Uani . . . . . . . H21 H 0.5490 0.0648 0.3278 0.0259 1.0000 Uiso R . . . . . . H22 H 0.3538 0.1507 0.3129 0.0258 1.0000 Uiso R . . . . . . H31 H 0.6013 0.2443 0.2550 0.0245 1.0000 Uiso R . . . . . . H51 H 0.5866 0.5073 0.2839 0.0267 1.0000 Uiso R . . . . . . H52 H 0.3816 0.4193 0.2851 0.0260 1.0000 Uiso R . . . . . . H61 H 0.6233 0.4857 0.3804 0.0254 1.0000 Uiso R . . . . . . H62 H 0.4175 0.5564 0.3703 0.0257 1.0000 Uiso R . . . . . . H111 H 0.1692 0.4013 0.5118 0.0321 1.0000 Uiso R . . . . . . H121 H 0.5019 0.3711 0.4797 0.0273 1.0000 Uiso R . . . . . . H9 H 0.8013 0.2924 0.3481 0.0408 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 0.0256(5) 0.0187(5) 0.0233(5) 0.0000(3) 0.0010(4) 0.0033(4) C2 0.0256(7) 0.0178(6) 0.0254(7) -0.0039(5) 0.0016(5) 0.0002(6) C3 0.0203(6) 0.0232(7) 0.0225(6) -0.0017(5) -0.0001(5) -0.0002(5) O4 0.0196(5) 0.0324(6) 0.0284(5) -0.0003(4) 0.0026(3) 0.0017(4) C5 0.0238(7) 0.0212(7) 0.0261(6) 0.0031(5) -0.0023(5) -0.0012(6) C6 0.0204(6) 0.0165(6) 0.0280(7) -0.0012(5) -0.0020(5) 0.0002(5) C7 0.0165(6) 0.0201(7) 0.0251(6) -0.0026(5) -0.0031(5) 0.0015(5) O8 0.0168(5) 0.0254(5) 0.0217(4) -0.0036(3) -0.0009(3) -0.0001(4) C9 0.0235(7) 0.0209(7) 0.0225(6) -0.0018(5) 0.0026(5) -0.0001(5) O10 0.0213(5) 0.0374(6) 0.0304(5) -0.0015(4) 0.0025(4) -0.0008(4) C11 0.0306(8) 0.0291(8) 0.0220(6) -0.0046(5) -0.0010(5) 0.0022(6) C12 0.0273(7) 0.0236(7) 0.0228(7) -0.0025(5) -0.0056(5) 0.0025(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.5422(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 . C2 . 1.4514(15) yes O1 . C7 . 1.4038(15) yes C2 . C3 . 1.5150(18) yes C2 . H21 . 0.971 no C2 . H22 . 1.011 no C3 . O4 . 1.4288(15) yes C3 . C5 . 1.5224(18) yes C3 . H31 . 1.009 no O4 . H9 . 0.912 no C5 . C6 . 1.5205(18) yes C5 . H51 . 1.021 no C5 . H52 . 0.988 no C6 . C7 . 1.5249(18) yes C6 . H61 . 1.029 no C6 . H62 . 0.991 no C7 . O8 . 1.4671(15) yes C7 . C12 . 1.4974(18) yes O8 . C9 . 1.3558(15) yes C9 . O10 . 1.2097(16) yes C9 . C11 . 1.4779(18) yes C11 . C12 . 1.3222(19) yes C11 . H111 . 0.945 no C12 . H121 . 0.950 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C7 . 114.16(9) yes O1 . C2 . C3 . 111.58(10) yes O1 . C2 . H21 . 105.0 no C3 . C2 . H21 . 111.7 no O1 . C2 . H22 . 108.6 no C3 . C2 . H22 . 110.8 no H21 . C2 . H22 . 108.9 no C2 . C3 . O4 . 111.60(10) yes C2 . C3 . C5 . 109.44(10) yes O4 . C3 . C5 . 112.05(10) yes C2 . C3 . H31 . 108.9 no O4 . C3 . H31 . 104.0 no C5 . C3 . H31 . 110.7 no C3 . O4 . H9 . 106.4 no C3 . C5 . C6 . 110.64(10) yes C3 . C5 . H51 . 112.4 no C6 . C5 . H51 . 107.8 no C3 . C5 . H52 . 106.2 no C6 . C5 . H52 . 110.2 no H51 . C5 . H52 . 109.6 no C5 . C6 . C7 . 111.41(10) yes C5 . C6 . H61 . 109.9 no C7 . C6 . H61 . 109.8 no C5 . C6 . H62 . 113.0 no C7 . C6 . H62 . 108.2 no H61 . C6 . H62 . 104.3 no C6 . C7 . O1 . 113.57(10) yes C6 . C7 . O8 . 108.59(10) yes O1 . C7 . O8 . 108.75(9) yes C6 . C7 . C12 . 113.66(11) yes O1 . C7 . C12 . 108.39(10) yes O8 . C7 . C12 . 103.28(10) yes C7 . O8 . C9 . 109.25(9) yes O8 . C9 . O10 . 121.54(11) yes O8 . C9 . C11 . 108.97(11) yes O10 . C9 . C11 . 129.47(12) yes C9 . C11 . C12 . 107.86(12) yes C9 . C11 . H111 . 124.8 no C12 . C11 . H111 . 127.3 no C7 . C12 . C11 . 110.59(11) yes C7 . C12 . H121 . 122.2 no C11 . C12 . H121 . 127.2 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 C6 . H61 . O10 1_655 142 1.03 2.56 3.4312(18) yes O4 . H9 . O10 1_655 159 0.91 2.08 2.9537(18) yes # Attachment 'EqOH.cif' data_EqOH _database_code_depnum_ccdc_archive 'CCDC 842958' #TrackingRef 'EqOH.cif' _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. 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, N---H in the range 0.86--0.89 N---H to 0.86 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 with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 7.5000(3) _cell_length_b 6.0089(2) _cell_length_c 17.9334(7) _cell_angle_alpha 90 _cell_angle_beta 94.8761(15) _cell_angle_gamma 90 _cell_volume 805.28(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C8 H10 O4 # Dc = 1.40 Fooo = 360.00 Mu = 1.13 M = 170.16 # Found Formula = C8 H10 O4 # Dc = 1.40 FOOO = 360.00 Mu = 1.13 M = 170.16 _chemical_formula_sum 'C8 H10 O4' _chemical_formula_moiety 'C8 H10 O4' _chemical_compound_source ? _chemical_formula_weight 170.16 _cell_measurement_reflns_used 1898 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.113 # Sheldrick geometric approximatio 0.99 0.99 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 # 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 \w # 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 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 3347 _reflns_number_total 1822 _diffrn_reflns_av_R_equivalents 0.023 # Number of reflections with Friedels Law is 1822 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1850 _diffrn_reflns_theta_min 5.458 _diffrn_reflns_theta_max 27.498 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.398 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _oxford_diffrn_Wilson_B_factor 2.48 _oxford_diffrn_Wilson_scale 0.44 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.27 _refine_diff_density_max 0.34 # 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>-3.0\s(I) _refine_ls_number_reflns 1822 _refine_ls_number_restraints 0 _refine_ls_number_parameters 109 _oxford_refine_ls_R_factor_ref 0.0610 _refine_ls_wR_factor_ref 0.1670 _refine_ls_goodness_of_fit_ref 1.2426 _refine_ls_shift/su_max 0.000341 # The values computed from all data _oxford_reflns_number_all 1822 _refine_ls_R_factor_all 0.0610 _refine_ls_wR_factor_all 0.1670 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1492 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_gt 0.1581 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.10P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # 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 O121 O 0.46688(15) 0.13549(18) 0.68804(6) 0.0275 1.0000 Uani . . . . . . . O2 O 0.63591(16) -0.0996(2) 0.76025(7) 0.0373 1.0000 Uani . . . . . . . O3 O 0.32095(15) 0.1517(2) 0.56770(6) 0.0307 1.0000 Uani . . . . . . . O4 O -0.02542(16) 0.5636(2) 0.60381(7) 0.0381 1.0000 Uani . . . . . . . C5 C 0.4694(2) 0.2294(3) 0.61263(8) 0.0254 1.0000 Uani . . . . . . . C6 C 0.7119(2) -0.0084(3) 0.63495(9) 0.0301 1.0000 Uani . . . . . . . C7 C 0.6092(2) -0.0019(3) 0.70153(9) 0.0285 1.0000 Uani . . . . . . . C8 C 0.1505(2) 0.2357(3) 0.58707(10) 0.0320 1.0000 Uani . . . . . . . C9 C 0.6321(2) 0.1252(3) 0.58392(9) 0.0302 1.0000 Uani . . . . . . . C10 C 0.2974(2) 0.5730(3) 0.64146(9) 0.0325 1.0000 Uani . . . . . . . C11 C 0.1462(2) 0.4872(3) 0.58713(9) 0.0307 1.0000 Uani . . . . . . . C12 C 0.4759(2) 0.4812(3) 0.61986(9) 0.0297 1.0000 Uani . . . . . . . H61 H 0.8146 -0.0952 0.6317 0.0347 1.0000 Uiso R . . . . . . H81 H 0.1280 0.1825 0.6354 0.0370 1.0000 Uiso R . . . . . . H82 H 0.0606 0.1783 0.5509 0.0385 1.0000 Uiso R . . . . . . H91 H 0.6708 0.1616 0.5341 0.0351 1.0000 Uiso R . . . . . . H101 H 0.2819 0.5163 0.6903 0.0370 1.0000 Uiso R . . . . . . H102 H 0.2916 0.7371 0.6411 0.0391 1.0000 Uiso R . . . . . . H111 H 0.1580 0.5344 0.5331 0.0356 1.0000 Uiso R . . . . . . H121 H 0.5772 0.5231 0.6561 0.0355 1.0000 Uiso R . . . . . . H122 H 0.5015 0.5422 0.5725 0.0339 1.0000 Uiso R . . . . . . H9 H -0.0387 0.5214 0.6499 0.0547 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 O121 0.0276(6) 0.0257(6) 0.0295(6) 0.0023(4) 0.0043(4) 0.0039(4) O2 0.0385(7) 0.0347(7) 0.0382(7) 0.0089(5) 0.0009(5) 0.0052(5) O3 0.0271(7) 0.0295(7) 0.0351(7) -0.0071(5) -0.0003(5) 0.0023(5) O4 0.0304(7) 0.0413(8) 0.0426(7) 0.0035(6) 0.0029(5) 0.0130(6) C5 0.0261(8) 0.0251(8) 0.0249(8) 0.0000(6) 0.0019(6) 0.0015(6) C6 0.0240(8) 0.0266(9) 0.0398(9) -0.0042(6) 0.0033(6) 0.0022(6) C7 0.0248(8) 0.0231(8) 0.0369(9) -0.0019(6) -0.0009(6) -0.0001(6) C8 0.0250(8) 0.0313(9) 0.0390(9) -0.0052(7) -0.0013(6) 0.0004(7) C9 0.0291(9) 0.0278(9) 0.0344(9) -0.0037(6) 0.0062(6) 0.0003(7) C10 0.0339(9) 0.0228(8) 0.0403(10) -0.0019(7) 0.0002(7) 0.0034(7) C11 0.0269(8) 0.0311(9) 0.0339(9) 0.0037(6) 0.0019(6) 0.0071(7) C12 0.0298(8) 0.0228(8) 0.0362(8) 0.0012(6) 0.0008(6) 0.0006(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.52(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 O121 . C5 . 1.4669(18) yes O121 . C7 . 1.3551(19) yes O2 . C7 . 1.207(2) yes O3 . C5 . 1.3982(19) yes O3 . C8 . 1.4441(19) yes O4 . C11 . 1.4225(19) yes O4 . H9 . 0.878 no C5 . C9 . 1.500(2) yes C5 . C12 . 1.519(2) yes C6 . C7 . 1.475(2) yes C6 . C9 . 1.322(2) yes C6 . H61 . 0.936 no C8 . C11 . 1.511(3) yes C8 . H81 . 0.953 no C8 . H82 . 0.959 no C9 . H91 . 0.986 no C10 . C11 . 1.521(2) yes C10 . C12 . 1.528(2) yes C10 . H101 . 0.956 no C10 . H102 . 0.987 no C11 . H111 . 1.021 no C12 . H121 . 0.990 no C12 . H122 . 0.959 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 . O121 . C7 . 109.09(12) yes C5 . O3 . C8 . 114.99(12) yes C11 . O4 . H9 . 106.4 no O121 . C5 . O3 . 109.31(12) yes O121 . C5 . C9 . 103.33(12) yes O3 . C5 . C9 . 107.09(12) yes O121 . C5 . C12 . 107.90(12) yes O3 . C5 . C12 . 113.57(13) yes C9 . C5 . C12 . 115.07(13) yes C7 . C6 . C9 . 107.88(14) yes C7 . C6 . H61 . 123.6 no C9 . C6 . H61 . 128.5 no C6 . C7 . O121 . 109.23(14) yes C6 . C7 . O2 . 129.32(15) yes O121 . C7 . O2 . 121.44(15) yes O3 . C8 . C11 . 111.65(13) yes O3 . C8 . H81 . 109.3 no C11 . C8 . H81 . 109.3 no O3 . C8 . H82 . 107.3 no C11 . C8 . H82 . 110.3 no H81 . C8 . H82 . 109.0 no C5 . C9 . C6 . 110.46(14) yes C5 . C9 . H91 . 121.9 no C6 . C9 . H91 . 127.6 no C11 . C10 . C12 . 109.69(14) yes C11 . C10 . H101 . 108.9 no C12 . C10 . H101 . 106.3 no C11 . C10 . H102 . 107.7 no C12 . C10 . H102 . 113.4 no H101 . C10 . H102 . 110.7 no C10 . C11 . C8 . 108.94(14) yes C10 . C11 . O4 . 113.24(14) yes C8 . C11 . O4 . 110.02(14) yes C10 . C11 . H111 . 113.2 no C8 . C11 . H111 . 105.9 no O4 . C11 . H111 . 105.2 no C10 . C12 . C5 . 111.01(13) yes C10 . C12 . H121 . 112.4 no C5 . C12 . H121 . 109.1 no C10 . C12 . H122 . 109.4 no C5 . C12 . H122 . 108.2 no H121 . C12 . H122 . 106.6 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 C6 . H61 . O4 1_645 154 0.94 2.45 3.315(2) yes O4 . H9 . O2 3_556 163 0.88 1.96 2.817(2) yes