# 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 2012 _journal_volume ? _journal_page_first ? _publ_contact_author_email mark.moloney@chem.ox.ac.uk _publ_contact_author_name 'Mark G. Moloney' loop_ _publ_author_name 'Plamen Angelov' 'Sonia Chau' 'Paul J. Fryer' 'Mark G. Moloney' 'Amber L. Thompson' ; P.C.Trippier ; data_6313 _database_code_depnum_ccdc_archive 'CCDC 860455' #TrackingRef '8875_web_deposit_cif_file_0_MarkMoloney_1325590404.6313.cif' _audit_creation_date 11-02-18 _audit_creation_method CRYSTALS_ver_14.18 _oxford_structure_analysis_title 6313 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 8.4697(1) _cell_length_b 10.1103(1) _cell_length_c 13.8680(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1187.53(2) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 0.0181 0.0091 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 0.0311 0.0180 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 0.0492 0.0322 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 = C10 H17 N1 O6 # Dc = 1.38 Fooo = 528.00 Mu = 9.79 M = 247.25 # Found Formula = C10 H17 N1 O6 # Dc = 1.38 FOOO = 528.00 Mu = 9.79 M = 247.25 _chemical_formula_sum 'C10 H17 N1 O6' _chemical_formula_moiety 'C10 H17 N1 O6' _chemical_compound_source . _chemical_formula_weight 247.25 _cell_measurement_reflns_used 46839 _cell_measurement_theta_min 4 _cell_measurement_theta_max 77 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.020 _exptl_crystal_size_mid 0.260 _exptl_crystal_size_max 0.300 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 1 1 0 0.1300 0.9999 1.0003 0.0025 -0.0019 0.0401 -0.2338 -1 -1 0 0.1300 -0.9999 -1.0003 -0.0025 0.0019 -0.0401 0.2338 1 -1 0 0.1200 1.0000 -0.9997 -0.0027 0.1802 0.1532 -0.0173 -1 2 0 0.1300 -1.0001 1.9997 0.0053 -0.2713 -0.2098 -0.0909 0 0 1 0.0100 0.0000 -0.0009 0.9995 -0.0704 0.0846 0.0151 0 0 -1 0.0100 -0.0000 0.0009 -0.9995 0.0704 -0.0846 -0.0151 _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.979 # Sheldrick geometric approximatio 0.78 0.98 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies (Oxford Diffraction, 2002), Numerical absorption correction based on gaussian integration over a multifaceted crystal model Gaussian Integration (Busing and Levy, 1957) ; _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _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 59682 _reflns_number_total 2501 _diffrn_reflns_av_R_equivalents 0.043 # Number of reflections without Friedels Law is 2501 # Number of reflections with Friedels Law is 1457 # Theoretical number of reflections is about 1252 _diffrn_reflns_theta_min 5.415 _diffrn_reflns_theta_max 76.766 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 76.766 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_diffrn_Wilson_B_factor 1.75 _oxford_diffrn_Wilson_scale 0.01 _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 0.21 # 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>-3.0\s(I) _refine_ls_number_reflns 2500 _refine_ls_number_restraints 0 _refine_ls_number_parameters 155 _oxford_refine_ls_R_factor_ref 0.0226 _refine_ls_wR_factor_ref 0.0608 _refine_ls_goodness_of_fit_ref 0.9946 _refine_ls_shift/su_max 0.0006163 _refine_ls_shift/su_mean 0.0000697 # The values computed from all data _oxford_reflns_number_all 2500 _refine_ls_R_factor_all 0.0226 _refine_ls_wR_factor_all 0.0608 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2487 _refine_ls_R_factor_gt 0.0224 _refine_ls_wR_factor_gt 0.0607 _refine_ls_abs_structure_Flack 0.00(11) _refine_ls_abs_structure_details 'Flack (1983), 1044 Friedel-pairs' # 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 ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # 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^) + ( 0.04P)^2^ + 0.15P] ,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, C., 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. Busing, W.R. & Levy, H.A., (1975). Acta Cryst 10, 180. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Oxford Diffraction, (2010). CrysAlisPro. Oxford Diffraction, (2010). Supernova User Manual. 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 _atom_site_attached_hydrogens O1 O 0.4403 0.4051 0.6447 0.0205 1.0000 Uani . . . . . . C2 C 0.5136 0.5065 0.6554 0.0161 1.0000 Uani . . . . . . O3 O 0.5042 0.6107 0.5970 0.0216 1.0000 Uani . . . . . . C4 C 0.4153 0.5912 0.5088 0.0303 1.0000 Uani . . . . . . C5 C 0.6277 0.5286 0.7396 0.0149 1.0000 Uani . . . . . . N6 N 0.6609 0.6684 0.7544 0.0162 1.0000 Uani . . . . . . C7 C 0.7947 0.7111 0.7139 0.0165 1.0000 Uani . . . . . . O8 O 0.8404 0.8274 0.7142 0.0211 1.0000 Uani . . . . . . C9 C 0.8759 0.5952 0.6657 0.0182 1.0000 Uani . . . . . . C10 C 0.7963 0.4742 0.7131 0.0160 1.0000 Uani . . . . . . O11 O 0.8665 0.4419 0.8028 0.0204 1.0000 Uani . . . . . . C12 C 0.7957 0.3521 0.6482 0.0192 1.0000 Uani . . . . . . O13 O 0.7475 0.3899 0.5544 0.0222 1.0000 Uani . . . . . . C14 C 0.6993 0.2796 0.4975 0.0312 1.0000 Uani . . . . . . C15 C 1.0555 0.5985 0.6713 0.0291 1.0000 Uani . . . . . . C16 C 0.5554 0.4667 0.8304 0.0180 1.0000 Uani . . . . . . O17 O 0.3997 0.5165 0.8452 0.0233 1.0000 Uani . . . . . . H41 H 0.4076 0.6755 0.4811 0.0461 1.0000 Uiso R . . . . . H42 H 0.3128 0.5557 0.5234 0.0445 1.0000 Uiso R . . . . . H43 H 0.4729 0.5288 0.4681 0.0458 1.0000 Uiso R . . . . . H61 H 0.5995 0.7200 0.7863 0.0221 1.0000 Uiso R . . . . . H91 H 0.8437 0.5969 0.5983 0.0231 1.0000 Uiso R . . . . . H111 H 0.9531 0.4054 0.7931 0.0332 1.0000 Uiso R . . . . . H121 H 0.7261 0.2856 0.6754 0.0214 1.0000 Uiso R . . . . . H122 H 0.9012 0.3152 0.6478 0.0237 1.0000 Uiso R . . . . . H141 H 0.6117 0.2343 0.5299 0.0470 1.0000 Uiso R . . . . . H142 H 0.7905 0.2201 0.4889 0.0469 1.0000 Uiso R . . . . . H143 H 0.6647 0.3149 0.4354 0.0446 1.0000 Uiso R . . . . . H151 H 1.0968 0.6786 0.6409 0.0432 1.0000 Uiso R . . . . . H152 H 1.0926 0.5941 0.7381 0.0431 1.0000 Uiso R . . . . . H153 H 1.0978 0.5217 0.6396 0.0423 1.0000 Uiso R . . . . . H161 H 0.5539 0.3691 0.8256 0.0183 1.0000 Uiso R . . . . . H162 H 0.6219 0.4927 0.8853 0.0231 1.0000 Uiso R . . . . . H171 H 0.3373 0.4653 0.8197 0.0350 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 0.0202 0.0204 0.0209 0.0001 -0.0016 -0.0054 C2 0.0138 0.0168 0.0178 0.0011 0.0019 0.0017 O3 0.0248 0.0195 0.0205 0.0050 -0.0037 -0.0007 C4 0.0325 0.0375 0.0208 0.0064 -0.0072 0.0005 C5 0.0141 0.0123 0.0183 -0.0006 0.0004 0.0001 N6 0.0145 0.0119 0.0222 -0.0023 0.0017 0.0000 C7 0.0140 0.0168 0.0187 0.0002 -0.0013 0.0001 O8 0.0169 0.0152 0.0311 -0.0006 0.0015 -0.0023 C9 0.0161 0.0160 0.0226 -0.0001 0.0033 0.0001 C10 0.0141 0.0154 0.0184 -0.0004 0.0004 0.0012 O11 0.0170 0.0236 0.0206 0.0006 -0.0021 0.0057 C12 0.0204 0.0150 0.0221 -0.0016 0.0017 0.0025 O13 0.0288 0.0198 0.0182 -0.0029 0.0012 -0.0013 C14 0.0403 0.0278 0.0255 -0.0100 0.0038 -0.0056 C15 0.0160 0.0205 0.0506 0.0007 0.0097 0.0007 C16 0.0171 0.0189 0.0180 0.0001 0.0014 -0.0012 O17 0.0172 0.0247 0.0280 -0.0059 0.0056 -0.0021 _refine_ls_extinction_method None _oxford_refine_ls_scale 8.633 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 . 1.207 yes C2 . O3 . 1.332 yes C2 . C5 . 1.532 yes O3 . C4 . 1.450 yes C4 . H41 . 0.937 no C4 . H42 . 0.960 no C4 . H43 . 0.977 no C5 . N6 . 1.455 yes C5 . C10 . 1.573 yes C5 . C16 . 1.534 yes N6 . C7 . 1.336 yes N6 . H61 . 0.859 no C7 . O8 . 1.238 yes C7 . C9 . 1.513 yes C9 . C10 . 1.544 yes C9 . C15 . 1.524 yes C9 . H91 . 0.974 no C10 . O11 . 1.417 yes C10 . C12 . 1.528 yes O11 . H111 . 0.832 no C12 . O13 . 1.416 yes C12 . H121 . 0.971 no C12 . H122 . 0.968 no O13 . C14 . 1.426 yes C14 . H141 . 0.980 no C14 . H142 . 0.986 no C14 . H143 . 0.978 no C15 . H151 . 0.978 no C15 . H152 . 0.979 no C15 . H153 . 0.962 no C16 . O17 . 1.426 yes C16 . H161 . 0.989 no C16 . H162 . 0.983 no O17 . H171 . 0.820 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 O1 . C2 . O3 . 124.459 yes O1 . C2 . C5 . 122.870 yes O3 . C2 . C5 . 112.670 yes C2 . O3 . C4 . 115.852 yes O3 . C4 . H41 . 104.9 no O3 . C4 . H42 . 110.1 no H41 . C4 . H42 . 111.3 no O3 . C4 . H43 . 108.4 no H41 . C4 . H43 . 112.6 no H42 . C4 . H43 . 109.4 no C2 . C5 . N6 . 111.820 yes C2 . C5 . C10 . 110.116 yes N6 . C5 . C10 . 101.384 yes C2 . C5 . C16 . 108.275 yes N6 . C5 . C16 . 110.901 yes C10 . C5 . C16 . 114.296 yes C5 . N6 . C7 . 114.674 yes C5 . N6 . H61 . 123.0 no C7 . N6 . H61 . 122.3 no N6 . C7 . O8 . 124.781 yes N6 . C7 . C9 . 108.730 yes O8 . C7 . C9 . 126.456 yes C7 . C9 . C10 . 103.113 yes C7 . C9 . C15 . 114.482 yes C10 . C9 . C15 . 115.568 yes C7 . C9 . H91 . 106.5 no C10 . C9 . H91 . 107.4 no C15 . C9 . H91 . 109.1 no C9 . C10 . C5 . 102.617 yes C9 . C10 . O11 . 111.890 yes C5 . C10 . O11 . 104.878 yes C9 . C10 . C12 . 113.018 yes C5 . C10 . C12 . 114.623 yes O11 . C10 . C12 . 109.438 yes C10 . O11 . H111 . 109.3 no C10 . C12 . O13 . 108.931 yes C10 . C12 . H121 . 109.4 no O13 . C12 . H121 . 111.7 no C10 . C12 . H122 . 108.1 no O13 . C12 . H122 . 111.5 no H121 . C12 . H122 . 107.1 no C12 . O13 . C14 . 112.305 yes O13 . C14 . H141 . 109.2 no O13 . C14 . H142 . 108.7 no H141 . C14 . H142 . 111.3 no O13 . C14 . H143 . 106.7 no H141 . C14 . H143 . 110.4 no H142 . C14 . H143 . 110.5 no C9 . C15 . H151 . 110.7 no C9 . C15 . H152 . 111.5 no H151 . C15 . H152 . 109.3 no C9 . C15 . H153 . 109.4 no H151 . C15 . H153 . 109.8 no H152 . C15 . H153 . 106.0 no C5 . C16 . O17 . 110.138 yes C5 . C16 . H161 . 110.9 no O17 . C16 . H161 . 110.5 no C5 . C16 . H162 . 107.4 no O17 . C16 . H162 . 108.9 no H161 . C16 . H162 . 109.0 no C16 . O17 . H171 . 108.1 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 N6 0_555 H61 . O1 3_656 149 0.86 2.13 2.9020(14) yes O11 0_555 H111 . O8 3_746 173 0.83 1.92 2.7494(14) yes C14 0_555 H142 . O1 2_556 141 0.99 2.58 3.3976(14) yes O17 0_555 H171 . O8 3_646 167 0.82 2.11 2.9107(14) yes # Attachment '8876_web_deposit_cif_file_1_MarkMoloney_1325590404.6334.cif' ############################################################# # ***oxford university chemical crystallography group*** # # this structure was solved by amber thompson on 04/09/2011 # # this file is not publishable # a final version is available on request ############################################################# data_6334 _database_code_depnum_ccdc_archive 'CCDC 860456' #TrackingRef '8876_web_deposit_cif_file_1_MarkMoloney_1325590404.6334.cif' _audit_creation_date 11-09-04 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 6334 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 9.7787(4) _cell_length_b 10.1274(3) _cell_length_c 9.7756(3) _cell_angle_alpha 90 _cell_angle_beta 108.505(4) _cell_angle_gamma 90 _cell_volume 918.05(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall 'P 2yb' 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 0.0181 0.0091 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 0.0311 0.0180 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 0.0492 0.0322 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 = C18 H23 N1 O7 # Dc = 1.32 Fooo = 388.00 Mu = 8.57 M = 365.38 # Found Formula = C18 H23 N1 O7 # Dc = 1.32 FOOO = 388.00 Mu = 8.57 M = 365.38 _chemical_formula_sum 'C18 H23 N1 O7' _chemical_formula_moiety 'C18 H23 N1 O7' _chemical_compound_source . _chemical_formula_weight 365.38 _cell_measurement_reflns_used 7931 _cell_measurement_theta_min 4 _cell_measurement_theta_max 72 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.010 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_max 0.120 _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.857 # Sheldrick geometric approximatio 0.92 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _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 25301 _reflns_number_total 3624 _diffrn_reflns_av_R_equivalents 0.053 # Number of reflections without Friedels Law is 3624 # Number of reflections with Friedels Law is 1929 # Theoretical number of reflections is about 1822 _diffrn_reflns_theta_min 4.769 _diffrn_reflns_theta_max 72.557 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 72.557 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -12 _reflns_limit_h_max 11 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _oxford_diffrn_Wilson_B_factor 2.88 _oxford_diffrn_Wilson_scale 0.01 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.22 _refine_diff_density_max 0.16 # 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 3624 _refine_ls_number_restraints 1 _refine_ls_number_parameters 236 _oxford_refine_ls_R_factor_ref 0.0438 _refine_ls_wR_factor_ref 0.0910 _refine_ls_goodness_of_fit_ref 0.9889 _refine_ls_shift/su_max 0.0003757 _refine_ls_shift/su_mean 0.0000384 # The values computed from all data _oxford_reflns_number_all 3624 _refine_ls_R_factor_all 0.0438 _refine_ls_wR_factor_all 0.0910 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3198 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_gt 0.0865 _refine_ls_abs_structure_Flack 0.11(18) _refine_ls_abs_structure_details 'Flack (1983), 1695 Friedel-pairs' # 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 ad _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^) + ( 0.05P)^2^ + 0.17P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Oxford Diffraction, (2010). CrysAlisPro. Oxford Diffraction, (2010). Supernova User Manual. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Flack, H. D. (1983). Acta Cryst. A39, 876-881. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached 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 0.6460 0.4678 1.0614 0.0287 1.0000 Uani . . . . . . C2 C 0.7185 0.3631 1.0178 0.0234 1.0000 Uani . . . . . . C3 C 0.7648 0.4115 0.8919 0.0280 1.0000 Uani . . . . . . O4 O 0.8210 0.3048 0.8322 0.0328 1.0000 Uani . . . . . . C5 C 0.8680 0.3453 0.7132 0.0378 1.0000 Uani . . . . . . C6 C 0.7428 0.3868 0.5853 0.0368 1.0000 Uani . . . . . . C7 C 0.6470 0.2921 0.5070 0.0440 1.0000 Uani . . . . . . C8 C 0.5280 0.3277 0.3934 0.0540 1.0000 Uani . . . . . . C9 C 0.5030 0.4600 0.3562 0.0556 1.0000 Uani . . . . . . C10 C 0.5984 0.5542 0.4335 0.0537 1.0000 Uani . . . . . . C11 C 0.7177 0.5180 0.5467 0.0457 1.0000 Uani . . . . . . C12 C 0.8424 0.3209 1.1572 0.0252 1.0000 Uani . . . . . . N13 N 0.7717 0.2210 1.2181 0.0282 1.0000 Uani . . . . . . C14 C 0.6494 0.1727 1.1260 0.0270 1.0000 Uani . . . . . . C15 C 0.6249 0.2374 0.9807 0.0265 1.0000 Uani . . . . . . C16 C 0.4689 0.2624 0.8940 0.0366 1.0000 Uani . . . . . . O17 O 0.5728 0.0878 1.1552 0.0371 1.0000 Uani . . . . . . C18 C 0.8953 0.4346 1.2616 0.0282 1.0000 Uani . . . . . . O19 O 1.0091 0.3773 1.3810 0.0334 1.0000 Uani . . . . . . C20 C 1.0829 0.4592 1.4866 0.0320 1.0000 Uani . . . . . . O21 O 1.0584 0.5752 1.4877 0.0392 1.0000 Uani . . . . . . C22 C 1.1984 0.3857 1.5976 0.0472 1.0000 Uani . . . . . . C23 C 0.9684 0.2579 1.1195 0.0319 1.0000 Uani . . . . . . O24 O 1.0557 0.3507 1.0968 0.0389 1.0000 Uani . . . . . . C25 C 1.1692 0.3044 1.0433 0.0564 1.0000 Uani . . . . . . O26 O 0.9860 0.1409 1.1116 0.0430 1.0000 Uani . . . . . . H31 H 0.8367 0.4818 0.9230 0.0342 1.0000 Uiso R . . . . . H32 H 0.6801 0.4464 0.8178 0.0327 1.0000 Uiso R . . . . . H51 H 0.9340 0.4196 0.7444 0.0453 1.0000 Uiso R . . . . . H52 H 0.9153 0.2689 0.6886 0.0437 1.0000 Uiso R . . . . . H71 H 0.6626 0.2019 0.5327 0.0528 1.0000 Uiso R . . . . . H81 H 0.4662 0.2630 0.3407 0.0649 1.0000 Uiso R . . . . . H91 H 0.4196 0.4846 0.2779 0.0668 1.0000 Uiso R . . . . . H101 H 0.5811 0.6457 0.4094 0.0645 1.0000 Uiso R . . . . . H111 H 0.7829 0.5826 0.6002 0.0547 1.0000 Uiso R . . . . . H151 H 0.6671 0.1779 0.9255 0.0325 1.0000 Uiso R . . . . . H161 H 0.4168 0.1805 0.8665 0.0552 1.0000 Uiso R . . . . . H162 H 0.4216 0.3143 0.9502 0.0539 1.0000 Uiso R . . . . . H163 H 0.4642 0.3137 0.8053 0.0541 1.0000 Uiso R . . . . . H181 H 0.8186 0.4702 1.2964 0.0331 1.0000 Uiso R . . . . . H182 H 0.9337 0.5071 1.2204 0.0335 1.0000 Uiso R . . . . . H221 H 1.2231 0.4313 1.6861 0.0717 1.0000 Uiso R . . . . . H222 H 1.1660 0.2972 1.6068 0.0710 1.0000 Uiso R . . . . . H223 H 1.2807 0.3812 1.5655 0.0718 1.0000 Uiso R . . . . . H253 H 1.2177 0.3821 1.0212 0.0844 1.0000 Uiso R . . . . . H252 H 1.2353 0.2520 1.1159 0.0840 1.0000 Uiso R . . . . . H251 H 1.1261 0.2511 0.9575 0.0835 1.0000 Uiso R . . . . . H131 H 0.8138 0.1878 1.3005 0.0348 1.0000 Uiso R . . . . . H11 H 0.5805 0.5003 0.9932 0.0430 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 0.0289 0.0297 0.0210 -0.0014 -0.0011 0.0091 C2 0.0221 0.0226 0.0205 -0.0007 -0.0002 0.0017 C3 0.0300 0.0263 0.0249 0.0009 0.0048 0.0012 O4 0.0371 0.0341 0.0272 -0.0014 0.0103 0.0034 C5 0.0359 0.0484 0.0323 -0.0023 0.0152 -0.0003 C6 0.0418 0.0443 0.0264 -0.0034 0.0138 -0.0026 C7 0.0492 0.0423 0.0357 -0.0017 0.0063 -0.0002 C8 0.0552 0.0585 0.0387 -0.0090 0.0014 -0.0074 C9 0.0585 0.0680 0.0333 0.0074 0.0046 0.0084 C10 0.0700 0.0500 0.0427 0.0113 0.0200 0.0064 C11 0.0537 0.0489 0.0369 0.0002 0.0179 -0.0054 C12 0.0235 0.0232 0.0229 -0.0003 -0.0009 0.0004 N13 0.0292 0.0267 0.0203 0.0047 -0.0040 -0.0026 C14 0.0284 0.0242 0.0213 0.0008 -0.0023 -0.0032 C15 0.0273 0.0265 0.0195 -0.0009 -0.0013 -0.0016 C16 0.0283 0.0370 0.0316 0.0076 -0.0088 -0.0066 O17 0.0397 0.0359 0.0261 0.0047 -0.0033 -0.0144 C18 0.0264 0.0254 0.0242 -0.0021 -0.0043 0.0007 O19 0.0324 0.0265 0.0280 -0.0024 -0.0092 0.0008 C20 0.0302 0.0338 0.0247 -0.0046 -0.0017 -0.0042 O21 0.0408 0.0318 0.0340 -0.0078 -0.0035 -0.0017 C22 0.0432 0.0448 0.0353 -0.0041 -0.0135 0.0023 C23 0.0259 0.0350 0.0279 -0.0036 -0.0011 0.0025 O24 0.0250 0.0469 0.0427 -0.0059 0.0078 -0.0011 C25 0.0312 0.0798 0.0601 -0.0085 0.0172 0.0042 O26 0.0411 0.0348 0.0473 -0.0027 0.0058 0.0120 _refine_ls_extinction_method None _oxford_refine_ls_scale 8.446 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 . 1.414 yes O1 . H11 . 0.832 no C2 . C3 . 1.521 yes C2 . C12 . 1.568 yes C2 . C15 . 1.542 yes C3 . O4 . 1.420 yes C3 . H31 . 0.978 no C3 . H32 . 0.976 no O4 . C5 . 1.439 yes C5 . C6 . 1.505 yes C5 . H51 . 0.976 no C5 . H52 . 0.970 no C6 . C7 . 1.389 yes C6 . C11 . 1.382 yes C7 . C8 . 1.377 yes C7 . H71 . 0.947 no C8 . C9 . 1.389 yes C8 . H81 . 0.929 no C9 . C10 . 1.380 yes C9 . H91 . 0.957 no C10 . C11 . 1.379 yes C10 . H101 . 0.958 no C11 . H111 . 0.946 no C12 . N13 . 1.455 yes C12 . C18 . 1.517 yes C12 . C23 . 1.533 yes N13 . C14 . 1.340 yes N13 . H131 . 0.849 no C14 . C15 . 1.513 yes C14 . O17 . 1.232 yes C15 . C16 . 1.513 yes C15 . H151 . 0.982 no C16 . H161 . 0.966 no C16 . H162 . 0.977 no C16 . H163 . 0.998 no C18 . O19 . 1.454 yes C18 . H181 . 0.985 no C18 . H182 . 0.968 no O19 . C20 . 1.342 yes C20 . O21 . 1.200 yes C20 . C22 . 1.493 yes C22 . H221 . 0.942 no C22 . H222 . 0.964 no C22 . H223 . 0.953 no C23 . O24 . 1.335 yes C23 . O26 . 1.203 yes O24 . C25 . 1.447 yes C25 . H253 . 0.977 no C25 . H252 . 0.955 no C25 . H251 . 0.974 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 . H11 . 112.8 no O1 . C2 . C3 . 107.953 yes O1 . C2 . C12 . 105.384 yes C3 . C2 . C12 . 116.437 yes O1 . C2 . C15 . 111.874 yes C3 . C2 . C15 . 112.483 yes C12 . C2 . C15 . 102.515 yes C2 . C3 . O4 . 109.910 yes C2 . C3 . H31 . 110.6 no O4 . C3 . H31 . 110.4 no C2 . C3 . H32 . 108.5 no O4 . C3 . H32 . 108.6 no H31 . C3 . H32 . 108.9 no C3 . O4 . C5 . 112.333 yes O4 . C5 . C6 . 111.507 yes O4 . C5 . H51 . 108.4 no C6 . C5 . H51 . 109.1 no O4 . C5 . H52 . 105.8 no C6 . C5 . H52 . 110.0 no H51 . C5 . H52 . 111.9 no C5 . C6 . C7 . 119.583 yes C5 . C6 . C11 . 121.480 yes C7 . C6 . C11 . 118.894 yes C6 . C7 . C8 . 120.877 yes C6 . C7 . H71 . 119.7 no C8 . C7 . H71 . 119.4 no C7 . C8 . C9 . 119.822 yes C7 . C8 . H81 . 119.8 no C9 . C8 . H81 . 120.4 no C8 . C9 . C10 . 119.403 yes C8 . C9 . H91 . 119.6 no C10 . C9 . H91 . 121.0 no C9 . C10 . C11 . 120.582 yes C9 . C10 . H101 . 119.9 no C11 . C10 . H101 . 119.5 no C6 . C11 . C10 . 120.418 yes C6 . C11 . H111 . 118.9 no C10 . C11 . H111 . 120.7 no C2 . C12 . N13 . 102.053 yes C2 . C12 . C18 . 112.489 yes N13 . C12 . C18 . 110.939 yes C2 . C12 . C23 . 111.254 yes N13 . C12 . C23 . 109.376 yes C18 . C12 . C23 . 110.434 yes C12 . N13 . C14 . 114.645 yes C12 . N13 . H131 . 120.9 no C14 . N13 . H131 . 123.6 no N13 . C14 . C15 . 108.322 yes N13 . C14 . O17 . 125.263 yes C15 . C14 . O17 . 126.395 yes C2 . C15 . C14 . 103.381 yes C2 . C15 . C16 . 114.299 yes C14 . C15 . C16 . 115.429 yes C2 . C15 . H151 . 108.3 no C14 . C15 . H151 . 106.3 no C16 . C15 . H151 . 108.6 no C15 . C16 . H161 . 111.2 no C15 . C16 . H162 . 110.4 no H161 . C16 . H162 . 108.4 no C15 . C16 . H163 . 109.5 no H161 . C16 . H163 . 109.3 no H162 . C16 . H163 . 108.0 no C12 . C18 . O19 . 104.350 yes C12 . C18 . H181 . 112.0 no O19 . C18 . H181 . 109.9 no C12 . C18 . H182 . 113.0 no O19 . C18 . H182 . 109.8 no H181 . C18 . H182 . 107.7 no C18 . O19 . C20 . 117.260 yes O19 . C20 . O21 . 123.521 yes O19 . C20 . C22 . 110.397 yes O21 . C20 . C22 . 126.074 yes C20 . C22 . H221 . 109.7 no C20 . C22 . H222 . 109.7 no H221 . C22 . H222 . 111.5 no C20 . C22 . H223 . 107.9 no H221 . C22 . H223 . 109.1 no H222 . C22 . H223 . 108.9 no C12 . C23 . O24 . 110.617 yes C12 . C23 . O26 . 124.577 yes O24 . C23 . O26 . 124.806 yes C23 . O24 . C25 . 115.844 yes O24 . C25 . H253 . 107.5 no O24 . C25 . H252 . 109.1 no H253 . C25 . H252 . 110.5 no O24 . C25 . H251 . 108.6 no H253 . C25 . H251 . 111.3 no H252 . C25 . H251 . 109.8 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 C3 0_555 H31 . O26 0_757 154 0.98 2.47 3.375(3) yes C16 0_555 H161 . O1 2_647 148 0.97 2.41 3.266(3) yes N13 0_555 H131 . O21 0_748 173 0.85 2.35 3.190(3) yes O1 . H11 . O17 0_657 175 0.83 1.94 2.768(3) yes