# Electronic Supplementary Material (ESI) for Chemical Science # 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_shre267p _database_code_depnum_ccdc_archive 'CCDC 900416' #TrackingRef '13792_web_deposit_cif_file_0_DavidLey_1346947993.CIF_FOR_DEPOSIT.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; tert.-butylglyoxylic acid dimer ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 O6' _chemical_formula_weight 260.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M p_1_21/c_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.0689(6) _cell_length_b 11.6990(13) _cell_length_c 19.4385(19) _cell_angle_alpha 90.00 _cell_angle_beta 98.695(11) _cell_angle_gamma 90.00 _cell_volume 1364.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10823 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2774 _reflns_number_gt 2346 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2774 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1566 _refine_ls_wR_factor_gt 0.1452 _refine_ls_goodness_of_fit_ref 0.686 _refine_ls_restrained_S_all 0.686 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.37867(14) 0.22358(6) 0.15439(4) 0.0208(2) Uani 1 1 d . . . O2 O 0.05018(14) 0.13710(7) 0.11526(5) 0.0259(3) Uani 1 1 d . . . O3 O 0.54593(17) 0.12790(8) 0.04014(6) 0.0396(3) Uani 1 1 d . . . O4 O 0.47464(16) 0.04024(7) 0.19407(5) 0.0306(3) Uani 1 1 d . . . O5 O 0.24310(18) 0.01771(9) 0.03061(6) 0.0427(3) Uani 1 1 d . . . O6 O -0.02029(18) 0.05370(8) 0.21239(6) 0.0384(3) Uani 1 1 d . . . C7 C 0.23836(19) 0.19342(9) 0.09311(6) 0.0222(3) Uani 1 1 d . . . C8 C 0.1578(2) 0.30095(10) 0.05067(7) 0.0278(3) Uani 1 1 d . . . C9 C 0.3560(2) 0.10593(10) 0.05140(7) 0.0261(3) Uani 1 1 d . . . C10 C 0.1074(2) 0.10300(9) 0.18121(7) 0.0264(3) Uani 1 1 d . . . C11 C 0.4065(2) 0.19014(11) 0.27782(7) 0.0303(3) Uani 1 1 d . . . C12 C 0.3602(3) 0.37063(11) 0.03674(8) 0.0339(3) Uani 1 1 d . . . H12A H 0.4473 0.3922 0.0802 0.051 Uiso 1 1 calc R . . H12B H 0.3105 0.4381 0.0108 0.051 Uiso 1 1 calc R . . H12C H 0.4498 0.3253 0.0105 0.051 Uiso 1 1 calc R . . C13 C 0.3522(2) 0.13838(9) 0.20482(7) 0.0241(3) Uani 1 1 d . . . C14 C 0.2507(3) 0.29018(13) 0.28546(9) 0.0379(4) Uani 1 1 d . . . H14A H 0.2672 0.3472 0.2511 0.057 Uiso 1 1 calc R . . H14B H 0.2875 0.3227 0.3311 0.057 Uiso 1 1 calc R . . H14C H 0.0993 0.2636 0.2790 0.057 Uiso 1 1 calc R . . C15 C 0.0171(3) 0.26598(14) -0.01788(9) 0.0437(4) Uani 1 1 d . . . H15A H 0.1055 0.2204 -0.0444 0.066 Uiso 1 1 calc R . . H15B H -0.0339 0.3332 -0.0439 0.066 Uiso 1 1 calc R . . H15C H -0.1090 0.2223 -0.0085 0.066 Uiso 1 1 calc R . . C16 C 0.0174(3) 0.37311(13) 0.09330(10) 0.0428(4) Uani 1 1 d . . . H16A H 0.1063 0.3949 0.1364 0.064 Uiso 1 1 calc R . . H16B H -0.1084 0.3293 0.1027 0.064 Uiso 1 1 calc R . . H16C H -0.0339 0.4404 0.0675 0.064 Uiso 1 1 calc R . . C17 C 0.6462(3) 0.23400(15) 0.28834(9) 0.0426(4) Uani 1 1 d . . . H17A H 0.6619 0.2910 0.2539 0.064 Uiso 1 1 calc R . . H17B H 0.7459 0.1717 0.2838 0.064 Uiso 1 1 calc R . . H17C H 0.6815 0.2669 0.3339 0.064 Uiso 1 1 calc R . . C18 C 0.3789(4) 0.09839(17) 0.33174(9) 0.0582(5) Uani 1 1 d . . . H18A H 0.4131 0.1303 0.3776 0.087 Uiso 1 1 calc R . . H18B H 0.4783 0.0360 0.3270 0.087 Uiso 1 1 calc R . . H18C H 0.2279 0.0712 0.3245 0.087 Uiso 1 1 calc R . . H19 H 0.6150 0.0599 0.1930 0.072(7) Uiso 1 1 d R . . H20 H 0.3067 -0.0248 0.0040 0.143(15) Uiso 1 1 d 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 0.0200(4) 0.0187(4) 0.0235(5) 0.0012(3) 0.0023(4) -0.0017(3) O2 0.0171(5) 0.0267(4) 0.0348(5) -0.0003(3) 0.0062(4) -0.0038(3) O3 0.0298(6) 0.0353(5) 0.0580(7) -0.0130(4) 0.0210(5) -0.0083(4) O4 0.0299(5) 0.0197(4) 0.0432(6) 0.0025(3) 0.0089(5) 0.0063(3) O5 0.0326(6) 0.0376(5) 0.0595(7) -0.0247(5) 0.0123(6) -0.0118(4) O6 0.0362(6) 0.0307(5) 0.0525(7) 0.0057(4) 0.0208(5) -0.0065(4) C7 0.0165(6) 0.0225(5) 0.0277(6) -0.0014(4) 0.0038(5) -0.0027(4) C8 0.0231(6) 0.0286(6) 0.0302(7) 0.0052(5) -0.0006(6) -0.0007(4) C9 0.0231(6) 0.0259(6) 0.0299(6) -0.0055(4) 0.0060(5) -0.0038(4) C10 0.0259(6) 0.0170(5) 0.0381(7) 0.0001(4) 0.0109(6) 0.0005(4) C11 0.0315(7) 0.0341(7) 0.0256(6) 0.0008(5) 0.0055(6) 0.0026(5) C12 0.0331(7) 0.0292(6) 0.0377(8) 0.0092(5) -0.0005(6) -0.0060(5) C13 0.0245(6) 0.0186(5) 0.0302(6) 0.0042(4) 0.0078(5) 0.0026(4) C14 0.0336(8) 0.0386(7) 0.0432(8) -0.0131(6) 0.0113(7) -0.0001(5) C15 0.0383(9) 0.0508(9) 0.0368(8) 0.0113(6) -0.0113(7) -0.0098(6) C16 0.0419(9) 0.0359(7) 0.0512(9) 0.0093(6) 0.0093(8) 0.0183(6) C17 0.0297(8) 0.0622(10) 0.0340(8) -0.0102(7) -0.0018(7) 0.0037(6) C18 0.0880(16) 0.0566(10) 0.0314(8) 0.0138(7) 0.0131(10) 0.0061(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.4007(15) . ? O1 C13 1.4240(13) . ? O2 C10 1.3374(17) . ? O2 C7 1.4396(13) . ? O3 C9 1.2325(16) . ? O4 C13 1.4003(13) . ? O5 C9 1.2705(16) . ? O6 C10 1.2012(15) . ? C7 C8 1.5428(17) . ? C7 C9 1.5459(15) . ? C8 C15 1.526(2) . ? C8 C16 1.5294(19) . ? C8 C12 1.5323(17) . ? C10 C13 1.5437(18) . ? C11 C14 1.5258(18) . ? C11 C17 1.527(2) . ? C11 C18 1.527(2) . ? C11 C13 1.5322(18) . ? 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_3 _geom_angle_publ_flag C7 O1 C13 106.97(9) . . ? C10 O2 C7 108.68(10) . . ? O1 C7 O2 105.59(9) . . ? O1 C7 C8 110.62(9) . . ? O2 C7 C8 109.37(10) . . ? O1 C7 C9 110.07(10) . . ? O2 C7 C9 107.70(9) . . ? C8 C7 C9 113.18(10) . . ? C15 C8 C16 109.69(13) . . ? C15 C8 C12 110.26(11) . . ? C16 C8 C12 109.24(12) . . ? C15 C8 C7 109.79(11) . . ? C16 C8 C7 108.53(10) . . ? C12 C8 C7 109.30(11) . . ? O3 C9 O5 125.93(11) . . ? O3 C9 C7 118.27(11) . . ? O5 C9 C7 115.79(10) . . ? O6 C10 O2 122.20(13) . . ? O6 C10 C13 130.11(13) . . ? O2 C10 C13 107.69(9) . . ? C14 C11 C17 108.73(12) . . ? C14 C11 C18 109.79(12) . . ? C17 C11 C18 110.21(15) . . ? C14 C11 C13 110.10(12) . . ? C17 C11 C13 108.89(10) . . ? C18 C11 C13 109.10(12) . . ? O4 C13 O1 110.71(9) . . ? O4 C13 C11 114.69(11) . . ? O1 C13 C11 109.28(9) . . ? O4 C13 C10 104.14(9) . . ? O1 C13 C10 100.75(10) . . ? C11 C13 C10 116.34(10) . . ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 0.352 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.042 #===END OF DATA FOR 1 #===END OF ALL DATA