# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email colin.seaton@ul.ie _publ_contact_author_name 'Colin C. Seaton' loop_ _publ_author_name 'Roger J. Davey' 'Ghazala Sadiq' 'Kevin Back' 'Laura Wilkinson' C.Seaton data_2CLMA _database_code_depnum_ccdc_archive 'CCDC 838590' #TrackingRef '6656_web_deposit_cif_file_0_ColinSeaton_1312905188.S_2CLMA.cif' _chemical_name_systematic ; S-(2-chlorophenyl)(hydroxy)acetic acid ; _chemical_name_common '(S)-2-chloromandelic acid' _chemical_melting_point ? _chemical_formula_moiety 'C8 H7 Cl O3' _chemical_formula_sum 'C8 H7 Cl O3' _chemical_formula_weight 186.59 _chemical_absolute_configuration rmad 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' Cl Cl 0.1484 0.1585 '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 1' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.0612(4) _cell_length_b 7.4986(3) _cell_length_c 13.8910(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.997(5) _cell_angle_gamma 90.00 _cell_volume 807.16(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2933 _cell_measurement_theta_min 3.1069 _cell_measurement_theta_max 28.4391 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.432 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.85733 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3367 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5399 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 28.50 _diffrn_orient_matrix_UB_11 -0.0612108801 _diffrn_orient_matrix_UB_12 -0.0256914653 _diffrn_orient_matrix_UB_13 0.0255450219 _diffrn_orient_matrix_UB_21 0.0631092126 _diffrn_orient_matrix_UB_22 0.0122006106 _diffrn_orient_matrix_UB_23 0.0466274257 _diffrn_orient_matrix_UB_31 -0.0259613667 _diffrn_orient_matrix_UB_32 0.0902280074 _diffrn_orient_matrix_UB_33 0.0009681230 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -107.00 78.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -21.2308 0.0000 -60.0000 185 #__ type_ start__ end____ width___ exp.time_ 2 omega -86.00 -29.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -21.2308 137.0000 -87.0000 57 #__ type_ start__ end____ width___ exp.time_ 3 omega -84.00 -58.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -21.2308 179.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 4 omega -6.00 40.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 22.6371 -77.0000 60.0000 46 #__ type_ start__ end____ width___ exp.time_ 5 omega 22.00 83.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 22.6371 -131.0000 -154.0000 61 ; _reflns_number_total 3003 _reflns_number_gt 2596 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _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^)+(0.0420P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(8) _refine_ls_number_reflns 3003 _refine_ls_number_parameters 234 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0762 _refine_ls_wR_factor_gt 0.0733 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.001 _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 Cl1A Cl -0.03295(9) -0.08278(8) -0.86773(5) 0.02600(17) Uani 1 1 d . . . O2A O -0.3221(2) -0.2368(3) -0.63116(13) 0.0212(4) Uani 1 1 d . . . H2AA H -0.377(3) -0.254(4) -0.585(2) 0.017(7) Uiso 1 1 d . . . O3A O 0.1274(2) -0.2054(3) -0.60546(13) 0.0191(4) Uani 1 1 d . . . H3A H 0.164(4) -0.120(4) -0.613(2) 0.017(8) Uiso 1 1 d . . . O1A O -0.0934(2) -0.2384(3) -0.49512(12) 0.0234(4) Uani 1 1 d . . . C1A C -0.1565(3) -0.2286(3) -0.58506(17) 0.0170(5) Uani 1 1 d . . . C2A C -0.0506(3) -0.2004(3) -0.65869(18) 0.0155(5) Uani 1 1 d . . . H2AB H -0.0780 -0.0798 -0.6898 0.019 Uiso 1 1 calc R . . C3A C -0.0876(3) -0.3389(3) -0.74098(18) 0.0159(5) Uani 1 1 d . . . C4A C -0.1148(3) -0.5160(3) -0.7190(2) 0.0203(6) Uani 1 1 d . . . H4A H -0.1186 -0.5473 -0.6534 0.024 Uiso 1 1 calc R . . C5A C -0.1365(4) -0.6479(4) -0.7922(2) 0.0271(7) Uani 1 1 d . . . H5A H -0.1548 -0.7684 -0.7765 0.033 Uiso 1 1 calc R . . C6A C -0.1311(4) -0.6021(4) -0.8880(2) 0.0292(7) Uani 1 1 d . . . H6A H -0.1466 -0.6917 -0.9380 0.035 Uiso 1 1 calc R . . C7A C -0.1037(3) -0.4288(4) -0.91154(19) 0.0244(6) Uani 1 1 d . . . H7A H -0.1001 -0.3980 -0.9773 0.029 Uiso 1 1 calc R . . C8A C -0.0814(3) -0.2994(3) -0.83780(19) 0.0179(6) Uani 1 1 d . . . Cl1 Cl -0.49401(9) -0.47399(9) -0.14323(5) 0.02896(18) Uani 1 1 d . . . O1 O -0.5107(2) -0.2288(3) -0.50356(13) 0.0231(4) Uani 1 1 d . . . O3 O -0.2498(3) -0.3885(3) -0.36002(14) 0.0211(4) Uani 1 1 d . . . H3 H -0.233(4) -0.325(4) -0.396(2) 0.022(9) Uiso 1 1 d . . . O2 O -0.7039(2) -0.3214(2) -0.42696(13) 0.0213(4) Uani 1 1 d . . . H2 H -0.776(4) -0.278(5) -0.483(3) 0.051(11) Uiso 1 1 d . . . C1 C -0.5464(3) -0.2985(3) -0.43268(17) 0.0173(5) Uani 1 1 d . . . C2 C -0.4098(3) -0.3592(3) -0.33978(17) 0.0160(5) Uani 1 1 d . . . H2A H -0.4486 -0.4744 -0.3169 0.019 Uiso 1 1 calc R . . C3 C -0.3966(3) -0.2217(4) -0.25776(18) 0.0166(5) Uani 1 1 d . . . C4 C -0.3506(3) -0.0477(3) -0.27350(19) 0.0209(6) Uani 1 1 d . . . H4 H -0.3262 -0.0180 -0.3347 0.025 Uiso 1 1 calc R . . C5 C -0.3397(3) 0.0829(4) -0.2020(2) 0.0262(7) Uani 1 1 d . . . H5 H -0.3090 0.2014 -0.2143 0.031 Uiso 1 1 calc R . . C6 C -0.3737(3) 0.0405(4) -0.1121(2) 0.0280(7) Uani 1 1 d . . . H6 H -0.3661 0.1302 -0.0628 0.034 Uiso 1 1 calc R . . C7 C -0.4182(4) -0.1308(4) -0.0942(2) 0.0272(7) Uani 1 1 d . . . H7 H -0.4403 -0.1604 -0.0323 0.033 Uiso 1 1 calc R . . C8 C -0.4308(3) -0.2605(3) -0.16757(19) 0.0196(6) Uani 1 1 d . . . 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 Cl1A 0.0392(4) 0.0211(3) 0.0210(3) 0.0052(3) 0.0138(3) 0.0008(3) O2A 0.0154(9) 0.0317(11) 0.0170(9) -0.0010(8) 0.0053(7) 0.0006(8) O3A 0.0171(9) 0.0208(11) 0.0190(9) 0.0025(8) 0.0043(7) -0.0063(9) O1A 0.0219(9) 0.0356(11) 0.0132(9) 0.0014(7) 0.0056(7) -0.0011(9) C1A 0.0191(12) 0.0124(12) 0.0204(13) -0.0003(10) 0.0072(10) 0.0001(10) C2A 0.0155(12) 0.0134(13) 0.0163(12) 0.0001(9) 0.0025(10) -0.0005(10) C3A 0.0126(12) 0.0172(14) 0.0175(13) -0.0010(10) 0.0032(10) 0.0005(10) C4A 0.0203(14) 0.0175(15) 0.0233(14) 0.0012(10) 0.0060(11) 0.0022(10) C5A 0.0285(16) 0.0164(15) 0.0361(17) -0.0051(12) 0.0085(13) -0.0010(12) C6A 0.0278(16) 0.0252(17) 0.0333(16) -0.0131(13) 0.0066(13) 0.0015(13) C7A 0.0243(14) 0.0308(17) 0.0176(13) -0.0047(11) 0.0049(11) 0.0016(12) C8A 0.0178(13) 0.0166(14) 0.0192(13) 0.0023(10) 0.0049(11) 0.0008(11) Cl1 0.0444(4) 0.0235(4) 0.0234(3) 0.0036(3) 0.0167(3) -0.0019(3) O1 0.0174(9) 0.0333(10) 0.0194(9) 0.0069(8) 0.0065(7) 0.0033(8) O3 0.0209(10) 0.0234(11) 0.0209(10) 0.0027(8) 0.0091(8) 0.0066(8) O2 0.0182(10) 0.0288(11) 0.0169(10) 0.0040(7) 0.0046(8) 0.0023(8) C1 0.0207(13) 0.0174(13) 0.0150(12) -0.0032(9) 0.0068(10) 0.0009(10) C2 0.0180(13) 0.0137(13) 0.0159(12) 0.0000(10) 0.0039(10) 0.0018(10) C3 0.0146(12) 0.0147(13) 0.0184(13) -0.0019(10) 0.0012(10) 0.0033(11) C4 0.0192(13) 0.0199(15) 0.0241(14) 0.0015(10) 0.0066(11) 0.0012(11) C5 0.0198(14) 0.0183(15) 0.0368(17) -0.0042(11) 0.0017(12) -0.0014(11) C6 0.0217(14) 0.0280(17) 0.0311(15) -0.0166(14) 0.0020(12) 0.0000(14) C7 0.0266(15) 0.0360(19) 0.0187(14) -0.0067(12) 0.0057(12) 0.0027(13) C8 0.0196(13) 0.0191(15) 0.0190(13) 0.0001(11) 0.0037(10) 0.0007(11) _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 Cl1A C8A 1.747(3) . ? O2A C1A 1.313(3) . ? O2A H2AA 0.88(3) . ? O3A C2A 1.423(3) . ? O3A H3A 0.72(3) . ? O1A C1A 1.214(3) . ? C1A C2A 1.517(3) . ? C2A C3A 1.512(3) . ? C2A H2AB 1.0000 . ? C3A C8A 1.392(3) . ? C3A C4A 1.394(4) . ? C4A C5A 1.394(4) . ? C4A H4A 0.9500 . ? C5A C6A 1.388(4) . ? C5A H5A 0.9500 . ? C6A C7A 1.372(4) . ? C6A H6A 0.9500 . ? C7A C8A 1.386(4) . ? C7A H7A 0.9500 . ? Cl1 C8 1.741(3) . ? O1 C1 1.217(3) . ? O3 C2 1.411(3) . ? O3 H3 0.73(3) . ? O2 C1 1.305(3) . ? O2 H2 0.90(4) . ? C1 C2 1.517(3) . ? C2 C3 1.519(3) . ? C2 H2A 1.0000 . ? C3 C8 1.386(4) . ? C3 C4 1.390(4) . ? C4 C5 1.381(4) . ? C4 H4 0.9500 . ? C5 C6 1.386(4) . ? C5 H5 0.9500 . ? C6 C7 1.376(4) . ? C6 H6 0.9500 . ? C7 C8 1.393(4) . ? C7 H7 0.9500 . ? 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 C1A O2A H2AA 107.4(17) . . ? C2A O3A H3A 107(2) . . ? O1A C1A O2A 125.4(2) . . ? O1A C1A C2A 123.3(2) . . ? O2A C1A C2A 111.3(2) . . ? O3A C2A C3A 109.6(2) . . ? O3A C2A C1A 108.69(19) . . ? C3A C2A C1A 112.6(2) . . ? O3A C2A H2AB 108.6 . . ? C3A C2A H2AB 108.6 . . ? C1A C2A H2AB 108.6 . . ? C8A C3A C4A 117.6(2) . . ? C8A C3A C2A 122.2(2) . . ? C4A C3A C2A 120.0(2) . . ? C5A C4A C3A 120.8(3) . . ? C5A C4A H4A 119.6 . . ? C3A C4A H4A 119.6 . . ? C6A C5A C4A 119.5(3) . . ? C6A C5A H5A 120.2 . . ? C4A C5A H5A 120.2 . . ? C7A C6A C5A 120.8(3) . . ? C7A C6A H6A 119.6 . . ? C5A C6A H6A 119.6 . . ? C6A C7A C8A 118.9(2) . . ? C6A C7A H7A 120.5 . . ? C8A C7A H7A 120.5 . . ? C7A C8A C3A 122.2(2) . . ? C7A C8A Cl1A 117.8(2) . . ? C3A C8A Cl1A 119.8(2) . . ? C2 O3 H3 113(2) . . ? C1 O2 H2 108(2) . . ? O1 C1 O2 123.8(2) . . ? O1 C1 C2 122.6(2) . . ? O2 C1 C2 113.5(2) . . ? O3 C2 C1 111.5(2) . . ? O3 C2 C3 112.1(2) . . ? C1 C2 C3 108.6(2) . . ? O3 C2 H2A 108.2 . . ? C1 C2 H2A 108.2 . . ? C3 C2 H2A 108.2 . . ? C8 C3 C4 117.9(2) . . ? C8 C3 C2 123.0(2) . . ? C4 C3 C2 119.1(2) . . ? C5 C4 C3 121.3(3) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 119.3(3) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C3 C8 C7 121.5(2) . . ? C3 C8 Cl1 120.72(19) . . ? C7 C8 Cl1 117.8(2) . . ? 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 O2A H2AA O1 0.88(3) 1.77(3) 2.635(3) 164(3) . O3A H3A O3 0.72(3) 1.94(3) 2.666(3) 176(3) 2_554 O3 H3 O1A 0.73(3) 2.11(3) 2.772(3) 152(3) . O2 H2 O3A 0.90(4) 1.75(4) 2.626(3) 166(3) 1_455 O2 H2 O1A 0.90(4) 2.54(3) 3.083(3) 120(3) 1_455 _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.306 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.054