# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef 'GABAETOH.txt' _audit_creation_date 6-August-2010 _audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' _publ_contact_author_name 'Elise J. C. de Vries' _publ_contact_author_fax '0027-11-717 6749' _publ_contact_author_phone '0027-11-717 6723' _publ_contact_author_address ; Molecular Science Institute School of Chemistry University of the Witwatersrand PO WITS, 2050 Johannesburg South Africa ; _publ_contact_author_email elise.devries@wits.ac.za loop_ _publ_author_name 'Elise J. C. de Vries' 'Demetrius Levendis' data_C:\GABAETOH.CIF _database_code_depnum_ccdc_archive 'CCDC 788752' #TrackingRef 'GABAETOH.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; solvated gamma-aminobutyric acid ; _chemical_name_common 'solvated gamma-aminobutyric acid' _chemical_melting_point ? _chemical_formula_moiety '2(C4 H9 N O2) C0.20 O0.10' _chemical_formula_sum 'C8.20 H18 N2 O4.10' _chemical_formula_weight 210.25 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' N N 0.0061 0.0033 '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 hexagonal _symmetry_space_group_name_H-M P62 _symmetry_space_group_name_Hall P62 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+1/3' '-y, x-y, z+2/3' '-x, -y, z' '-x+y, -x, z+1/3' 'y, -x+y, z+2/3' _cell_length_a 15.9164(8) _cell_length_b 15.9164(8) _cell_length_c 7.8769(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1728.13(15) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9533 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15431 _diffrn_reflns_av_R_equivalents 0.0843 _diffrn_reflns_av_sigmaI/netI 0.0768 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.10 _reflns_number_total 2534 _reflns_number_gt 1666 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-SEED (Barbour, 2001; Atwood & Barbour, 2003)' _computing_publication_material 'X-SEED (Barbour, 2001; Atwood & Barbour, 2003)' _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^)+(0.0653P)^2^+0.1143P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(17) _refine_ls_number_reflns 2534 _refine_ls_number_parameters 142 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1396 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.012 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 O1A O 0.33137(14) 0.31579(15) 0.3690(3) 0.0369(5) Uani 1 1 d . . . N1A N 0.32140(17) 0.28343(17) 1.0073(3) 0.0315(6) Uani 1 1 d . . . H1A H 0.3150 0.2235 0.9975 0.047 Uiso 1 1 calc R . . H1C H 0.3089 0.2929 1.1162 0.047 Uiso 1 1 calc R . . H1B H 0.3830 0.3294 0.9791 0.047 Uiso 1 1 calc R . . C1A C 0.2493(2) 0.3043(2) 0.3994(4) 0.0318(7) Uani 1 1 d . . . O2A O 0.19174(17) 0.29714(18) 0.2856(3) 0.0520(7) Uani 1 1 d . . . C2A C 0.2180(2) 0.3003(2) 0.5835(4) 0.0363(7) Uani 1 1 d . . . H2A H 0.2121 0.3583 0.6070 0.044 Uiso 1 1 calc R . . H2B H 0.1530 0.2425 0.5984 0.044 Uiso 1 1 calc R . . C3A C 0.2854(2) 0.2962(2) 0.7106(3) 0.0323(7) Uani 1 1 d . . . H3A H 0.3503 0.3546 0.6974 0.039 Uiso 1 1 calc R . . H3B H 0.2921 0.2388 0.6865 0.039 Uiso 1 1 calc R . . C4A C 0.2524(2) 0.2907(2) 0.8926(4) 0.0308(7) Uani 1 1 d . . . H4A H 0.2487 0.3494 0.9204 0.037 Uiso 1 1 calc R . . H4B H 0.1870 0.2334 0.9072 0.037 Uiso 1 1 calc R . . O1B O 0.66651(15) 0.46646(16) -0.1931(2) 0.0403(6) Uani 1 1 d . . . N1B N 0.50464(17) 0.35116(17) 0.5235(3) 0.0307(6) Uani 1 1 d . . . H1E H 0.4452 0.3407 0.4918 0.046 Uiso 1 1 calc R . . H1F H 0.5172 0.3737 0.6321 0.046 Uiso 1 1 calc R . . H1D H 0.5055 0.2945 0.5171 0.046 Uiso 1 1 calc R . . C1B C 0.5993(2) 0.4362(2) -0.0858(4) 0.0310(7) Uani 1 1 d . . . O2B O 0.51114(15) 0.39066(17) -0.1227(3) 0.0416(6) Uani 1 1 d . . . C2B C 0.6285(2) 0.4566(2) 0.1003(4) 0.0393(8) Uani 1 1 d . . . H2D H 0.6840 0.4460 0.1198 0.047 Uiso 1 1 calc R . . H2E H 0.6513 0.5259 0.1232 0.047 Uiso 1 1 calc R . . C3B C 0.5504(2) 0.3966(2) 0.2255(4) 0.0331(7) Uani 1 1 d . . . H3D H 0.5312 0.3275 0.2095 0.040 Uiso 1 1 calc R . . H3E H 0.4930 0.4032 0.2014 0.040 Uiso 1 1 calc R . . C4B C 0.5800(2) 0.4241(2) 0.4083(4) 0.0341(7) Uani 1 1 d . . . H4D H 0.6428 0.4274 0.4295 0.041 Uiso 1 1 calc R . . H4E H 0.5882 0.4889 0.4312 0.041 Uiso 1 1 calc R . . O1X O 0.012(3) -0.042(3) 0.509(5) 0.108(12) Uiso 0.10 1 d PD A -1 C1X C 0.023(3) -0.017(3) 0.686(5) 0.080(15) Uiso 0.10 1 d PD A -1 C2X C 0.109(2) 0.049(2) 0.799(4) 0.034(7) Uiso 0.10 1 d PD A -1 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 O1A 0.0352(12) 0.0629(14) 0.0206(10) -0.0027(10) 0.0016(9) 0.0305(11) N1A 0.0450(15) 0.0371(13) 0.0164(13) 0.0005(11) 0.0014(11) 0.0234(12) C1A 0.0390(18) 0.0447(18) 0.0173(16) -0.0027(14) -0.0018(13) 0.0250(15) O2A 0.0489(14) 0.100(2) 0.0205(12) -0.0036(13) -0.0053(11) 0.0469(14) C2A 0.0395(17) 0.056(2) 0.0223(16) -0.0004(15) 0.0031(14) 0.0306(16) C3A 0.0400(17) 0.0460(18) 0.0183(15) 0.0009(14) 0.0027(14) 0.0269(15) C4A 0.0368(16) 0.0348(17) 0.0245(17) -0.0004(13) 0.0020(13) 0.0208(14) O1B 0.0381(12) 0.0593(15) 0.0214(12) 0.0011(11) 0.0037(10) 0.0229(11) N1B 0.0382(14) 0.0422(14) 0.0167(12) -0.0023(12) -0.0019(11) 0.0239(12) C1B 0.0408(19) 0.0367(16) 0.0168(15) -0.0008(14) -0.0017(14) 0.0203(15) O2B 0.0325(12) 0.0642(15) 0.0215(11) -0.0026(11) -0.0017(9) 0.0193(11) C2B 0.0384(17) 0.0492(19) 0.0208(17) -0.0024(14) -0.0009(14) 0.0147(15) C3B 0.0410(16) 0.0376(17) 0.0191(17) -0.0006(13) 0.0017(13) 0.0185(14) C4B 0.0364(18) 0.0391(17) 0.0222(17) 0.0002(14) -0.0025(14) 0.0154(14) _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 O1A C1A 1.248(4) . ? N1A C4A 1.470(4) . ? N1A H1A 0.9100 . ? N1A H1C 0.9100 . ? N1A H1B 0.9100 . ? C1A O2A 1.246(4) . ? C1A C2A 1.524(4) . ? C2A C3A 1.493(4) . ? C2A H2A 0.9900 . ? C2A H2B 0.9900 . ? C3A C4A 1.514(4) . ? C3A H3A 0.9900 . ? C3A H3B 0.9900 . ? C4A H4A 0.9900 . ? C4A H4B 0.9900 . ? O1B C1B 1.255(3) . ? N1B C4B 1.489(4) . ? N1B H1E 0.9100 . ? N1B H1F 0.9100 . ? N1B H1D 0.9100 . ? C1B O2B 1.249(4) . ? C1B C2B 1.523(4) . ? C2B C3B 1.497(4) . ? C2B H2D 0.9900 . ? C2B H2E 0.9900 . ? C3B C4B 1.510(4) . ? C3B H3D 0.9900 . ? C3B H3E 0.9900 . ? C4B H4D 0.9900 . ? C4B H4E 0.9900 . ? O1X C1X 1.44(2) . ? C1X C2X 1.53(2) . ? 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 C4A N1A H1A 109.5 . . ? C4A N1A H1C 109.5 . . ? H1A N1A H1C 109.5 . . ? C4A N1A H1B 109.5 . . ? H1A N1A H1B 109.5 . . ? H1C N1A H1B 109.5 . . ? O2A C1A O1A 122.9(3) . . ? O2A C1A C2A 118.1(3) . . ? O1A C1A C2A 119.0(3) . . ? C3A C2A C1A 114.4(2) . . ? C3A C2A H2A 108.7 . . ? C1A C2A H2A 108.6 . . ? C3A C2A H2B 108.6 . . ? C1A C2A H2B 108.7 . . ? H2A C2A H2B 107.6 . . ? C2A C3A C4A 113.7(2) . . ? C2A C3A H3A 108.8 . . ? C4A C3A H3A 108.8 . . ? C2A C3A H3B 108.8 . . ? C4A C3A H3B 108.8 . . ? H3A C3A H3B 107.7 . . ? N1A C4A C3A 109.6(2) . . ? N1A C4A H4A 109.8 . . ? C3A C4A H4A 109.8 . . ? N1A C4A H4B 109.8 . . ? C3A C4A H4B 109.7 . . ? H4A C4A H4B 108.2 . . ? C4B N1B H1E 109.5 . . ? C4B N1B H1F 109.5 . . ? H1E N1B H1F 109.5 . . ? C4B N1B H1D 109.5 . . ? H1E N1B H1D 109.5 . . ? H1F N1B H1D 109.5 . . ? O2B C1B O1B 124.1(3) . . ? O2B C1B C2B 118.8(3) . . ? O1B C1B C2B 117.1(3) . . ? C3B C2B C1B 115.5(3) . . ? C3B C2B H2D 108.4 . . ? C1B C2B H2D 108.4 . . ? C3B C2B H2E 108.4 . . ? C1B C2B H2E 108.4 . . ? H2D C2B H2E 107.5 . . ? C2B C3B C4B 113.8(2) . . ? C2B C3B H3D 108.8 . . ? C4B C3B H3D 108.8 . . ? C2B C3B H3E 108.8 . . ? C4B C3B H3E 108.8 . . ? H3D C3B H3E 107.7 . . ? N1B C4B C3B 110.0(2) . . ? N1B C4B H4D 109.7 . . ? C3B C4B H4D 109.7 . . ? N1B C4B H4E 109.6 . . ? C3B C4B H4E 109.7 . . ? H4D C4B H4E 108.2 . . ? O1X C1X C2X 135(4) . . ? 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 O2A C1A C2A C3A 172.3(3) . . . . ? O1A C1A C2A C3A -8.6(4) . . . . ? C1A C2A C3A C4A -179.1(3) . . . . ? C2A C3A C4A N1A 177.9(2) . . . . ? O2B C1B C2B C3B 16.8(5) . . . . ? O1B C1B C2B C3B -163.0(3) . . . . ? C1B C2B C3B C4B -175.7(3) . . . . ? C2B C3B C4B N1B -170.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.231 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.048