# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Maria Duarte' 'V\^ania Andre' 'Dario Braga' 'Roberto Brescello' 'Livius Cotarca' 'Fabrizia Grepioni' 'Lucia Maini' "Maria de F\'atima M. Piedade" 'Marco Polito' 'Katia Rubini' _publ_contact_author_name 'Prof Maria Duarte' _publ_contact_author_email TERESA.DUARTE@IST.UTL.PT _publ_section_title ; Polymorphic gabapentin: thermal behaviour, reactivity and interconversion of forms in solution and in the solid state. ; # Attachment 'Cocrystal GBPL_BA_150K.cif' data_GabapentinLactam_Benzoic_Acid_cocrystal _database_code_depnum_ccdc_archive 'CCDC 697246' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common GBPL_BenzoicAcid_cocrystal _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H21 N O3' _chemical_formula_weight 275.34 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 Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.5410(4) _cell_length_b 19.2190(5) _cell_length_c 12.0700(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.601(7) _cell_angle_gamma 90.00 _cell_volume 1504.01(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.37 _cell_measurement_theta_max 26.40 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.084 _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 150(2) _diffrn_radiation_wavelength 0.71069 _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 11010 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 26.40 _reflns_number_total 3026 _reflns_number_gt 1772 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution SIR97 _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^)+(0.0471P)^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_number_reflns 3026 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0977 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1031 _refine_ls_wR_factor_gt 0.0915 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _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 O1 O 0.90008(19) 0.94726(6) 0.88686(10) 0.0463(4) Uani 1 1 d . . . C1 C 0.4860(2) 1.06366(8) 0.78037(13) 0.0297(4) Uani 1 1 d . . . C2 C 0.5799(4) 1.11319(10) 0.70082(15) 0.0410(5) Uani 1 1 d . . . C3 C 0.5107(4) 1.09658(12) 0.57809(16) 0.0513(6) Uani 1 1 d . . . C4 C 0.2780(4) 1.09626(14) 0.5547(2) 0.0673(7) Uani 1 1 d . . . C5 C 0.1827(4) 1.04575(15) 0.62993(19) 0.0612(7) Uani 1 1 d . . . C6 C 0.2523(3) 1.06246(14) 0.75277(18) 0.0474(5) Uani 1 1 d . . . C7 C 0.5851(3) 0.99121(10) 0.77741(16) 0.0351(5) Uani 1 1 d . . . C8 C 0.7587(3) 0.99123(9) 0.87110(14) 0.0332(4) Uani 1 1 d . . . C9 C 0.5528(3) 1.08546(10) 0.90283(15) 0.0332(4) Uani 1 1 d . . . N1 N 0.7382(2) 1.04480(7) 0.93711(13) 0.0342(4) Uani 1 1 d . . . O2 O 1.28408(18) 0.85949(6) 0.85189(10) 0.0428(4) Uani 1 1 d . . . O3 O 0.98803(19) 0.86061(7) 0.73775(11) 0.0454(4) Uani 1 1 d . . . C10 C 1.2652(2) 0.79854(8) 0.67944(13) 0.0278(4) Uani 1 1 d . . . C11 C 1.1410(3) 0.77369(10) 0.58662(15) 0.0422(5) Uani 1 1 d . . . C12 C 1.2251(4) 0.73051(11) 0.51177(18) 0.0578(6) Uani 1 1 d . . . C13 C 1.4313(4) 0.71455(11) 0.5279(2) 0.0586(7) Uani 1 1 d . . . C14 C 1.5554(4) 0.74101(12) 0.61852(19) 0.0577(6) Uani 1 1 d . . . C15 C 1.4737(3) 0.78244(11) 0.69432(16) 0.0440(5) Uani 1 1 d . . . C16 C 1.1829(3) 0.84215(8) 0.76441(14) 0.0305(4) Uani 1 1 d . . . H101 H 0.830(3) 1.0534(9) 1.0008(16) 0.041(5) Uiso 1 1 d . . . H2A H 0.735(3) 1.1119(9) 0.7161(15) 0.052(6) Uiso 1 1 d . . . H2B H 0.534(2) 1.1603(10) 0.7132(14) 0.042(5) Uiso 1 1 d . . . H3A H 0.560(2) 1.0486(9) 0.5590(14) 0.042(5) Uiso 1 1 d . . . H3B H 0.572(3) 1.1313(11) 0.5315(18) 0.070(7) Uiso 1 1 d . . . H4A H 0.238(3) 1.0850(11) 0.481(2) 0.072(7) Uiso 1 1 d . . . H4B H 0.222(3) 1.1468(12) 0.5665(17) 0.075(7) Uiso 1 1 d . . . H5A H 0.229(3) 0.9978(11) 0.6163(16) 0.053(6) Uiso 1 1 d . . . H5B H 0.035(4) 1.0454(11) 0.616(2) 0.088(8) Uiso 1 1 d . . . H6A H 0.196(3) 1.0319(9) 0.8008(15) 0.041(6) Uiso 1 1 d . . . H6B H 0.199(3) 1.1098(10) 0.7688(15) 0.051(6) Uiso 1 1 d . . . H7A H 0.633(2) 0.9810(9) 0.7125(15) 0.039(5) Uiso 1 1 d . . . H7B H 0.491(3) 0.9553(10) 0.7941(15) 0.053(6) Uiso 1 1 d . . . H9A H 0.580(2) 1.1355(9) 0.9105(13) 0.039(5) Uiso 1 1 d . . . H9B H 0.448(2) 1.0753(8) 0.9507(13) 0.029(4) Uiso 1 1 d . . . H201 H 0.953(4) 0.8945(13) 0.791(2) 0.091(8) Uiso 1 1 d . . . H11 H 0.992(3) 0.7863(10) 0.5776(16) 0.067(7) Uiso 1 1 d . . . H12 H 1.127(3) 0.7157(10) 0.4526(18) 0.069(7) Uiso 1 1 d . . . H13 H 1.485(3) 0.6840(11) 0.4714(19) 0.081(7) Uiso 1 1 d . . . H14 H 1.714(4) 0.7305(12) 0.6334(19) 0.094(8) Uiso 1 1 d . . . H15 H 1.562(3) 0.8018(11) 0.7605(19) 0.072(7) Uiso 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 O1 0.0521(9) 0.0441(8) 0.0423(8) -0.0003(6) 0.0050(6) 0.0208(7) C1 0.0300(10) 0.0286(9) 0.0308(10) 0.0009(7) 0.0053(8) 0.0012(7) C2 0.0555(14) 0.0319(12) 0.0362(11) 0.0019(9) 0.0078(10) -0.0039(10) C3 0.0787(18) 0.0420(13) 0.0329(11) 0.0055(10) 0.0061(11) -0.0008(12) C4 0.094(2) 0.0657(16) 0.0361(14) -0.0059(12) -0.0142(13) 0.0242(15) C5 0.0383(14) 0.0828(19) 0.0585(16) -0.0207(14) -0.0079(11) 0.0071(13) C6 0.0322(12) 0.0629(15) 0.0466(13) -0.0083(12) 0.0039(10) 0.0029(11) C7 0.0416(12) 0.0319(11) 0.0324(11) -0.0017(8) 0.0075(9) 0.0004(9) C8 0.0393(11) 0.0304(10) 0.0310(10) 0.0055(8) 0.0090(8) 0.0052(9) C9 0.0340(11) 0.0332(11) 0.0333(10) 0.0012(8) 0.0078(9) 0.0067(8) N1 0.0366(9) 0.0353(9) 0.0302(9) 0.0006(7) 0.0030(7) 0.0082(7) O2 0.0402(8) 0.0574(8) 0.0294(7) -0.0100(6) -0.0002(6) -0.0033(6) O3 0.0366(8) 0.0566(9) 0.0411(8) -0.0089(7) -0.0018(6) 0.0148(6) C10 0.0327(10) 0.0253(9) 0.0252(9) 0.0034(7) 0.0033(7) -0.0014(7) C11 0.0411(12) 0.0523(12) 0.0330(11) -0.0061(9) 0.0036(9) -0.0125(10) C12 0.0800(19) 0.0569(14) 0.0373(12) -0.0165(11) 0.0109(12) -0.0301(13) C13 0.090(2) 0.0360(13) 0.0585(15) -0.0039(11) 0.0417(15) -0.0017(12) C14 0.0628(16) 0.0629(15) 0.0515(14) 0.0082(12) 0.0233(12) 0.0237(12) C15 0.0420(12) 0.0578(13) 0.0328(11) 0.0030(10) 0.0071(9) 0.0094(10) C16 0.0325(11) 0.0298(9) 0.0289(10) 0.0017(8) 0.0029(8) -0.0041(8) _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 C8 1.2486(19) . ? C1 C6 1.521(3) . ? C1 C2 1.537(2) . ? C1 C7 1.538(2) . ? C1 C9 1.543(2) . ? C2 C3 1.524(3) . ? C2 H2A 1.007(19) . ? C2 H2B 0.973(18) . ? C3 C4 1.511(3) . ? C3 H3A 1.014(18) . ? C3 H3B 0.99(2) . ? C4 C5 1.518(3) . ? C4 H4A 0.92(2) . ? C4 H4B 1.05(2) . ? C5 C6 1.526(3) . ? C5 H5A 0.99(2) . ? C5 H5B 0.96(3) . ? C6 H6A 0.934(18) . ? C6 H6B 1.002(19) . ? C7 C8 1.493(2) . ? C7 H7A 0.903(18) . ? C7 H7B 0.96(2) . ? C8 N1 1.320(2) . ? C9 N1 1.456(2) . ? C9 H9A 0.980(17) . ? C9 H9B 0.971(17) . ? N1 H101 0.928(18) . ? O2 C16 1.2162(19) . ? O3 C16 1.3213(19) . ? O3 H201 0.97(3) . ? C10 C11 1.379(2) . ? C10 C15 1.386(2) . ? C10 C16 1.480(2) . ? C11 C12 1.393(3) . ? C11 H11 1.00(2) . ? C12 C13 1.372(3) . ? C12 H12 0.94(2) . ? C13 C14 1.371(3) . ? C13 H13 1.00(2) . ? C14 C15 1.373(3) . ? C14 H14 1.05(2) . ? C15 H15 0.99(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 C6 C1 C2 110.24(16) . . ? C6 C1 C7 113.29(16) . . ? C2 C1 C7 109.98(15) . . ? C6 C1 C9 111.29(15) . . ? C2 C1 C9 110.14(14) . . ? C7 C1 C9 101.61(13) . . ? C3 C2 C1 112.69(16) . . ? C3 C2 H2A 109.6(11) . . ? C1 C2 H2A 110.3(10) . . ? C3 C2 H2B 106.6(10) . . ? C1 C2 H2B 108.8(10) . . ? H2A C2 H2B 108.8(15) . . ? C4 C3 C2 110.1(2) . . ? C4 C3 H3A 107.4(10) . . ? C2 C3 H3A 110.4(10) . . ? C4 C3 H3B 111.6(12) . . ? C2 C3 H3B 108.7(12) . . ? H3A C3 H3B 108.6(16) . . ? C3 C4 C5 111.98(19) . . ? C3 C4 H4A 109.5(14) . . ? C5 C4 H4A 109.8(14) . . ? C3 C4 H4B 109.1(11) . . ? C5 C4 H4B 109.5(12) . . ? H4A C4 H4B 106.8(18) . . ? C4 C5 C6 110.7(2) . . ? C4 C5 H5A 109.7(11) . . ? C6 C5 H5A 107.4(12) . . ? C4 C5 H5B 112.5(14) . . ? C6 C5 H5B 109.7(15) . . ? H5A C5 H5B 106.7(18) . . ? C1 C6 C5 112.21(18) . . ? C1 C6 H6A 110.0(11) . . ? C5 C6 H6A 112.2(11) . . ? C1 C6 H6B 108.0(10) . . ? C5 C6 H6B 108.1(11) . . ? H6A C6 H6B 106.0(15) . . ? C8 C7 C1 105.24(14) . . ? C8 C7 H7A 109.9(11) . . ? C1 C7 H7A 114.3(11) . . ? C8 C7 H7B 106.6(11) . . ? C1 C7 H7B 111.0(11) . . ? H7A C7 H7B 109.4(15) . . ? O1 C8 N1 124.65(16) . . ? O1 C8 C7 126.10(15) . . ? N1 C8 C7 109.24(15) . . ? N1 C9 C1 104.26(14) . . ? N1 C9 H9A 111.6(10) . . ? C1 C9 H9A 112.4(10) . . ? N1 C9 H9B 110.3(9) . . ? C1 C9 H9B 112.5(9) . . ? H9A C9 H9B 105.9(13) . . ? C8 N1 C9 113.25(15) . . ? C8 N1 H101 122.3(11) . . ? C9 N1 H101 124.4(11) . . ? C16 O3 H201 109.1(14) . . ? C11 C10 C15 119.44(17) . . ? C11 C10 C16 121.99(16) . . ? C15 C10 C16 118.58(15) . . ? C10 C11 C12 119.5(2) . . ? C10 C11 H11 117.9(11) . . ? C12 C11 H11 122.6(11) . . ? C13 C12 C11 120.5(2) . . ? C13 C12 H12 126.8(13) . . ? C11 C12 H12 112.8(13) . . ? C14 C13 C12 119.8(2) . . ? C14 C13 H13 122.6(13) . . ? C12 C13 H13 117.6(13) . . ? C13 C14 C15 120.3(2) . . ? C13 C14 H14 122.2(13) . . ? C15 C14 H14 117.4(13) . . ? C14 C15 C10 120.4(2) . . ? C14 C15 H15 121.2(12) . . ? C10 C15 H15 118.4(12) . . ? O2 C16 O3 122.30(16) . . ? O2 C16 C10 123.42(16) . . ? O3 C16 C10 114.27(15) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.170 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.036 # Attachment 'Form IV_RT.cif' data_gabapentin_Form_IV_RT _database_code_depnum_ccdc_archive 'CCDC 697247' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Gabapentin _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H17 N O2' _chemical_formula_weight 171.24 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 Monoclinic _symmetry_space_group_name_H-M P21/c 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 14.7361(17) _cell_length_b 6.6656(12) _cell_length_c 9.890(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.090(6) _cell_angle_gamma 90.00 _cell_volume 933.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.38 _cell_measurement_theta_max 25.68 _exptl_crystal_description parallelepipedic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.085 _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 '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 4022 _diffrn_reflns_av_R_equivalents 0.0782 _diffrn_reflns_av_sigmaI/netI 0.1994 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 25.68 _reflns_number_total 1750 _reflns_number_gt 873 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker Saint' _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury and Ortep' _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. The distances between the nitrogen and the 3 hydrogen atoms bonded to it were restrained to a fixed value because as these H atoms are involved in hydrogen-bonds, the distance NH was larger than expected, displaying alerts B and C on the checkcif. ; _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^)+(0.0000P)^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 SHELXL _refine_ls_extinction_coef 0.044(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1750 _refine_ls_number_parameters 122 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1430 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1923 _refine_ls_wR_factor_gt 0.1530 _refine_ls_goodness_of_fit_ref 0.806 _refine_ls_restrained_S_all 0.808 _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 0.01969(15) 0.2124(3) 0.4149(2) 0.0486(7) Uani 1 1 d . . . O2 O 0.13663(19) 0.4336(4) 0.4493(3) 0.0836(11) Uani 1 1 d . . . C1 C 0.2290(2) -0.0010(4) 0.4833(3) 0.0327(8) Uani 1 1 d . . . C2 C 0.3055(2) 0.1319(5) 0.4489(3) 0.0433(9) Uani 1 1 d . . . H2A H 0.3336 0.0587 0.3859 0.052 Uiso 1 1 calc R . . H2B H 0.2756 0.2507 0.3995 0.052 Uiso 1 1 calc R . . C3 C 0.3838(2) 0.1970(6) 0.5775(4) 0.0575(11) Uani 1 1 d . . . H3A H 0.3578 0.2882 0.6336 0.069 Uiso 1 1 calc R . . H3B H 0.4318 0.2688 0.5469 0.069 Uiso 1 1 calc R . . C4 C 0.4292(2) 0.0182(6) 0.6684(4) 0.0649(12) Uani 1 1 d . . . H4B H 0.4644 -0.0614 0.6181 0.078 Uiso 1 1 calc R . . H4A H 0.4731 0.0666 0.7544 0.078 Uiso 1 1 calc R . . C5 C 0.3546(2) -0.1120(5) 0.7048(3) 0.0490(10) Uani 1 1 d . . . H5A H 0.3844 -0.2299 0.7556 0.059 Uiso 1 1 calc R . . H5B H 0.3252 -0.0376 0.7658 0.059 Uiso 1 1 calc R . . C6 C 0.2795(2) -0.1766(5) 0.5738(3) 0.0396(9) Uani 1 1 d . . . H6B H 0.2329 -0.2575 0.6015 0.047 Uiso 1 1 calc R . . H6A H 0.3086 -0.2603 0.5172 0.047 Uiso 1 1 calc R . . C7 C 0.1702(2) 0.1185(4) 0.5630(3) 0.0361(8) Uani 1 1 d . . . H7A H 0.1337 0.0253 0.6021 0.043 Uiso 1 1 calc R . . H7B H 0.2127 0.1896 0.6407 0.043 Uiso 1 1 calc R . . C8 C 0.1036(2) 0.2683(5) 0.4703(3) 0.0410(9) Uani 1 1 d . . . C9 C 0.1654(2) -0.0779(5) 0.3431(3) 0.0384(9) Uani 1 1 d . . . H9A H 0.1448 0.0358 0.2810 0.046 Uiso 1 1 calc R . . H9C H 0.2026 -0.1643 0.3002 0.046 Uiso 1 1 calc R . . N1 N 0.08060(19) -0.1908(4) 0.3533(3) 0.0371(7) Uani 1 1 d D . . H103 H 0.040(2) -0.212(5) 0.261(3) 0.051(10) Uiso 1 1 d D . . H101 H 0.100(2) -0.326(5) 0.400(4) 0.086(14) Uiso 1 1 d D . . H102 H 0.047(3) -0.100(7) 0.402(5) 0.121(18) Uiso 1 1 d 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 O1 0.0477(15) 0.0435(16) 0.0463(13) 0.0044(11) -0.0009(11) 0.0037(11) O2 0.0744(19) 0.0278(16) 0.139(3) 0.0167(17) 0.0138(19) -0.0007(14) C1 0.0432(18) 0.0257(18) 0.0289(15) -0.0029(14) 0.0096(14) -0.0041(14) C2 0.050(2) 0.041(2) 0.0407(17) 0.0076(16) 0.0165(16) -0.0050(16) C3 0.050(2) 0.060(3) 0.059(2) 0.010(2) 0.0096(18) -0.0197(19) C4 0.048(2) 0.071(3) 0.068(2) 0.014(2) 0.002(2) -0.005(2) C5 0.045(2) 0.050(2) 0.0465(19) 0.0132(17) 0.0032(16) 0.0055(17) C6 0.049(2) 0.032(2) 0.0390(17) 0.0024(16) 0.0135(15) -0.0003(15) C7 0.0437(18) 0.0323(19) 0.0294(15) -0.0006(15) 0.0049(13) 0.0041(15) C8 0.049(2) 0.030(2) 0.0403(18) -0.0033(16) 0.0061(16) 0.0017(16) C9 0.047(2) 0.0345(19) 0.0340(16) -0.0033(15) 0.0119(15) -0.0001(15) N1 0.0419(16) 0.0290(17) 0.0355(15) -0.0047(14) 0.0025(13) -0.0040(13) _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 C8 1.262(4) . ? O2 C8 1.245(4) . ? C1 C9 1.531(4) . ? C1 C6 1.535(4) . ? C1 C2 1.544(4) . ? C1 C7 1.545(4) . ? C2 C3 1.524(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.531(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.520(5) . ? C4 H4B 0.9700 . ? C4 H4A 0.9700 . ? C5 C6 1.515(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6B 0.9700 . ? C6 H6A 0.9700 . ? C7 C8 1.517(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 N1 1.485(4) . ? C9 H9A 0.9700 . ? C9 H9C 0.9700 . ? N1 H103 0.95(3) . ? N1 H101 1.02(3) . ? N1 H102 0.98(4) . ? 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 C9 C1 C6 110.4(2) . . ? C9 C1 C2 107.1(2) . . ? C6 C1 C2 107.5(2) . . ? C9 C1 C7 110.2(2) . . ? C6 C1 C7 110.2(2) . . ? C2 C1 C7 111.4(3) . . ? C3 C2 C1 114.2(2) . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C2 C3 C4 112.0(3) . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 110.9(3) . . ? C5 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? H4B C4 H4A 108.1 . . ? C6 C5 C4 111.4(3) . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C5 C6 C1 113.8(3) . . ? C5 C6 H6B 108.8 . . ? C1 C6 H6B 108.8 . . ? C5 C6 H6A 108.8 . . ? C1 C6 H6A 108.8 . . ? H6B C6 H6A 107.7 . . ? C8 C7 C1 113.0(2) . . ? C8 C7 H7A 109.0 . . ? C1 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C1 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? O2 C8 O1 124.8(3) . . ? O2 C8 C7 117.8(3) . . ? O1 C8 C7 117.4(3) . . ? N1 C9 C1 115.1(2) . . ? N1 C9 H9A 108.5 . . ? C1 C9 H9A 108.5 . . ? N1 C9 H9C 108.5 . . ? C1 C9 H9C 108.5 . . ? H9A C9 H9C 107.5 . . ? C9 N1 H103 108.6(19) . . ? C9 N1 H101 110(2) . . ? H103 N1 H101 109(3) . . ? C9 N1 H102 105(3) . . ? H103 N1 H102 107(3) . . ? H101 N1 H102 116(4) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.200 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.050 # Attachment 'Form_III_RT.cif' data_gabapentin_Form_III_RT _database_code_depnum_ccdc_archive 'CCDC 697248' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Gabapentin _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H17 N O2' _chemical_formula_weight 171.24 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.582(9) _cell_length_b 5.932(3) _cell_length_c 10.915(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.31(2) _cell_angle_gamma 90.00 _cell_volume 1879.9(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.085 _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 1740 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 24.95 _reflns_number_total 1642 _reflns_number_gt 1285 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0849P)^2^+0.6689P] 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 SHELXL _refine_ls_extinction_coef 0.017(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1642 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1362 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 H101 H 0.2685(8) 0.276(4) 0.739(2) 0.057(6) Uiso 1 1 d . . . H102 H 0.2874(8) 0.343(4) 0.880(2) 0.061(7) Uiso 1 1 d . . . H103 H 0.2979(7) 0.119(4) 0.841(2) 0.045(5) Uiso 1 1 d . . . C1 C 0.36194(6) 0.2177(3) 0.72176(16) 0.0320(4) Uani 1 1 d . . . C2 C 0.38738(6) 0.0241(3) 0.81026(18) 0.0391(5) Uani 1 1 d . . . H2A H 0.3655 -0.0566 0.8419 0.047 Uiso 1 1 calc R . . H2B H 0.3989 -0.0807 0.7595 0.047 Uiso 1 1 calc R . . C3 C 0.42756(7) 0.1018(4) 0.9256(2) 0.0537(6) Uani 1 1 d . . . H3A H 0.4159 0.1917 0.9827 0.064 Uiso 1 1 calc R . . H3B H 0.4431 -0.0287 0.9734 0.064 Uiso 1 1 calc R . . C4 C 0.46167(7) 0.2403(4) 0.8820(3) 0.0660(7) Uani 1 1 d . . . H4A H 0.4757 0.1460 0.8322 0.079 Uiso 1 1 calc R . . H4B H 0.4859 0.2948 0.9569 0.079 Uiso 1 1 calc R . . C5 C 0.43791(7) 0.4392(4) 0.8003(2) 0.0584(6) Uani 1 1 d . . . H5A H 0.4600 0.5205 0.7697 0.070 Uiso 1 1 calc R . . H5B H 0.4266 0.5414 0.8529 0.070 Uiso 1 1 calc R . . C6 C 0.39773(6) 0.3614(3) 0.68490(19) 0.0442(5) Uani 1 1 d . . . H6A H 0.4098 0.2745 0.6275 0.053 Uiso 1 1 calc R . . H6B H 0.3825 0.4931 0.6378 0.053 Uiso 1 1 calc R . . C7 C 0.32848(6) 0.1095(3) 0.59980(16) 0.0341(5) Uani 1 1 d . . . H7A H 0.3459 0.0032 0.5660 0.041 Uiso 1 1 calc R . . H7B H 0.3060 0.0230 0.6261 0.041 Uiso 1 1 calc R . . C8 C 0.30225(6) 0.2630(3) 0.48958(16) 0.0317(4) Uani 1 1 d . . . C9 C 0.33694(6) 0.3712(3) 0.79154(17) 0.0345(4) Uani 1 1 d . . . H9A H 0.3584 0.4118 0.8749 0.041 Uiso 1 1 calc R . . H9B H 0.3281 0.5089 0.7420 0.041 Uiso 1 1 calc R . . N1 N 0.29513(5) 0.2710(3) 0.81191(16) 0.0344(4) Uani 1 1 d . . . O1 O 0.29102(4) 0.1805(2) 0.37730(11) 0.0388(4) Uani 1 1 d . . . O2 O 0.29285(4) 0.4599(2) 0.51368(12) 0.0423(4) 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 C1 0.0362(9) 0.0248(8) 0.0332(9) 0.0031(7) 0.0084(7) 0.0049(7) C2 0.0438(10) 0.0301(10) 0.0409(10) 0.0064(8) 0.0098(8) 0.0088(8) C3 0.0511(12) 0.0481(12) 0.0495(12) 0.0078(10) -0.0019(9) 0.0141(10) C4 0.0388(12) 0.0598(15) 0.0826(17) 0.0015(13) -0.0050(11) 0.0052(10) C5 0.0386(11) 0.0483(13) 0.0821(16) 0.0073(12) 0.0099(10) -0.0047(9) C6 0.0422(10) 0.0373(11) 0.0540(12) 0.0083(9) 0.0167(9) 0.0026(8) C7 0.0435(10) 0.0241(9) 0.0346(9) 0.0007(7) 0.0120(8) 0.0039(7) C8 0.0306(9) 0.0304(9) 0.0343(9) 0.0037(7) 0.0105(7) 0.0003(7) C9 0.0380(9) 0.0266(9) 0.0359(9) -0.0024(7) 0.0071(7) 0.0004(7) N1 0.0350(8) 0.0300(9) 0.0335(8) -0.0043(7) 0.0042(7) 0.0032(6) O1 0.0420(7) 0.0374(7) 0.0324(7) 0.0003(6) 0.0052(5) 0.0000(5) O2 0.0541(8) 0.0301(7) 0.0414(7) 0.0059(6) 0.0129(6) 0.0117(6) _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 C1 C9 1.536(2) . ? C1 C6 1.537(2) . ? C1 C7 1.541(2) . ? C1 C2 1.545(2) . ? C2 C3 1.528(3) . ? C3 C4 1.517(3) . ? C4 C5 1.519(3) . ? C5 C6 1.529(3) . ? C7 C8 1.521(2) . ? C8 O2 1.250(2) . ? C8 O1 1.263(2) . ? C9 N1 1.489(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 C9 C1 C6 107.89(14) . . ? C9 C1 C7 112.10(14) . . ? C6 C1 C7 109.83(14) . . ? C9 C1 C2 111.23(14) . . ? C6 C1 C2 108.42(15) . . ? C7 C1 C2 107.31(14) . . ? C3 C2 C1 114.03(16) . . ? C4 C3 C2 111.06(18) . . ? C3 C4 C5 110.80(17) . . ? C4 C5 C6 111.20(18) . . ? C5 C6 C1 113.94(17) . . ? C8 C7 C1 118.39(14) . . ? O2 C8 O1 123.78(16) . . ? O2 C8 C7 119.47(15) . . ? O1 C8 C7 116.75(15) . . ? N1 C9 C1 114.97(14) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.95 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.279 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.062