# Supplementary Material (ESI) for PCCP # This journal is (c) the Owner Societies 2009 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _publ_contact_author_name 'B Hudson' _publ_contact_author_email BSHUDSON@SYR.EDU _publ_section_title ; Low-Temperature X-ray Structure Determination and Inelastic Neutron Scattering Spectroscopic Investigation of L-Alanine Alaninium Nitrate, a Homologue of a Ferroelectric ; loop_ _publ_author_name 'B Hudson' 'Damian Allis' 'Matthew R. Hudson' 'Wayne Ouellette' data_p21 _database_code_depnum_ccdc_archive 'CCDC 720351' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'L-alanine alaninium nitrate' _chemical_melting_point ? _chemical_formula_moiety 'C3 H8 N O2, C3 H7 N O2, N O3' _chemical_formula_sum 'C6 H15 N3 O7' _chemical_formula_weight 241.21 _chemical_absolute_configuration rm 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.7153(6) _cell_length_b 5.4523(5) _cell_length_c 12.7639(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.607(2) _cell_angle_gamma 90.00 _cell_volume 535.19(8) _cell_formula_units_Z 2 _cell_measurement_temperature 98(2) _cell_measurement_reflns_used 2903 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 31.43 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9603 _exptl_absorpt_correction_T_max 0.9654 _exptl_absorpt_process_details 'SADABS SHELXL-97 (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method 'Phi and omega scans' _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.001 _diffrn_reflns_number 5351 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 28.07 _reflns_number_total 1438 _reflns_number_gt 1418 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CrystalMaker (Palmer, 2006)' _computing_publication_material 'Bruker SHELXTL (Bruker, 2002)' _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 Rfactors 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^)+(0.0472P)^2^+0.4878P] 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 1438 _refine_ls_number_parameters 176 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1181 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.253 _refine_ls_restrained_S_all 1.252 _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 O5 O 0.8263(3) 0.1192(5) 0.29709(18) 0.0192(5) Uani 1 1 d . . . O4 O 0.2599(3) -0.0264(4) 0.21153(17) 0.0149(5) Uani 1 1 d . . . O1 O 0.2493(3) 0.1841(5) 0.38053(18) 0.0186(5) Uani 1 1 d . . . O2 O 0.1417(3) -0.1415(4) 0.46225(17) 0.0129(5) Uani 1 1 d . . . O3 O 0.3184(3) 0.0115(4) 0.04500(17) 0.0114(5) Uani 1 1 d . . . O6 O 0.6595(3) 0.2792(5) 0.1711(2) 0.0192(5) Uani 1 1 d . . . O7 O 0.7314(3) -0.1065(5) 0.16563(18) 0.0180(5) Uani 1 1 d . . . N1 N 0.1367(4) 0.1175(5) 0.6447(2) 0.0096(5) Uani 1 1 d . . . N2 N 0.3615(3) 0.5007(5) 0.0562(2) 0.0084(5) Uani 1 1 d . . . N3 N 0.7371(3) 0.0996(6) 0.2108(2) 0.0124(5) Uani 1 1 d . . . C1 C 0.2058(4) 0.0629(6) 0.4619(2) 0.0097(6) Uani 1 1 d . . . C2 C 0.2522(4) 0.2013(6) 0.5635(2) 0.0095(6) Uani 1 1 d . . . H2 H 0.2356 0.3812 0.5511 0.011 Uiso 1 1 calc R . . C3 C 0.4414(4) 0.1510(7) 0.6024(2) 0.0155(7) Uani 1 1 d . . . H3A H 0.4726 0.2493 0.6654 0.023 Uiso 1 1 calc R . . H3B H 0.5173 0.1951 0.5473 0.023 Uiso 1 1 calc R . . H3C H 0.4557 -0.0234 0.6194 0.023 Uiso 1 1 calc R . . C4 C 0.2859(4) 0.1007(6) 0.1309(2) 0.0095(6) Uani 1 1 d . . . C5 C 0.2652(4) 0.3788(6) 0.1385(2) 0.0093(6) Uani 1 1 d . . . H5A H 0.3130 0.4356 0.2095 0.011 Uiso 1 1 calc R . . C6 C 0.0723(4) 0.4464(6) 0.1223(3) 0.0165(7) Uani 1 1 d . . . H6A H 0.0589 0.6239 0.1308 0.025 Uiso 1 1 calc R . . H6B H 0.0079 0.3605 0.1743 0.025 Uiso 1 1 calc R . . H6C H 0.0268 0.3983 0.0514 0.025 Uiso 1 1 calc R . . H2C H 0.340(5) 0.652(8) 0.055(3) 0.000(8) Uiso 1 1 d . . . H1B H 0.167(4) 0.192(8) 0.703(3) 0.001(8) Uiso 1 1 d . . . H1C H 0.142(6) -0.051(10) 0.652(3) 0.018(11) Uiso 1 1 d . . . H1A H 0.028(5) 0.159(9) 0.621(3) 0.016(10) Uiso 1 1 d . . . H2B H 0.475(5) 0.468(8) 0.069(3) 0.007(9) Uiso 1 1 d . . . H2A H 0.322(5) 0.445(8) -0.008(3) 0.010(9) Uiso 1 1 d . . . H1 H 0.241(8) 0.103(15) 0.326(5) 0.06(2) 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 O5 0.0321(13) 0.0122(12) 0.0122(11) 0.0012(10) -0.0058(9) -0.0036(11) O4 0.0280(12) 0.0073(10) 0.0097(10) -0.0001(9) 0.0034(9) -0.0012(10) O1 0.0314(13) 0.0161(13) 0.0086(11) -0.0009(9) 0.0037(9) -0.0072(11) O2 0.0140(10) 0.0128(12) 0.0117(10) -0.0021(9) -0.0006(8) -0.0030(9) O3 0.0138(10) 0.0087(11) 0.0120(10) -0.0012(9) 0.0027(8) 0.0004(9) O6 0.0187(12) 0.0138(12) 0.0243(12) 0.0035(11) -0.0034(9) 0.0019(10) O7 0.0279(13) 0.0128(11) 0.0128(11) -0.0032(9) -0.0008(9) 0.0008(11) N1 0.0132(12) 0.0096(13) 0.0061(11) -0.0026(11) 0.0012(9) -0.0016(10) N2 0.0106(12) 0.0049(13) 0.0102(12) -0.0003(10) 0.0030(9) 0.0022(10) N3 0.0151(12) 0.0114(13) 0.0107(11) 0.0021(11) 0.0015(9) -0.0009(11) C1 0.0055(12) 0.0117(16) 0.0117(13) -0.0010(11) -0.0009(10) 0.0018(11) C2 0.0119(13) 0.0056(13) 0.0109(13) 0.0000(11) 0.0009(10) -0.0030(11) C3 0.0119(13) 0.0202(18) 0.0140(14) -0.0039(13) -0.0019(11) -0.0047(13) C4 0.0080(12) 0.0071(13) 0.0133(13) 0.0022(12) -0.0001(10) 0.0012(11) C5 0.0111(13) 0.0084(14) 0.0090(13) -0.0006(11) 0.0036(10) -0.0019(12) C6 0.0084(13) 0.0116(16) 0.0304(18) -0.0025(13) 0.0069(12) 0.0031(12) _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 O5 N3 1.256(3) . ? O4 C4 1.270(4) . ? O1 C1 1.298(4) . ? O1 H1 0.82(7) . ? O2 C1 1.220(4) . ? O3 C4 1.243(4) . ? O6 N3 1.235(4) . ? O7 N3 1.262(4) . ? N1 C2 1.492(4) . ? N1 H1B 0.86(4) . ? N1 H1C 0.92(5) . ? N1 H1A 0.90(4) . ? N2 C5 1.491(4) . ? N2 H2C 0.84(4) . ? N2 H2B 0.89(4) . ? N2 H2A 0.90(4) . ? C1 C2 1.518(4) . ? C2 C3 1.528(4) . ? C2 H2 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.529(5) . ? C5 C6 1.531(4) . ? C5 H5A 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? 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 C1 O1 H1 113(5) . . ? C2 N1 H1B 108(2) . . ? C2 N1 H1C 111(3) . . ? H1B N1 H1C 112(4) . . ? C2 N1 H1A 107(3) . . ? H1B N1 H1A 111(4) . . ? H1C N1 H1A 108(4) . . ? C5 N2 H2B 110(2) . . ? C5 N2 H2A 109(2) . . ? H2B N2 H2A 113(4) . . ? C5 N2 H2C 110(3) . . ? H2B N2 H2C 105(4) . . ? H2A N2 H2C 111(3) . . ? O6 N3 O5 120.4(3) . . ? O6 N3 O7 121.4(2) . . ? O5 N3 O7 118.2(3) . . ? O2 C1 O1 126.8(3) . . ? O2 C1 C2 121.3(3) . . ? O1 C1 C2 111.9(3) . . ? N1 C2 C1 109.2(2) . . ? N1 C2 C3 109.1(2) . . ? C1 C2 C3 110.0(2) . . ? N1 C2 H2 109.5 . . ? C1 C2 H2 109.5 . . ? C3 C2 H2 109.5 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O3 C4 O4 123.9(3) . . ? O3 C4 C5 118.3(3) . . ? O4 C4 C5 117.8(3) . . ? N2 C5 C4 109.7(3) . . ? N2 C5 C6 109.3(3) . . ? C4 C5 C6 109.6(3) . . ? N2 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? 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 O2 C1 C2 N1 -27.2(4) . . . . ? O1 C1 C2 N1 155.4(3) . . . . ? O2 C1 C2 C3 92.5(3) . . . . ? O1 C1 C2 C3 -84.9(3) . . . . ? O3 C4 C5 N2 -24.6(4) . . . . ? O4 C4 C5 N2 158.9(2) . . . . ? O3 C4 C5 C6 95.4(3) . . . . ? O4 C4 C5 C6 -81.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.07 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.414 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.071