# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Parsons, Simon' 'Marshall, William' 'Funnell, Nicholas' _publ_contact_author_name 'Parsons, Simon' _publ_contact_author_email S.PARSONS@ED.AC.UK _publ_section_title ; Alanine at 13.6 GPa and its Pressure-Induced Amorphisation at 15 GPa ; # Attachment '- all.cif' data_alanine_11.74_GPa _database_code_depnum_ccdc_archive 'CCDC 823373' #TrackingRef '- all.cif' _chemical_name_systematic ; L-alanine-d7 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 D7 N O2' _chemical_formula_structural ? _chemical_formula_sum 'C3 D7 N O2' _chemical_formula_iupac ? _chemical_formula_weight 96.11 _chemical_compound_source 'see text' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z _cell_length_a 5.18289(48) _cell_length_b 11.1940(12) _cell_length_c 5.43875(53) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 315.541(55) _cell_formula_units_Z 4 _cell_measurement_temperature 315 _cell_measurement_pressure 11.75(2) #GPa _cell_special_details ; Cell parameters included in refinement ; _exptl_crystal_density_diffrn 2.023 _pd_spec_mounting 'TiZr Capsule' _pd_spec_mount_mode transmission _pd_char_particle_morphology Block _pd_char_colour Colourless _chemical_absolute_configuration rm _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; Calculated using custom ISIS software. ; _pd_instr_location 'ISIS, Rutherford Appleton Laboratory' _diffrn_ambient_temperature 315 _diffrn_source 'Pulsed neutron source' _diffrn_source_target ? _diffrn_radiation_type Neutron _diffrn_measurement_device_type 'HiPr/PEARL, ISIS' _diffrn_radiation_monochromator ? _diffrn_detector 'ZnS scintillator' _diffrn_detector_type custom _pd_meas_scan_method Time-of-flight _pd_meas_special_details ; Time of flight method using a pulsed neutron source ; # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec 12600 _pd_instr_dist_spec/detc 600 _pd_meas_2theta_fixed 90 _pd_proc_ls_profile_function ; Voigt function convoluted with a back-to-back double exponential. ; _pd_proc_ls_background_function 'Chebychev polynomial' _pd_proc_ls_pref_orient_corr ; Modelling of preferred orientation was found to be unnecessary. ; _pd_proc_ls_prof_R_factor 5.151 _pd_proc_ls_prof_wR_factor 4.672 _pd_proc_ls_prof_R_expected 3.539 _refine_ls_goodness_of_fit_all 1.320 _refine_ls_matrix_type sparse _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ? _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_parameters 66 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_diff_density_max ? _refine_diff_density_min ? _refine_ls_shift/su_max <0.001 _pd_proc_info_excluded_regions ; ? ; _pd_proc_info_data_reduction ; Custom ISIS software ; _refine_special_details ; The data in this cif come from a Rietveld refinement against neutron powder data. Details of the refinement are given in the paper. Check-cif alerts 023_ALERT_3_B Resolution (too) Low [sin(theta)/Lambda < 0.6].. 0.00 Deg. The neutron time-of-flight method was used. 025_ALERT_1_B Hmin..Lmax Data Incomplete or Missing .......... ? h runs from 0 to 8 k from 0 to 17 l from 0 to 8 027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 0.00 Deg. 029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.00 037_ALERT_1_B _diffrn_reflns_theta_full .......... Not Given . ? 038_ALERT_1_B _diffrn_measured_fraction_theta_max Not Given . ? 039_ALERT_1_B _diffrn_measured_fraction_theta_full Not Given . ? These alerts relate to single-crystal experiments 050_ALERT_1_B Absorption Coefficient mu Missing .............. ? The absorption coefficient varies with wavelength. An attenuation curve for the cell is given in Fig 2 of the paper. 095_ALERT_1_B No Residual Density Maximum Given .............. ? 096_ALERT_1_B No Residual Density Minimum Given .............. ? Topas does not output these data 201_ALERT_2_C Isotropic non-H Atoms in Main Residue(s) ....... 6 210_ALERT_3_C No Anisotropic ADP's Found in CIF .............. ? 415_ALERT_2_C Short Inter D-H..H-X H2 .. H4 .. 2.09 Ang. 415_ALERT_2_C Short Inter D-H..H-X H3 .. H6 .. 2.06 Ang. 432_ALERT_2_C Short Inter X...Y Contact O2 .. C1 .. 2.83 Ang. 432_ALERT_2_C Short Inter X...Y Contact O2 .. C2 .. 2.85 Ang. 432_ALERT_2_C Short Inter X...Y Contact C1 .. C3 .. 3.05 Ang. 413_ALERT_2_G Short Inter XH3 .. XHn H6 .. H7 .. 2.13 Ang. 415_ALERT_2_G Short Inter D-H..H-X H3 .. H5 .. 2.11 Ang. 430_ALERT_2_G Short Inter D...A Contact O1 .. O2 .. 2.87 Ang. The data reported are at high pressure (11.74 GPa). Short contacts are to be expected. At this pressure the molecule could not be reliably refined anisotropically thus a constrained istropic model was used for displacement parameters 040_ALERT_1_G No H-atoms in this Carbon Containing Compound .. ? The molecule was fully deuterated 161_ALERT_4_G Missing or Zero su (esd) on x-coordinate for ... N1 161_ALERT_4_G Missing or Zero su (esd) on x-coordinate for ... O1 161_ALERT_4_G Missing or Zero su (esd) on x-coordinate for ... O2 161_ALERT_4_G Missing or Zero su (esd) on x-coordinate for ... C1 161_ALERT_4_G Missing or Zero su (esd) on x-coordinate for ... C2 161_ALERT_4_G Missing or Zero su (esd) on x-coordinate for ... C3 162_ALERT_4_G Missing or Zero su (esd) on y-coordinate for ... N1 162_ALERT_4_G Missing or Zero su (esd) on y-coordinate for ... O1 162_ALERT_4_G Missing or Zero su (esd) on y-coordinate for ... O2 162_ALERT_4_G Missing or Zero su (esd) on y-coordinate for ... C1 162_ALERT_4_G Missing or Zero su (esd) on y-coordinate for ... C2 162_ALERT_4_G Missing or Zero su (esd) on y-coordinate for ... C3 163_ALERT_4_G Missing or Zero su (esd) on z-coordinate for ... N1 163_ALERT_4_G Missing or Zero su (esd) on z-coordinate for ... O1 163_ALERT_4_G Missing or Zero su (esd) on z-coordinate for ... O2 163_ALERT_4_G Missing or Zero su (esd) on z-coordinate for ... C1 163_ALERT_4_G Missing or Zero su (esd) on z-coordinate for ... C2 163_ALERT_4_G Missing or Zero su (esd) on z-coordinate for ... C3 The standard deviations on the atomic coordinates are not propagated through by Topas 720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 7 The numbering scheme used matches that of our previous publication of the high pressure structure of L-alanine ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv N1 N 0 0.6564647 0.1368398 0.09304553 1 0.89(11) O1 O 0 0.7507449 0.09278915 0.558133 1 0.89(11) O2 O 0 0.3874455 0.1861707 0.6749785 1 0.89(11) C1 C 0 0.5416211 0.1440141 0.5236305 1 0.89(11) C2 C 0 0.454408 0.1592811 0.2638278 1 0.89(11) C3 C 0 0.2276423 0.08255123 0.2007367 1 0.89(11) H1 D 0 0.7132701 0.04784006 0.1056695 1 1.14(13) H2 D 0 0.5914616 0.1543165 -0.08447381 1 1.14(13) H3 D 0 0.8129619 0.1918922 0.1325953 1 1.14(13) H4 D 0 0.4013232 0.2541592 0.2446337 1 1.14(13) H5 D 0 0.0799394 0.09348558 0.3447593 1 1.14(13) H6 D 0 0.1510597 0.1112387 0.0211581 1 1.14(13) H7 D 0 0.2920079 -0.01118208 0.1917995 1 1.14(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2405 . . yes O2 C1 1.2405 . . yes N1 C2 1.4222 . . yes N1 H2 1.0400 . . yes N1 H3 1.0400 . . yes N1 H1 1.0400 . . yes C1 C2 1.4934 . . no C2 C3 1.4956 . . no C2 H4 1.1000 . . yes C3 H5 1.1000 . . yes C3 H6 1.1000 . . yes C3 H7 1.1000 . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 H2 110.00 . . . yes C2 N1 H3 110.00 . . . yes H1 N1 H2 109.00 . . . yes H1 N1 H3 109.00 . . . yes H2 N1 H3 109.00 . . . yes C2 N1 H1 110.00 . . . yes O1 C1 C2 117.42 . . . yes O1 C1 O2 129.67 . . . yes O2 C1 C2 112.91 . . . yes C1 C2 C3 112.91 . . . no N1 C2 C1 112.02 . . . yes N1 C2 C3 109.11 . . . yes N1 C2 H4 107.00 . . . yes C1 C2 H4 106.00 . . . yes C3 C2 H4 110.00 . . . yes C2 C3 H5 109.00 . . . yes C2 C3 H6 109.00 . . . yes C2 C3 H7 109.00 . . . yes H5 C3 H6 110.00 . . . yes H5 C3 H7 110.00 . . . yes H6 C3 H7 110.00 . . . yes 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 O1 C1 C2 N1 -13.88 . . . . no O1 C1 C2 C3 109.77 . . . . no O2 C1 C2 N1 166.12 . . . . no O2 C1 C2 C3 -70.23 . . . . no data_alanine_13_60_GPa _database_code_depnum_ccdc_archive 'CCDC 823374' _chemical_name_systematic ; L-alanine-d7 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C3 D7 N O2' _chemical_formula_structural ? _chemical_formula_sum 'C3 D7 N O2' _chemical_formula_iupac ? _chemical_formula_weight 96.11 _chemical_compound_source 'see text' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z _cell_length_a 5.13617(71) _cell_length_b 11.1258(19) _cell_length_c 5.41457(76) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 309.411(80) _symmetry_space_group_name_H-M P212121 _cell_formula_units_Z 4 _cell_measurement_temperature 340 _cell_measurement_pressure 13.60(2) #GPa _cell_special_details ; Cell parameters included in refinement ; _exptl_crystal_density_diffrn 2.063 _pd_spec_mounting 'TiZr Capsule' _pd_spec_mount_mode transmission _pd_char_particle_morphology Block _pd_char_colour Colourless _chemical_absolute_configuration rm _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; Calculated using custom ISIS software. ; _pd_instr_location 'ISIS, Rutherford Appleton Laboratory' _diffrn_ambient_temperature 340 _diffrn_source 'Pulsed neutron source' _diffrn_source_target ? _diffrn_radiation_type Neutron _diffrn_measurement_device_type 'HiPr/PEARL, ISIS' _diffrn_radiation_monochromator ? _diffrn_detector 'ZnS scintillator' _diffrn_detector_type custom _pd_meas_scan_method Time-of-flight _pd_meas_special_details ; Time of flight method using a pulsed neutron source ; # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec 12600 _pd_instr_dist_spec/detc 600 _pd_meas_2theta_fixed 90 _pd_proc_ls_profile_function ; Voigt function convoluted with a back-to-back double exponential. ; _pd_proc_ls_background_function 'Chebychev polynomial' _pd_proc_ls_pref_orient_corr ; Modelling of preferred orientation was found to be unnecessary. ; _pd_proc_ls_prof_R_factor 5.343 _pd_proc_ls_prof_wR_factor 4.922 _pd_proc_ls_prof_R_expected 3.888 _refine_ls_goodness_of_fit_all 1.266 _refine_ls_matrix_type sparse _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ? _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_parameters 66 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_diff_density_max ? _refine_diff_density_min ? _refine_ls_shift/su_max <0.001 _pd_proc_info_excluded_regions ; ? ; _pd_proc_info_data_reduction ; Custom ISIS software ; _refine_special_details ; The data in this cif come from a Rietveld refinement against neutron powder data. Details of the refinement are given in the paper. Check-cif alerts 023_ALERT_3_B Resolution (too) Low [sin(theta)/Lambda < 0.6].. 0.00 Deg. The neutron time-of-flight method was used. 025_ALERT_1_B Hmin..Lmax Data Incomplete or Missing .......... ? h runs from 0 to 8 k from 0 to 17 l from 0 to 8 027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 0.00 Deg. 029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.00 037_ALERT_1_B _diffrn_reflns_theta_full .......... Not Given . ? 038_ALERT_1_B _diffrn_measured_fraction_theta_max Not Given . ? 039_ALERT_1_B _diffrn_measured_fraction_theta_full Not Given . ? These alerts relate to single-crystal experiments 050_ALERT_1_B Absorption Coefficient mu Missing .............. ? The absorption coefficient varies with wavelength. An attenuation curve for the cell is given in Fig 2 of the paper. 095_ALERT_1_B No Residual Density Maximum Given .............. ? 096_ALERT_1_B No Residual Density Minimum Given .............. ? Topas does not output these data 201_ALERT_2_C Isotropic non-H Atoms in Main Residue(s) ....... 6 210_ALERT_3_C No Anisotropic ADP's Found in CIF .............. ? 415_ALERT_2_C Short Inter D-H..H-X H2 .. H4 .. 2.03 Ang. 415_ALERT_2_C Short Inter D-H..H-X H3 .. H6 .. 2.05 Ang. 430_ALERT_2_C Short Inter D...A Contact O1 .. O2 .. 2.71 Ang. 432_ALERT_2_C Short Inter X...Y Contact O2 .. C1 .. 2.73 Ang. 432_ALERT_2_C Short Inter X...Y Contact O2 .. C2 .. 2.83 Ang. 432_ALERT_2_C Short Inter X...Y Contact C1 .. C3 .. 3.05 Ang. 413_ALERT_2_G Short Inter XH3 .. XHn H6 .. H7 .. 2.11 Ang. 415_ALERT_2_G Short Inter D-H..H-X H3 .. H5 .. 2.10 Ang. 415_ALERT_2_G Short Inter D-H..H-X H3 .. H4 .. 2.11 Ang. 432_ALERT_2_G Short Inter X...Y Contact O1 .. C2 .. 3.01 Ang. The data reported are at high pressure (13.60 GPa). Short contacts are to be expected. At this pressure the molecule could not be reliably refined anisotropically thus a constrained istropic model was used for displacement parameters 040_ALERT_1_G No H-atoms in this Carbon Containing Compound .. ? The molecule was fully deuterated 161_ALERT_4_G Missing or Zero su (esd) on x-coordinate for ... N1 161_ALERT_4_G Missing or Zero su (esd) on x-coordinate for ... O1 161_ALERT_4_G Missing or Zero su (esd) on x-coordinate for ... O2 161_ALERT_4_G Missing or Zero su (esd) on x-coordinate for ... C1 161_ALERT_4_G Missing or Zero su (esd) on x-coordinate for ... C2 161_ALERT_4_G Missing or Zero su (esd) on x-coordinate for ... C3 162_ALERT_4_G Missing or Zero su (esd) on y-coordinate for ... N1 162_ALERT_4_G Missing or Zero su (esd) on y-coordinate for ... O1 162_ALERT_4_G Missing or Zero su (esd) on y-coordinate for ... O2 162_ALERT_4_G Missing or Zero su (esd) on y-coordinate for ... C1 162_ALERT_4_G Missing or Zero su (esd) on y-coordinate for ... C2 162_ALERT_4_G Missing or Zero su (esd) on y-coordinate for ... C3 163_ALERT_4_G Missing or Zero su (esd) on z-coordinate for ... N1 163_ALERT_4_G Missing or Zero su (esd) on z-coordinate for ... O1 163_ALERT_4_G Missing or Zero su (esd) on z-coordinate for ... O2 163_ALERT_4_G Missing or Zero su (esd) on z-coordinate for ... C1 163_ALERT_4_G Missing or Zero su (esd) on z-coordinate for ... C2 163_ALERT_4_G Missing or Zero su (esd) on z-coordinate for ... C3 The standard deviations on the atomic coordinates are not propagated through by Topas 720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 7 The numbering scheme used matches that of our previous publication of the high pressure structure of L-alanine ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv N1 N 0 0.6537916 0.1379916 0.09267515 1 1.13(20) O1 O 0 0.7531725 0.1016853 0.5534029 1 1.13(20) O2 O 0 0.3842419 0.1868974 0.6602988 1 1.13(20) C1 C 0 0.545998 0.1471266 0.5267844 1 1.13(20) C2 C 0 0.4519415 0.1606481 0.2591086 1 1.13(20) C3 C 0 0.2245156 0.08203456 0.1970383 1 1.13(20) H1 D 0 0.714473 0.04772084 0.1076598 1 1.23(22) H2 D 0 0.5898181 0.1540175 -0.08946949 1 1.23(22) H3 D 0 0.8132999 0.1947022 0.1310286 1 1.23(22) H4 D 0 0.3949726 0.2549606 0.2362207 1 1.23(22) H5 D 0 0.07560337 0.09218419 0.3406063 1 1.23(22) H6 D 0 0.1455441 0.1094728 0.01756829 1 1.23(22) H7 D 0 0.2901121 -0.01165053 0.188648 1 1.23(22) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.1869 . . yes O2 C1 1.1869 . . yes N1 C2 1.3966 . . yes N1 H2 1.0500 . . yes N1 H3 1.0500 . . yes N1 H1 1.0500 . . yes C1 C2 1.5351 . . no C2 C3 1.4975 . . no C2 H4 1.1000 . . yes C3 H5 1.1000 . . yes C3 H6 1.1000 . . yes C3 H7 1.1000 . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 H2 110.00 . . . yes C2 N1 H3 110.00 . . . yes H1 N1 H2 109.00 . . . yes H1 N1 H3 109.00 . . . yes H2 N1 H3 109.00 . . . yes C2 N1 H1 110.00 . . . yes O1 C1 C2 116.01 . . . yes O1 C1 O2 135.43 . . . yes O2 C1 C2 108.56 . . . yes C1 C2 C3 113.59 . . . no N1 C2 C1 110.97 . . . yes N1 C2 C3 109.20 . . . yes N1 C2 H4 107.00 . . . yes C1 C2 H4 107.00 . . . yes C3 C2 H4 109.00 . . . yes C2 C3 H5 109.00 . . . yes C2 C3 H6 109.00 . . . yes C2 C3 H7 109.00 . . . yes H5 C3 H6 110.00 . . . yes H5 C3 H7 110.00 . . . yes H6 C3 H7 110.00 . . . yes 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 O1 C1 C2 N1 -11.94 . . . . no O1 C1 C2 C3 111.54 . . . . no O2 C1 C2 N1 168.06 . . . . no O2 C1 C2 C3 -68.46 . . . . no