# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_General #TrackingRef '- gamma-glycine_P31(Asahi).cif' _audit_creation_date 2012-02-26 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'ENTER NAME' _publ_contact_author_email 'ENTER EMAIL ADDRESS' _publ_contact_author_fax 'ENTER FAX NUMBER' _publ_contact_author_phone 'ENTER PHONE NUMBER' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal test _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_footnote _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; _publ_section_synopsis ; ENTER SYNOPSIS ; #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Johnson, C.K. (1976). ORTEP-II. A FORTRAN Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Rigaku (1998). PROCESS-AUTO. Automatic Data Acquisition and Processing Package for Imaging Plate Diffractometer. Rigaku Corporation, Tokyo 196-8666, Japan Rigaku & RAC (2007). CrystalStructure (Version 3.80). Single Crystal Structure Analysis Software. Rigaku, Tokyo 196-8666, Japan. Rigaku Americas, TX, USA 77381-5209. Sheldrick, G.M. (1997). SHELXS97. Program for the Solution of Crystal Structures. University of Gottingen, Germany. Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #============================================================================== data_Sample-I _database_code_depnum_ccdc_archive 'CCDC 864813' #TrackingRef '- gamma-glycine_P31(Asahi).cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C2 H5 N O2' _chemical_formula_moiety 'C2 H5 N O2' _chemical_formula_weight 75.07 _chemical_melting_point ? _chemical_absolute_configuration ad #============================================================================== # CRYSTAL DATA _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 31' _symmetry_space_group_name_Hall 'P 31' _symmetry_Int_Tables_number 144 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -Y,+X-Y,1/3+Z 3 -X+Y,-X,2/3+Z #------------------------------------------------------------------------------ _cell_length_a 7.0111(3) _cell_length_b 7.0111(3) _cell_length_c 5.4843(4) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 120.0000 _cell_volume 233.47(3) _cell_formula_units_Z 3 _cell_measurement_reflns_used 6363 _cell_measurement_theta_min 7.29 _cell_measurement_theta_max 67.87 _cell_measurement_temperature 153 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 120.00 _exptl_absorpt_coefficient_mu 1.243 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.735 _exptl_absorpt_correction_T_max 0.975 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 153 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku VariMax with RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 9520 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_theta_max 67.87 _diffrn_reflns_theta_full 67.87 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measured_fraction_theta_full 0.976 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 561 _reflns_number_gt 559 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0691 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 561 _refine_ls_number_parameters 47 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.0036P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.240 _refine_diff_density_min -0.200 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 274 Friedel Pairs' _refine_ls_abs_structure_Flack -0.07(19) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.77950(13) 0.76681(12) 0.90785(16) 0.0188(3) Uani 1.0 3 d . . . O2 O 0.45500(14) 0.45669(14) 0.93959(15) 0.0245(3) Uani 1.0 3 d . . . N1 N 0.78433(14) 0.75542(13) 0.41858(19) 0.0160(3) Uani 1.0 3 d . . . C1 C 0.60731(18) 0.60774(17) 0.8207(2) 0.0166(3) Uani 1.0 3 d . . . C2 C 0.57656(18) 0.60239(18) 0.5449(3) 0.0199(3) Uani 1.0 3 d . . . H1A H 0.7610 0.7457 0.2547 0.0191 Uiso 1.0 3 calc R . . H1B H 0.8888 0.7190 0.4546 0.0191 Uiso 1.0 3 calc R . . H1C H 0.8309 0.8957 0.4687 0.0191 Uiso 1.0 3 calc R . . H2A H 0.5229 0.4508 0.4848 0.0239 Uiso 1.0 3 calc R . . H2B H 0.4635 0.6430 0.5061 0.0239 Uiso 1.0 3 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0200(5) 0.0191(5) 0.0137(4) 0.0070(4) -0.0003(4) -0.0022(4) O2 0.0250(5) 0.0217(5) 0.0179(4) 0.0050(4) 0.0040(4) -0.0003(4) N1 0.0186(6) 0.0163(5) 0.0126(5) 0.0085(4) -0.0008(4) 0.0005(4) C1 0.0179(6) 0.0173(6) 0.0167(6) 0.0103(5) 0.0001(5) -0.0012(4) C2 0.0154(6) 0.0205(6) 0.0190(7) 0.0054(5) 0.0001(4) -0.0007(5) #============================================================================== _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku & RAC 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_publication_material 'CrystalStructure (Rigaku & RAC 2007)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O1 C1 1.2583(12) yes . . O2 C1 1.2475(12) yes . . N1 C2 1.4800(13) yes . . C1 C2 1.5255(17) yes . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O1 C1 O2 126.05(11) yes . . . O1 C1 C2 117.36(9) yes . . . O2 C1 C2 116.55(9) yes . . . N1 C2 C1 111.75(9) yes . . . #============================================================================== data_Sample-II _database_code_depnum_ccdc_archive 'CCDC 864814' #TrackingRef '- gamma-glycine_P32(Asahi).cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C2 H5 N O2' _chemical_formula_moiety 'C2 H5 N O2' _chemical_formula_weight 75.07 _chemical_melting_point ? _chemical_absolute_configuration ad #============================================================================== # CRYSTAL DATA _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 32' _symmetry_space_group_name_Hall 'P 32' _symmetry_Int_Tables_number 145 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -Y,+X-Y,2/3+Z 3 -X+Y,-X,1/3+Z #------------------------------------------------------------------------------ _cell_length_a 7.01706(18) _cell_length_b 7.01706(18) _cell_length_c 5.48499(15) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 120.0000 _cell_volume 233.893(11) _cell_formula_units_Z 3 _cell_measurement_reflns_used 2243 _cell_measurement_theta_min 7.29 _cell_measurement_theta_max 67.75 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 120.00 _exptl_absorpt_coefficient_mu 1.241 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.561 _exptl_absorpt_correction_T_max 0.780 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 2285 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_theta_max 67.75 _diffrn_reflns_theta_full 67.75 _diffrn_measured_fraction_theta_max 0.955 _diffrn_measured_fraction_theta_full 0.955 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 543 _reflns_number_gt 534 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0748 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 543 _refine_ls_number_parameters 48 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens constr _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.190 _refine_diff_density_min -0.150 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.31(4) _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 260 Friedel Pairs' _refine_ls_abs_structure_Flack -0.03(24) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.54456(16) 0.54310(16) 0.48759(17) 0.0223(4) Uani 1.0 3 d . . . O2 O 0.22044(15) 0.23293(14) 0.51886(18) 0.0161(4) Uani 1.0 3 d . . . N3 N 0.21611(17) 0.24514(16) 1.0085(3) 0.0128(4) Uani 1.0 3 d . . . C4 C 0.3924(2) 0.39216(19) 0.6065(3) 0.0130(4) Uani 1.0 3 d . . . C5 C 0.4232(3) 0.3978(3) 0.8829(3) 0.0168(4) Uani 1.0 3 d . . . H3A H 0.1713 0.1048 0.9608 0.0153 Uiso 1.0 3 calc R . . H3B H 0.1108 0.2796 0.9697 0.0153 Uiso 1.0 3 calc R . . H3C H 0.2385 0.2569 1.1726 0.0153 Uiso 1.0 3 calc R . . H5A H 0.5363 0.3575 0.9220 0.0201 Uiso 1.0 3 calc R . . H5B H 0.4765 0.5493 0.9429 0.0201 Uiso 1.0 3 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0230(7) 0.0179(6) 0.0150(6) 0.0019(5) 0.0045(5) -0.0002(4) O2 0.0169(6) 0.0160(6) 0.0107(5) 0.0047(5) -0.0004(4) -0.0027(4) N3 0.0150(7) 0.0135(6) 0.0092(6) 0.0066(5) -0.0005(4) 0.0001(5) C4 0.0146(7) 0.0135(7) 0.0110(7) 0.0072(6) 0.0007(5) -0.0007(5) C5 0.0143(7) 0.0179(8) 0.0126(8) 0.0039(6) -0.0009(5) -0.0005(6) #============================================================================== _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku, 2000-2010)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_publication_material 'CrystalStructure (Rigaku, 2000-2010)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O1 C4 1.2473(14) yes . . O2 C4 1.2599(13) yes . . N3 C5 1.4758(16) yes . . C4 C5 1.5292(18) yes . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O1 C4 O2 125.97(12) yes . . . O1 C4 C5 116.51(10) yes . . . O2 C4 C5 117.47(10) yes . . . N3 C5 C4 111.66(10) yes . . . #===END========================================================================